Bill Gurley: 6 Out of 10 People Are Making This Mistake

If you're crafting your own personal career and your high agency, AI is like a jackpot. 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 have you been doing it? Did you want to quit? I don't remember when I was doing it. 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 a bunch of crazy staff in the book. I want to talk about the Nobel Laureate thing. That was interesting. But one of the craziest things early in the book, I think did you run this survey? And it said that like six or seven out of 10 people hate their job. Yes, 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 a thousand people if you could start your career over again, would you do it differently? And seven out of 10 said yes. And then we took that to warn the people in analytics to do the official academic version. So you make sure you get all the statistical data correct. And their number came back six out of 10. So still a really big number. Crazy. There's a great book by Daniel Paine called The Power of Regrets. And he has a somewhat similar survey data of longitudinal through people's lives. And as you get older, you're regrets of inaction start to really weigh on you and ruminate in your brain. And a regret of inaction is Tuesday, 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 to door. I never opened is heavier in their mind. And the survey might have been getting it 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 Green. Yes. I feel like it was 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 and 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 six out of ten or the four out of ten? Do you find that like even when you were when you left compact 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 three years. So I you were like a research. I was in a cell site research channel. So I had two 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 that's done at 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 two or three 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 best part was the early part about finding your passion. And you're like, that's the hardest part. And like you said that 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 Bayesos is famous for. Cook, what he calls a 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 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 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. What 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 may have benefited in the back of my brain from the fact that my father went across the country. He took a flyer on a job. He got recruited from Virginia to Houston to be one of the first employees in NASA. That's cool. And I knew he had done that. 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 why I paid my way to college. It was called Southern Sam's. We nurses, big as the babies arm. And we had a bunch of locations that these hot dog stands. It was really fun. And I was like, this is so hard to be out in Tennessee, whether it's hot dog. 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 Uber Cab Still. And Air Bed Embroofest. Yeah. And so I started looking at this thing called Air Bed Embroofest. And I called email this guy named Brian, this CEO. And he didn't reply to me. But then I found like another employee to email and they've just in. And I emailed him. And I was like, I'm going to be there. I'm Monday. Can I interview for this company? Obviously, Air Bed Embroofest is called Air B&B. And they're like, yeah, you live in the Bay Area. And I was like, yeah, 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. I got the interview. I got the job. Went back to Tennessee. Dropped out of college. Sold everything I had. But my parents are entrepreneurs. And Missouri, they started their entrepreneurial career owning a fruit stand. Yeah. And I remember when I told them I was like, I'm going to leave school. I'm going to join this thing. And they're like, what's the start up? 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 going to be fine. And they're like, okay, cool. We'll come pack up your stuff. And I remember at that moment, that emotional support, it 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 the immigrant experience is interesting, because a lot of the immigrants, it seems like they've fallen to 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. Go to school this up. Take the safe path. Right. And my parents were not the safe path. And that was 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 the 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? You're doing this. And I think that that's like, I think that's why I'm still upset. I don't think I've ever formally, I don't think we've ever formally learned how do you find, I call it eekie guy, 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? And so it's interesting, the reason I like your book is because that's what it's about. And yeah, and in the chapter title, "Taste Your Curiosity," I tried to borrow as many of those type of exercises as possible, even when 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 just trying to give people as many of those pathways as possible because 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 mentioned that one. There's a story in the book about this guy, Bert Beverage 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, right on the left, what you love to do, and on the right, what you're good at, and trying to 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, 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 a question, the answer's no, because the conqueror is just conquer. And I hated his reply to that, because 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. - I don't know. - It doesn't, 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 in 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 that Gates took or even Bayzo. So I don't know that there is a pathway to that place. I'll tell you, I want to ask Jeff Bayzo's, how he could possibly be good at angel investing while he's running this company. - What did he do angel-wise? - Oh, he did Google Hoover. But he's a murderous road. - He was in the, he was in the seed round of Google. - Yes. - Wow, that's amazing. What was the evaluation then? - I think that first round was a 10 poster. But to get to the point, he said, the only thing he looks for is this insane determinism. He wanted to believe the person was gonna 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 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 are, this is a cool book called "Grit." We talked about a ton of 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 the original book with 50% passion of 50% perseverance. And one thing we highlight, we actually had a 10th talk to her with some super grateful for, but we found this podcast she had done 10 years later she said it probably shouldn't have been 50/50 that it needed to put more weight on passion. And her fear is that we've taught children, young adults how to grind. So 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, 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 I think that correlates nicely with where she came out, which is 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's kind of a bad word. Because like passion kind of implies that I'm gonna like everything I do. And if you like talk to like a lot of athletes, they're like, well, I love computing. I do like practicing, but there's definitely days that I hate doing it, but I'm a pro and I'm gonna do it no matter what. And like I love winning. - We highlight in the book that that word's kind of cliché is you know, we're used, Seinfeld gave a talk at Duke where he said, fascination was a better word. I think obsession's a good word. We titled the chapter Chase Your Curiosity. Like what is it that you can't ignore? Like what is this thing that you love so much that you always wanna know more about it? You know? - What was your, you did a good job of like listening all these exercises to like find it? What was the most productive one that you found? - Oh, I mentioned the one that Tito had used. The team that wrote, designing your life has one that they say is most popular, which is battle-carting. So like come up with three to five potential career paths, not just one and let your brain roll around in them for a while. So you could do that, especially with AI today, you could imagine I'm gonna do this. What does it look like two years from now? Like who, you know, what might I like? What might I not like? You can, and then you know, you could say, well, whatever this or this. So that's an exercise. I think having the mental relaxation to not feel like some path you've been down is some cost. Like I'm gonna 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. 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 immigrants families and what they push, there's this burden to do that above and beyond what might be fulfilling in your life. And I think it'd be better if we got out of that. And, or at least this way, think of it as a, you know, a gauge, we've gone pretty damn far to one side. Let's bring it back a little bit. Have you messed up with, like have you had to pull yourself back with your kids? Yeah, yeah, I think there is a, and having, 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 think it's well intentioned to, to worry, to feel like they're on a safe path and safe is usually economic, but it's also, it's just risk feels like you're risk. Like, and I love the story of what your parents did. And I've got a few anecdotes I've 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 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. And 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 is going way out. It's crazy. It's crazy. And, and starting around sixth grade, once again, well intentioned parents, start building the resume to get into college. And so we over schedule children today compared to when I was young. For sure. And so they're, they're scheduled from when they wake up to and they go to bed. There's actually a chapter in Jonathan Heitz book calling of the American mind called the decline of play, where we've just, we've, we, 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 the people who want a Nobel Prize in science, the scientists who want Nobel prizes, correct me for a moment, 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 that 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 having lends on the world that's broader because they were able to try so many different things. (upbeat music) - Today's episode is brought to you by HubSpot. Did you know that most businesses only use 20% of their data? That's like reading a book, but then tearing out four fifths of the pages. Point is you miss a lot. And unless you're using HubSpot, the customer platform that gives you access to the data you need to grow your business, the insights that are trapped in emails, call logs, transcripts, all that unstructured data makes all the difference because when you know more, you grow more. And so if you wanna read the whole book instead of just reading part of it, visit HubSpot.com. - 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 do think you wanna get started in an area where you can differentiate yourself. and in many ways. And both the principal chapter on mentors and peers in here and even in the learning 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 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 whole point of the book and he quote to Leo, because well, 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 one person profiled in a book is Danny Myers, a great restaurant tour. We were asking him about his mentors and one of the mentors that influenced him the most isn't from the restaurant industry. And so it's, it, 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. And so this cool line, he 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 under discussed because it doesn't feel intuitive to like one of the peers with someone who might take the same job as you, but it's really powerful. I think the way you describe 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 four, it might be six 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 work. 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 work, 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 insights. And then with today's modern tools, you know, created, created, if your adventure is created, Slack channel, if you're, if you just want to do it, what's that group for a signal group and share, you know, share your learnings along the way. When I moved to San Francisco for Airbnb, it, um, 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, and by the book, but they're like, you lied on your resume. You said you didn't have a, or a criminal record. And so I didn't end up getting to start. And so I was stuck out in San Francisco. I was like, what the hell am I going to do? I ended up starting a company and it worked out well, but it was like super low point 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 sick 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 like ticket serious. Yeah, and I think if there are people that are sharp elbowed or climbers that step on all the people you kick them out, like I think you need like-minded people who are equally graces to one another. Who is in your group now that's like a big shot now? Well, we, one thing I've discovered lately is setting up different like WhatsApp or signal groups for different topics. I think for someone coming 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 from the YPO? Sure. It's like YPO, so we have thousands of members all over the country and it's Chris Peer group and then we have executive coaches who like lead the conversation. It's for CEO, so we have like the average person has like 30 million, 20 million revenue or so and it's been really cool to like watch these members like team- and I'm in a peer group, we come core groups, I'm in one as well and you have a bunch of lines in there about peer groups and I'm like, oh you're writing my ads for me. Yeah, but those things exist with YPO and you're saying 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 it could be anything, you know what I mean? But it really does like change things. It does, I 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 Mr. Beast that ties to that. There's 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. You know, 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 in and to play that I think is really useful. And then also you may be at a shitty company. Like your dream job may be the one you're in and you might be at a shitty company. If you're alone, you have no way of knowing if that's normal or not. Like the stuff you're exposed to. Whereas if you had a group of eight 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 to kept asking, is that's 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're doing investing? Yeah, once I became a VC, I just adored every minute of the job. But a lot of that is fitting my individual personality. You know, there are people who 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 sit, I've heard Jeff Bezos or Warren Buffett. Someone was like, "I tapped in 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 do, yeah. 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 the sucks." Like is adored every second of it the right? Is that really accurate? I don't know. I don't know. I'm like, the ex-post kind of, the summary of it all. But like, how many times when you were doing it, did you want to quit? I don't remember whenever I wanted to quit. Really? Really? That makes me feel horrible. I think the CEO, Jobs, 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 there. And this is my theory on why the CEO jobs 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 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." I want to be myself. I need to change. It'll be better. And the people are like, "Be authentic." And I'm like, "But I'm not a good leader. I need to be better." You ought to be. And so there'll be like, "Be authentic. It's like, be transparent with your team. Tell them that you're not feeling great." I'm like, "No, lie." 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. I do. I'd leadership's really, really hard. It's often not talked about enough in the whole, both Silicon Valley and just the celebration of the founder is that if you're successful and your company grows, you're going to go from 10 employees to 100 employees to 1000 employees and eventually leadership's going to be required and matter. And you don't have a place to learn that. There's no book that he 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 was unfortunately passed. - He was a trillion dollar coach. - Yes, his Campbell was there. 10 years after the IPO, he was still running the weekly team meetings with Larry and Sir. - With age as bad leaders. I mean, but. - I don't know, Steve Jobs used Bill also. So I don't know that that makes him 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, no one's taught it too. - 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 that someone to learn how to be a better leader? - Get to know Bill Campbell, but that's no longer with us. So, you know, I've often said, get two or three 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 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 on 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 or. - Well, you talked about that with Danny Meyer. Danny Meyer, I think probably most known outside of New York for founding Shake Shack. You said that I think he was gonna be a lawyer or something and he hated it, but he went and toured about. 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 he got a part time job as working at a restaurant before starting his restaurant. - Yeah, he also did a tour through Europe as a stash, 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 a 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 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 a 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, we got them 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 that 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, and that could be automated. And the people that are curious about what's possible, they're naturally gonna 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 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. I rented a Airbnb for two weeks in a neighborhood that I wanted to see. And like I tested it out. And I actually realized I hated that neighborhood, but I liked this other area. - Yeah. - Or like you could do that. I remember before I wanted to, I went time I wanted to buy a fancy car. I tested it on Toro. And I was like, oh, I don't know in this car. This is a pain in the ass. - Yeah. - And like you can email someone. You gotta email probably 50 people. And you could like actually shadow them. For I mean, most decisions are reversible. And there are ways to like reduce risk. No doubt. And 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 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 'cause you're unhappy. Start figuring out 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 found his fascination and he like followed it root like pretty ruthlessly and became Bob Dylan. And then you, 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 it. But then like, I know you've worked with Travis Kalmick, who's like a pretty wild guy. The people who in order to like do these exercises of finding your passion, you sort of have to be like a roots of 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 his coaches and players and become coaches. So even if this prickly guy, you see throwing the chair is not the one that developed all these humans, 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 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 where 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 say follow your passion, what I really wanna tell people, I'm like, basically this sounds like crew, 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 flexibility. And so you move from one town to another, a lot of the people in the book do that. You might be half to stay in a job because you've built the 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 say? - I mean, we were getting paid decent money. Like for, this was when you were 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 under water. - I know people that make seven figures a year, $1 million a year and will literally have $0 in safe. - 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'd 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 said to go away as much cash while keeping expenses low. And it was like, anything above six months, that's like your FU number. Meaning you could like go and like try and experiment. - It gave 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 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 do with it. - What do you do with the money once you've already made it? This is a question, Sean and I asked our successful guests all the time and the reason we ask it is because if you are successful, if you do have a little bit of money, information on how to spend or invest your money, it's actually really hard to come by. And I know this because inside of Hampton, which is my community of founders, people ask this question all the time. People have made 10 or 50 million dollars. How do you spend it? How do you invest it? And so to help solve this problem and answer this question, I actually interviewed 80 plus founders, guys like Scott Galloway, Alex Ramose, Brian Johnson, people who are worth 50, 100, even billions of dollars. And we got them to reveal everything. So they're net worths, how much they pay themselves, they're monthly expenses, they're portfolio, things like that. And we turn these 80 interviews into one document. And I don't think you can find this type of information literally anywhere on the internet. And it's completely free. So if you want to see behind the net worth of people who are worth billions of dollars and their portfolios or expenses, everything, you go to joinhampton.com/reveal. Again, joinhampton.com/reveal. Check it out. (upbeat music) - The last night was special because I sat across from Jim Kramer and then next to him was Henry Bologgett who founded a business insider, just a lot of crazy people. When you knew these guys when they were younger, was it clear that you guys were all going to succeed or have you been surprised that someone has been as successful as they are? - Well, I think it goes back to our discussion on peer groups. Like connecting with, I've just always found. And I think I got more attuned to this the older I got. Like, having a big tent mentality. Like, have as many friends as you can try not to judge people too much, root for people to be successful when you can and it'll come back to you in space. I guess I've never been surprised that the people that end up in Silicon Valley and the middle of it all continue to move forward just because it attracts so many ambitious people. I haven't been radically surprised by anybody staying power. Keep in mind I'm 59 years old so I have the benefit of time to build that now. I had 25 years as a venture capitalist. But I think you were on the board of what's the moment you and Danny Meyer you're on the board to open table. That was like 20 years ago. Yes. It seems like you kind of like it was right up pretty early and yeah into investing right. It's kind of key in venture. What do you mean? Oh just to be in front of the wave or whatever rolls out like you can't can't be late. With AI going on right now is this just this remind you of a different period in venture? I've never seen it quite like this. Really? Really? I was one thing I think throughout my career ventures only got more competitive and now today it's you know as I'm hanging up my boots and watching the next generation it's even more competitive and the burn rates that the VCs are comfortable experimenting with are bigger and bigger than ever. Like I thought our two billion a year burn rate Uber was pretty frightening. Open AI is burning way more than that. How much are burning? I've seen different number. I don't have access to their financials but Uber was losing two billion a year. Yeah but opening as it like eight or ten. What did it was it make you feel when your company's losing two billion dollars 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 I sleep much. There was a piece of it that was that that I think is as the venture industry gets more industrialized was a problem which was I think the lift investors knew that they had to keep funding liquidity and for all 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 that. 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 Uber and all these companies would give like the craziest referrals so like I've ever like giving my referral to everywhere like no I drive on Uber for I ride on Uber for free. I get it and and and it wasn't until lift 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 and where Uber was able to then take advantage of the network effect and being larger and and now spits off well north to 10 billion a year and free cash flow. That's how big it is now that's insane. Did you did 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 an apartment but the dar 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 have it. Oh okay. Yeah. What did you say? I wrote 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 sub stack where they're like AIs going to make the economy worse? Do you see a one blog post like brought down? It's pretty amazing. That's crazy right? Yes. Did your blog ever do that? Not not if that scale no. Yeah that was that was insane. Yeah it's insane. There's a lot of fear out there just remember 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 it's 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 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 Deller so he knows Barry and all that but Rich has this remarkable ability to be top 1% out as a product technology disruptor but also as a leader. That thing we're talking about before and I usually see people tilt one degree or the other and not both and he's this rare person that did does it on both. And so I frequently lean on him for advice. You have an example of like the 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. 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 then 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's not easy to do and I'm back on the border 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 you also say that like Jeff Bezos is one of those guys who does two things really well. It would be a good exercise for someone to kind of write down the leadership techniques of Jeff Bezos because Amazon remained innovative after it got to like a hundred thousand 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. He's seeing him 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 grow how they're able to lead. A lot of these people who are these like kind of the titans of industry that you know do you think that there's any correlation or reverse correlation of 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 is the good-foss man and I think he really loves life. I'm just saying that I don't think there's a correlation. I mean I every chance I get if Toby from Shopify does a podcast or something I'm eating it out and I find his attitude on leadership in life to be lighthearted. 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 has something wise about him. Yeah there's something wise about him. Do you see where he's 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 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 can't like nerd with him like you know Darmash at HubSpot. I have men but I don't know him. He's kind of the same thing where they he's like there's these groups of group of guys who are like very like you think of a leader sometimes you think of like a Napoleon like Ra Ra like Ra people out 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 are there 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 they're all listed in here there's 35 books listed at the back of the book so I but 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 it 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 like if if if there's something you're just super passionate about and even if it's a hobby you might be surprised there might be there might be a way to make a career around what's a lot easier now the internet it's this but by the way I would love to close with this point that you just made a If you're a, 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 your high agency, I think that's the word you used earlier, AI is like a jetpack. 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 you ever could before. If you have agency and a direction you're headed in, AI is going to make things way better. 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 have met so many," what I would call, like SMB founders or regional founders running businesses that are laundromats or storage facilities and they've discovered all the things they can do with AI. Now they feel superhuman. I'll wrap up with the story. You'll dig this. My mother-in-law, her name is Smithy. She came here to America from Haiti at like 14 years old, didn't speak English, married my father-in-law, Jeff owned a moving company. Smithy was a state homeowner for a long time. The kids grew up and she was like, "I'm lost. I need to do something. What's going on?" So about five 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 or whatever. Sounds good. I was like, "There's this thing called Shopify. Let's just start there." It's been five years since that. She now has a pillow company that sells over a million dollars a year in pillows. She has a warehouse in New Jersey with five full-time employees selling pillows. She was just on the pod. She uses AI all day to how do I buy an ad and chat to me like teaches her or she's like, "How do I, whatever, it's YouTube and chat to me like telling her what to do." She didn't know what E-commerce, she didn't know what that meant. She basically just knew what Google was and that was it. She in her late 50s started a E-commerce business that does millions of dollars a year. That's amazing. Crazy, right? Yeah, no, but it's never been a better time to propel yourself forward if that's what you're prepared to do. Well, thank you for doing this brother. All right. All right, God love. Yeah. ♪ I feel like I could rule the world ♪ ♪ I know I could be what I want to ♪ ♪ I put my all in it like no days all ♪ ♪ On a road let's travel never looking back ♪ If you made it this far, then you're going to love what I'm about to tell you. So there's this amazing entrepreneur, his name's Neil Patel. He's been on MFM. He's one of our favorite guests and he has a podcast that's called Marketing School and it's brought to you by the HubSpot podcast network. Marketing school brings you daily actionable digital marketing lessons learned from years and years of being in the trenches. They have over a hundred million downloads and over 2,500 episodes. Marketing school gives you bite size marketing wisdom that you can implement immediately whether you have a new website or you already have this huge established business, you're going to learn about the latest SEO content marketing, social media, email marketing, conversion optimization and general online marketing strategies that work today. You can get marketing school wherever you get your podcasts.