“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
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!