“There’s hidden treasure all over the world”

The uncompromised ambition of Jesse Genet, serial founder and full-time mom

Welcome to this latest installment of “Fantastic Builders and Where to Find Them.” Originally I planned to make this a double-feature: having serendipitously booked two conversations in one day with ambitious women in the tech scene who’d both decided to be full-time homemakers during this period of their lives, I figured their stories would complement each other nicely. What I didn’t bargain for (foolishly, in retrospect) was just how densely action-packed and idiosyncratically impressive each of their stories would turn out to be. So I’m devoting a separate installment to each of them, this being the first. Stay tuned for my spotlight of Nicole Ruiz to follow in 2 weeks.

Builder Spotlight: Jesse Genet

Photo credit: https://x.com/jessegenet/photo

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 extopic 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 I spoke to her 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.

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.