Why You Shouldn't Chase Your Passion: Bill Gurley on the Delusional Factor Every Outlier Needs and How to Find a Mentor

I had Larry and Sergey of Google present to our partnership when there were 25 employees. So at the very beginning, and we failed to lay chase. So they presented, left, and we didn't try and close that deal. And two of the best venture capitalists in the world, John Doerr and Mike Moritz, ended up doing that deal. And I can remember at the time there were a couple of no's in our mental models. Biggest mistake of my career.

Welcome to The Carey Nieuwhof Leadership Podcast. Hey, I am so excited to bring you something a little bit different today. You know, while we're focused on helping leaders in the church space—that's people who work at churches, volunteer, sit on boards, invest, that kind of thing—today, I'm going to talk to Bill Gurley. He is the man behind Uber, Snapchat, Twitter. What else? OpenTable, Zillow. What did he do? Well, he invested in these companies when they were very, very early stage. And my goodness, this is a fascinating conversation. We talk about why you, if you're thinking about what you should do with your life, shouldn't chase your passion. You gotta chase something else instead. The delusional factor every outlier needs—I find that fascinating, right?

If you're a church planter or you wanna reinvent a church, are you delusional? Maybe you need to be. And how to actually find your dream job. So welcome to the podcast. Really glad you joined us. I want this to be a very good investment of basically 90 minutes for this one. It could have gone much longer. Bill is just fascinating. He is a general partner at Benchmark, a leading venture capital firm in Silicon Valley. Over his investment career, he has invested in and served on the board of such companies as Nextdoor, OpenTable, Stitch Fix, Uber, and Zillow. For more than two decades, he's written about technology and other subjects on his very popular blog, Above the Crowd, and on his social media accounts.

He's very active on X. And now I think you're going to enjoy this conversation as much as I do. My conversation with Bill Gurley. Well, Bill, I've appreciated your work as an outsider for a while now. I think I first heard about you on Tim Ferriss's show years ago. And so I'm really delighted to have this conversation with you. We're going to talk career, going to talk AI, going to talk about everything. Welcome.

Thanks for having me on.

Yeah. So, you know, I want to go back to the genesis of your career. You played some basketball. You're a tall guy. Is it 6'9"? Is the internet correct on that? No, no.

I'm getting older. Start going the other direction.

Was 6'9". Yeah, I know. I'm afraid to measure myself at this stage. I was 6'2", but I don't know whether I'm still hanging in there or not. But you started at Compaq, which is a company a lot of listeners wouldn't even really remember, but I remember it. I'm of a certain vintage. And then you moved into Wall Street research before becoming a VC. And now you're reinventing yourself again—VC, venture capitalist. A lot of people would have been very comfortable staying at Compaq.

Would have been like, 'Wow, I got a career here.'

And even if, you know, the company didn't survive, you can move to Intel, you can move to NVIDIA. I mean, you could be retired or, you know, CEO at this point. So what made you decide early on that you wanted to make a jump?

Well, it's interesting. In talking through this, I wrote this book not about myself very intentionally, which we can get to later. But when I've been talking to people about the book, this comes up a lot. And I've actually developed a bit of a heuristic on what happened in those two situations that isn't in the book. I kind of wish maybe it was. But in both cases, I was about two to three years into that part of my career. So I was an engineer, a computer science engineer at Compaq, working on products that were shipping, desktop computers. And I'll tell you about the other job in a minute. I had this moment where I just stopped and reflected and asked myself the question, "Is this what I want to be doing for the next 30 years?"

And I don't know why I was able to ask myself that question, but it was provocative in my mind and very clear, the answer. And what happened in that case, my brain goes, you know, all the time in every direction. And, you know, people might call it ADD. I'm very curious about a broad variety of things. And when the third project I was working on started at Compaq, it looked a lot like the second one and a lot like the first one. And in my brain, and maybe that's what allowed me to do the 30-year thing, it was going to be monotonous. And so I needed something else. And there was another heuristic that could be borrowed from that. I had started to develop other interests. So I had read this book, One Up on Wall Street by Peter Lynch.

I was beginning to buy stocks. And so my spare time outside the office was doing other things, which I think is a hint. Like what it is you do in your spare time might be that thing that you're ultimately most curious about. And so I went to business school. Um, I, I, I toyed with the idea of venture capital there, like it came into my brain. Um, John Doerr, the famous venture capitalist, was on the Compaq board. Compaq was a very hot, um, high-tech company, even though it was in Houston. It was a bit of an outlier that way from location, but it was big and it went public. It was worth a lot, um. And that didn't look like there was a path from business school at University of Texas into VC. And so I took a different route.

I had become a bit enamored reading about Wall Street analysts that get quoted all the time on their industry. And I went to New York. And that job was wonderful. I loved every minute of it. Like it gave me unbelievable access. But one day I was working—those, those early Wall Street jobs, you're working 7 a.m. to 9 or 10 p.m. And I was at the office and it was like 8 p.m. And I walked around and there were four corner offices on this square building in New York. And they were all the most senior analysts. And I walked around the building and I stopped at each one of their offices. And that moment gave me that same reflection game where I was saying to myself, "Do I want to be in this corner office 30 years from now? Do I want, like, my time on this earth to be tied into being the best Wall Street analyst I can possibly be?" And the answer came up no again.

Even though I'd been quite successful. And so I started looking to pivot out and found my way to Silicon Valley and to be a venture capitalist where I was quite comfortable with the question there. It never came up. I never pondered as a VC, "Is this what you want to be doing 25, 30 years from now?" And I had a remarkably fulfilling career. It was successful also, but I loved the everyday work product of it. So that's the journey.

For those of us who don't really understand, we've all heard about venture capital, but might not understand it. I think one of the reasons that made ministry so interesting to me is it's a different message every week. There's a common set of challenges. That's the thing I love about now. We're 800 episodes into this podcast. Every guest is different. Really fascinating to me. And, you know, I'm fortunate I get to say who comes on the show and who doesn't come on the show. So that's a lot of fun. We get a lot of pitches. I get to write a different book every few years and it's like, ah, this one's really got me right now. What is it about venture capital that kept your interest for—how many years was that, Bill?

Was that 20, 25?

Yeah, I think that diversity is a big part of it. And I think I've come to realize that there are a lot of people that kind of favor diversity and breadth over everything else. And I think they're the people that end up in—I think there are several jobs that yield to that. I think everything from a lawyer to a consultant to an investment banker, like these service-type jobs, you're out meeting with different clients all the time. And so you just end up with more breadth. You trade off for that a lack of detail and maybe a lack of ownership. Like some people really want to be in the weeds and in control. And these jobs are far from that. And so getting in touch with what motivates you. And look, thank God there are people that want to be in the weeds like a founder, that want to lead 500 people, and therefore you have CEOs.

Because the venture capital job wouldn't work if those other people weren't great at those roles.

Yeah, so you're basically choosing projects to fund, right? Startups, etc.?

Yeah, and in addition to diversity, one of the other amazing things about venture is the edge always keeps moving. And so over those 25 years, you know, the type of companies today, which are all AI companies, are very different from the type of companies that I funded when I first got in. And that—you have to constantly evolve with whatever is new and innovative on the edge, which is another form of learning. So I think that was another part of it is I just love the idea that there's constant change. It's very dynamic. You have to learn. And if everything's moving that way and you can figure things out, you get rewarded for it. And so it's a complex puzzle that way.

Yeah, you know, it's interesting. I'm sure you picked some losers over time, but you picked a couple of winners more than your share. So, you know, you were involved in the Amazon IPO. You invested in companies like Uber and Zillow, I mean, which have all gone on to become household names and household realities. I'd love to know, how did you—and again, feel free to talk about the losses, but it is interesting—you had a pretty good track record as a venture capitalist. What were you looking for and how did you learn to spot a winner?

Well, I mean, there's a lot of losers, by the way. And one thing about venture capital is that the outsized outcomes that come with the winners make up for lots and lots of losers. Because when they work really well, you get 1,000 or even 10,000 times your money. So it's a weird game of home runs. What I look for—I stumbled upon this article in 1996 by Brian Arthur about increasing returns, which was in Harvard Business Review. And it's really another word people use to describe that phenomenon as network effects. But once the internet came along, there were scenarios where if a company could get started, the function of being bigger would actually serve to their benefit. And so rather than becoming slower, you actually became faster.

And OpenTable was another one of my investments and probably one of the first ones.

Oh, yeah, OpenTable. My goodness, I use that every time we go out.

Yeah, so we funded that when there were three restaurants. And... what we realized and the bet we made at the time was, if we can make it successful, then everyone will have to be on the same network. And so you have this network effect. And the more restaurants that are on it, the more the consumer will want to use it. And the more the consumer wants to use it, the more the other restaurants will need to be on it. And so that's that network effect. And so a big part of my career was understanding that concept early and looking for scenarios where that kind of function would play out in the way the market worked. I mean, the other things you hear, if you talk to 10 VCs, you're going to get a lot of common thoughts.

You're going to hear about great founders that are tenacious, won't stop, can't stop. Super talented. They need to be really good at sales. I don't think people understand, but the founder is selling for more money, is selling for biz dev deals, is selling customers, is recruiting, which is selling. So they're just selling all the time. And they have to be great at it. So that's something you're evaluating very quickly early on when you're talking to a founder. And then another big one is... and this kind of goes across our entire portfolio. Most startups that are successful have come up with some advantaged path to market. So they've figured out some interesting way to get customers faster. And for enterprise or B2B companies, that can be very different from B2C.

But they usually have come up with some idea of how to get their sales momentum faster.

Okay, this is interesting. In addition to the church leaders listening, we've got people in the business world who tend to fund the churches, who sit on the board, who are advisors to pastors. And some of them, you know, part of church plants. Some of them, honestly, are part of some of the biggest churches in the country, right? So I want to take you back to OpenTable. They had three restaurants signed up. And for those of you who may have never used it, it's a very—what, North America? Global?

No, it's global. One of my proudest moments: my wife and I walked into a restaurant in Bali and saw it on the desk there at the front. And I was like, 'Wow, this thing really did it.'

Really took off. So it's a restaurant reservation system. Basically, I want to have dinner in Atlanta. What's open tonight? Can I find an open table? And like I said, I've used it for years and years and years. But when you're looking at those co-founders or the founder, and they have three clients—you listed some of the things. But if you could take us into a case study, because some of the people listening are going to fund church plants. And they're like, 'Okay, is this... person, is this couple, the kind of person I'm going to hitch my wagon to, the kind of person that we're going to give meaningful money to to get this church off the ground, right?' Church starts. So I'd love to know the thinking you had.

You know, the thing that—and you're asking me to wade into a category I've never thought about professionally, but I'll do it. I would think this go-to-market advantage thing would be more what you'd be looking for. So, you know, I look at the... I look at the entrepreneurs that hustle the most, and especially when you're dealing with consumers, and they know how to leverage all these new technologies that are out there. And this would be true of a podcaster too, obviously. But how to leverage TikTok, Instagram Reels, Twitter, whatever. I would think that that's an area where you could really leverage, move the needle, and grow much faster if you had awareness and understood what best practice was in those areas.

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Yeah, I think you're right. I think part of it, it's like business. Many church plants fail in the first three years. Not because of vision, not because of faith, not because of hope. They don't make it. But then there are some that just go astronomical, right? That go really, really big.

And my guess is those had those skills I just described.

Yeah, exactly, exactly. And the investors behind them probably saw that, right? And like you say, you fund a few or you give to a few and they don't really pan out. And then you give to some and it just, you don't get an ROI financially if you're doing that with a church plant. But you get one in terms of, 'Wow, we made this happen. Look at it go.' For a young leader listening, whether they're planting a church or starting a company... how would you describe the difference between healthy risk and reckless risk? I mean, every entrepreneur takes a risk. A lot of them kind of go under, right? So what is it like? How do you know you're not delusional when you're like, we're going to take over the world and we're going to be in every restaurant in the world?

And, you know, like some of that's delusional and then sometimes it happens.

I think it's an extremely provocative question, Carey, and the reality is we often don't know. And one thing we've learned the hard way is it's very hard to pass on the one that seems... a little bit crazy. Like, you know, and you go back to that classic Steve Jobs video, like the Apple ad about the crazy ones, you know, and it's just true. Like, there's a bit of self-delusion that may be required to attack the hill, you know, that if you don't have it, you know, I think the vast majority of people would never attack the hill because it's too daunting and everything looks impossible. And there's a certain amount of naiveté there. And by the way, this is one of the reasons I think that many founders are under 25, like even of the ones that create the biggest companies in Silicon Valley.

They don't know what they don't know, and that can be helpful. And look, we're talking about the ones that make it. For every one of those, there might be nine that fail or more. And so the problem is... there's no function that says find the crazy ones and give them money. That won't work either. But I can't tell you how many times our partners and I discussed this particular thing, which is like you have to... you got to try and make yourself comfortable with the ones that are a little bit out there because they are the ones that are going to try new things. They are the ones that are going to never give up. And the surface area is always moving. So that type of innovation, if it hits right, could lead to success.

Yeah, you know, I think back in the early days of my ministry, which is three decades ago, I was 30 when I started, not 25, but it was three dying congregations and we started to grow. And then I'm like, "Well, let's just amalgamate them. They're only five minutes apart. Wasn't true 100 years ago when there was only horse and buggy, but we can do this." And like everyone looked at me like I was crazy, but there was something inside me that's like, "Nah, this is going to work. This is going to work. This is going to work." I look back on that now. It did work, by the way. Good, congrats.

I look back on that now and I'm like, "What was I thinking?" Because the people who try that, it never works.

But there is that kind of youthful optimism that makes a big difference, I think, that maybe me at this stage would be like, "Well, I don't know. I mean, I read the data on that." So speak to it. Go ahead and comment on that.

I think navigating life is a lot about building mental models in your brain that become rules on how you navigate the world. And a young person is building up their... you know, their toolkit full of these mental models. I think when you get older, you have so many of them in there that it becomes somewhat rigid and it's very easy to get to a no on almost anything. And like, you just become conservative through the process. And so, yeah, like I said, you know, the, the, the younger person is going to take more risk and there's going to be a higher failure rate, but some of them are going to, it's going to pop and it's going to work. And that's how it goes.

Did you find—and I'm not asking this in a critical way at all, I'm just out of curiosity—did you find as you got more seasoned in venture capital, you know, 20 years in, that your mental models started to interfere with your ability to pick a winner or take more risk? Or how did that work for you?

Yeah, I think it does. Our particular firm, Benchmark, has a very unique structure, which is an equal partnership structure. Right, right. One of the things that we've done from the history of the firm is routinely bring in the next partner. And I think last time we ran the data, the average age of that incremental partner is 29. And so we're intentionally injecting someone younger into the partnership to be part of the voting process. You know, the day they show up, they get an equal vote on new deals. And I think it's precisely because we're concerned about what you just said. And so you want to... And in venture, it really matters because the edge is constantly moving. So, you know, things like TikTok, Instagram, Twitter.

We were an investor in Snapchat, Instagram, and Twitter. And you don't see those things if you don't... You know, I remember once when we were looking at Snapchat, we talked to one of our kids and... I forget, one of the partners' child said to one of our partners, "Instagram to us looks like LinkedIn to you." And what they were saying is it's all out there and in the public. And Snapchat had this thing where the messages disappeared. And that thing landed in our brain in a really interesting way. And we funded Snapchat right at about that moment. But it kind of gave us permission in hearing that. But once again, that was a young person's view of where the digital world had moved. And what is that, like a six-month-old discovery by these young kids?

It's right on the edge. And so, yeah, you need that. I mean, that mental model has to be super fresh.

So if I got this right, you systematically, like systemically, challenge your mental models by making sure that you had young investors at the table, young people speaking into it with not just a voice, but a vote—like they were making decisions with you.

And the other thing I would say is venture is this kind of world where, you know, for the next deal, your mental model, some of it's going to go off and say yes, and some of it's going to say no. And you have to learn that somewhere along the way, you're going to ignore an old rule and let it go. I learned this really the hard way. Worst story as a venture capitalist: I had Larry and Sergey of Google present to our partnership when there were 25 employees. So at the very beginning, and we failed to chase. So they presented, left, and we didn't try and close that deal. And two of the best venture capitalists in the world, John Doerr and Mike Moritz, ended up doing that deal. And I can remember at the time, there were a couple of noes in our mental models.

So Yahoo had fallen from 82 to 10 as a public company. Excite was going bankrupt. So other search companies were doing poorly. So that's just in your brain. Larry and Sergey were both PhD students who both wanted to be co-CEOs. Up until that moment... If you back PhD students who want to be co-CEOs, you'd probably fail. Like that was just, they're not the type of people that are great entrepreneurs. And so here, there's two, just two examples where your brain's saying, and pumping the brakes. Biggest mistake of my career, like right there.

And so that's— Passing on Google.

Yeah, well, I always use the word 'failed to chase' because passing makes it sound like they were begging me and I said no. We stopped pursuing, you know, but it was still the biggest mistake of my career.

Man, you know what? Anything else on mental model changes in you? Because I know you said, 'Hey, I don't know a whole lot about church world,' which is great. That's why we're having this conversation. I believe, as I think you do, we learn best from disciplines outside our field, right? That's why I'm having you on this podcast. But what every church leader needs to do is just pause right now, go back and play that last 10 minutes on mental models over and over and over again until you make some changes in your church. I mean, we have an aging-out problem in the church that you wouldn't believe how bad it is, Bill. The average senior pastor is 58, doesn't have confidence in the next generation.

I mean, without knowing it, you are speaking right into one of the central problems that most leaders are facing right now.

One thing, when we get into the book, I'd like to come back to this. Because I think the peer—there's a chapter in the book called Embrace Your Peers. And I think there may be an opportunity for the problem you're talking about right there.

Okay. Well, why don't we dive into the book? Like I said, it's, in my view—not that I've read them all, but hands down—the best career advice book I've ever read. And particularly, I think it's helpful for the next generation. I have kids in their 30s. They're both gainfully employed right now. But when I think about what their future is going to look like in an AI world, yeah, I think you just have so much good advice. And like you, I chased a number of different careers, not really knowing what I was doing—calling, career, et cetera—and ended up reinventing myself three, four, five times in the course of my life. For a Gen Xer, that was a little bit of an outlier. Yeah. But it's pretty normative now.

So I want you to think a little bit about... Tell us, maybe we'll just start here because I do want to get into the book. And normally this is not a bookcast, but it's just so good. We've got to talk about that. Why did you write the book? Like, this is another career departure for you, right? You're wrapping up VC and moving into this field.

Yeah. And look, I think I'm going to go do something different after this. The book may be a one-time shot, but I was a blogger even before it was called blogging. I had a fax newsletter when I was on Wall Street, and it became a part of my career. And so in writing these pieces that would be read in the industry, you know, first of all, that was one way that I got distribution. So I talked earlier about startups having advantage distribution techniques, putting content out there created my brand, it created contacts and networking. It is a way to promote yourself. But through doing that for years and years and years, I had kind of built this framework in my mind where if I saw something interesting, I would jot down some notes.

And then if I went back to it, I would add to it. And I always had these working blog posts that many of them never made it out, but it was just a way of me to store ideas and notes. And I was finishing—I was at a point in my career, I was reading a bunch of biographies, and I read this third one, and I all of a sudden in my mind saw these parallels, going back to mental models, between this biography and two others that were in widely different fields. And I just immediately wrote it down. I started jotting down notes. And I was so happy with the way that the notes laid out that I said to myself, one day I'd love to give this as a speech maybe to a group of students. And so the opportunity came up where I went back to the MBA program where I started at University of Texas and I gave the speech that I had always wanted to give from those notes.

And they ended up posting it online. A few people noticed, one of which was James Clear, the author of Atomic Habits, who reposted it on his website. And people started prodding me, "Hey, you should make this a book." I don't think I could have put the time into it until I started to retire from venture. You know, the time that I really wanted to, if I was going to do a book, I wanted to put in the, the, the, you know, I just want it to be the best it could possibly be. Like if I'm going to do it, 'cause I've never done a book before. And most people expected me to do a book on venture or tech or, or investing because that's what I've, what I've done my whole life. But somewhere between deciding, okay, I'm finally going to do this thing, I'm going to do this book people have been pushing me to do, I became super excited about doing this book versus one of those others.

In fact, I almost had a negative emotion to going and doing a book on VC. There's several books on VC. But the bigger issue is, those books, if I had done them, their impact is going to be limited to some people in that field or whatever. This book has the opportunity, I hope, to have a much broader impact and touch a lot more people. I was also motivated by this book. I don't know if you've read it, From Strength to Strength by Arthur Brooks. Oh.

Love it. We've had Arthur on a couple times on the show.

Yeah, and he wrote this book literally about... I'm 59. I think the book is written for people that are in their late 50s that are finishing a career and saying, "What do you want to do with the rest of your time on this planet?" And it really spoke to me. That book really spoke to me and was a real push in the back to do this book. And Arthur talks a lot about... At this point in your life, giving back and helping others is going to be way more rewarding than anything else that you could possibly do. And so it really spoke to me. It was a big part of why. And so that's how I ended up in this place and with this book is through that process.

Well, it's really interesting and a bit counterintuitive. I mean, a lot of it resonates, but one of the premises that you attack, sort of the big premise that you attack in the book, is you reject the idea that passion should drive us. I mean, you know, it's that old adage, you know, "If you really love what you do, you'll never work another day in your life," you know, "Chase your passion," that kind of thing. What do you recommend instead, and why?

The reason I wrote that that way is I think the word "passion" has become cliche-ish and a bit overused. And because it's been overused, it makes it quick for people to reject. And I was watching this graduation speech that Jerry Seinfeld gave at Duke where he said—first of all, he was very dismissive of the word "passion," but then he used the word "fascination." And in the book, we use the phrase "chase your curiosity." And it's really trying to get in touch with: what is the thing that you're going to be willing to learn about constantly? So this is continuous learning, even if no one made you do it. And earlier, when I was telling my own story, I told you I was learning about stocks when I was not at work.

And so, what topic is so interesting to you that you study it for fun? And I think it's a high bar. And maybe there's a big part of the population that never has something like that, in which case this wouldn't apply. But if there is something that is so interesting to you that you would study it in your spare time, I would encourage you to consider maybe that's where you should have your career. Because you're going to spend a third of your life at work. And if you have that dimension where the learning is free, you are going to soar to the top of your field. Like, you're just going to outrun everybody. And if the learning is free—I use that phrase to mean it doesn't require, it doesn't suck energy from you—

it gives you energy. Like, if that's the case, if learning about this particular thing gives you energy, you're going to be wildly successful. I just have zero doubt, you know. And so that's the test. I think that we go back and forth between the first and second principle in the book of saying, you know, if you love it, then you need to learn all the time. And if learning all the time is tedious, go back to square one. Like, that's the wrong—you're in the wrong place, you know.

You know, it resonated with me so deeply because while I was in ministry, I mean, I read the theology I needed to read for 20 years, but it was really the leadership stuff that I found fascinating. You know, I'm like, "Gosh, I'm reading leadership books. I'm reading business books. I'm reading books by non-Christians. I'm trying to figure out how that integrates into what we're leading inside the church." And lo and behold, for the last decade, guess what I've been doing, Bill? That's what I've been doing, right? Trying to integrate all of these learnings from different fields. We've had James Clear on the podcast. We've had Arthur Brooks on the podcast. And so many others, just trying to go like—and again, you know, the secret is, and I've talked to comedians who would say the same thing:

"I would do this if I wasn't paid to do it." Like, it's just so much fun.

Yeah, that's the thing. And I've said that about my venture job. By the way, you started by saying, like, why did I write the book? And there's a story I discovered that's also Jerry Seinfeld. So he's living in New York. He doesn't really know what he wants to do with his life. And he reads this book. It's called The Last Laugh. And it's a profile of, like, 14 comedians. I don't know if anyone needs to read it. But for him, it... it brought to life that, you know, here's 14 people who make money doing standup and it's a real job. And like this was disinhibiting and allowed him to have permission to think in his brain, oh wait, I could do this for a living, you know? And what my big hope for the book is that it does what this book did for Jerry, for a whole bunch of people in a whole bunch of fields.

Grant them permission to go chase that thing that is so easy for them to learn about, just as you described with what you do.

Well, if you're open to it, do you want to tell the story of Danny Meyer? I mean, he's someone that I'm fascinated with. Will Guidara has been on the podcast a few times. Will studied under Danny. And it's one of those things that it was just, I think it's an opening story in the book, but it's just... so fascinating to see what he was going to do with his life and how he ended up becoming the most successful.

For your listeners, Danny's one of the top restaurateurs in the world. He's built 10 or more very successful restaurants in Manhattan. And he also created Shake Shack, which he did a little bit later in his life. But... yeah, Danny was a salesperson who was doing extremely well in his field. He was selling, I think, those devices that they attach to clothes at the retail stores when you walk out the door.

So you can't steal them; they bleed ink or whatever.

And he was making something like 200k a year back in, like, the '80s. So, that's a lot of money. But he wasn't satisfied. He wasn't happy doing it. And so, he had decided he was going to take the LSAT and go to law school. And he's out to dinner with his uncle the night before he's supposed to take the test—or he did take the test, but the night before he takes the test—and his uncle said, 'What are you doing?' And Danny's like, 'What do you mean? What am I doing?' He says, 'You know you're supposed to start a restaurant. That's all you ever talk about.' And what his uncle—and most of us don't have an uncle that's willing to do that, by the way. In fact, they'd be afraid that your parents are going to pound him over the head, which is part of what I want to kind of help us break away from is this kind of safe,

shepherding of young adults. I think it, unfortunately, has led to the wrong outcome. But anyway, Danny's uncle was provocative in a way that really spoke to Danny. And the thing about Danny—and we go through this in detail in the book—all of his spare time was enjoying restaurants and studying restaurants at a level that's beyond probably any friend that you have, like taking notes about decor and different menu presentations, fonts on menus, like things like that. He was noticing as a fan of restaurants, not as an employee in one. And once his uncle said this to him, and it just flipped a bit in his head, and he quit that job. Luckily, that job had provided a lot of compensation. Danny took his next job at less than one-tenth of that salary.

Not planning to be in it forever, but knowing he had to start on the bottom rung. And almost every one of the stories that we picked for the book, we find people that had initial intent and started on the bottom rung. That was a big part of it for us because I want other people to understand that it's possible just for those two things to be true: 'I've decided I'm going to go do this new career and I've never done it before,' and, 'I'm going to start at the very bottom.'

And it pays nothing. So, anybody in ministry would be very familiar with that trajectory.

But he took it to learn. And then he took it to another level where, after he absorbed everything he could there—and by the way, I think he took two different low-level courses at whatever trade school, like one on running a restaurant, one on wine. And then he launched himself through a bunch of connections his family had through Europe as—there's a term in the industry called a stage, which basically means working for free. And he rotated through a whole bunch of restaurants in Europe working for free, taking copious notes, just crazy amounts of notes, and then came back to America and eventually launched Union Square Cafe, which has been a long-running, you know, top restaurant in New York.

In fact, we're doing the book launch there on February 23rd.

Really, my wife and I, we went there last year, having done a bit of research into Danny Meyer and had lunch at some of his restaurants. And one of them was Union Square Cafe. Like, just absolutely fascinating story. But that's that whole thing of downward mobility, right? I left success, which was not satisfying. And this is a guy, as you say, who's walking into restaurants and noticing things nobody, perhaps not even the restaurateur, would have noticed. But he's just interested in the art and craft of cooking, owning restaurants, etc., and uses up his life savings, and now he's a household name in the industry.

By the way, I think that's such a great word, Carey: craft. If you think of... I suspect there are fields and industries and careers where you look at someone and you say, "Oh, that guy's an engineer, that guy's an accountant," but you don't consider what they're doing a craft. But I guarantee you, whoever's best at it, you know, in that field, they approach it that way. Like, they think of it that way. And I think it's another great test of whether this is something that really is your dream job and what you should be doing with your life is if you think of it as a craft. Like, you know, it's almost as an artisan. Like, "I need to figure out how to be the best I can possibly be at this thing I'm going to go do."

And the other thing I think the word "craft" elicits is a bit of respect, like respect for the art. Like, you know, and one of the things that I harp on is, is you should really study the history of whatever it is you're going to go do. And one of the reasons that that means so much to me is, one, I think it's a test. Like, if studying the history of the field is rote and boring to you, then I don't know if you appreciate the craft enough, really. But two, it just... It gives you such great walk-around credentials to have the knowledge of the elders in your brain. And both from the content—valuable to have, like it's really good to know the bedrock—but also when you interact with other people and they realize that you have that knowledge, it's very differentiating as to who you are.

Exactly, that you have the potential to be a master at what you do.

We have a great little scene in the book I'll hit on real quick where they're having a world chess tournament and they take a break and do a history trivia quiz, and Magnus Carlsen wins the trivia contest—who's the best chess player of all time. And just the fact that he won that is not surprising to me.

He mastered the craft.

Yeah.

You know, Bill, I don't know whether you have this or not, and I don't think this was explicitly in the book, but like when you're describing the craft—I'm not a brain scientist, but I'm really enjoying this conversation. I had high hopes for this conversation. You're telling me things I wasn't expecting. I feel like when I have a conversation like this—and I want to get better and better at the art of interviewing, I really do—but when an interview is going well, there are moments where it feels like all the dopamine receptors in my brain light up. I just got off the third draft of of my new book, which comes out later this year. You've been through book writing. And I mean, book writing is hard, but like it reaches a point at which it almost—

it's not writing itself, but it's like—I don't know how to describe it—it's just like you're in that flow state. You're in that—you're in that flow state, and you're just doing whatever, whatever athletes do. And you also have an athletic background. I have in writing, I have in podcasting, I have in this work. Is that some kind of clue for young leaders listening? It's like, when do you get in flow state? When are you like, you lose track of time? It's like, "How—how's three hours gone by? I was studying restaurants. I was reading the history of—I was doing this."

Yeah, I mean, obviously there's a book titled *Flow*, and there's other people that have worked on that particular idea quite a bit. But yes, I think that when you are doing the thing that you love, you enter the flow state quite frequently. And when I say "learning for free," I think that's synonymous with what you're talking about because it doesn't seem like drudgery. You lose track of time. It is giving you dopamine just to learn about the field or to think about the field or to study the field. And if you're fortunate enough to find that place, I think you become like a—you become this kind of—it's like a superpower. You become this kind of—this athlete in that field that would be very hard to compete with.

You know, like if you just—some people like to give the career, some people, I think they're just being provocative, but there's some very famous people that, that give this pitch: "Don't do what you love. Do what you're really good at." And there's two problems with that, but one of them gets to this point. If I'm in a field where I'm just good at it and the human next to me is good at it and has this adoration for constant learning in the field, they're going to outrun you. Like, they're just going to outrun you. And if they get flow while they're doing it and you don't, they're going to outrun you. And so that's the danger of that approach, I think. Angela Duckworth, who wrote the famous book *Grit*,

did a podcast like 10 years after she wrote it. So she argued in *Grit*, you need perseverance and passion. And in this podcast, she said, "I probably shouldn't have done it 50/50. I should have put more on passion than perseverance." And her belief now is that we've taught, especially in some areas, you know, prep schools and whatnot, we've taught these young adults to grind—like, just to grind obsessively—and they get good at it. But if they don't have this love with the topic that they're working on, that eventually becomes burnout. Like, they just eventually wear out. And so, yeah, if you're getting into flow, you're getting free energy from doing this thing. And it really, it's just an unlock.

It's like such a powerful unlock.

Danny went out and found some mentors in Europe, you said, through some family connections. That's an FAQ on this podcast and in the work I do with leaders because we have a lot of young leaders. And it's like, "How do I find a mentor?"

How do I find a mentor? You know, if I'm getting into venture capital, how do I get an hour with Bill Gurley?

Like, please explain that to me. What are your thoughts on finding mentors and how does that work?

Yeah, we have a chapter in the book on mentors, and I divide it into two halves. And, you know, when Danny first sat down and said, 'Okay, I'm going to go do this,' he made a list of what I call aspirational mentors. So he didn't beg them. Like, one of them was Wolfgang Puck. In the book, I think we list all of them, but like... there were 10 people that were at the top of the restaurant industry. Some of them were changing the restaurant industry, so it wasn't just the most historic. But there were 10 that were important. And he made a little poster of them. He studied each of them. He wrote notes on each of them. And I think one mistake people make about mentors is they immediately think, 'Oh, I'm supposed to cold call the best and the brightest in the world.'

I'm going to go from... being like bottom of the totem pole to Wolfgang Puck overnight.

Yeah, you can't do that. And I love this notion of aspirational because you can learn from all those people and you can study them and it'll be very helpful to you. And... very likely, if you're winning, you're going to meet one of them one day, and it's going to be awesome, and you're going to know all about them, and your ability to interact with them at that point in time is going to be so advantaged by the fact that you had studied them this whole time. But anyway, aspirational mentors are afar. They're people you study. In today's world, with podcasts and YouTube and AI, you can study these people like... like 10 to 100 times easier than it would have been 20 years ago. So it's just unbelievable access to make that work for you.

So that's the first half. The second half, for real in-person mentors, I think just don't get greedy. Like, there are people that are two levels down from the top who no one's asking to be a mentor that knows a lot more than you do if you're on the bottom rung. And so I think it's important to find people that are going to have the time to take it seriously that can still help you. And by the way, you can get multiple mentors on different vectors of whatever it is you're trying to learn about. So you don't need this holistic person where you'd end up wasting a bunch of their time. You can get someone that's good at X and someone that's good at Y and someone that's good at Z. Um, but, but be more realistic as you start to climb, um, this ladder from the bottom rung and, and pick someone that's a couple of rungs above you rather than... Unfortunately, and once again, I think it's well-intended.

Most, when most people talk about mentors, the word's so heavy, it implies this guru that's basically inaccessible. So that doesn't really work.

Yeah, if you were to do—and I could not agree more with that advice. I mean, some of the guests on this podcast have been aspirational mentors for me, but I didn't start with them 11 years ago. You build up a reputation, you build up an audience, you get to know people, you get introductions, you cold call some people. And sometimes it works and sometimes it doesn't. But I think you hit, Bill, on something that's really different now: you can DM an aspirational mentor. I mean, theoretically, somebody could DM you. Email addresses, despite all the privacy attempts, are widely available on the internet. You can take some logical guesses and drop you a cold call email. What advice do you have for young leaders on that?

Like, don't jump up three levels. But let's say you had a chance to legit—you've done the hard work, you have a chance. I want to be in investing. I get a chance to pitch Bill Gurley on a coffee or whatever. What are some dos and don'ts?

Well, you combine two things there. So I would say first on the DM thing, like I've put more money or more time, not really money, more investment of my own time into Twitter versus—or X—versus the others. But it is so amazing once your network starts to grow, the number of people you might want to talk to that you see they follow you and now you can DM. It's like this unbelievable unlock and it's really powerful. And this digital, this ability to connect digitally is another element of speed of learning and mentorship that's available today that wasn't available 20 or 25 years ago. But you have to be in it to do it, and you have to understand the edge to get a benefit from it. But I think it's unbelievable.

There's people sharing their best information possible. They're doing it out in this public space. And if you happen to say something they like or they read something you wrote and like it or follow you, now all of a sudden you've opened a communication channel. It's crazy. So anyway, I think you want to be rolling around in these tools. It is the modern toolkit. And it's very easy to dismiss whatever comes up next. I'm guilty of being better at Twitter than I am at Instagram because I'm older and that's the one that I got to know. And TikTok, I'm even less. So it happens. But anyway, I think you need to roll around in it. In terms of approaching someone, I think it's really valuable to know as much about them as possible because it's respectful and that can land at the right time.

That can land in a very powerful way. Two, I think you want to ask for something that's very concrete and finite. I don't think you want to ask for, 'Hey, will you be my mentor for all of eternity? Forever.' I think on your first attempt, you should be asking for a very specific piece of advice, like a particular problem that you've done or a piece of work that you've created that you want them to opine on. But it needs to be something where the ask looks like it's maybe a five- to ten-minute investment from the other side. Just for the first one. Because if you propose something that's going to look like it's infinite time or an unknowable amount of time, it's going to be very hard for that person to opt in just because they couldn't do it across the number of inbounds that they're getting.

And then the other thing I would say is if you happen to be aware of a particular interest or even better, a new interest of the mentor, that's an area where you might be able to bring something to the table. You know? So, I mean, I don't want to talk too much about social media, but let's say you were really great at TikTok. And that mentor's not exploiting that channel. And you had an idea. As part of engaging, saying, 'By the way, two or three of your peers are crushing it on TikTok. I think I know why. I could probably write up an analysis for you, or maybe I wrote it up. I've attached it in case you're interested. I think you might really benefit from this.' If there's an opportunity to do something like that, now you're bringing something to the table.

See, in both of those, I love your answer because in both cases, it assumes that you're adding value, not just asking. Like it's true on social media. It's been surprising how many of the people I know today that I only admired from afar discovered me because like you, I started blogging in the early days of blogging and they would read my stuff and go, 'This is really good.' And then occasionally they would reach out. That's how my best friend who used to work at one of the biggest churches in the country got to know me 15 years ago. He discovered me. Some other people who've become very good friends discovered it, but I was adding to the world, not just asking. And I think that's really important for people to hear.

Similarly, in the cold call, what great advice: like, specific, measurable, short, do your homework. Like, "Hey, I read your book and you cover this and you cover that, but one question that hit me was blah, blah, blah." And then just be grateful for whatever you get. That's right. And maybe add some value in a new area. Okay, that's super helpful.

And I would be the 10,000th person to say this, not the first, but you got to let the "no" or the "no response" just roll off your back. You can't let that build up any kind of anxiety. Like, it's fine. Maybe they didn't see it. Like, maybe they didn't read it. Maybe they're not the type of person that likes to give back. It's fine. Like, let it go. Like, no big deal. Yeah. Yeah.

The other thing you talk about is peer-to-peer mentoring. And I'm not a sports guy like you are, so I'm sure to our listeners, they would get a lot more out of the names you drop in that section of the book. But you talk about, I think it ends up being seven friends who eventually became college ADs—for football, I think it was. I think that model is perfect for church leaders. Right, because everybody knows somebody else, right?

When we talked about it early on, I said I wanted to circle back to this. Yes. Is this it? Yeah, I think this is. So it's probably... The book has six principles interlaced with a bunch of profiles of people that, once again, started on the bottom rung, and most of them became the very top of their field. But one of the principles, probably my favorite, is titled "Embrace Your Peers." And I think it's a concept—mentorship is a concept that's been widely discussed and widely recommended. This one, I think, is less intuitive, but there are examples of people that built peer networks. And when I say the word "peer," I'm talking about someone who is on the exact same journey or climb that you're on. That's not...

two rungs above. They're on the same ladder rung you're on, and you're both trying to get to the same place. And the—the thing that's great about if you can find multiple people like that is you get shared learning. So it's not just you that's learning; you're learning what they're learning. Now, it requires that you be super comfortable with sharing what you're learning with them. And one of the reasons why I think this particular approach hasn't been recommended as much is a lot of people, especially people that want to be successful, are overly competitive. And they're what I would call sharp-elbowed. And the notion of giving your best ideas to someone that's climbing the same mountain you are feels counterintuitive to them and even feels like a bad idea.

But I don't think there's this great book about of our mental models from studying finite games like sports events and whatnot or board games. And there's one winner, they end and there's a winner and that's it. But infinite games, which life is, there's not just one winner. And most of these fields, there's a large number of winners. And so you got to get this out of your head that I'm competing with every single human that's in this field because that's a very lonely journey. And the example you mentioned when we started talking about this, in the book, we have a chapter about these seven young people who are working at the very bottom rungs of their athletic departments. They're all executives in the athletic administration at colleges.

And they meet at a conference, and they start texting each other and sharing ideas. And when they leave the conference, they go back to each of their respective schools, but they now have this text group. So oddly, they all end up top, you know, athletic directors at seven of the top schools in, in the country, um, and when, when we sat down and talked to them all, like, this co-learning thing was a huge part of why they were all so successful, and it got more and more sophisticated each year, and like, in the latter years, um, they were doing two- or three-day meetings. They were bringing their wives. They're inviting special guests to come speak on topics they don't know about. And then they take that away.

And I say it's odd they were all that successful. When you get in the weeds and see what was happening and that co-learning, it's actually not odd. It's more kind of, oh, it's actually intuitive, that's what happened. But I don't think it's intuitive to go do this. I think most people, hey, go start sharing with this other person that you might be competing with. It's not something that's logical to them.

Yeah, you know, it's almost like they started an impromptu DIY mastermind, right? Just with that text group and then annual gatherings, and then they sort of became three-day events. And I think that is such low-hanging fruit that most people miss.

And you brought up in the ministry, I mean, unless, you know, your houses of worship are right next to each other, you're not competing really with these other people.

We're all on the same team.

If you can find peers in other cities that are on the exact same journey you're on and get into this area where you're sharing different things you try—you probably try something new every, you know, once a week, right? And some of it works, some of it doesn't. And if that can be eight people sharing that experimentation... There's another story in the book in that peer chapter that's far away from ministries or athletic directors, which is Jimmy Donaldson, who is a young 17-year-old kid who loves YouTube. Like, he just loves YouTube, flat-out loves it, and starts playing around with how to, how to, how to basically be successful on YouTube, and meets three other people. They do a daily Skype call for like 16 hours a day, and

and Jimmy Donaldson becomes MrBeast, you know, who is the most successful YouTuber on the planet. And, you know, at the time when he started doing that, you know, his mother wanted him to go to college. He was not particularly interested in it. He was wildly interested in this. And he says, after the fact, referencing the Malcolm Gladwell book, 10,000 Hours, he said, well, he says, 'To hell with 10,000 hours, we're getting 40,000 hours because there were four of us learning at the same time.' And they were learning how to master this new craft of being good at putting videos on YouTube. And he also said, if a fifth person had been on that call, they would have made a million dollars also. Like, the techniques they were uncovering were so new and so powerful that if you mastered them at that point in time, you got immediate financial reward out of it.

Yeah, there was only one MrBeast out of that group, but everybody else, I think you said they grew their followers to like a million followers. Yeah, they all did well financially.

They didn't all do as good as him. But the point being, it's very similar to the athletic director story, but I think in the ministry, this is a huge opportunity. Especially if you can find people who enjoy the same type of worship and the same type of congregation that you have, and you can find other people like that in other parts of the country, and everyone's experimenting with techniques and social media and other ways of growing audience and congregation, I bet it'd be super valuable.

Yeah, that's what I found 20 years ago in what is now the Irresistible Church Network. It was just like-minded leaders. We're trying to build that out. We are building that out in the Art of Leadership Academy. One of the things, Bill, that you've had experience with, you've hinted at it, right? Yeah. They're not all OpenTables. They're not all Ubers. They're not all Zillows. You lose some bets, too, in venture capital. And Jimmy Donaldson, I mean, his story's fairly well documented now. I mean, he spent years posting videos that got zero views, three views, failure. And his mother had every right to say, listen, you're disastrous at this. Please go to school. It seems to me like this is an editorial comment.

I'd love your take. But it seems to me like we've moved into an era where people almost want the success more than they want that curiosity. It's like, "I just want you to show me." Like, you know, with all of the leaders you met, what is the tension between loving the craft, as we've identified it, versus, "No, I just want to succeed. I want the hacks." And then what is the long-term prognosis for each mindset?

I think that, unfortunately, the combination of very, very, very well-intentioned parents and very, very well-intentioned counselors and advisors to young adults have gotten to a place where they're very concerned about the economic stability of this person passing from being a teenager to a young adult to an adult. And they very much want them to chase a traditional job that just feels safe. And, you know, we sit here now where many of those safe jobs are under threat from AI. But if you go back before AI, you know, there's a 2023 Gallup poll and only 23% of Americans say they're engaged and thriving at work and the rest are not. And so you don't have a situation where a lot of people feel

like these people we're talking about that are in flow, that want to study all the time. A lot of people aren't in those places. And I think at least part of it is we've become quite over-structured in how we turn children into young adults and teenagers into young adults. And different people have talked about it. Jonathan Haidt in The Coddling of the American Mind called it the resume arms race. And we all know we're guilty of it. We all know it feels a little odd when you're pushing the six-year-old to basically resume pad for their college application process with cello lessons and volunteering at the university. I don't know where, but like, it's all performative. It's not, you know, they're doing it for the sake of doing it.

And the kid's time is just way more used up. Rick Rubin in his book said, "As children, few of us are taught to understand and prioritize our feelings. For the most part, the educational system doesn't ask us to access our sensitivity, but to be obedient, to do what's expected. Our independent spirit is tamed. Free thought is constrained." And on top of that, the colleges, if you go back 20 or 30 years, they wouldn't let you pick your major to the end of your sophomore year. At many schools now, you have to apply to a major as part of the application process. Absolutely. And so once again, you're just being forced into a tighter and tighter, narrower and narrower path that doesn't really allow you the freedom to go find this type of curiosity thing that I think is important to find.

And so one thing I would really encourage, whether it's parents or counselors, if you happen to see a spark that might be, you know, like Danny is with restaurants, like fan that flame, like do anything you can to help that individual feel like that's possible. And as a parent myself, I know it's hard. Like if you think, you know, this particular individual could go be a McKinsey consultant, you know, they'll do very well financially and they, you know, but if they really are passionate about being a, you know, basketball coach, that's okay too, you know? Like if they're really, really passionate about it, they're gonna have a way more fulfilling life doing that. And they're gonna fill up with energy.

They're gonna be in that flow state all the time. And the other thing I've told some young kids who are very purpose-driven, almost every single person we cover in the book that ends up thriving in their business, and Danny's a great example, ends up touching so many lives. They end up having so much positive impact on the world because... they redefine their industry and then they share back into that world. And if you met someone that worked for Danny, anybody that's ever worked at one of Danny's restaurants, it's like one of the highlights of their resume. They talk about it for the rest of their life. It's a piece of walk-around collateral that you were involved in this big tent that Danny created over time.

And so... Anyway, I think that's really, as I mentioned with the Jerry Seinfeld story and the book he read, I hope that we can give as many people as possible permission to go live this life of freedom flow, as you say, because they're in the right place. I want the book to speak to the young people who are making the decision on what they're going to go do with their life, but I also want the book to be helpful as a guide to the, the people that are around that young person and giving them advice on how you should maybe approach that situation when it comes up in the future. And I think if you teach yourself to be more... open-minded and encouraging. I got this great email from a parent that had watched the video that I mentioned, the early version of this book.

And their child was at a reputable college in finance, I believe, and came home one day and said, "You know, I'm really spending all my spare time in this other thing." And it wasn't as certain as finance or anything like that. But the parent told me about their journey from acceptance to embracing to encouraging. And as the parent went through those stages, the relationship between the parent and the child blossomed. And the confidence, the parent said, the confidence of the child went up dramatically as well. And hopefully they will go thrive in that new industry. But it was such a heartwarming email to get.

We have a software engineer and an accountant as our two sons. And we've had that conversation. They're both in their 30s now, but they're like, "We felt that pressure to get that career." And I'm like, "Yeah, guilty as charged." And so it will continue to lead to some interesting conversations.

One data point that was uncovered by Dave Evans in the great book, Designing Your Life, if you look at the stats, like four or five years out of college, 40% of people are no longer in the career that their major was. And when you get to 10 years, that number drops even further. And so it's important, I think, for people to know that because we've... we put so much weight on this college journey and this degree that you maybe have created this belief that you have to stay in that lane. Like, "Oh, I've invested all this time. Like, why would I ever consider leaving?" And I think just helping... young adults understand that people do move around. And by the way, some of the people that move around, David Epstein in his book, Range, like some of the people that move around are the ones that have the biggest impact on a field.

Like they come into it late, they studied something else, like they bring new ideas. And so it's perfectly fine. I think that's another lesson that's important for people to understand. It's perfectly fine to repot yourself, to move around, to try something new. And the one caveat I would give on that, which I think is important, is don't overspend early in your life. Like don't spend right up to, because then you're stuck. Then you don't have the flexibility.

You get the golden handcuffs. It's like, 'I absolutely need this job,' and you can't pull a Danny Meyer and take a 90% pay cut and do something else with your life.

It's super important when you're young to not live right up against the edge of your paycheck because then you get stuck.

Oh, wow. I'll tell you, there's a couple more things I'd love to ask you about before we wrap up, Bill. One's definitely not a softball, and it could be a whole podcast, but I'd just like your take on the impact of AI. I mean, you're very connected and have invested in a lot of AI companies. What is the impact of AI on jobs, do you think, particularly white-collar jobs? Yeah.

My first reaction is there's this concept that I read about a long time ago about how humans evolve with their tools. And so if you took a human, you know, with no hoe, no saw, no, you know, fire, whatever, like they can't do as much as someone that has these other things, right? It's just pretty obvious that we evolve with our tools. And so there's a new tool out there, and it's called AI. And if you're not rolling around in it and you don't know what it's capable of doing in your field, you're exposing yourself to a really dangerous situation. And I'd say that's true in any field. And so this thing came at us fast. It's like an ultra-... You know, the calculator came along and then the computer came along.

This thing is so kind of powerful, fast. Imagine that. Instead of stopping with the calculator, imagine the computer just showed up and you never had the calculator transition point. I think it's kind of that powerful. And unfortunately, if you don't have AI skills, you need them. You just need them. And so I would tell everybody out there in every field, know what it's capable of in your field. Like play around with it, get to know it. And the thing that's going to give you the most job protection is to be that person, the person that understands it the most in your field. And I wish it weren't true. I mean, you go back to like the lathe versus the loom. I'm sorry, the loom versus the seamstress where the word Luddite comes from.

Like, innovation happens, and that leads to more progress for humanity. It leads to more prosperity for more people on the planet. But it does lead to dislocation. And the worst thing, the thing that's going to increase your odds of dislocation the most, is to either be a naysayer or to never touch it or never understand it. It does have limitations, but it gets better every day. I've met a lot of people, especially older people, who used it once, got it to give them a bad answer, got it to fail, and then they're like, 'Oh, no, that doesn't work. That stuff doesn't work. Look,' and they point to it. 'Look, I did this test,' and I say to them, 'Did you do that test again six months later and six months after that?'

Because you may be surprised that that same failure may not be happening anymore. Like, it's a real, like, whatever instinct you might have to say, 'Just be salty or negative about it,' like, that's a sign that you're in a really bad spot.

Mm-hmm, mm-hmm. So you've also had, my last question, I guess, is a chance to meet some of the top leaders in the world. You've worked with Michael Dell, you've worked with Jeff Bezos, you've worked with CEOs of so many companies that we've met. What are some common, not just in the startup phase where you're, are we gonna take a bet on these guys or not, but when you watch them lead over 20 or 30 years, what are some of the top characteristics that you see these leaders embody?

Yeah, the first thing that pops to mind is this continuous learning piece. You know, the fellow Canadian, Tobi at Shopify, is one of my favorite people on the planet. And like any time he does a podcast or interview, I'm immediately drawn to it. And I would encourage everyone to watch. But he, on a recent podcast, said, said, you know, he was just talking about reading. Like, reading is like this free gift. There's people putting knowledge out there constantly. And I just found they all devour. You know, Warren Buffett would set aside three hours a day just to read things he didn't know. So that's one. The second one I would say is... a confidence in having independent opinions. Like, and I see this with Bezos quite a bit, and I certainly see it with Tobi at Shopify.

Like, they're not... they don't just go along with what everyone else is doing because everyone else is doing it. Like, they're constantly questioning, you know, what's right or wrong. They know there is huge advantage in having an opinion that's not... consensus, right? If you have a non-consensus idea that's right, that's where you win. That's where you make the most money. And so you need to be looking for that. And that's this kind of... superpower, you know, advanced level execution as a CEO is when, because early on you're just, you know, we said, 'Study the history, study the greats,' like you're building this fabric of best practice and mental models, but the ones that go the step further start to innovate on top of that.

And sometimes they get that from talking to people outside the field is a great way to get that and bring it back. But, but that's the other one. And then they're all great leaders of people, which is a skill that I'm not particularly blessed with. Um, it sounds like you've studied it quite a bit, but you can't, you can't, you know, if you're successful in venture, I mean, as a founder, your company goes from 10 employees to a hundred to a thousand to 10,000 to a hundred thousand. And, um, you can't do that if you're not good at leadership. There's no way to get that many people. And one of the things that I've been so impressed by with Bezos is that company's up to, I think, 400,000 employees, maybe more.

And it's still innovative. And how... He's not talking to all those people. He instilled processes through the organization that make it okay to try new things and to fail. And that's super hard to do. It's just super hard to do. I think Elon's leadership across multiple companies even is... a curiosity to a lot of people. It is a curiosity.

I've read Isaacson's biography of him. And I mean, it's going to be very interesting to see when his time on Earth wraps up.

Yeah, if we can unpack it. I'm not sure people fully understand it right now. No, he's a different bird. He's a different bird.

Bill, I got to tell you, this has been, the time has flown. I feel like I am much better equipped and understanding around, well, a multiplicity of things. The book, by the way, was that a Tom Petty thing, Running Down a Dream?

I found quite a number of use cases prior to his. So I don't think he has exclusive to the name. He doesn't own the trademark.

But it's a great song.

I played basketball at the University of Florida. Tom Petty was born in Gainesville, Florida. And so there's a lot of Petty in the water there, as you might say. Yeah.

We end the book with a Tom Petty quote, actually, at the very end.

Yeah. I had one in my book until very recently. I just took it out. It was, 'The Waiting Is the Hardest Part.' Another great song. So, anyway, Bill, the book is called Running Down a Dream. It's available everywhere. Anything in particular, if people want to follow you, you're very active on X?

Yeah, on X. @bgurley is probably the best place to follow me. Got there early. I want to mention one more thing, Carey. As the book launches on February 23rd, I'm going to start moving my attention towards a foundation that we're launching simultaneously with the book.

So we're going to take applications. So for people that want to chase their dreams but may be stuck financially, we're going to do grants. We're going to do 100 a year. That's where we're going to start, $5,000 grants to people to help them chase their dreams. And so I don't know how that's going to play out. I'm going to put all my proceeds of the book towards that effort, but I'm excited to see if we can help some people achieve their dreams.

That's amazing.

Okay, and where would they discover information about that? rdad.org. So rdad.org.

Okay, and we will put that in the show notes with everything else.

Right now it just has you put an email in because I haven't built the application process yet, but I'm going to turn to that right after the book's out.

Okay. Bill, this has been a great first conversation. Thank you so much.

Thank you. Appreciate it.

Always fun to have a legendary investor on the podcast. We have everything you talked about and more inside the show notes. Best place to get them is in my Art of Leadership Academy. We are adding leaders every single day. We're around 20,000 now leaders who have signed up for free for the Art of Leadership Academy. There's also a premium version, which gives you much, much more. But if you want the show notes, go to theartofleadershipacademy.com. Next episode, I've got Chelsea Smith coming up. Also coming up, Preston Sprinkle, Eric Ries, Dave Ferguson, Rich Villodas, Dr. Nicole Martin, and Joel Muddamalle. Thank you so much for listening, everybody. If you have enjoyed this episode, please leave a rating and review wherever you're watching, wherever you're listening.

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