Some features of the modern world are so ubiquitous, so commonplace, that it is particularly surprising and illustrative to realize what creativity and ingenuity went into bringing them about.

If you’ve ever been to a rock climbing gym even casually in the last 30 years, you will have encountered a category of climbing called bouldering. For climbers today, bouldering is like hallways. It’s obvious and it’s always been there. It is the most common and popular form of climbing. It’s all the technique and athleticism of rock climbing, but low enough to the ground that it’s safe to fall on pads; no ropes, harnesses, or other special gear is required. It’s the sport of choice for many of my ambitious tech founder clients, and no wonder: what better, faster way to nourish your builder’s mindset than to concentrate all your creative and physical powers on solving a short, intensely challenging “boulder problem”?

And yet: 60 years ago, bouldering did not exist. The entire sport of rock climbing was barely even a sport. Some people engaged in it, but they conceptualized it as something akin to “extreme hiking.” Just as with hallways, a small number of people, in this case one person in particular, had to rethink the sport; had to notice latent possibilities and think about them afresh, by analogy to things other than hiking; then had to work out the details, developing a new form of the activity.

This came into clearer focus for me as I listened to episode 4 of the Climbing Gold podcast co-hosted by Alex Honnold (whose legendary climbing feats you may recall from the movie Free Solo) and Fitz Cahall:

“Bouldering has become the most popular, the most accessible, the most athletic, the most pervasive form of climbing today. The essence of the sport gets distilled down into a few moves typically no higher than a single story building. It’s an incredible path into the sport because there’s no technical rope skills required… If you were to walk up to one of these [bouldering] areas on a busy weekend, you’d find people working out sequences of moves until perfection, dipping their hands into buckets of chalk, lunging dynamically for holds, cheering for each other with each tiny summit reached. It all seems so intuitive when you look at it. The dynamic movement, the chalk, the ‘practice makes perfect’ mentality.

Sometimes it’s easy to forget that somebody actually invented all of that [emphasis added]. And the light bulb went off, not in Yosemite, but in an Intro to Gymnastics class in the 1950s, while a young freshman was fulfilling a PE requirement.”

That young freshman was John Gill, whom Alex and Fitz proceed to interview in the episode. Now 88 years old, Gill pioneered the art of bouldering back in the 50s by reconceptualizing rock climbing as an extension of gymnastics rather than hiking. He developed his then-radical approach to climbing while getting his undergraduate and advanced degrees in math, serving as a meteorologist for the U.S. Air Force, and spending the brunt of his career as a math professor.

Intrigued by his story and the transformative influence he has had on climbing, I reached out for an interview. He replied within hours, offering to answer my questions by email. Here is our (lightly redacted and annotated) exchange, followed by some reflections on what Gill’s story crystalizes about the builder’s mindset:

Me: In the decades before bouldering became mainstream, I understand you were viewed as somewhat of an anomaly in the climbing world. How did you relate to this fact, and how did you view your own role? Did you consciously view yourself as pioneering something important and new that ought to be adopted by other climbers, or did you view it more as a personal project, or something else?

Gill: I got used to being described as a “mere boulderer” and much later in life made a T-shirt with that written on it. I was introduced to climbing as a junior in high school in 1953 by a classmate who had learned the bare essentials at Cheley Camp in Estes Park the previous summer. There were no books or magazines on the subject available to me so I learned the sport pretty much on my own, scrambling around various rocks in Georgia. Then, after graduation, a friend and I drove to Colorado in August of 1954 and I scrambled solo up the east face of Longs Peak (you can hear me describe this on Alex Honnold’s Climbing Gold podcast episode 4). Thus, I was following a path common to neophyte climbers at the time. But that Fall I enrolled in a gymnastics class at Georgia Tech and my perception of climbing began to change. I no longer imagined the sport as an outgrowth of hiking, but began seeing it as an extension of gymnastics, and where better to exercise this perception than on boulders and small outcrops.

There seemed to be a huge disparity in pure strength between climbers and gymnasts, with rock climbers doing a few pushups while gymnasts were holding inverted crosses on the still rings. In a couple of years I put on 25 pounds of muscle and began doing moves on boulders that exceeded existing levels of difficulty, and doing them smoothly, like a gymnastic routine. I sensed I was fortunate to be at a formative stage in the evolution of climbing in America, and I clearly saw into a future in which bouldering’s growth was inevitable. At the same time I imagined the ultimate form of rock climbing as “free solo exploration”, and experimented with that approach to longer climbs until reaching my limits on the Thimble in 1961. [Gill famously climbed the Thimble, a steep 30-foot granite spire in the Needles of South Dakota, from the ground up and without a rope: a feat no one would be able to repeat for another 20 years. See “Reflections” below for some insight into how and why he did it.] A friend and executive director of the American Alpine Club, Jim McCarthy, encouraged me to write an article for the AAC Journal describing my vision of bouldering.

As an aside, I used to “boulder” on the campus of the U of Texas [where Gill noticed I am currently a faculty member] in 1948-49 where my dad was getting his PhD…. Also, during 1958-59, Mihaly Csikszentmihalyi, Father of Flow, was a member of the small U of Chicago mountaineering club that drove to Devils Lake to climb. Flow during a bouldering “performance” was very important to me at the time, although this aspect of my vision failed to take root.

Me: You introduced things (chalk, dynamics, an early grading system) that were controversial or novel at the time. Did the controversy or pushback affect you? If so, how, and how did you deal with it?

Gill: Chalk was by far the most controversial. I bouldered with [Patagonia founder] Yvon Chouinard in the Tetons during the late 1950s – he coined the expression for bouldering, “Instant Suffering “ - and he chose not to use it, but he wasn’t particularly upset by its use. Others were more disturbed by it and must have let their strongest feelings out when I was not around. I don’t recall anyone confronting me about its use. So, I didn’t have to deal with it.

Me: Do you see yourself equally as a “mathematician” and a “climber”? Does one feel more fundamental than the other? Is the former your job and the latter your hobby, or how do you conceptualize it? How has this evolved across different stages of your life?

Gill: I was an only child and we moved about every two years or so. In high school I grew to over six feet, but weighed only 145 lbs. and was no athlete. Glee club and ROTC. This bothered me, but when I began climbing in 1953 I saw a path I could follow and build my personality and, hopefully, my physique. I didn’t see myself as a mathematician until leaving the Service and enrolling in grad school. I became a mathematician when I did original research and got my PhD in 1971. Thereafter, I was a math professor who had the avocation of climbing.

Me: Do you mention being an only child and moving every couple of years because these factors made it harder to build a stable personality / set of friends and interests, which you then saw a path to doing through climbing? Or am I misunderstanding the relevance of these early influences? Also: was there anything or anyone in particular that shaped your view of physical strength / fitness / “being an athlete” as positive traits to strive for? Was this a general cultural norm at the time, and/or did it partly have to do with romantic/dating goals, and/or were there particular athletes you admired, etc?

Gill: I think moving every couple of years made me more introverted and singular in my activities, so climbing seemed very attractive and had an exploratory element that appealed. The one person I really admired after learning about the sport was the Armenian gymnast Albert Azaryan. His performances on the still rings were inspiring. As for climbers, none come to mind, although I respected a number, including Royal Robbins. I was a year younger than my classmates and was envious of their physiques and burgeoning maturity. I needed a more muscular body, but wasn’t sure how to accomplish that. At first I thought climbing would do the trick, but when I saw how gymnastics developed the musculature I was entranced. At that time being tall was not an impediment. John Becker, the American champion, was six feet. These days one must be shorter for moves that are more difficult than before.

Me: How would you describe your dominant motivations for climbing, for doing your academic work, and for any other activities that have occupied significant portions of your life? What needs did each activity fulfill for you? Are there any needs you feel haven’t gotten fully met in your life, or not until later on?

Gill: Where is the overlap between mathematics and climbing? Exploration. I never enjoyed repeating something someone else had done first. I trudged through grad school, working on problems at the end of the chapter, but I didn’t come alive until I began exploring the unknown. As for bouldering, it gave a purpose to my life: advocating its acceptance as a legitimate sport. As a novice climber I was obsessed with what I saw as an ultimate form of the sport, Free Solo Exploration; and after finding my limits along that path I reduced the risk factor considerably, but continued the practice until a revelatory moment in the early 2000s that convinced me to retire from the sport.

Me: Anything you’d be willing to share about the specific nature of the “revelatory moment”? Did this have to do with your reflections in the “Climbing Gold” podcast episode about the injuries and spinal damage you accrued due to bouldering?

Gill: After 1987 I only did modest bouldering and moderate free solos. Exploratory rambles. There were several granite formations in Hardscrabble Canyon, not far from Pueblo, that I climbed over and over again for the pure exercise and flow. One was a pinnacle that stood high above the highway through the canyon and caught your eye when you drove. I had free soloed a highly exposed but modest route up its face years before, then occasionally returned. This time when I reached a very exposed point on the nearly vertical face where one has to balance over to a refrigerator sized detached block, leaving all handholds for a moment, as I gently shifted weight onto my left foot – in the calm and quiet of the day – the block began to shift. This was a paralyzing moment, but I quickly decided to continue the move, reaching up for a handhold in the process. I stood and pulled off the block – which remained attached to the wall – glancing down the 900 feet to the canyon road. I was in my mid 60s and had free solo explored perhaps 50 miles of rock over the years – and I interpreted this as a message, fatal if ignored.

Me: I know you’ve often described climbing as a spiritual, aesthetic, almost “metaphysical” experience. To what extent did your aspirations for the future (whether short- or long-term) play a part in how you approached and experienced climbing, vs to what extent was it really a present-focused, meditative activity?

Gill: The aspect of climbing that could be described as meditative is the sense of flow. I mentioned Mihaly C. who devoted his career to this subject, in all its settings. As I learned gymnastics I experienced flow upon polishing a short routine on the rings or a fast climb on the rope. Also, I felt it to be an important part of climbing, although I was virtually alone in this regard. Once the Verm (John Sherman) introduced his V-grading system the numbers race began. I had been using a grade system designed to discourage number chasing, but I clearly had misunderstood human nature.

Me: Looking back on your life and career, is there anything you would do differently, if you had a do-over?

Gill: “What ifs...” have never interested me. [Touché! Probably the best response anyone could give to this question, honestly.]

Me: Your origin story includes some important early inflection points: the high school trip with your friend, the gymnastics class to fulfill your university’s PE requirement (if I understand correctly), etc. Do you think your life would have gone very differently if not for these serendipitous events, or do you think you would have found your way to bouldering or another movement-based art no matter what?

Gill: Alternate histories are fun sci fi reads. What might interest you is that, while a young USAF officer stationed at a distant air base in the early 1960s, I read Sartre’s Being and Nothingness, and became a practicing existentialist. I believe we create our own destinies when conditions allow, and we generate meaning within our lives.

[This concluded the substantive portion of our email conversation, after which I thanked him profusely and he asked for a copy of whatever I end up saying about him in my book.]

Reflections: A study in the builder’s mindset

In pioneering a new category of sport, Gill created not only his own destiny, but a new set of conditions that did not exist before. And, like the consummate builder he was, he applied this same level of fresh thinking and intentionality not just to the sport of bouldering, but to the design of his life as a whole. With every chosen pursuit, he laid down another building block in the nested hierarchy of valued pursuits that together both enabled and constituted his singular form of fully-lived life. He took up climbing, partly as a means to develop the strong physique he admired in his older classmates, and partly because it afforded him opportunities for the solitary exploration he loved. Then he discovered that he could build up his physique better and faster through gymnastics, and that he could get the combined value of both sports by integrating them. In time he realized this new form of climbing he had developed could shape the future of a young and rapidly evolving sport and community he had come to value, and that his role in advocating for its acceptance could give “purpose to [his] life.”

As testament to his builder’s knack for integrated life design, here is Gill’s recollection of why he decided to climb the Thimble (from an interview he gave at age 39 for the book Master of Rock):

“I suppose it was a psychological point in my climbing career, and I felt as though I had to really produce, really do something substantial…. I felt as though I had to do something with an element of risk in it, something difficult.”

Note how strategically Gill approached his risk calculus, welcoming greater risk at certain important inflection points in his life and prioritizing safety more highly at other times.

As to how he prepared for his historic ascent of the Thimble:

“…I looked it over very carefully, scrambled halfway up the route on the left and looked at the holds. I saw what sorts of moves I would be responsible for, if I were willing to commit myself to the climb… I went back to the base and started to devise ways, around the gym, in which to train for some of the difficult moves that I would have to do on the Thimble. I did all sorts of peculiar things that made a lot of people working out in the gym hysterical… I did squeeze-type exercises, because I noticed that there were some little nubbins up there that I would have to squeeze when the horizontal holds ran out… I trained for a period of one winter. The Thimble was on my mind during that whole time.”

This was the kind of effortful preparation and long-term planning by which Gill earned himself the flow states he so dearly valued as a climber. As he reflects elsewhere in the same interview: “Applying your intellect to problems, thinking about them, is actually an intermediate step in the development of technique in climbing. You want to reach a point where it fits together in your subconscious, and then you climb it instinctively.”

Gill equally exemplified the builder’s mindset in his math career, and in how he integrated these two major life projects. Quoting again from the Master of Rock interview:

“At the end of three years [as a university math instructor with a Master’s degree], I really felt that if I wanted to progress professionally I’d have to acquire a PhD. So I looked around and tried to find a school which was reasonably good at the doctoral level of mathematics. It didn’t have to be Yale or Harvard, but a reasonably good school that was near a very nice area with good boulders, hiking, swimming, fishing, and all the rest.”

This is what it sounds like to design one’s own success criteria from first principles, with the laws of nature and the requirements of one’s fully-lived life as the only constraints.

This is a more ambitious design process than our conventional views of “ambition” permit. It does not optimize for metrics like prestige or wealth as ends-in-themselves. But nor does it eschew “prosaic” considerations, such as the need to make a living.

By the same token, Gill did not develop his bouldering approach so he could secure a legacy and transform the sport for future generations (an ambition he did not form until much later). He developed it so he could get the kind of exercise and explore the kind of terrain that interested him.

This is exactly the sort of private, personal motivation that drove many of the creative and ingenious solutions we now take for granted. And it’s the sort that will drive whatever solutions we might build today, aided perhaps by the physical and spiritual uplift of our latest trip to the climbing gym.

First off, you’ll be pleased to know I’m high-minded enough to forgive you for showering Matt’s cringe-inducing puff piece about me with the most “likes” and views of any Psychology of Ambition post to date. It’s ok, two can play this game: just wait ‘till you read the dedication in my forthcoming book.

Second, a heads-up that I’ll be in SF from April 16-24, so reach out if you’re in the Bay Area and want to grab coffee. And if you’re a founder, VC, or founder-adjacent person, I invite you to join my fireside chat on founder psychology with two seasoned founder/VCs on Thursday, April 17.

Lastly, while I stumble through the dense, overgrown thickets of verbiage that somehow need to get shaped into a complete book draft by June 1, I hope you’ll enjoy this story of a fellow Penguin author (hah!) who did his own share of stumbling before his first manuscript took shape. You may recognize this spotlight from the inaugural installment of the Fantastic Builders series, where it was originally featured.

Builder spotlight: David Allen

Principle on display: Building yourself by building; why builders need self-trust (and how to build it)

Many people have positively shaped my life, but there’s only a handful—maybe 3 or 4 among those still living—whose ideas have fundamentally transformed my life for the better. David Allen, the creator of the Getting Things Done (GTD) system I was lucky enough to discover back in college, is among that handful. Beyond the many well-documented wellbeing and productivity benefits of GTD, its most personally meaningful benefit was its role in helping me build and maintain self-trust. By providing a reliable method for capturing and tracking our intentions and choosing whether, when, and how we want to act on them, GTD makes it both harder and less necessary to BS ourselves about what we intend to do.

And so you can imagine my barely-containable delight when I got to spend 30 minutes picking David’s brain in a 1:1 Zoom call the other day. (Thanks for making the intro, !)

David spoke, and listened, with the easy manner of someone who’s living his best life and knows it, and so feels no need to prove anything to anyone. You’d never guess from his mental spryness and casual demeanor that he’s either a day over 60 (he’s 78) nor the legendary author whose work has transformed how millions of people and organizations around the world relate to their work.

Here are some tidbits he shared about his backstory and how he went from being penniless and hospitalized for heroin addiction (a story you can read more about in this Wired piece) to becoming the world’s most sought-after productivity expert and executive coach:

For all the immense success David has enjoyed as a result of Getting Things Done, he never actually set out with any sort of “grand plan” of transforming how people work or achieving any sort of large-scale influence. “I’ve never been that entrepreneurial,” he said; rather he’s always experienced himself as “just putting one foot in front of the other.” For instance, after the “self-exploration” journey that led him to drop out of his UC Berkeley PhD program, take up heroin, and eventually hit rock bottom, David needed to pay the bills somehow. So he started taking odd jobs wherever he could find them. One of his first jobs, he recalled, was driving a delivery truck for a company making small industrial tools for some of the first “startups” in what eventually became Silicon Valley.

Some of David’s friends at the time were starting their own small businesses, and they needed help “managing their systems”—i.e., getting themselves organized. David was always “Mr. Lazy” (his words) and liked the idea of making things more efficient. So he’d spend some time helping one friend get organized, then he’d “get bored, move on, and find another job,” and so on. At some point he learned that the types of jobs he was doing were called “consulting” (not a category he’d ever encountered growing up in Louisiana), and that he could get hired to do more of them. Then “some corporate guy saw” what David was doing for these small business executives and said “we need this for our whole team,” so he asked David to do a training for his company, which then got picked up by other companies, including Lockheed, where it became “one of their most popular trainings.”

“Who’d have thought I’d end up in the corporate world?”, David mused. Consulting eventually turned into coaching for top executives, who would hire him to come to their office, sit desk-side with them, and help them implement the system he had come up with. It was 20 years later that someone said to him, “David, you’ve gotta write the book.” And it was another 4 years before he’d gotten the book written and “out of his head,” with little expectation as to how it would sell.

The rest, as they say, is history.

If you need a free and easy GTD start guide, by the way, Tyler DeVries has written a good one.

Builder spotlight: Celine Halioua

Principles on display: Your life as the yardstick; finding person-life fit

, the 30-year-old firebrand founder and CEO of Loyal, is one of the purest examples of practical idealism that I’ve ever had the pleasure to encounter. Her long-term ambition is to increase the human lifespan through anti-aging drugs. This is notoriously hard for a million different reasons, some of them regulatory (the FDA doesn’t like approving experimental drugs for non-disease targets), some economic and structural (e.g., it takes 20-30 years to see if a human anti-aging drug is working). But instead of giving up or getting cynical, Celine found an ingenious path forward: start by extending the lifespan of dogs, and establish a precedent for the human use case from there. 

Whenever I hear Celine speak, her boundless energy and optimism belie the enormous complexity and multi-decade time horizon of the mission she’s taken on. How does she do it? And how does she stay so cheerfully patient through all the regulatory and bureaucratic hurdles that have forced her onto this circuitous path to begin with? 

The simple answer is that this path has been anything but “forced” on her; she chose it. Indeed, she custom-crafted it, based on the sum total of her values and proclivities. During the talk she mentioned that she happens to be a dog lover, and afterward I asked her whether she would’ve been able to sustain the same excitement about this path if she hadn’t been. “No,” she said, after a moment’s reflection. “I’ve actually come to love dogs and dog owners even more since I started this,” she continued, smiling with delight as she described her conversations with prospective customers and the lengths to which they’re willing to go for the chance of a few extra years with their beloved pet. 

This is the big secret behind Celine’s seemingly infinite reservoir of energy and enthusiasm: she has charted a path that she can love, with her own life as the ultimate yardstick.

Builder’s Spotlight: Henrik Karlsson

Principles on display: Raising your psychological ceiling, Your life as the yardstick, build yourself by building, Worrying on schedule

When I stumbled into Escaping Flatland author ’s note about how he “decided to be more ambitious” with his writing and parenting—and his subsequent note thanking himself for that decision a year later—I had half a mind to just republish that original note verbatim, so emblematic is it of the kind of story I like to spotlight in this series. But then I realized it would be way more fun to get to talk to him about it, so I reached out for a conversation.

And what a conversation! Of all the many impressive people I’ve interviewed for this type of spotlight, Henrik left the most lasting epistemic imprint, so to speak: almost 2 weeks later, I can still hear certain fragments echoing in my head and shaping how I talk myself through writer’s block, how I think about life design for myself and my clients, what I give myself time to explore and digest (including of Henrik’s own essays!) even if I don’t yet have a tangible outcome in mind.

Below are some of those fragments, together with some exposition to put them in biographical and psychological context (with thanks to Matt for extracting an orderly narrative from the meandering chaos of the original transcript).

Henrik’s narrative of his career as a writer is roughly as follows:

• A period of significant conventional success in his youth that he ultimately did not like

• “Seven years in a desert”, where he did miscellaneous things to make ends meet, and, most importantly, where he wrote strictly and only for himself

• The present, where he is making a living writing weird (and wonderful) essays

There are also as-yet unwritten future phases, in which he envisions being ever-weirder and more ambitious—books, large scale artistic collaborations, operas, films.

Seven years in a desert

Henrik had an unusual amount of early success as a young writer. But it was a success that that had hard limits. He increasingly felt himself encountering groupthink, and pushing into writing territory to which his audience and publishers reacted negatively. “It made it hard for me to stay connected to my curiosity,” he told me.

So he quit.

The story of my life is a lot of these very hard decisions. The decision of, like, I had a book deal, and I did a guest lecture at Harvard which was very alluring to my ego at the time. I had a very good career for a 23-year-old-poet, yeah? The decision was: blow that up because of principles. And doing that again and again.

For seven years, he did other things. He worked as a programmer, he ran an art gallery, he had children. But through it all, he was, privately and intentionally, developing himself as a writer.

“I got so sick of the publishing world, I thought I would never publish anything, so I was just writing for myself,” Henrik told me.

But it wasn’t out of general misanthropy; he was missing something.

He calls this seven-year period his “years in the desert.”

I think the years in the desert were super important, of just doing stuff for myself without compromise for seven years. You see that in the stories of a lot of people who do creative work, that they have years in the desert where they learn to trust themselves, to keep going to amuse themselves.

There is a very peculiar thing that happens when there is no expectation. You’re not even trying to get published. You're just writing things for yourself. And if you do that for years, the writing starts to change. You’re starting to develop some kind of taste that is totally unaffected by expectations of what is fundable—or anything at all.

And that also takes a long time. It’s running the kind of loss function of your mind until you figure out what it is you’re doing. I just needed a long time to figure things out, to unlearn all the things about how writing should look, and what is doable and not doable. And also building up skill, because—I was quite skilled, I could do the established things, but I had this feeling for another thing I wanted to do, but I didn't have the tools to do it.

It was a question of both: figuring out what is this other thing, and that I could only do by running hundreds and hundreds of experiments, and also gradually building up the tools to do that thing.

He had many interests in this time, most especially in education. The writing was coextensive with thinking about his parenting. In discussion with his wife, Johanna, he concluded from first principles that homeschooling was best for their children, but in Sweden, where he had lived his entire life, homeschooling is illegal. (He also had to deprogram himself from the cultural default he had internalized, that homeschooling is child abuse.) This thinking led him to another excruciatingly hard decision: that he and his family needed to leave Sweden and build an entirely new life on “a small island in the Baltic sea.”

Shortly thereafter, perhaps emboldened by the experiences of navigating and even thriving in the wake of these prior “hard decisions,” Henrik began to experiment with posting some of his writing online.

“There was also that longing for a community and belonging somewhere. But I thought that was totally impossible, because the weird combination of the things I wanted to do didn’t fit anywhere.”

At first he had “no signal whatsoever” from any audience except for his wife. And he even “deeply internalized that no one’s ever going to care about this. I had plenty of time to build up those habits of thought.”

When you’re doing something strange, there's no signal until there’s signal. If you're going into a pre-existing scene or pre-existing genre or something, there’s going to be signal. There’s going to be systems in place to move you along. But if you’re trying to stitch together like some kind of genre that will hold your voice, there will be no signal of whether you are making progress or not.

Finding signal

But Henrik did start to get glimmers of signal. His social graph was changing, and he was meeting people online who saw talent in Henrik and encouraged him to be vastly more ambitious. He started dipping his toes in the water more—he started a blog, he posted on LessWrong, he followed and engaged with interesting people on Reddit.

From there, I got in contact with some people who directed me to subreddits and so on. So I started to get some people who would see some potential in what I was doing and who were guiding me. They’re like, “Oh, you’re almost where you should be, but you should go over there.”

The internet proved connective. He found other young writers who gave him community, and others who effectively functioned as talent scouts for him.

A surprising number of these very unknown people became quite successful later. For example, Tracing Woodgrains. I think I met him very, very early on, when he was just writing comments on Reddit. There was him and there were a few others who were just totally unknown at the time, and have gone on and done things in parallel.

I remember at one point there was an early reader who I started talking to, and he explained to me how to write cold emails to people. And I was like, “Can you send me exactly what you wrote?” I used that to write to José Luis Ricón Fernández de la Puente, who writes Nintil, and he put one of my essays on his link list, and so on so. So there were people like José who helped to accelerate things, put me on the map a little bit.

It was still like a very slow first year there. But there was a process of some people coming in, and these people who have very exceptional taste and are extremely online. There were some people like that who I guess in some sense are scouting. These are VC type people. Some of them are actual VCs, but some of them are more like VCs for culture, but they are looking for new talent and giving them nudges and so on.

Importantly, the signal that he kept getting was: be weird. Be more yourself. Do more of the things that are off script.

I realized, I think that I’m good and disciplined enough that I can do this weird other thing and actually still pull it off. I’m getting some signal from that, from people I trust. I’m assuming they’re ahead of the curve. And if I just put in the hours and do the work, I could actually do that thing.

The belief that he could do it came partly from the fact that Henrik was getting signal from people he admired. And it also helped that the kind of people he admired and interacted with, the kind of people who responded to his writing, tended to be in the orbit of San Francisco culture. A core part of that culture: be more ambitious. Don’t underestimate yourself. You can do way more than you think you can.

And there’s a very different mentality than the small island life where I live. You get a lot of this very nice American thing where it’s like: you totally underestimate what you could do. To have people who have really good judgment tell you that—it’s just like, oh, yeah. Then I’m like, I trust your judgment more than mine.

Growth was slow in the first year. Henrik had 30 subscribers to his Substack when he wrote The Learning System. It didn’t explode, in Henrik’s words, but “that’s when the weird internet nerds found me—very high signal on the people who found me on that post.”

Henrik shifted his lifestyle to be able to write more. As he developed competencies and had material success in his non-writing work, he would “spend” that capital, both the literal monetary capital and his increased credibility with his employer, on working less and writing more. (More on that in Henrik’s essay: 6 lessons I learned working at an art gallery.)

What I did concretely was that I gradually lowered the amount of hours I worked. For the last two years, I’ve worked 20 hours a week whenever I wanted to write. That was my deal. Like, I traded all of my increased income toward just having more and more ridiculous demands on my employer. By being more agentic, I became so valuable to them that I could have these ridiculous demands, and that meant I could write.

Now—as of a few months ago, and two years after finding his first glimmer of signal—he can support himself and his family solely with his writing.

Ambition in all things

Since I’m writing a book on the psychology of ambition, I asked Henrik about whether his ambition in writing—his gradually changing belief that more no-compromise success was possible to him in writing—affected other areas of his life. His answer was an unambiguous “yes”.

Wait a minute, if my understanding of what is possible in writing and what I can do is so flawed, and it’s actually like 100x bigger what I can do, then that is probably true of parenting, too, and it’s probably true of all of the aspects of the things I care about.

Parenting was one obvious major domain. But it really was everything that mattered to him. “It was my exercise and my diet. And having a better diet makes me a better father. All these things are connected.”

I'm in this flywheel right now where I'm, like, getting better at things, and I'm using those resources to help me do better things. Concretely: I was able to stop working three months ago, and then I could channel that extra time into better diet and more exercise—so I can have more stamina writing. Hopefully that means I earn more money now. There’s this flywheel of getting more resources to spend more, be more ambitious around the things I care about.

It’s also notable that the form of Henrik’s ambitions is incredibly unique. He draws from the general sense of ambition in San Francisco while rejecting, at least for himself, its most common specific manifestations—e.g. growing his user base (audience) by 100x, or turning that into capital.

I have this sense in my head that I want to make something really big, much bigger than I had thought. Previously I thought that maybe I could one day publish a book, and now I’m thinking on a much grander scale than that.

That I got from the San Francisco people, in a way. But to me, it’s even more ambitious. I’m going to do that with both of my hands behind my back. I’m going to do it the hard way. I’m not going to compromise on the super weird things that I want to do, but I’m going to figure out the way of doing it at the scale that they’re talking about. To me, that’s, like, doubly ambitious.

Henrik also had unorthodox advice for people who haven’t yet built their own flywheel on their creative projects: consider separating into two phases the (1) tackling and refining your interior world and (2) development of competencies to deal with the external world.

You have to have two maps. You have to have a map of your interiority, and you have to have a map of the external world. And both of those are going to be terribly wrong by the time you’re 20, and I think trying to do both at the same time, for me, it’s just not going to work. I think it’s much easier, if you should just make a dividing line.

So—if you want to be more ambitious, right? So during the years in the desert, I was starting companies, and I’ve been running an art gallery, and I’ve been agentic there, and I’ve all the skills I’ve learned there. I was only trying to pay my bills, but I was gradually becoming better and better at doing that. I leveled up my skills at doing ambitious projects by understanding the external world kind of separately.

And [meanwhile] I was just trying to indulge myself and trying to figure out the internal map. Doing those two things separately, to sharpen both of those knives.

You need to have both an extremely deep connection to yourself and also be just like, “Okay, I've moved to Thailand, and I need to figure out the tax code, and I need to do it in two days, and I can do that, and I need to find the best helicopter pilot in Bangkok today.” You need to be able to do those things. But you can practice those things separately.

And whatever you learn there you can use over here. I was just reading the biography of Philip Glass, or his memoirs. He’s starting companies all the time when he’s young, like he’s starting a plumbing company, he’s starting a moving company, he’s doing taxi work. That is super useful for him when he’s making operas later.

Once, he becomes a famous composer, like he’s really good at negotiating, he owns all of the rights himself and runs his own publishing company. Because he’s already had four companies, and he knows how to negotiate. So once he gets to operas, he’s like, “Yeah, I’m not going to do the normal contracts, I want better pay and I keep the rights.” Because he’s done that at plumbing companies.

4 days to do whatever you want, 3 days to be “evil to yourself”

Towards the end of our conversation, I selfishly asked Henrik about his writing process.

How much of his writing makes it through to publication? He ballparked it at 10%. “90% of what I write, no one ever sees.” It’s mostly exploration, free-writing, pre-draft of any specific essay. Henrik still writes a great deal that is, in effect, for no one but himself. What about once he starts putting together material to form a specific essay? “Even when I get to a first draft, only like 50% of that gets published.”

Henrik divides his seven day week in half: 4 days and 3 days.

I do four days of the week which are total self-indulgence. My only job during those four days is to get up, get to work early in the morning, and to sit down and I ask myself: what is going on in my mind right now? What am I excited about? And my only job is to think about that. I do that for four days in a row.

Usually what happens at the end of that is that I have three half essays. That just totally unblocks me, because then I just be like, “Today, I just want to learn about grammar.” It’s just totally random things.

This is, not incidentally, his cure for writer’s block.

I try to not censor myself at all. The reason I get blocked is because I'm thinking, “Oh, this. The people aren’t going to like this a lot.” You have to separate those two things. So, yeah, I need to have a phase where I'm just totally crazy. I just trust my intuition 100% percent…

The other three days go towards sifting through the raw material generated during the first four days, and crafting essays designed to be read by an audience.

I have three days a week where I'm like, “Okay, I need to pay the bills. What in this mess could I present in a way that is meaningful to other people?” And then I take the thing that I can workshop into something that I can ship.

The fact that he gives the part of himself that is worried about money three days a week is also psychologically important to his creative process. Designating a stretch of time for that part of himself allows him to ignore it when he needs to be more freeform and exploratory.

The parts of me that are worried, they know that there will be three days where they are allowed to be totally evil toward me if they need to get work done. “Right now, I might just be following my curiosity, but you’re going to be allowed to be as evil toward yourself as you want you on Monday. There’s three days when you can just spank me all day long.” And then that part of me says, “Okay. I’ll sharpen my knives until Monday then.”

And there you have it, friends: a cutting metaphor for the very essence of the builder’s mindset, as applied to the intentional management of one’s own psychology. Thanks again, Henrik—my wanting-to-get-lost-in-cool-people’s-biographies part and my needing-to-meet-a-book-deadline part both really needed that.

Builder’s Spotlight: Blake Scholl

Principles on display: Be intellectually ambitious, practice cognitive integrity, build yourself by building

My friend Blake Scholl has been in the news because of his company’s successful supersonic test flight—the first-ever supersonic flight of a privately developed jet.

Blake himself has also raised some eyebrows. “This guy pivoted into aerospace from Groupon?” Yes. But his builder’s story is richer than that.

Blake is a paragon of cognitive agency, of a builder breaking standard molds regarding his own thinking and knowledge. His vast ambition is grounded in rigorous epistemics.

Blake made an earnest inquiry into the reasons why supersonic couldn’t work; and when he found no good reasons, he started Boom. He trusted himself to start from scratch, in terms of both his network, his knowledge, and his expertise—he knew no one in the industry, had never worked in aerospace, and taught himself high school physics and calculus with YouTube videos in his first year at Boom.

He knew he would have to grow along with his company as he built it, rather than as a precursor to building it—and that this would further increase the already insanely high risk that it would fail. He chose to work on it anyway; not in naive denial of how excruciatingly hard and uncertain it would be, but in honest recognition that it was the thing he was most personally motivated to work on, risk and hardship notwithstanding. 

Here are the most relevant highlights from my conversation with him a little over a year ago. All quotes are from Blake.

A dream of supersonic, a life in e-commerce

Blake was always interested in supersonic. But he had never worked in the space. He worked in ecommerce.

In my mid-20s, I set a lifetime goal of breaking the sound barrier and I put a Google alert on supersonic jet, so I could be first to know when I could buy a ticket, but it was crickets. Meanwhile, I was having my first career in tech, worked at Amazon when my family thought it was a bookstore…

I thought, “Okay, I know mobile, so what should I work on? I should work on mobile e-commerce.” I started this mobile e-commerce company that built basically a barcode scanning game that was intended for people who would shop in stores.

Blake was working insanely hard, but he wasn’t actually that interested in the project. So he took the first reasonable out.

What I found was that it was like any startup that was really hard, except I would get up in the morning and think, “Why in the world did I get into this? I’m working really hard. I’m really worried about failing. I’m worried I’m going to lose all the investors’ money and let my friends and employees down, and let myself down and I'm thinking it’s not even worth it.”

When we had an opportunity to sell the company in a way that everyone would make a bit of money in a small exit, it was a massive relief to me. I thought, “Great, take the exit. Stop having to worry about failure, live to found another day.”

He ended up at Groupon.

I got to spend two years at Groupon retaining the bank account and reflecting on what I had learned. A joke I often make is there's nothing like working on internet coupons to make you yearn to work on something you really love.

Forging the steelman against supersonic, defeating it

He wanted to do another startup, and decided to make a list of everything that he would be personally motivated to work on, “forgetting everything else”—including “is it physically possible”, “do I have the resume for it”, and even “is it a good idea”.

He started looking into supersonic flight, at the top of his list, figuring it was a no-go. The opposite occurred: it turned out none of the reasons to not do it were good.

I figured, “I will probably get two weeks into the research and then I will understand why it's a bad idea, and no one's doing it and I will move on. I'll move to the next far more plausible idea.”

But instead, what I found was that there was a whole bunch of stale conventional wisdom about why this wasn't possible that didn't stand up to careful analysis, that anybody with a spreadsheet and half a brain could do with data that could be found in Wikipedia. You don't have to be a rocket scientist to look at it, you just have to look.

And so I continued to turn over more cards, and every time I turned over a card it was like, “No, this is plausible. This is plausible.” I spent basically a year from when I left Groupon to when I hired my first employee at Boom, really just getting educated, actually reading those books I bought. Took an airplane design class, built a spreadsheet model of the airplane, started to meet people in the industry.

Starting from scratch

Blake was starting from scratch. Truly.

On day one, I didn't know a single person in aerospace. I had no network, I had to build all that from scratch.

He also built his knowledge from scratch.

In that first year on Boom, I took Khan Academy remedial physics because I didn’t think I actually understood it. Same thing, calculus. I hadn’t had a calculus class since high school, and I wasn’t sure I actually had ever understood it. It felt wrong to have to do those things. It felt like I should have known them, but the truth is I didn’t.

Taking confusion by the horns

How Blake thinks about these seemingly showstopping deficits actually indicates a unique strength of his: the willingness to be shamelessly confused, and the relentless clarity that he imposed on his confusion.

I kept a confusion list, meaning when I felt confused about something I’d write it down. I had a goal of taking one thing off the confusion list every week. I think I had in my head initially the idea that that list would one day become empty, but no, it actually it only gets clear every week. But what it did have for me is self-awareness about what I was and was not clear on. That turned out to be super valuable.

Confusion versus clarity and not accepting confusion if it’s something really important, that would be lesson one.  Lesson two is about thinking in terms of first principles. I think again, we tend to get taught that if we're really smart then we handle complex things and subtle things.

I think the opposite is true. I think the real wisdom is in very simple, basic understanding. One of the advantages in coming to a new domain into my career, I didn't have four years to go get a four-year degree in aerospace.

Embracing and self-authoring the new entrant narrative

Blake understood that being a new entrant mattered. More than simply understanding it, he fully narrativized and romanticized being a new entrant. In his words:

When I was wrestling with whether to start Boom, one of the exercises I did was say, Okay. Let me get my own ego and insecurity out of this. Let's imagine the year is 2050 and I'm sitting on the beach, sipping Mai Tais, and reading about aviation history.

First off, do I still think we're flying around at 80% of the speed of sound, or do I think we've gotten to supersonic? I sure as hell hope we're going supersonic now. Okay, great. How did that happen? How do I think that history reads? Do I think after 150 years of not doing it, Boeing did it? Yeah, probably not. History doesn't go like that. It was probably a new entrant.

Okay, what would that new entrant look like? Well, they’d probably be from outside the industry because everybody who grew up in the industry, would’ve learned all the lessons about why it can’t be done, so it's going to be an outsider. Okay, great. What would the outside effort have to look like? …

I could keep going, but my point is I was able to take myself out of it. Imagine what a success story would have to be like. Then it's like, “Okay, turn that around, go become that.” What I've found is that working backwards, reverse historical reasoning has provided an ever-present view of what are the things that are going to really matter.

There were tons of other insights—including on how to think about seemingly intractable problems like traffic, how to pick personally motivating problems (as opposed to problems on whose importance there is banal universal consensus), how he thinks about personal growth and leveling up, and much more. Again, check out the full transcript.

In the 18 months or so since this interview, Blake has led Boom through a number of milestones, most notably achieving private supersonic flight. The amount of thoughtful innovation this has required—from aircraft material to jet engine design to cockpit layout to AR landing systems—is a testament to the power of the ambitious epistemics that are Blake’s distinct strength.

See my Intellectual humility is a cop-out, Vision vs delusion, and The best way to build yourself is by building for broader takes on Blake’s virtues highlighted here.

Welcome to today’s installment of “Fantastic Builders and Where to Find Them.”

Builder Spotlight: Nicole Ruiz

Principles on display: radical agency; your life as the measure of all things; be intellectually ambitious; we build ourselves by building

Nicole Ruiz is a community builder. She’s a full-time mother who hosts dinner parties, who gets to know her neighbors, and who keeps an informal social CRM on local people. In a world where people complain about fragmentation and isolation, where people leave the house less, where child-raising villages are the exception rather than the rule—Nicole is quietly building these things for herself.

Her path to this point is a classic case of Steve Jobs’ “You can't connect the dots looking forward; you can only connect them looking backwards.” Even looking backwards, it looks less like a carefully charted course, and more like a dance with serendipity. A dance of striking complexity and skill, no less, which Nicole has continuously honed in the context of ever more stimulating and demanding dance partners. (I was lucky enough to hear Nicole tell her story while her unbelievably cute toddler was playing next to her and occasionally inquiring about yogurt or Amtrak trains.)

Growing up in Fairfax, Virginia, Nicole benefited from having a high bar of intellectual inquiry set in her K12 education. She went to Trinity Christian School, which was rooted in a classical education approach and emphasized “learning how to learn,” as Nicole recalled. For example, one of her senior year assignments was to write a thesis explicating her “worldview” and what she was “called to in the world”:

We had to defend that thesis in front of a board of adults. And you had to interview people in specific careers. So I interviewed somebody at Google who was working on their machine learning team.

More than that, Trinity had the killer combination of highly invested teachers and a liberal arts approach:

I would also say so many of the teachers just really cared about the students. In fourth grade, I did a Girls on the Run 5k with one of my teachers. My parents were like, “Don't ask your teacher. That's so embarrassing.” But my teacher said, “I would love to do that with you.” We stayed in touch for years.

That education was very formative for me, and I think set a really high bar. They also talked a lot about the life of the mind. There’s a richness that the liberal arts lends to your life and to your world…. You kind of have this perception [that] the life of the mind is woven through your world at large.

This idea of building a “life of the mind” really stuck with her, and gave her a deeper, more expansive view of what constituted a good life: not the accumulation of some narrow set of credentials or job titles, per se, but rather an intellectually curious, independent-minded, community-driven orientation that infuses all your projects and decisions.

This, along with a volatile family situation requiring her to make her own way after high school, motivated what ended up being a very atypical path through higher education, into her career, and, ultimately, back out of her career.

Nicole’s experiences of higher education included several stints at community college, a 1-semester stint at Liberty University (before dropping out in bitter disappointment), and a data science certificate program at Lambda School (from which she also dropped out). All of these experiences left her wanting for the intellectual stimulation and “life-of-the-mind” atmosphere she had learned to expect at Trinity.

So she turned to the internet, specifically Twitter, to fulfill those needs. She had been on Twitter since high school, but now she started to post a lot more, sharing ideas and articles related to her burgeoning interests in medical research and machine learning.

The time that most people spend hanging out with college friends, Nicole spent hanging out with Twitter mutuals, particularly from the post-rationalist Twitter scene. Buoyed by those initial connections, she started “trying to throw myself into more things on the internet that were interesting,” which led her to get some scholarships to attend scientific and engineering conferences that she was interested in. When she attended conferences, she networked and took notes and asked questions, which in turn led to work opportunities:

I used to also go to events and just take notes like crazy. I kept them if I thought the speaker was really interesting, so that I could message the speaker. Just to prove that I was competent and paying attention.

I would also try to ask questions that made me visible to both the speakers and other attendees. I think more people spoke with me at events like these because it was easy to follow up on the public questions I raised my hand to ask.

One time I was in some lecture at the Google offices in DC, and I was taking really intense notes, and one of the people from that group came up to me afterwards and just started chatting. He was like, I like your notes. What did you write down? What did you think? And we started talking, and they were like, do you want to work on this project?

Nicole did a fair amount of work during this period in data-driven medical research. And she did even more ad hoc learning as well, crashing her friends’ lecture courses at Georgetown or UChicago and talking to the professor afterwards. She noticed how easy it was. “Nobody cared” that she wasn’t enrolled. “You could literally go up to the professor and be like, I sat in on your class. I have these questions. And they were like, ‘That's awesome. What did you think?’”

In the midst of all this very-cobbled-together college-level education, it was her Twitter habit that kickstarted her career.

I was in the middle of the Lambda School boot camp, and I was tweeting, should I work at a FAANG [big tech] company? I was still really interested in machine learning and health care. And so [the man who would become] my boss, Michael Dempsey, who [was then] the GP at Compound, the VC firm, ended up reaching out to me and just DMing me. He said, “Don't go work for a FAANG company. That's a horrible decision. It's going to kill your creativity. And have you thought about VC?” And then we jumped on a call, and that's how everything progressed… They were very open to me proving my grit through the application process and proving how fast I could learn, and I ended up getting hired.

He had followed me for a while, and I loved his tweets on technology. For a long time I would post: machine learning paper, machine learning paper, here's my prediction for how companies will adopt this. And then I would link when whoever it was, Microsoft, Google, whatever big company would follow up and do something that I thought was a confirmation or was otherwise related to the research I had posted. Michael would interact with those occasionally. But that was really all the context we had.

By doing her very Nicole-ish dance of sharing her notes on Twitter, Nicole had in effect created a public resume of time-stamped, provably accurate bets on the commercial potential of emerging AI technologies. This is the kind of track record that a VC firm can usually only dream of when vetting a young candidate.

Nicole worked as a VC, intensely, for 3 years. She loved it. It was the culmination of years of the sort of high-agency networking and learning-in-public that so often characterizes builders’ paths today.

But in the background, another arc was progressing. Nicole had been dating Santi, a friend she had met in high school, through their respective college and early career experiences. Now they were both in New York, they had gotten married, and they wanted children.

At first Nicole just figured she’d do what almost everyone in her position does: keep working.

I really, really, really loved being a VC. It is just super fun. It's being knee deep in a ton of research with a ton of people who are so much smarter than you, and they're telling you about what they do. It's very exhilarating, very people driven. So I really wanted to keep doing it.

But, on further reflection—and in conversation with Santi, who was open to a big family pivot—she changed her mind.

I had the realization that both of these things were going to require a lot of time for me. VC kind of necessarily expects you to be the person who can be on call for a founder at least some amount of the time, and I also would probably be that person for my son. I could take a step back [rather than quit altogether], but it would just look like a very different thing. And it had been a few years of 80 plus hour work weeks.

And the realization kind of hit me, and Santi was like, “Okay, that’s what you want? Awesome. We'll try that.”

The big, sudden change was dizzying at first. But the level of grace and intentionality with which Nicole stepped into her new homemaker role was characteristic of the rest of her life. She first had to figure out the footwork from scratch. “My mom worked for the majority if not all of my childhood, so being a stay-at-home mom or homemaker wasn't something I'd considered,” she told me. “I was like: ‘I guess I'm here now. What does that mean? Is this something I can get good at? I guess so?’”

Nicole found continuity through the change. “Your identity shifts so intensely, but you can also redirect the skills that you have.” Initially she felt like she was spinning her wheels, but then she took up “investing in these skills of motherhood,” as she put it.

What does it look like to be good at this? It's not really something again, weirdly, that I'd ever thought about before…. What are my priorities? What are my values? What do I care about in forming [my son]?

It wasn’t easy for Nicole to figure out. “In New York, it was especially hard to find older people who had kids and could act as mentors. Not just people who are my age, but somebody who has raised a few kids and has some time under their belt and is less in the same stage of like, ‘Oh my gosh, this is overwhelming,’ and more like, ‘Okay, but it will all turn out fine.’”

But she did figure it out, and she recognized that this dance had a familiar beat:

There were parts of it that reminded me of startup world and tech world. “How do we take control of this problem with whatever resources we have? It's changing shape all the time. What's a typical way to solve the problem, or to get better at solving the problem, and develop systems around doing that.”

Part of it was finding structure for our days and trying to really stick to that. Part of it was trying to tease out my own priorities, which were things like finding ways for both of us to be outdoors together, finding both of us to have a really rich social community. What are the weird ways I can take advantage of this time in my life where I have a lot of time and a lot of flexibility, where he’s a big commitment, but it’s in spurts and stops.

Nicole started volunteering to help the homeless at a church at the end of her street. She worked at their social services desk, aiding individuals with benefits issues, entering rehab, finding housing, and general tech support. They were happy to show her the ropes and did not mind that her 2-year-old son tagged along. Even more wonderfully, the church served as a large indoor play space for her son while she worked, and much of the population that came through did not get to see many young kids and really enjoyed playing with him.

Nicole wanted to bring together different bits of competence from her community, so she started handing out “mom business cards” to people in her neighborhood who did things that might be of personal or community interest. She started “pitching” them and “tracking” them.

New Yorkers are funny because they're not necessarily super friendly. But I feel like when you make a weirdly specific pitch, they're very open to it. So sometimes you put out the conversational feelers, or even if you meet a mom—I do the thing, which I totally did during VC, which is just a ton of social management. I find somebody, I get their name, I put in two details about their life story. I do a ton of internet research, and then I'm like, oh, interesting. You expressed an interest in running, maybe we go running together in the neighborhood. Or, our kids should have a Spanish speaking playdate sometime. Or, could I use your backyard playspace occasionally for my son and I'll bring you some baked goods? Or, would you be open to giving four 3-year-olds a tour of your seltzer factory? Or, if I bring back 6 friends to your business, will you give us a discounted rate? But sometimes it's also just making a point to inquire after someone's health, or their trip, or if they need pet sitting.

I've talked about this on Twitter a little bit, but I keep my neighborhood CRM in Apple Notes. It’s my relationship management software. I just put the notes from everybody that I meet. Like, the block association president told me, “If you ever need real estate in the neighborhood for something, let me know.”

This is coupled with a great deal of active hosting, bringing into her home the kind of environment she wants for her family.

Looking ahead to the future, Nicole is already mentally choreographing her next big act, which centers on creating an excellent homeschool community for her kids:

I definitely aspire to some version of homeschooling like that, which is just employing all the fun and lovely and complex personalities of New York (or maybe not New York in five years), but pulling them into teaching with communities of families that we really love and enjoy spending time with.

She even mentioned getting some inspiration from her mother-in-law’s homeschooling methods, including an illustrative anecdote (relayed in a recent podcast interview) where dance literally became part of the curriculum:

I think he had originally been doing yard work for them, but they just got caught

up chatting. He's like, I also instruct salsa. So they move all the furniture to the side, and they pay him to teach a lesson.

Talking to Nicole, it is apparent how meaningful all of this is to her—how she’s linked it up to patterns of thought and values from across her life. The networking and social engineering, from Twitter through to VC, the scrappiness of how she built an educational community for herself as she is now starting to do for her son and for others—all of these moves connect into one flowing, magnificent, highly intentional dance. That dance is the embodiment of “the life of the mind,” realized in the singular personality and joyfully hyperconnected world of Nicole Ruiz.

Builder Spotlight: Jesse Genet

Principles on display: Earning our own trust via self-honesty; radical agency; the spiritual meaning of money; your life as the measure of all things

Jesse Genet is the paragon of an ambitious builder: in the sense of having built two awesome businesses, but also in the sense of being someone who intentionally builds her life and person.

I had the good fortune of meeting Jesse in San Francisco last July, when she and her family (who normally live in LA*) were living on their catamaran boat in the SF marina for the summer. It was a family meetup, with our husbands and collectively our five young children. The oldest was my 4-year-old, who prevailed upon Jesse and her husband to take us sailing around the Bay; the youngest was Jesse’s 6-month-old, who napped in the sun while we sailed:

As you’d expect, we spent much of our time talking about parenting and raising families. Spending time with Jesse was a pure joy for many reasons, but above all because she is so utterly sincere, and so completely comfortable with herself.

I didn’t realize until I spoke to her last week just how hard-earned this sincerity and comfort are for her.

Jesse was a teenage entrepreneur who—to the confusion and chagrin of her family—rushed high school, declined a full ride to a respected university, and moved to California to build a bootstrapped t-shirt printing business called Inkodye, dropping out of design school along the way. She wound down that company and started a new one, Lumi, this time venture-backed and poised for massive scale. And then she—to the confusion and chagrin of her investors—sold Lumi. And since then, she has—to the confusion and chagrin of those who see motherhood as low-status—mainly been spending time with her kids.

At every step, she had to muster the self-honesty and courage to make hard choices aligned with the life she really wanted to live. She had to be ambitious about her character to pursue her chosen forms of ambition without compromise, rather than get pressured or deluded into more socially acceptable forms.

Here are the highlights of her story; paid subscribers can access the full transcript below.

Bootstrapping ambition: How 16-year-old Jesse made herself into an entrepreneur

Growing up in suburban Detroit with parents who worked “fairly normal” jobs, Jesse nonetheless got her first glimpse into entrepreneurship at home:

My stepdad had his own businesses, and I got this small glimpse in my teenage life into, like: oh, instead of selecting a job from a drop-down menu, you can be an entrepreneur. You can just make something for yourself. And so I was fascinated by that and attracted to that.

When Jesse didn’t become captain of her high school cross country team, she decided that she was done with the school world and heading to the real world. She parlayed an interest in screen printing and photography into a business idea: printing on t-shirts. Since she didn’t have any money to speak of, she assembled her first screen printing setup by requesting all the parts she needed—like ink, etc—as birthday and Christmas gifts. From there, her entrepreneurial journey took an even more remarkable turn:

I was lucky enough to still have a dark room like in my high school, and I was fascinated with that process. I became convinced that you could do photographic printing on fabric instead of screen printing. And I went down this rabbit hole of learning about chemistry to try to find a dye that is permanent on fabric, that is also photo reactive.

She went to the library of a local college and started researching dyes. That research led her further down the “rabbit hole,” at the bottom of which was a 1950s dye formula, owned by an industrial paints company that was no longer operating, owned by an elderly man in Oakland. And that led her to:

• Accompany her step-father on a business trip to LA—which, in Jesse’s “teenage mind,” was close enough to Oakland (it’s a 400-mile drive)

• Meet the man with the derelict facilities for and rights to the dye, and convince him to sell them to her under a sort of seller financing arrangement wherein she would take over operations and somehow get him $50,000 in exchange, whether by selling his old equipment or otherwise

• Find a forgotten clause in her high school student handbook that allowed her to stop attending classes a year early, and convince her principal, guidance counselor, and parents to sign off on to the plan

• Move to LA without a definite plan for work or school

• Go into debt to attend design school while also flying back and forth from Oakland and staying in cheap motels to “run the operation” she had acquired from the old man

If this sounds dramatic, be assured that I am actually eliding some of the more incredible details (like communicating with the Oakland business owner only via snail-mailed letters and hashing out the deal at a McDonalds). She herself was caught up in the romanticism of it. She described her interest as “obsessive” and like a “freight train”—but also profoundly meaningful.

I think when you're young, like a teenager—and I try to grasp this sometimes still—there’s this feeling like there's hidden treasure all over the world. There was this feeling of mysticism and magic to this experience that I was really locked into.”

This gave teenage Jesse the gusto she needed to overcome the incredulity of her parents, who “micro-disowned [her] for a second” over the decision to forgo a full ride to the University of Michigan and move to California. Or her principal, who was impressed—impressed not as in “enthusiastic” or “encouraging” but as in “stunned”—by her efforts to get out of attending the last year of high school. But she was convinced that she was going to be an entrepreneur. And she was certain that photographic t-shirt printing was amazing:

“I found out that there was this formula in the 1950s that can print photography on fabric, and no one's using it! What's so funny to me looking back is, I'm not asking myself, what's the market size of people printing photography on fabric [such that] it exists and it's not happening? …I was very convinced this was so brilliant and so cool.”

And the thing is, she wasn’t wrong. Sure, Inkodye didn’t turn out to be a massive business opportunity (though it did, in fact, turn into a non-trivial one, with nearly $2 million in annual revenue at its peak!). But it was a legitimately innovative tool for doing something that Jesse and many other creative people like her wanted to be able to do. And, like so many innovative tools, it needed someone to make a serious project of it if it was ever to see the light of day. (Literally, in this case, as inkodye works partly through sun exposure.) Meanwhile 16-year-old Jesse needed just such a project on which to cut her teeth as an entrepreneur.

The final difficult step in her early journey was the decision to drop out of design school. She got a lot from college—most especially meeting Steph Ango, who would become her cofounder for Inkodye and for what would become her next venture.

But she was going into a lot of debt. And, for someone who was learning first-hand about making every dollar and cent count, who was having, as she put it, the “True Blue capitalist experiences of paying taxes, hiring employees, watching 30% of their paycheck go away, trying to make ends meet, trying to pay rent”, it was too much. She herself was living extremely cheaply and barely paying herself a salary.

Real life is so hard, and making a product valuable to people is so hard, I couldn’t believe I was writing checks to the school for like 20 grand. Like, it’s popcorn. Confetti money. It felt off.

So she dropped out, which, at the time, felt immensely scary. Going to college was the family tradition. Dropping out was a stigma.

These were hard decisions; she describes them as the hardest of her life.

Those were the hardest decisions, and I was very exposed to risk. I had a very subsistence level of support from my parents, which I still very much appreciate. But I was very lonely, and I didn't know anyone out here. It was very hard, very lonely. I wouldn't sugar coat it. Very hard.

Ambition begets ambition: Going big with Lumi

The difficulty was not without its rewards. Jesse, with the encouragement of her more internet-savvy cofounder Steph, used Kickstarter to raise $250,000—a shockingly high amount in those days. She got plugged into the maker movement, to a whole constellation of people doing DIY, direct-to-consumer crafts. She sold her fabric dye at Michaels and Urban Outfitters. She went on Shark Tank.

She did all of this with no investment, apart from the Kickstarter cash infusion. But because she was learning business from scratch, she didn’t know what to do with it. In hindsight, she thinks she could have sold the company—but she didn’t yet understand what this meant or how to do it. There were “two different arts and crafts companies that were very much sniffing around to try to buy the company,” Jesse told me.

And they actually would say explicit things to me. But I didn't know how to sell a company. They were trying to buy, and I didn't know how to sell, and so I put no good efforts into this.

Inkodye had several big sales years with the product of people just wanting to try it, almost voyeuristically. And then there was this really small subset of people who actually used it a lot. But that really wasn't enough to make a full product. In someone else's hand, the people [who] were trying to buy it from me—they probably could have done more with it.

It could have, Jesse told me, perhaps been like tie-dye—an enduring, seasonal craft, with a large spike in sales every summer. “But I didn't really know enough. So, long story short, I think I kind of blew it, and I didn't sell the company. I had to wind it down over time.”

Jesse and Steph’s second company, Lumi, emerged organically out of their experiences with the first. They were already networking with direct-to-consumer entrepreneurs, and knew the product space very well. One of the things they became known for was their packaging design. They knew many people who would prefer to focus on perfecting and selling a product, but who could benefit from exceptionally designed packaging. “Our packaging was very cool because we were designers,” Jesse recalled. So, she remembered thinking, “let's create a business that helps e-commerce entrepreneurs buy packaging more effectively, because it's so painful.”

Out of the gate, the experience was very different. “Shocker: selling packaging, which is a multi-, multi-billion dollar industry, has a little bit more legs than selling photographic fabric dye”, Jesse said.

We were able to raise venture money for it, because it's an actual market opportunity. And, of course, we're demonstrated entrepreneurs. We already had run this business that made money. We got into YC. And there was this transition from us being homegrown Kickstarter grassroots kind of entrepreneurs to going through YC, doing that whole adventure, learning about tech and really becoming like a tech entrepreneur.

Jesse found that she benefitted from reflection on these differences, and on how new everything was. The business was doing extremely well; she raised a seed round and a series A based on how well it was doing. But she had a lot of “psychological catching up to do”, as she put it.

A lot of it had to do with money, particularly the level of spend. The idea of spending, for example, $100,000 on a headhunter, seemed absurd to her. So did the salary demands of competent executives. She paid herself $50,000, minimized expenses, and was scrupulous about paying off her student loans. She was accustomed to the relatively folksy and finance-light world of maker culture. This was something different—not wrong, just different. “Sometimes I was holding the company back”, she said, recalling how she balked at paid versus organic advertisement. “Other times I was probably exercising great judgment, but… it was really hard to tell the difference.”

She also suffered from the usual amounts of imposter syndrome, managing seasoned technologists and executives while she herself was living in a trailer behind Lumi to avoid paying rent. Interestingly, she remembers the concrete event that allowed her to “crest over” the impostor syndrome:

When I finally got to $0, meaning I paid off my own debt, and then I was just earning income, and there was actually, like, $1,000 in my bank account… I felt so much more confident. Yeah, debt was truly contributing to my imposter syndrome by a lot, for me personally.

That positive balance in her bank account, and the financial autonomy it symbolized, had as much spiritual as material significance for her. She also came to realize, and has since coached other CEOs to realize, that it is important to “pay yourself a salary level that makes you feel okay, because otherwise you literally do resent everyone on your team.” Getting to a place where she “felt ok financially” removed some of her remaining internal roadblocks around money, and ultimately made her a better manager.

Things were going great. And then she came up against, in her terminology, an edge.

Choosing real over pretend ambition: Selling Lumi

What’s an edge? Jesse explained:

If everything is going literally like perfectly in your company, you never feel one, because the company is just literally growing and growing and growing. There's no feeling of edges to it.

But I do think there's a lot of businesses where you start to feel an edge. And it's not always falling off a cliff edge, but it's like, oh, I'm feeling the edge of my business idea, or the edge of my market, or I'm feeling like we are not going to keep growing the same way. If I don't do something radically new, I can't keep on the same course.

She started feeling this about Lumi. The business had a great start, and it was still going well. They were going to raise a series B round. Yet:

The direct-to-consumer sentiment was changing. The DTC businesses that were the core of our customer set were not always succeeding themselves, and so some of our customers were going out of business. And I noticed that trend.

She also noticed, with the prospective series B investors she respected most, that she couldn’t quite convince them. She did secure a term sheet, but the terms were “middling.” And she had the experience of giving her very best, most confident pitch to some great investors—and not being able to generate excitement. They had good, critical questions. They poked holes. They saw the same cracks she saw.

This was not the only signal, or even the main signal, but it was one of a number of signals that set her to thinking critically about the market situation for Lumi. And so she decided to forego the series B and to seek an acquisition instead.

She herself felt like she was doing something verboten. “We are coached in the startup ecosystem, at least, to never admit that, because everyone's building a multi-billion dollar business. If you say anything else, you lack ambition.” Her existing investors were shocked:

“The investors were like, ‘You got a term sheet? Take it, spend the next five years growing up.’ Because their math is much more like, give her more shots on goal. Maybe they'll figure it out.

There's a moment where I tell them I'm not going to raise a Series B. I have a couple conversations started about possibly partnering, or selling the company, and those conversations are either going to work out or they are not… And my investors were like, uh, what? Like, what are we talking about? Because the concept [of an] entrepreneur having any options available to them that they're not taking is anathema.

But Jesse knew, once again, that she was not served by accepting the notion of an anathema. Instead, she thought it through.

She knew from her first company that there was, in principle, such a thing as creating a product that was better as part of someone else’s business than it was as your business. It made some sense that packaging would be like this: they had made something with real value, but it would have more value in someone else’s portfolio and under someone else’s management. The flipside of this was that she knew there were lots of venture-backed companies that persisted, stuck, for years, falling short of their own aspirations.

I think if entrepreneurs are really honest with themselves, and you start to recognize that there's an edge to something, you need to ask yourself: am I the person who pushes past this edge and gets us onto the whole next course, or is this a time to partner or sell my company—because it's actually better, or will grow better as a feature of something or within an umbrella with different resources?

That self-honesty was key for Jesse. And it was painful. She analogized it in our conversation to giving up a child for adoption because you can no longer give it what it needs. And she was very clear with herself, even at the time, that she was the one who needed to make this call. The creator has a unique purview and unique responsibility with respect to the fate of her creation.

I was… the original motive force behind Lumi. And so it felt like my duty—no, it felt like I would be cowardly to make someone else do it. It felt more like it would be my cowardice to make my investors come to me and go, “I think, Jesse, we got a problem here. We're going to shut this business down.” Or to make my cofounder come to me and say, “I think [we should] sell the company.” It would have felt like I didn't act clearly. It was shirking the responsibility. I felt a deep responsibility to actually make this tough call so that everyone could point to me and go, “She decided.”

She got the clarity she needed and made her decision. In the end, she still had to put her foot down.

My investors were kind of shocked. I had never done something that they didn't approve of, really. So we had a very good relationship. They were very good investors, very respectful of me. And I remember it was the first and only time I ever said this to them.

I said: “At the end of the day, I believe that, as a CEO, this is my call, right?” And I actually had them be like, “Yeah.” And then I was like, “Then I'm making the call, despite you not liking it. I’m just double checking that you view it as part of my job as CEO.” And they were like, “Yes.” And I was like, “Then this is what's happening, and—no combativeness, but just checking—I'm a CEO still, right? You're not firing me, right? This is what I think we should do. I believe this is the best course of business.” And they were like, “Yep.”

Incidentally, Jesse made the decision to sell Lumi while pregnant with her second child. When I asked whether the pregnancy impacted her decision to sell, she reflected that it did so only indirectly, by sharpening her awareness of what was at stake:

I think it added to my self-awareness, like when I was having those calls and reading people's mood… I think it made me feel like, you know, time is very precious. I need to be very calculated with how I spend my time, how I spend my energy… It felt less reasonable to be delusional.”

So she negotiated a sale of Lumi. Her investors got a small return. Her team got job offers. The product continued to exist and add value for several years. Her cofounder went on to become CEO of a new company where he is flourishing. And, after some time with her acquirer, she decided it was time for a break.

Owning her ambition: A public embrace of full-time motherhood

A break felt natural and hard-earned. “I had been working non-stop, through all these entrepreneurial chapters, and I knew a break would be good for me,” Jesse told me.

At first, during her break, she felt the need to signal that she was thinking about her next project. “For a while I had all these terms, especially with my female friends and stuff, like, oh, I'm rethinking. I'm taking some time to rethink. I'm thinking about my next idea. There's all these things you say to make clear to people, like, you're not out of the game.”

And then at some point, she realized that “this was storytelling.”

There's a turning moment where, like… it’s not only a break. I knew I actually wanted to do this phase. And then there’s admitting that, like, it's not just a sabbatical.

An exogenous event—Jesse had a near-death experience with an ectopic pregnancy—accelerated this realization.

There’s something about a near death experience that is very clarifying. I started to realize that some of the narratives of what I would tell my female friends who are ambitious—"Oh, I'm thinking about my next idea, like, that's what I'm doing”—I sort of realized, this was a form of storytelling to convince people that I was still relevant.

I became better at detecting my own bullshit. I realized, after probably almost a year of telling people these types of things, it became clear to me that it was just something I was saying as opposed to being real. I asked myself: what if you just stop saying that? What if you just say, “I am really enjoying being with my kids.” And then I got pregnant again, and then I’m just momming, you know. And I'm like, I'll just stop. So then there’s a lack of bullshit.

But then in the vacuum of no bullshit, it’s like, what if I go one step further and I actually say out loud that I think more women might want to consider spending time with their little kids like that? It's actually really great.

Just like when she decided to move to California, or drop out of college, or sell Lumi, Jesse again felt like she was doing something verboten. And, just like all those other times—and with the experience and wisdom she had accrued through all those other times—she saw through the wall of bullshit, and was emboldened.

It’s not allowed speech in ambitious circles to say, “I actually think taking a break with these little kids or spending a lot of time with them is meaningful. I don't feel like I'm missing out on something. I feel like I could do career later.” So I decided, you know what, if there's any women out there feeling like they can't really talk like this, fuck it. I'll do it.

Conclusion: Self-honesty as the ambition enabler

Psychologically, Jesse’s life has been shaped by repeated acts of self-honesty. That’s not the only thing that has shaped it. There was also, of course, her burning interest in screen printing, her desire to be an entrepreneur, amazing people such as her cofounder and her husband, her love of her children, and more.

But a recurring enabler has been her ability to face tough situations by asking herself what she really wants, what she really thinks is true. It’s taking a moment to cut through the noise of social assumptions, of her own assumptions, and to look at reality fresh. It’s privileging curiosity over fear.

And that honesty has paid massive dividends, in her career and also in her character.

I’ll close the way I opened: spending time with Jesse and her family was the highlight of my summer. I am fortunate to have many people in my personal and professional circle who are living their best lives, but it’s rare to meet someone who is so obviously happy and at ease with that fact.

*Jesse and her family were among the roughly 90,000 people forced to evacuate their home last week due to the LA fires. When we spoke today, Jesse said their home is safe so far, and expressed appreciation for the literally life-saving efforts of Watch Duty App—a tool for tracking of nearby fires and firefighting efforts in real-time. There she goes finding hidden treasures

For the unabridged version of Jesse’s story (which was more riveting and action-packed than even this long-ish spotlight could do justice to!), read the full transcript of our 90-minute conversation below.

Gena:

Okay, so I would love to hear your story. And what usually happens is I'll end up asking you questions that kind of reverse engineer the story, where we'll sometimes be going backwards and sometimes forwards, and you can always cut me off if I'm going too far down a particular rabbit hole. But what I really love is being able to get under the hood of, like, what was actually driving this decision for you? Or, how were you able to rally and make this thing happen? That from outside, either sounds mystical and amazing, or accidental and easy, and it's neither of those things, right? Like, it was a whole bunch of things coming together, and you pulling on a bunch of threads. And so the idea is that I’m trying to really demystify how people build amazing lives for themselves, and the psychological steps along the way. That's the goal.

Jesse:

I don't know where I should start.

Gena:

That’s ok - we can start wherever, and then I'll just start asking questions.

Jesse:

Okay. Then I guess, like, I'll share probably, some more about me that we didn't cover on the boat. And feel free to push us in any direction. I'm from suburban Detroit, and have pretty, like, parents who are, like, not entrepreneurs, like, fairly normal now a school teacher. My dad was a lawyer, um, but my stepdad was had his own businesses, and I, and I got this, like, small glimpse in my teenager life into, like, oh, you can, instead of selecting a job from, like, a drop down menu, you can, like, be an entrepreneur. Like, you can just make something for yourself. And so I was fascinated by that, and attracted to that and and I remember, like, in my high school yearbook, and so I started being like, they were like, where are you going to be? And I was just like, entrepreneur. I didn't even know what it like. I looking back, it's a little cringe to me, because I like, what did I mean? But? But I did. But, to be fair to myself, I did actually start my first business in Expo. Um, I when I decided this for myself, actually a turning point was not getting the captainship to my cross country team. If I'm being perfectly, like, very self aware, I was devastated. My sister had been the captain of this team, and I went to the same school as her, and I was a slightly better runner. Like, just to sound very vain.

Gena:

With these things you’ve gotta be!

Jesse:

So I guess I was a little full of myself, because a lot of people become captains senior year, but I was, like, passed over in my junior year to be captain, and I was pretty offended, and so I decided, like, very as though someone cared at the time, like, I'm sure no one cared that. Like, okay, well, then I'm done with cross country, and I'm going to spend my time starting a business. Like, I'm going to go into the real world, okay, guys, and you don't want me as cross country captain, like, you know, say this to anyone. But I thought it, um, and I, but I had no like, skills like I had to. So I started the first business I thought I could start, which was t shirt printing. I did teacher printing in my basement, and I got a screen printing setup, and I didn't have any money to speak up. So I, like, I thought it was very creative. My birthday and Christmas are both in December, and I asked everyone for like, something I needed, like, little like I so I assembled like, a screen printing setup by, like, getting all these small gifts, like ink, and all these, like, small gifts, my first setup. And then I realized, like, I could actually get more money than just, like, running a service for screen printing by, like, coming up with my own t shirt line and trying to, like, sell the finished product. And so I started drawing drawings, like line drawings I would like print on these shirts. And I called it Genet shirts, because I'm so creative. It's like, my, it's like, Getet is actually my middle name. So again, there's like, so many rabbit holes we go down. But I guess what I would actually skip to, because it really starts telling the tale of, like, my brain, like cycling, like, in an insane way, is, from there I realized, okay, T shirts can only be so unique with you printing them like the same way as everyone else. And at the same time, I was in a photography class in high school, like we my high school. I was lucky enough to still have a dark room like in my high school, and I was fascinated with that process, and I became convinced that you could do photographic printing on fabric instead of, like screen printing. And I went down this rabbit hole of learning about chemistry to try to find a dye that is permanent on fabric, that is also photo reactive.

Gena:

When, like, this wasn't a thing yet? Like T-shirts never…

Jesse:

Exactly, this wasn't a thing yet, although I found these obscure references in some books to this product that existed in the 1950s that did what I was looking for. And so this is, I think it's like…

Gena:

At this point in the story, you're still in high school??

Jesse:

At this point in high school, I'm 16, when this stuff that I'm talking about, I am starting to go down this rabbit hole.

Gena:

I thought I was onto something wanting to ask you for your story!

Jesse:

I went to a local college, and, like, went to a reference library to try to learn about like, Luco VAT dyes, because I was like, there's like this, and that's where I found these references to this product. So I think this is why my kind of, like, I don't know if I want to call it obsessive, that's a little bit like a little bit like a negative term, but, but sure, like this is where my tendency to like I cannot stop like a train, like a freight train of interest, really, sort of becomes clear, because I start by just screen printing, which I think a lot of teenagers dabble with screen printing. And where this ends is I end up finding this guy who had purchased an industrial paints company who had previously owned this 1950s dye formula, and reaching out to him in his elderly years and buying the formula from him. Yeah, this is in high school. This is in high school, and then starting a business around photographic fabric dye printing. Later, after high school, I ended up taking on to Kickstarter, like I raised a quarter of a million dollars on Kickstarter for this photographic fabric printing kit that I ultimately sold.

Gena:

This is so much better than anything I bargained for! I mean, I knew you were cool…

Jesse:

Really, like, it's really, it's really, well, like, it was really, like, the investigative journalism stuff, I don't even know journalism, but the investigative nature that I had to take on to find this guy who lived in Oakland, by the way, and I live in Detroit, so like, this is not very accessible thing to me.

Gena:

Wait, and just, sorry to keep interrupting. Is there Google yet?

Jesse:

There's Google. Like, let's see, what year they sort of been like, they should have been like, 2003-2004, something like that. So like Google, but it's not as like, Wait, it's interesting to look back. Like, it's not as good. Like, yeah, you would, like, sometimes search things and they'd be like, there's no results for that. You know what I mean? Like, it was like, not as all encompassing. Um, so I don't even know where you want to go from there, but, but basically, the beginning of my entrepreneurial career is, I guess you could say screen printing. But then it's when I, like, go down this rabbit hole, and I become so determined that there's, like, this photographic fabric printing, and I end up, I end up actually buying this formula from this old Chinese man. Like, that is the true story. Wow, he's retired, and so he's like, okay, I'll sell you this.

Gena:

For how much, if I may ask?

Jesse:

So I basically structure a deal with him where I—it almost sounds like a fake story.

Gena:

I believe you!

Jesse:

I met up with him in a McDonald's in Oakland to, like, hash out this business deal, and I had to go with my stepdad on a business trip to even get to Oakland, because I'm in Detroit.

Gena:

Um, like he had a business trip that happened in Oakland, and so you joined him?

Jesse:

It’s more unhinged than that, because he had a business trip in LA and in my teenage brain that's close, [so] I actually tag along and then make him drive me to Oakland.

Gena:

Yeah, did he know in advance that that was your endgame?

Jesse:

Yes, well, um, I can't remember how much I sprung on him, because I do. I remember at the time him being very pissed that this was happening, because, so I think that I it was like, I don't think I kept the whole thing a complete secret, but I don't think that I shared how involved doing this would be on this trip. You know what I mean? Because he ends up driving me to Oakland, and then I meet up with this old Chinese man in a McDonald's to, like, hash out this deal. And he was and I was, he's like, what is going on? Like, so I think I obfuscated some of the details.

Gena:

But you also probably just didn't have all the details your mental model, because you've never done it before, and you don't know LA or Oakland, yeah, I get that.

Jesse:

I was just like, I was just having this guy was willing to meet with me, and I was a kind of willing to do anything to go meet with him, basically, because he was he basically wouldn't do email. So, like, he was at an age, you're asking, Where are we in history? He was at an age where, like, he wanted to send back written letters, corresponding by letter. This is real, we were actually corresponding by written letter.

Gena:

None of these things stopped you in your tracks. All of these were like, okay, I'll figure out a way, like, I'll join my stepdad's business trip. Like, nothing stopped you. This is freaking amazing.

Jesse:

In a way, the crazier it got, the more I was like, this must be a good idea. To me. It started feeling like, you know, I think when you're young, like teenager, or at least for me, I feel like I, I try to grasp this sometimes still, but there was this feeling of like there's hidden treasure all over the world. Like there was this feeling of like mysticism and like magic to this experience that I was like, really, like, locked into meaning. I found out that there was this formula in the 1950s that can print photography on fabric, and no one's using it. Like, what's so funny to me looking back is like, I'm not asking myself, what's the market size of people printing photography on fabric that it exists and it's not happening. I was like, may I stumbled upon, like, the most brilliant thing ever. Like, I was very convinced this is, like, so brilliant and so cool.

Gena:

I mean, it's way less delusional than what a lot of other 16 year olds think they have stumbled onto. That's brilliant. Like, it actually is a little bit brilliant, more than a little bit like, I mean, like, that's since become a bigger thing, right? Like, I've even, I know startups that are, like, working on new ways of, like, chemically, you know, like, basic stuff.

Jesse:

And, yeah, I do think especially in the maker movement, let me turn off, no case. Um, especially during the maker movement, like the concept of like, novel ways to like print, things and stuff definitely became like ascendant, and it was that's like sales and 789, like. So that's where some of the timing in my life worked out very well, where I had acquired this formula. So you asked me how I paid for it, because I haven't, I haven't. I didn't have any money. There's no family money. There's no like, magical pot of money. So I basically struck a deal with this guy where I—he had kept, he owned, he had bought an industrial paints company, like, we're talking like latex paint, like, like paint from this other guy in the 1940s who had created this company called Gibson paint. So all of this is like a real thing, and Gibson paint like one of this the guy 1940s the original owner of the paint company, he had dabbled in this for more fun artistic product that he called inco dye, that he sold to schools. And like to like, like to artists, um, in the 50s and 60s. And then when this Chinese man I'm talking about, buys the industrial paints company. he's, like, not very into this weird art product that they have. And so he effectively shuts that down and just runs an industrial paints company, because that was, like, the money making part of the company. And so he didn't care about incurred. It was like, the fact that it existed was like, kind of an aberration to him, yeah, yeah. And so the deal that I come up with, and so then he runs this paint company for his whole productive life, and then he effectively winds it down. He never sells. He winds it down. And there's this he the company was run out of an old bank building in Oakland, California, like we're talking about, like, old bank building, like a big brick building with a vault in it and everything. And what had happened is his kids didn't want to run the business. He thought they might. And so he effectively, like, walked out of this building one day, and just like, never walked back in. And so there's, like, all these assets, like these big paint machines and all these, like, all the assets of this company, and all the old inco dye stuff this, like old fabric dye stuff in this building. And he's old and effectively doesn't want to deal with it. So the deal we strike after talking to him is he's like, you and like, effectively, I will sign over the rights of the inco dye formula and everything. Okay, if you can get me $50,000 I will give you the keys to this building. And if you can sell enough stuff out of this building to give me $50,000 I will accept that like you take on my problem, basically, like, become the operator. But he wanted $50,000 meaning, like, if I couldn't get enough of like, I had to come up with $50,000 one way or another, whether it was through this stuff or not. And so I think I ended up coming up with, like 40 something. I sold the old paint equipment, so I, like, took on this project, and I had to wait till I got out of high school. So basically that I met up with him, and it was like 18 months later or something, that I then moved to California, not to Oakland, but I moved to California to go to school, and then I took on this project. And I would fly up to Oakland, stay in crappy hotels, and like, I ran this whole operation, like selling this stuff.

Gena:

Where did you go to school?

Jesse:

I went to Art Center, College of Design, which is an industrial design program in Pasadena.

Gena:

Wow, did you deliberately choose that as your school?

Jesse:

Partly. It was part of it because my parents did not approve me going to design school. They were like, you're wasting your life, like it was not part of the options that I was supposed to consider. So it was definitely, like, informed by me wanting to go do this thing.

Gena:

Did you apply to a lot of schools? Or was it pretty much just like—

Jesse:

I applied to University of Michigan, my whole family is, like, University of Michigan alum. And I applied to University of Michigan and got in and had a full ride there, and then decided to go out to California to go to design school. So I really was, like, almost disowned, like, from like, it was really like, what are you doing? Because we they didn't have the money to pay for the design school, so I started going into debt to go to the design school instead of going to U of M for free. You girl, I ended up having to drop out of school because I couldn't even afford to finish. So all in all, like, that was a very unhinged choice, because I couldn't even afford to do it, and my family couldn't afford to do it, and I could have had a full ride to a very good school, like a, you know, a very good school, um, do you No, no. I mean, because I was fully convinced that I was going to be an entrepreneur and like, that's all that mattered to me, and I so I feel like I needed to get out to California. I need to get out of my environment and, like, to figure this all out, into like. And then I had this deal cooking with this guy, you know, um, so, um,

Gena:

I mean, can I ask like, how you found the gumption to do it like that again, like, as far as, like, barriers that would stop a lot of people in their tracks, I feel like you've now leveled up past the vast majority of the population that would just be, like, no, peace out. I'm going to U Michigan. Like, how did you do it?

Jesse:

I think it was one of the hardest things I've ever done. Like, I think sometimes I giggle to myself when I'm talking about things later in my career, and it's like, raising venture money or whatever, and everyone's like, how did you do it, you know, and I think back to my harder thing I did, yeah, one of the hardest things I ever did when there was, like, no proof points and all risk, like, and it could easily have blown up on me, meaning I'm a college dropout, like, I didn't even get a good degree because I couldn't afford to finish. And I started myself on this path knowing that, and then it actually ended up true meaning, like it didn't magically work out, like I literally couldn't afford to finish, and then I had to survive as an entrepreneur. So, like, those were the hardest decisions, and I was very exposed to risk. And my parents were the way they phrased the financial piece was, like, we're willing to pay like, what we would have paid for if you had gone to yoga, which is effectively just like room and board. So I had this, like, very subsistence level of support, which I still very much appreciate. So I was not fully disowned or something. To be fair to them, they would try to support me, but they just really couldn't extend themselves past what, like, my food program would have cost a yoga you know? Yeah, um, so those were the hardest. I was very lonely, and I didn't know, I didn't know anyone out here. Like, it was very hard, very lonely. I wouldn't sugar coat it, like, very hard, very hard.

Gena:

Yeah, I can imagine. I mean, do you remember, like, Did you agonize over it at the time? Like, were there days of decision making where you were, like, vacillating between, okay, maybe I'll just do the U of M thing. Versus no, I'm gonna go to Pasadena or like, what did that look like?

Jesse:

Well, okay, one part of the story was not told properly. It's actually crazier than that. I actually moved out to California before I knew I was gonna go to the design school. Effectively, I just moved out to California without a school.

Gena:

So right after graduating, or—

Jesse:

Yes, right after high school, actually didn't go to my senior year of high school, there's, like, some stories I my school district had this, like, loophole that I read about in my student handbook, which was, if you could get the school principal, the guidance counselor and your biological parents to sign a form, you could early graduate. I got myself on a committee with the principal. Like a year before I wanted to do this, to get, like, known by the principal. And then I spent a year…

Gena:

Talk about a long game!

Jesse:

I decided I want to do this in my sophomore year. I spent my whole junior year in this committee with the principal, and I knew that if I get him, then I could also get the parents and the guidance counselor. And so I started that T shirt business that year. And then I went and I was in this committee. It was called the character committee. So I was like, known for being like, Hi character. And I got him to sign the form, because I convinced him that I'm running a business. I'm going some more time, very wisely, I'm going to start taking some college classes and stuff too. And so he signed it, and then I got my parents to sign it, and the guidance counselor signed it. So I only went to three years of high school.

Gena:

When did you get into University of Michigan? Was it the normal timeline?

Jesse:

Normal timeline. I went to three of high school, but I didn't—the way that the exemption worked is you were exempt from attending your senior year, and I still had to complete some credits. And I went to community college and got me and got my like, like, I only had to create, like, a small markets, but I was exempt from attendance, and so I didn't have to attend the senior year. I actually got my diploma on the same timeline as everyone else, same diploma, but and so I applied to colleges at the same timeline, and I use that as part of my essay, like, I'm doing an entrepreneur year instead of a senior year.

Gena:

So I would have admitted you anywhere, yeah,

Jesse:

So the exemption was from attending the senior year, not from, like, having to, but not from the timeline. I didn't actually really graduate.

Gena:

Got it. That's Wow. I'm, like, going back through my own heads, like, did we have that exemption, and did I just miss the ball?

Jesse:

I'm sure it was some carryover that they forgot about. When I mentioned this to the principal, he was like, What? What do you like? He was like, What are you talking about? And I, like, whipped out the Student Handbook, and I was like, Oh, it says right here.

Gena:

That's incredible but wow.

Jesse:

His vibe was like, we should not be giving the handbook to students. Like, his vibe was like, where did you come up with this? You know?

Gena:

I mean, I feel like I would have been thinking, Okay, any future project that I undertake or, like, on the spot, because this girl's going places…

Jesse:

But this is something else I learned early in life, that effectively, like showing a level of like [determination] garners, like, far more respect than it even should, um, but effectively, like that moment, I'm like, just a 16 year old girl who, like, really doesn't know what I'm doing, but I'm like, I need to have this early exemption, because I'm going to, I'm starting this business. And look, here's my T shirts. I'm like, I brought stuff to, like, show him, you know. And he was just like, bowled over. He was like, uh, like, I don't know how to respond to this, you know. Um, and he probably, like, panic, signed the form. He was like, what is happening? But yeah, so coming back to the Coursera line, I actually announced to my parents, I'm moving to California without a school. So I was micro disowned for a second there, but then after coming out here, I applied for and got accepted to the design school.

Gena:

so, okay, so you moved out during your senior year, or, like,

Jesse:

yeah, I moved out. Like, I kind of moved out normal time. I'm, like, I actually, like, lived at home, like, through when I and I went to community college classes, through one of my normal graduation would have been I moved in that summer.

Gena:

Got it okay, and then you got the admission to the design school. Okay, so, I mean, I feel like I could just this, like this episode, could easily drag on for hours, because I have so many questions… but I do want to hear the rest of the stories, and maybe we'll kind of circle back and forth. But okay, so you are now in California, you're at the design school, and you're, you've bought the or, like, you're hustling to make up that whatever it was, 50k for the guy. And then, like, and then that chapter, eventually

Jesse:

I would, so I think, like, yeah, thinking about the core episodes I meet who becomes my cofounder at design school. This guy, Stefan Ingo, and he is so creative. Like, my joke is, like, he really should have been at design school. Like I was, like, LARPing, like, in design school, like I thought, like, having design as a school be so cool. But, like some people, there were, like, so talented and so good, and he was one of those people. And we he was also very, like, dialed into internet culture in a way that I didn't even know how to be at that moment, um. And so he told me, for instance, about Kickstarter, and Kickstarter, when he told me about it was six months old, like, looking back like he was like, he was like, on Reddit. He's like, on, I don't even know where he was on, but he was like, all these places learning about the new stuff on the internet, you know. And so he told me about it, and then he was like, You should do a Kickstarter for this weird fabric dye thing. I was obsessively telling him about, like, I was always telling people about this weird fabric, I think. And then I was like, We should do it together, because I could tell how talented he was. Um, and so. So skipping forward, we do a Kickstarter together for the to raise money for this, like fabric dye. And at this point, it's not to pay off the guy. It's like, actually to sell the dye, or like to start our own little manufacturing for it and things like that. We end up doing two Kickstarters. One raises 13 grand because Kickstarter was so tiny back then, there was actually a lot of money on Kickstarter at that moment. And then a couple years like, and then 16 or 18 months later, we did another one that raised, like, 250 grand or 260 grand, and that really launched that first business, which, like, so I was, we were together, we were fabric dye entrepreneurs, and we sold kits like this, fabric Type Kit ended up we went to the maker fairs, but it ended up selling at JoAnn Fabrics, Michaels arts and crafts, Urban Outfitters. So, like, that was I went on a Shark Tank for it later. Well, yeah, so that was, like, my home startup.

Gena:

Like this was not child’s play—

Jesse:

The largest revenue year for that company was, like, almost $2 million, the top line revenue and at that. And it was like, so it was always, never just massive. But you have to remember how I came from, like, nothing on this, and it's amazing and and then there was no injection, there's no investment. There's no, like, ground, I mean, quick start, kickstart be the only cash injections we got. So I felt very accomplished by that, you know.

Gena:

No kidding! And so, can I ask, like, how old you were at the point where that—

Jesse:

So I would have been like, in my early 20s, like 22-23 I think by the time, like the that business starts clicking. And a normal person would have been probably graduated from college at that point, but I was still in the middle of my program, because I went a little bit later. And then I when the business started working, I decided I didn't want to keep going into I already had student debt, but I had enough financial acumen to be like, this is going to be an unsustainable amount of debt. And so we started making money as a business. And I was like, I dropped out of school, you know, and just did the business.

Gena:

Did you enjoy school? Like, was it a big loss for you to have to quit?

Jesse:

I was upset that I couldn't graduate, in the sense that it was, like, very near at hand, like, so it felt very much like I was dropping out for financial reasons. So that was a bummer. You know, it's hard to feel like you can't finish because there's a stigma. I mean, my whole family my great, no, not my great, but my grandmother, like in the 1940s graduated from U of M, like, I was very much taught, like, we graduated from college. I felt like I was a little bit like, becoming the dullard of the family by, like, not even graduating college, you know, like, so that was extreme to me. In hindsight, I think that I'm probably part of an early wave of people who start to see that the financial—it's not really working. And if you're not trying to become like a doctor or like you don't have to graduate design school, you know, to do design so, so I think it feels wiser, of course, in hindsight, knowing that my life is working out, it feels wiser. At the moment, it felt very scary, like maybe this is a big mistake, you know, yeah,

Gena:

yeah. And did it feel like a choice, or did it really feel like you were just compelled and there's no nothing else you could do?

Jesse:

The only choice was like, I could continue going to debt. It felt like a choice in that way, but it felt like a very scary—that felt scarier to me out of the two things, is it scary to be a college dropout, or is it scary to have, like, 100 plus thousands of debt? It was scarier to me to have the debt than be the college dropout. So I was like, it felt like I made a decision between those two scary things, and I'm like, You know what, I'll be the dropout instead of being the person in massive debt.

Gena:

Got it. I mean, again, at least in retrospect, it seems very sensible, but yes, definitely. Imagine it's very hard to see that without the 20-20 hindset.

Jesse:

It was counter to the narrative at the time. At the time, this is like before people talk about student love, student debt forgiveness, like at the time, people were very much saying, like, it's an investment in your future. Just go into doubt. Like at the time, people really coaching, like, just do it. Like, for sure, so it felt a little bit counter to the advice. But if

Gena:

so, how did you form that counter narrative?

Jesse:

I think by running a business, I was learning in real time how it is to make a real dollar in this world. Like, you know, it's like I was having the like, True Blue capitalism experiences of like paying taxes, like hiring employees, like watching 30% of their paycheck, like, go go away, like, and trying to make ends meet, trying to pay rent. And so I started being like, um, this is so hard. Like, real life is so hard, and making a product valuable people so hard, I can't believe I'm, like, writing checks to the school for like, 20 grand. Like, it's like, popcorn, confetti money. Like it made me feel like this is not a fair—the school is not giving me a fair trade. Like it felt off. Yeah.

Gena:

I mean, which, again, sounds really sensible, actually, but I could see how it was. It would have been really scary and hard to, like, have the certainty in your convictions at the time. So, okay, good. So you went kind of full steam on the business, and did you eventually sell it, or did you eventually wrap it up? Or, how did it how did you get to the next chapter?

Jesse:

I think I was—this colored my perspective of what to do when I got to, like, a feeling of conclusion with my next company, Lumi, because I didn't sell it, [and] looking back, there were people interested in buying it, and I, like, didn't even understand business. So you know, something that is interesting about just going into business and like, learning as you go, as opposed to, like, being an MBA or having, like, some other person by your side, is that, like, I really didn't know everything was first, and I didn't know what I was doing. And so what's funny is, in hindsight, there was two different arts and crafts companies. They were very much sniffing around to to like, at, like, try to buy the company. And they actually would say explicit things to me, and I didn't know how to sell a company like they were trying to buy, and I didn't know how to sell like, and so I put, like, no good efforts into this, until, what's interesting about niche product like that is unless it really has a pure consumer takeover, where it becomes a ritual, like, for instance, tie dye. Tie dye people do every summer, and so there's a cyclical sale to all the tie dye supplies, and people do, and you have to, in summer camps do whatever. I never really got in go die, to become like, like that, like, really done. And so what I did, naively, with Inkodye, is everyone who wanted to try it, tried it. And so there was, like, several big sales years of like, voyeurism with the product, and then there was this really small subset people who actually use it a lot, and that really wasn't enough to, like, make a full product in somewhat the reason why I'm saying it's not even—in someone else's hand, the people were trying to buy it from me probably could have done more for it, but I didn't really know enough. So, long story short, I think I kind of blew it, and I didn't sell the company. I had to kind of wind it down over time. Wind it down over time, and I learned a lot from that, meaning I didn't make the same mistake in the next company. But that's what happened. So it was good and it but I wound it down profitably. But, like, I couldn't really sell it.

Gena:

Or you didn't know you could, anyway?

Jesse:

By the time I realized I probably should sell it, like, I have exhausted the oxygen. I didn't, I didn't do it right? Do you know what I mean?

Gena:

For sure; yeah, there's a lot of timing to these things. Yeah, gotcha. Okay. So, yeah, lots of learnings and still a profitable, like, wrap up. And so then how did you get to the next chapter?

Jesse:

Well, so the connection between these things is the next company, Lumi, that is ecommerce packaging, um, is extremely informed by Inkodye and all these things we did. Notably, it's the same cofounder, so Steph and I start this next company together, and it's really born out of the coffin of the first company, meaning we were networking with all these other product entrepreneurs. We so we went to school for product design, that's where I met him. So we're both study product design, then we launch a product on Kickstarter. We're going to all these maker fairs, and we're eventually networking with the early DTC entrepreneurs like those who are become our friends through all these experiences. And they were all very admiring of our packaging at for our encoded product, it was a retail package. We had ecom packaging, and our packaging was very cool because we were designers, so we designed cool packaging and but so the next idea is bird that of this where we're like all of our friends are struggling with packaging, they prefer to focus on their product. Let's create a business that helps e commerce entrepreneurs by packaging more effectively because it's so painful. So like, yeah, skipping a bunch of other like, tiny nuances, we birth that company. That company, of course, shocker, selling packaging, which is like a multi, multi billion dollar industry, has a little bit more legs than selling photographic fabric dye. Yeah? So bigger company, pretty much out the gate, and we were able to raise venture money for it, because it's, like, an actual market opportunity. And then, of course, we're, like, demonstrated entrepreneurs. We already, like, had run this business that made money, yeah, we went to yc. We got into the real we got into yc. Went to Y Combinator for the packaging company. And so at that point, like there's this transition from us being like homegrown Kickstarter, like stuff for grassroots kind of entrepreneurs to like going through YC, learning [from that whole?] adventure, learning about tech and really becoming like tech entrepreneurs or whatever.

Gena:

Yep. And did you move to, I assume you moved to SF, at least during the time of YC?

Jesse:

We spent three months up there. We always wanted to come back to LA and so we went up there. We lived in Mountain View. It was, like, such a wild wake up call. Like, I was, like, it sounds trite, but like, really, it does make you think bigger. Like, I was running a fabric type business in LA, you know, like I was like, and then you just need to make all the dollars and cents come together on like, the monthly basis. And I was very much a small business owner in my mentality. And so going up there made me think, like, in this much more bombastic way, which has its good and bad, and we really ran Lumi that way. And we raised a seed round. We raised a Series A from, like, tier one investors, and like, just did the whole thing.

Gena:

You say it has good and bad. I'm really curious, just to unpack that a little bit for you personally. What was the good and the bad?

Jesse:

Well, yeah, thinking big is inherently good. I think there's nothing inherently bad about thinking big, but I think that I would there's a build fast… One of my core takeaways would be, there is no right or wrong way to run a business, but you need to run it with intention. You need to know what your goal is, and just target that, and then your funding mechanisms and everything need to match that goal. There's no it's not wrong to run a small business. It's not wrong to run, try to run something that's going to become a trillion dollar business, but you don't fund a small business same way you fund SpaceX or whatever. So So I think that self awareness is key, and many entrepreneurs lack that. And so the good and the bad would be, I don't know if I was always in the right exact mindset for the funding method and whatever I was doing, I had to really become a much more holistic business thinker to finally have everything catch up where it's like you fund your idea the exact way that you intend on running it. So it was, it was a great culture shock to me to effectively raise venture and have everyone expect that was going to build a multi billion dollar business. My brain hadn't caught up yet to that.

Gena:

Can you remember, what was the most painful moment associated with that culture shock, or with kind of that mismatch between the funding model and kind of your hopes and dreams for the business?

Jesse:

I think that probably the true biggest pain was my own psychological catching up, you know, more so than the business, Because oddly, like the business, especially in the first few years, was doing phenomenally well. And that's why we were able to raise a seed and then raise a series A, it was based on the business. And so ironically, in some ways, looking back, it was like me that was having a hard time. And I'll give examples, like, I wasn't comfortable with the level of spend. Like I was, I was, I had a lot of hang ups, I think about money, meaning like they would, for instance, like a venture investor will just say, like, Oh, you're missing. Your head of sales. Hire a head under I would learn that it costs, like, $100,000 to, like, run an exact search with, like, a top tier head hunting firm. And I would be like, I can't possibly do this. Like, I can't possibly write a check for undergrad to someone to, like, put someone in this role, like, there's no like, I couldn't bring myself to operate in this way. Sometimes I was holding the company back. Other times I was probably exercising great judgment, but I don't, but it was really hard to tell the difference. Um, so it'd be things like that that I would draw attention to. And so I think that sometimes I was not being great CEO, because sometimes I was holding the business back because the business was actually performing. And I was like, I'm not gonna start spending paid ads. I'll just do something organic. I'm so creative. Like, I wouldn't do certain types of spending because I was deeply uncomfortable with that level of spending. And then other times. And then I would say, I I overreacted. And I was like, Oh, this is what people do. People just spend on these things. And then I did some of it indiscriminately, meaning I wasn't even smart enough to do it well. Because I was like, oh, people hire headhunters. I'll just hire Headhunter for like, HR. Like, you know what I mean?

Gena:

Like, yeah, calibrate…

Jesse:

like, I couldn't calibrate. Like, sometimes I wouldn't spend, and then other times I would tell myself, this is what people do, and just spend even when I wasn't necessarily getting a result that was meaningful to the business. So I would just say that there was so much pain and all of that, right? Like, pain, about messing up pain, about, like, soul searching, of like, what's comfortable with spending…

Gena:

About hiring and managing?

Jesse:

I definitely found it hard. It took me years, and I think I finally got decent I think managing, especially high performers and, like, executive type people, is a lifelong skill. Like, no one's just like, Oh, I got there. I'm done now, you know, so it's a lifelong thing you're perfecting, but so, but I would say I got good and I started terrible, and I got okay or to good, and there's always room. But something that made me terrible at first is I again, college dropout. Never, I never climbed the, like, tech ladder of jobs. So these people were like, gazelles to me, like, yeah. What are these people? Who are these people like, Who are these people who just walk into like, and they're like, oh, yeah, I did x, y, z here, and then I worked at McKinsey, and then now I want 250k for this job. Like, 12 months before they're saying that to me, I was paying myself, like, $50,000, I lived in a trailer behind Lumi so that I could pay off my student loans. And so these people didn't make sense to me. Like, where did they come from? I would be able to put on a face of figuring it out, choosing someone good. I had a really good radar for character, so I was able to hire people who were good, like, they weren't just telling me lies and stuff. I was able to have people that were good, but then we related on almost nothing, so I was able to get them in the door, but then it was like, what do you do with these people? Like, what do you say? So it took me a while to actually develop enough personal confidence to manage them at all as a peer or as a manager, like, let alone as a manager. That was a learning experience.

Gena:

Yeah, I can only imagine, and again, you can smile about it in retrospect, but I can totally imagine, like, being in the thick of it and feeling like, I don't know, how am I supposed to lead these people?

Jesse:

Yeah, it was very confusing. It was very confusing. And then lots of like, classic imposter syndrome, like lots of classic imposter syndrome, feeling, um, I will pinpoint something that that helped me crest over. And it. Is very concrete, which is I moved into the Airstream trailer behind Lumi HQ during the inco die days, and then stayed in the trailer through into the Lumi days where we're doing the packaging in order to pay off my student loan. So like I was giving myself a small salary, pretty modest, now that I know other people pay themselves, like I just didn't know what people do, but I was paying myself, but I lived in this trailer so I didn't have rent, and when I finally got to $0 meaning I paid off my own debt, and then I was just earning income, and, like, there was actually, like, $1,000 in my bank account, or, like, literally, we're talking about these amounts of money, I felt so much more confident. Yeah, debt was truly, like, contributing to my imposter syndrome by a lot for me personally. I don't know if that's how everyone reacts, but that's what I'm saying when someone would walk in my door and ask me for like, a 250k salary, and I'm like, trying to scrimp—

Gena:

trying to get to zero, yeah—

Jesse:

on dollars a month to get to zero. I, on some level, I was deeply offended, you know, like, or felt like, I need to get to zero first. Like, maybe it's not fair to them at all to me to involve my own financial thoughts, but there was some unleave, some level, where I thought it was unfair, basically, like, if I'm going to be CEO of your company, how am I in debt and you're going to be that's not really how the world works. But yeah, it felt bad to me, and so something that I do coach people on is you need to feel okay. You don't even feel great all the time, but you need to feel okay about yourself financially, and that's partially why you need to pay yourself a salary level that makes you feel okay, because otherwise you literally do resent everyone on your team.

Gena:

Yeah, I mean, such a good call.

Jesse:

And that's not worth—it's not worth the resentment, because they didn't deserve that, like they're not doing anything to deserve that. Um, so that was a turning point for me, when I felt okay financially, not great, but just okay. Then I was actually able to be a much better manager.

Gena:

That's so interesting and such a fantastic self insight to be able to surface.

Jesse:

I didn't even know that. The bad part is that I didn't know how bad it was making me feel until it was gone. Yeah, absence of that feeling, you know?

Gena:

Yeah. I mean, for me, it was when I got financial independence from my parents. Like, how is it that all these neuroses that I just figured I would be carrying around with me for my entire life, they're just gone? Like, now everything's fine, like I can just call them and then hang up in 10 minutes because I'm busy?

Jesse:

Yeah, it's like the absence of something that you didn't even know was weighing you down.

Gena:

It's wild, and that it didn't have to… Oh my gosh, I have so much I want to ask you. And how do we have six minutes left in the hour? I'm still learning how to time these, as you can tell, but also I just feel like I could talk to you forever. Um, do you have a hard stop?

Jesse:

No, no. We can go for a while, I don't have a hard stop.

Gena:

Okay, well, I will try not to take too much advantage of that, but there's a little bit more of the story. So how much do you feel like you want to share about how that startup wrapped up?

Jesse:

I'm happy to share very candidly, like I hinted at it, but from the first business, I did have a bit more of a sense of the momentum of things and how, like, you can't you can't wait till it's effectively too late. Which, which, I don't know if this will make sense to people listening who have never run a company, full course or something. Obviously, if everything is going literally like perfectly in your company, you never feel this, because the company is just literally growing and growing and growing, and there's no feeling of like edges to it. But I do think there's a lot of businesses where you start to feel an edge. And it's not always falling off a cliff edge, but it's like, oh, I'm feeling the edge of my business idea, or the edge of my market, or I'm feeling like we are not going to keep growing the same way. If I don't do something radically new, I can't keep on the same course. So I would say I would if there's like, a little advice component to this, I think, I think [if] entrepreneurs are really honest with themselves, you do feel that sometimes, and you do start to recognize that there's an edge to something, and you need to ask yourself, am I the person who pushes past this edge and gets us, like onto the whole next course, or is this a time to partner or sell my company because it's actually better, or will grow better as a feature of something or within an umbrella with different resources? Like we are coached in the startup ecosystem, at least, to never admit that, because everyone's building a multi billion dollar business. If you say anything else, you lack ambition, that kind of stuff. But if everyone's really honest with themselves, sometimes you can tell, and I started to feel that because the direct to consumer sentiment was changing, the direct to consumer businesses that were our core of our customer set were not always succeeding themselves, um, and so some of our customers were going out of business, like, is what I'm trying to say. And I noticed that trend. But then that doesn't mean we're going to because we have, there's so many people you can sell packaging to, but I started to notice, like, a sea change of, like, shifting in the customer mindset, and some of them were not thriving. And then I know some other things structured about the business. And I really had a hard look in the mirror, and I decided, I think I'm gonna sell this business like I decided to do it. Well, we had revenue. Well, actually, many things were going well as as opposed to waiting to find out, yeah, if I could push through to the next level, or whether there would be a failure moment.

Gena:

I mean, can I actually just really zoom in on this? This is so beautifully articulated, and it's a moment that I have very much seen founders navigate or fail to navigate, or be on the cusp of admitting that, you know, they feel that edge. And it's such a valuable insight when you say, like, the thing that you were looking hard in the mirror about, like, the question that you were asking: to what extent was it, can I be the one to, and to what extent was it like, do I want to be the one to?

Jesse:

It's so deeply both. It's so deeply both. I'll give a more concrete, because I I'm very open to sharing this stuff, because I think it is very under discussed for a million reasons. Usually people find it somewhat embarrassing. Sometimes merger acquisition docs are filled with non disclosure stuff, so sort of, structurally, people feel like they can't share, yada ya. But a concrete thing I definitely can share is we were we were made the company was making money. There was ways to run the company, sort of profitably, but you're always expected to grow. When you're venture backed, you're not gonna just like, stay in a stasis mode. So we were very much actively discussing raising Series B to continue growing, you know, as opposed to, like, saying where we're and started having Series B conversations. And a moment that was pivotal to me personally is I was able to get meetings with all these investors I deeply respect. Like again, just to use the industry parlance, like tier one, amazing partners, like amazing firms, I was able to get the meeting, and I was able to see that the most compelling way I phrased the business was not landing for them. I was able to see in the whites of their eyes, like them not really being that excited, um, and then, then I won't name names, like, make people feel super embarrassed. But then I was the effectively, I was only able to get invite excitement for the business from what I consider not tier one investors. So, and I actually got a term sheet that was like, very middling in all respects, middling on price, middling on terms, middling on who gave it to me. Um, so it was a real look in the near moment where I was like, there's a reason the people I respect most in the universe aren't that excited, because there's some edges and there's some cracks here. And again, you can then say, okay, like me against the world, the packaging industry is huge. I must be able to, like, reinvent a company and reinvent parts of this, and then they will be said. And there's always that you could but what I saw was like, I've been running this company for five plus years, six years, and if the people I respect the most in the world are like, asking good questions, poking holes, those holes are valid, then I also should listen like there's a there's a listening there's like a instead of just this, like, you're encouraged to have this complete blindness to reality. Sometimes, as an entrepreneur, of like, No, you are building a multi billion dollar business, no, like accepting anything about like, accepting that there's any problem with your business you can't solve is like, basically just being like a total pushover. So I decided that there's something in that narrative that's wrong, because there's all sorts of very shitty companies that keep shittying around. Okay, yeah, that's going to look very weird in the transcript.

Gena:

That's actually pretty creative, but anyway.

Jesse:

but so for me, it was a wake up call where I was like, Maybe I need to listen to this. And I need to, basically, I'm the only one that can kill this particular baby. Yeah, is what you sometimes also need to realize the investors are never going to kill it. The investors were like, You got a term sheet? Like, take it, spend the next five years growing up. Because they, of course, would, far would are their math is much more like, give her more shots on goal. Maybe they'll figure it out. Um, so, so So I realized that as a CEO or as a founder, you to be very graphic. You're the only one that can suffocate your own child, like you alone can sneak into the room and go in the corner like, like, what is she doing? Why is she saying this? But like, I'm saying this dramatically to highlight that, like no one aside the founder, can kill the company usually. So you must, sometimes…

Gena:

This is incredibly powerful, vivid imagery to illustrate the point… Is it also illustrative of how painful it was for you?

Jesse:

Yes, I think that's why I'm using that language. Because also, ironically, maybe what people can't read with the killing the baby analogy is okay, the better analogy is adoption, because only you can put your child up for adoption and say that's what's best for it. Like, that's what I really did, right? Like, I actually sold the company for a non marquee sum of money, but it was sold. There was exchange of value, um, the people involved did okay. And that decision effectively to, let's continue the analogy less bleakly, and say, to put the child up for adoption, had to be made by the founder and everyone else involved. Would be like, maybe you can raise it. Maybe you can send it to college. And I had to be like, I literally can't Okay, I'm going to put up for adoption. It is going to be, it's going to have a better life over here.

Gena:

Yeah, but again, like, I still can't help but think so, what you saw was, like, I don't have it in me. Like, whatever would be that set of moves that, like some founder could make here to get it over this hill, to, like, change it enough that now it does, you know, have, like, a credible market and, like, I've been doing this for five years. I don't want to do another five where maybe eventually, like, after a million, you know, iterations that fail, like, maybe through much pain, I kind of figure out that it could be this very different company than the one I actually built, and it could succeed, or I could, like, go to the next chapter. Like, I'm just wondering, you know, was it that?

Jesse:

Where I'm sharing that anecdote, where I had meetings with people I deeply respect, and I gave them my most compelling pitch authentically, like I was not, I was not off the wagon like so imagine me fully on the looney wagon, yeah, fully convinced still that I'm like, doing everything I possibly can, and that it can go well, giving my most compelling pitch to people I think are extremely smart and seeing in their eyes the lack of belief. It was that that made me be like, maybe I have crested into a bit of delusion, like, maybe I am perpetuating something that isn't quite there. So it was, it was, it was seeing these people who really, and I want to be very nuanced about it, because effectively, sometimes in every in every fundraise, you get told no 100 times, but I'd already been through that a couple of times. So this is what's different in the seed round, in the series A I got lots of no's, lots of no's from people I deeply respect, but then I found someone I deeply respect who gave me a yes and who authentically believed the entire narrative. I'm saying this was different, you know? So it was like me picking up on the energy and deciding, I think that what I just what the team deserves, and what even the original idea deserves, is to try to live in this new way, versus me running it into the ground this way.

Gena:

So it wasn't like, okay, well, I could continue with this default kind of vision and model, or I could do some sort of hard pivot. And here's something I have in mind. It was like, This is what I got, and I'm seeing the writing on the wall. This is not probably this isn't gonna work, yeah. And so I've kind of played my card.

Jesse:

So to speak, yes, and I saw a potential for it to exist within a broader set of products, like in another company, um, the company that purchased it. Um, does, like, ecommerce, reverse logistics, and, like, had all these other customers that were, like, symbiotic and, and it was like, I mean, I didn't know the acquire at the time. But like, basically, it started to dawn on me that even though you're told, like, growing a big standalone company is literally the only goal, like plenty of companies have end up in ideas end up having success in a slightly variant of that existence. And so it became, like I was finally willing to admit, like, maybe this idea, maybe this packaging product that we built has some value, but like, on someone else's thing. Yeah, it was like, but admitting that was felt like, it's like flying counter to everything you've ever [been taught] as an entrepreneur. And so admitting that, and that's really like, coming back to my little adoption analogy, like to bring the pain to it. It's like it, it felt like admitting as a parent, like, I can't raise this child, like I even though it's my child, and the only reason it exists is me, like, I'm not serving it very well anymore. Like something is off here, and I want to still give it the best shot it can, you know, like, that's why so, so that adoption is actually like, I've never put a baby up for adoption, so I can't really, I'm not speaking the true emotions. But as an analogy, I think it fits, yeah,

Gena:

I mean, but I do think that there's a real emotional resonance in that analogy with, like—

Jesse:

It was my baby, it was my soul, was my whole professional identity, and so felt like giving that up, like putting that on the market. That's why I don't, it's like, it felt like just being like, here world, take my soul, you know? Like, yeah.

Gena:

And, I mean, I'm having so many thoughts here. One being like, good thing you had the training, gave yourself the training early on in your life, of like, moving to California against all the conventional wisdom, right of your family. And like making that really hard, uncertain decision, and like honing your self trust, honing your bridge and your judgment in the face of a lot of these really kind of risky, uncertain situations where, like, Yeah, down you knew even this you could handle, you know, but it would turn out okay somehow.

Jesse:

And it did feel, even in my cofounder dynamic, like I had to be the one to pull the cord, like, because my co founder, I don't want, was so incredible and like, such amazing partners. So the next thing I say, I don't want to be negative reflection on him at all. But effectively, it did feel like, if someone was going to have the courage to, like, put the baby up for adoption, like I had to do the hard thing for everybody, because I was the CEO, like and the original. I was often the original motive force behind it. And so it felt like it felt like my duty, like, no, it felt like I would be cowardly to make someone else do it. I guess. Let's put it that way. It felt felt more like it would be my cowardice to make my investors come to me and go, I think, Jesse, we got a problem here. We're going to shut this business down, or to make my co founder come to me and say, I think when you sell the company. It felt like an I didn't act clearly. It was shirking the responsibility, so I felt a deep responsibility to actually make this tough call so that everyone could point to me and go, she decided, like, it's like, I felt like my job to do it, you know?

Gena:

I mean, and major kudos to you. I'm so glad that I'm profiling you, spotlighting you, because this is such an incredible example to so many founders who are still, you know, on the before side of that story. And there's no fact of the matter about whether they'll find that courage, and having a story like yours is a tremendous resource.

Jesse:

So I got pushback from investors. So in case anyone is curious, like I there was a moment where I decided we are not going to raise a series B, because, from their perspective, we're in the process of raising a series B, and it's somewhat imperative, like, there's ways we could, like, trim back to try to, like, have more runaway and different stuff, because the company is making some money and whatnot. But it was, like, somewhat imperative that we raise unless we radically change course and effectively so. So, from their perspective, I'm raising, and then there's a moment where I tell them I'm not going to raise a Series B. I have a couple conversations started about possibly partnering, or selling the company, and those conversations are either going to work out or they are not, and I'm going to see them through and run their course. And they were like, uh, what? Like, what are we talking about? Like? Because the concept that entrepreneur. Have any options available to them that they're not taking is, like, anathema.

Gena:

Given their incentive structure, yeah.

Jesse:

So they were, like, kind of shocked. We did call, but I this is a moment where I had never done something that they didn't like, approve of, really. So we had a very good relationship. They were very good investors, meaning respectful of me and stuff. And they and I remember it was the first and only time I ever said this to them. I said, like, at the end of the day, I believe that, as a CEO, this is my call, right? And I actually had them be like, yeah. And then I was like, then I'm making the call, despite you not liking it. I'm just double checking that you view it as part of my job as CEO. And they were like, yes. And I was like, then this is what's happening, and no combativeness. But I was like checking, like, I'm a CEO still, right? Like you're not firing me yet, right? And so I'm—this is what I think we should do. I believe this is the best, best course of business. And they were like, yep. And I was like, then this is what's happening.

Gena:

I mean, you're literally, you know, we talk about, like, needing the magic words to have, like, really hard conversations and to make hard choices, and you're literally giving me magic words right now, literally like, check with your investors this I'm as the CEO, this is my call, right? Yes, we're all agreed. Like, yep, they were like, they were they were like, through pursuing like, why didn't we fire her yesterday?

Jesse:

Yeah, exactly.

Gena:

But no, I'm sure that wasn't, you know, like there are very good reasons that they trusted you and supported you, and they had to remember all of that as part of the context when you kind of called them to attention on what they knew and and it sounds like they did well with you after that? Like, they didn't.

Jesse:

We sold the company. So then, yeah, like, so I'm then it's not all doom and gloom. Like, when I announced I'm going to do this, course it meant I'm not going to parachute in a fundraise. I also said I'm going to do a layoff to give us more time. So I was like, it was like, it was like, I'm not gonna do fundraise, I'm gonna do layoff to give us more time, and then I'm gonna pursue these opportunities. But then it was like a sort of awareness of like, If nothing works out, we could be in a much worse position, but we're not there yet, you know, like, I'm gonna do my stuff. And I did effectively sell the company, the teammates that we had all got job offers at the new entity. No one, no one lost their job as a result of the acquisition. People lost their job during the layoff. But the acquisition actually, you know, hired all the team members that we had on, that we had, there was actual cash and stock that changed hands between the entire waterfall of the cap table. And then the product existed for a while. They did ultimately end up shutting it down, like, two years later. So that's like, not my favorite thing, because I'd love if it was like, out there, blah, blah, but it had a good run. It made money in the new company as well. And so it's not a sob story, but it is a story of, like, I had to bring it to that conclusion.

Gena:

Yeah. I mean, it's incredible—I think it's so far from being a sob story. I think it's a tremendous, like, honest success story in the grand scheme of things, of like, how to actually rise to an occasion and do the right things.

Jesse:

I mean, you know, I can think of one, out of all the employees that we had, which is a lot over time, like, I can think of one person who was like, very pissed that I decided to do this and felt like it was really the wrong choice, and told me so. And like, and you have to talk, be able to talk to that kind of person and be like, we respectfully disagree, and I'm in this seat, and you're in that seat, you know. So, like, there's all sorts of tough stuff like that.

Gena:

Yeah, there are no shortcuts around those hard conversations. You do them, eventually you get better at doing them. Ok, this is hilarious—we haven't even gotten to the story of how you decided to be a full time mom for a while. That was the actual official impetus for having this conversation. How much time do you have?

Jesse:

I can probably go for like, 15 more minutes. Do you think that's okay?

Gena:

Let's do it, okay.

Jesse:

If you want, if you feel like there's like, so much unfinished, we can always do another, but I can for right now. I can go for 15.

Gena:

Perfect. I mean, and thank you for that, because partly, just selfishly, it's just really fun talking to you and hearing your story. So I might hit you up on that, but let me see—I feel like I also remember you telling me that you were pregnant as you were doing the sale. Am I remembering this?

Jesse:

Yeah, so, so somehow, like that whole story, I didn't even mention that, yeah, well, that year where I make all these choices, we're not going to Series B and everything, I'm pregnant, um, and I know I'm pregnant, and at first I am told investors, I ultimately tell them kind of during the middle of it, but I made the decision, and this is that I made the decision to not tell the acquirer. And at the time, it felt pretty basic, because, like, when I, when I first started talks, I was like, 10 weeks like 12 weeks like so it didn't feel relevant. I wasn't even, like, telling all my family, like everyone. But then, of course, everything takes longer than you think it's going to take, and so the long and short of it is, by the time the deal is being signed, I still didn't tell them, and I'm, like, eight months pregnant. That's right, that wasn't my goal, because that's an insane goal. But what, what is, what I would share that's very honest is, why didn't I tell them? I'm not a big fan of office getting information. But what you notice in a deal is there's all these moments, and every time you think it's done, it's not done like you sign a term sheet, but the term sheet says all over it, like, people can back out for any reason. And so I thought, I thought to myself, naively, oh, as soon as I have a term sheet, I'll tell them. Then I read The term sheet, and I'm like, Oh, this is they can back out because, like, I sneeze wrong, let alone be pregnant. Like, oh. So I'm like, so I don't feel comfortable. Then I tell myself, like, okay, but when the lawyers are working on the deal docs or all these points, I tell myself, I'm going to feel comfortable like doing it, and I'm not going to worry that it affected the deal effectively. I never feel that way, and it's no fault of theirs. They were acting normal the whole time. I unfortunately just felt like this information could be bad, like could soil something like, fairly or not, fairly or not. I felt that way. And so I really only felt comfortable telling them when it was, like, completely age, completely done. And that happened to me, and I was eight months pregnant. So that was definitely an adventure. I tried to be as above board with it at that point as I could. I offer. I was like, I don't have to take a full maternity leave. There's all sorts of things I can do, especially during transition, or try to do the best I could, but, but it was what it was. I mean, I had a baby a month later.

Gena:

So, I mean, can I, can we just go back and quickly ask, like, did knowing either that you were pregnant or that you were getting pregnant, like, did that play into the decision to go ahead and sell?

Jesse:

Great question. You know, I think that it did only in the sense I already, this is my second pregnancy, so it didn't in the sense where I was going from zero to one, like, oh my god, I'm being a mother now. So I already knew what it was like to have a kid. I had help and support to like, it wasn't just a like, I'm becoming a mom, I need to sell this company, but it was, I do think that there's something about children that does make you—I think it added to my self awareness, like when I was having those calls and like, reading people's mood and stuff like I'm talking about. I think it made me feel like, you know, time is very precious. Um, I need to be very calculated with how I spend my time, how I spend my energy. I need to be a good leader. I need to be a good mother. Like, I think the pressure on, like, being very decisive and being good leader felt more and so I think it amped up that part, meaning it didn't feel reasonable. It felt even less reasonable. As a mom of one, soon to be two, to be kind of, like delusional, like, I'll just build a multi billionaire business, like, no matter what piece of data presents itself, like it felt less reasonable to be delusional, um, but, but aside from that, I would say that's a major factor, um, but I didn't feel like I couldn't run a company as a new mother or something. I was already doing that for like, two years, yeah.

Gena:

I mean, that's beautifully explained, and I think a lovely and underappreciated dimension of pregnancy.

Jesse:

It’s clarifying, like, there's more…

Gena:

Yeah. Like, it sharpens for us what the stakes are, right, in terms of the one resource, which is our time?

Jesse:

for me and others, like, again, fairly or not, me making decisions for others. But it felt like my time was very precious. Then I'll give the quick example. My co founder, he. He is so talented. I knew that the whole time, the first thing I said to you is, like he's so talented in design school, like he's so talented, he's so smart. That's why I loved being his co founder. He I started to feel and it's, you want to be careful about making decisions for other people. But I started to feel like he he was never going to leave my side as a co founder. He was never gonna like, but he also was never gonna probably Shut, shut this shit down. You know, I'll just say this, since selling Lumi, he is thriving. He is doing so well. He is a CEO of a new company that he's working on with new people. They are crushing. It's a product that is so akin to spirit. He is engaged like, some of this has nothing to do with anything, like apropos of nothing.

Gena:

Not nothing, because it's important to be able to—

Jesse:

I take no credit for him doing amazing on his own. But what I'm saying is I actually, even as a mother and whatever, I started to feel like, you can't just go wasting other people's time, either, like you need to be very clinical about how you spend time in your startup. You shouldn't be putting other people in Dead End careers, either, like I was, I just felt a new responsibility, I think, for myself and everyone.

Gena:

Like, with a shared reality that you knew would affect everyone, yes, that you were, like you said, the only one who was going to actually be able to call that reality.

Jesse:

And that's the CEO. Like, in essence, like, that's the CEO's job, like, to make each of those tough calls and take full accountability and to make the call that, like, makes other people have to not make that call, you know? That leads to me, it felt like that was that moment, you know?

Gena:

Also a beautiful quote. I'm so excited to quote you at length. Okay, so now… the story of how and why you decided to make this your next chapter. You know, what went into that?

Jesse:

So obviously, like during Lumi I’d had a child in 2020, like peak COVID, all sorts of craziness. Had another child in 2022, and then when I left, when I left the acquirer—so I worked there as an executive for a little while when I left the acquirer, so I had two kids, like I knew I would take a little break, like I had been working non stop, like, through these, all these entrepreneurial chapters, and so I knew that taking a break would be good for me. I have these little kids. So that part didn't feel that weird. And it felt like even like a guy would do that, like anyone would kind of do it. But I think there's a turning moment where, like, now that's like, over two years ago, there's turning moment where I knew it's not only a break, like, I actually want to do this phase and then admitting that, like, admitting, like, it's not just a sabbatical. Like, like, for a while I had all these terms, especially with my female friends and stuff like, oh, I'm like, rethinking. I'm taking some time to rethink. I'm thinking about my next idea. I'm like, there's all these things you say to make clear to people, like, you're not out of the game. You know what I mean, like you're you're just thinking, you know, whatever, I think there's a turning point for me, and one is kind of an extreme life event I had after the second baby. I had an ectopic pregnancy and almost died, um, like, I end up having emergency surgery, like, losing a lot of like, my blood, like, like, truly, not, it's not over dominating at all. I was, like, on an operating table and emergency surgery, they were like, the doctors were like, looking at me, like, we're going to lose you. So, yeah. So all that to say after the two babies, then there's this like, topic, like, right around the time I actually was leaving narbar, um, leaving the acquirer, so I think there's something about a near death experience that also is very clarifying. Because I started to realize that some of the narratives of, like, what I would tell my female friends who are ambitious, for instance, of, like, Oh, I'm thinking about my next idea, like, that's what I'm doing. I sort of realized, like this was storytelling, like this was a form of storytelling to convince people that I was still relevant and whatever, and I could detect. I really could through all of this, and especially with the near death experience, I became better at detecting my own bullshit. And so I realized, after probably almost a year of telling people these types of things, it became clear to me that it was like just something I was saying as opposed to being real. And so then I asked myself, like, what if you just stop saying that. Like, what if you just say, like, I am really enjoying being with my kids. And then I got pregnant again, and then I'm like, I was like, I'm just momming, you know, and and then the real crust over is like, there's a moment where I realize I'm telling a form of bullshit. And I'm like, I'll just stop. So then there's a lack of bullshit. But then in the vacuum of no bullshit, is like, what if I go one step further and I actually say out loud that I think more women might want to consider spending time with their little kids like that. It's actually really great.

Gena:

What has become mind-blowing again, yeah.

Jesse:

And so, the reason I started feeling that it would be very easy, and if anyone wants to say this about me, that's fine, because I feel pretty bulletproof that, of course, you want to, like, show you're doing, you know what I mean? Like, if you're doing that, you want to be like, This is really cool, guys. So I'm open to this accusation at the same time. What I really was feeling and why I want to be a bit more vocal about it is, I feel like it's almost verboten, like, it's like, not allowed speech in like, ambitious circles to say, like, I actually think taking a break with these little kids or spending a lot of time with them is meaningful. Like, I don't feel like I'm missing out on something. I feel like I could do career later. So I decided, like, you know what, if there's any women out there feeling like they can't really talk like this, fuck it. I'll do it.

Gena:

I might cry, or I might already be crying.

Jesse:

And then I'll share another thing, very candidly, which is, I sold my company. I did okay in the sense that I've got more money in the bank than teenage me, or me growing up in the Midwest with normal parents would ever assume I would have. But then, in addition to that, my husband, my partner in life, sold a company for even for better than living. And so between these two things, I don't need to work right now to feel like my kids can survive whatever, when you put that all together, I felt like I am so low risk at like just explaining myself and just sharing my thoughts that again, if there's anyone out there feeling a little unseen, feeling this way, or feeling like they're not ambitious, if they feel this way, I'll just say it. I'll just see what happens, and I'll just sort of, like, if there's any heat, I'll just take it like I don't care, like I have so little risk right now in saying this. So I just decided to speak more publicly about it and be very pro natalist, like, I've been accused of being pronatalist.

Gena:

How dare you be pro children! What a crazy notion.

Jesse:

Just be out there. Like, if you're in a relationship with a partner that you really like, who you respect, who you think, you'll be a good parent. I'm out there being like, do it. Don't wait, just do it. So now I'm just kind of like, vocal and I'm just sort of experimenting with that. To me, it doesn't mean I'll never do career things, but I feel again, with the force ranking of how I spend my time, it needs to be very compelling. I'd also prefer to maybe get out of the super little kid era if I can, but if I got bitten by the bug of some new idea I wanted to work on, I would start working on it. So that's kind of where I am, but, to me, in a way, the bug I've been bitten by the most is, like, kind of talking about it, and kind of opening, if there's an Overton window to open about this, where it's like, you can be ambitious, you can be interesting, and you can raise kids and spend time with them if you want, then that feels kind of meaningful to me right now as well.

Gena:

Yeah, I mean, in a way, it's its own kind of startup mission. It's like, there's a mission statement. There's a roadmap, just in virtue of—they're gonna at some point age out of, you know, needing the same level of attention…

Jesse:

Yeah, it’s similar…. Yeah, so that's been a journey, but, and now it's like, who knows, what's next, but—part of what makes me feel like it's at least appreciated by some is, of course, conversations like this. But like women will DM me, like, who would work at VC firms, or who feel like it needs to be a secret thought that they do appreciate that I'm sharing in this way. The fact that they need to be surreptitious a little bit about saying it tells me what I need to know, which is, like, this is still not—how could child rearing and growing the family or even home, creating a good environment for your partner and your kids, be this, like, touchy of a subject, you know?

Gena:

It’s got me very glad that we have someone like you pushing back on it and providing such a wholesome, inspiring example.

Jesse:

I'm trying.

Gena:

You’re doing great. So thank you, and I will let you go, but I'm sure it's not the last time I will bug you!

Jesse:

If you want to have another conversation, let me know. But hopefully this is helpful, and I appreciate your interest and that you're out there being ambitious and doing all this intellectual work and, and then also, like, unapologetically being interested in your own kids and talking about them—unfortunately, there's just not a lot of people doing that.

Gena:

Yeah, which is why we need—why I'm going to publish two separate spotlights. So that we can have as many data points as possible. Because you're really right that there aren't enough. And particularly, you are two really ambitious, really high agency women who, in your own very different ways, have very consciously, intentionally decided this is a chapter that you want in your life.

Jesse:

Yeah, we need more strength and numbers. Yeah. Seriously, thank you. Thank you so much for this wonderful conversation.

Gena:

Very much likewise—thank you and Happy New Year.

Jesse:

Happy New Year!

Recently I got called to account by my husband Matt for the conspicuous absence of career-typical paths in this series. Most people, he reminded me, are not and need not want to become founders. Most people—including some of the awesomest people we know—are pursuing traditional, well-charted career paths, like law or medicine or accounting or IT, and generally living a fairly ordinary and private life.

Matt’s comment made me realize that my almost exclusive showcasing of visionary entrepreneurs and innovators as exemplars of the “builder’s mindset” has instanced a common bias within the countercultural circles I spend my time in. But that very bias, ironically, has a drill-sergeant-y mentality built into it, and it underrepresents the range of ambitious, fully-lived lives that one can build.

So today, I’m spotlighting one of my favorite “career-typical” friends, Anne Briard, whose approach to life exemplifies the builder’s mindset to an uncommon degree.

Builder Spotlight: Anne Briard

Principles on display: The builder’s mindset as a third way; your life as the measure of all things; we build ourselves by building

Anne Briard is a liability and property insurance attorney you’ve probably never heard of, unless you happen to be part of her typically-sized professional or social circle. She is also one of the most principled, independent-minded, joyfully fulfilled humans I have the privilege to know. I first met Anne when she started dating my good friend Ben about a decade ago. Anne and Ben are now happily married, and let’s just say that seeing their relationship unfold not only made me rejoice on both their behalfs, but also inspired new heights of optimism and romantic ambitiousness in me.

That said, I’d never really asked Anne much about her work or how she built herself into the person she is today. So last week I sat down with her to get the full story. Here are some highlights from our conversation (which paid subscribers can read in full below).

Forming a vision for her life

Growing up with wonderfully loving but “sort of Bohemian” parents in rural New Jersey, Anne knew from early on that she was “a little bit different.” Jokingly comparing herself to Alex P. Keaton, the Michael J Fox character from Family Ties—who rebels against his hippie parents by being conservative and wealth-oriented—Anne said she always “wanted to make a good living, but I also wanted to do something that was kinda hard.”

Between seeing the nicer houses and toys that some of her wealthier friends could afford, reading books like Roald Dahl’s Matilda about “kids who were in kind of chaotic houses and wanted to change things for themselves,” and visiting New York City with her family twice a year and seeing what a “different kind of place it was”, Anne formed a vision of the kind of life she wanted to build for herself.

Hearing Anne talk about how she compared herself to the children with nicer houses and became “interested in more materialistic things than the other people in my family” got me curious. Without further context, these statements seem almost tailor-made to fit the cultural stereotype of the “soulless, money-hungry lawyer,” and yet nothing about the adult Anne I know even remotely resembles this stereotype. So I asked: what was it about the “nicer houses” that appealed to her? Was it something about the success and status those nicer houses represented, and a need to prove that she too could be successful, a la “keeping up with the Joneses”? Or was it literally about wanting a nicer house?

It was literally about wanting a nice house, she said. Specifically, it was about being out in the world and having her own place, ideally in a cool city that’s “more in the center of things,” surrounded by people “doing interesting things, living interesting lives.” And because she knew that this kind of lifestyle would cost a good deal of money, she wanted a well-paying job.

And how did she land on law in particular? Because she wanted a job where she could “solve real problems,” and she had excelled in the humanities more than she had in math or science—partly owing to a “really tough” humanities teacher in middle school who had inspired her to really “work at something to get good at it” for the first time.

Reclaiming the “ordinary”

Interestingly, Anne set these demanding goals and standards for herself, not due to any drill-sergeant-coded pressure from her family, but in spite of their Zen-like resistance to such pressure. As she described it, “my parents didn't really pressure me to do anything. Like, in my house, I kinda got the sense of, you know what? Everyone in this family is so creative… My mom's like, you girls, you're actually the smartest kids, you don't really have to apply yourselves. You'll just do great no matter what because you're creative and you're different.” Yet Anne observed the world around her and formed a contrary conclusion: that she could go much farther—in the sense of building a more vibrant, enjoyable life—to the extent that she did apply herself.

What became increasingly evident through our conversation was just how radically Anne’s motivation differed both from the stereotypical “corporate-ladder-climber” drill sergeant mentality and the “Bohemian” Zen mentality. It was not an anxious internalization of what counts as status or success. It certainly wasn’t viewing normal paths critically, as an inherent rat race. Anne saw something ordinary, and, in working to understand it, embraced it as her own.

When one has desires that are in the range of ordinary, it can be its own kind of challenge. We live in a culture that is especially bad at imbuing ordinary things with meaning. Status, sure, but meaning—moral approbation and spiritual importance—not so much. It is more common either to rebel against ordinary paths or to pursue them in a guilty and/or deliberately mercenary way. It takes a certain chutzpah to see a common path and learn to view it as the basis of a life fully lived.

Iterating on the vision

This difference in fundamental approach continued to manifest itself throughout Anne’s story. For instance, whereas someone on a default “ladder-climbing” path might have felt a pressure to go straight to law school immediately after college, Anne decided to take a year off after graduating from Cornell so she could experience the “real world” before going back to school. And because Anne longed for independence, she took a “bit of a risk” and seized on an opportunity: one of her college friends had moved to Boston and was looking for a roommate, so Anne moved in with her and took a job as a baggage handler at Boston Logan Airport. The job paid $9/hour (in Boston!), but it was “interesting and fun and I got to fly places for free.” Even so, Anne knew this wasn’t her final career destination. A year later she began law school at Tulane University in New Orleans—the “cool city” of her dreams.

Perhaps the biggest difference in approach was the one already mentioned: that Anne wanted to do something hard. She yearned for hard, good work. She saw it not as a mere means to an end, nor as something to do only reluctantly and minimally, but as something worthwhile, as part of the life she wanted. For her this just took the form of quiet, consistent diligence. “I never skipped class” in law school, Anne told me.

I didn't really volunteer in class, but I listened to everything, and I took great notes. Then I would go home, type up my notes, I would read every case twice that they assigned us to read one time just casually, and then a second time taking notes in a notebook. To summarize it and, you know, try to get all the points down that they were expecting us to get.

It wasn't a slog. I got absorbed in it because every case was, like, a mystery; what am I supposed to be getting out of this? What really happened?

It’s in the embrace and intentionality of such practices that fulfillment is born. A great many people go to law school for a great many reasons. The ones who end up happy are not necessarily extraordinary in the sense of being wildly successful lawyers. They are the ones who learn to love the work, to do things like think of studying as a mystery, as something worth being curious about. These experiences of exercising one’s agency to enjoy and persist on one’s path, day in and day out, are the stones out of which a life is built.

As a further case in point: Anne did not enjoy her first job out of law school, partly because there was a culture of cynicism about the work. The senior attorneys left early, and the junior attorneys were expected to work weekends—not because the work was really urgent, but just to be able to add to the invoice. “Now I happily work Saturdays or late at night because this is my project, and I like what I'm doing, and I wanna help my client”, Anne told me. “Back then, it felt like we were just churning to bill hours.”

So Anne left that firm after 3 years, despite not having another job lined up, and she took a year off to explore what she might want to do next. As she put it, “I needed that break to reset myself, kind of like I did between college and law school.” During that time she really connected with her love of New Orleans, especially in the wake of Hurricane Katrina; she even took some graduate classes in Urban Planning to explore how she might be able to support the city. In the process she also became more opinionated about what mattered to her in a work culture and what kinds of clients she wanted to serve.

By the end of that year, she had a better idea of what she was looking for: “I didn't have a plan about where I wanted to end up, but I knew the kind of thing I wanted to do… I wanted to protect and promote businesses that wanted to be in Louisiana, because I loved it there.” So she took a job at a New Orleans-based insurance law firm that allowed her to do just that: defend liability and property insurance companies against capricious lawsuits that risked pushing them out of the state and ultimately hurting the local businesses they insured. Anne had seen first-hand, in the aftermath of Katrina, that many insurance companies were being sued to pay for flood damages that, in her judgment, they had never agreed and should not be expected to pay. Moreover, she saw people using insurance claims as a cudgel to force other changes onto the city, like making it harder for bars to operate.

Anne came to like—not cynically, but earnestly—the idea of defending insurance companies, even the very concept of insurance itself. And this meant even more to her in a context where her favorite city’s economy and nightlife were at stake. Crucially, her new firm also provided “a different culture than anywhere I worked before. People showed up for work, they seemed pretty happy to be there… and they were very serious and non-cynical about what they were doing.”

In the years since, Anne has continued to grow and challenge herself in the kind of work she does—she worked in-house for a Montessori school network for a while, and now she’s working for a law firm where her job includes being a trial lawyer, defending her clients before a judge and jury. Her sincere engagement with everyday legal work, largely on behalf of the types of ordinary large businesses that seem so hollow to so many, has and continues to be the solid bedrock of a great and intentionally built life.

Best of all, when I shared this impression with Anne, she not only knew what I meant but supplied a bunch more examples of “career-typical” people living their best lives:

I meet people like that all the time, by the way, in different areas, because I represent a lot of different kind of businesses. I was talking to a truck driver and he was telling me how… they get together with other drivers, and they have lunches together and talk about the best way to do things. And, you know, how to rescue a car if it drives over a bridge and things like that. So there are people doing their jobs in creative ways…even ones you don't think about too much.

Hats off to that truck driver, I say, and may we all bring such extraordinary creativity and care to the jobs that constitute our life—however “ordinary” they may be.

For the unabridged version of Anne’s story, read the full transcript below.

Read more

Principles on display: The builder’s mindset as a third way; your life as the measure of all things; we build ourselves by building

A few weeks ago I went for a walk with Sahil Lavingia in San Francisco (in an affirming self-demonstration of the fact that you can just meet people). In case you haven’t heard of Sahil, he’s the CEO and founder of Gumroad, author of The Miminalist Entrepreneur, painter, and influencer who first built his massive following by telling the honest story of his failure to grow Gumroad into a billion-dollar company. That “failed” company has since helped creators earn over $1 billion dollars on its platform, by the way:

Anyway, as we walked and talked, Sahil filled me in on a piece of the story that didn’t make it into that viral essay, but that struck me as pivotal from a builder’s mindset standpoint.

After the disappointment of having to lay off his entire team to make Gumroad a sustainable business—which, by the Silicon Valley “go big or go home” startup ethos he had internalized, felt like a massive failure—Sahil retreated from the Valley for a while. He sought refuge in creative pursuits like painting and fiction writing, and even moved to Provo, Utah, to take a writing class at Brigham Young University with Brandon Sanderson (a fantasy author he admired). And he noticed that the people he met there were beholden to a very different sort of ethos than the one he had absorbed in the Valley—but they were beholden to it just the same.

The other students in his creative writing class stressed out about their performance in the class and whether it would sufficiently impress Sanderson, in much the same way Sahil had stressed out about his startup’s performance and whether it would sufficiently impress SF’s highest-status investors. His new friends in the Mormon community showed no concern for the growth of his startup, but showed great concern for the fact that he was not yet married. Where Sahil’s inner drill sergeant had been pushing him to fall in line with the Valley’s default template for success, their inner drill sergeants were pushing them to fall in line with BYU’s or the Mormon church’s default templates for success.

In smiling at these people’s obeisance to their culturally received templates, I suspect Sahil was able to see that his obeisance to his own culturally received template—the “build a billion-dollar venture-backed startup” template—was not the only nor the obviously best template for living a great life. And in seeing this, he likely developed a healthy skepticism of the notion that any given template could warrant blind obeisance for its own sake.

Thus inoculated against his inner drill sergeants, Sahil was free to consider what sort of life he actually wanted to build for himself, and then define his standards of success accordingly. Here is how he went on to describe the subsequent shift in his success criteria for Gumroad:

For years, my only metric of success was building a billion-dollar company. Now, I realize that was a terrible goal. It's completely arbitrary and doesn't accurately reflect impact.

I'm not making an excuse or pretending that I didn't fail. I'm not pretending that failure feels good. Everyone knows that the failure rate in startups—especially venture-funded ones—is super high, but it still sucks when you don't reach your goals.

I failed, but I also succeeded at many other things. Gumroad turned $10 million of investor capital into $178 million (and counting) for creators. Without a fundraising goal coming up, we're simply focused on building the best product we can for our customers. On top of all that, I'm happy creating value beyond our revenue-generating product (like these words you're reading).

In rethinking his metrics of “success” for Gumroad, Sahil grounded his criteria in what mattered to him, not just for this specific venture, but his life as a whole. For some ambitious builders, “building a billion-dollar company” is a valid goal, given the kind of value they thrive on creating and the kinds of dents they want to make in their world. As Sahil puts it in that same essay, “There’s nothing wrong with trying to build the next Microsoft” (and indeed, Bill Gates remains Sahil’s “all-time hero,” as he is one of mine). But Sahil is not Bill Gates; he is a creator who loves to write and paint and walk around discussing ideas (lucky me!) as much as he loves to code. And the company he has built, a platform for creators by creators, is perfectly suited to both express and support these values. (The same is true, by the way, of the new venture he’s building now). For instance, from his 2021 essay “No Meetings, No Deadlines, No Full-Time Employees”:

Instead of having meetings, people ‘talk’ to each other via GitHub, Notion, and (occasionally) Slack, expecting responses within 24 hours. Because there are no standups or ‘syncs’ and some projects can involve expensive feedback loops to collaborate, working this way requires clear and thoughtful communication.

Everyone writes well, and writes a lot.

There are no deadlines either. We ship incrementally, and launch things whenever the stuff in development is better than what's currently in production.

From 2011 to 2016, building Gumroad was my singular focus in life. But today, it is just a part of my life, like a hobby might be. For example, I paint for fun, and every once in a while, I sell a painting.

At some point, it clicked: Creators make money so they can make stuff, instead of the other way around. Why not adopt this framing at Gumroad, too?

This is what working in the creator economy should feel like.

If you follow Sahil on social media or read his writing, you’ll know he applies this level of fresh thinking and intentionality not only to his business but to the design of every aspect of his life. For instance, here he is responding to an interview question about his morning routine:

The first thing I do is either drop my girlfriend off at work and head to the gym, or shower.

I can’t function if I haven’t showered. I can’t go to the gym if I’ve already showered.

And here he is, in another interview, talking about his approach to painting:

One of Lavingia’s favorite hobbies is painting: he spends about 18 hours a week doing it. “If I have a really great painting, I celebrate it. If I don’t, I celebrate it,” he says. “It’s about this multi-year journey for me, improving my ability to paint.”

And, on what painting has helped him understand about building tech products:

There’s nothing that’s gonna teach you how to build stuff faster than building stuff. It’s just like painting.

This insight, as Sahil’s story so beautifully illustrates, scales all the way up to life as a whole. There’s nothing that’ll teach you how to live your life faster than living it—that is, living your life, undeterred by whatever local drill sergeants might try to pressure you into living someone else’s.

Builder spotlight #5: From “I ought to give up composing” to history’s greatest piano concerto in 3 short years (Sergei Rachmaninoff)

Principles on display: Your Flaws Matter Less Than You Think; Building Yourself by Building

The first time I fell in love, it wasn’t with a person, but with a piece of music.

I was 14 years old, and I was spending my summer on tour with the Blue Lake Youth Symphony Orchestra. The crown jewel of our concert program was Rachmaninoff’s 2nd Piano Concerto, played by a handsome pianist of 17 or 18 years old whose name was Brandon—and that’s literally all I can tell you about him, apart from the fact that he played exquisitely. I clawed my way to the position of “co-concert-mistress” just so I could sit in the front row of the first violin section and feel the uninterrupted sweep of chords descending from Brandon’s fingers straight up into my spine, as if enveloping me from within and bouying me up to where I could see the final, radiant triumph unfolding out of every passing darkness I would fight through over the course of my entire life.

Not only was the concerto my first love, but it has been among the most enduring. To this day, I can never listen to it casually in the background; it is too intensely intimate, too viscerally sublime an experience to admit of such dilution. 

And yet—perhaps implicitly fearing that Sergei’s life story would not live up to the grandeur and romance of his greatest work—I’d learned almost nothing of his biography until recently, when a friend mentioned him as an example of someone who had battled depression. This claim intrigued me enough to warrant the purchase of a recent biography, and, wow: if I’d set out to invent the most personally satisfying origin story imaginable for my beloved concerto, I couldn’t have come up with anything remotely this good. 

Not only did Rachmaninoff compose the 2nd piano concerto as a literal act of triumph over a 3-year depression during which he composed almost nothing; but he DEDICATED IT TO HIS THERAPIST. 

I don’t really go in for hashtags, but if ever anything could inspire me toward the eager exclamation of #LifeGoals, this would be it. 

In all seriousness: having reviewed the facts I summarize below, I don’t believe Rachmaninoff could have composed his 2nd Piano Concerto without the many-year struggle that preceded it; nor that he could have triumphed so fully over that struggle except by composing his 2nd Piano Concerto. 

Biographers typically date the onset of Rachmaninoff’s depression to the catastrophic failure of his Symphony No. 1 premiere in 1897 (more on this below). But to understand the premiere’s crushing impact on Rachmaninoff’s mental state, we need to start a bit earlier in the story. 

In 1893, the 20-year-old Rachmaninoff received news that his idol and friend, Pyotr Ilyich Tchaikovsky, had suddenly died by cholera. Rachmaninoff had already grieved the deaths of 2 beloved sisters—one of whom had introduced him to Tchaikovsky’s works—by the time he was 12 years old, and Tchaikovsky’s death likely had a compounding effect; all the more so given just how much Tchaikovsky’s support and recognition of Rachmaninoff’s talent had meant to him. Here is Rachmaninoff’s recollection of one of their first interactions (as quoted in Bertensson and Leyda’s Sergei Rachmaninoff: A Lifetime in Music):

“Timidly and modestly, as if he were afraid I might refuse, he asked me if I would consent to have my work produced with one of his operas. To be on the poster with Tchaikovsky was about the greatest honor that could be paid to a composer, and I would not have dared to suggest such a thing. Tchaikovsky knew this. He wanted to help me, but was anxious also not to offend or humiliate me.”

Upon learning of Tchaikovsky’s death, Rachmaninoff immediately channeled his grief into composition: within a month he had completed his deeply mournful Trio élégiaque No. 2 as a tribute. As he wrote to a friend:

• “This work is a composition on the death of a great artist. It’s now finished, so I can speak with you. While working on it, all my thoughts, feelings, powers belonged to it, to this song....I trembled for every phrase, sometimes crossed out everything and started over again to think, think. Now that’s over, and I can speak calmly. I wrote no one, not even the Skalons, whom I love sincerely.... You ask how things go with me? These days things go well only with priests and pharmacists.”

With the death of Tchaikovsky, Rachmaninoff not only suffered a great personal loss, but also the loss of the more famous composer’s public support and encouragement. Over the next several years, both his inspiration and his commissions ran dry. To supplement his income, he taught piano lessons, which he hated and approached as a dreaded chore (writing in one letter, “I am in general a poor teacher and today, moreover, I was unpardonably malicious”). His few compositions came in torturous fits and starts; after a month of working on a symphonic poem he would never end up completing, he wrote: “I was terribly tormented, and even threw away part of what I had written; worst of all, I may throw away all that I now have…” 

His financial situation got so desperate during these years that he began pawning some of his most prized possessions, such as the gold watch given to him as a symbol of renewed friendship by his beloved mentor Zverev. 

The one major work he did manage to compose during this time was his Symphony No. 1, on which he worked tirelessly (“about ten hours a day”) from January 1895 until its completion 8 months later. To this work he hitched, not only his hopes of financial success and renewed professional glory, but, apparently, his entire self-worth as a composer. Bertensson and Leyta’s biography describes how he “had put so much of himself into his symphony” that he “could not settle down to further serious composition until it was heard; his future work was to be determined by the public’s reaction to his symphony.” Rachmaninoff himself later recalled (as quoted in Rachmaninoff’s Recollections):

“I imagined that there was nothing I could not do and had great hopes for my future. It was in the confidence bred of this feeling that I composed my First Symphony in D minor, and the ease with which I worked encouraged my pride and self-esteem. I had a very high opinion of my work… The joy of creating carried me away. I was convinced that here I had discovered and opened up entirely new paths in music.”

And yet the symphony’s premiere was, in the estimation of every critic and, above all, Rachmaninoff himself, a disastrous flop. 

Even before he read the many scathing reviews, like the one famously proclaiming that his symphony would “enchant all the inmates of Hell,” Rachmaninoff was devastated. In a letter written weeks after the premiere, he wrote: 

“I’m not at all affected by its lack of success, nor am I disturbed by the newspapers’ abuse; but I am deeply distressed and heavily depressed by the fact that my Symphony, though I loved it very much and love it now, did not please me at all after its first rehearsal.”

Interestingly, most historians today blame the failed premiere on a poor performance by the conductor, Glazunov, who by some accounts may have actually been drunk. And Rachmaninoff seemed to reach a similar conclusion at the time: “[a]t present I am inclined to blame the performance,” he wrote in the same letter quoted above. Yet here is how Rachmaninoff described the whole experience years later, as quoted in Rachmaninoff’s Recollections: 

“According to my present conviction this fate [the symphony’s terrible failure] was not undeserved. It is true that the performance was beneath contempt and the work in parts unrecognizable, but, apart from this, its deficiencies were revealed to me with a dreadful distinctness even during the first rehearsal. Something within me snapped. All my self-confidence broke down, and the artistic satisfaction that I had looked forward to was never realized… I ‘listened in’ to my own work. I found the orchestration abominable, but I knew that the music also was not up to much. There are serious illnesses and deadly blows from fate which entirely change a man’s character. This was the effect of my own Symphony on myself. When the indescribable torture of this performance had at last come to an end, I was a different man… All my hopes, all belief in myself, had been destroyed.”

And: 

“I returned to Moscow a changed man. My confidence in myself had received a sudden blow. Agonizing hours spent in doubt and hard thinking had brought me to the conclusion that I ought to give up composing. I was obviously unfitted for it, and therefore it would be better if I made an end to it at once… (emphasis added). A paralyzing apathy possessed me. I did nothing at all and found no pleasure in anything. Half my days were spent lying on a couch and sighing over my ruined life…. This condition, which was as tiresome for myself as for those about me, lasted more than a year. I did not live; I vegetated, idle and hopeless.”

Reading Rachmaninoff’s own different accounts of his judgment and mental state after the premiere, I recognize a thought process common to many people whose basic self-worth has been shaken in some way: the spiraling back and forth between self-condemnation and self-justification,1 with neither narrative bringing full satisfaction or relief, and both only serving to suck the person farther down into hopeless, resigned passivity. 

Here are just a couple of illustrative excerpts from Rachmaninoff’s letters in the months following that premiere: 

“I'm starting, it seems, to suffer from a black melancholy. That's a fact. This melancholy. Today I cried like an idiot. I have not yet begun to drink vodka or wine at all, but I'm almost ready to give you my honest word that if my affairs do not change, I will start to drink. I'm very drawn to this.”

And:

“I will die by the end of the season of black melancholy. Look and weep more, come visit me at my grave.”

This was how Rachmaninoff passed the better part of the next 3 years, but for the intermittent distraction of a few musical endeavors tangential to composing (such as trying his hand at conducting, accompanying his great friend and opera legend Chaliapin on piano, and touring London with some of his earlier compositions). Meanwhile his friends and relations tried everything they could to bring him out of his melancholic apathy, even arranging for him to meet his literary hero Leo Tolstoy—whose “stereotyped phrases” of “You must work” and “Do you think that I am pleased with myself?” apparently did nothing to motivate or encourage Rachmaninoff (per his own account in a letter written years later). 

By January of 1900, Rachmaninoff had, according to Bertensson and Leyta, “become so severe in his self-criticism that completion and even initiation of any composition had become impossible.” So his aunt suggested he get some professional help. Specifically, she encouraged him to see Dr. Nikolai Dahl: a neurologist whose innovative therapeutic techniques—a mix of hypnosis and supportive talk therapy—had purportedly healed the mental afflictions of several people known to the family. 

Somewhat to the family’s surprise, Rachmaninoff assented to the treatment without protest. He visited Dahl every day for about 3 months, and by the end of that time he felt well enough to compose again. That summer he began work on his 2nd piano concerto, which premiered to thunderous applause in November 1901.

So what magic did Dahl work in those sessions to finally lift Rachmaninoff out of his depression and inspire him to compose the arguably greatest piano concerto in history? 

Here is Rachmaninoff’s own account of the work he did with Dr. Dahl (from Rachmaninoff’s Recollections): 

“My relations had told Dr. Dahl that he must at all costs cure me of my apathetic condition and achieve such results that I would again begin to compose. Dahl had asked what manner of composition they desired and had received the answer, ‘A Concerto for pianoforte,’ for this I had promised to the people in London and had given it up in despair. Consequently I heard the same hypnotic formula repeated day after day while I lay half asleep in an armchair in Dahl’s study. ‘You will begin to write your Concerto. … You will work with great facility. … The Concerto will be of an excellent quality. …’ It was always the same, without interruption. Although it may sound incredible, this cure really helped me. Already at the beginning of the summer I began again to compose. The material grew in bulk, and new musical ideas began to stir within me—far more than I needed for my Concerto.”

Likely this wasn’t the whole of Dr. Dahl’s treatment; according to Bertensson and Leyta, the hypnosis “was supplemented by general conversation, and as Dahl was a cultured and musically intelligent man, these talks must have enhanced the salutary effects of the treatment.” But it is to the hypnosis—i.e., the repetition of the same few mantras instilling in Rachmaninoff an expectancy that he’ll be able to get back to work and compose a great concerto—that the patient himself attributes his cure. 

From what we know today about placebo effects, common factors in therapy, and the importance of positive expectancies, we can at least form a reasonable conjecture as to the key ingredient in Dr. Dahl’s cure: his professional credentials and confidence in his own treatment gave Rachmaninoff permission to stop ruminating over Symphony #1 and get back to the work of creating. Then the creating itself did the rest. 

Notice what Rachmaninoff’s treatment didn’t involve: namely any sort of explicit “shadow work” or resolution of the questions that had been eating him up for years regarding the causes of his spectacular failure. Instead, I surmise, Dr. Dahl’s simple daily mantras pardoned Rachmaninoff from the felt need to seek some grand redemption for the “sin” of his failed First Symphony before permitting himself to value his life and work again. And as it turned out, no such grand redemption was needed. The unspoken message, as I might’ve articulated it had I been his therapist, was: so what if your symphony sucked? It probably did suck, like most first symphonies probably suck; which is all the more reason to get back to work, hone your craft, and write more music you can love.

In short-circuiting his ruminations and getting back to the work of composing, by the way, Rachmaninoff was able to achieve a far more objective and constructive view of his failed Symphony with time. Here’s how he writes of its merits in a letter dated 1917: 

“Before the Symphony was played, I had an exaggeratedly high opinion of it. After I heard it for the first time, my opinion changed, radically. It now seems to me that a true estimate of it would be somewhere between these two extremes. It has some good music, but it also has much that is weak, childish, strained and bombastic.” 

So the next time you need an elevated perspective on the weak, childish, strained and bombastic in your own work, just think of Rachmaninoff’s story. And if ever you struggle to recall the full meaning and essence of that story, you need only listen to his 2nd Piano Concerto. 

Principles on display: Your life as the yardstick; finding person-life fit; building yourself by building; build YOUR perfect life

Keeping with the theme of Amazing Esthers, today I want to spotlight the iconic Estée Lauder (born “Josephine Esther Mentzer” to Hungarian Jewish immigrants in Queens; she later added the accent over the “e” to lend elegance and sophistication to her brand). 

Listening to David Senra’s recent Founders Podcast episode on Estée’s 1985 autobiography, A Success Story, I noticed a funny parallel to Loyal founder Celine Halioua (the first builder to be spotlighted in this series). Just as Celine reflected that she would not have been able to sustain motivation for her canine-focused biotech startup had she not herself been a dog lover, so Estée reflects in the book (this and all excerpts below as quoted by David, and all emphases added by me): 

I sometimes wonder if I had set my heart on selling tassels, cars, furniture, or anything else but beauty, would I have risen to the top of a profession? Somehow I doubt it. I believed in my product. I loved my product… A person has to love her harvest if she's to expect others to love it. And beauty was such a bountiful harvest.

But unlike Celine, who views the mission of extending dogs’ lifespans as a stepping stone—albeit an important and largely rewarding-in-itself stepping stone—toward her ultimate mission of advancing human longevity, Estée had no further endgame: a life devoted to evangelizing beauty, as she saw and understood it, was the endgame. At a time when women were generally expected to be homemakers, Estée was “a woman with a mission. I had to show as many women as I could reach not only how to be beautiful, but how to stay beautiful.”

This was, for Estée, nothing short of a holy quest.

Here are just a few excerpts that paint a picture of how and why she chose this quest, and what it meant to her:

Beauty is a fine invention, if the truth be known. The skilled woman can invent beauty over and over again with extraordinary effect. The art of inventing beauty transcends class, intellect, age, profession, geography— virtually every cultural and economic barrier. There isn’t a culture in the world that hasn’t powdered, perfumed, and prettied its most adored and fabled women, its most respected women. Love has been planted, wars won, and empires built on beauty. I should know. I’m an authority on all three. Love, wars, and empires have been woven into my personal tapestry for decades. I’ve been selling Beauty ever since I could recognize Her.

And on a more intimately personal level:

[B]eauty is the best incentive to self-respect. You may have great inner resources, but they don't show up as confidence when you don't feel pretty…. The pursuit of beauty is honorable.

She traces this love of beauty back to her earliest memories:

My very first memory is of my mother's scent, her aura of freshness, the perfume of her presence. My first sensation of joy was being allowed to reach up and touch her fragrant and satiny skin. Her hair didn't escape my attention, either. As soon as I was old enough to hold a brush, l'd give her no peace.

As a young girl “mesmerized by pretty things and pretty people,” Estée would experiment with painting and touching up the faces of anyone who’d allow it:

Even at eight, being fashionable, being feminine, being different, was a reason for me…

All of this annoyed my father considerably. ‘Stop fiddling with other people's faces,’ he'd say.

But that is what I liked to do—touch other people's faces, no matter who they were, touch them and make them pretty. Before I'm finished, I'll set, I'm certain, the world's record for face touching.

At that time Estée passively dreamt of becoming an actress someday, but had no conception of turning her love of beauty into a business career (if she was to have a career at all; recall that most women in her day did not). Then came a pivotal encounter with her uncle, John Schotz, who turned her flicker of youthful interest into a lifelong flame:

My shining moment came in the form of a quiet, bespectacled man who also loved touching faces.

Uncle John Schotz, my mother's brother came to visit us from Hungary. He was a skin specialist. What glories those words conjured up!

Estée’s story of apprenticing herself to her Uncle John is instructive for any of us wishing to light a spark within the young people in our lives:

He captured my imagination and interest as no one else ever had. I was together with Uncle John. He understood me. What's more, he produced miracles. I recognized in my Uncle John my true path. He produced his glorious cream in our home, working happily over a gas stove. I watched and learned, hypnotized.

This is the story of witching. I was irrevocably bewitched by the power to create beauty. Uncle John had worlds to teach me.

We constructed a laboratory of sorts in the tiny stable behind the house. My parents installed gleaming linoleum on the floors and walls. We set up a table, where I watched my uncle mix his magic.

Do you know what it means for a young girl to suddenly have someone take her dreams quite seriously? Teach her secrets? I could think of nothing else. After school, I'd run home to practice being a scientist. I began to value myself so much more, trust my instincts, trust my uniqueness. Trusting oneself does not always come naturally. If learned when young, the practice sticks. Today, there is no one who can intimidate me because of title or skill or fame. I do what's right for me.

Thus Estée came to see that her most personally valued activity—creating beauty—need not get relegated to a mere frivolous pastime, but could constitute serious, credible work. She saw that she could build real knowledge and provide real value to people in the process:

I didn't have a single friend who wasn't slathered in our creams. If someone had a slight redness just under her nose that was sure to emerge into a sensitive blemish the next day, she'd come to visit, I'd treat her to a Creme Pack—voilà!—vastly improved skin the next day. …Friends of friends of friends appeared…. My reputation among my peers at Newtown High School grew by leaps and bounds.

And, even more fundamentally, she came to see that what she values is real and important in its own right; that her dreams deserve to be taken seriously.

Deep inside, I knew I had found something that mattered much more than popularity. My moment had come and I was not about to miss seizing it. Uncle John loved me, I loved him, and my future was being written in a jar of snow cream.

This newfound conviction never departed her. Even as a 25-year-old wife and mother struggling to make ends meet, she continued to run her beauty experiments in earnest:

Times were lean. About two years after our marriage, we had a beautiful son, and I spent my days mothering Leonard. And all the time, all the time, I was also mothering my zeal for experimenting with my uncle's creams, improving on them, adding to them. I was forever experimenting on myself and on anyone else who came within range.

Good was not good enough—I could always make it better. I know now that ‘obsession’ is the word for my zeal. I was obsessed with clear glowing skin, shining eyes, beautiful mouths.

It was never quiet in the house. There was always a great audible sense of industry, especially in the kitchen, where I cooked for my family and during every possible spare moment, cooked up little pots of cream for faces. I always felt most alive when I was dabbling in the practice cream.

I felt as though I was conducting a secret, absorbing experiment—a real adventure.

Even when she wasn’t cooking up her beauty creams, Estée was hardly playing the dutiful housewife: instead, she was chasing after every conceivable opportunity to demo and sell those creams. The way she describes the product presentations she gave in beauty salons, at hotels, in women’s homes over a game of bridge, reads uncannily like a love affair:

The mood at these sessions was as exhilarating for me as for them.

I didn't need bread to eat, but I worked as though I did… from pure love of the venture. For me, teaching about beauty was and is an emotional experience. I brought them charisma and knowledge about their possibilities. They gave me a sense of success. I felt flushed with excitement after each session… Business itself was the purest romance for me.

Elsewhere Estée again analogizes her experience of building the business to a passionate romance:

Business is not something to be lightly tried on, flippantly modeled. It's not a distraction, not an affair, not a momentary fling.

Business marries you. You sleep with it, eat with it, think about it much of your time. It is, in a very real sense, an act of love. If it isn't an act of love, it's merely work, not business.

As you might expect from these descriptions, Estée’s devotion to her beauty business put a strain on her actual romance; after 9 years of marriage, she and her husband Joseph got a divorce. As Estée explains in the book, she was “married very young,” and she thought she might have “missed something out of life.”

What you might not expect, however, is that their story did not end there: four years later, Estée, having realized she had “the sweetest husband in the world,” re-married Joseph—and this time she made him an equal partner in her business. A year later their second son was born, and both of their sons got involved in the business as well. Leonard, who eventually became CEO and helped grow the company into the global cosmetics empire it is today, recalled affectionately in a 2020 CBS interview how he forged his own identity and self-confidence through his early days helping out with the business: “We had a little tiny factory, and I would go there after school for 25 cents an hour and I'd work.” As he reflects in his own memoir, excerpted here, “The company and I grew up together, our lives as closely paired as twins. It has always been more than a family company: it was—and continues to be—my family.”

So it turned out that Estée didn’t have to choose between her love of beauty and her love of Joseph and her sons. Instead she could fuse her loves together, uniting her whole family around a shared mission worthy of animating all of their beautiful, fully-lived lives. 

There is much more to learn from the story of how Estée built her empire, most of which I’m omitting here; go listen to David’s recent episode (as well as the earlier episode he devoted to the same book 3 years ago), or buy the book (warning: it’s pricey!) if you want to go straight to the source.

Catch up on prior installments:

Introduction to the series

Builder spotlight #1: “Must Love Dogs” (Celine Halioua)

Builder spotlight #2: “Mr. Lazy” (David Allen)

Builder spotlight #3: The Right Kind of “Crazy” (Esther Crawford)

Principles on display: self-honesty as the foundation for self-trust; agency is what makes us human; your life as the measure

I’d been wanting to sit down with Esther Crawford ever since I saw her legendary tweet about the time when she went against conventional wisdom and put her own savings into her startup.

My first encounter with this tweet was through Paul Graham’s quote tweet commenting on it:

For my part, I thought Esther’s story sounded like a great example of a builder’s willingness to bet on her independent judgment. But I also wondered what it was about Esther’s context at the time that would have warranted such a judgment—since it would in fact have been a foolish move in many similar circumstances. Did she have a backup source of financial support in case the company failed? Was she seeing early signs of traction that were clear from her customer conversations but hard to communicate to investors? Or was it in fact a foolish decision that simply looks good in retrospect due to survival bias?

I asked Esther these questions over bagels last week, and her answers impressed and inspired me beyond anything I could’ve hoped for. Here’s some of the additional context Esther shared about her story:

Despite being a single mom with 2 young kids at the time, she did not feel especially threatened by the prospect of burning through her savings; she knew that in the worst case scenario, she could simply get a job. In fact, she had done the same thing once before for a prior startup she’d also cofounded, and that time she did lose the money—and it was fine. It probably helped that she’d grown up quite poor and had managed to stay resilient through all sorts of family drama, from being kept secret by her biological father until age 7, to finding out her stepfather was sentenced to life imprisonment when she was 13. So the prospect of needing to watch her spending for a while did not exactly intimidate her.

This was by no means the first time Esther had made an unconventional decision that worked out well for her in the long-run. Here were a few others:

• As a 21-year-old college student trying to lose a bunch of weight, Esther was dealing with a lot of shame about her body and yet knew she needed accountability. So she joined the predominantly much older crowd of people using Weight Watchers at the time, and started posting videos about her weekly progress on this small and esoteric (and thus, she figured, relatively anonymous) new video platform called YouTube. Her videos started gaining popularity with increasing numbers of viewers who found them inspiring, and eventually caught the attention of both the YouTube and Weight Watchers CEOs, who recruited her to help them promote their respective businesses in this new age of online video content.

• As a graduate student studying International Relations and looking for new ways to explore her interests in online media and film, Esther looked on Craigslist and found a receptionist job at a film production company. She figured this would be a good way to get her foot in the door and learn more about the industry—and she couldn’t have been more right. The skills and contacts she picked up at that company became the launchpad for what essentially became her first startup.

• As a 29-year-old with 2 kids and a husband of 10 years, Esther realized her professional ambitions required her to move to San Francisco. So she said to her husband, “I am moving to SF with the kids, and you can either join us or not.” He did join them, however reluctantly, and they amicably divorced sometime later.

• Today Esther and her ex-husband are both remarried and their 2 families are great friends, facilitated by the fact that Esther bought them both homes across the street from one another many years ago—another unconventional decision that has worked out beautifully for all parties, thanks to the years of earned trust and understanding between them.

Some months after Esther’s decision to put her own savings into the startup, she finally managed to raise a round of venture capital, only to realize a few months later that the product they were building—which involved, prophetically enough, interactive AI personae—was about 5-6 years ahead of its time. (She was right; this was 2017.) So she made the hardest professional decision she had ever made up to that point, and told one of her lead investors that the product they had just invested in was not going to work.

The investor was flustered by the news at first; then, after 3 hours of open, honest conversation, that investor looked at Esther and said, in effect: “look, I invested in you, and I believe in you now as much as ever. Whatever it is you decide to build, I will gladly back it, and will give you more money the next time you raise.” 

Esther spoke of this conversation, more than the initial decision to risk her own savings, as a critical inflection point: she had chosen to be completely honest with herself and her investors about a judgment that pained her to form, and the result was greater rather than lesser trust, both from herself and them. From that day on, Esther said, she never had any difficulty fundraising for her startups or making unconventional but values-aligned decisions for her own life and career. Her judgment had been tested in crucible after crucible, and it had stood the test of experience and time. 

After Esther told me this story, I expressed how much I admired the courage and independence of judgment she’s shown at so many junctures in her life. She mused that perhaps she had been driven by a need to “prove herself” to the people who rejected and dismissed her early in life; but I submit that such an interpretation wouldn’t do her credit.

A need to “prove oneself” to internalized authority figures leads to things like climbing conventional status ladders, or staying in an unhappy marriage, or piling up as much money as possible to preserve the appearance of having “made it”.

What motivated Esther to do things like take a receptionist job at a film company, pick up her life and move to San Francisco, and risk her savings on her startup was something far more personal and idiosyncratic: a conception of the interests she wanted to explore, the people she wanted to meet, the products she wanted to create, the life she envisioned and wanted to build for herself—and, yes, the proof that she really could count on herself to do it.

Welcome to my favorite new bite-sized blogging experiment to date: a series of psychologically-illustrative narrative snippets from the lives of amazing builders. Because the only way to really understand and internalize the “builder’s mindset” (or really any universal prescription for living) is to see its inexorable logic play out in the context of many particular lives and narrative arcs.

I feel particularly excited to launch this series today, after having just spent 2 days among some of the world’s most thoughtfully ambitious builders and champions of building at the 2024 Progress Conference in Berkeley, CA. The first “builder spotlight” below offers one small glimpse into the kinds of inspiring humans and building endeavors I encountered there.

I hope you’ll enjoy this first pilot installment of “Fantastic Builders and Where to Find Them”, and I welcome any and all feedback on how to make it better. The stories that get the most love will likely get expanded on in my forthcoming book, so please let me know which ones really resonate (and feel free to point me toward other builders I should feature!).

Builder spotlight #1: “Must Love Dogs” (Celine Halioua)

Principles on display: Your life as the yardstick and finding person-life fit

Celine Halioua, the 30-year-old firebrand founder and CEO of Loyal, is one of the purest examples of practical idealism that I’ve ever had the pleasure to encounter. Her long-term ambition is to increase the human lifespan through anti-aging drugs. This is notoriously hard for a million different reasons, some of them regulatory (the FDA doesn’t like approving experimental drugs for non-disease targets), some economic and structural (e.g., it takes 20-30 years to see if a human anti-aging drug is working). But instead of giving up or getting cynical, Celine found an ingenious path forward: start by extending the lifespan of dogs, and establish a precedent for the human use case from there. 

Whenever I hear Celine speak, her boundless energy and optimism belie the enormous complexity and multi-decade time horizon of the mission she’s taken on. How does she do it? And how does she stay so cheerfully patient through all the regulatory and bureaucratic hurdles that have forced her onto this circuitous path to begin with? 

The simple answer is that this path has been anything but “forced” on her; she chose it, indeed custom-crafted it, based on the sum total of her values and proclivities. During the talk she mentioned that she happens to be a dog lover, and afterward I asked her whether she would’ve been able to sustain the same excitement about this path if she hadn’t been. “No,” she said, after a moment’s reflection. “I’ve actually come to love dogs and dog owners even more since I started this,” she continued, smiling with delight as she described her conversations with prospective customers and the lengths to which they’re willing to go for the chance of a few extra years with their beloved pet. 

This is the big secret behind Celine’s seemingly infinite reservoir of energy and enthusiasm: she has charted a path that she can love, with her own life as the ultimate yardstick.

Builder spotlight #2: “Mr. Lazy” (David Allen)

Principle on display: Building yourself by building

Many people have positively shaped my life, but there’s only a handful—maybe 3 or 4 among those still living—whose ideas have fundamentally transformed my life for the better. David Allen, the creator of the Getting Things Done (GTD) system I was lucky enough to discover back in college, is among that handful. Beyond the many well-documented wellbeing and productivity benefits of GTD, its most personally meaningful benefit was its role in helping me build and maintain self-trust. By providing a reliable method for capturing and tracking our intentions and choosing whether, when, and how we want to act on them, GTD makes it both harder and less necessary to BS ourselves about what we intend to do.

And so you can imagine my barely-containable delight when I got to spend 30 minutes picking David’s brain in a 1:1 Zoom call the other day. (Thanks for making the intro, !)

David spoke—and listened—with the calm, easy manner of someone who’s living his best life and knows it, and so feels no need to prove anything to anyone. You’d never guess from his mental spryness and casual demeanor that he’s either a day over 60 (he’s 78) nor the same guy whose work has transformed how millions of people and organizations around the world relate to their work.

Here are some tidbits he shared about his backstory and how he went from being penniless and hospitalized for heroin addiction (a story you can read more about in this Wired piece) to becoming the world’s most sought-after productivity expert and executive coach:

For all the immense success David has enjoyed as a result of Getting Things Done, he never actually set out with any sort of “grand plan” of transforming how people work or achieving any sort of large-scale influence. “I’ve never been that entrepreneurial,” he said; rather he’s always experienced himself as “just putting one foot in front of the other.” For instance, after the “self-exploration” journey that led him to drop out of his UC Berkeley PhD program, take up heroin, and eventually hit rock bottom, David needed to pay the bills somehow. So he started taking odd jobs wherever he could find them. (One of his first jobs, he recalled, was driving a delivery truck for a company making small industrial tools for some of the first “startups” in what eventually became Silicon Valley.)

Some of David’s friends at the time were starting their own small businesses, and they needed help “managing their systems”—i.e., getting themselves organized. David was always “Mr. Lazy” (his words) and liked the idea of making things more efficient. So he’d spend some time helping one friend get organized, then he’d “get bored, move on, and find another job,” and so on. At some point he learned that the types of jobs he was doing were called “consulting” (not a category he’d ever encountered growing up in Louisiana), and that he could get hired to do more of them. Then “some corporate guy saw” what David was doing for these small business executives and said “we need this for our whole team,” so he asked David to do a training for his company, which then got picked up by other companies, including Lockheed, where it was “one of their most popular trainings.” “Who’d have thought I’d end up in the corporate world?”, David mused. Consulting eventually turned into coaching for top executives, who would hire him to come to their office, sit desk-side with them, and help them implement the system he had come up with. It was 20 years later that someone said to him, “David, you’ve gotta write the book.” And it was another 4 years before he’d gotten the book written and “out of his head,” with little expectation as to how it would sell.

The rest, as they say, is history.

If you need a free and easy GTD start guide, by the way, Tyler DeVries has written a good one.

And that concludes the first installment of “Fantastic Builders.” Let me know what you think, and stay tuned for many more to come!

Lately I’ve been struck by the many and wondrous ways to be a builder. For instance, as I wrote in Being entrepreneurial about entrepreneurship:

For some people, in some circumstances, [being entrepreneurial about one’s life] might mean taking a job within a well-established institution like McKinsey; for others it might mean going outside established institutions and starting something new, with or without investor funding; for others it might mean going to school, or taking time off to raise kids, or waiting tables to make ends meet while learning to code or auditioning for acting roles or working on a novel. No one is ultimately more qualified than you to judge what particular path to take, or what advice to follow, or what institutions to accept or reject. Just stay awake to the fact that it’s your life on this earth you are building—and then choose accordingly.

And as I further elaborated in Your flaws matter less than you think:

Keep in mind that the concept of a “flourishing, fully-lived life” is abstract. Its universal demands are at the level of things like the need for self-honesty and the exercise of our agency. Beyond these fundamentals, thriving does not have one specific look. A life devoted to the single-minded pursuit of a passion at significant cost to personal relationships or physical health (a la Marie Curie, for example) may be just as “perfect” as a quiet life largely centered on cultivating strong, healthy family relationships, or a life of bustling variety, or any number of other sorts of lives… By contrast, one of the failure modes that precludes a “perfect” life is the passive (i.e. non-agential) adherence to some sterile, generic template of a “good life,” instead of custom-building a life that fully leverages your own inimitable mix of affordances and constraints and idiosyncratic conditions for thriving. 

In addition to this between-person variability in the lives builders build, I’ve been reflecting a lot on the within-person variability to which impressive and interesting people are often prone. Being truly ambitious about your life means you’re highly selective about where you channel your ambition at a given point in time—and you allow this to change according to what your fully-lived life requires.

Thinking back on my Founder’s Mindset podcast conversation last year with the exceptionally self-reflective Brett Kopf, co-founder of Remind.com and Omella, I keep remembering new ways his personal story embodies this theme. Brett’s motivations for starting his two companies, the approach he has taken to building and growing each one, the manner in which each one slots into and intersects with his personal life—these two epochs of his founder journey couldn’t be more different, yet both are profoundly inspiring and both bear his unmistakable signature.

Here are some illustrative excerpts, with the full transcript below (for paid subscribers):

Brett 1.0: serving 30 million users, going to therapy, watching dad die

The first part of the conversation focused on 22-year-old Brett’s dizzying experience of building and growing Remind.com—a messaging platform that 80% of U.S. public school teachers now use to communicate with their students.

For some cultural/economic context, Brett and his brother David co-founded the company in 2011, when messaging was new and venture capital funds were flowing into high-growth, high-risk tech startups.

And grow they did: Bret recalls “adding 200,000 to 350,000 users a day, 85% of which we would retain. Faster than Facebook, WhatsApp, at the time of growth.”

What motivated the young Brett to build Remind.com?

I was diagnosed with a slew of learning disabilities when I was a kid. And I pretty much spend the next, call it 16 to 17 years in my life, feeling not smart in school. And that was mostly because the structure and the system that I grew up in - and I went to a wonderful public school—it just wasn't fit for me. I was just a bit different. And I would be taken out of exams and classes, and I would have extra time, and I would have a special teacher to help me on things, and then the undercurrent—the emotion of what that made me feel—was not smart. Now I feel smart, now I'm very confident with who I am and who I'm not as an adult, but for a very long time it was difficult to figure out. And so that sort of energy of feeling not smart propelled me to start my first company.

Why specifically a messaging platform for teachers?

So tactically, Remind is like Slack for education. I wanted it because I had this teacher that totally changed my life. She sent me—well, what she really did was like she cared about me a lot, but I noticed that she was struggling to communicate with our students. And so I tried to solve a problem for her. And Remind then became very big… and I learned a lot about the world just being thrown into the deep end.

What were some of the things he learned?

…Emotionally, I wanted to prove so badly to the world that I wanted to build something that was highly impactful on a very large scale, that I would have this energy or this lifeforce inside me that would make me work my rear end off… I would work really, really hard, and I also wouldn't prioritize things that mattered. Now, what matters to me now is my emotional and physical health, my family, my nuclear family, and then my company, in that order. But when you would have asked me when I was 22, or 21, it wouldn't have been that, probably because I was young and naive. And I just sort of hadn't lived enough and been through experiences. And so because I didn't feel smart, there was this emotional propellant to want me to prove to the world—aka probably my father, who has since passed—but, like, prove to him that I could be something, and live up to his expectations. At the time, I had no idea that I was doing that, like, that I had that drive, though, because I wasn't aware of that.

How did he learn them?

I first started seeing a therapist… when I was living in San Francisco building my first company…. His name was Garrik, he was amazing, and one of the things that I felt like he was really helpful with was being a very safe, transparent, reflective mirror to my conscious and unconscious mind. And one of the things that he always explained to me is like, it's really hard to figure out why you are the way you are, and do things that you do.

At the time my dad was dying... [right] at the time of [rapid company] growth. It was crazy, [we] raised a ton of money, whatever, all of that stuff. So there was a huge amount of pressure, self-induced, but also just to perform in the world, especially because our customers needed it. And there [were] all these personal things that were happening in my life at the time, too. So, my dad had Parkinson's, and he was sort of on his downfall…. And for me, it was helpful to categorize the big problems in my life [in therapy]. One problem was like trying to reconcile the death of my dad. No, he wasn't dead at the time, but he was on that path. The other problem was trying to decide if I was ready to get married to my now wife, which thank God I did, but that was really hard. But I didn't know, which he helped me figure out, that my dad dying and kind of coming to terms with that was sort of a mental block to me even getting to the point that I can be ready to take that next step with my wife…. [H]e helped me structure those things and understand the realness of them. Like, you know… when the company was growing so fast, it was hard to even take the time to consciously say like, "well, your dad's dying right now”… And so he gave me that space, that structured space and time to do that. And we would talk about those things and understand how it was making me feel.”

What was it like to process all this while scaling to 30 million active users?

When like my dad had Parkinson's, there got to be a point where he could hardly move, he could blink his eyes as a yes or no. It's like the worst torture that you can imagine for a human, and for a loved one to see. And to compartmentalize and decouple the things that were happening in career life versus personal life is brutal, especially for a 22 year old… As an entrepreneur—look we have a lot of customers who did really care about me as a human, but at the end of the day, it's not their responsibility to necessarily care that I have this very real personal thing happening. When they send a text message, and they relied on my service and Remind to do something, and it had to do that thing. That's just the reality of it. And so [I’m sharing this] because there's like the surface level as an entrepreneur, what you're doing building something for the customer, and you have employees - but then there's the personal undercurrent of all the things happening in your life good, bad, or ugly, which are inevitable - and everyone goes through something - it's very difficult to manage both of those. And they are both true. Meaning I had to somewhat handle my personal life, and you have to execute at a very high level for what was demanded of me for my company.

Does he regret how hard he worked and how little time he reserved for family at the time?

No… I think that, given the skills that I had at that point (and I have more skills now because I'm more experienced), I don't think I had the emotional or physical capacity in the day to do other stuff.

Where does that additional capacity come from?

I think there's probably a mixture of time and experience. And like, I've just seen a lot of things, and you have a lot of shots on goal. And then my son—like when I had my son—he's almost two years old—for me it put a new perspective on what matters and why.

Brett 2.0: Building wisdom, reaping joy

Then, after Rewind.com had grown huge and Brett’s father had died, he took a step back and consciously re-prioritized his life:

I stepped out of a day to day operating role in my first company, I took a year off and I traveled with my wife for some of that time, and I kind of reevaluated what the heck just happened. And then what qualifies [as] a happy fulfilled life for me—I say me because everyone's different. And what I decided was thematically, there is my physical, emotional health, the relationship I have with my very close family, specifically providing for my wife, and with my son, and my dog. And then you know, my mom, my brother, the close people, and then it's the company. But I reprioritized my life out of all of that. And I could not have done that [during the Remind.com epoch]. I just wasn't mature enough.

So what motivates him now?

Well, I now prioritize everything that I mentioned. It's like health, family, then company; everything is revolving around that. And I don't care what external figure wants me to be another way, I just don't care. External figure could be a VC or like the press, I just don't care. Like, because I care more about providing or being with my son, than I would be on the cover of Forbes. I cared about being on the cover of Forbes when I was 21, I don't give a sh*t now, excuse the french. Unless it helps us acquire a bunch more customers, because that's what we're focused on now….

Let me be clear on that: I want to build Omella, I want it to be very large and very impactful, someday as big as Remind is. I do want that. And I get up every morning at 4:30 in the morning to grind a few hours in the morning before my kid wakes up so I can help him get ready. And then I go back to work. And so I still work very hard. But I'm not willing to sacrifice. So what that means is, probably at like four or five o'clock I stop working and I spend the next four or five hours with him. It also means that I spend one hour during the day exercising.

What does this mean for his approach to the business?

One from just a pure business standpoint is I want to have a business with strong, what you call basic business fundamentals and clear unit economics, which always come back to, do your customers come back? Do you have healthy retention? Do you have a high margin? Do you have high engagement? Are you growing in a healthy manner? Meaning are you making more money than you're spending, and having a good business model so you could be running the company forever? Like, that part's really important to me. Part of the reason is because with Remind we didn't charge for a long time, I think for that company it was right, just because we were growing so quickly. But I [now] want to build a company, and before it was maybe more of just a product.

And then there's the value systems of how we build it…. right now it's kind of a scary time, there's layoffs happening right and left, and valuations are getting slashed by 80%, but I think some of it’s good because it gets back to truth and clear fundamentals. And it's like, put up or shut up, if you're not going to build something that's valuable that a customer wants, probably the company's gonna die. And it won't be the end of the world, and you're gonna learn from it, and maybe you'll build something else, or maybe join someone else… For us, at Omella, our economics are clear. We make money on every transaction, but now it's like, how do we get to break-even profitability as fast as thoughtfully possible.”

What’s remained constant about his motivations as a founder, and what’s changed with experience?

[What I love is] talking to customers and deeply caring about them and wanting to help them, [in] this niche that is very big that no one knows about… I love that more than anything [and have loved it since Remind.com]. But then there's a set of value systems that apply that I believe are right, that [are] different from the old version of me, version one. Which, maybe if you went to business school—which I didn't, I studied agriculture and I nearly dropped out of school—they would teach me, but it's like clear fundamentals on what is a good healthy business, and wanting to do it for the right [reasons].

So let me give you an example. For this new company, Omella, we raised like, I don't know, four or five million bucks. Every single investor that came in, I said this will not be an overnight success, you have to be with us for like 10 years. You should not expect liquidity for 10 years. And if you want liquidity faster, please don't invest in the company. By the way, we don't need your money. And setting those expectations upfront was really important. Because we only wanted people who weren't going to be knocking on my door every day. A lot of this confidence, by the way, comes from just doing it a few times and knowing what I believe to be right and true in the world. And knowing that if I'm wrong, I'm gonna admit it, and I took a shot at gold and I tried.

What does he still struggle with?

…I have my career identity where I want to build something really impactful, and I have to work a lot…. And I think the company needs it. And also I want to spend time with my son and my wife, and I want to exercise and do the things I want… And unfortunately, one thing that scares me a bit is that I don't know too many public figures - and maybe this is just because the ones that aren't public are busy with their personal life or working—that have figured out both, where financially the things that they have built in the world are very impactful, and they have a very intentional, good personal life. Usually it's like crazy workaholics that are really not good personal life. And I don't want that.

….The [other] thing that I'm not necessarily as good at is managing my emotional state…. I was talking about it with my wife this week, it's like ah man, it's either I'm working, and I wonder what my son's doing right now, or I want to be with him, or I need to exercise. Or when I'm exercising—unless I'm playing basketball, because then my mind turns off, which is great—but if I'm lifting weights, it's like, “oh gosh, I have to answer this support ticket." So it's still hard; I'm still conflicted on both, because at the end of the day, I want to build something that's very big and impactful. Just for me personally, I'm not okay just building something that is sort of average, because I see this vision and I want to help these customers, I really do, I really want to have that impact and help them.

What are his overall takeaways for anyone wanting to build (a company or a life)?

[W]hen you build a startup it's really simple, you talk to customers a lot, you solve a simple problem for them, and you build a product that solves their problem, and you iterate rigorously. I spoke to 500 customers before we wrote a line of code. And so like that general framework is how I build all my companies. There's a lot that falls underneath that, but that's it. Just like talk to customers. Listen with two ears and one mouth, build a simple product, and solve a problem. That's like the framework in which I start the company.

The personal stuff, that's super hard. I don't know if I have any [takeaways], other than like, know thyself. I remember my dad, when he was actually passing, which I could not literally hear him. Well, literally I could but metaphorically, I couldn't. Where he said, "you know, Brett… all work and no play makes Johnny a dull boy.” …And all I hear was like, "yeah yeah Dad, whatever, like, I gotta grind, I gotta grind, I gotta grind." And it's like, oh wow, I'm 36 now… and it's like, oh, you know, you kind of see 50, and kind of see 75 and 100, and it goes really fast. And once you have kids… you know how fast it goes. And he had an interesting point there.

Now, at the time I couldn't do anything with that, because I was so focused on [being] ambitious and growing. And I'm still super ambitious, but also life goes really quickly. So it kind of goes back to this point that you made about knowing yourself or that we've been talking about, knowing what you want and why, and making sure you're doing it for yourself and not someone else. I was doing my first company for someone else, little did I know it. But this company is not for someone else other than our customers of course, but the internal drive, there's a clear foundation for that.

My own takeaway from Brett’s takeaway: whereas building a company is about getting to know your customer and creating a product they want, building your life is about getting to know your whole self and creating a life you want—companies and families and fitness routines and all. Big pivots are expected.

Full transcript below (or listen to the full episode here).

Alice Bentinck  00:18

Welcome back to The Founders Mindset, the podcast where we deep dive into the psychology of founding a company, through the personal stories for the founders themselves. I'm Alice Bentinck, co-founder of entrepreneur first, where we invest in individuals to help them find a great co-founder and develop their ideas into successful start-up. I'm joined by Dr. Gena Gorlin, a clinical psychologist, founder coach, and faculty member at the University of Texas at Austin. She's been collaborating with us to better understand and support the psychological needs of early stage founders. Hi Gena.

Gena Gorlin  00:48

Hi Alice. In this episode, we spoke with Brett Kopf, a serial entrepreneur at the intersection of FinTech and education. In 2011, Brett founded Remind, a tool designed to improve communication between teachers and parents. Remind has since grown to over 30 million active users and is used by 80% of teachers in the United States. [His] company Omella is an all-in-one platform for payments, forms, and signatures, that Brett founded after seeing thousands of educators struggling with collecting money. In this conversation, we talked about Brett's journey into therapy and how it helped him as a founder, the differences in approach between his first company and his second, how prioritizing his responsibilities as a father actually makes him a better founder, and much more besides. So without further ado, here's our conversation with Brett.

Gena Gorlin  01:37

Thank you so much, Brett, for joining us. I'd love to start by just hearing in your own words, a little bit of your founder story in a nutshell, what have you built over the years? What are you working on building now? Tell us about the narrative, and then we're gonna start pinning all the interesting psychological meat on it.

Brett Kopf  01:58

Pin away; from the son of a therapist, I'm so curious to hear what you're going to do. So I like to tell people that I started my first company in fifth grade, which is a lie. But that is where the "why" came from. I was diagnosed with a slew of learning disabilities when I was a kid. And I pretty much spend the next, call it 16 to 17 years in my life, feeling not smart in school. And that was mostly because the structure and the system that I grew up in - and I went to a wonderful public school - it just wasn't fit for me. I was just a bit different. And I would be taken out of exams and classes, and I would have extra time, and I would have a special teacher to help me on things, and then the undercurrent - the emotion of what that made me feel - was not smart. Now I feel smart, now I'm very confident with who I am and who I'm not as an adult, but for a very long time it was difficult to figure out. And so that sort of energy of feeling not smart propelled me to start my first company, which is called Remind.com.

Brett Kopf  02:52

So tactically, Remind is like Slack for education. I wanted it because I had this teacher that totally changed my life. She sent me - well, what she really did was like she cared about me a lot, but I noticed that she was struggling to communicate with our students. And so I tried to solve a problem for her. And Remind then became (?) very big. So, Remind has over 30 million active teachers, students and parents. It's used by more than 80% of every teacher in the United States actively, they send billions of messages, hundreds of employees, yada, yada. And I just kept my teeth, and I learned a lot about the world just being thrown into the deep end. And that was my first company. And I'm on the board of that company. And my second company, which I've been working very quietly for the last three years is called Omella. And the way I explain it to my mom, who's 70, i and the reason I say that she's 70 is because usually technology isn't her forte, but she's getting very good at emojis now. But the way I explain it to her is to imagine if Venmo, GoFundMe, Google Forms, and DocuSign had a baby, and that baby was super simple, all-in-one, and only for this weird niche category of schools and clubs and PTAs. Like these mission-driven organizations that I think are very underlooked, doing very important work in their local community, and have bad software. And we want to help them. And that company, is you know, first of all: 10 people, 100% remote, on the track to profitability, growing. And so those are the things that I've started, I've started a lot of other things that I failed at, I'm happy to talk about those, but those are in the depths. But I think just thematically, to close this out, as a human being my identity as an entrepreneur is to try to solve problems in very mission-driven categories that legitimately help people. And I say that just because a lot of entrepreneurs—and there's nothing wrong with it—but say they want to have impact, and they're very impact and mission-driven, but then they build something that is like the antithesis, the opposite of impact. We are legitimately focused on helping people that are doing important work in their local community. And I liked doing that in very big, underserved markets that most people are very scared to figure out how to get distribution into, and I like doing that. And I also believe in making money, and our company's making money, and we're growing, and we're reinvesting that into the product. And then about me personally, I live in Colorado, I have a young boy, I'm married, my wife's name is Courtney. And I think that's me in a nutshell.

Gena Gorlin  05:08

That was beautifully done, thank you, Brett. You've already done half the work for us in just laying out the narrative. So I've many, many questions. But what I'd love to hear a little bit about, and you've already gotten us started in this direction by giving us some of the psychological history of what powered you into building things that, in a certain sense, apply your smarts but also prove your smarts in a really hard-to-contest way. And I'm wondering if you could tell us a little bit about that part of the history: I know you've mentioned to me before that you saw a therapist who was really helpful to you at one point, perhaps earlier in your founding journey, and that it was at a time when there were also some personal stressors that were really challenging you as a founder. And I wonder if you can speak a little bit about how those motivations have evolved for you through the therapy you've done, through just the growth that I know you've really prioritized.

Brett Kopf  06:14

I'm going to ask a clarifying question to make sure I understand. When you say motivations, you mean the things that propelled me to build stuff in the world? Is that what you mean?

Gena Gorlin  06:23

Yeah, and particularly on this scale that you've described, where you're really doing it the hard way.

Brett Kopf  06:29

For the first part of my career, it came from a very not good place. Meaning like, emotionally, I wanted to prove so badly to the world that I wanted to build something that was highly impactful on a very large scale, that I would have this energy or this lifeforce inside me that would make me work my rear end off (I don't know who's watching this, I won't use [bad language]). I would work really, really hard, and I also wouldn't prioritize things that mattered. Now, what matters to me now is my emotional and physical health, my family, my nuclear family, and then my company, in that order. But when you would have asked me when I was 22, or 21, it wouldn't have been that, probably because I was young and naive. And I just sort of hadn't lived enough and been through experiences. And so because I didn't feel smart, there was this emotional propellant to want me to prove to the world—aka probably my father, who has since passed—but, like, prove to him that I could be something, and live up to his expectations. At the time, I had no idea that I was doing that, like, that I had that drive, though, because I wasn't aware of that. So to kind of connect the dots, I first started seeing a therapist—which I no longer do for now, just because I don't feel like I need it right now, I'm sure at some point in my life I will again—when I was living in San Francisco building my first company. His name was Garrick, he was amazing, and one of the things that I felt like he was really helpful with was being a very safe, transparent, reflective mirror to my conscious and unconscious mind. And one of the things that he always explained to me is like, it's really hard to figure out why you are - you being whoever's listening to this - why you are the way you are, and do things that you do by yourself. And so he acted as this sort of safe - I say safe not in the literal sense, but metaphorically - he was a really trusted, safe person who would not judge me, or also infuse his opinions on good, bad, or ugly. He practiced that type of therapy - you would know this way better Gena than I would - oh God, what's the most common one?

Gena Gorlin  08:21

Psychodynamic therapy?

Brett Kopf  08:22

Yeah. I was just so frustrated; I'd say, "Tell me the problem, analyze me," and he goes "Hmm, that's really funny, it's interesting that you want me to analyze you, I understand that you want that." And I'm like, ah! - tell me the answer!

Gena Gorlin  10:21

Gaaaah! So frustrating! [laugh]

Brett Kopf  10:21

But what ended up coming of that, it would help me identify why I was the way I was. So I can give examples of that. At the time my dad was dying... So let me just set context: my first company supported hundreds of millions of users, adding 200,000 to 350,000 users a day, 85% of which we would retain. Faster than Facebook, WhatsApp, at the time of growth. It was crazy, raised a ton of money, whatever, all of that stuff. So there was a huge amount of pressure, self-induced, but also just to perform in the world, especially because our customers needed it. And there was all these personal things that were happening in my life at the time, too. So, my dad had Parkinson's, and he was sort of on his downfall. I was living in San Francisco also trying to manage that. My brother too, he's my co-founder. The personal life stuff, and I can go into that if you'd like, I'm happy to, but there was all these things that I was trying to reconcile in my brain that he would help me put into what I ended up calling "spaghetti buckets", I don't know why, but like I would visualize a bucket of spaghetti. And for me, it was helpful to categorize the big problems in my life when I was with him. One problem was like trying to reconcile the death of my dad. No, he wasn't dead at the time, but he was on that path. The other problem was trying to decide if I was ready to get married to my now wife, which thank God I did, but that was really hard. But I didn't know, which he helped me figure out, that my dad dying and kind of coming to terms with that was sort of a mental block to me even getting to the point that I can be ready to take that next step with my wife. And then there were some other things, but he helped me structure those things and understand the realness of them. Like, you know, I know I'm babbling here, but when the company was growing so fast, it was hard to even take the time to consciously say like, "well, your dad's dying right now". That's bad, like that's a very sad, horrible thing that's happening. And so he gave me that space, that structured space and time to do that. And we would talk about those things and understand how it was making me feel. I don't even know if that answered the first question you asked, but those were the types of things that he helped me do.

Gena Gorlin  10:52

Yeah, I mean, it's all incredibly relevant and helpful, and I know our listeners so appreciate just your raw, honest recounting of those very painful and personal buckets at the time, I can only imagine.

Brett Kopf  10:57

Can I put color on that real quick? Let me give context to why. So here you are seeing me is like I started one company that has a bunch of users, I'm starting my second company, it's like on a good path, yada, yada. But no one knows the personal side, other than my wife, of course, or maybe like my best friends. So you know, when like my dad had Parkinson's, there got to be a point where he could hardly move, he could blink his eyes as a yes or no. It's like the worst torture that you can imagine for a human, and for a loved one to see. And to compartmentalize and decouple the things that were happening in career life versus personal life is brutal, especially for a 22 year old. Just the reason I'm sharing that is because as an entrepreneur - look we have a lot of customers who did really care about me as a human, but at the end of the day, it's not their responsibility to necessarily care that I have this very real personal thing happening. When they send a text message, and they relied on my service and Remind to do something, and it had to do that thing. That's just the reality of it. And so when I'm sharing that is because there's like the surface level as an entrepreneur, what you're doing building something for the customer, and you have employees - but then there's the personal undercurrent of all the things happening in your life good, bad, or ugly, which are inevitable - and everyone goes through something - it's very difficult to manage both of those. And they are both true. Meaning I had to somewhat handle my personal life, and you have to execute at a very high level for what was demanded of me for my company.

Alice Bentinck  12:25

It's interesting, 'cause I think your point here around, everyone deals with this, and maybe you deal with it at different times, you know, as and when life throws these things at you. But it's so rare that people's founding stories actually talk about these things. And when I think about the founders that we've worked with at EF... you can't choose when your personal life happens. And I think it's very, very hard, and the trade offs that you have to make in terms of "my startup is super important. It needs basically 100% of my attention 100% of my time, how do I then justify to myself, to my family, to my employees, having any shift or change in focus?" And I think it is really hard. Did you end up feeling any guilt in either direction, you know, guilt to the company or guilt to your family about how you were focusing during that time?

Brett Kopf  13:15

No, at the time, no. Retroactively, after it happened? Yes. And at the time, I didn't have enough time in the day to even have the time to feel guilt. The only time that I had time to think about any emotion was when I was with my therapist. And then after all these things happened - so I stepped out of a day to day operating role in my first company, I took a year off and I traveled with my wife for some of that time, and I kind of reevaluate what the heck just happened. And then what qualifies a happy fulfilled life for *me* - I say me because everyone's different. And what I decided was thematically, there is my physical, emotional health, the relationship I have with my very close family, specifically providing for my wife, and with my son, and my dog. And then you know, my mom, my brother, the close people, and then it's the company. But I reprioritized my life out of all of that. And I could not have done that at the time. I just wasn't mature enough. And I hadn't been through (inaudible).

Gena Gorlin  14:14

Can I even try to push further on this challenge that we've surfaced, that simultaneously you're somehow giving 100% to this company you're building, and you're also trying to give 100% to this life you're living, and it doesn't add up? I'm wondering, if you reflect back on how you approached your company and sort of what happened with the company's growth and trajectory at the time, if we think of the "before" time—before you had done that reflecting and reprioritizing, or as you were just still getting started on it—and then how you approached it afterward, and how you approach your current company. What differences would we see in your approach as a founder? Like, your decision-making, and just how you think about priorities within the company, about relationships with your team? What's different now that you have this different vantage point on your life as a whole?

Brett Kopf  15:21

Well, I now prioritize everything that I mentioned. It's like health, family, then company; everything is revolving around that. And I don't care what external figure wants me to be another way, I just don't care. External figure could be a VC or like the press, I just don't care. Like, because I care more about providing or being with my son, than I would be on the cover of Forbes. I cared about being on the cover of Forbes when I was 21, I don't give a shit now, excuse the french. Unless it helps us acquire a bunch more customers, because that's what we're focused on now.

Gena Gorlin  15:53

Has that made you a worse or better founder, just taking that as the standard?

Brett Kopf  15:59

It depends on who's asking or what their metric is.

Gena Gorlin  16:29

Sure; well, what's yours?

Brett Kopf  16:05

Me personally, I think I'm a bit better because I have a more balanced life, and I'm very clear in the intention of what I want in the long term. Let me be clear on that: I want to build Omella, I want it to be very large and very impactful, someday as big as Remind is. I do want that. And I get up every morning at 4:30 in the morning to grind a few hours in the morning before my kid wakes up so I can help him get ready. And then I go back to work. And so I still work very hard. But I'm not willing to sacrifice. So what that means is, probably at like four or five o'clock I stop working and I spend the next four or five hours with him. It also means that I spend one hour during the day exercising. Now, I'm saying this super confidently now, but I'm really not perfect at it, like I struggle with it quite a bit. Because I have my career identity where I want to build something really impactful, and I have to work a lot. And I am just that way natively - it is who I am. And I think the company needs it. And also I want to spend time with my son and my wife, and I want to exercise and do the things I want. And so you'll have to ask me in five years if both can be true. Or if I can build something that has $100 million in revenue and impacts hundreds of millions of people, and have a great personal life; I don't actually know. And unfortunately, one thing that scares me a bit is that I don't know too many public figures - and maybe this is just because the ones that aren't public are busy with their personal life or working - that have figured out both, where financially the things that they have built in the world are very impactful, and they have a very intentional, good personal life. Usually it's like crazy workaholics that are really not good personal life. And I don't want that. Does that make sense?

Gena Gorlin  17:43

It does make sense, and it's interesting to hear you say that because I think part of my charter for this podcast is to gather the counter examples. And I think we've at least gathered a couple of, dare I say, you know, minor, but real counter examples. And I suspect with time that you will also prove to be one of them. I'm optimistic on your behalf. But I have a radical hypothesis. And I'm just going to disclose this now, so that it can be part of our shared context to this conversation. My hypothesis is that it's either net positive-sum or zero-sum, and that when we think about these parts of our lives in a zero-sum kind of way - that you know, we're necessarily trading off one against the other, and that there's a pie and these are parts of our pie, and it's a question of just how much of our pie we want to devote to our job and company versus our personal life - that that's a kind of losing narrative. Whereas I think there's another narrative, and I've seen it bear out, you know, we interviewed I think, two sets of founders you're familiar with Brett, Keith Schacht and Ray and Rebecca Girn, who spoke of the ways that they integrate these parts of their lives together. And I've heard it in a few other places: you know, Ben Horowitz speaks of the kinds of challenges we're talking about now in "The Hard Thing About Hard Things" and how he’s kind of navigated some of those hard decisions. And I think that there's an approach, this might also come back to our motivation theme, and maybe we'll talk about that a bit more - how your motivations evolved - but I think there's an approach to life as a whole, that makes you fundamentally a better founder - if we really think about your goal, your mission, your vision for what you're building - and fundamentally a better dad, and a better partner, and a better human. And I sort of feel like you can't do one without the other fully, which is almost the opposite of the way we think about it intuitively, right? It's sort of like, "well which one are you going to prioritize? And you'll do less of one if you do more of the other", but I actually think that there's something backwards about that. I think it's sort of like, you're doing it all in a certain kind of intentional and authentic way, or you're compromising it all, at some level. So I just want to explore that - I might be wrong. But that's part of what I want your help figuring out.

Brett Kopf  20:15

Well, I hope you're right. And we have to check in in three to five years if it's a true statement [for me] specifically. Thus far, I am doing a pretty good job at it for our tiny company. And we have to make tradeoffs, though; so let me give you an example. Remind has raised a lot of money. My current company Omella has not, now we're much smaller, but even at the same time, we have not. We are running the company in a very methodical, thoughtful way, that we're focused on getting to break-even profitability. Now the current macro-environment has changed a ton since 10 years ago, everyone should be saying that on this podcast now. But in general, if we remove timeframe aside, we want to build a company that is long-term, sustainable, profitable, has healthy margins, has very good retention, where our customers love us, and there's a high NPS [Net Promotor Score]. Those are the things we're focused on. Sometimes that means though, like, I'm not just throwing money at a problem, sometimes you have to go slower, which drives me crazy. And it's probably the right thing. And in five to ten years from now, we'll still be around, and hopefully, it'll be a really big, impactful company. Where before, and arguably just because Remind was such a unique case, for—most companies on the planet don't add 200,000-300,000 users a day, where it will be like "Oh, my God, just holding on for dear life, throw money at every problem because we're growing so quickly." I don't know, maybe it's just because that was a unique case. But if we have to make trade-offs, that's the point, like we're making trade-offs now, or sometimes we have to go slower. Another personal example is, what I would have never done before, is every Friday at 12 o'clock, I go play basketball. There's a game that I play at my local gym for two hours, which is my version of meditation. Two hours out of the middle of the business day, but it makes me... and still, the lizard brain—which I know you know, Gena, that word—the lizard brain in my head, like the bad Brett, says "Oh, what are you doing? That's bad." But I know that it makes me a better person for my family, but also for the company. And it's like physically and mentally the right thing for me to do. So that is a worthwhile trade-off.

Alice Bentinck  22:12

One of the things that I think many founders, particularly first time around forget is that ultimately, for a large part of the company's life trajectory, if the founder leaves, if the founder can't maintain their energy, their mental health, their ability to keep going, often the company will collapse. And that's particularly true of the CEO, the CEO-founder. I mean, when I look at some of our founders who are struggling, it's often because they are always prioritizing the company. And don't recognize, as you have, that actually the most important thing is that you are able to be on your A-game. And if that takes spending four hours every night with your child, doing your two hours of basketball as meditation, I think understanding that about yourself feels like such an important thing, but often something that only a second time founder realizes, because they don't feel the... I suppose the guilt that comes attached with that. They understand that it's fundamentally an important part of making the company successful. Do you think your first time founder-self could have got to that same realization?

Brett Kopf  23:15

No way. I wish, and I don't want to also make that seem like others can't, I hope they can, and I hope they are genuinely better than me, but no. Part of the reason, is because I still struggle with it, a lot. And I'm like... 35, and I've started a new company, yada-yada. I said "no way" very aggressively; I'm skeptical of it. I was so laser-focused... Here's the problem with it: I think that, given the skills that I had at that point (and I have more skills now because I'm more experienced), I don't think I had the emotional or physical capacity in the day to do other stuff.

Gena Gorlin  24:02

Where does that emotional capacity come from now? Like, what's been added to your tank such that now you can make it work?

Brett Kopf  24:10

I think there's probably a mixture of time and experience. And like, I've just seen a lot of things and, you have a lot of shots on goal. And then my son - like when I had my son - he's almost two years old - for me it put a new perspective on what matters and why. I'll tell you a very personal story that I've gotten permission from my wife to tell this story because I'm embarrassed by it, but it's a true statement. My wife - well she wasn't my wife then, she was just my girlfriend; we've been together for 11 years and her name is Courtney, and she's the best. We were just dating at the time - and I explicitly told her, I was like, "you're not my priority right now, it is the company." And to her credit, she said, "I understand and I know that you're ambitious, you want to have this impact, that's okay." And I wasn't always showing up for her how I should be. What ended up happening is Remind came and went. I mean, I'm still on the board and everything, but like it's being ran by an executive team, and it's on like a good path, yada, yada. But Courtney is forever. And I didn't realize that at the time. And only after, you know, I took the time off, I'm like, "Oh, my God, were my priorities so backwards." And it's embarrassing to even say that out loud, but it's also the truth. And so now I know, that's what my priority is now, it's like my health first - and I have a very strong opinion on that because if I don't have that, then I can't show up for her, or the company. And just side tangent, clinically I have dyslexia and ADD, one of the things that I prioritize heavily is health. So like, I work out five to six days a week. And I try to eat really well. The thing that I'm not necessarily as good at is managing my emotional state. And so just to your point, part of the reason I say "no way" back then is because I still struggle with it. I was talking about it with my wife this week, it's like ah man, it's either I'm working, and I wonder what my son's doing right now, or I want to be with him, or I need to exercise. Or when I'm exercising - unless I'm playing basketball, because then my mind turns off, which is great - but if I'm lifting weights, it's like, "oh gosh, I have to answer this support ticket." So it's still hard; I'm still conflicted on both, because at the end of the day, I want to build something that's very big and impactful. Just for me personally, I'm not okay just building something that is sort of average, because I see this vision and I want to help these customers, I really do, I really want to have that impact and help them.

Gena Gorlin  26:28

Yeah, and I'm really happy to hear you say that it's still a work in progress, because that is so in the nature of building ourselves and learning about our own emotional needs, and about our motivations, and about all the complex ways that we manage our attention day to day. And I think it's a really false picture of the process, you know, anybody who says "well, here's everything I've figured out, and so now I can be, you know, the perfect superhero founder", because they're just either setting themselves up for a fall or they're BSing. Like, of course it's a work in progress.

Gena Gorlin  27:09

So part of what I'd love to maybe now circle back to with this added context that you've shared with us is, how is your motivation different now? Because I feel like that might be a through-theme, and a lot of what we're talking about, a lot of the ways that you have grown and that you're still growing. You know, when you mention now, you want to build something impactful, something that's great, not just something middling and ultimately meaningless. What does that mean to you now? And how is it different from those early days when, by your own lights, you were motivated by the wrong thing?

Brett Kopf  27:44

There's two big differences. One from just a pure business standpoint is I want to have a business with strong, what you call basic business fundamentals and clear unit economics, which always come back to, do your customers come back? Do you have healthy retention? Do you have a high margin? Do you have high engagement? Are you growing in a healthy manner? Meaning are you making more money than you're spending, and having a good business model so you could be running the company forever? Like, that part's really important to me. Part of the reason is because with Remind we didn't charge for a long time, I think for that company it was right, just because we were growing so quickly. But I just want to build a company, and before it was maybe more of just a product. And I'm a very product-focused founder. And so right now, I care about the product a lot, but that's an input to having clear business fundamentals and clear unit economics. Does that make sense?

Alice Bentinck  28:39

It feels like a very end of 2022 statement. In that I think a lot of founders are now being encouraged to actually think about unit economics. But it sounds like this is something that you've been noodling on for a long time. Why is that so important to you? How did that come to be so important to you? Because it's not what the startup culture has been for the last however many years.

Brett Kopf  29:00

Yeah, you're giving me a layup here, it's horrible sport/basketball pun, but the reason is because I was the antithesis of it for 10 years. We walked the line; like, we did the opposite with Remind, where it's like, grow, grow, grow at all costs. Now again, unique situation, adding 300,000 users a day. And so we can raise all the money we want. It's just a crazy number. But I saw like the negative implications to not having clear fundamentals nailed down before you scale. And if you don't have those things, a lot of not good things happen. And eventually, the music stops. Now, the music's stopping very hard right now, everyone knows that. But we have been thinking - my brother and I, he is my co-founder - for years, and years about building Omella. And we've been building it for three years very quietly, but even years before that, we were thinking about some version of payments in the education space. And then there's the value systems of how we build it. And so I almost think, you know, right now it's kind of a scary time, there's layoffs happening right and left, and valuations are getting slashed by 80%, but I think some of its good because it gets back to truth and clear fundamentals. And it's like, put up or shut up, if you're not going to build something that's valuable that a customer wants, probably the company's gonna die. And it won't be the end of the world, and you're gonna learn from it, and maybe you'll build something else, or maybe join someone else. But I'm definitely on that train now, and I think about it every day, like that's the thing that keeps me up at night. For us, at Omella, our economics are clear. We make money on every transaction, but now it's like, how do we get to break-even profitability as fast as thoughtfully possible. I use the word "thoughtfully" because... we raised some money - I can throw a bunch of cash at a problem right now. But I don't know if that would actually get us there faster. One of the things I learned is, you know, when you're in a very high growth environment, you think "oh, we gotta hire, we gotta hire, we gotta hire." But hiring more people usually doesn't equate to higher engagement, retention, revenue, or growth. Oftentimes, it doesn't. And you're seeing that as a reflection now, it's a latent reflection of what's happening in the market, where, you know, the best companies in the world - Stripe is an example, we love them, but they're even firing, they fired, like 9-10% of their staff. That's a long answer.

Gena Gorlin  29:00

That's a great answer. Yeah, I just, I can't help as I hear you talk about your current approach with Omella, and your previous approach with Remind, it's like two different people. I mean it's all you, right, but it's like two versions of you we're hearing about, where there are certain deep insights, and corresponding desires, that are driving you now, and that are driving even the trade offs that you've spoken off. Where it's perhaps trading off short-term for longer-term gain. But where, as a young twenty-something whose father was dying, who was really just starting to kind of grow up (?) at adult life, you were on some kind of a current, of both startup culture, but also that need which was still somewhat invisible to you, of proving that you're smart and that you're capable, and the urgency of proving it while you still can, perhaps even while your father was still able to see it. And it feels like there's a visionary-ness to the way you run your company now. I guess I wonder, if you were starting Remind, if you were founding it today, with everything you know and all the perspective you've gained, what would be different? Or is that a just incoherent question, because maybe that's not what you would do.

Brett Kopf  32:38

I probably wouldn't do that, it's only a little incoherent because the timing in the market is very different—like, back in 2010, messaging was just becoming a thing, but I know that's not your point. But I do think I would do things different. I would just go back to value systems. So okay. Visionary or not, the only thing I'm visionary with is talking to customers and deeply caring about them and wanting to help them, this niche that is very big that no one knows about. I love that. I love that more than anything is really helping them. But then there's a set of value systems that apply that I believe are right, that different from the old version of me, version one. Which maybe if you went to business school - which I didn't, I studied agriculture and I nearly dropped out of school - they would teach me, but it's like clear fundamentals on what is a good healthy business, and wanting to do it for the right [reasons]. So let me give you an example. For this new company, Omella, we raised like, I don't know, four or five million bucks. Every single investor that came in, I said this will not be an overnight success, you have to be with us for like 10 years. You should not expect liquidity for 10 years. And if you want liquidity faster, please don't invest in the company. By the way, we don't need your money. And setting those expectations upfront was really important. Because we only wanted people who weren't going to be knocking on my door every day. A lot of this confidence, by the way, comes from just doing it a few times and knowing what I believe to be right and true in the world. And knowing that if I'm wrong, I'm gonna admit it, and I took a shot at gold and I tried.

Alice Bentinck  34:07

I love the assertiveness, and because it's sort of this—your confidence that you have built over the last decade or so of being a founder, then culminating in an assertiveness which is actually just a really strong business strategy. And it's just, this is what you believe will allow you in the company to be most successful. And being able to put that to investors as a kind of, you know, get on the bus or don't bother even buying a ticket for the bus—it's very, very compelling. I mean, how did investors respond to that? Because I would assume it'd be like catnip for many of them.

Brett Kopf  34:44

Yeah, it was good catnip, even though I don't like cats, I like dogs. But it was good for them. So let me give a caveat. First of all, I've done this before. And so we just have one easy step where we've proven something, and I have a network, yada yada, and I've been in the Valley for 10 years. So that part was just natively easier. But then the other part... like when I tell younger founders who're raising money, it's like it should - I think, used the term a car, but you should be on this freight train. And you're driving the train, and you see this investor in front of you - and I don't mean this in a crass way - but that investor is a barrier to you. And then they can give you money. And that money will lay longer tracks for you, but eventually those tracks will run out. And maybe it's okay that they lay longer tracks, but you should feel like you're going to run that person over if they don't get out of your way, in a thoughtful, humble sense. Now, I speak confidently, but I'm also quite... I had and have a lot of humility. I'll give you an example. When we raise money, it's this is the vision of the company, this is why we're doing it. This is why we were uniquely gifted to focus on this. Meaning we're not going to build a rocket ship like Elon Musk, we're not good at that. We'd be horrible at that. But you know this education space and building utility software... we have hypotheses on how we're going to make money. Here's what the three of those are, we don't know for sure yet, but we've spoken to 500 customers, and we understand their problem. And so we admit what we don't know, and it's just truth. It's like, if you were talking to your mom, or your dad, or like your best friend, and them investing and putting their own personal cash, you will want to be really honest with them. And so if we're investing the most important asset we have - which is not money, it's time - we wanted to make sure, my brother and I, before we ever raised money, and every round that we raise with Omella, it's like do we feel honest and good about this? Is this like a true statement? Because we don't want to bullshit someone if we're not actually ready. And so I am very confident, yes, but [I also] have a lot of humility in what we don't know. And every month in my investor updates it's like, man, here's what we screwed up on. Here's what we're doing very good. Here's the single thing that our company needs to unlock, like this. And one more thing because I think it's important for people listening, the way I speak to investors, or even on here, is like we have systematically eliminated threats to what we think is building a good company, which is first retention. If I pour water in this bottle does it leak? If it leaks, then nothing else matters. Like you shouldn't focus on acquiring customers if the bottle is leaking. Then once the bottle has very good retention you want to make sure you have really good engagement, do they keep coming back? Then do they activate? Well, so when they say "yes, I want to use your product", do you get them onboarded really quickly? And *then* can you acquire a bunch of customers? And so when I speak to them, that's exactly what I tell them, because that is a true statement. Like if I was talking to our executive team internally, it's the same way that I speak to investors.

Gena Gorlin  37:27

Yeah, it's so interesting to connect the dots between the way that you're now approaching business. It's this really systematic, principled, kind of long range approach, where you'd see an investor not just as a source of some immediate extra runway, right? "But okay, well, we just need our track to last for as long as possible so that we can keep moving", right? But you see this really kind of long term, complex strategic vision for which you're laying foundations. And so you're able to make choices that might feel like huge trade-offs or losses to someone who doesn't have this perspective. And you're also able to take time for your meditative basketball games, and you're also able to love your son, love your wife, and make that a really non-negotiable part of this expansive life. And to me, those feel deeply connected, right? When we contrast the kind of psychological space that we're in, at a point where our family unit is still in flux. And we're losing someone who's dear to us. And it all feels fragile. And it all feels kind of urgent, and it's in a certain way and out of our hands, right? And every decision feels like "Okay, this is going to be the make or break of whether I stand on solid ground in my life or not" versus "yeah, this might not work out, and I'm gonna be fine, and I will have learned the lessons and I will try again. But you know, but here are the principles I'm gonna apply." Just, that feels so fundamentally different to me.

Brett Kopf  39:22

Yeah, I think it is different. But don't get me wrong, like I speak here confidently to you. And I did reference my humility - I have a lot of it. [T]he biggest thing I struggle with is anxiety, I'm a very anxious person, which is good and bad. The reason it's good is because I will not not respond to a support ticket in five minutes. Because I know that it's just natively the way I am, and I just want to help our customers. Is it necessarily a great thing that I wake up in the morning at 4am or 5am, and like, want to respond to a customer? Maybe not; so like, I'm not perfect at this and I'm trying to figure out the balance too. But those core fundamentals of like wanting to be healthy and be there for my kid and my wife and and build something in the long term, those are true statements. Like I believe in those a lot, and we're executing on them every day. But it's hard because while I have that long term - I'm feverish, I am feverish right now working. Sometimes my wife, because she works from home too, slash is with my son a lot. She goes, like, "I think you need to like, just go upstairs and go away, because you have like, really bad energy right now." I'm like, "Okay, you're probably right", and I just need [to] take a chill pill. So I have a long term vision, but like feverish in the day-to-day to try to get a lot of stuff done. Because it's... speed matters in starting companies, as you know, it's like one of our most precious assets, is moving quickly.

Gena Gorlin  40:34

Yeah, so it's not like the feverishness goes away. And, again, it's not like, the light switch has gone on, and now you have this grand perspective, and you don't have to manage your own day-to-day psychology anymore. And that is not the picture we want to paint for anyone, because we'd be setting them up for disappointment, right? It's more so that you both have the internal and the external resources, say, in the form of your wife being able to notice that, and to ground you in that way, that now have allowed you to, in crucial moments, to kind of skew the balance toward that perspective, right, and toward the wisdom that you've gained. Even though you're jittery, even though you're waking up at 4am, but still ultimately to stay on your chosen path, or perhaps to return to it. You know, when you do.

Brett Kopf  41:31

Yeah, and honestly, you know, if someone's listening to this are like, "oh, this is really cool and existential, and like it feels good, but like what do I do with it?", you should just work out. And I know that sounds so simple, but I think working out physically is so important. And there's all the research that backs that, I'm not going to like talk into that, but physically—yeah, there's legitimate science—but just physically exercise and move your body and work really hard. I have a lot of energy. I'm very effusive, as you can tell. And if I don't exercise every day, I'm not only doing a disservice to my first and second goal, which is my health in my family, but I'm doing a disservice to the company. So, like, it's probably one of the most important things you can do is exercise.

Gena Gorlin  42:13

Yeah, it's wild. And I mean it in a certain way, it contains all the elements in microcosm, that constitute this mindset that I think we've been circling around, you know, whatever it is that I'm calling the founders mindset on this podcast, that there's the experience of achieving a chosen goal, and of the effort that that entails. Like they're packed so tightly together, it's like, you can't miss it, right? You can't miss - okay, either I've made it to that line, or I haven't. Either I've done my 20 reps, or I haven't, whatever the case may be. And there's no lying about it, there's no BSing it, right? You either you've done it, or you haven't, and it's between you and your inner demons to negotiate that endurance, right? And whatever your reasons for wanting to get to the end, it's just you.

Brett Kopf  43:10

The inner demon statement is so good. One of my friends, he's one of my closest friends, and kind of like life advisors, one of the things he told me is like humans are natively selfish, as am I. As each of you are most likely to with certain things in your life, and there's certain things we're not, but like, no one in the world thinks about my life as much as I do. Or Gena's life as much as she does, maybe Matt does about you, your husband. But my wife doesn't think about my life as much as I do, nor should she. It's not her job, and she shouldn't have to do that. And so part of the reason I'm sharing that is because... I'm trying to build something that impacts hundreds of millions of people. And the emotional and physical state that I'm in, hopefully will one day affect a lot of those people. And so knowing that even though I think about myself a lot of times, it's not really about me, it's about helping those people. And structuring my life around exercising, and focusing on my family, and building this company for the long term, will hopefully help me achieve that and help those millions of people.

Alice Bentinck  44:14

But one of the things that you keep on using as a phrase, which is not a phrase you hear very often, but I think it actually really sums up nicely your perspective on life is this "natively". So you keep on kind of referencing back to the knowledge that you have of yourself, the knowledge of how you behave, how you work, your preferences, your flaws, and you use that as a source of power. And I think most people, I think many of us are brought up to believe when we have something that is natively seen as a flaw, or like as you know, inherently seen as a bad thing, we try and change it. Whereas what you're saying is, "hey, this is how I work. I'm gonna go with those parts of my personality, go with those parts of my behavior. And I'm going to acknowledge that that is something that I'm going to work with and work around", whether it's the fact that we're all selfish, or the fact that you need to do basketball - I feel like we mentioned the basketball a lot. That's a very, very powerful thing that it's very easy for founders to beat themselves up to try and change and become somebody who they aren't, rather than just saying, well, actually, this is who I am. Let's work it, how can I leverage who I am, to actually make this whole thing - life, work, relationships, family, work as a system?

Brett Kopf  45:26

Yep. So that actually—what you pointed out, thank you for doing that - is the archetype, or like the most important part of all of this. Well, the thing I didn't mention is in the middle of like seeing a therapist and starting our first company was I had a CEO coach at the time, and I took this thing called "Tilt-365", It's kind of equivalent to a Gallup poll, I think it's better. But it basically helps you figure out who you are. Every human being on the planet, they structure into one of like 16 categories. And when I read it, I was like, "oh my God, I'm reading a story about who I am as a person, good, bad and ugly." And how that applies to starting a company or showing up as a husband, or as a father is like, "oh wait, I understand why I'm acting like this, or I understand why I'm afraid to have those hard conversations, because I don't like conflict", which I don't, it's just natively who I am. And so it means I have to work harder, to make sure I have those. The faster you can know who you are and what you're gifted at, then you could outsource what you're bad at. And I can give you a ton of examples on that. But I tried to just stay in my lane, like I'm really good at sales and customers and storytelling, but anything that has to do with operations and finance or repetitive stuff, I'm bad at, and the company needs it. And so I love to find people who are really good at what I'm bad at, where I have a line set of value systems and principles, natively, and get out of their way. [B]ecause if you actually, you know, hopefully achieve some success where the company starts ripping and growing really quickly, you will not be able to do all those things, and you have to outsource what you're not good at to people who are really good at them. And be so okay with that. I delight in the fact that I have people who are better than me at my company right now, doing things that they're really good at.

Gena Gorlin  47:01

It strikes me that in order to be able to make those calls, you've got to not just know about yourself, but to return to our theme of, what is selfish or not, to really care about yourself and your experience as a founder, and to stay connected to your why's in order to make those long term calls, in order to have the hard conversations, in order to do the outsourcing, to lean into your strengths. All of that requires a certain orientation of... yeah, this is my chosen road, right? And I'm choosing to do it in a certain way. And *I'm* choosing to do it in a certain way. And it's gotta be me, because as soon as it stops being me, it's not going to work. [T]he foundation will not hold, insofar as I'm the foundation after all. And so there's a certain way in which when you mentioned that trade-off, [of] "well, I'm confident, but I'm also humble", you get to be confident because of the ways that you're honest and humble, and vice versa, I think. Because you've smashed that dichotomy in a certain way. It's like, it has to be about me, in order to really benefit these, hopefully, hundreds of thousands, or millions of customers, for whom I'm ultimately building this. And it has to be about them, but about them in a way that I actually genuinely care about, and I'm not just trying to, you know, prove that I care, right? Or prove that I'm good enough. It has to actually be about them to be about me, and it has to be about me to be about them. It's win-win. Or it's lose-lose.

Brett Kopf  48:45

I don't think I could say it any better.

Gena Gorlin  48:46

Speaking of concluding statements, having reflected on all of this, anything, you either wish you'd known when you were just getting started as a founder, or anything you'd like to impart on any early stage or aspiring founders who are listening?

Brett Kopf  49:04

Yeah, of course. There's like the tactical things of how to build a startup, and then there's the emotional side. I'll break it apart by two because you guys hit both in this podcast. [W]hen you build a startup it's really simple, you talk to customers a lot, you solve a simple problem for them, and you build a product that solves their problem, and you iterate rigorously. I spoke to 500 customers before we wrote a line of code. And so like that general framework is how I build all my companies. There's a lot that falls underneath that, but that's it. Just like talk to customers. Listen with two ears and one mouth, build a simple product, and solve a problem. That's like the framework in which I start the company. The personal stuff, that's super hard. I don't know if I have any - other than like, know thyself. I remember my dad, when he was actually passing, which I could not literally hear him. Well, literally I could but metaphorically, I couldn't. Where he said, "you know, Brett" - and this was like three or four years before he died - he's like, "all work and no play makes Johnny a dull boy." He didn't make that word up, it was in a book or it's a famous quote. And all I hear was like, "yeah yeah Dad, whatever, like, I gotta grind, I gotta grind, I gotta grind." And it's like, oh wow, I'm 36 now or I'm 35, and it's like, oh, you know, you kind of see 50, and kind of see 75 and 100, and it goes really fast. And once you have kids - for anyone who has kids listening, you know how fast it goes. And he had an interesting point there. Now, at the time I couldn't do anything with that, because I was so focused on [being] ambitious and growing. And I'm still super ambitious, but also life goes really quickly. So it kind of goes back to this point that you made about knowing yourself or that we've been talking about, knowing what you want and why, and making sure you're doing it for yourself and not someone else. I was doing my first company for someone else, little did I know it. But this company is not for someone else other than our customers of course, but the internal drive, there's a clear foundation for that.

Alice Bentinck  50:50

Thank you for joining us on this episode of the Founder's Mindset. Make sure to subscribe, or follow us to be the first to get every new episode. And if you enjoy the show, why not leave us a rating and review to help us to reach even more people. We'd hugely appreciate it. As always, you can find out more about Entrepreneur First by heading to joinef.com. And you get more of Gena's thoughts on founder psychology at builders.genagorlin.com. I've been Alice Bentinck.

Gena Gorlin  51:15

And I'm Gena Gorlin. See you next time.

David Booth is the quintessential “builder of builders” (BoB): as founder and CEO of On Deck, he is on a mission to “help more people start better startups”. And he’s doing pretty well so far, with 1,000+ companies founded and launched via On Deck programs and going on to raise upwards of $2 billion.

In this episode of the Founder’s Mindset, David joined me and Entrepreneur First (EF) cofounder Alice Bentinck—one of my other favorite BoBs!— for a wonderfully free-ranging conversation about the makings of successful builders, as informed both by his own personal experience and by the patterns he’s observed among the thousands of founders he’s brought together at On Deck:

Here are my biggest takeaways, with relevant snippets from the episode under each (paid subscribers can access the full transcript below).

1. You need the spark of agency

In reflecting on the start of his own personal founding journey, David recalled encountering “lots of little opportunities to… follow conventional wisdom within a system, or to break out and build something outside of that system.” He talked about how this choice shows up everywhere, if you look out for it—even in trivial decisions like “well, my friends and I are going to go to the same music festival as everyone else, or I'm going to organize a house for my friends, and we're going to go have a party there…” One such choice, which he now recognizes as pivotal, came in his first year of university studies:

“Going into university, I actually had like a little bit of a negative experience… and didn't really hit it off with people. And I remember a moment where I actually thought—maybe this is projecting in hindsight, but I distinctly remember saying—‘should I invest in fitting in here, and like joining and climbing the social hierarchy? Or should I go do something else?’ And I did the latter.”

So he went off and started a small clothing company and an events company during his studies, which resulted in making “a bigger, broader group of friends” and eventually “making friends with some of the folks in the hall anyway.”

Looking back on that and many subsequent decisions, David noted a common theme of asking himself, “what is the expected path? Graduate, be a lawyer, be a doctor? Or what is the opportunity to exit that expected path and do something different? And that's how I constantly prompt myself now, and those around me.”

David and Alice both spoke of this spark of agential initiative—this willingness to deviate from the well-charted or conventional path in pursuit of something more ambitious—as a prerequisite to benefiting from the kinds of resources that On Deck and EF provide. But they also spoke about how a lot more people probably have that latent capacity within them than would have been apparent prior to the advent of such communities and resources. Quoting David, “I don't have [the] magic bullet as to how to foster that spirit and drive, more than just to help to get the people who have the smallest spark of it together and help them realize that together.” Alice agreed that “ultimately, it is about bringing people together who can role model for each other what good looks like. I think that can support people who already have this as an intrinsic, but it might be a latent intrinsic. And so the group or the community is the catalyst for that.”

2. Culture is the kindling and fuel

It is no accident that so much of the technological innovation of the last half-century has been concentrated in Silicon Valley. This is not because people living in the Bay Area are somehow innately more agential; it’s because entrepreneurial culture is a massive multiplier of human agency.

How exactly does this multiplicative effect occur?

David shared one personal story from his teenage years that illustrated this effect very concretely:

“There was one moment that I do remember distinctly from, I think I was around 12 or 13. As a young go-getter I started importing iPods into New Zealand, where I was living at the time, buying on Amazon and reshipping to our local eBay equivalent. And it worked for a while, I imported batches of 5 and then 10. And then I got more ambitious and teamed up with a friend of mine, to raise a little bit of money from both of our parents, and buy a really big shipment of iPods on Alibaba. We promptly went to Western Union and sent a lot of cash to somewhere in China, we believe, [which] obviously never turned up again. 

And it was actually what happened next, which was one of the formative moments of my mindset, I believe: upon losing both the business I'd built and the capital I'd invested to go for it, [I] had a conversation with my parents, who took the opportunity to sort of convert it into a teachable moment and say, "this is how businesses can work. And there's this concept of limited liability; what you should really try to do is get back out there and build another one and try to make it back.

And I contrast that to my friend's story, [whose] parents said, "no, you can't lose money like that, you have to go and get a job and earn every dollar and pay us back."

Thus David’s parents had exposed him to a radically different narrative about the meaning of his failed venture—and, by implication, the range of future ventures that might be possible and worthwhile for him—than did his friend’s parents. Listening to this story, I couldn’t help but form a mental image of David’s entrepreneurial spirit burning brighter and hotter, while his friend’s slowly flickered and dimmed.

That said: what if we didn’t have the benefit of entrepreneurially minded parents? Or even if we did, what if we then find ourselves in a cultural environment where exemplars of ambitious entrepreneurship are few and far between? Quoting David again:

“The first chapter of my career was in New Zealand, [and] it's very isolated. And in particular, most of the ambitious people here figure out quite early on that they need to leave to go and capture the opportunity of their lifetime. They've moved to London, Singapore, New York, San Francisco. And so our, you know, the New Zealand diasphora is, around 25% of our population lives overseas. And often that is the most ambitious, you know, successful ones. Which is a problem when you think about people who are going through college and looking for mentors and role models locally and haven't yet had the opportunity to step outside of that fishbowl.

So this is a big part of the answer, and one that David has baked into the community-centered model of On Deck: go where you can be surrounded by inspiring mentors and role models. Speaking about this further, David reflected:

There's a writer I want to shout out, a friend of mine, Henrik Karlsson, in a blog called "first we shape our social graph, then it shapes us"... It just takes the idea of "you are the average of the five people you spend the most time with," and makes it more intentional…. How do you go out and seek out people who you want to draw from culturally? And this has always been something that has inspired me around On Deck; I've said, you know, the best way to get from A to B, is to go out and find a group of people who are all going from A to B, and get on that journey with them.”

What is it about having this community of fellow travelers that shapes your own success? The intuitive answer might be that you get more and better advice on how to do what you’re doing. And that is almost certainly part of it. But there is also a counter-narrative that being “high agency” should mean resisting advice. Shortly before recording this podcast conversation, I’d listened to Lex Friedman’s interview with Marc Andreessen, who, when asked what advice he’d give to aspiring founders, said something to the effect of “founders don’t ask for advice. If you’re asking for advice, you probably shouldn’t be a founder.”

When I quoted this back to Alice and David, they both offered some helpful perspective. I was especially compelled by Alice’s point that Andreessen’s statement best applies to founders already steeped in the Silicon Valley milieu:

“Mimesis is real; like, the idea that the people around you will influence your preferences, choices, desires. And this, I think, is particularly true around founding, and where, if you are based in Silicon Valley, and you're surrounded by the world's best founders, best VCs, knowledge, early startup employees, etc, you will probably learn, most of the time, the right things to do. I think there is a bigger challenge when your ecosystems are much more nascent… If you're in Silicon Valley, and you're like, oh, I don't know, should I become a founder? Should I not? Like, is there someone to hold my hand? You're probably not a founder. If you're in London, or Paris, or Singapore, or wherever it may be, going, ‘Oh, I don't know if I should be a founder or not,’ that's probably a viable question to ask. Because for the entirety of your life, you've had people telling you, ‘do not do that. Do not do that. Go become... an APM at Google, whatever it is, a legible career path. And so… I'm still very much in the same camp as David that the world is missing out on some of its most ambitious, high potential founders, purely because [of the] culture that they're in.”

David built on this further:

“Advice” is often this very explicit, "find the person who knows a thing and can tell you a thing." To me, [what founders need] is much more implicit; [it’s] surrounding yourself with others who have been on similar journeys, who are going on similar journeys. And it's the sort of feeling of being connected into that directional graph, which is actually what you need. And that's what, as Alice says, Silicon Valley has by default, [and] that's what most other ecosystems do not.”

The value of being connected to such a community, David went on, emerges out of every member’s active commitment to getting what they want from it:

“…[O]ur main job is to get the right people in the room, just create the conditions for you to support each other, and then get out of the way. You're not here to learn from us. You know, I'm no expert. We just think of operating within a community as: you need to be selfishly motivated; to the extent that you put value out there into the community, you contribute to it, you host a session, you teach people, because that's actually the best way for you to get the most value from it.”

Alice also eloquently described the “mirroring” function of mentors and community members:

“I would say advice nudges [the best cofounding teams]; it does not dictate their success. The most important advice we give actually is acting as a mirror. So particularly for a team that isn't particularly effective. One of the interesting things about co-founding teams is that, by the time someone gets married, they've usually had multiple romantic partners, and have formed some sort of mental model of what good looks like. Weirdly, with co-founders, most people find a co-founder and are like, "cool! Sign the co-founder agreement, we're all in." So largely, the role that EF is often playing from an advice perspective is saying, I've seen lots of teams, I've seen lots of co-founding teams. This one is not in my top quartile. These are the reasons why: you're not productive, you're talking over each other, you don't seem to have any respect for each other. And so it's more that sort of nearer and nudge of ‘let me give you the context I have, which is I know a lot about what co-founding teams look like, and let you use that information to make the decision for yourself.’ …And it's interesting, watching people who've been on the EF team who've given huge amounts of advice and mirrors and nudges, then found startups themselves: you can't be your own mirror.”

So in sum, what founders—and ambitious innovators generally—often need more than explicit advice is a certain kind of modeling, mirroring, and inspiration that only a community of inspiring exemplars can provide.

3. No substitute for your own judgment

By contrast to these various positive use cases of advice and community, we discussed what it looks like when, apropos of Andreessen’s comment, these resources come to serve more as crutch than catalyst. Here I shared an important difference I’ve observed in how very early-stage founders interact with whatever community or accelerator program is on offer:

There are these two very different approaches that they might be taking: where certain people, they leverage the network, and you see them kind of "turning on"; like, they hungrily take the advice and the resources, and they make it their own, and they do something with it that you didn't even expect. And they go and make these calls that are totally different from the calls that you've discussed having them make, but that actually make more sense than whatever you were originally suggesting. And you just see, okay, they've been activated, the fire has been fully lit within them. Like, maybe you saw the spark and you lit the fire, and now they're off to the races.

Versus, each step is like pulling teeth. Like, you're giving them another thing to do, and another thing to do, and they're coming to you for the next thing, right? That isn't going to work, at least if what you're trying to do is found a company.

We also talked about how this difference in approaches—let’s call them the “epistemically active” versus “epistemically passive” approach—manifests in people’s motivations for starting a company in the first place. For instance, David reflected on the phenomenon where people “seek external validation as a way of outsourcing their own judgment of readiness” to start a company. He continued:

One place this regularly shows up is in very talented people who [are] sort of seeking the next level of credentialism as they go, credibility or badge collecting, if you want to be cynical. I went to a great high school, and then I got into a great Ivy League university, and then I got a job at McKinsey. And then I got a job in investment banking. I went back and did an MBA, and then I went back and, you know, there's always a "next thing." And one thing that I don't have a very strong opinion on, but that I know that at some point, there's sort of... you climb ladders, and then you've learned enough where you need to get off that ladder and go build. Sometimes, in some industry, it actually makes sense to climb further; like, [if] you want to build a FinTech company and go into the depths of finance, maybe it does make sense to go and have a career in banking first. If you want to build something that's like a social app for Gen Z, maybe you should do that when you're 18 or 20. And try and fail a few times. So I don't think is a perfect answer. But there's definitely a connection between people who... don't trust their own judgment, don't put enough weight on their own judgment that "now is the time that I can take the leap and go build." So they'll look for an additional form of validation, additional credential, climb that ladder a bit higher. And for a lot of people, they get stuck there, they get trapped; the "golden handcuffs" are on, you're going to have some mortgage and everything else.”

Resonating with this, Alice recalled how becoming a founder meant having to unlearn her own prior tendency to outsource judgments of “success” to her managers and superiors:

I've always been very ambitious. And at McKinsey, it became clear that the way to succeed was to make your manager love you and get a really great performance review. And then you would get the top rating or whatever. And when I was leaving… I found it very hard that now I was going to be producing work that no one was going to look at. And it took me about a year—and Matt, my cofounder, used to literally just look at my work and be like, "well done, Alice, you've done a great job. This is great!", because I was so desperately missing that kind of external approval that I was doing the right stuff. You know, after about a year, I probably got over it. But, Gena, how much can you actually influence that internal intrinsic motivation?

My answer was that, of course, you can influence it a lot, since I don’t actually believe it is “intrinsic” but rather self-created. And the way you self-create it is by taking the epistemically active approach I mentioned above to whatever it is you’re doing, whether it’s working a job, or going to school, or running a company, or something else entirely. This brought us back full circle to the question of how someone processes advice, including the advice to “take the leap” and start a company:

Did you 1) take the leap because you judged it right? Maybe for terrible reasons; and maybe with a lot of input from a community, from a resource, from On Deck or from EF; but did you judge it based on reasons that now can go and be tested? Because now you're going to try, and you're going to check your hypothesis against the world? Like, you think that you can build it now, but maybe you can't, because there were unanticipated ways that the technology is more complicated, or you realize you need these skills first, so then maybe you go back to school, you course correct; but [whatever happens]: is your judgment ON?

[Likewise], do you take [your mentors’] advice and process it through [your] own very personal context, and say, "Yeah, you know what, I hear you, but like, I'm actually going to go ahead and try it anyway", or, "I hear you, but I'm actually going to stay in school for another two months, because I have a hunch that after I've taken this class, it'll open up this network"; and [you] might actually be wrong, but the fact that [you’re] doing that is a really good sign?

…OR, did you 2) [let the mentors or the accelerator programme do your thinking for you?] We've talked about this, Alice, [how some] people who go through your program, [they] are so excited that they've been accepted into this program; and now they have a stipend, and it's a sure thing for eight weeks where they just are going to be told how to be founders, and... they're going to be on a scoreboard, and they're gonna get their sticker at the end of it, and they'll win the investment committee hearing. And now they're just so completely departed from what it means to be a founder.”

3a. “Validation” versus its counterfeit

Exploring that difference in approaches also led us to revisit a theme that’s often come up on our podcast: the healthy and unhealthy forms of “validation-seeking.” For instance, David spoke of founders needing to be motivated by some mix of “external” and “internal” validation:

“Like, if you over-index for external validation, then you're just going to optimize for the flashy announcements and you're seeking hype over substance, you build this hype deficit that has to be paid down… [whereas] if you optimize for internal validation, like, ‘fuck the haters, I'm right, I don't care what anyone else thinks,’ then you just got your blinkers on and you're not listening to your team, you create a toxic environment…”

I took this as an opportunity to clarify what I’ve found to be a common and confusing equivocation between two very different senses of “validation”:

So I think validation is a term that's used equivocally. I think sometimes when we say "validation,” we mean proof; like, can you validate or invalidate this idea? Like, is there actually a market for this? Are there people who actually are going to pay you for this? Can you build this? Validation from reality, in effect. And sometimes when we use “validation,” we mean another person's impression as a substitute for your own judgment. We mean something that I think is actually a counterfeit of the first thing. We mean, like, well, I want to know that you think I can be a founder, so that I don't have to actually judge it for myself, because I don't trust my judgment, and I don't know how to decide. But you, because you're not me and you don't have my biases, like, somehow you'll be able to tell….

Those to me are fundamentally different sources of motivation... [where] the one easily mimics the other, but can be disastrous to the extent that we're not realizing the difference. And I think with it comes another axis... which is the extent to which you've formed your own authentic vision of something you really want to build. Like, the extent to which there's something that you can say, "I want this to be in the world." Like the kind of Steve Jobs, "I want everyone to have a bicycle for the mind. And I can just almost see, you know, it's going to be beautiful, and it's going to be symmetrical... and it's going to have this nice, lovely touchscreen." Like, "I want to make this thing exist," versus "I'm avoiding a bunch of stuff. I'm avoiding failure, I'm avoiding bankruptcy, I'm avoiding disappointment, in myself or in other people..." To me, that's [also] a fundamentally different motivation, [which is only possible to form if you’re consistently on the premise of seeking genuine validation from reality, not its counterfeit.]

And if… you can actually form your own judgments and trust them enough to act on them, to bet on them, and those judgments are pulling you toward a vision of something you want to make real—then you'll also be able to do the things you're talking about, David, where, like, sometimes you need to [gather more customer feedback], and sometimes you need to [tune everyone out.] Sometimes you need to be a wartime CEO, and sometimes you need to be a peacetime CEO. And sometimes you need to be vigilant because you're about to run out of money... but, like, all that will fall out of these fundamentals of, I'm looking at reality. I'm using my own judgment, and I'm doing whatever it takes to build this thing I really want.

4. Entrepreneurship is not for everyone—but thinking entrepreneurially is.

To the question of whether “everyone should be an entrepreneur”, David said:

“Absolutely everybody should be thinking about their own lives, their own decision trees, in terms of: should I do the thing inside the system? Or should I build the project outside? You know, should I do something different? …Like, every single person in the world should be approaching their lives from a position of, how should I uniquely break the conventional wisdom or the institutional status quo to do a thing that interests me or I find curious?”

As to whether this decisional process should specifically lead you to start a company, “it's a very personal decision, that's a very economic and circumstance-based decision, should I go and do that versus stay in a job?”

The specific decision to start a venture-backed company is one that makes sense for a only a relatively small number of people who find themselves in certain relatively specific circumstances. Quoting David:

“the people who choose to step up and take substantial amounts of venture capital money and take substantial swings, do need to [be able to say]: by taking this capital, I'm making a commitment to myself, to my team, to my investors, that I'm going to really step up and take a swing. And to be aware that that will come with pain, that will come with a long-term time horizon, that will come with a set of expectations of you, both internally and externally. And that that is not for everyone.”

By contrast, David also spoke of the increasing number of founders in his community who are starting their own companies by bootstrapping (i.e., using their own funds) instead of seeking external investor funding:

“A lot of those—and this is refreshingly more of a trend of late—a lot of those people who do go on to start companies are thinking more about bootstrapping them. And maybe they're a freelancer, maybe they're a creator, maybe they're building a small, vertical SAAS business online or a small tech-enabled service locally.”

…More common among repeat founders, people who have perhaps some of their own capital to start with, maybe they come from a position of privilege, others coming from a position of, well, I don't need to raise as much anymore because I've got AI at my disposal, I've got smaller, more highly leveraged teams, I've got, you know, a faster route to revenue coming in.

Alice elaborated on the tradeoffs involved in starting a venture-backed company, particularly with the changing economic landscape:

If you're taking venture capital money, you sort of have to increase your risk of failure. You know, VCs will only invest in a company where they believe that there is a small chance of a massive return. And for VCs who have a portfolio, they don't care if 90% of their portfolio fails. And I think often venture capital is seen as the glossy glamorous route. And we, we build venture backed companies; EF is venture backed. But it is a very different route to build companies. And we're recording this in 2023. I'm very curious to see what happens over the next couple of years. The venture capital market has changed, its contracted significantly. And the push now is to build businesses that can generate revenue and generate profit. Now, if you aren't used to work with VC-backed businesses, you might say, "Hang on a minute, isn't that what business is about?" For the last decade, it's been a push for growth, growth, growth at any cost. And I'm curious to see what will happen to the type of founders that start coming into founding high growth businesses where there's just a slightly different onus on what the business has to do: "I need to build something that people want pretty fast in a way that makes money."

This resonated with David, who reflected on how On Deck’s business model has positioned it to be more focused on supporting the individual and their journey than the company:

There's something which, more by accident than by design, when we reflect on the OnDeck journey, we've designed ourselves such that the individual and their journey is our focus, as opposed to the company. And what that allows us to do is take a cohort of people, say 100 people, and help them, or help build a community that helps them, rather, find the right outcome. Now the right outcome might be selling the company, but it might also be shutting down the work they've done so far and joining someone else's company, it might also be getting another job, it might also be being an angel investor, starting a not-for-profit; all of those things are deeply aligned with our interests.

Adding his own reflections on the changing economic landscape and how it is shaping startup culture, David observed of the most recent On Deck cohort:

“My quick take is that the need for very early stage ‘get off the couch’ capital increases, because most people don't have the ability to sustain themselves for 3 to 12 months, while they get that initial product-market fit; I think that the need for huge amounts of growth capital for a small number of frontier businesses increases; more companies that need to load up on GPUs, or do innovation in atoms, building things in the real world; but that is a decreasing segment of the total number of companies started. [And then] there'll be this huge increasing segment of companies that might need that initial capital, but don't need anything beyond that. And I'm really, really curious to see how the market evolves to respond to that, whether it's a new form of financing, [or] whether it's a new set of institutions and credentials that come along with it.”

In sum: entrepreneurship, in the narrow sense of running your own business (much less your own venture-backed business), is not for everyone. Indeed, the very meaning and standard model of “entrepreneurship” is a fast-moving target.

What is for everyone is thinking entrepreneurially—actively, deeply, rationally, from first principles—about whether and what kind of entrepreneur you want to be. For some people, in some circumstances, this might mean taking a job within a well-established institution like McKinsey; for others it might mean going outside established institutions and starting something new, with or without investor funding; for others it might mean going to school, or taking time off to raise kids, or waiting tables to make ends meet while learning to code or auditioning for acting roles or working on a novel. No one is ultimately more qualified than you to judge what particular path to take, or what advice to follow, or what institutions to accept or reject. Just stake awake to the fact that it’s your life on this earth you are building—and then choose accordingly.

Full episode transcript with timestamps (paid subscribers only):

Alice Bentinck  00:23

Welcome back to the founders mindset. The podcast where we deep dive into the psychology of founding a company through the personal stories of the founders themselves. I'm Alice Bentinck, co founder of entrepreneur first, where we invest in individuals to help them find a great co founder and divide their ideas into a successful startup. I'm joined by Dr. Gena Gorlin, a clinical psychologist, founder coach and faculty member at the University of Texas at Austin, who's been collaborating with us to better understand and support the psychological needs of early stage founders. Hi, Gena.

Gena Gorlin  00:54

Hi, Alice. In this episode, we had the pleasure of speaking with David Booth, the founder and CEO of OnDeck, a curated community designed to increase your odds of building a successful venture-backed company. Now, if you're thinking that sounds a bit similar to Entrepreneur First’s mission, you wouldn't be far wrong. Both organizations share a belief that the world is missing out on some of its best founders, and a passion for catalyzing globally important companies by reducing the barriers for the world's smartest and most ambitious people to go and found them. In this conversation, we talked about how David's parents raised him to be entrepreneurial from an early age, why founders need community before they need advice, the mistake of seeking external validation and credentialism as a way of outsourcing your own judgment of readiness, and a lot more besides. So without further ado, here's our conversation with David.

Gena Gorlin  01:47

Thank you so much, David, for joining us. I would love to just jump in with your personal story. Because, as we know, you're both a founder and in a sense a meta founder, right? As someone who—and I know Alice can really relate to this—as someone who founded a company for founders, we can learn from you at two levels: we can learn from your own personal story. And we can learn from just all the accumulated pattern recognition and what you've learned about your customer, in running your company. 

So could you just tell us first a little bit about how you ended up founding OnDeck, how you ended up as a founder yourself?

David Booth  02:25

I'd be happy to and thanks for having me. I agree, to start with, there is something very meta about building a company that builds companies, and hopefully that chain continues forevermore. I often describe OnDeck as my life's work. It's a culmination of a lot of different threads throughout my career, a lot of different early influences, a lot of sort of the "be the change you want to see in the world." For me, I had a lot of early influences that we discussed in the past that I think have sort of helped to set my mindset around building as opposed to “working,” from a very early day. 

There was one moment that I do remember distinctly from, I think I was around 12 or 13. As a young go-getter I started importing iPods into New Zealand, where I was living at the time, buying on Amazon and reshipping to our local eBay equivalent. And it worked for a while, I imported batches of 5 and then 10. And then I got more ambitious and teamed up with a friend of mine, to raise a little bit of money from both of our parents, and buy a really big shipment of iPods on Alibaba. We promptly went to Western Union and sent a lot of cash to somewhere in China, we believe, [which] obviously never turned up again. 

And it was actually what happened next, which was one of the formative moments of my mindset, I believe: upon losing both the business I'd built and the capital I'd invested to go for it, [I] had a conversation with my parents, who took the opportunity to sort of convert it into a teachable moment and say: "this is how businesses can work. And there's this concept of limited liability; what you should really try to do is get back out there and build another one and try to make it back."

David Booth  04:16

And I contrast that to my friend's story, [whose] parents said, "no, you can't lose money like that, you have to go and get a job and earn every dollar and pay us back." And I was actually reflecting [on that] story with my parents recently. I’d forgotten this entirely but my father reminded me of what my comeback business was, which was this idea that—apparently our house needed painting. And my father had had some quotes come in from contractors, [and] he gave me an offer to bid against the contractor. No favoritism, he said: the price has to be competitive, the quality has to be on par. I have to buy my own equipment, buy my own supplies, hire my friends. And [I] did that, and ended up making four or five times [more than] the friends who I was paying an hourly rate. And it was like, you know, to a 13-14-year-old, a very, very clear life lesson, certainly one that I've been reflecting a lot now as a parent and how to create the kinds of conditions that foster that kind of learning environment, without necessarily having to have the adversity (that's nothing, nothing that any parent wants to create). But it's a kind of position that I certainly think a lot about.

Alice Bentinck  05:27

I mean, kudos to your parents! I feel like we need, how can we encourage more parents to take that approach? 

One of the things that we talk a lot about is the founding career path. And this idea that so often people see founding as a moment in their lives, and they take that one attempt at being a founder, and it either goes brilliantly, and they become Mark Zuckerberg, or they fail, and they never do it again. Whereas actually, as you say, founding is something that you try multiple times over your life, and hopefully you get better at it, the more you try and [the] more experience you have. And your parents did use such a service to basically teach you that the founding career exists and is aspirational and a great thing to be part of, rather than your friend, who had his one moment as a founder [at] age, what were you 16-18?

David Booth  06:09

Earlier, I recall it being 13 or 14.

Alice Bentinck  06:12

Oh my goodness, that was just one founding moment. I think so many people see it that way. Whereas really you have shown it's a career path.

David Booth  06:21

So I think there's something to that. And the way I reflect on hindsight, [there] are lots of little opportunities to, what is more commonly known in the tech sphere as exit versus voice, or to sort of, to follow conventional wisdom within a system, or to break out and build something outside of that system. And when you really get into the details, there are so many opportunities, whether it's like, well, my friends and I are going to go to the same music festival as everyone else, or I'm going to organize a house for my friends, and we're going to go have a party there. Yeah, for the New Year's holidays, the classic thing in the southern hemisphere, anyway. I think that I had a few of those moments. And I've shared some of this with Gena in the past as well. But going into university, I actually had like a little bit of a negative experience. When I first landed there, at a University Hall, many others straight out of school, I'd taken a gap year, I thought I was better and different and didn't really hit it off with people. And I remember a moment where I actually thought—maybe this is projecting in hindsight, but I distinctly remember saying—"should I invest in fitting in here, and like joining and climbing the social hierarchy? Or should I go do something else?" And I did the latter. And I, I started a small clothing company and an events company while I was studying. And I made a bigger, broader group of friends as a result. And it all worked out: I wound up making friends with some of the folks in the hall anyway. But it was that moment of, like, what is the expected path? Graduate, be a lawyer, be a doctor? Or what is the opportunity to exit that expected path and do something different? And that's how I constantly prompt myself now, and those around me. And I don't think there's any one single answer, but I hope to see more of that.

Alice Bentinck  08:13

It's such an interesting thread, isn't it, of how hard it is to take the non-legible path, because you're not just doing something different, you're actually—as you say, and so beautifully articulated—you're rejecting your peers; like, you're basically rejecting the opportunity to make friends with them. And in some ways, commenting on their lives to some extent, as in by you not joining in with I don't know, whatever the boozing or party culture or whatever the university culture was, where you're at, you're slightly making a comment on that, and it does make it harder to fit in and have the normal peer structure that I suppose is expected. Harder for your parents, harder for... So it's just interesting how there are so many barriers to not taking the normal, legible career. And actually you need a reasonable amount of... well, I suppose what do you think it is? David, what do you think that you had that meant you were happy to push back on on the legible, normal, usual, whatever, you know, path?

David Booth  09:11

I mean, in many cases people don't have a choice; maybe I just wasn't cool enough [laughs]. So I had to take the other path. But more serious, more real examples [are] people who don't have the privilege of going within the existing system; they can't get into the right college, they don't have the right capital or backing or support system in their lives to follow the conventional wisdom, so they have to—you're a new immigrant to a new country, you've... dropped out, for whatever reason. So I do, and this is something where, Gena, I'm sure there's a more intellectual approach to it. But the idea of the outsider, the individual with a chip on their shoulder or something to prove. There is a thread I'd love to pull around the desire for acceptance, whether it's acceptance from your peers, or acceptance from your expectations of yourself, whether it's an internal or an external motivation that drives an individual to do something that could be seen externally as more ambitious than otherwise. But to them, it might have actually been, like, the only way.

Gena Gorlin  10:23

Yeah, I'd love to pull on a few things about that one. It's interesting to hear you describe it as a kind of almost forced choice for the misfits, for the outsiders, for the immigrants. Because the way I see it, there are many, many, many more misfits who don't become founders than who do. The vast majority of people who don't fit in college, who experience adversity, don't become entrepreneurs. Just as the vast majority of people generally don't become entrepreneurs. What's hard about becoming entrepreneur, like, it's never a default. Right? And I think there's a version of the story where we could almost see it as, well, if you can't do any of these conventional things, I guess, what you're left over with is go found venture backed startup. But, that's never the default. And I think part of what's so hard about it, is that, unlike all those conventional paths, where you could have been a doctor, you could have been a lawyer, you could have fit in in these ways, like, this path hasn't been charted for you. Now, you both, with your current ventures, are trying to chart a path to some extent; you're kind of creating playbooks, you're creating frameworks, you're creating a community to make it a little bit easier to kind of mimic the kinds of subcultures and standard progressions and even status hierarchies that we have in other fields that are already established, such that someone could decide, oh, I guess this is something I'll try. I'll try to be a founder. Right? But I think it's like, there's something about it that still doesn't fully describe the journey. And I can't help but think of, I was just listening to an interview with Marc Andreessen, mostly about AI. But he said in passing something that has kind of been haunting me ever since, especially given the work a lot of us are doing, which was in effect: Lex Friedman asked him, so what advice would you give to people out there who might want to be founders, or you know, like young aspiring founders? "Well," [Andreessen said], "if they need advice, they probably shouldn't be founders." Like, founders hate advice. They don't take advice. They don't care what I have to say; like they're doing it for reasons of their own, and they've got, they're on their path. And your story, David, reminds me of, like: what your parents in a way taught you was, don't assume that you have to do it this way. Like, there's this other way to do it, right? Like, go and try stuff.

David Booth  12:50

I love it. Yeah. And I mean, to your earliest question about, sort of, "why," I think EF and Alice and Matt deserve a lot of kudos for their work over the past decade. It's been inspiring to see. I mentioned On Deck, to me, is a combination of a lot of different threads. To me, like, the bulk of my career has been spent building products for founders to remove friction from their journeys. I landed at AngelList in early 2014, leading the syndicates product, helping scale what is now the funds product, and build the momentum around that ecosystem. I jumped to Carta as the head of international growth, helping founders manage their cap tables on the thesis, the principle that if they could bring, you know, have a record of ownership of truth of the company, then they could better incentivize employees, raise capital, bring liquidity into private markets. Along the way, there's been so many opportunities to... take founders, people who have already opted into this crazy journey, and help them accelerate their journey. But there was never really anything along that journey that was saying like, how do you solve getting more people in the funnel in the first place? And I do remember, so I'd moved to London in 2014-15. And I remember being very inspired by EF at the time, and thinking that for all of the incredible value you create, it still requires a huge commitment to take the leap to join. And meanwhile, my friend Erik Torenberg had announced On Deck and launched this community, where we were like, the specific problem we wanted to solve was just to create some magic at that moment of vulnerability when you're thinking about leaving your job to start something. You haven't quite taken a leap. And you're not quite sure if, I mean, maybe you do have very high conviction and the idea, but you're not quite sure about the people you're working with. You don't know where your first customers are coming from. Like, what is the community we can build right at that very moment that can help more people take the leap with the right initial founding team, the right initial group of advisors and investors, possible customers around them? And it was just that for, you know, two or three years: it was a community. It was no business, no fund, no anything else, just, like, different people like myself benevolently motivated to host these dinners every month. So a lot of, you know, what's flowed since then, and really, a lot of what we've brought everything back to today, comes back to that same idea of, you know: we (and I think we're very aligned in this) think that... startups are one of the highest leverage ways of creating an impact in the world, more people starting more companies is a good thing, but we want to make sure that they work... have the right community around them from the very early days when they get going, in part to solve, as you said, Gena, like: why aren't more people doing this? What was missing from their lives when they didn't take that leap?

Gena Gorlin  12:51

Yeah, and part of what I want to explore and maybe push on is, how many people should be doing this? Because, I've really resonated with both of your missions, right? I mean, I've done work with EF. And I'm just so thrilled at the fact that companies like yours exist, because I do think it ought to be easier than it is right. And I do think that a community and a set of supports and structured guidance can be extremely empowering. I want to see that in the world. And I'm often faced with this tension: that it's so easy for it to become school-ish, so easy for it to seem easy. And I know, I mean, we've talked about this, Alice, with people who go through your program, who are so excited that they've been accepted into this program. And now they have a stipend, and it's a sure thing for eight weeks where they just are going to be told how to be founders, and... they're going to be on a scoreboard, and they're gonna get their sticker at the end of it, and they'll win the, you know, investment committee hearing. And now they're just so completely departed from what it means to be a founder. And I think there's ways EF has been pushing back on that tendency. But I don't think it's EF's fault; I think it's inherent, it's just such a natural default. And, and I think we have to kind of think about that: like, how do we convey the ways in which this is hard and a choice? And perhaps help people make the choice in either direction, right? Like, are there people to whom we should be saying, maybe don't be a founder, because you're not in it for the right reasons?

Alice Bentinck  16:49

Well, just to link this to the Marc Andreessen comment that, you know, the best founders don't need advice: mimesis is real; like, the idea that the people around you will influence your preferences, choices, desires. And this, I think, is particularly true around founding, and where, if you are based in Silicon Valley, and you're surrounded by the world's best founders, best VCs, knowledge, early startup employees, etc, you will probably learn, most of the time, the right things to do. I think there is a bigger challenge when your ecosystems are much more nascent. And where there's a lot of information out there that probably isn't quite right about how you start a startup, a lot of what you absorb from people around you might not actually be best practice. So I think the kind of Marc Andreessen perspective is very, very Silicon Valley focused. 

Alice Bentinck  18:30

And I would say this is true for the comment around who becomes a founder. If you're in Silicon Valley, and you're like, oh, I don't know, should I become a founder? Should I not? Like, is there someone to hold my hand? You're probably not a founder. If you're in London, or Paris, or Singapore, or wherever it may be, going, "Oh, I don't know if I should be a founder or not," that's probably a viable question to ask. Because for the entirety of your life, you've had people telling you, "do not do that. Do not do that. Go become... an APM at Google, whatever it is, a legible career path. And so I do think, you know: I'm still very much in the same camp as David that the world is missing out on some of its most ambitious, high potential founders, purely because [of the] culture that they're in. Now, I do not think everyone should be a founder. And, David, I'm interested in your perspective on this as well. I think there's a very small number of people worldwide, who can be a globally important founder. But, still not enough of them are even trying.

Gena Gorlin  19:22

That's a really good point, Alice. And, just to connect the dots and then I want to hear from you, David: it's not an accident that you told us that story, David, of how one of your formative experiences was getting a certain message from your parents early on about what's possible and what's okay to try. So I think, speaking to your point, Alice, the messages that you internalize from your culture matter.

David Booth  19:51

There's a writer I want to shout out, a friend of mine, Henrik Karlsson, in a blog called "first we shape our social graph, then it shapes us"... It just takes the idea of "you are the average of the five people you spend the most time with," and makes it more intentional. And introduces this idea of a milieu, which, Gena, you are part of my extended parents milieu. It's like the word that internalizes... It's the particular set of cultural inputs that influence us, and makes it more intentional. How do you go out and seek out people who you want to draw from culturally? And this has always been something that has inspired me around On Deck; I've said, you know, the best way to get from A to B, is to go out and find a group of people who are all going from A to B, and get on that journey with them. And that was a thesis that guided our growth through 2020-21, mid-pandemic, [when] everyone is out there, locked down and sheltering in place, and lacking the opportunities to connect with others who are founders leaving their, starting their journeys, or scaling, or looking for new jobs, or looking to start angel investing, or all of these other journeys. And so when I look at—founders don't need advice; it's not like, advice is often this very explicit, "find the person who knows a thing and can tell you a thing." To me, it's much more implicit, [it’s] surrounding yourself with others who have been on similar journeys, who are going on similar journeys. And it's the sort of feeling of being connected into that directional graph, which is actually what you need. And that's what, as Alice says, Silicon Valley has by default, [and] that's what most other ecosystems do not. And I particularly feel that, having been from New Zealand, the first chapter of my career was in New Zealand, it's very isolated. And in particular, most of the ambitious people here figure out quite early on that they need to leave to go and capture the opportunity of their lifetime. They've moved to London, Singapore, New York, San Francisco. And so our, you know, the New Zealand diasphora is, around 25% of our population lives overseas. And often that is the most ambitious, you know, successful ones. Which is a problem when you think about people who are going through college and looking for mentors and role models locally and haven't yet had the opportunity to sort of to step outside of that fishbowl. So there's a real, real opportunity in that.

Gena Gorlin  22:20

I feel like, maybe a distinction to be made, is between a supportive environment, an ecosystem, that nurtures a certain kind of agency, versus a supportive environment of the sort that removes or creates the illusion that you don't need that agency; or that kind of creates a cheap substitute for agency. And I think I've seen both. And I think it's really subtle how a given person interfaces with an ecosystem. And you can kind of tell that there are these two very different approaches that they might be taking: where certain people, they leverage the network, and you see them kind of "turning on": like, you see them as like, they hungrily take the advice and the resources, and they make it their own, and they do something with it that you didn't even expect. And they go and make these calls that are totally different from the calls that you've discussed having them make, but like actually make more sense than whatever you were originally suggesting. Right? And you just see, okay, they've, like they've been activated, the fire has been fully lit within them. Like, maybe you saw the spark and you lit the fire, and like, now they're off to the races. Versus, like, each step is like pulling teeth. Like, you're giving them another thing to do, and another thing to do, and they're coming to you for the next thing, right? That isn't going to work, at least if what you're trying to do is found a company. I'm curious if the two of you have seen these two approaches? And you know, if you could just comment on the difference and maybe how you can tell?

David Booth  24:03

I mean, I've certainly seen it, I wish I had a better answer for how to foster it. I think that would be the the magic bullet, if there were one. The only thing I know that we can do for sure is identify it in every category, or at least make our best effort at identifying it in applications and qualification criteria. And also in setting the cultural values for people who may not even realize that they should be operating in a certain way, to sort of come out as a group. One of the things I say a lot is that our main job is to get the right people in the room, just create the conditions for you to support each other, and then get out of the way. You're not here to learn from us. You know, I'm no expert. We just think of operating within a community as: you need to be selfishly motivated, to the extent that you put value out there into the community, you contribute to it, you host a session, you teach people, because that's actually the best way for you to get the most value from it. It's one of the cultural components. So yeah, I'd love to hear from Alice on this as well, because I think this is a really critical, really core component to EF. I don't have, like I said, a magic bullet as to how to foster that spirit and drive, more than just to help to get the people who have the smallest spark of it together and help them realize that together.

Alice Bentinck  25:33

I love that point that, ultimately, it is about bringing people together who can role model for each other what good looks like. I think that can support people who already have this as an intrinsic, but it might be a latent intrinsic. And so the group or the community is the catalyst for that. Can you inspire people who don't have that? I mean, probably; now, and I say this as a parent—I think we've all got young young kids—probably goes back to parenting, right? And, like, how we were brought up. And that's pretty hard to fix when we meet them in their 20s.

David Booth  26:10

One way that, as I say, when you think about interviewing, qualifying, taking... and any investor, whether it's EF or YC or a fund, one of the things they've got to do is really try to get under the skin of the founder and understand what drives them. And I sort of had an epiphany, I suppose.... Around three or four months ago, I've been a part of this group called Leaders in Tech, which—shoutout to them, I'd recommend them for scaling stage founders who want to invest in their interpersonal skills, and understanding and managing group dynamics—and one of the things that sort of sitting there in this room and observing this group of 14 other late stage founders, all interacting, all sharing a lot of sort of the raw emotion of what drives them: there was actually this clear differentiation within the room; there was a couple of people that were clearly driven by more of an external validation or acceptance, like... "my family looks up to me and respects me, and my friends think I'm killing it; I need to keep killing it, because everyone thinks I am." We had another person who I distinctly remember having this, like, internal validation, drive for will power, "fuck-the-haters," "I'm just going to keep doing what I'm doing, because I think it's right." There was another one again, who was driven by this, I'd call it, external invalidation, or like this idea that people were out to get him and I need to squash them, like, squash that lawsuit. I'm gonna prove them wrong. But that coming from a sort of a place of pride as opposed to willpower. And then certainly I think, in other scenarios, I've seen almost like, a sense of, like, desperation, and not necessarily in this group, but, like, "I need this to work." Otherwise, my Visa isn't valid, I've got to move home, otherwise my family won't be s-. 

David Booth  28:13

So I plotted this on this 2 x 2 of external versus internal motivations, and validation or acceptance versus invalidation or fear. And I've started mapping a lot of that. And... it was actually that moment that I reflected on it myself and realized that a lot of founder burnout that I've experienced, I certainly have, and seen out there comes from over-indexing on any particular one of those. Like, if you over-index for external validation, then you're just going to optimize for the flashy announcements and you're seeking hype over substance, you build this hype deficit that has to be paid down. If you over-optimize for external invalidation or fear, then you wind up just watching your competitors and like you're living in fear of someone catching up, you're like the cyclist riding, you know, looking over their shoulder instead of the path ahead and going off a cliff. If you optimize for internal validation, like, "fuck the haters, I'm right, I don't care what anyone else thinks," then you just got your blinkers on and you're not listening to your team, you create a toxic environment, demotivating. If you're operating from a place of fear, or defensibility, then you end up optionality-maximizing: you're trying to come up with insurance plans, but before a plan is even figured itself out. You're trying to come up with Plan B. And I've experienced and lived all of those. And there was, there was actually the moment of just being aware and reflecting on them and being able to rebalance them and say, "Well, I've over-indexed on optionality here. So what does it look like to lean into willpower?" And for me, there was some degree of insight from that that led to helping in conversations, before you can give advice to somebody about a specific situation that might be in their life, trying to go a level deeper and understand what's actually motivating them to go into that decision. So not sure if that that feeds back into the question you had, Gena. But it's certainly been a useful framework for me.

Alice Bentinck  30:26

Just to comment on that, it feels like a big theme of this podcast has been validation seeking, and people trying to work out their true intention and motivation versus what is whoever or whomever they're trying to impress. I wonder if this is just thinking about like malleability of different founder characteristics. I'm interested to hear your thought on this. My feeling is that, I'm largely speaking from personal experience, this one feels more malleable, in that... when I was leaving McKinsey, I've always been very ambitious. And at McKinsey, it became clear that the way to succeed was to make your manager love you and get a really great performance review. And then you would be, like, you get the top rating or whatever. And, and when I was leaving, because I found it very hard that now I was going to be producing work that no one was going to look at. And it took me about a year to—and Matt, my cofounder, used to literally just look at my work and be like, "well done, Alice, you've done a great job. This is great!", because I so desperately missing that kind of external approval that I was doing the right stuff. You know, after about a year, I probably got over it. But, Gena, how much can you actually influence that internal intrinsic motivation?

Gena Gorlin  31:37

Yeah, so David, you and I have talked about this a little bit and could geek out about it forever, I know. As you know, I think a little bit differently about these axes. So I think validation is a term that's used equivocally: I think sometimes when we say "validation," especially in like a startup context, we mean, proof; like, can you validate or invalidate this idea? Like, is there actually a market for this? Are there people who actually are going to pay you for this? Can you build this? Validation from reality, in effect. And sometimes when we use validation, we mean, another person's impression as a substitute for your own judgment. We mean, something that I think is actually a counterfeit of the first thing. We mean, like, well, I want to know that you think I can be a founder, so that I don't have to actually judge it for myself, because I don't trust my judgment, and I don't know how to decide. But you, because you're not me and you don't have my biases, like, somehow you'll be able to tell. Or, like, the Twitter world will know somehow better than me based on how many likes they gave my post, or how many followers I've accrued. Those to me are fundamentally different sources of motivation... [where] the one easily mimics the other, but can be disastrous to the extent that we're not realizing the difference. And I think with it comes another axis... which is the extent to which you've formed your own authentic vision of something you really want to build. Like, the extent to which there's something that you can say, "I want this to be in the world." Like the kind of Steve Jobs, "I want to make a dent. And this is the dent I want to make... I want everyone to have a bicycle for the mind. And I can just almost see, you know, it's going to be beautiful, and it's going to be symmetrical... and it's going to have this nice, lovely touchscreen." Like, "I want to make this thing exist," versus "I'm avoiding a bunch of stuff. I'm avoiding failure, I'm avoiding bankruptcy, I'm avoiding disappointment, in myself or in other people..." To me, that's a fundamentally different motivation. 

Gena Gorlin  33:52

And if you have the first two—if you have the kind of first handed, if you can actually form your own judgments and trust them enough to act on them, to bet on them, and those judgments are pulling you toward a vision of something you want to make real—then you'll also be able to do the things you're talking about, David, where, like, sometimes you need to, like, get more focused, nose to the grindstone. Sometimes you need to be a wartime CEO, and sometimes you need to be a peacetime CEO. And sometimes you need to be vigilant because you're about to run out of money and sometimes... but, like, all that will fall out of these fundamentals of like, I'm looking at reality. I'm using my own judgment, and I'm doing whatever it takes to build this thing I really want.

David Booth  34:39

I like where this is going. And I mean, to me that just reinforces the idea of different sources of motivation that you need to draw on and be able to move between at different times based on where you're at in your journey. Based on what the needs are. Do you need to dig deep and draw your willpower? Do you need to pull that all nighter, but from the act of desperation? I love that comment. 

David Booth  35:04

One thing that you shared as well, [is], I think, an individual's desire to seek external validation as a way of outsourcing their own judgment of readiness. One place this regularly shows up is in very talented people who [are] sort of seeking the next level of credentialism as they go, credibility or badge collecting, if you want to be cynical. I went to a great high school, and then I got into a great Ivy League university, and then I got a job at McKinsey. And then I got a job in investment banking. I went back and did an MBA, and then I went back and, you know, there's always a "next thing." And one thing that I don't have a very strong opinion on, but that I know that at some point, there's sort of... you climb ladders, and then you've learned enough where you need to get off that ladder and go build. Sometimes, in some industry, it actually makes sense to climb further; like, [if] you want to build a FinTech company and go into the depths of finance, maybe it does make sense to go and have a career in banking first. If you want to build something that's like a social app for Gen Z, maybe you should do that when you're 18 or 20. And try and fail a few times. So I don't think is a perfect answer. But there's definitely a connection between people who... don't trust their own judgment, don't put enough weight on their own judgment that "now is the time that I can take the leap and go build." So they'll look for an additional form of validation, additional credential, climb that ladder a bit higher. And for a lot of people, they get stuck there, they get trapped; the "golden handcuffs" are on, you're going to have some mortgage and everything else. And the investment banking, salary is a necessity. So there's a sweet spot where organizations like EF, like what I'd love to build with OnDeck, can help people realize the right time to hop off that ladder for them. To help—I would never tell somebody that they should be a founder, but for somebody who is curious, I want to, you know, help them take the leap themselves off of that ladder at the right time.

Gena Gorlin  37:21

Yeah, for sure. And I think there are two very different processes that could lead you to take the leap that might look superficially similar. And you might be wrong on both processes. Or you might, like, accidentally luck in and this is the right time. But: did you take the leap because you judged it right? Maybe for terrible reasons; and maybe with a lot of input from a community, from a resource, from OnDeck or from EF; but did you judge it based on reasons that now can go and be tested? Because now you're going to try and you're going to check your hypothesis against the world, like you think that you can build it now, but maybe you can't, because there were unanticipated ways that the technology is more complicated, or you realize you need these skills first, so then maybe you go back to school, you course correct. But: is your judgment ON? Like when we were talking before about, there's that founder who takes what you give them and then they build on it. And clearly there's a fire that's been lit from within, versus there's the schoolish kind of, okay, tell me the next thing. Tell me the next thing. I think it's the same for, like, what do you what do they do with your advice? Like, do they take it and process it through their own very personal context, and say, "Yeah, you know what I hear you, but like, I'm actually going to go ahead and try it anyway", or, "I hear you, but I'm actually going to stay in school for another two months, because I have a hunch that after I've taken this class, it'll open up this network"; and they might actually be wrong, but the fact that they're doing that is a really good sign. The fact that sometimes they might disagree with you, and then go see the hard way that you were right, is a good sign.

Alice Bentinck  38:57

Which, all this brings us back to Marc Andreessen's comment again, about like, whether founders need advice or not. This, I love this framing, Gena, of the context filter. And, I think founders often feel overwhelmed with advice. Even pre-founders, you know, if you're thinking about quitting your job, the amount of advice you'll get from different very well-meaning very well-intentioned, often people who are highly interested in your life, as in your partner, or family or friends, you will get so much advice from them; but only you know what context filter you want to use. And I haven't thought about it as a context filter before, but I really think that framing is very, very useful. 

David Booth  39:32

I'd be curious if there is any learnings that you could share, Alice, around the structured sort of check-in moments... For example, I've heard in the past from Meta, I think, that one of the most promising signs of a team's future is actually their ability to move really quickly, even if it's not in the right direction. And it's the ability to work really well together, and to, like, they could be going the wrong direction, but they got a lot done. And I wonder if there's a correlation between, or anything you've learned from the advice given to teams that you've seen move really quickly, versus the advice given to teams that aren't moving quickly? Or maybe to correlate that to successful stories, or how you've evolved your interactions with these founders over time?

Alice Bentinck  40:26

Yeah, interesting. I mean, I think the reason why we are so obsessive about productivity for teams is because we build these inorganic teams. So you know, building a startup from scratch, finding a co-founder from a pool of selected individuals, we are obsessive about the quality of those co-founder connections. And the best teams move really fast. The bad teams don't. We were doing investment committee actually, yesterday and the day before. And we just funded a bunch of teams where the idea is definitely... not particularly good. But we think the team is really interesting, and they've moved very fast in a short amount of time. But to your point around the impact of advice, I would say advice nudges them; it does not dictate their success. The most important advice we give actually is acting as a mirror. So particularly for a team that isn't particularly effective. One of the interesting things about co-founding teams is that, by the time someone gets married, they've usually had multiple romantic partners, and have formed some sort of mental model of what good looks like. Weirdly, with co-founders, most people find a co-founder and are like, "cool! Sign the co-founder agreement, we're all in." So largely, the role that EF is often playing from an advice perspective is saying, I've seen lots of teams, I've seen lots of co-founding teams. This one is not in my top quartile. These are the reasons why: you're not productive, you're talking over each other, you don't seem to have any respect for each other. And so it's more that sort of nearer and nudge of "let me give you the context I have, which is I know a lot about what co-founding teams look like, and let you use that information to make the decision for yourself." And so it's often, I think, it is very hard. And it's interesting watching people who've been on the EF team who've given huge amounts of advice and mirrors and nudges then found startups themselves: you can't be your own mirror. And even if you know exactly what you're meant to be doing, you can't be your own mirror; you need somebody to be the person who provides the mirror, holds the mirror up.

David Booth  42:22

That's great. There's probably some law of diminishing returns, how, like, the more somebody proposes to give you specific advice versus, like, be the mirror, help you reflect your own motivations and come to your own realizations. And connected to that would be, founders need some degree of naivete to take on a really hard problem often; like, if you go and find all of the experts in the sector, and ask them about a problem to be solved, they'll tell you all the ways that can't be done. In fact, more helpful is to have somebody who hasn't been disillusioned by all the problems in the field, is willing to charge into it and can have a guide or a coach that can help them reflect and learn and iterate faster, as opposed to have traditional advice come in from an otherwise, you know, trusted, reputable source.

Gena Gorlin  43:10

Yeah, that's great. I mean, the naivete is really interesting. Because coming back to this theme of, what do you assume about the world, and particularly the social world? Like, these are the five careers that are allowed, or I have to be making this much money by this age, because that's what everyone does, or that's what everyone in my family expects; versus, like, the Steve Jobs spirit of realizing "everything you see around you... that you call life was made or made up by people no smarter than you, and you can make a dent, you can change it..." There's so much more that's changeable than you realize. And I think the naivete you're talking about is largely a kind of—like, sometimes in psychology, we'll call it "beginner's mind"; like, being able to strip back some of our default assumptions, and the kind of lenses through which we see the world some of which just may be limiting, may only give us part of the picture. I think it's really a wisdom we're accessing, when we pull back from our kind of dense structure of default assumptions about how things have to be, how this institution has to run. And just start thinking fresh, think from first principles. Okay, but how else could you build a rocket? Or, what if this was just a totally different kind of business?

Gena Gorlin  44:37

To pick up on another theme that feels connected to a bunch of stuff: on the point of that we can hold up mirrors, and we can use our knowledge of existing patterns to provide the accumulated wisdom, of experience and pattern recognition; and that that's really important for especially early stage or first time founders to take seriously. I'm remembering in Paul Graham's essay where he compiled a bunch of responses he got from prior YC alumni when he asked "what was surprising to you about running a company or about being a founder?" And the biggest surprise was that nothing they said should have been a surprise. Like, these were all things he had literally said to them during their run. So, the kind of the takeaway was, "Okay, so just having heard me say it once doesn't necessarily mean that it's sunk in." But I feel like, more so than just kind of hearing it, or more so than, like, the distilled takeaways, they're seeing a bunch of exemplars. I keep coming back to this as a major value that I can provide, and that I think EF provides and OnDeck provides to young, scrappy, hungry would-be founders. Just like: look at all these different ways that people have done it. Look at all these different ways they failed. Like, providing the data set; not just kind of telling them, okay, "I've noticed that, when a team isn't talking, when a team looks like the two of you, it's not going to last"; rather, like, "let me introduce you to Paul over here, who had a great run with his co-founder for five weeks, and then it all blew up. Listen to his story." That has an impact that's closer to the kind of vicarious learning that I think can almost substitute for personal experience. And I think even more importantly, hearing the stories of people who've taken their own weird, crazy, circuitous paths, and really done it. And like seeing the range—both seeing like, oh, every story is different. So mine is going to need to be different too. But also, every story, like at some point, the founder has a reckoning. And in every story, at some point they discover that this is a new low that they can survive, and they didn't think they could survive the last low. And now this is a new low and look, here they are, they're still in the game. Hmm. I can learn from that.

David Booth  47:24

That same learning can be through the creation, certainly, of various founder groups, and in the participation in many of those as an individual, as a founder myself. And I shared the anecdote earlier of the Leaders and Tech group; we had one called OnDeck Scale at a point, which was for individuals to come together. And, you know, in speaking with with them, I think everybody would share a similar sentiment of, you can read something on a blog, you can hear it on the podcast, but actually having a connection between a small group of people who have that moment of intimacy, of sharing, like, what the journey has really been like, of realizing that others are on that journey too or similar versions of that journey too, and to balance, like... one of the things I struggle with is support groups or therapy, some of them can become almost like therapy groups, and people are airing their, their grievances together. To me, it's balancing, how do you express the empathy of the journey that others are on, while also balancing the intellectual curiosity of the conditions that went into their journey, in order to get something out of it yourself? For me, this is one of the hardest things today. It was it was like, a really unsatisfying conclusion that I came to, which was based off of... remember, Gena, we were speaking about the Michael Jordan documentary, about how, like, basically, how really hard winning is? Like, if you want to be the best, you have to put in the work; like, really put in the work. And if you don't really put in the work, you don't win. Yeah, don't be disappointed about that. At times, I've sort of felt like there was a lot of people airing grievances of "it's really hard." And in fact, I've wanted to say, "yes, this journey is really hard. That's why you signed up for it." That was also sometimes very unsatisfying. It's like saying, "Do you want to have an easy life, or you want to have a lifetime of pain?" No, I... doesn't have to be like that. And seeing that through the eyes of others within groups has been really beneficial for sure.

Alice Bentinck  49:46

This sort of feeds into another theme that we've talked a lot about across the various podcast episodes that we've done around choice, and like it being a choice to start, it being a choice to continue. David, you said, you know—correct me if I'm wrong—you're not trying to "turn people into founders." It's kind of people that already sort of want to be founders. Do you think we should be doing more active pushing? Or, like, how do you think about this concept of choice, and whether we should be actively trying to persuade people?

David Booth  50:21

Almost anybody should... I'll rephrase that. Absolutely everybody should be thinking about their own lives, their own decision trees, in terms of: should I do the thing inside the system? Or should I build the project outside? You know, should I do something different? The number of those projects that deserve to be companies is limited. The number of those companies that should raise venture capital is limited. You know, the number of those companies that do raise venture capital that are going to go on to have substantial successes is limited. But I want to separate those two things. Like, every single person in the world should be approaching their lives from a position of, how do how should I uniquely break the conventional wisdom or the institutional status quo to do a thing that interests me or I find curious? 

David Booth  51:12

Separately, a lot of those—and this is refreshingly more of a trend of late—a lot of those people who do go on to start companies are thinking more about bootstrapping them. And maybe they're a freelancer, maybe they're a creator, maybe they're building a small, vertical SAAS business online or a small tech-enabled service locally. It's a very personal decision, that's a very economic and circumstance-based decision, should I go and do that versus stay in a job? Ultimately, they're going to have similar degrees of economic outcome, maybe similar or varying degrees of lifestyle changes and commitments. I do think that the people who choose to step up and take substantial amounts of venture capital money and take substantial swings, do need to ask them[selves] that Michael Jordan question of, like: by taking this capital, I'm making a commitment to myself, to my team, to my investors, that I'm going to really step up and take a swing. And to be aware that that will come with pain, that will come with a long term time horizon, that will come with a set of expectations of you, both internally and externally. And that that is not for everyone. 

Alice Bentinck  52:33

If you're taking venture capital money, you sort of have to increase your risk of failure. You know, VCs will only invest in a company where they believe that there is a small chance of a massive return. And for VCs who have a portfolio, they don't care if 90% of their portfolio fails. And I think often venture capital is seen as the glossy glamorous route. And we, we build venture backed companies; EF is venture backed. But it is a very different route to build companies. And we're recording this in 2023. I'm very curious to see what happens over the next couple of years. The venture capital market has changed, its contracted significantly. And the push now is to build businesses that can generate revenue and generate profit. Now, if you aren't used to work with VC-backed businesses, you might say, "Hang on a minute, isn't that what business is about?" For the last decade, it's been a push for growth, growth, growth at any cost. And I'm curious to see what will happen to the type of founders that start coming into founding high growth businesses where there's just a slightly different onus on what the business has to do: "I need to build something that people want pretty fast in a way that makes money."

David Booth  53:45

There's something which, more by accident than by design, when we reflect on the OnDeck journey, we've designed ourselves such that the individual and their journey is our focus, as opposed to the company. And what that allows us to do is take a cohort of people, say 100 people, and help them, or help build a community that helps them, rather, find the right outcome. Now the right outcome might be selling the company, but it might also be shutting down the work they've done so far and joining someone else's company, it might also be getting another job, it might also be being an angel investor, starting a not-for-profit; all of those things are deeply aligned with our interests. As opposed to, you know: one of the problems I have with venture is often, as you said, if you're not going to be the big swing outcome, then there is an obligation to serve LP interests, sometimes ahead of—not always—sometimes ahead of, or at least alongside the company and the founder interest. 

David Booth  54:47

Now, that doesn't always work out for us either. But the way it has shown up in early days was we had a couple of founders coming through working on not-for-profit projects. And that was great; you know, huge contributors of community. In more recent times, to your point about the trends in the 2023 market, we did in the most recent cohort kickoff, as a sort of an activity when we're all together, you know, "go and stand in that corner if you plan on raising capital; go and stand on that corner, if you plan on bootstrapping." And it was incredible to see: there's almost a 50-50 split. So the number of people not planning on raising external capital was high. More common among repeat founders, people who have perhaps some of their own capital to start with, maybe they come from a position of privilege, others coming from a position of, well, I don't need to raise as much anymore because I've got AI at my disposal, I've got smaller, more highly leveraged teams, I've got, you know, a faster route to revenue coming in. And you're right: my quick take is that the need for very early stage "get off the couch" capital increases, because most people don't have the ability to sustain themselves for three to 12 months, while they get that initial product-market fit; I think that the need for huge amounts of growth capital for a small number of frontier businesses increases; more companies that need to load up on GPUs, or do innovation in atoms, building things in the real world; but that is a decreasing segment of the total number of companies started. But there'll be this huge increasing segment of companies that might need that initial capital, but don't need anything beyond that. And I'm really, really curious to see how the market evolves to respond to that, whether it's a new form of financing, whether it's a new set of institutions and credentials that come along with it.

Gena Gorlin  56:49

It sounds like, to wrap us up, what I hear you both saying to your question, Alice, of like, what advice should we be giving to people? Sounds like you're saying, "We should be advising and pushing and inspiring people to think entrepreneurially about whether and what kind of entrepreneur they want to be. And that may look very different. In fact, there may be a whole different model emerging that isn't already the status quo, you know, within the startup ecosystem, but that might be the next big thing. So, think entrepreneurially, think from first principles, about "is this the model for me, given what I want and what I can bring."

Alice Bentinck  57:34

Thank you for joining us on this episode of the founders mindset. Make sure to subscribe, or follow us to be the first to get every new episode. And if you enjoyed the show, why don't leave us a rating and review to help us to reach even more people would hugely appreciate it. As always, you can find out more about Entrepreneur First by heading to joinef.com. And you'll get more of genius thoughts on founder psychology at builders.genagorlin.com. I've been Alice Bentinck.

Gena Gorlin 57:58

And I'm Gena Gorlin. See you next time!