#9: David Sax, Author

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number 9, and today we have a little bit of a different format. I'm talking to David Sachs. He is the author of The Soul of an Entrepreneur: Work and Life Beyond the Startup Myth. So today we're talking about the startup myth. And the startup myth is that every startup is gonna be a billion-dollar exit, that you're a failure if you don't become a celebrity founder, celebrity CEO. And the truth is the vast majority of entrepreneurship is really not like that. David talked to entrepreneurs from a wide spectrum of businesses like restaurants and factories and beauty salons, about their personal journeys and why they became entrepreneurs and decided to live that life. We talk about their highs and lows, and David and I also talk about the highs and lows of what it's like to be a solopreneur, which David and I both are. We have a really rich, fascinating discussion. So please enjoy my conversation with David Sacks. David, welcome to the show. I am so excited that you're here with me today, and I'm so excited to dig in a little bit about the journey, the startup to growing up journey of the folks that you profiled in your book, The Soul of an Entrepreneur, as well as your own personal journey. So I want to just dive in. I want to ask you immediately, your book is called The Soul of an Entrepreneur and the subtitle is Work and Life Beyond the Startup Myth. So David, what's the startup myth and why do we need to go beyond it?

Great question. And thanks for having me on as one of the early guests of this podcast. Please remember me when it's, you know, broadcast on some massive satellite network.

Absolutely.

Um, Alisa, The Startup Myth, I think, is something that we all know and, and have, and have sort of felt and absorbed over the past decade or so, which is the idea that entrepreneurship is a game. Um, and in that game, you know, you're young and you're brilliant and you go to one of three Ivy League schools and you have an idea and you ask some people for money and you get couple million bucks thrown at you, and you do, you know, your successive rounds of financing, and then you IPO and you're a billionaire, and then you go to space.

Basically, that's how it ends.

You go to space. Everybody goes to space. Which is, you know, true if you're Elon Musk or, um, you know, one of a handful of—

Jeff Bezos.

Yeah, celebrity founders, um, in that get profiled in these sort of world of, of the startup mythology. But the vast majority of entrepreneurship, even in the world of high-tech or, you know, direct-to-consumer goods, isn't reflected in that. And that's the reality of what being an entrepreneur is— the emotional, personal journey that someone takes when they go out and work for themselves, whether they're starting a multi-million, multi-billion dollar company, or whether they're taking over their family's auto repair shop or, uh, going out to work on their own as a, an executive coach or career coach. My wife does the same thing you do actually and started business, um, 4 years ago. And, and so, you know, that transformation and that experience of being an entrepreneur, of working for yourself, of being your own boss, of sort of charting your own destiny and, and having the responsibility that goes with it is what I was interested in. And that was never reflected in The Startup Myth. It was there in the sort of cute origin stories that were, you know, massaged by PR people, um, in, in the, the intros of, of, you know, the, the, the high-profile talk. But, um, you know, that, that real deep reality and the struggle that entrepreneurs have with every aspect of that journey— success, failure, everything in between— that, that's actually what defines entrepreneurs.

I definitely want to dig into that transformational journey and sort of the growth path, obviously, but I also want to go back to your origin story. You're a business journalist and you wrote a groundbreaking book called Save the Deli. We all thank you for that wonderful—

Bread. More of a bread-breaking book, to be honest.

Yeah. That's absolutely right. So you said you were interested in the story and I'm curious, how did you personally get interested in writing about entrepreneurship and the journeys that you're talking about?

Yeah. Well, it was two things, right? One was, I have always written about entrepreneurs and always been interested in entrepreneurs. So, you know, I guess I became a business journalist, but I started out as a freelance correspondent in South America and then wrote about, you know, business for Businessweek and wrote two books about food, one about Jewish delis where I was basically just talking to Jewish deli owners and entrepreneurs all over the world, and then another one about food trends and people who were everything from farmers to,, you know, mushroom kit, um, startup, uh, people to, you know, cupcake shop owners. Um, so I've always been drawn to entrepreneurs. I never wanted to write about public companies, capital markets, large corporations. I was always just shuttled to some PR person. I like that personal journey and the personal relationship people had with work. And so I've always— all my books, all the articles I wrote were always focused on entrepreneurs generally. Um, but the other part was the personal side, which is that I have always worked for myself. The last job I had as a ski instructor when I was 20 years old. I started out on my own and I've remained on my own. People are like, oh, you got to adjust to working from home. It's like, guys, I've been doing this. I've been working in my shorts forever. And everyone in my family does that. My dad has always worked for himself. My mom had her own business selling clothes. My mother-in-law had a business where she sold various tchotchkes out of a van around Toronto, you know, macramé plant hangers from Mexico, rattan furniture from the Philippines. Various, you know, crappy garments made in China, um, and still does it out of like a folding card table whenever she gets the, the feel of it. Um, my wife, as I mentioned, started her own business 4 years ago after, um, coming off maternity leave with our son, left executive recruiting and started her own career coaching practice. Um, my brother is literally like on the other side of this house on a call with an aerospace company because he's starting a space mining operation or moon mining operation.

You did not hear that very often.

Yeah. No, it's not, not a very common thing to do. And also has, you know, had a bunch of other businesses that he's worked on. So it's, it's, you know, entrepreneurs have surrounded me my whole life. It's been sort of a defining thing. And yet I never saw that narrative and that truth reflected in the hype and the press and the mythology around startups that's really emerged over the past 15, 20 years. Right? Yeah, the post-Zuckerberg Twitter, you know, mobile internet era where every day brings the fresh New York Times, Forbes magazine, you know, Fast Company profile of the young beautiful founder of something that just got X round of capital. Um, I didn't recognize the people that I interviewed and the entrepreneurs that I knew, and that represented, you know, the vast majority of entrepreneurship. I mean, it was, you know, we focused on sort of the very tip of the iceberg, but 99% of entrepreneurship isn't that. It isn't seed rounds and funding rounds and venture capital and exits. It's the stuff that most of us recognize from our family members and our neighbors and the businesses that, you know, make up 50% of the economy.

And it sounds like you just were curious and really wanted to give those people exposure, kind of the real entrepreneurs. Kind of exposure, and you were just personally drawn to that from your personal history.

Yes, and also to sort of get behind it, right? Because we've now, you know, there's never been more interest in entrepreneurship. So this is one of the interesting things I found was, you know, early on in sort of writing about this book, long before I even wrote the book, I was thinking about the idea and I was in New York with my friend Greg Kaplan, who's a brilliant Australian economics professor at the time Princeton, University of Chicago lately. Um, and I was thinking, I want to write a book about this golden age of startups and the golden age of entrepreneurship. It's never been easier to start a business. There's never been more young people doing it. Look at all these millennials. And he turned to me over bagels and lox, and he's like, well, is it? And I was like, yeah, of course. Look at all the ads for the WeWorks and, you know, all the startup hustle things. And, you know, this is the time. He's like, well, you should check the figures. And so he sent me the numbers from, you know, the Department of Labor Statistics, Bureau of Labor Statistics. It's like Actually, we're living in the least entrepreneurial time. You know, statistically speaking, more people started businesses the year I was born in 1979 than, than now. It's been steadily declining since then. So while there's a very small percentage of very visible, you know, businesses that are being started in one sector or small number of sectors overall in the economy, and this is across the sort of Western wealthy world, the number of startups, the number of people going to work for themselves has been declining. Fairly steadily. And so there was this disconnect between the myth and the reality, and I think that opened up this question of this bigger picture, but what the sort of deeper meaning of entrepreneurship is beyond that mythology. And that's what the book really explores.

Yeah, well, I, I totally got that because, you know, again, I mentioned that personal journey from founder to CEO, and, you know, you can talk about that with Mark Zuckerberg and Jeff Bezos and kind of the, the New York Times splashy pages, but we can also talk about from folks from your book. You talked about Kevin Mauger, M-A-U-G-E-R, from NCC. And he seemed to me to be like an accidental entrepreneur. And you talked to him about his kind of growth. What did you find out about his growth as he began to understand what leadership was about?

Yeah, yeah. Accidental entrepreneur is a great, great way to put it. And I think there are many entrepreneurs who who fall into it or just happen into it, you know. Oh well, I had this thing and I don't know, one day someone offered me this, you know, opportunity and I guess I just kind of got into it and here I am 30 years later. And Kevin was like that. He, you know, he, he got his high school sweetheart or college sweetheart pregnant basically and had a baby freshman year, um, in, in Pennsylvania. And that summer was, you know, passing out flyers to like cut lawns and do whatever he could in in Pennsylvania, just, you know, about an hour or so north of Philadelphia. And this guy said, oh yeah, you can come to my thing and, you know, you know, come work with me, come, come check me out when you graduate college. So he graduates college and he goes, knocks on the guy's door and he said, you want a job? And he had this company called NCC Systems and it's basically— they make automated conveyor systems, you know, Rube Goldberg machines that go into every type of factory, every type of warehouse that move a product from here to there, whether it's, you know, KitKat bars or boxes or eyeglasses. I mean, it's— they build that whole system. Not just— he says not conveyor belts, conveyor systems. That's just the rubber thing. Um, and he worked there for, uh, I think, you know, 15, 20 years. And the company got bought out, it got sold, you know, the owner died, it got sold to a competitor, it was going in the tank. And he's like, what am I doing? This company is going to go down. All these people work for it. I got my family. Maybe I should take a risk. And just saw an opportunity, you know, mortgaged his house, got some money, bought the company up from sort of the ground because it was going under. And he's like, I guess I'm the owner now. I guess I'm an entrepreneur. He never had this intention of becoming it. Right. And then it really took him years to actually realize, well, what did it mean to be an owner beyond the financial responsibility of you own this thing? You're responsible for the employees, you're responsible for yourself, you're responsible for the financial performance. What he realized was actually his— what he had to assume a role of leadership. And he's a very quiet, soft-spoken guy, not the one to stand out front, never the one to sort of do an event. Very, you know, our conversations were very measured in how he talks. And it took him years to actually realize that being an entrepreneur also means you have to be a leader. To the individuals around you. You have to actually have values, and those values that you have, your own personal values, have to actually shape the business that you have and how you run it, right? And so what this ended up being is him realizing that, you know, leadership meant that ownership took on these responsibilities, and he eventually sold the company to his employees through an employee ownership and ESOP, uh, because he saw that that was the way for him to transfer that legacy and, and, and make the company not only more sustainable in the future but give back to those who allowed him to, to do so well. Um, and again, it's that, that inner journey and the inner realization of the entrepreneur that allows for that.

Yeah.

Um, uh, but is never this sort of clean thing like, oh yeah, and our values are this, this, this, you know, integrity, leadership, and whatever, and we stamped it on the thing and Yeah.

Well, actually, I think most people think of values as, okay, integrity and do the right thing and help each other, and they stamp it on the wall. And then people walk around and they do not that. And not only that, but you sort of have this one discussion about leadership and values with your team or even just with your inner circle or with your founder and co-founder. And then they're like, okay, good. Done that. Did that. Put it on the wall. And then they don't hire for that or talk about that or even necessarily act that way. So it's this disconnect. To me, it's even worse. It's this disconnect between what we say we stand for and what we actually stand for.

Right. And that was the thing about Kevin. I mean, this was the hardest part of the book to find sort of a subject for. I wanted someone— I didn't want some company in Boulder, Colorado making t-shirts out of recycled bottles. And they're like, our values are these, like, environmental stewardship. We make a t-shirt and for every t-shirt we give another t-shirt to a child in Africa. Just Africa. It's a place. We don't know where in Africa. Just, we just throw them, we just throw them over there.

Yeah, like hippie entrepreneurship.

Yeah, exactly. Uh, and, and, you know, Kevin was like, he's like your average American swing state, swing county voter, you know, middle-aged white male, like Norman Rockwell-esque kind of figure. And him wrestling with those values, you know, I think when, when you learn about an entrepreneur's values is when push comes to shove. And there actually is this question of sacrifice, right?

Mm-hmm.

And so he had the opportunity to sell his company for $20 million.

Mm-hmm.

To a private equity firm or a competitor. And he turned it down multiple times because he knew that it would mean layoffs, it would mean demoralization, it would mean that all that he built up around his values would be sacrificed. And so he sold it for half that price when he sold it to his employees.

Mm-hmm.

But that was the sacrifice he was willing to make, and that was the cost to preserve his values. And I think that's, that's that sort of deeper truth about the entrepreneur. When you go from the sort of founder, you're like, I just want this thing to be successful, to, okay, well, now I have this choice. You know, these people are offering me this money, um, or I, I'm offered this contract by the Saudi government or something like that, right? You know, we said we would do no evil, but no, but everyone has a price. Who doesn't survey You know, who doesn't? You know, it's— what's a little money laundering, right? Um, uh, and I think that's interesting because it's, you know, an employee rarely ever has that opportunity to use— to, to really steer what they're doing through their personal values. They're, they're directed by the personal values of the people who are leading the company.

You're right.

You shall do this, you shall not do that. And every entrepreneur has that ability to decide what they're going to do in every circumstance, big or small.

What do you think it takes? I'm just curious, like, what do you think it takes to be that kind of person who, when push comes to shove, will take that stand in accordance with their values, even though it requires sacrifice? And what else did you see as you were talking entrepreneurs?

Yeah, um, well, I think, you know, first of all, I mean, I get asked all the time, what does it take to be an entrepreneur? And I was like, you know, the willingness to take that risk and go out on your own. And, and I met, you know, over the years of the hundreds of entrepreneurs that I've interviewed, I mean, introverts, extroverts, you know, people come from humble backgrounds, people come from wealthy backgrounds, men, women, people of every race, creed, and background, of every temperament. So I think any— anyone can be an entrepreneur, and pretty much everyone is in terms of the sort of spectrum of society. I think what it takes for for the entrepreneur to sort of live by their values is a certain amount of reflection and confidence in who they are and what actually being an entrepreneur means to them. I think one of the dangers of The Startup Myth is that it conflated entrepreneurship and entrepreneurial success with metrics that are derived by the model of venture capital funds and the needs of those venture capital funds to make a certain type of return in a certain time period, right?

Yeah.

This is a financial model of a financial product, essentially, the venture capital fund. Um, you can buy, you know, invest in it if you're a pension fund or a very wealthy individual or whatever. Um, and it's based upon this, you know, we invest in this many companies, we invest this much money, and over this many years we're expecting a, you know, 10 to 30% return based on, you know, X number of averages. And that requires us to invest this much money in this and these different rounds, and this one's going to go in this way. And, you know, and that requires certain things. There's a rule book. If you get this much money, you must deliver this much return. If you get offered this much, we have to sell you at this rate to a competitor or the public markets. And so that, that doesn't leave a lot of flexibility for the entrepreneur themselves. Who created this company to, to do things in a different way or work at a different pace or own their company forever and, and, you know, raise their kids to take it over or sell it to their employees or something like that. Um, and because we put so much of an emphasis on the success— this as a metric of entrepreneurial success— there's an entire generation of founders that are going into business seeing this as the only path to success. And they cannot deviate from that path. And if they don't reach that high bar of success, which is a very rare thing, it's like an actor starting out and saying, "I'm going to be an Oscar-winning A-list star." It's not going to happen for the majority of people. Or someone picking up a basketball and saying, "I'm going to play in the NBA," right?

Yeah.

Vast majority won't happen, but you could still be a good basketball player. You can still go to college and do basketball. You can be a basketball coach at a high school. You could work at a community center. You could open a store that sells basketball goods. You can work for a shoe company. You can design basketball clothes. There's a million different ways to do it, and not all of those equal sort of a $100 million contract with the Knicks or whatever. Yeah. Entrepreneurship's the same thing. Why are you doing it? Why did you start this company, right? Did you go into it to make a billion dollars? There's other ways to make a billion dollars. Most entrepreneurs do it for all sorts of different reasons, because of intellectual curiosity, because of a personal journey or, um, something that they had when they were working somewhere else and they couldn't do— they— for a quest for freedom, for a quest for independence. Maybe they want more time to spend with their family, and it's not about making more money, it's just about having a better life that they have the control over.

Yeah.

And that informs their values. That's the sort of core of what being an entrepreneur is. But we don't talk about that. We don't celebrate that in the same way as like, you know, they went to Stanford and they raised, you know, $50 million on their first fund, and now their Series B is going to be, you know, it's valued at this much money. Like, that's these checkboxes that don't really have anything to do with people's values, um, or that deeper journey about why they're doing it, right?

You've said so many things. I mean, especially, it almost— sorry, the, um— no, it's good, it's just so rich. I especially appreciate that you'd say, and I would say this is true of all the founders that I work with, there's something in them that does not want to work for someone else and they want some sort of personal freedom.

Absolutely.

And what's interesting to me is that no matter what, again, the founders I work with tend to be venture-backed startups. And so, they are definitely on that growth journey, call it the growth orthodoxy. And so, in some ways, it's an entrepreneurial trap. Because you want the freedom, but you sort of shackle yourself to this need for growth and the addiction for growth in some ways. Yeah.

And when you sign— when you accept that check from a big investor who takes a chunk of your equity, you are working for them. Yeah. You are in some way employed by them. And, you know, this goes back to the definition of an entrepreneur. I mean, the word comes from the— from France in the sort of 17th century. There's an early 18th century economist, Richard Cantillon, basically wrote a book about economics, one of the first books about popular economics ever written. He has this essay about entrepreneurs in it. He said, "There are two types of people in this world, those who work for fixed wages, those who are employed by someone, and the rest are entrepreneurs, whether they're the farmer in the field or the beggar in the street or the wealthy merchant who's sending his ships across oceans and trading." And the thing that unites them all is the fact that they work for themselves and they bear the risk of that. They bear the risk in the hope of some greater reward. That risk may be different, the reward is different, but that unifying experience is this desire to be in charge of their own destiny. Um, and I think that's something that people tend to lose sight of as a value. Or as a benefit of. I mean, that's also the weight of it. That's the crushing of the shoulders.

Well, as you mentioned crushing weight, I'm going to shift gears a little bit. And because in your book you also talk about a therapist and the therapist says, "Every gift we have has a corresponding weakness, but you can get lost in the gift. For entrepreneurs, they lose themselves in the jobs that they do." And I was just curious, like that's kind of, in some ways we have this sense of entrepreneurs, they want the freedom. Also, entrepreneurs I know work very hard and identify very closely with that business. Do you think that's just an occupational hazard of being an entrepreneur, or is that a drive that makes you become an entrepreneur?

I think it's a bit of both, but I think it's something that people who become entrepreneurs underestimate before they do. Yeah. When we talk about losing yourself in it, what we're really talking about is sort of identity in the sense of self, right? You, Alisa, are a podcaster now and an executive coach, but you're an individual. You're Alisa Cohn of New York— New York, right? New York City. Um, uh, you know, you live here, you grew up there, wherever you grew up, right? You have your friends, you have your likes, you have your things. So regardless of how your business does, you remain Alisa Cohn. But when you work for yourself whether you're a sort of solo entrepreneur like yourself, which I do, created a company.

Yeah.

Um, your sense of identity becomes much more intricately tied to that business and, and the sort of ups and downs of that business. And you can't separate it as easily as, oh well, that was a crappy day at work. Susan in accounting, honestly, I don't know, maybe I should go find another job. Right, right, right. You know, oh God, that place, that business is bad. But now at least I have my, you know, weekend of, you know, golf or whatever, skiing or whatever I do that's like separate from work, right? Psychologically, it's very difficult for the entrepreneur to separate the work from the sense of self in good times, in bad times, and everything in between, because they— so much of their self-worth is tied up in their identity as an entrepreneur.

Yeah, yeah. I feel that way. Of course. I totally feel that way, right? Because I'm identified very much with my career and also as being a solopreneur. And also it is my living, it is the living I make. And it's also my mission in the world is to serve entrepreneurs and to help them on their journeys and to help them with that sort of psychological transformation. And on a bad day, I'm like, oh, I can't do it. And on a good day, it's like very euphoric. And so I—

and you often the same day you're talking, you know, it's like, someone didn't return my call, I'm garbage, I'm garbage, you know, I should never have done this, right?

Right.

They return your call and you're like, I'm the greatest, I'm treating myself to lunch.

Well, that is definitely the life of a solopreneur, that's for sure. You find that, I guess, right? It's all about lunch. It's all about lunch. Someone taking you to lunch or yourself treating yourself.

This is what I missed from the pandemic. Just lunch. I just want lunch. Totally.

But David, I'm curious, how do you feel? So you're also a sort of quote unquote solopreneur.

Sure.

You're an author, you're a writer, and so you're also self-motivated and self-determined and no one's telling you what to do. You're telling yourself what to do. So what's that journey like for you and how have you found it, your own sort of transformation as you've grown as an entrepreneur?

Um, it's exhausting and wonderful. I mean, I think it's, you know, a big reason for writing this book was just coming to terms with all this and coming to terms with what I experience all the time and writing a book. I mean, I, I— interesting, I met someone the other week and she was— she had recently gone freelance in the film industry. We were speaking, she's like, well, what's it like? You know, you've been freelance. I was like, yeah, I've been freelance for, you know, near 20 years. Um, she's like, well, what's that like? When do you get used to like that ebb and flow and not getting the work? I was like, honestly, never. But probably after 10 years, you know, you'll at least like have some defensive mechanism to know that you're not just gonna starve and, and that opportunity will come, right? Um, and I think for me it's, it's the same thing. It's that, you know, knowing that that this is a long-term thing.

Mm-hmm.

And coming to terms again with the reasons for doing it and what matters to me. And I think, you know, maybe when I wrote my first book, I was like, well, this is it, and I've done this book. And now once the book's a number one bestseller, then— and then it didn't become a number one bestseller. It sold well and it continues to sell, and it got me known. Every, you know, Jewish person North America knows, you know, when are you writing another book about delis? But, uh, David literally saw my mother-in-law's— someone, friend, like, asked me that the other day. What are you working on, another book about sandwiches? What about the ones you didn't talk about? What about a bagel book? Um, but it's coming to terms with, you know, now looking back at 20 years of a career and seeing like, okay, I, I do well for myself, but I'm no You know, I'm not Malcolm Gladwell. I'm not selling millions and millions of copies. But, you know, I, I, I, I got to travel the world when that was possible. I got paid to speak at all these places, which has been a wonderful sort of blessing. And most importantly, I now have the freedom, both financially in terms of time, to do what I want. If I want to write a book about, I don't know, camping, which was some dumb idea I had last year, you know, in 2 years when I have time to do it after I'm done working on the current book, like, if I could sell that, I can do it and I can go camping and spend a year doing that. I have the freedom to do that. That's a benefit that, that actually, you know, I got to financially factor in. And I know that that will have those ups and downs, but the— what I've realized is the freedom, which is the thing that got me into it in the first place, is the thing that I value the most. Um, But on the day-to-day, those ups and downs of highs of expectations and lows of disappointments, I mean, it still is a struggle. And I think it's always a struggle. I think that there's very few people for whom it isn't. They'd be disingenuous to say that, "Oh yeah, I'm used to that." No one gets used to it.

Yeah, totally. It's very hard to get used to. You shouldn't. But I'm curious, what tools and practices and rituals do you use? To remind yourself you're going to be okay during the downs? The ups are probably okay, but the downs?

That's a great question. I mean, I think the most important one, I don't know if she's a tool or a practice, would be my wife.

Interesting.

Which is a greater reflection of support and community, right? I think that community, whether it's the individuals in your family or a circle of friends or maybe an entrepreneurial support network, whether it's your local Rotary Club or a group of founders that you meet with regularly or a mentor or whatever, having individuals to talk with about these things is really important because it actually helps put things into perspective. When you get so inside your head and your identity, like, "This is, I don't know what to do and this is destroying me," it's like, "Hey, look, let's put this into perspective." positive, right? Yeah, this is what you do. Here's why you're doing it. Let's put this into the long scale of things. This one little event that you're so obsessed with right now is not going to define you and is not in any way, you know, destroying your, your entire life, or is not the biggest sort of thing. I think having that support, especially within family and friends, keeps the entrepreneur from being so isolated., and allows you to keep perspective on what you're doing and, you know, having a, a greater sense of a balance. And then I think, you know, trying to separate out— you know, there's this symptom of the sort of startup myth, and it's this hustle porn. I work harder than anyone. I don't take vacations. I don't take breaks. I don't take whatever. Um, I do. You know, I got really into like surfing, lake surfing this year, and, um, I, I'm, I'm, you know, okay with separating that out, knowing that the job is going to get done, knowing that I'm doing my work and doing my things, but, um, being able to sort of say, okay, I'm gonna put my phone away, I'm turning it off, I'm putting my computer down, I don't, I don't have to be working 24/7 in order to define myself as this, um, and that space has helpful because then you come back to it and you're more excited and you have fresh ideas. Um, uh, and I think having that balance, having things in your life other than work, is incredibly important. Yeah.

Did you, when you were first starting, let's say even like 10 years ago, were you the kind of person who could take—

10 years ago, it's very generous.

Thank you. Well, I know you were starting 20 years ago, but let's, you know, someplace along the journey Did you decide, okay, I gotta take breaks, I gotta take— or was it like, no, I've always been that way? Or was it something you had to learn and grow into yourself?

I think a little of both, um, but I think I learned to stop sort of stressing it. Like, if I was, you know, if I was waiting for something and I'd sent out a bunch of pitches, um, to publications or whatever when I was starting out, like, oh, I, you know, it's Friday but I don't have any work, but like, I should send out 20 more pitches or whatever. It's It's okay to take the afternoon off and go for a walk or go do something. That guilt is consuming. It doesn't mean that I'm sitting around all day watching TV and eating Cheetos, but you can have that balance. And because you have that freedom, you're allowed it. You don't have to work 9 to 5, 5 days a week or whatever because your colleagues are, because they're getting paid for that. They're being paid to have their butt in that seat. You're not. So take advantage of that. And that might actually open up, you know, these better ideas and these other things that come into your head. I mean, sometimes an entrepreneur needs that space to think. They need that space to come up with ideas. And that's a luxury that they have. No one's paying you for your time.

Yeah, totally. So actually you're earning your rewards like that. Again, the point about entrepreneurship is freedom and the time to structure your own time and to have the time for creativity.

Right. And if you take that value, yeah, if you value it, you know, yeah, then you should take advantage of that.

Yeah, yeah, that's lovely. Did you talk at all to the founders and entrepreneurs that you interviewed about their own issues with anxiety and depression? Because founders are 30% more likely than their counterparts to experience some sort of depression or anxiety. Did you discuss that with folks?

Yeah, quite a few of them. Um, you know, some, some really had struggled with it, um, very deeply. Uh, some had no issue with it, they had a, they had a good balance. Um, but I think they were all— any entrepreneur is, is willing to talk with you honestly about what they're going through. I think that's the thing, is there is, there is a lot of vulnerability there, and there has to be, right? When you put yourself out there, so to speak, into the world as someone who is doing business for themselves, you are immediately vulnerable financially, but certainly emotionally.

Yeah.

And, and because your identity is so tied up in it, you know, that vulnerability can take a tremendous toll, um, if left unchecked.

Yeah. Is there a story that you recall from one of the founders or entrepreneurs that you talked to?

Yeah, well, I, I, you know, this, this great farmer rancher in in the Central Valley of California. So about 2 hours east of, southeast of Silicon Valley, Seth Nitschke. And you know, Seth is a guy, grew up kind of around ranches and cattle and worked at big companies, Cargill processing facilities, you know, counting cattle and, and, and really got into the idea of grass-fed beef for health and for the environment and, and started his own ranch, ranching company with his wife. And, you know, I talked to him 10 years in or 13 years in and, you know, Mariposa Ranch was kind of stuck. You know, they were making money, but not that much. They'd just been denied a mortgage to buy a ranch and it was pretty crushing, like weeks before, you know, it was having tension on his marriage. And he was at that point of, you know, saying, well, you know, what am I doing? Like, I'm working my butt off. You know, he didn't own his own land, so he had to basically like like, like, imagine a carpool with cattle. You know, like, there's 4 ranches spread around a 100-square-mile area. And it's like, all right, Monday, I gotta take like these 20 cows, pack them into the trailer, drive them to the southern ranch so they can graze here, like, crazy and exhausting. And the amount of money spending on gas is eating into the profits tremendously. And it's just like, what, what, you know, I caught him in the center, like, like, what am I doing, face? And I talked about, you know, what did that lead to? How did he deal with it, right? What was that like? And he said it was, you know, part of it was like, he said, you know, when I talked about losing the mortgage or getting denied the mortgage to buy the ranch, which would have given them the land and consolidated everything in one place and the family could have lived there, he said it was like, have you ever been kicked in the nuts by a horse? Like, that's what it was like. And then the horse trampling on top of you. Yeah, he was very evocative, very great, but very thoughtful, funny, caustic kind of guy. Uh, we still talk to this day, and you know, he worked through that, right? They're still going, him and his wife. You know, she's back in the business now, and they're working well together, and the kids are there. And it's— it's— it required that working on— working on the business, but also working on himself and that sense of self and the sense of vulnerability and knowing when to ask for help and and knowing, you know, what's important and what's not. And I think again, you know, every entrepreneur goes through that at some stage, but the idea that it's either this, you know, instant hockey stick rise. I mean, one of the most, you know, interesting people I talked to was this gentleman, Bart Lerang, who was a founder of a very successful startup in Colorado. Its name I can't remember. Uh, and you know, he was in the worst possible spot. I said, what's the word? The hardest time you've been an entrepreneur? He said, now. He's like, I'm not sleeping. I'm having— I got shingles from the stress. My wife, you know, and I are seeing a therapist because things are really bad. Uh, and I said, well, why is this? Like, well, we're, you know, we just got valued at a quarter of a billion dollars, and, um, and I'm under all this pressure to get the valuation up to a billion, but then I'll be able to rest. "Then it'll be good once I get to that billion-dollar thing." And I think that's the fallacy and that's the danger of that startup myth.

Yes. Well, actually, the therapist you talk to in the book also says that he talks about entrepreneurship as an addiction. And one of the folks you profiled calls himself bipolar. And I'm just curious, do you think that entrepreneurship is a mental illness?

No, I don't. Um, uh, I, you know, a mental illness is a, um, yeah, that's, you know, is a separate thing. Uh, but I do think that entrepreneurship is appealing or attractive or a fit for all sorts of people who have perhaps, you know, personalities that quite different from sort of the standard mean. Um, uh, and, and because it allows people that independence and that flexibility for their own ideas and their own way of thinking. You know, I think of some of my friends and family members who are entrepreneurs in there. You know, they were, they were never the best students. They were always the one who had trouble paying attention or on like ADHD medication.

Yeah.

And it's just like, wait, I have this idea, I have this idea. I mean, that doesn't fit so well into a box of a corporation. Yeah, you want to work for a corporation, you want to make a lot of money, you want to go up the ranks, like, you're, you're a good little soldier, right? Is as open-minded and is, you know, kale salad bar, um, flexible work hour, you know, sneaker thing is like Amazon or Google or, you know, JP Morgan maybe. Like, you're like some, you know, Korean 25-year-old in Samsung. Like, you, this is what you wear, here's where you are, do your work, right? And you'll be rewarded with money, right? Um, and most entrepreneurs I know are like, I didn't want to do that. It was interesting. I read this book as part of research. It was called Entrepreneurial Man, I think. Um, maybe it was that. I, I forget. It was one of the first sort of American studies of entrepreneurship written in the 1950s. Okay. Out in the Detroit area. And it was all about entrepreneurs, different entrepreneurs. It was just interviewing like, who are they? What is it like to be an entrepreneur? And I remember this one guy You know, it's all— it's sort of like a sociological oral thing. And they were talking about— they're like, well, Fred H., who owns a car parts business in Dearborn, is like, I don't want to work for these bums. I got sick of working for these bums. You know, these bums are going to work for me now.

And it's just—

it was so beautifully typical of this idea of like, I wasn't valued. I, I'm going to be in charge of this destiny now.

Yeah.

And that takes a certain personality. But it's not exclusive, right? As I said, there are quiet, very introverted entrepreneurs that I know. There are loud, bombastic entrepreneurs that I know. There are the kindest, most community-minded entrepreneurs that I've met. And they're, you know, fine Rand-loving libertarian psychopaths, um, and everything in between. And that's what makes it beautiful and wonderful, because it does capture that spectrum of humanity through business, I guess, right?

Yeah, I totally hear that. You know, David, as you were writing, you're talking to these people, and then you were talking to other people around, you know, these founders and these entrepreneurs, and then you wrote the book. And I'm just curious, that was, that was a, that was an investment of your time and energy. How did that book, how did working on the book, writing the book, change you?

I, I think it, what it really did was sort of You know, the one of that reasons I said that I did it was to really understand more about why I work for myself and really understand, you know, this fascination I've had with entrepreneurs, like what lies behind it? What does it actually mean to be an entrepreneur and to work for yourself? And I think it changed me in the sense that I have that better idea about it. And I can put myself into that broader context. I mean, one of the things, you know, my brother, entrepreneur and whatever, like last night he's like, space entrepreneur, space entrepreneur now, cannabis previously, and, and real estate and other stuff, right? Um, you know, he's, you know, he's like, he listens to books about entrepreneurs, like he's in, he's into that. And, and he's like, you know, I heard that, um, Ben Mezrich or whatever, the guy wrote The Social Network and Bitcoin Billionaires, you know, brilliant business journalist, he's like, you know, he wrote a book in 6 months about the Robinhood, you know, the trading thing like, why can't you write a book in 6 months? It's like, A, B, um, uh, you know, because I don't want to, because I don't need to, because I decide my own schedule, because that's not what I need. And if I— and I, and I no longer compare myself to, you know, I used to look at like someone, oh, you know, look, look whose book did well, it sold this many million copies, and I would feel bad about myself. But that's not, you know, I can only do what I can do. And am I enjoying what I'm doing? Am I making enough money that I'm content and financially secure? And hopefully my daughter can go to summer camp next year. It's really expensive, I realized. You know, go on vacations and, and, and, you know, live the life that I like. Yes. So I should be content. Like, it's, I think it's that that sense of fulfillment and contentment— fulfillment and contentness. Yeah, fulfillment and contentedness. Um, that, that I've come to appreciate after seeing that, you know, the entrepreneurs that were happiest that I knew were not necessarily the ones that made the most money or were not necessarily ones that had the biggest success. It was the ones that, again, you know, were able to sort of really appreciate what they did and find meaning and joy in that over the course of their lives and their careers. And I came away with a greater sense of that for myself, having to reflect on it.

Yeah, that's very— again, I'm very interested in the transformational journey, so I really appreciate that. I also appreciate that you put yourself into that mindset and you were allowing yourself to be changed and moved and imprinted by this experience.

Yeah, I mean, I think it was, you know, it was the hardest book I've ever written for all sorts of reasons. But one was because of that, because it forced me to sort of really reconcile and be honest and vulnerable with who I am and what I do and why I do that. But at the end of the day, you know, being content with that has been the best reward of it, especially because the book came out right as the pandemic started. Yes. Sold like a pitiful amount of copies, but whatever.

Whatever.

See, it was, you know, in previous books when it was sort of disappointing that way, I was just crushed. And now it's like, okay, at least I can blame it on a pandemic. That's right. I don't know what I'm going to do next time.

Right. Well, what— so what is next time? What are you working on now?

So right now I'm working on a book that is a follow-up to the book that was previous to Soul of an Entrepreneur called The Revenge of Analog, which is the book of mine that's done the best. That came out in 2016. And, uh, that book looked at why we were seeing sort of the renewed growth of non-digital things like vinyl records and independent bookstores, um, you know, wristwatches. And, uh, and I thought a lot about the future. I asked often like, well, what is this show about the future and talks and so on? And so when the pandemic began, even though Soul of an Entrepreneur came out in April of 2020, I was doing more interviews about that book and that subject, the analog one. And it was like, well, what does this say for the future of the office or whatever? And, you know, now that everything's going to go digital, and there was this assumption, and there's been this assumption across the entirety of my life, that the future is going to be digital in name your field, right? You know, work, school, entertainment, sports, uh, relationships, community, cities, so on and so forth. And that future was always this kind of far-off goal that we were all working toward, and then suddenly you know, 17 months ago or whenever. It just dropped into our lap one weekend, and we've had to live through it as I'm talking to you on some, you know, chat app, um, and actually experience what that's like. So we never get the chance to test drive the future. And, and, and so the book asks, you know, not only what were the benefits and, and drawbacks of, of digital and all these different realms of our lives that we experienced over the past year or so. Yeah, but what did it reveal about the value of analog, of the non-digital experiences, relationships, spaces in work, school, community, cities, and so forth. Um, and how do we think about that in the future? And so it's called The Analog Future, um, and it's been interesting and kind of grueling because, you know, every other book I do is just an excuse to go places and meet people and travel and have these interesting deep conversations with someone. You know, the conversations with Seth Nitschke the farmer. I mean, that happened over 3 days at his, you know, in his pickup, at his house for dinner, you know, over tacos on a ranch, sitting on the back of an ATV covered in cow shit. And now it was just, you know, Zoom after Zoom after Zoom with my kids running around in the background. So it was— it actually getting back to that question of entrepreneur, like, why I do is like, I, I very quickly realized I never wanted to write a book like this again because the part that I love is going out and seeing people and meeting the world.

Right, right. Wow. Well, I wish you great luck with that and your process as we're sort of easing out of the pandemic. David, is there anything else you want to share or anything else you want to say?

Uh, no, I, I think that, you know, every founder— I mean, your, your audience, you know, your clientele is typically people who are probably going to be younger and fitting, and male, and fitting into this sort of specific track of entrepreneurship. Um, but that regardless of their ambitions or of their valuation or what they're told, like, they are entrepreneurs, and that is is a broad spectrum with many different paths. The one thing that unites all of them is that they work for themselves, but that's it. There's no— there are no rules, there's no track, there's no defined ladder to success. Um, and so the most important thing an entrepreneur can do at the start of their journey in the startup, or as they progress along, uh, the ups and downs of of their path is, is look inward and, and say, what is— what do I ultimately want? What is the reason I'm doing this? What is the path, right? Do I need to follow this prescribed path, or can I do it in some other way? There are many technology companies, many successful startup software companies that did not take venture capital funding, that do not pursue a very specific path of hockey stick growth. That there are many ways to build a business and live a life as an entrepreneur And each entrepreneur owes it to themselves to be true to that and to actually critically look at what they actually want and desire before hopping on some sort of escalator to riches.

I love that. To riches. I love that, David. Many ways to be an entrepreneur.

That's beautiful.

Yes.

And many flavors of entrepreneurship.

Right. Absolutely. David, thank you so much for being here with me today. I really appreciate it. And I've loved our conversation. Thanks for joining me today.

Thank you, Alisa. Alisa, this was great and I wish you the best of luck with the podcast.

Thank you so much. Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcast so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.