#125 The Most Important Career Advice You'll Ever Hear (In The AI Era) | Bill Gurley

25:37And then it said basically, if you have bad judgment and AI use, slop cannon, you create a lot of really bad things. Good judgment, lot of AI use, sort of superhuman. You create incredible things. And I've been thinking about that lately because I felt it. We did this job posting, Bill, and I was like, we're hiring sort of vibe coders. We're hiring them in every single department. We're hiring engineers as well, but we already have engineers that we've been hiring. I've never hired this person that's just like AI curious. And we get thousands of applications for it, right? But then as I'm going through it, I'm like, wow, people have built a lot of stuff, but a lot of it is a questionable choice of what you are building and how and why.

26:20And that product is actually really terrible from a UI perspective, right? So I'd be curious for you, like in this world, it does seem like you have to really have taste about what you build and why, too. Do you think that's true? And if so, how do you tell if somebody has it or not?

26:34Bill Gurley:Yeah. I mean, it may be that both relationships and taste become even more important because of the volume of information that can be created could create more noise. One thing I would really tell people, and you've probably been down this path yourself but like the more you use ai the more you understand and intuitively have a feel for what it's capable of and then the more you push it and into places you might not have thought about before and i'm i'm surprised i was surprised yesterday you know like oh wow you know it figured that out and if you're not once again if you're not playing with it every day not only do you not know what it's capable of, but you're not developing your skills to get it to be as good as it can possibly be for you.

27:26Like there is an element, people use the phrase prompt engineering before, but I think it's more than that. I think it's having awareness of when it might help you and knowing you can go to it more often. Yeah, that's a good point. Yeah, I guess it's almost like you'll see an expert with all the ways they know how to utilize a tool, any type of tool. No doubt. And the stuff that came out in the past two weeks, which I haven't played with yet, or even more of that. That's my existential drug. I haven't built a club yet, but probably should. My president just did, and he came in wild-eyed yesterday.

28:02He's like, I've been working on it for the fourth day. I didn't sleep last night. I love that. But me too. And you know what? He's the former president of Mr. Beast. He's a super successful guy. He makes a ton of money. He's built a lot of companies. And yet even he is so curious about what's happening. Yeah. And you were asking about the elements of a great founder. That part's in there. They can't stand. They have immense FOMO about new technologies. Immense FOMO about new technologies. That's a great line. Chris Saka had said something really interesting about you, totally off the AI subject.

28:38But Chris Saka said that when you are in a meeting, you will be sitting there silent for most of the meeting. And then you'll say like 10 poignant words that will change the trajectory of the entire meeting. And you're a humble guy and you didn't even want to write like a memoir. You wanted to write something to help people. So I'm sure you hear that quote and you're like, whatever, Chris. But - No, that's not my reaction. Go ahead and finish the question. But my question is like, you know, you're in rooms with these power players all over the world. You're in rooms with other big investors, all your partners at Benchmark.

29:10How do you make your words count? How do you get heard by people?

29:14Bill Gurley:By the way, that thing Chris described is an evolved skill, not something that came naturally. And if you read the stories of the elders, the great early venture capitalists, you'll find a mention of that precise technique. And I probably read those early on. And it's hard. It's super hard. Like the human wants to blurt out the best answer first. And, you know, there's this sales tool, gong, that they use to record salespeople. And then see, I wish every board meeting had a gong recorder and then immediately posted a pie chart of who talked the most. I wish. I've never said that out loud before.

30:05That's a great feature. But I would love to see that because I think it would encourage more people to do what you just described. And it's super effective. It's just very hard to do. It's very hard to bite your tongue. And the other benefit of waiting till the end is you're going to have more information. You're going to synthesize while you prepare to say what you're going to say. And it's going to be more efficient, obviously, if you say less. It turns out it's also more impactful for the reasons you just described. Yeah, well, we were talking about Rick Rubin before we started. Yeah. And I'm obsessed with this one line of his, which is that he is not a producer, he's a reducer.

30:48Yeah. He's always trying to get it down to the core. Yeah. And that reminds me of you in this way in meetings. And I know you met, you said you spent time with Rick. I did. What did you take away from him? Was there a story that you were like, God, this is so good, I want to go home and tell my wife? I was kind of on pins and needles going in because I hold Rick in this really special place in my brain because of how unique and individual he is and how different he is. And I'm a huge music fan and all the different genres he's touched and made magic with, it's clear there's something special there.

31:27And then you read his book, it's not written like any other book that's ever been written. Um, it's, uh, it's Yoda-esque. It's, it's small words put together that are profound, but not, um, not obvious in how to interpret. And, you know, some people have told me they've read Rick's book like a fourth time. Like, I think it may need that, like to soak in. So I, and so I just, I was so thrilled to be there and, um, I'd watched the documentary about the studio. There's a four part documentary. And so just being there was super special to me. And I was so in awe. Maybe I, you know, the whole thing felt like the answer to your question was every single second of being around him.

32:13I'm that much of a fanboy, but it was great. He was so prepared. I was so, I, when I was writing the book, I, um, I was very curious why I did the podcast because, um, you know, here's a guy that's remarkably successful in his field, probably, you know, arguably the best of all time, but certainly top five producer of all time. And, um,

32:40Bill Gurley:and he does a podcast, not just with music people or even Hollywood, it's much broader than that. And I remember listening to him talk to Jay Bhattacharya and I'm like, this is insane. Like, like this is amazing. And I asked him, why do you do it? And he, he, he said, it's all about curiosity. Like just, just scratching itches and learning as a hobby. And I think that's profound. Like I really do. I think that the best and the brightest, you know, there's a recent podcast, I forget who did it with him, with Toby of Shopify. And I, if Toby talks, you know, anywhere publicly, I consume it within 24 hours.

33:24I just find him so wonderful and so fascinating. And in this particular one, someone asked him, like, what's the easiest life hack of all? And he said, read, like, read, read, read, read, read, read, Like, don't stop reading. He goes, people write down stuff that they've learned over a lifetime and you can consume it in a day. Like, that's so easy. You should do it all the time. And Buffett has said similar things. It's profound. The learning tools are unlike they've ever been. And that's why I go back to what I said earlier. If you're on a self-directed path where you're trying to be, I have a phrase in the book, a candidate of one.

34:05where you want to look like a individual and you know how you, you know, the lane you're in,

34:12Bill Gurley:you know, what, where you're headed toward and you want to, to add to your, yourself more learning about where you're headed. There's never been a better time. Like in the history of the world, there's never been a better time. It is, uh, it's insane. The opportunity that's out there for you. Well, I loved a lot of what you said in the book about finding mentors. So that's a question, And, you know, anybody who's on the internet a lot, people ask, how do you find mentors? It's a big question. I've actually never thought about it. Have you ever called anybody your mentor? Yes. Like, did you ask them?

34:46Were they like, were you like, will you be my friend?

34:48Bill Gurley:No, I don't think it went down in that way. I didn't say, will you be my mentor? Is that a good question to ask? Should somebody ask somebody, will you be my mentor? Probably not. Like, I don't think you should use, it's a very heavy sounding ask, you know? I think, and so I'll give you, I'll give, I'll give your listeners a cheek. I still hope they buy the book, but I'll give them like my first thing on mentors is, um, take, take the people overshoot. They try and go too high. Like, and so take all, I think it's awesome to identify the people in the field you're going to go after that you hold in highest regard and respect the most.

35:26Bill Gurley:Call those your aspirational mentors. is create a file, you know, in whatever digital folder type thing you like to use, Notion or Google Docs or whatever. Create a file for each one of them and study them relentlessly. Find every podcast they've been on, find every YouTube, any interview you can find, anything they've written, put it in the file. Like keep it like a little journal of yours for each one of them. One day you may meet them, and the fact that you've done all that work will make you much more likely to be able to engage with them. But you're going to learn so much along that way. So the ones you thought you were going to cold call, don't do that.

36:08Bill Gurley:Do what I just said. And then for the ones you're going to actually try and meet, just go down a few levels. Like if you go down a few levels, you're going to be asking someone for advice that's never been asked for advice before, and they're going to be flattered that you're doing it, that you know who they are, that you found who they were, and that you respect what they've achieved. You're going to be the first person that's asked them that. And because of that, they're going to be responsive. And so people overshoot, that's a great way to kind of divide the world into two parts. And one day, who knows?

36:44The first profile in my book is Danny Meyer, who's a close personal friend and one of the most wonderful humans I've ever met. For those that don't know, Danny's one of the top restaurateurs in New York, maybe the top, most people would say. Andy created Shake Shack. That's how most listeners would probably know him. But when Danny decided, and he had this intent, and it was in a single moment at a dinner one night to go be a restaurateur, he made a list of the 10 people he respected most that were changing the restaurant industry. And he did exactly what I said. He studied them. He kept a folder on them.

37:23And when I was preparing to give the talk at the University of Texas that was the precursor to this book, I called Danny, because I just thought about this before I was about to go give this speech. I said, did you ever meet any of those 10 people?

37:37Bill Gurley:And he sent me the 100 emoji. So he had met, He ended up meeting all of them, which is awesome, right? And as someone who climbed the ladder in their field, I will tell you, like meeting or perhaps even impressing those people that you put on that initial list is a truly amazing, fulfilling life experience. Like it's really cool when that happens, you know? It's incredible advice and I don't think it's given enough. Yeah. I have this other thing in the book that I feel compelled to share that gives me goosebumps the first time I saw it. When Anthony Hopkins watched Breaking Bad, he sent Brian Kranz in this letter about how impressed he was.

38:25And I don't know if enough people do that enough, but I can't imagine that any Oscar or Emmy felt as good as getting that letter from Sir Anthony Hopkins. You know what I'm saying? That's a great point. It just, the weight that must carry to have someone at the top of your field tell you that you did something amazing. Yeah. And it costs nothing, right? Right. No, but it's so important because I think these days, like what I see a lot of people doing is everybody, when they try to get mentors, they go really wide. They try to go talk to everybody who's famous or well-known or at the top of the game, but they're really narrow in what they know about them.

39:09And you're saying, do the opposite, go really deep with you. And then on top of that, it's kind of like job searching. It's like try to go get every job in the world, apply a thousand times. You see that on X, you know, they'll say, well, I've been out of a job for six months and And I've applied to, you know, a thousand places. But it seems to me like going deeper and more sniper rifle as opposed to shotgun works better in most things in life. And you could even maybe, I loved the story you told about Bob Dylan and his mentor even and what he did to track down one guy. And this is Bob Dylan. Like if Bob Dylan has to do it, what do we have to do?

39:45Bill Gurley:And by the way, this is another area where like if you're playing around with AI, you're going to learn like everything it's capable of. And if you're meeting any human and you haven't done a pro, you know, search of everything that's possibly out there on them so you can know as much about them before you meet them, you're just not doing it right. It's true. But you know what's crazy? Don't you find most people still don't? Yeah, I think most people don't. But I think in the future, you will, you know, listen to a podcast on your way to work where your AI is telling you everything you possibly need to know about everyone you're going to meet that day.

40:29I think that like that certainly will happen. I talk a lot about owning stuff, businesses, assets, your time, but owning your privacy matters too. So right now your personal info is being bought and sold online without you ever opting in. Old addresses, family names, phone numbers, it's all floating around. That's not great, especially if you're building something or simply don't want random people knowing where you live. That's why I like Incogni. They reach out to data brokers and get your personal info removed and they keep doing it because new sites pop up all the time. It's super simple. You sign up, you say what you want removed, they take care of it.

41:02And if there's something specific you want off the internet, custom removals covers that too. My rule is pretty simple. If I wouldn't give it to a stranger, I don't want it online. They can't harm you if they can't find you. So check it out at incogni.com slash big deal. I want some Bill Gurley predictions. What do we think? What do you think? What are some crazy spiky predictions you have for the next year or two about tech and just the world? I think this, I think everyone is finally, I think Clawbot actually helped finally push us towards this kind of personal assistant concept, this AI thing that's like your running buddy that I really think most people want.

41:50And there's all kinds of questions about privacy and how much you share and whether they get shared beyond. Like I get it. Like, but I think people are going to want this so bad. Um, you know, I missed it.

42:03Bill Gurley:I was late to a meeting yesterday because I, I tried to call like three or four people and they said, Oh, today's a holiday. And so I just got lulled into thinking there was nothing on my calendar. And, and then I was late to this thing and I was thinking this morning, like someone should have started pinging any channel I have, you know, especially like if I'm not moving, like if I'm not moving, like, like someone should know if I'm not moving, I'm going to be late to this thing. Like, and it could ping me and tell me and it will like that that's coming. Like that's going to happen. Like for sure.

42:39I totally agree. Okay. So we're going to have, we're going to have relentless little AI reminders and assistance. I think so. What else do you think? I mean, it's so hard to see the future right now because everything's possible and anything's possible. And, you know, I think there will be vertical models that get really good in very specific places. Health. I mean, the ones people are leaning on the hardest are legal and health and coding right now. But I think it will happen in many, many, many fields. as people figure out what's capable, what's possible. You know, I think fixing certain industries will not go as fast as you would want because of things like regulatory capture that make it very hard for innovation to thrive.

43:35Healthcare is a good example of that. What else do you think that other people might disagree with you about? What else do you like? Oh, I can give you an easy one on that. There's a competitive dynamic in China right now on AI models that includes open source. And I don't think the world, especially the politicians, understand how unbelievably powerful open source is as a weapon. like is a competitive weapon.

44:15Bill Gurley:And if you have 10 companies all doing open source, the minute an idea is shared, it's available to the other 10 and they absorb it immediately. And it just creates this dynamic that's hyper competitive. It doesn't mean when I say it's hyper competitive, that also means it's less likely to create wealth because, um, but it's a There's a phrase in economics called pure competition that you can look up on Wikipedia or whatever, and you'll study it if you get a finance degree. But in pure competition, no one has an edge. Marginal cost moves to marginal price. It's great for consumers. Consumers end up with the lowest price point.

44:57Um, and some would argue it's the ideals, um, it's the ideal, uh, goal of capitalism, you know, to, to get the lowest price to the lowest, you know, for the consumer and prosperity

45:11Bill Gurley:thrives. I actually agree with that, but open source is hyper competitive compared to a situation where people only playing with proprietary models. And so, you know, people say we're six months ahead or three months ahead. I think the odds that the U.S. with two proprietary models can stay ahead of China with 10 open source ones is very low. Fascinating. So what do we do about that? Well, here's what I fear we're going to do about it. This is really off the subject. But what I fear we're going to do is the two leading players will recognize the threat and weaponize regulation, which is what they started doing three years ago.

45:56But no one's funding more lobbyists begging for AI regulation than Anthropik themselves. And they'll use that to try and deal with the threat. What's really going to be interesting is the rest of the world. So for the past 100 years, I think the U.S. has considered rest of the world their market. And that's true in industrial-type products, but it's certainly true in technology. And if you look at the internet, China kind of had a fence around it, and the rest of the world used the U.S. products. They used Google and Amazon and Uber and all these things.

46:39Bill Gurley:and if we pull up this huge regulatory wall, you know, it may be the U.S. that has the fence around at this time. It's going to be really interesting. Copyright's a super fascinating thing. Like, like if the Chinese models don't protect copyright and the U.S. ones are forced to, what does the rest of the world do? You know, do we go to the EU and say, you can't use Chinese models, they don't respect copyright. And how will the EU respond? I don't know. Yeah. It's fascinating because I did see some of your tweets on even IP and, you know, no patents, no copyrights, and how in some ways that would be better for the world.

47:18Bill Gurley:I think it would be. This is very controversial, by the way, but I do. I do. Well, explain why it's controversial. And even like you could steel man it. Like Walt Disney would be like, hey, Bill, fuck you. You know? Yeah, I think copyright lands harder in people's brain because they think about it as an artist individual creativity and that like hits people emotionally. Patents, you know, in the U.S. have been systematically abused, you know, and you can you could just go talk to AI about it. How do, you know, pharma companies use rolling innovation to extend patent life, you know, way beyond what the original intent was?

47:59And it happens constantly. And people will say, oh, but if you don't have patents, you won't have innovation. And I just don't believe it. Partially because, you know, our firm was lucky enough to be an investor in Red Hat. So we've been investing in open source companies for 25 years.

48:16Bill Gurley:And, you know, there are plenty of people who want to innovate who don't need the government protecting their innovation. You know, Tesla has famously open sourced all their patents, you know, as an example. And I'm fairly certain that Elon agrees with me on this point. But we may be – I think we're pretty – we're two pretty lone wolves on this topic. What about like name and likeness and, you know, that in the age of AI? Yeah, because so much of AI is just trained on art, you know, let's say. Look, I recognize the copyright thing, you know, really gets people's skin up. And I would just say, you know, a 17-year patent is way too far.

48:57Like, we need to dial it back. I think that we will innovate faster without it. But the other way you get there is hyper-competition that pushes you to open source. And it's fascinating. I visited China in August, and I was doing research for that trip. and I went back and the previous five-year plan, China notoriously publishes these five-year plans that are pushed to the provinces to encourage them. Here's the things that the higher-ups are interested in. And open source was in the one five years ago. I think that China has been accused of being a IP thief for a long time. So it's very natural that they would see open source is a great place to run towards.

49:46And they have. And I think people may be making a mistake and not understanding why that might actually be the right perspective for a country to want to embrace. Yeah. You told a story that I thought was fascinating about - And by the way, I think you end up in a better position globally from a competitive standpoint because that hyper innovation that comes from all those open source sharing, just move your products faster forward.

50:17Bill Gurley:And I'm not convinced, we're getting into really esoteric concepts. I'm not convinced that having large market cap companies is necessarily a massive advantage. And it could be a sign of monopoly. I think that's very reasonable. I have a question on that. One of the things that I love in your book and what you've talked about. And really some of the ethos in Silicon Valley is like collaboration instead of competition. So like I come from a private equity background where, you know, we just, we just steamrolled everybody and we competed with everybody. And it was a lot of zero sum games. I buy this company or you buy this company and you lose if I win.

51:01And then I had to lose that sort of when we started investing in venture. And I definitely had to lose that when I got on the internet because it's like I've realized collaboration works a lot more. But I'm curious, you're still a competitive guy. Like you're a former basketball player. You're competing in deals. So like, should you try to crush your competition or should you work with them? Well, the advice in the book, most of it that gets into this topic you're hitting on is in a chapter called Embrace Your Peers. And it's probably my favorite principle in the book, but mainly because I think it's the most unique of all the points that I make.

51:39And I've found some amazing stories that I share in the book that you can go read. But I found that far too often humans, and I'm not talking about companies, I'm not saying companies need to have friends, but they probably do. But humans, when they're out trying to climb up the ladder, would do themselves a massive advantage if they would embrace a group of peers. So finding five to ten other people who are climbing the same ladder you are and share, collaborate, and support one another. And the number, you learn faster. Your network is bigger because it's not just your network. It's the group's network.

52:29If it's authentic, they will be there for you on the hard days. And that will really matter. Like that will really, really matter. Like in ways it's, if you haven't been through it, it's really hard to say how big a deal that is. And you'll have fun.

52:48Bill Gurley:And you'll – like, one way to know if you're really doing it right, when they win, you're sincerely happy for them. Like, you really are. And if you can get in touch with that emotion, one, your odds of success are going to go way up. But I think you're going to enjoy the journey a lot more too. I really do. And in most fields, like not downhill ski racing, but in most every other field, there are a lot of winners. There just are a lot of winners. You're not crowning, like being, supporting this other person isn't crowding out of position for you. But I think a lot of us are taught to think that way.

53:29It's a good way to, because I think even like, you know, as I've climbed to whatever level I'm at, you also know the people who are anti-collaborative and who aren't actually wishing you the best.

53:41Bill Gurley:I'd stay away from those people. Yeah. I'd be outspoken. Like, there are sharp-elbowed people in this world, and you can feel them a mile away. And let them be them. Like, I don't think you need to be antagonistic or do anything about it. Don't let them in your peer group. Yeah. Like, don't even invite them. Yeah, which kind of goes to show that if you are the collaborative one, you might win even more than the really good competitive one. Yes. Because I don't, you know, they don't want to let them in. Yeah. And look, I think I'm all about competing and winning and thriving. I don't want it to sound like I'm not, but your odds of getting from the bottom rung to the top rung go way up if you're willing to share the ride and share your best ideas.

54:29That's the other thing. One thing I definitely have learned over 30 years of working in business, this thought that you have this unique idea in your head that no one else does is far-fetched. It really is. and walking around thinking that is not helpful. What's the worst thing somebody can say in a pitch to you? That was a bit of an orthogonal question. Well, my thought process was. Yeah, tell me that. That would be helpful. You hear ideas every day. And I bet you often hear, this is revolutionary. You've never heard this before. Let me tell you this idea for this business. You're like, well, that was the 42nd pitch I've heard on this same idea, Yeah, which is probably why you come to think that no ideas are unique.

55:14Yes, yes, that's for sure. And I've also watched founders kind of get really bogged down in a ditch thinking someone, you know, invaded their space and stole their stuff. And like, I don't think it's helpful to them moving forward. And I don't even think it's true. I think it's pretty some like, here's a great example. Do you think there'll be a new age CRM built around AI that won't, that'll start from zero, uh, code and like, and zero and, and will be better than, than Salesforce.com and it won't evolve from all those fields,

55:52Bill Gurley:but it'll evolve in a different way. A hundred percent. And there's probably 20 founders doing it. Right. I don't know which one will win, but, but, but the odds that like, oh, I thought of that first is, is like, that's silly. It's silly to walk around with that notion. It's funny with the thing that I thought of when you ask about the founders. I was watching American Idol last night. I've watched it since season one. It's like my guilty pleasure. I would not have guessed that. It's like my Hallmark channel. But they've really gotten into over-dramatizing these journeys that they have. And some founders have started putting that in the front of their pitch.

56:31Like, you know, my mom almost died and that's the reason I'm starting this thing. And it gets a little cringy, you know.

56:39Bill Gurley:That's not the worst thing. But you can really, I think you really start the meeting off poorly if that seems insincere. Especially if you're telling a story that's that heavy. And so I started an accounting software package. You know what I'm saying? So the total addressable market is fine. No, I'm just saying they're not connected, you know. That's amazing. Be authentic. Be authentic. Don't be inauthentic. You have a lot of stories, I think, that kind of show how most of these people who win are authentically obsessed with whatever it is they're doing. And you told this story about there was like a Steve Jobs of China and a ridiculous thing he did with Post-it notes on his employees' cars.

57:21Can you tell that story? Because I was like, that is a perfect example of obsession. Yeah, you're talking about Lei Jun. So Lei Jun is the founder of Xiaomi. And, you know, as I go into the story, I'm going to share with you something. A famous and very successful Chinese venture capitalist told me on my last trip. He said, every single founder and venture capitalist in China studies the U.S. relentlessly. They watch the YouTube interviews. They listen to the podcast. They study them like crazy. He said, founders and VCs in America don't study Chinese. And I said, oh, that's a profound statement, right?

58:04Like just even thinking about that, it's pretty profound. So in that spirit, I would encourage everyone to go watch the, I think it's the 2024, 2025 Leijun State of the Union on Xiaomi, which is translated on YouTube. Because that's where I got this data from. But it's worth watching because he's as good as Toby. And I fortunately met him about 20 years ago. And this is his third company since then. But about 10 years ago, he decided to build a phone, which isn't easy. And it's now the third best-selling handset in the world, Xiaomi. And then about five years ago, when Apple was thinking about building a car, he decided to build a car.

58:50and that car is now in production, sold out. There are some amazing reviews online of Americans who have gotten a hold of the car, including the CEO of Ford. So you can go watch those and read those to get a sense of the sky. But in that State of the Union, he tells the story you talked about where once he decided to build a car, he took a first shot at it and realized it wasn't special and then he backed up. and some of this talk comes from the backup and re-approach it.

59:22Bill Gurley:But he decided that he wanted to drive every car he possibly could to get experience because he had been driven around by a driver, which is very common in China. And so he went through the parking lot of his employees and there was a car he had never driven before. He put a Post-it note on it that said, I want you to tell me the three things you like about your car and the three things you hate, and I want you to let me drive it. And he claims he did this for like 250 cars in his parking lot. That's so interesting. And when you hear a story like that, you know, you could be cynical and say, well, maybe he made that up, like it's a founding story, and like it's super compelling.

1:00:03But maybe he actually did it.

1:00:06Bill Gurley:And maybe he was a first principal learner, like going after this new thing. And the irony is that's an activity that anyone at GM or Ford or Chrysler or whatever could have done and probably haven't. No chance. Like this kind of base rate start at zero kind of thing. And when you see that, there's a notion that I get accused of being like an agent of the CCP sometimes just because I try and be eyes wide open. I'm not trying to be on anybody's side. But when you meet someone like Lei Jun and see that and then you hear this idea, oh, you know, the Chinese are just copycats. They're not innovators.

1:00:49It's just not true. It's just flat out not true. I haven't been to China.

1:00:54Bill Gurley:And if you see these reviews of this car and you see the founding principles that work inside of Lei Jun's head, he's special. You know, he's very, very special. Every bit as special as Toby or Steve Jobs or Jeff Bezos. And it's valuable to know that, like as opposed to sticking your head in the sand and not knowing that. Of course. Yeah. And also, I mean, if you haven't been to China, but once you've been there, I mean, I remember I first went there like probably like 15 years ago. And I remember back then thinking the light shows were crazy that they had over – there was the – whatever the main thing is in Shanghai where they have like the kind of – The bun.

1:01:37Right. Yes. European on one side and the bond is on the other. And I had to live there for a few months. It was not my favorite place to live 15 years ago. It was really polluted back then. It's very different today. Yeah. But even then, I remember thinking, no, no, no, this isn't copying. I mean, this thing's different here, just in the same way you feel, I think, if you go into Japan for different reasons. No doubt. But it kind of has this idea that I really liked from you too, which is, have you ever seen the, I can't remember who said it, but that was a basketball player. And he was like, you don't get paid for the game.

1:02:11You get paid to practice. Like the game is the reward. The practice is what the pay is for. And then you have a quote in here, which is that the will to win is not nearly as important as the will to prepare to win from Bobby Knight. And so I want your take on preparation. Like how important is it? Do most people do it? and how should you prepare to win? You know, there's an anecdote in the book that... When you want your spring break to feel like... And your kid's pool day to feel like... And your hotel bed to feel like... Ooh, and room service to feel like... Because at Hilton, hospitality feels like...

1:02:54Your cabana's ready. Would you like fresh towels? It matters where you stay. Book now at Hilton.com. Hilton, for this day.

1:03:27$75 sponsored job credit at indeed.com slash podcast. Terms and conditions apply. Kobe Bryant, after winning, I think his fourth championship and third MVP, I'm probably getting those wrong. It might be a different number, but some ungodly level of success in that off season, reached out to Hakeem Olajuwon and asked if he could come to Houston. So not only did he ask, but I'm coming to you to learn Hakeem's footwork in the post.

1:03:57Bill Gurley:So this is a guy, unbelievable, you know, unbelievable forward, you know, easily could be a point guard, but he's now going to add to his game the ability to do these post moves. And he went down there and did it. And, you know, the press showed up and they interviewed Lajuan about it and all. But it's a powerful statement that someone with that much success was trying to find an area where they could improve and was willing to kind of go to that length to go figure it out. And I ask anyone who's chasing any career, are you like that? Do you go home and learn on your own time in your field? And I think a lot of young adults who go through this system, which I don't like, and I think has gotten perverse.

1:05:02Bill Gurley:Do you learn at home on your own time? And I don't think the answer is yes. And I think it's partially because they've been through such a pressure cooker and grinder that they want to believe, oh, it's over. Man, I'm glad that's over. Like, oh, I'm going to go get a job. You know, that learning's over. And when learning feels forced, it's not fun and it is a grind. We had a chance working on the book to talk to Angela Duckworth and 10 years after she released Grit, which said it's 50 % perseverance and 50 % passion. She said if she could do it over again, she'd weight passion way more highly than perseverance because we've taught young adults to grind.

1:05:48Bill Gurley:We've taught them how to grind. You know, they're the Eagle Scout and the 1500 plus SAT and they just, you know, achievement, achievement, volunteer, volunteer. But we didn't allow, we took away the opportunity to explore and learn and discover and find what they love. And when you love something, like I got to believe Kobe did playing basketball, that that decision to go do the elage one thing didn't feel like work and i'm coming back to your point about will to practice like like if you adore something like danny does restaurant we talked to danny um last year finishing up the book i was working with a co-writer and researcher that's why i keep saying we and he was just coming back from a trip to europe with all his top chefs like they went and went to all the new top you know michelin places and took copious notes and like a learning journey like he's still doing it you know and i don't think that's possible if you don't adore the field you're in like if if you don't have this immense emotional connection to what it is you don't study it at home and one of the things that became quite aware to me especially when we translated this from just a video presentation, a book, and did a whole bunch of research.

1:07:14Bill Gurley:We probably read 100 more biographies. The people that are wildly successful, they do this intuitively. They're just out learning constantly about what's new in their field, and it doesn't feel like work. It feels like fun. And the other thing I would say that's also something we discovered in the book, a lot of people turn hobbies into careers. Because that's the thing. The hobby is the thing they're studying for fun. And one thing I hope with this book is that it gives more people the permission to go do the crazy thing they love. Because I think the system doesn't want to support that for well-intentioned purposes.

1:08:01Bill Gurley:But I think they're going to be more fulfilled and they're going to impact more people if they go give that a shot. I really do. It's so good. It's also so contagious when you feel another obsessed person. No doubt. And for some reason we were sold this lie that, oh, why don't you just take some time off? Why don't you have work-life balance? Why don't you go do something not related to what you do? Well, if you're actually really into what you do, that sounds so uninteresting to me. You know what I find so uninteresting? just any movie anything on netflix you know going out and drinking and partying because i want to forget my life and what reality is it's so uninteresting but if i didn't get lucky enough in many ways to do things that i love to do i bet i would find all those things really interesting yeah well look i i mean i kind of have two reactions to this one i don't want to condemn people.

1:08:54Bill Gurley:It may be that you just have this perfect family life, this incredible church community. You may truly love those things so much and feel that that's not a career and that you're going to do your best in your job and then get home and love those things. And I don't want to condemn that path. I really don't. But I think far too few people look at their career as something they could love. And so that's what I'm after. If you have an inkling, if you just have this suspicion, maybe I should be doing something else, try my book. I want to offer an alternative door for you to think about. But don't you also, I think we also have to be honest with people about, have you ever met somebody that was semi-curious and not obsessed, but one in huge, huge, three standard deviation ways.

1:09:54No. So it's like, you're not condemning it at all by saying live a beautiful life where work isn't the center of it, no prop.

1:10:02Bill Gurley:Right. But don't assume you're gonna go become a world changer. No, you should assume that this other person we're describing is competing with you. Oh, that's scary. That's what you should assume. And yeah, this study, you mentioned like watching Netflix. I think it's like a really interesting test of whether you've identified this thing you should go chase. Would you study it instead of binge watching Breaking Bad? Like, would you, does it compete with that on that level? For your, the person in your shop that played with Clawbot until all night, the answer is obviously yes. Right. And so it's a great, it's a great way to test whether you've found it.

1:10:48Bill Gurley:And that's the first principle in the book. It's the hardest part, like just knowing what it is. That is hard. I think it's the hardest part. I only have a few more questions, but one of them, I have like, we hear a lot this idea of like the young, I mean, gosh, you were in a movie about it. It was like, you know, young founder, crazy, out to change the world. And sometimes I think people feel like it's too late. Like, what if there's somebody listening right now that's like, I'm mid-career. Like, I don't know if I can just go do what I love, Bill. like must be nice you and Cody talking about this, you know, not for me.

1:11:22What would you say?

1:11:23Bill Gurley:Well, I have two reactions to it. One, Daniel Pink wrote this great book about regrets. And one thing that he has studied academically, and not just in the U.S., across tons of different geographies, people as they get older, the thing that causes them the most rumination and anxiety is regrets of inaction. They don't regret the mistakes. Humans are remarkably forgiving to themselves. Oh, took a wrong turn, learned a lesson, never do that again. Like they don't dwell on it. But the thing they never tried, they dwell on. And the older they get, he has this great graph, the older they get, the more it weighs on them.

1:12:05Bill Gurley:So if you can keep that in your brain, there's a great video you can go see of Bezos talking about being in Central Park, thinking about whether he should go start this online bookstore or not. And he came up with what he said it was nerdy, but he admitted it anyway, called the regret minimization framework, where he imagined himself being 80 and used that to reflect on the decision. And I think it's awesome. Like one of the ways I walked away from two successful jobs in pursuit of my dream job was saying to myself, do I want to be doing this 30 years from now? Um, so that's my first thing I would tell them, maybe go read Daniel's book and like get in touch with, are you, are you sure you don't ever want to do this?

1:12:52Bill Gurley:And then the second thing I would say is, um, there's a special chapter in the book for these people called never too late. And I walked through, I give an example of about 20 people that, that started really late in life, but I walked through four examples, including our, our fellow Austinite, Mr. Burt Beveridge, better known as Tito, that had been a seismologist and a mortgage broker and started thinking about launching a spirit company at the age of 40 and is the most successful spirit in North America today. And I have a bunch of friends that are friends with him. I'm not friends with him, but they just say he's an incredible human.

1:13:33He's super obsessed with his craft to this day, even though he sold, didn't he?

1:13:38Bill Gurley:No, no. No, he still owns it. Not only did he not sell, this would be great for your audience. He's 100 % of the equity cap table. I do love that. I do love that. I've never raised capital for this company. The other day somebody asked me why. You know, we get approached, whatever. And somebody asked me why. And I said, like, I have my friend Dino who runs a company called Sironic. They're building ports and autonomous ships. Yeah, I'm familiar with the company. Yeah, of course he's got to go raise a bunch of venture capital because he is building these huge things that could change, you know, infrastructure trajectory.

1:14:11The cool thing about media companies is this is just another type of leverage. And so I could put capital leverage on top of what we're doing, but all the infrastructure is already built. I don't have to build a port. Zuckerberg built it for me. All these other people did. And then I get to plug our little ships into the infrastructure that already exists. And so you don't always have to go raise capital. And in fact, I love a venture capitalist that says, hey we're you actually we're not for everybody and most people most people shouldn't yeah and i invest in in in startups so like i i want the best ones to win too yeah but i also want people to keep their company as much as they fucking can as a no doubt no doubt i guess that's where i want to kind of end maybe here so you've like i loved one of the articles you did back in the day about uh the business model of uh giving away a dollar uh and getting paid 85 cents yes and i'm curious for you today, like, what do you see in this atmosphere of venture capital today that you're like, we got to be careful on this?

1:15:14Because you've been a canary in a coal mine a few times.

1:15:16Bill Gurley:Yeah. So in the AI space, there's so much hyper competition. Well, first of all, the venture capital world via this competition I talked about has evolved to a place where the biggest funds now proactively knock on the doors of the companies they want to invest in and offer them money. So the days when the company would run out of money or get close to running out and decide, oh, we're going to go raise now is over. It's preemptive. It's 100 % preemptive. And so you get a phone call that says, we want to put 300, 400, 500 million into your company. And you may be like, well, I've got all the capital I need.

1:15:57Bill Gurley:No thanks. But then they say, okay, we're going to go put it in your competitor. And so there's this global arms race. I lived it in the Uber Lyft thing, but now it's true in every single sector. And the reason this gets to your question is once you're in that place, and I would say AI coding is in this place right now, no one prices to cost anymore because they're definitely afraid of losing market share more than anything. So they price to get market share. They don't price to cost. Now, one day, they'll have to price the cost. One day. And it will be a messy journey from here to there. And I fear that that's a reality in almost every sector at this moment in time.

1:16:44Bill Gurley:The venture industry used to get reset every 10 or 15 years. It'd just get walloped on the head. And the number of firms would get cut in half. And everyone would learn their lessons. And we were supposed to have a reset. when AI came along. It had kind of started. And then this huge disruption, everyone gets excited, money flows back in, and we never had it. And so I can't predict when it will happen. It will probably be a long time from now, but it will happen. There will be a correction. It'll be messy. And that's why I would stay away from SPVs. To circle it all up. I love that. You've essentially done a scary thing, I think, that a lot of people probably couldn't even understand, which is you take your money plus other people's money.

1:17:34You're the fiduciary of this money. And then you give it to somebody else. And you have some controls, but not all the controls. And especially in startup land, it's not like private equity where we can kind of run the show. Oh, yeah, you guys have control.

1:17:46Bill Gurley:We can, which is good and bad. It's very different. It's wildly different. Right. So I'm just curious, how do you manage that? How do you manage being so you know, trying to be founder friendly and trying to tell these young people, go for the moon, you know, hit the stars while talking to you, Timco, about the fact that you're going to fiduciary their capital. I think it's really hard. Like, I used to use this metaphor, which I don't think makes sense to anybody, but I'll use it anyway. When I was young, and I'm almost 60, sometimes a friend of yours had a bicycle that was a little old and rickety and not all together.

1:18:26Bill Gurley:And the handlebars weren't in perfect connection with the front wheel. There was slop in it. And so you kind of thought you were steering, but you just had to oversteer a lot and you kind of went down the road in a janky way. And it's a lot like that. You don't have the steering wheel and your ability to influence is limited. Um, and so you do everything you can to earn the respect of the founder and, and respect is a different word than affection, I think. And it's hard, like it's super hard and the great ones have figured out how to do it. Um, And by the way, it's even harder with sycophants living in the later stage investment rounds because they come in and say everything the founder wants to hear.

1:19:22And that makes it even harder because here's somebody with a lot of money showing up who's not doing what you're doing. You know, and so it's a craft for sure. Was that wild when the movie came out about Uber and you and Travis and you were managing this bicycle in so many ways?

1:19:43Bill Gurley:It was weird. It missed some points. I imagine. In the very first scene, they're in this super fancy office. I can assure you Uber started in the dingiest, smallest of offices like most startups do. and I already talked about how determined Travis was. He's one of the smartest people I've ever met. He's one of the hardest working people I've ever met and I don't think the film captured that element. It was more a vilification kind of thing. So part of the reason it wasn't overly weird is it wasn't so accurate and that allowed me to view it in a different way, if you would. Yeah, that's actually kind of helpful.

1:20:29Yeah. Because I think, I know, I've never been at the, I've been in the center of some things online, but whenever I have been, I don't know that our brain can actually disassociate what is really happening in real life versus when everybody's talking about you online.

1:20:43Bill Gurley:I thought the WeWork film did a much better job of capturing some of the nuances, like around Masa. Yeah. And how Masa putting money in causes randomization and craziness. You know, Lito in the character, and Lito did a ton of work for that role. I actually talked to him. And I don't know how they didn't win awards. Yeah, I agree. They were so good in that. But the character is screaming, Masa wants me to be crazier. And that was real. That's how it really was. Well, and also, you know what I took away from that one? He was so brilliant in so many ways, too. Like, and so many people have vilified him.

1:21:22Adam's the force of nature. I've never, this, maybe we can end with this anecdote, but I remember where I was when he presented to us. Now, keep in mind, Benchmark's never done a real estate transaction in the history of the firm. And we're about 30 minutes into the presentation. This is Series A, right? So there's almost nothing there. And I knew we were going to do the deal without even talking to the partners. Because I mentioned when we started, we talked about salesmanship. And he has a level of salesmanship that I had never seen before. Never seen. Like unit of one. And so you take the flyer.

1:22:04Like you have to take the flyer. This is similar to that. But what I took away also was like, I think his wife is portrayed kind of in a gnarly way sometimes. But there were a couple moments where I was like, yeah, maybe not the best advice, but also fucking brilliant. And she seemed to push him to be better too. So it almost seems like these founders and maybe the people around them have to be on this edge between the two. Yeah. I'm not going to name any names, but there are some very successful founders that eventually reigned it in and got it together. but where you could have easily seen them going over the edge, you know, at different points along the way that didn't.

1:22:45But I think you're right. Being on that edge may be important. Yeah. Bill Gurley, this is so amazing. I so enjoyed. I mean, Dave and I have been reading your book. We have all these notes on it. And I also think it's really cool. At first, I called Tim Ferriss, our mutual friend. And I was like, Tim, I want more stories from Bill. I was like, I want Bill to tell me about this and this. And he said like two really lovely things about you, which is one, he was like, he's like a pretty humble guy. So he doesn't like, he's really not going to like, quote unquote, spill the beans on all this stuff.

1:23:15And then two, he was like, he's so smart. So we'll talk about whatever you want. But he goes, think about it for a second. When one person has been really successful in one thing that they've done for 30 years, how many chapters are in that book? And I was like, I think it's really cool that you put a bunch of chapters in this book and that you talk about something that can really help the next generation, not even the superheroes, but like everyone. So thanks for writing the book. Thank you for being on the podcast. Thanks for having me on. It was so useful. Appreciate it.