If you have career regrets in 2026, watch this.

If you're crafting your own personal career and you're high agency, AI is like a jetpack. We've taught children, young adults, how to grind. We've taught them to persevere for the sake of perseverance. And if you're stuck, you're stuck.

In order to like do these exercises of finding your passion, you sort of have to be like a ruthless asshole, you think?

Unless you're trying to find that edge, somebody else may be.

You have to understand the difference between risk and uncertainty.

People most at threat by AI are the ones that aren't continuously learning, that are just doing the same thing they did 10 years ago.

How many times when you were doing it did you want to quit?

I don't ever remember wanting to quit.

Really?

Really.

What did the voice say when it was like, I found my calling? I want to talk about the book because there was this— there's a bunch of crazy stats in the book. I want to talk about the Nobel Laureate thing. That was interesting. But the craziest, like, one of the craziest things early in the book, I think Did you run this survey and it said that like 6 or 7 out of 10 people hate their job?

Yeah, so I had a co-writer, co-researcher on the book, and we spent a ton of time together on Zoom calls, and someone encouraged us to dive into a bunch of academic literature. We came across this Gallup poll that said 53% of people aren't engaged at work, and so we had this idea to ask like 1,000 people, if you could start your career over again, would you do it differently? And and 7 out of 10 said yes. And then we, we took that to, to Wharton People Analytics to do the official academic version, so you make sure you get all the statistical data correct. And their number came back 6 out of 10, so still a really big number. And crazy, there's a great book by Daniel Pink called The Power of Regrets, and he has somewhat similar survey data of longitudinal through people's lives. And as you get older your regrets of inaction start to really weigh on you and ruminate in your brain. And a regret of inaction is choosing actively not doing something versus a regret of action is I made a mistake. And humans are really good at allowing themselves to make a mistake, but the path I never traveled, the door I never opened is heavier in their mind. And the survey might have been getting at that, like people thinking, wow, what if I had done something differently?

Well, the reason I was asking is like, I kind of want this whole— like, I'm kind of obsessed with this idea of finding your passion, not just because of your book, but like one of my favorite books is Mastery by Robert Greene.

Yes, I'm familiar with it.

Which changed my life. That changed my life. But the reason I'm interested in it is because like I previously had a company that I sold and it was like very successful in all the traditional measurements. I have a company now that's quite successful and I like what I do. but in the back of my mind, I think that it's normal. And maybe you could tell me if I'm wrong, that like even grownups like who are successful still are like, do I, am I, am I following like the right path? Like, am I following, am I going to be in that 6 out of 10 or the 4 out of 10? Do you find that like even when you were, when you left Compaq and then eventually got into VC, which I imagine that would be your calling, that you still questioned it?

After the engineering degree, I went to Wall Street for 3 years. So I—

you're like in research?

I was a sell-side research analyst. Yeah. So I had 2 stops before I made it to venture. And in both cases, I had a moment of reflection and it's more clear to me now than it was then. But where I ask, do I see myself doing this 30 years from now? And in many businesses, there's a lifer in the room, you know, that's that's done it their whole life. And I don't— that sounds a little judgmental, I don't mean it to be, like, but it gives you a way to reflect on whether that's the, the place you want to be in. Yeah, because they did it. And, and in both cases, after about 2 or 3 years, I got to a no, even though I was doing well in those jobs. But thinking, do I want to be still be doing this 30 years from now, was, was clarifying for me.

But you said something interesting, so like All right, I thought the book was amazing. The best chapter, the, the best part was the early part about finding your passion, and you're like, that's the hardest part. And like you said that, uh, just now, you're like, it didn't seem clear to me then, but it does seem clear to me now that I was questioning that.

Well, I did do that exercise in my brain, and there's another exercise that Bezos is famous for, what he calls the regret minimization framework, where he said, what would my 80-year-old self advise me to do in this situation? Which is another way to get at what I was doing and to get at this, uh, this notion of, you know, you only have one life. Like, are you really thinking about this decision with a reflection of the whole life? And so your 80-year-old self is probably more risk-seeking than you are in that moment because he's trying to minimize that, that regret.

What was the exercise you did then? How old were you?

I would— the, the thing I did is what I already said. I asked myself, do I still want to be doing this 30 years from now? And I did it once when I was an engineer, so I was 23, 24.

But was that voice loud?

I think it was loud. I had no inhibitions whatsoever about walking away. Like, it didn't bother me. And I, I may have benefited in the back of my brain, uh, from the fact that my father went across the country. He, he took a flyer on a job. He got recruited from, uh, Virginia to Houston to be one of the first employees at NASA.

That's cool.

And, and I knew he had done that. And, and so I didn't come from— I think if you come from a family where multiple generations have stayed in the same town, it may feel really wild to just take flyers.

All right. So this episode is all about excellence.

A while back, I shared my personal framework for building excellence in my own life. And the team at HubSpot turned it into a 30-day operating system you can check out right now. It breaks down the systems it took me 10 years to figure out and shows how I actually use them day to day. These are systems that genuinely changed my life. So if you want to build a good life, scan the QR code or click the link in the description. Now let's get back to the show.

When I was 21 years old, I'm from Missouri. I went to school in Nashville, Tennessee. I had a hot dog stand and that's how I paid my way through college. It was called Southern Sam's Wieners, as big as a baby's arm. And we had a bunch of locations at these hot dog stands. It was really fun. And I was like, this is so hard to be out in Tennessee weather, sell hot dogs. It was so hard. And so I Googled like, where do internet companies live? Because I didn't even know because I was obsessed with the internet and it said San Francisco. And I was like, what internet companies are cool? Or like, I don't know what, like what's like the hot thing? Well, at the time it was Uber. At the time it was called UberCab still, and Air Bed and Breakfast.

Yes.

And so I started looking at this thing called Air Bed and Breakfast, and I cold emailed this guy named Brian, the CEO, and he didn't reply to me. But then I found like another employee to email named Justin, and I emailed him and I was like, I'm going to be there on Monday. Can I interview for this company? Obviously, Air Bed and Breakfast was called Airbnb. And they're like, yeah, you live in the Bay Area? And I was like, yeah, I live there, which of course I didn't. I was in college in Tennessee. And so I flew out there the next day, got the interview, got the job, went back to Tennessee, dropped out of college, sold everything I had. But my parents are entrepreneurs in Missouri. They started their entrepreneurial career owning a fruit stand.

Yeah.

And I remember when I told them, I was like, I'm gonna leave school, I'm gonna join this thing. And they're like, what's a startup? And does it have health insurance? I was like, it has health insurance and it's paying like $22 an hour. I think it's gonna be fine. And they're like, okay, cool. We'll come pack up your stuff. And I remember at that moment, like, that emotional support is one of the biggest things that separates what allows people to win versus a lot of people lose. Because I have met so many people. A lot of my friends are immigrants. And like, the immigrant experience is interesting because a lot of the immigrants, it seems like they fall into categories. One category is like, they came here with nothing. So there's— they're willing to do anything to win and they go down one path. And then the other path is, I came here to create a big life. Don't screw this up. Take the safe path.

Right.

And my parents were not the safe path. And that was like the most support that they could have for me. And it was so amazing.

I'm glad. I'm so glad you told that story because even though the person this book is written towards is the person on the career path, and I mean that we don't have a chapter on how to advise people, like it's not written for the advisor, but I think it will be particularly interesting to parents and advisors to test whether or not they're willing to help support people in a way that your parents did.

Well, I think that's a big deal because like, for example, you go to the doctor to get like your basic stuff checked. I go to college, I go to school to get good grades, but at no point do they ask like, are you asked like, are you happy doing this? And I think that that's like, I think that's why I'm still— I don't think I've ever formally— I don't think we've ever formally learned how do you find— I call it ikigai, which I'm sure you're very familiar with. It's this Japanese term where imagine like a Venn diagram, but there's four. It's what the world wants, what the world wants to pay for, what you're good at, and what you're passionate about. The goal is to find something right in the middle, but no one teaches that, right? It's— and so it's interesting. The reason I like your book is because that's what it's about.

And yeah, and in, in the, uh, chapter titled Chase Your Curiosity, I tried to borrow as many of those type of exercises as possible. I even went out I'm surprised I didn't find that one, but I found like 10 others and I put them all in there. Like I'm trying to give people as many of those pathways as possible. Cause I think the very hardest part is to figure out actually what it is that drives you in this way. That's going to make it very easy for you to differentiate yourself. And it's funny, you know, you, you, you mentioned that one. There's a story in the book about this guy, Bert Beveridge in Austin, Texas, who's 40 years old, and he's watching a PBS show, and they say to take a sheet of paper, put it horizontal, draw a line down the middle, write on the left what you love to do and on the right what you're good at, and try and find something in the middle. And through that exercise, he quit being a mortgage broker— he had been a seismologist before that— and launched a vodka company called Tito's, um, at the age— at the age of 40.

I think there's this like famous Mozart quote where someone was like asking Mozart, like, how do I find my way? Or how do I, like, do I have what it takes to be the man? And Mozart was like, dude, if you're asking that question, the answer is no, because, because the conquerors just conquer. And I hated his reply to that because I'm, but I'm curious. So I don't even know all of the companies you've invested in because you've been doing it for so long. You've like, I don't know how many unicorns have you invested in?

I don't know.

Dozens?

Sure.

A lot.

Yeah.

And you've been around all the movers and shakers, whether you invested in or you passed or not, you are somehow like touched all these amazing people. Did they follow a similar path?

For the founders, I think you'd find a lot of different stories and different pathways that got them to where they are. I mean, if you like, the Zuckerberg story is pretty famous. He's at Harvard doing messing around, and that's very different from the path, say, Gates took or even Bezos. So I don't know that there is a pathway to that place. Um, I'll tell you, I, I once asked Jeff Bezos how he could possibly be good at angel investing while he's running this company.

What did, what did he do angel-wise?

Oh, he did, uh, Google, Uber. Like, it's a murderer's road.

He was on the, uh, he was in the seed round of Google?

Yes.

Wow, that's amazing. What was the valuation then?

I think that first round was a 10-poster. But, but to get to the point, he said the only thing he looks for is this insane determinism. He, like, he, he wanted to believe the person was going to go do this no matter what, come hell or high water. And I think that may be a common trait of a lot of the founders. They're just really, really determined, um, and pushing against this thing. The other thing that's true of any tech founder is they're hyper-curious about the edge of what the technology can do. And anytime there's a big disruption— AI being the most recent, but before that There was social media and the mobile wave and the SaaS wave and all these waves, and they create opportunity because incumbents are usually slow to embrace them. And so you can run at these things fast, but that requires you to be hyper-curious about where the world's going and what's changing so that you can master it before anyone else does.

You, uh, there's this cool book called Grit. We talked about it a ton here on this podcast, and you cite it a bunch. Yeah, it's awesome. I forget the exact equation, but it's basically like she—

Angela Duckworth, she's like, I think she started, um, the original book with 50% passion and 50% perseverance. And, um, one thing we highlight— we actually had a chance to talk to her, which I'm super grateful for— but we found this podcast she had done 10 years later where she said it probably shouldn't have been 50/50, that it needed to put more weight on passion. And her, her fear is that we've talked children, young adults, how to grind. So that we've taught them to persevere for the sake of perseverance. And she believes that now— that now she believes that leads to burnout. And so if you have like all this effort without the love for it, it feels more like work. And one of the things, you know, my— the second principle here, after you chase your curiosity, is to hone your craft. And that's a lifelong journey, always learning. And for people that are in the right space, that comes free. Like, you just do it naturally. You wake up and want to do it. Like, you're drawn to knowing more about the craft. And, and I think that that correlates nicely with where she, where she came out, which is you— it's hard to do all the things I recommend in this book if you don't truly love it.

I didn't realize it, but passion, I think, is Probably. I think passion is kind of a bad word because like passion kind of implies that I'm going to like everything I do. And if you like talk to like a lot of athletes, they're like, well, I love competing. I do like practicing, but there's definitely days that I hate doing it. But I'm a pro and I'm going to do it no matter what. And like, I love winning.

We highlight in the book that that word's kind of cliché and overused. Seinfeld gave a talk at Duke where he said fascination was a better word. I think obsession is a good word. Um, we titled the chapter Chase Your Curiosity. Like, what, just what is it that you, you can't ignore? Like, what is this thing that you love so much that you always want to know more about it?

You know, what was your, uh, you did a good job of like listing all these exercises to like find it. What was the, uh, most productive one that you found?

I mentioned the one that Tito had used. Um, the, the team that wrote Designing Your Life has, has one that they say is most popular, which is, is battle carding. So like come up with 3 to 5 potential career paths, not just one, and let your brain roll around in them for a while. So you, you could do that, especially with AI today. You could imagine, I'm going to do this, what does it look like 2 years from now? Like, who are, you know, what might I like, what might I not like? You can, you can, and then, you know, you could say, well, what if it were this or this? So that's an exercise. Um, I think having the mental relaxation, to not feel like some path you've been down is sunk cost. Like, I'm going to go try this, and if it works, great. If not, I'll do something else. Just as your parents said it's okay to quit college and go work there, um, it's okay to quit the job you're in as well. And I just fear we put so much weight on economic stability. You know, you mentioned some of those immigrant families and what they, they pushed that, that there's this burden to do that above and beyond what might be fulfilling in your life. And I, I think it'd be better if we got out of that. And, and, or, or at least this way, think of it as a, a, a, you know, a gauge. We've gone pretty damn far to one side. Let's, let's bring it back a little bit.

Have you messed up with your— like, have you had to pull yourself back with your kids?

Yeah, yeah, yeah. I think there is a And having, um, they're all in their early 20s, so they're all trying to find it. Like, I don't know if they're all even there yet, but there is this intuition as a parent, and I, I think it's well-intentioned to, to, to worry, to feel like they're on a safe path. And safe is usually economic, but it's also, uh, it's just risk feels like your risk. Like, like, and, and I, I love the story of what your parents did, and I've got a few anecdotes I found since we finished the book that are great on, that are very similar to what your parents did. But I think it's the exception. I don't think it's the rule. I think a lot of parents would have tried to convince you to finish out and get your degree. I think that's built into, to most, uh, parents. And, and so there are other people other than myself that, that have highlighted that the, I'd call it like this industrial college matriculation path has gotten very rigid, and, and it's competitive, and it's grindy, man.

The, the— like, getting into college now is significantly harder.

Yeah, they've not expanded— they have not expanded the enrollment at these schools, but the number of people that want to go to college has gone way up.

It's crazy.

It's crazy. And, and starting around 6th grade, once again, well-intentioned parents start building the resume to get into college. And so We overschedule children today compared to when I was young. For sure. And so they're scheduled from when they wake up to when they go to bed. There's actually a chapter in Jonathan Haidt's book, Coddling of the American Mind, called The Decline of Play, where we've just, it's harder, I think, for a child to explore and try on different ideas because they're caught up in this game to try and get into college.

You had this crazy stat. You said, I think it was, uh, the people who won a Nobel Prize in science, the scientists who won Nobel Prizes, correct me if I'm wrong, but they were 22 times more likely to participate in things like acting or dance class and things like that. What was that stat?

So this was work that Keith Holyoke had done at UCLA, and it relates to a lot of the concepts in the back of Range, the book by David Epstein. But it was The people at the top of their field are like much more likely to have a breadth of hobbies, speak more languages, do more things, and almost, I think, have a lens on the world that's broader because they were able to try so many different things.

So I read this book, Mastery, and like the premise is like being a generalist is kind of nonsense. You have to specialize in something, but once you specialize, then you become a generalist.

I think that's the right pathway. Like, I, I do think you want to get started in an area where you can differentiate yourself. And then, and then in many— in both the principle chapter on mentors and peers in here, and even in the learning, uh, principle, I recommend, you know, as a more advanced level, once you get, you know, up to this level, then go broader. Like, start to learn outside your field, find mentors and peers outside your field. And you'll get pulled in more innovative ways.

So tell me more about that. That like just like kind of blew my mind.

Well, I think what Keith's work highlighted was that some of the people that are able to reach the top of their field are able to draw on mental models from much— from a variety of different places. And where a hyper-specialist— and David Epstein's book Range is all about this specialist versus broad thing. Like, that's the really the the whole point of the book. And he quotes Holyoke as well. But many different innovations in science have come from people who repotted from one place to another, chemist who becomes a physicist. The person who's a lifelong physicist has mental models that are pretty rigid at that point in time because that's all they know. And so once again, I think this is an advanced skill. I don't, I think after you're succeeding, you start to do this. I don't think it's the pathway to the beginning of success, because I think you'd just be too broad. But some of the smartest people I know, like, like one person profiled in the book is Danny Meyer, the great restaurateur. We were asking him about his mentors, and one of the mentors that influenced him the most isn't from the restaurant industry, you know. And so it's, it is a more advanced skill, but it is where you will look. The whole goal, I think, is to differentiate yourself along the pathway. And that is a great way, more advanced way, but a great way to take yourself places you wouldn't have thought of.

You had this cool line. You said there's, if there's one takeaway that you should have from this book, peer groups more so than coaching, consulting courses, whatever, is probably the most powerful thing that you could use. And it's underdiscussed because it doesn't feel intuitive to like want to be peers with someone who might take the same job as you, but it's really powerful.

I think the way you describe it is right. Like, everyone talks about mentors and no one talks about peers. So I do have a chapter on mentors and I offer a ton of very practical advice about how to play that correctly. But the peer thing, the idea is that when you get on that first rung of the ladder and you're trying to climb it, if you could develop a friend group, it might be 4, it might be 6, that are also on that same journey and hopefully, I think, outside your organization. I think you could start maybe with one person in your org, but for all the reasons we just talked about, how breadth of knowledge might give you insights you wouldn't have, if they're outside your org, they're going to see different cultures, they're going to see different management structures, they're going to bring a different viewpoint to you that you wouldn't have had if they were inside. And then with today's modern tools, you know, Create it. Create it. If you're adventurous, create a Slack channel. If you're— if you just want to do a WhatsApp group or a Signal group and share, you know, share your learnings along the way.

When I moved to San Francisco for Airbnb, it— I didn't actually end up getting the job, by the way. They offered me a job and I got it. And then when I was in college, I was like kind of crazy and I got arrested. I got DUI and I'm sober now. I don't do any drugs or alcohol. I'm completely clean and by the book. but they're like, you lied on your resume. You said you didn't have a criminal record. And so I didn't end up getting the start. And so I was stuck out in San Francisco. I was like, what the hell am I going to do? So I ended up starting a company and it worked out well, but it was like super low point in my life. And when I got there, I created this thing called the Anti-MBA. It was my version of a book club and we met once a week and we would get a book and we would read a book a month and talk about a quarter of the book every single week. And it changed my life, like having those group of guys to like— and I think that like you need a few things to make a group like that work. I think you need like rules, you need like some rituals, and you need to like take it serious.

Yeah. And I think if there are people that are sharp-elbowed, that are climbers, that, that step on other people, you kick them out. Like, I, I think you need like-minded people who are equally gracious to one another.

Who is in your group now that's like a big shot now?

Well, we— one thing I've, I've, I've discovered lately is setting up different, like, WhatsApp or Signal groups for different topics. I think for someone coming in early into a career, it's better to have people that are on that exact journey, and I'm not in that place anymore.

I have a company called Hampton. That's my main company. Are you familiar with YPO?

Sure.

It's like YPO, so we have thousands of members all over the country, and you—

it's Chris's peer group.

And then we have executive coaches who, like, lead the conversation. It's for CEOs. So you have to like, the average person has like $30 million, $20 million in revenue or so. And it's been really cool to like watch these members, like team, and I'm in a peer, we call 'em core groups. I'm in one as well. And it like, you have this, a bunch of lines in there about peer groups and I'm like, oh, you're writing my ads for me.

Yeah. But, but, but, and those things exist with YPO and, and your thing for CEOs, but it could be done by anybody.

For sure. I mean, like, my wife, when she was pregnant, she had one for moms. I've got a buddy of mine has one for Jewish dads. Like, like it could be anything, you know what I mean? But like, it really does like change things.

It does. It really does. I think it can. And almost all of the other principles are accelerated. So your learning is accelerated. There's a great story in the book about MrBeast that ties to that. There's a, your network is accelerated. So your network isn't just your network, it's now the network of the group if people are willing to share introductions and that kind of thing, both for mentors and other peers. And then the group, I think, can be really helpful on bad days, and everyone's going to have bad days. And there's a support element that comes into play that I think is really useful. And then also, You, you may be at a shitty company, like your, your dream job may be the one you're in and you might be at a shitty company. And if you're alone, you have no way of knowing if that's normal or not, like the, the stuff you're exposed to. Whereas if you had a group of 8 people that were all doing this in different companies, you'd get different perspectives on that.

What did the voice to you say when it was like, I found my calling?

There was a lack of that voice that kept asking 'Is this what you want to be doing 30 years from now?' Like, that worry was gone. Like, I wasn't having those negative thoughts, if you will.

And what was the thing that you were doing? Investing?

Yeah, once I became a VC, I just adored every minute of the job. But a lot of that's fitting my individual personality, you know. There are people who, you know, are kind of— they go, 'Oh, you can't be a VC because you're not the one actually doing the work.' That never bothered me. You know, I'm someone who's really drawn to intellectual breadth. And so a service job, whether it's working in banking or working as a VC, gives me a window across way more companies than if I were working in one. And I also— I'm fairly certain I have ADD, and like focusing on details is not something I'm good at. Whenever you—

when I've heard Jeff Bezos or Warren Buffett, someone was like, I tap dance to work every day. And then you're saying you adored every minute of it. It's like, I think I found my passion, but like, I probably like running a company, it sucks like 85% of the time.

I get that.

And like my last company that sold and it was great. Like if you talk to my wife, she was like, you laid on the floor like all the time saying, I can't do this. I want to quit. This sucks. Like is adored every second of it the right?

Is that truly accurate? I don't really, well, I'm telling you the ex post kind of summary of it all.

But like how many times when you were doing it, did you want to quit?

I don't ever remember wanting to quit.

Really?

Really.

That makes me feel horrible.

I think the CEO job's the loneliest job in America. I've said that many, many times before. It's hard. And one of the things that makes it particularly hard, you need to run culturally opposite what's happening at the company. So if the company's doing poorly, you have to bring the positive energy and make people believe it's possible. And if the company's running hot, You want to bring them down to earth. And this is my, this is my theory on why the CEO job's so hard. So running counter emotionally to what everybody else in the organization feels is exhausting.

It's exhausting. In a world where, like, I've, I've grown to dislike the word and the idea of authenticity. It's sort of like when you're a young kid and you're trying to meet girls, people say just be yourself. And I'm like, girls don't like myself. Like, why would I be myself? Like, I need to change and be better. And then people are like, be authentic. And I'm like, but I'm not a good leader. I need to be better. You know what I mean? And so they'll be like, be authentic. Like, be transparent with your team. Tell them that you're not feeling great. I'm like, no, lie. Like, you have to like convince them that like, we're going to figure this out. And somehow you will. You know what I mean?

I do. Leadership's really, really hard. I think one of the things that is often not talked about enough in the whole both Silicon Valley and just the, the celebration of the founder is that, that if you're successful and your company grows, you're going to go from 10 employees to 100 employees to 1,000 employees, and eventually leadership's going to be required and matter. And you don't have a place to learn that, you know. It's not— there's no book that teaches, oh, here, you're a founder, you want to learn to lead people, like And it's not discussed much, but the Zuckerbergs of the world, I know for a fact that Larry and Sergey, there's this gentleman named Bill Campbell who's unfortunately passed. He was—

Trillion-dollar coach.

Yes, Campbell was there 10 years after the IPO. He was still running the weekly team meetings with Larry and Sergey.

Were they just bad leaders? I mean, what?

I don't know, Steve Jobs used Bill also. So I don't know that that makes them bad. I'm just highlighting the fact that there's no reason from a DNA standpoint that a founder should naturally be able to lead 1,000 people because there's a skill set required to lead 1,000 people and no one's taught it to you.

Can you learn it?

Yeah, I think you can learn it. I think certain people have. I think Zuckerberg's learned it. I think Bezos didn't have any leadership skills going in, like he had never run a large team.

But what do you suggest to someone to learn how to be a better leader?

Get to know Bill Campbell, but that's no longer with us. So, um, You know, I've, I've often said, um, get 2 or 3 mentors that have ran large groups. They will all have their leadership philosophy and patterns, and try those on and see which one fits you the best. So maybe that's maybe in the middle between, between the authentic and not. Like, you having a program and philosophy is better than none. I can't tell you how many Founders have gotten to like 200 employees and they're not running a weekly meeting, like they don't know to do it. So some structure is better than no structure. And therefore, rather than say one of those CEOs you talk to is absolutely right, find out what they're doing and see which one feels best for you and your org.

Well, you talked about that with Danny Meyer. Uh, Danny Meyer, I think probably most known outside New York for founding Shake Shack. You said that, um, I think he was gonna be a lawyer or something and he, and he, and he hated it, but he went and toured a bunch. His uncle was like, dude, what are you doing? You gotta be, you gotta get in the restaurant business. And so what he did was he did like a field trip to like tour restaurants and then eventually got a part-time job as, uh, working at a restaurant before starting his restaurant.

Yeah. He also did a tour through Europe as a stage, which is a fancy word for work for free.

But you, in the book, you're like, he still does that. So like whenever, like they're opening up a new restaurant, he goes and like field trips, and then you're like, when he opened up, I think, a barbecue place, he like went back to St. Louis and like tested stuff. Is there a world where like a white-collar job, uh, person can take these field trips?

Like, I think so, or at least the notion of it. I— one of the arguments I make, like, pound the table in the learning chapter, is that most people don't think about continuous learning in their job. Now, the founders do because they're learning these new technologies, and maybe doctors do because it's required by law, but most people that get into a field, I think the college experience and the high school experience were so exhausting, they're like worn out and they're like, I'm glad I'm done learning, and then they're gonna go to work. But whatever you do, I guarantee you, especially with AI out there, there's some nuance of what you could be doing that's new. And unless you're trying to find that edge, somebody else may be. And I think the people most at threat by AI are the ones that aren't continuously learning, that are just kind of doing the same thing they did 10 years ago because they're kind of a widget, you know, and that could be automated. And the people that, that are curious about what's possible, They're naturally going to see this AI thing pop up and go, wow, that's a new tool. I better figure out what it can do for me. And those are the people that are hardest to replace. Like, if you're— if your company's trying to figure out AI and one of your employees is spending more time on it than everybody else, they're the last person you're gonna fire.

I think that, like, what I've been trying to tell a lot of— like, we have a lot of young people listen, particularly a lot of young men, and I'm like, you have to understand the difference between risk and uncertainty, and that risk is oftentimes a lot less than people think. But uncertainty will always exist no matter what, and you just have to get comfortable with that. And I think that in order to reduce risk, I don't think people realize how many things in life they can try before they buy. For example, I moved from Texas up here. Yeah, I rented an Airbnb for 2 weeks in a neighborhood that I wanted to see, and like, I tested it out and I actually realized I hated that neighborhood. I like this other area.

Yeah.

Or like you could do that. I remember before I wanted to— I, one time I wanted to buy a fancy car. I tested it on Toro and I was like, oh, I don't want to own this car. This is a pain in the ass. Yeah. And like you can email someone, you got to email probably 50 people and you could like actually shadow them. I mean, most decisions are reversible and there are ways to like reduce risk.

No doubt. And like, like when I was an engineer and before I went to Wall Street, it turns out I had read Peter Lynch's One Up on Wall Street. I was trading stocks in my spare spare time. So unconsciously, I was testing that in this field that I would eventually go towards. And so yes, like, don't quit your job tomorrow just because you're unhappy. Start figuring out that you're— what direction is the right direction to move towards.

Some of the people that you talk about, like, for example, in the book you talk about Robert Zimmerman, AKA Bob Dylan, and you're like, he, um, found his fascination and he like followed that route like pretty ruthlessly and became Bob Dylan. And but then you also are like, he's also like, you barely mentioned this, but you're like, he's notoriously prickly. Like he's hard to like get close to. But then like, I know you've worked with Travis Kalanick, who's like a pretty wild guy. The people who, in order to like do these exercises of finding your passion, do you sort of have to be like a ruthless asshole, you think?

I don't think so. I mean, Danny's one of the nicest humans I've ever met in my entire life. Even though someone like Bobby Knight, who we have in the book, is known as being that way, he's probably got the biggest coaching tree in the history of the sport, which means people have developed underneath him, and both as coaches and players, and become coaches. So even if, you know, this prickly guy you see throwing the chair is not the one that developed all these humans, you know, and put them on their way and on their path. And one of the things I love about a lot of the stories in the, in the book is that these people reach a place where they're touching so many people in their field. I think that's a more fulfilling test of were you successful than did you hit some milestone.

Yeah, but it's a lot easier to do a bunch of stuff like following your passion when you have hit milestones. Like sometimes when people, people say follow your passion, what I really want to tell people, I'm like, basically, this sounds like crude, but I'm like, if you can get rich fast, do that.

Some people get in a position where they spend right up to what they earn, and then they don't have— they don't have flexibility. And so you move from one town to another. A lot of the people in the book do that. And if you're stuck, you're stuck. You know, you might have to stay in a job because you've built an expense burden it goes right up against the top of it. I saw a ton of those people when I came to New York.

What did you see?

I mean, we were getting paid decent money, like, for—

this was when you're a researcher?

Yeah, yeah, for entry-level jobs. But they would run and get— they'd go get the place in the Hamptons and they'd join the private club and they'd run their budget right up to the top, sometimes above it. It's where if they don't get the bonus, they're underwater.

I know people that make 7 figures a year, $1 million a year, and will literally have $0 in savings.

I understand.

When I early on, I used to use this app called My Weekly Budget and I created a budget and I had a spreadsheet that would track how much cash I had saved. So $10,000 to $20,000, it was like, this is how long you could live without any income. So the name of the game was to squirrel away as much cash while keeping expenses low. And it was like, what, anything above 6 months, that's like your FU number, meaning you could like go and like try and experiment.

Yeah, it gives you flexibility.

Yeah, and it was like, but it was like ruthlessly disciplined to make that number bigger, even though I didn't make a lot of money, but I was like living very frugally. And I don't think people understand that. And like things like college debt, which I'm very privileged I didn't have, completely ruins it. And so like there's a bunch of these like irreversible decisions that can really screw you up when it comes to like being able to like chase down some of these things.

You know what I'm saying?

I agree with that. Last night was special because I sat across from Jim Cramer.

Yeah.

And then next to him was Henry Blodgett, who founded a business Insider, just a lot of like crazy people. When you knew these guys when they were younger, was it clear that you guys were all going to, uh, succeed, or have you been surprised that someone has been as successful as they are?

Well, I think he— I think it goes back to our discussion on peer groups. Like, like connecting with— I've just always found, um, and I think I got more attuned to this the older I got, like having— have a big tent mentality. Like, have as, have as many friends as you can. Try not to judge people too much. Root for people to be successful when you can, and, and it'll come back to you in spades, you know. And I guess I've never been surprised that the people that end up, you know, in San— in, in Silicon Valley, in the middle of it all, continue to move forward just because it attracts so many ambitious people. You know, and so I don't know, I haven't, I haven't been radically surprised by anybody's staying power. Keep in mind, I'm 59 years old, so I have the benefit of time to build that network. I had 25 years as a venture capitalist.

But I think you were on the board of, uh, what's the one with you and Danny Meyer? You're on the board of OpenTable. That was like 20 years ago.

Yes.

It seems like you kind of like hit it right up pretty early.

And yeah.

Into investing, right?

That's kind of key in venture.

What do you mean?

Oh, just to be in front of the, the wave or whatever rolls out. Like, you can't, can't be late.

With AI going on right now, is this— does this remind you of a different period in venture?

I've never seen it quite like this.

Really?

Really. I— one thing I think throughout my career, venture's only gotten more competitive. And now today, it's, you know, as I've— I'm hanging up my boots and watching the next generation, it's even more competitive. And the, um, the burn rates that the VCs are comfortable experimenting with are bigger and bigger than ever. Like, I thought our $2 billion a year burn rate at Uber was pretty frightening. OpenAI is burning way more than that.

How much are they burning?

I, I don't know. I've seen different numbers.

I don't have access to their financials, but like, Uber was losing $2 billion a year.

Yeah, but OpenAI is at like $8 or $10 What did—

what does it make you feel when your company's losing $2 billion a year?

Scared shitless.

Really?

Yeah. Oh, yeah.

How did you map that out? Like, how do you go to bed at night knowing that? Like, are you like— what do you tell yourself?

You're like, well, I didn't sleep much. There was a piece of it that was— that I think is, as the venture industry gets more industrialized, was a problem, which was I think the Lyft investors knew that they had to keep funding liquidity. And for a bunch of reasons that relate to network effects, that it was always supposed to be kind of a single marketplace that would win. And but you, if you don't have the constraint of financial viability, you can lose money to create the, to the perception of liquidity. You can pay drivers to be present when they wouldn't naturally be there.

Yeah, I used to joke, my last company in San Francisco, we didn't take venture capital, but we used to say we were still VC funded because, uh, Uber and all these companies would give like the craziest referrals. So like, I remember like giving my referral to everyone, like, oh, I drive on Uber for free, or I ride on Uber for free.

I get it. And, and, and, and it wasn't until Lyft went public first, which is probably the best thing that could have ever happened to Uber, where Wall Street held them accountable for being profitable. And, and it's, it's at that point when things really tipped and where Uber was able to then take advantage of the network effect and being larger and, and now spits off well north of $10 billion a year in free cash flow.

That's how big it is now. That's insane. Did you— is that bigger than your prediction?

On— I made a prediction about the, the market cap. It had a bunch of ranges. I don't have it in front of me, but Dara got it to $200 billion market cap. And I don't know if that was in I assume you're referring to the blog post I wrote.

No, I haven't read it.

Oh, okay. Yeah.

What did you say? Or what was the other one?

There was a professor at NYU that wrote a blog post that said it would only be worth $4 billion, and I pushed back.

I remember that. We did talk about that. Yeah. Did you see the blog post the other day about on Substack where they're like, AI is going to make the economy worse? Do you see how one blog post like brought down?

It's pretty amazing.

That's crazy, right?

Yes.

Did your blog ever do that?

Not, not of that scale, no.

Yeah, that was, that was insane.

Insane. There's a lot of fear out there. Just remember, uh, Warren Buffett said, be, be greedy when others are fearful and fearful when others are greedy. So the first wave of AI was a lot of people being greedy, and now all of a sudden there's fear for the first time. So if you're a net buyer of stocks, this is when you, this is when you sharpen your pencil.

You see all these interesting founders other than like, I mean, I don't want to hear like Travis or like some of the big name ones who kind of have stuck out as like being like particularly sticky and formidable.

Well, one of the most impressive people I know is a guy named Rich Barton. He founded Expedia and then Zillow. Expedia was acquired by Diller, so he knows Barry and all that. But, but Rich has this remarkable ability to be top 1 percentile as a product technology disruptor, but also as a leader. That thing we were talking about before. And I, I usually see people tilt one degree or the other and not both. And he's this rare person that does it on both. And so I frequently lean on him for advice.

Do you have an example of like a story of like where good leadership changed?

Getting companies to pivot fast when they need to. I mean, right now with AI, any companies out there— you mentioned what happened with this report, like that, that DoorDash is down 5% because the report said you could build DoorDash for free, which I don't believe, but you know, whatever.

Yeah, and that report, by the way, for the listener, it was basically like, what happens in the world if AI is so efficient that we don't have jobs? And if we don't have jobs and we're not buying stuff, And it was just like a story. It was an idea.

But how do you get— so the thing that I was going to mention is just how do you make sure your company is properly aware of this new wave and how do you get everyone super excited about figuring out what it's going to mean for your company? And that, that's not easy to do. And, you know, I'm back on the board of Zillow, so I watched them do that recently and it requires having both the conviction to make that kind of pivot and move and then the ability to get the people to follow you.

That's funny that you said it was like being good at product and being a good leader. I think you also said— do you also say that like Jeff Bezos is one of those guys who does two things really well?

It would be a good exercise just for someone to kind of write down the leadership techniques of Jeff Bezos because Amazon remained innovative after it got to like 100,000 employees. And that's very hard to do. It's not one human, it's one human creating a system that reinforces whatever he thought. You see what I'm saying? And like, how do you make that system keep doing that even after, you know, on days you're not there? And him and Elon, I just don't think people fully grok how they're able to lead.

A lot of these people who are these type, like, kind of the titans of industry that you know, do you think that there's any correlation or reverse correlation, uh, of, uh, happiness?

I don't know anyone that laughs louder than Jeff Bezos. If you've been around him when he lets go one of his, his guffaws, man, I, I know, and I think he really loves life. Um, I, I'm just saying there, I don't think there's a correlation. I mean, I, I, every chance I get, if Toby from Shopify does a podcast or something, I'm eating it up. And I find his attitude on leadership in life to be lighthearted.

You know, he seems like another one of these product leadership guys. He's got a very unique flavor of leadership. He has a very wise—

he's got something wise about him.

Yeah, there's something wise about him. Do you see where he took screenshots of his computer screen every 10 minutes for the last 20 years? And because he was just, he's like, I'm a nerd and I just love like having this diary of like what, what was on my, like he was tracking all of this and he's like, I didn't know what I was going to do with this. Now that AI exists, I can like upload this and like it could like teach me about myself. But he's got this like really cool, I call it like nerd wisdom, like, you know, Dharmesh at HubSpot.

I have met him, but I don't know him as well.

He's kind of the same thing where there's these groups of guys who are like very— like when you think of a leader, sometimes you think of like a Napoleon, like rah rah, like rile people up. But there's this other group of like fairly introverted people and they're quiet. And when they talk, you listen. But I think they're both useful. For someone who's like 18, 19, 20, they're listening to this. You did all this research for this book. What biographies do you suggest they go read?

I mean, I think it would be heavily dependent on what interests them, or rather what made the biggest impact on you. I don't know if I was reading biographies at 17. I really got into reading when I got to business school, and I— they're all listed in here. There's 35 books listed at the back of the book. So I— but it— I think the key is just to— and I don't even know that it has to be reading. There's, there's so many podcasts like the ones you do, and, and YouTube interviews with people. Like, it's so easy to go learn about something. So I'm just like, whatever interests you, go learn more about it and see if that takes you somewhere. See if that makes you excited. See if it makes you want to pick up the next one. And if it is, I think you're probably in the right lane. If not, just pay attention to what fascinates you, you know, pay attention to what interests you. I'm a big believer that more people can chase careers in their hobby than someone else might say. Like, if there's something you're just super passionate about, even if it's a hobby, you might be surprised. There might be a way to make a career around it.

Well, it's a lot easier now with the internet.

It's— this is— by the way, I would love to close with this point that you just made. If you're a What— like I said, if you're someone who's disengaged at work, that went through some process you didn't care about that much, I can understand why this AI thing would feel threatening to you. If you're crafting your own personal career and you're high agency— I think that's a word you used earlier— AI is like a jetpack. Like, you can do more stuff than you ever could before. You can learn faster than you ever could before in the history of time. You can find people to connect with. You can network faster than, than you ever could before. And so if you have agency and a direction you're headed in, AI is going to make things way better. So I think it's just this interesting paradox that there are people out there who fear that it's going to dismantle them, and there's people out there who are like, oh my God, I can't— I've met so many what I would call like SMB founders or regional founders running you know, businesses that are laundromats or storage facilities, and, and they've discovered all the things they can do with AI, and now they, they feel superhuman.

So I'll, I'll wrap up with the story. You'll dig this. So my mother-in-law, her name's Smithy, she came here, uh, to America from Haiti at like 14 years old, didn't speak English, um, married my father-in-law Jeff. Jeff owned a moving company. Smithy was a stay-at-home mom for a long time. The kids grew up, and she was like I'm kind of lost. I need to do something. What's going on? So about 5 years ago, she says to me, she goes, Sam, I think I'm going to start an online store that sells pillows. It's like pillows, um, or whatever. Sounds good. And I like, I was like, there's this thing called Shopify. Just start, just start there. It's been 5 years since that. She now has a pillow company that sells over $1 million a year in pillows. She has a warehouse in New Jersey with 5 full-time employees selling pillows. She was just on the pod. And she uses AI like all day to like, she's like, how do I buy an ad? And like, you know, ChatGPT like teaches her, or she's like, uh, how do I whatever? Like it's YouTube and ChatGPT like telling her what to do. And she didn't know, she didn't know the word e-commerce. She didn't know what that meant. She basically just knew what Google was and that was it. And now she, in her late 50s, started an e-commerce business that does millions of dollars a year.

That's amazing.

Crazy, right?

Yeah, no, but there's never been a better time to propel yourself forward if that's, if that's what you're prepared to do.

Well, thank you for doing this, brother.

All right, all right, God bless. Take care. Yeah.