This is an auto-generated transcript of Never Enough Podcast Episode 1. It may contain minor errors.
Andrew: So what's been going on? What have you been doing today?
Sam: I had to record MFM and then I had to do this last thing. Now I'm doing your thing. I'm in Westport, Connecticut, living in a 7,500-square-foot house testing out what it's like.
Andrew: Nice drop of the 7,500 foot. Very good.
Sam: It's a rental, and I got a steal. But I just wanted to see what it would be like to rent a big house. And I lose everything in it. And so I've learned I don't want a big home.
Andrew: Do you want to just give a little bit of background on yourself?
Sam: My 62-second background is that I am from St. Louis, Missouri. I grew up with my mom being a teacher and my father owned a produce business selling fruits and vegetables. I went to college in Nashville, Tennessee. I started my first business, which was a hot dog stand. I realized the internet was awesome and I heard about a company called Air Bed and Breakfast—at the time, that's what it was called. I cold-emailed the founder Joe Gebbia, and I was like, "interview me for a job and here's why you should." And he was like, "do you live in the Bay Area?" I said yes—which I didn't.
Sam: He's like, "all right, great, my office Monday." So I fly out there, go to his office Monday, get a job offer. I leave school and move out there. I lied on my resume because I actually had a DWI and I lied about it. And they did a background check and they caught me. So the day before I was supposed to show up, they said, "you're fired because you're a liar."
Sam: So I was in San Francisco with nothing. I started a roommate matching business, which was like Tinder for roommates—which is stupid, it should have just been Tinder for Tinder. Sold that, only made like 50 grand or something. Started a conference called HustleCon that made like 60 grand in the first 6 weeks. I parlayed that success into The Hustle, which was a newsletter. Everyone at the time laughed at newsletters—now everyone thinks they're awesome. I sold that business for tens of millions of dollars.
Andrew: So when you think about what drives you in this next phase—you did really well, I think you made enough money that if you wanted, you could retire now. How do you think about work?
Sam: I made enough money that I didn't have to work again, but I didn't make enough money to please my ego. That's for sure.
Andrew: You and I have similar anxiety around money, which is for some reason it never feels like enough. Whether that is because we have fears of running out or fears that we're inadequate compared to our peers. I was talking to my therapist and she just stops me and she goes, "Andrew, what would you have to feel if it wasn't for all this?" And it kind of stopped me in my tracks.
Andrew: What would happen if you just stopped for a year or two years?
When I thought about it after my therapist asked me, I went—you know what, it's interesting. When I was in school I was always popular, I was likable, but I was never "the guy." And one of the things I realized about myself is that when I started my companies, I was the guy. Suddenly it's like my own little clubhouse that I've started where I'm important and I'm the dictator and I get to figure out how everything goes. And then the other piece is—when I grew up, I just didn't want my parents to tell me what to do. My parents controlled money with me—it was like "you're in my house, I pay the bills, you're going to do what I say." So it was like, all right, screw you then. I'm going to do what I want, and I got to go acquire capital in order to do what I want.
Andrew: I wanted to ask you—you mentioned that we're both afflicted by this feeling of "never enough." I always looked at it as this very positive thing because it really serves you in business to be generative and start new stuff all the time. But I did have to ask myself—am I distracting myself from something? What is it that actually is driving me?
Sam: So if we go through Maslow's hierarchy of needs—on the bottom is stuff you want. I don't really want stuff, except for a big house where my family could come and they don't annoy me because they have their own space. The next thing is I wanted to be like a time billionaire—I wanted to spend my time how I want. I realized at a young age, life is short. So if I work really hard for a short amount of time—we live in a capitalistic society, it's never going away. The best way to win is to have enough money that you could tell anyone to go screw themselves and spend your time how you want.
Sam: And then if we go higher up that list, it's basically a deep-seated insecurity. Girls didn't want to date me, I felt bullied, I had braces, I was goofy-looking. And then I grow up and I see people like you—you're only a few years older than me. You were fortunate that you found your path. And I carved out a different path, and I'm like, Andrew found this other path that I like more. Now I have to feel like I'm behind him. Now I got to hurry up and catch up.
I don't want to crush your tower. It's like—I want to have a skyscraper just as big, because I want to feel adequate and I want to feel like I belong. I should have a seat at the table. So it basically comes down to a feeling of inadequacy.
Andrew: One of the things I've observed about the most successful people I meet is—when they see someone that they're jealous of, they just go, "okay, well I'm as smart as them. What are the cheat codes? How do I work backwards from whatever they did? And I'll just copy that and learn." And it's not about tearing the other person down.
Sam: The cool thing about capitalism is—a lot of people think that it's a winner-takes-all market. It ain't. I can create value and you can create value. And so I just want to be a serious person and to prove that I've got the chops to do what I think I'm capable of doing.
Andrew: In this next business, you've hired a CEO and now you're delegating the operations to them. What's that been like for you?
Sam: Heavily inspired by you, and it's been awesome. There's been headaches where I'm still trying to figure things out—and I text you all the time where I complain about how do I deal with this situation, am I getting in the weeds too much, am I not in the weeds enough. But basically I'm like the marketing department, because I've got the podcast and my personality. That drives growth. I also am quite good at coming up with interesting ideas that pounce on opportunities. But I've hired a CEO who runs the company on a day-to-day basis.
It's been life-changing. I wish I would have done it sooner. I just didn't have the confidence to do it. And hanging out with you rubbed off on me, and I realized there's many ways to build great companies.
Andrew: My way—like anything else, the grass is always greener. There's lots of downside to doing it this way. But in terms of abstracting away work, it's definitely very elegant. It's not like I work less, by the way. I still have a 9-to-5 job. I'm just not in charge of HR, I don't look at the budget all the time.
Sam: Chris has a saying—"there's no such thing as problems, there's only people problems." So if you can have someone else deal with the people problems, that's a pretty good life.
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