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

My new book Own Or Be Owned is out now! I wrote Own or Be Owned to answer one question: How do you make more money, less miserably? I broke it into the 12 Profit Levers… The 12 levers I've seen determine whether you print cash or hate your life. Check it out: → https://contrarianthinking.biz/oobo_bigdeal The rules of career success just changed. Hard skills matter less. Credentials matter less. And playing it safe? That might be the riskiest move of all. Bill Gurley has backed Uber, DoorDash, eBay, and Snap. He's spent 30 years watching who wins and who gets destroyed. In the AI era, that gap is about to become a canyon. In this conversation, Bill breaks down the exact skill stack that makes you anti-fragile: why unbridled determination beats raw intelligence, why salesmanship is the most compounding founder skill nobody talks about, and why the conveyor belt from college to consulting is now the highest-risk career path in existence. You'll learn the Jeff Bezos hiring filter for people who will build something come hell or high water, why AI is a jetpack for the self-directed and a threat to everyone else, how open-source Chinese AI models are a bigger disruption than most realize, and the regret minimization framework Bezos used to decide whether to start Amazon. If you've ever wondered whether you're on the right path — or how to stand out when everyone has access to the same tools — this one will permanently change how you think about winning. Bill Gurley's new book "Runnin' Down A Dream: How To Thrive In A Career You Actually Love" is out now, check it out here: https://www.penguinrandomhouse.com/books/769256/runnin-down-a-dream-by-bill-gurley/ Ready to turn your newsletter into your career? Head to https://beehiiv.link/uth844 and use code CODIE30 for 30% off your first three months. Take your personal data back with Incogni! Use code BIGDEAL at the link below and get 60% off an annual plan: https://incogni.com/bigdeal ___________ ___________ MORE FROM BIGDEAL 🎥 YouTube: https://www.youtube.com/@podcastbigdeal 📸 Instagram: https://www.instagram.com/bigdeal.podcast 📽️ TikTok: https://www.tiktok.com/@big.deal.pod MORE FROM CODIE SANCHEZ 🎥 YouTube: https://www.youtube.com/@codiesanchezct 📸 Instagram: https://www.instagram.com/codiesanchez 📽️ TikTok: https://www.tiktok.com/@realcodiesanchez OTHER THINGS WE DO 🌐 Our community: https://contrarianthinking.typeform.com/to/WBztXXID 📰 Free newsletter: https://contrarianthinking.biz/3XWLlZp 📚 Biz buying course: https://contrarianthinking.biz/3NhjGgN 🏠 Resibrands: https://resibrands.com/ 💰 CT Capital: https://contrarianthinking.biz/4eRyGOk 🏦 Main St Hold Co: https://contrarianthinking.biz/3YfGa8u Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  UKG is the workforce operating platform with unified HR, payroll, and workforce management, built to solve the unique challenges of frontline work. Powered by People First AI and decades of labor data, UKG turns workforce intelligence into real-time decisions around staffing, pay, compliance, and productivity, enabling every worker to confidently take action as work happens. Because when work works, everything works. Learn more at ukg.com/work. UKG, HR, Pay, and Workforce Management.

• 0:30Codie Sanchez?

  What do you see in founders who are winners or losers?

• 0:33Speaker 02

  I borrowed this one from Jeff Bezos. He said, "I only look for one thing, determinism that's unbridled."

• 0:39Codie Sanchez?

  Bill Gurley is a legendary venture capitalist, early investor in Uber, DoorDash, Asana, eBay, Snap. And today, we're breaking down who will actually survive in an AI-dominated world and the skill stack that makes you anti-fragile instead of obsolete. Kind of want to go to AI.

• 0:53Speaker 02

  I think AI is a superpower. There's never been a better time in the history of the world. It's insane, the opportunities that's out there for you. Kobe Bryant, after winning his fourth championship, asked if he could come to Houston to learn Hakeem's footwork in the post. It's a powerful statement that someone with that much success was trying to find an area where they could improve. I ask anyone who's chasing any career, are you like that?

• 1:23Codie Sanchez?

  The question I have for you is like, what do you see in founders who are winners or losers?

• 1:29Speaker 02

  One element of being a great founder, and we're talking about people that can not just start a small company, but one that can grow it into a much bigger company. One element is salesmanship. And it's not something that you hear a lot of people talk about. But in order to grow a company to a very large size, obviously, you have to sell customers. But you also have to sell employees, and you have to sell partnerships, and you have to sell incremental investors. And you're just out, and you own the brand of the company, which you're likely promoting, that nauseam. And if you're not good at that, it'd be very difficult to outrun the other company that may be competing for that. So that's one.

• 2:14Speaker 02

  It took me probably my entire 25 years to come to terms with this. But you do, I think you really need to be great at product. Like, you just have to be. And I used to think, I used to try and convince myself that wasn't true. And I learned the lesson the hard way a couple of times. And the, the, the really great founders have this instinct, not just for the best practices for products today, but, but where those are going to go when the new technologies allow them to shift to the next place. And that really matters. Um, many great startups have a go to market advantage. They've figured out some hack to get to customers faster. And so that's another element that could

• 2:55Speaker 02

  be important. Um, and then I borrowed this one from Jeff Bezos. He, I asked him once, how, how in the world do you do so many amazing angel investments while you're running Amazon? And he said, I only look for one thing, which is that this person's going to go do this thing they claim they want to go do come hell or high water. Like whether I'm involved or not, like this kind of, um, determinism that's unbridled. Like it's just, I, there's, there's nothing that's going to stop me from doing this. And he has a way of sensing that. Um, so that's a, another good, good tip perhaps.

• 3:32Codie Sanchez?

  Do you have a way of sensing if somebody is just going to stay in it until they either do it or they break them?

• 3:38Speaker 02

  There's a couple of things you can look for, like, did they fall into it, um, opportunistically? Cause then they might not, it might not be there, you know? Um, and some people, I remember, I remember when we did the first Uber investment, um, Travis, his, his first couple of companies, one of them, I think ended up in bankruptcy. The other one, they like got money back. But it was pretty obvious he hadn't touched the brass ring and really, really, really wanted to. And he could sense that this thing was going to work, like way bigger than

• 4:18Speaker 02

  the first two he was on. And I could, I could just tell he wasn't, he wasn't gonna, you know, he wasn't gonna not lean in as hard as he possibly could. You could feel it.

• 4:29Codie Sanchez?

  Yeah. It's funny. We have a founder, I won't say his name, but he's a stud, but you know, he now has a company. It's worth multiple, multiple billion dollars. And, uh, and we jokingly say, he's either going to be a trillionaire or he's going to go to prison. It's like.

• 4:43Speaker 02

  He's so determined.

• 4:44Codie Sanchez?

  Yeah, there's just no way.

• 4:46Speaker 02

  Josh Wolf of Lux Capital has a saying, chips on shoulders, put chips in pockets.

• 4:51Codie Sanchez?

  Oh, that's good.

• 4:53Speaker 02

  Yeah, yeah, just this and that. It's a little bit of a pivot from the like umbrella of determinism, but but kind of this like the chip on a shoulder thing is is another example of that determinism. Like, I got something to prove. I really have something to prove.

• 5:10Codie Sanchez?

  Yeah. Do you? What is the opposite of this? Like, you had a blog post I love.

• 5:14Speaker 02

  And by the way, a lot of that stuff I mentioned, like I nowhere in there did I mention the idea like or the specific business. And we've seen incredible businesses be built by great founders who have pivoted 180 degrees from the original idea.

• 5:31Codie Sanchez?

  Yeah.

• 5:32Speaker 02

  Discord's that way, for example. And and, you know, Slack was famously that way. So the the the person matters more than the concept.

• 5:44Codie Sanchez?

  How did they know when to give up on Discord for answer? How do you know when to give up on an idea?

• 5:48Speaker 02

  I think you can reach a point where none of the math works, you know? The team that built Nextdoor originally had built a website for sports enthusiasts. And it was out there, it had a million users, but based on ad rates and everything and the growth rate, it needed to be 100x bigger. And that looked impossible, you know? And you tilt and tilt and tilt and tilt. Yeah.

• 6:18Codie Sanchez?

  So you don't want to get tied to the idea. You want to get tied to

• 6:23Codie Sanchez?

  an outcome like.

• 6:24Speaker 02

  I was fortunate to be at a place at Benchmark Capital where we were and they still are competing to be the best in the business. And the game's a little different at that level because you're looking for the grand slam home run outcomes and you're not.

• 6:42Speaker 02

  You know, it's not a game of IRR. It's not a game of, uh, it's more like a mid-market PE where you need, you know, you can only have one failure. The winners are so big at that level, you could have 80% of your portfolio fail. So it's a game that's a lot riskier and you're searching for the really big outcomes. So some of the decision making is different.

• 7:04Codie Sanchez?

  Yeah, it's really important to say.

• 7:05Speaker 02

  Yeah.

• 7:06Codie Sanchez?

  Yeah, you don't need to have, if, you know, because most people don't want that life. Most people actually want, and it's, I imagine it's pretty miserable. I mean, we run a couple of pretty big companies from our standards and it ain't easy.

• 7:18Speaker 02

  I've, I've shared two thoughts with founders that relate to what you're saying. One, um, I have the unfortunate, I, I had the unfortunate, um, position of telling founders when they achieve some level of success, that it only gets harder going up. And like, it just keeps getting harder. And if you think growing a hundred million dollar company is hard, try growing a billion dollar company. And the expectations go up and the number of people whose, um, livelihood are counting on you, the employee base goes up and it just gets harder. And, um, the only solace I have for them is I always tell them, if you're going to look up the ladder, make sure you look down the ladder. You know, it's just like,

• 8:02Speaker 02

  make sure you celebrate how far you've moved. Cause I, I talk to a lot of, uh, people who are probably in the top two percentile of all startups and they're pretty stressed about not being, you know, above themselves. And the other thing I tell a lot of founders, which I think may really relate with your audience is, you know, venture capital, it may not be a good fit for your business. And, um, very oftentimes in venture capital, especially if you're partnering with a firm like I just described, where they're trying to have these massive outcomes, you know, a series A quickly becomes a series B quickly becomes a series C. And before you know it, the founder's equity is down around 10% or lower.

• 8:44Speaker 02

  And, you know, if you can self-fund your business, you know, you can exit at thirty to fifty million dollars and make lifetime wealth. But if you start down this path and get down to ten percent, you now need to sell for half a billion to get that same outcome, which is a lot harder to achieve. And so, like, just make sure that that's what you need, you know, and make sure that that's what you want. I actually think that there are far more companies that want to do tuck in thirty to fifty million dollar acquisitions that want to do than want to do, you know, half a billion. Like, like, it's probably a hundred x easier to get that type of deal done.

• 9:26Codie Sanchez?

  It's a really good point. You kind of have had this history of saying some of the hard things that's not consensus in VC continuously.

• 9:34Speaker 02

  Yeah.

• 9:34Codie Sanchez?

  I was going through your old blog that, you know, you've had for what, thirty years? Last couple of years, maybe a little bit less, but there were, there were like two blog posts I really, really loved. And one I remember when it came out was, it was actually about red flags in companies. It came out like two weeks after FTX, basically. So it was like incredible timing. And you basically talked about all the reasons why. And I had like, God, I have a quote in here from it that I just want to read. It was, "I have over forty years of legal and restructuring experience, never in my career seen such a complete failure of corporate controls and such a complete absence of trustworthy financial information as occurred here." And so what I would love to know from you is like, what are the biggest red flags in business?

• 10:19Codie Sanchez?

  And what did you see in that deal that you were like, guys, how did you miss this?

• 10:23Speaker 02

  Well, by the way, it's tricky because I just told you that there are firms out there that want to find the biggest grand slam home runs they possibly can. And so, the best way to make sure you have exposure to as many of those as you can is to be and look as founder-friendly as you possibly can. And, and so if you combine hyper-competition at the investor level,

• 10:50Speaker 02

  From the time I entered the venture career to the time I left, competition only went in one direction. It increased and it's more competitive today than ever. And if you, if you have that hype for competition and if the best way to, to ingratiate yourself to a founder and potentially get a new deal is to be as friendly as possible, you create a scenario where this is very likely to happen, like super likely to happen. And so I don't know that there's a way around it because the, the, the option is like, I think that the compet- the competitive level is so high that you're going to test this boundary constantly.

• 11:32Speaker 02

  Like you're just going to test the boundary and some, look, some of the best founders are very determined, we use the word deterministic and aren't looking for constraints. And so it's, it's kind of ripe for this to happen, you know?

• 11:47Codie Sanchez?

  That's true.

• 11:47Speaker 02

  But, but, but it gets rationalized, you know? And so I was actually at a dinner with some of the FTX investors about two months before it blew up. And I said, and I asked all the questions that are in the red flags and they were aware of all of those risks, but you know, didn't, didn't have a way to manage it.

• 12:08Codie Sanchez?

  Fascinating.

• 12:09Speaker 02

  Yeah.

• 12:10Codie Sanchez?

  Yeah. You know, on the other end of the spectrum.

• 12:12Speaker 02

  But it's okay. I mean, look, it's, it's a, you know, everyone's wearing their, what would you say, big boy underwear in this game? And so not, not to, I hope that's not gender biased, but like, um, this is one of the reasons why, there's a number of people that, that want to push to have everyday retail investors be able to invest in these types of companies. And this is one of the reasons why I'm somewhat like cynical about that idea because the people that are doing this kind of know the risks they're taking, but I'm not sure that everyone would understand, including the failure rate issue. You know, I, I, these, these, these pass the hat SPVs that are happening everywhere, special purpose

• 12:54Speaker 02

  vehicles, you're probably aware of this, like people are going to get. Burned.

• 13:00Codie Sanchez?

  Yeah. Well, why don't you explain, why don't you explain a special purpose vehicle and how somebody might say they invested in SpaceX, but you know, ridiculous fees and at a wild valuation.

• 13:10Speaker 02

  So let me back up for just a minute because I think it's important to frame it. In a venture capital fund, so this is a fund that, that limited partners are going to invest in, which are traditionally endowment, university endowments, fellowships, that kind of thing, foundations. That venture capital firm will have an agreement with these investors that includes something called a look back. And what the look back says is if you take money from the first three winners and then don't return anything else, a bunch of losers, you owe us back what was in those losers. So there's a, there's an investment agreement that kind of looks at the fund and the portfolio holistically.

• 13:55Speaker 02

  An SPV, special purpose vehicle, is when a investor is representing a group of other investors for a single investment and it doesn't have a look back and there's no portfolio. And so they'll take fees, not always, but sometimes they'll take management fees and a rake, some, some form of carry on this single investment. And if any VC could strike a deal with their LPs where every single investment was a SPV, they would do it. But they don't do it. And that's kind of the point. And there's a concept in gambling in Vegas called a free roll.

• 14:38Speaker 02

  And I often think about from the GP's perspective, the person underwriting the SPV, the one trying to talk you into investing in it, I think they got a free roll. Cause if it works, they make money. If it doesn't work and they got fees, they still make money and they got nothing in it. Like, you know, and so the only way I would ever consider an SPV is if the, the underwriter is putting 50% of the money in or more.

• 15:06Speaker 02

  But they're they're probably not at all. And so and and these are, these have become particularly popular in the last year or two. And and I would just like, it's funny, this whole AI thing, like the the ups and downs that have happened. The uh, the funny thing is the the the best bet all along has just been the index, like the S and P index, because you were exposed to AI because Nvidia became such a large part of it.

• 15:34Codie Sanchez?

  Or now Apple with hardware.

• 15:35Speaker 02

  Yeah, you had all these big companies that were already overweighted in the index that were AI exposed. And here now, where we have the fear of AI starting to cause valuations to crumble, the S and P is has performed pretty well. And if you're sitting there loading a holding a basket of of like, high tech, new companies, you you got wiped out in the past three months.

• 16:02Codie Sanchez?

  You know, I was looking at the numbers like a couple of days ago, and you know, we've seen massive January layoffs. We've seen like some of the worst jobs numbers since 2009. We've seen like decreasing non farm payroll numbers since basically 2022. We've seen like, you know, decrease in overall job creation in the US. And so I think people right now are saying, oh, my God, forget doing what I want for a living. Am I going to have a job? And you have such a history with these tech companies. Like, one, I guess I would say, how could somebody find a career right now that is safe? Is there a way even?

• 16:35Speaker 02

  So if you look before AI, there was a Gallup poll in 2023, and it's only 23% of people identified as engaging and satisfied at work. 59% did not. And and the other 19 are are like actively unhappy at work. And I think that's interesting, you know, and I I look at what we've done with the traditional career path. And we've created this conveyor belt from it starts, I don't like it starts really early. I think it starts about sixth grade where parents start worrying about their kids' college application and Jonathan Haidt calls it the resume arms race.

• 17:19Speaker 02

  And we just start packing it full of, of extra credit classes and, and cello lessons and lacrosse lessons and all this stuff. And, you know, when I was younger, like, our parents would let us like roam the city for days, you know, and not know where we were. It was just a totally different time. But these kids are so pushed into this pressure cooker. And then they get into college and then you gotta get a job. And, and I think well intentioned parents are pushing kids towards these safe jobs. And, and, you know, I, I've, I've raised three children and I can tell you the intuition to do that is really strong.

• 18:02Speaker 02

  It's like, it's just like built into your DNA. I don't think it's mal, no mal intent whatsoever. You just want them to be okay. You want them to be fine. And so, over the past 30 years, that's been, you know, make them a banker, make them a computer scientist, make them a consultant. And these jobs happen to be under AI threat, but I, I think people weren't happy before that. And I'd like to, if you'd allow me, because I think the AI thing is, is super interesting. I'd like to juxtapose two things for you. One, if you are accepting this kind of conveyor belt process where you're going to go exactly

• 18:47Speaker 02

  in line with how you're told, where how everybody else is doing it, you're going to go be a computer scientist at the best school, you're going to interview with the companies that come there. So you're kind of, you're, you're doing what you're told and you're following where they've told you to go. I think those people, AI is a huge threat because they're like, they don't really know why they're there. They just showed up and they were told to do this and there's a hundred other people around them that look just like them and they're all interviewing for the same job and they're not differentiated and it's scary as all get out. Now, I want to juxtapose that with, let's say you're somebody that has an immense passion for

• 19:29Speaker 02

  something that's very bespoke, where they're out running in their own lane and trying to chart their own course. For that individual, is AI a threat or is it a jetpack? I actually think it's a jetpack because now I can go learn about anything I want. I can go study about anything I want. It's never been easier to learn faster because of this tool called AI. I can build, I can build things with less people. I can write code. I can do videos. And so if you're your own champion and you're in your own lane, I think AI is a superpower. But it's an interesting juxtaposition, right? Like, is it a threat or is it a help? And

• 20:12Speaker 02

  I, I think it's kind of dependent on the game you're playing.

• 20:16Codie Sanchez?

  I actually haven't thought about it that way, but it makes all the sense in the world. You can almost feel the people who are excited by AI because they want to practically apply it right now, immediately to something.

• 20:25Speaker 02

  Yeah.

• 20:26Codie Sanchez?

  And the people who just think, oh, Lord, I used to do X task. Now somebody else is going to do the task.

• 20:31Speaker 02

  Right. There, there's a, there's a funny story that I think's relevant, which, um, I think, I think it was Bjorn Borg. There was a tennis player who retired very early. I think it was Bjorn Borg. And he, when he retired was the day, the kind of final years of the wooden tennis racket. And he decided to make a comeback. I hope it was him. I hope I got the name right. And about five years later, and everyone had switched to these big graphite rackets. And he refused to use one because he was used to the tool he had. And he got obliterated, like, wasn't even close. And, you know, I, we, there are many anthropologists that have studied the fact that humans evolved with their tools.

• 21:16Speaker 02

  And so you could, you know, who's, who's more fit? You know, someone in Naked and Afraid, or someone, you know, with a bulldozer and a calculator and a computer. Like, it's, it's pretty obvious, right? And this tool has come along very quickly, AI. And it has capabilities that really matter to make a human more fit, more kind of evolutionarily fit. And if you don't lean into it and figure out how it can most impact the career you're in, you're more likely to be susceptible to being displaced.

• 21:56Codie Sanchez?

  Yeah.

• 21:56Speaker 02

  Like, the best anecdote is to run at it, like, to play with it all the time.

• 22:02Codie Sanchez?

  Yeah, I liked that line you have. I think you had a line, basically, that, like, you have to become the most aggressive user of AI in your field. Run at it, because that's how you keep evolving.

• 22:11Speaker 02

  No doubt.

• 22:12Codie Sanchez?

  Which I love.

• 22:13Speaker 02

  And by the way, that'll be true of the next disruptive technology as well.

• 22:17Codie Sanchez?

  This doesn't feel like, you've seen every technology that, you know, has probably felt this way to the masses over the last 30 years. Does this feel different to you?

• 22:28Speaker 02

  It feels a little different, I think, because it threatens white collar workers so fast. Like, I think a lot of the ways before, so, I mean, you go way back to just automation and factories and, and the agriculture, what happened to agriculture with the rise of machines. And, and look, you know, we used, I think in the, the US used to be 98% agriculture at the top, and it's like, less than 2% now. So, we've survived these things, like, they happen. But this one, this one's unique, I think, and that's why it's created so much anxiety.

• 23:02Codie Sanchez?

  I love Bill's takes on how to find our best careers, because I just read this crazy statistic that by 2030, up to 30% of current jobs could be automated. McKinsey says as many as 375 million workers may need to switch occupations. And Goldman says AI could impact 300 million full-time roles. Here's what no one wants to admit. It's not the robots that win, it's the owners of attention. So when distribution gets automated, when content gets generated, when noise goes infinite, the scarce asset isn't actually skill, it's taste and audience. If you don't own your audience, you rent your income and rent goes up. That's why I've been thinking a lot about email lately. Not the boring kind, the kind that turns ideas into movements. Which brings me to something I've been using behind the scenes, Beehive.

• 23:43Codie Sanchez?

  Beehive is this all-in-one platform for building, growing, making money on your newsletter. But here's what actually matters. It's built for people who already create. So you can publish, you can grow with built-in referral tools and recommendations. You can monetize from day one, like ads, subscriptions, boosts, without stitching together five different tools. You own the audience. No algorithms deciding whether your work gets seen and whether those closest to you actually hear from you. Solo creators are turning newsletters into six and seven-figure businesses. I turned mine into, in some ways, you could say, a nine-figure business. If AI is going to commoditize content, then the move is obvious. Build the list, own the relationship. If you're already creating, or you know you should be, you can actually go to Beehive.com. I asked them for a code for us.

• 24:26Codie Sanchez?

  It's B-E-E-H-I-I-V dot com. And then you can use code CODIE30 for 30% off for three months. I don't think we should wait for the future, we should own something. What are the skills you need to have to win in the age of AI in your mind?

• 24:40Speaker 02

  Immense curiosity, because you have to play with this thing. And you've got to get over the skepticism. I've met some really intelligent people, some of the top academics that I happen to have relationships with, who are just doubters. You know, they find, they get it to hallucinate once, and then they run around and tell everybody about how it gave them the wrong answer. And, boy, that's dangerous. Like, it's just so dangerous to walk around being skeptical in that way.

• 25:12Codie Sanchez?

  Yeah.

• 25:13Speaker 02

  I think it's far too powerful to be that way. But I see it, I see it a lot.

• 25:18Codie Sanchez?

  Yeah, Greg Brockman, I think, had a tweet today that I liked, which just said that, like, taste is now a real skill. And I feel that a little bit. I saw this graph, I should have brought it for you, that I thought was really good. But it was basically like, a little, you know, four-plex. And in the bottom, it was like, bad judgment, good judgment, and then non-AI use, AI use, or high AI use. And then it said, basically, if you have bad judgment and AI use, slop canon, you create a lot of really bad things. Good judgment, lot of AI use, sort of superhuman, you know, 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, you know, we're hiring sort of vibe coders. We're hiring them in every

• 26:03Codie Sanchez?

  single department. We're hiring engineers as well, but we already have engineers that we've been hiring. I've never hired this person. It'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. And 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?

• 26:38Speaker 02

  Yeah, I mean, it may be that both relationships and taste become even more important because of the volume 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

• 27:20Speaker 02

  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. Like, there is an element, people used 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, uh, and knowing you can go to it more often.

• 27:44Codie Sanchez?

  Yeah, that's a good point. Yeah, I guess it's almost like all you'll see an expert with all the ways they know how to utilize a tool, any type of tool.

• 27:52Speaker 02

  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.

• 27:59Codie Sanchez?

  That's my existential drag.

• 28:00Speaker 02

  I haven't built a clawback yet, but probably should.

• 28:03Codie Sanchez?

  My president just did, and he came in wild eyed yesterday. He's like, I've been working on it for the fourth day. I didn't sleep last night.

• 28:10Speaker 02

  I love that.

• 28:11Codie Sanchez?

  But me too. And you know what?

• 28:12Speaker 02

  I love that.

• 28:13Codie Sanchez?

  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.

• 28:18Speaker 02

  Yeah.

• 28:18Codie Sanchez?

  And yet even he is so curious about what's happening.

• 28:21Speaker 02

  Yeah. And you were asking about the, uh, the elements of a great founder, like that part's in there, you know, they can't stand, they have immense FOMO about new technologies, immense FOMO about new technologies.

• 28:35Codie Sanchez?

  That's a great line. You know, um, Chris Sacca had said something really interesting about you, totally off the AI subject, but Chris Sacca 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.

• 29:02Speaker 02

  No, that's not my react. Go ahead, finish the question.

• 29:05Codie Sanchez?

  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. How do you make your words count? How do you get heard by people?

• 29:18Speaker 02

  By the way, that, that thing Chris described is a evolved skill, not, not something that came naturally. And, um, if you read, you know, the stories of the elders, the great early venture capitalists, you'll find a mention of that precise technique.

• 29:39Speaker 02

  And and I probably read those early on, you know, and it's hard like it's super hard like like the human wants to blurt out the best answer first. And you you know, there's this sales tool, um 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.

• 30:09Codie Sanchez?

  That's a great feature.

• 30:10Speaker 02

  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 the other benefit of waiting till the end is you're going to have more information. You're going to be synthesized, you know, 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.

• 30:43Codie Sanchez?

  Yeah, well, we were talking about Rick Rubin before we started.

• 30:46Speaker 02

  Yeah.

• 30:46Codie Sanchez?

  And and I'm obsessed with this one line of his, which is that he is not a producer, he's a reducer.

• 30:52Speaker 02

  Yeah.

• 30:52Codie Sanchez?

  He's always trying to get it down to the core.

• 30:54Speaker 02

  Yeah.

• 30:55Codie Sanchez?

  And that reminds me of you in this way in in meetings. And I know you met, you said you spent time with Rick. What did you 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?

• 31:06Speaker 02

  I was I was kind of on on pins and needles going in because I um 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. It's clear there's something special there. And then you read his book, it's not written like any other book that's ever been written. It's it's Yoda-esque. It's it's small words put together that are profound, but not not obvious in how to interpret. And, you know, some people have told me they've read Rick's book like a fourth

• 31:51Speaker 02

  time. Like, I think it may need that, like to soak in. So I just, I was so thrilled to be there. And 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 being around him. I'm that much of a fanboy, but it was, it was great. He's, he was so prepared. I was so, I, when I was writing the book, I, I was very curious why I did the podcast, because, you know, here's a guy that's remarkably successful in his

• 32:36Speaker 02

  field, probably, you know, arguably the best of all time, but certainly top five producer of all time. And, 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

• 33:18Speaker 02

  it with him, with Toby of Shopify. And I, if Toby talks, you know, anywhere publicly, I consume it within 24 hours. I 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

• 34:02Speaker 02

  Um, 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, where you want to look like a individual and you know how you, you know, the lane you're in, 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.

• 34:35Codie Sanchez?

  Well, I loved a lot of what you said in the book about finding mentors. So that's a question, you know, if 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. One, have you ever called anybody your mentor?

• 34:48Speaker 02

  Yes, they're, they're in.

• 34:49Codie Sanchez?

  Like, did you ask them? Were they like, were you like, will you be my?

• 34:52Speaker 02

  No, I don't think it went down in that way. I didn't say, will you be my mentor?

• 34:56Codie Sanchez?

  Is that a good question to ask? Should somebody ask somebody?

• 34:58Speaker 02

  Probably not. Like, I don't think you should use, it's a very heavy sounding ask, you know? I think, and, 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, 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. Call those your aspirational mentors. Create a file, you know, in whatever digital folder type thing you like to use, Notion or, or Google Docs or whatever.

• 35:42Speaker 02

  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, keep it like a, 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, so the ones you thought you were going to cold call, don't do that. Do the, 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

• 36:28Speaker 02

  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. It's a great way to kind of divide the world into two parts. And, and one day, who knows? You know, when the 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. And he created Shake Shack. That's how most listeners would probably know him. But when Danny decided,

• 37:09Speaker 02

  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. And 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 had, 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? 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

• 37:51Speaker 02

  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, is a truly amazing, fulfilling life experience. Like, it's really cool when that happens, you know?

• 38:08Codie Sanchez?

  It's incredible advice, and I don't think it's given enough.

• 38:11Speaker 02

  Yeah. I have this other thing in the book that I feel compelled to share that I, gives me goosebumps the first time I saw it. When Anthony Hopkins watched Breaking Bad, he, he sent Bryan Cranston this letter about how impressed he was. And

• 38:30Speaker 02

  I don't, 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?

• 38:44Codie Sanchez?

  Oh, that's a great point.

• 38:46Speaker 02

  It just, the, the, the weight that must carry to, to have someone at the top of their, of your field, tell you that, that you did something amazing, like, and it costs nothing, right?

• 38:58Codie Sanchez?

  No, but it's, it's so important because I think these days, like what I see a lot of people doing is, 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. And you're saying, do the opposite, go really deep with few. And then on top of that, they, um, 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, on X, you know, they'll say, well, I've been out of a job for six months 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 in better in most things in life. And you could even maybe, I loved

• 39:39Codie Sanchez?

  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?

• 39:49Speaker 02

  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 a, 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, you're just not doing it right.

• 40:13Codie Sanchez?

  It's true. But you know what's crazy? Don't you find most people still don't?

• 40:17Speaker 02

  Yeah, I think most people don't, but I think that 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 gonna meet that day. Like, I think that like that certainly will happen.

• 40:35Codie Sanchez?

  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. And 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.

• 41:20Codie Sanchez?

  I want some Bill Gurley predictions. Like, 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?

• 41:31Speaker 02

  I, I think this, um, I think everyone is finally now, I think Clawbot actually helped finally push us towards this, uh, this kind of personal assistant concept, this AI thing that's like your, your running buddy that, that I, I really think most people want, you know? And 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 gonna want this so bad. You know, I missed, 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.

• 42:14Speaker 02

  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 gonna happen like for sure.

• 42:43Codie Sanchez?

  I totally agree. Okay, so we're gonna have, we're gonna have relentless little AI reminders and assistance.

• 42:49Speaker 02

  I think so.

• 42:49Codie Sanchez?

  What else do you think?

• 42:51Speaker 02

  Um, I mean, it's so hard to see the future right now because of everything's possible and anything's possible. And, uh, 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'll happen in many, many, many fields as people figure out what's capable, what's possible.

• 43:25Speaker 02

  You know, I think

• 43:28Speaker 02

  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. Healthcare is a good example of that.

• 43:42Codie Sanchez?

  What else do you think that other people might disagree with you about? What else do you like?

• 43:48Speaker 02

  Oh, I can give you an easy one on that. Um, there's a competitive dynamic in China right now and AI models that includes open source. And I don't think the world, especially the, the, the politicians, understand how like unbelievably powerful open source is as a

• 44:13Speaker 02

  As a, as a weapon, like, as a competitive weapon. And if you have ten companies all doing open source, the minute an idea is shared, it's available to the other ten 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 form, there's a, there's a phrase in economics called pure competition that you can look up, uh, on Wikipedia or whatever. And you'll study it if you'd get a finance degree. But in pure competition, no one has an edge. Marginal cost moves to marginal price.

• 44:58Speaker 02

  It's great for consumers. Consumers end up with the lowest price point. Um, 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 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, that, you know, the US with two, you know, proprietary models can stay ahead of China with ten open source ones is very low.

• 45:40Codie Sanchez?

  Fascinating. So what do we do about that?

• 45:43Speaker 02

  Well, I, here's what I fear we're gonna do about it is, uh, this is really off the subject, but what I fear we're gonna do is the two leading players will recognize the threat and weaponize regulation, which is what they're, they've, they started doing three years ago. But, um, no one's funding more lobbyists, um, begging for AI regulation than Anthropic themselves. And, um, And they'll use that to try and deal with the threat, which really going to be interesting is the rest of world. So in for the past hundred years, I think the the US has considered rest of the world their their market like, and that's true in industrial type products,

• 46:28Speaker 02

  but it's certainly true in technology. And if you look at the internet, um, you know, China kind of had a fence around it and the rest of the world use the US products. They use Google and Amazon and Uber and, you know, all these things. And if we pull up this huge regulatory um, wall, you know, it may be the US that has the fence around it this time. It's going to be really interesting. Copyrights is super fascinating thing like, like if the Chinese models don't um, protect copyright and the US 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.

• 47:12Codie Sanchez?

  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.

• 47:22Speaker 02

  I think it would be. This is very controversial, by the way, but I do, I do.

• 47:26Codie Sanchez?

  Well, explain why it's controversial. And even like you could steel man it like Walt Disney would be like, hey, Bill, fuck you.

• 47:32Speaker 02

  Yeah, yeah. Yeah, I I think copyright um, lands harder in people's brain because they think about it as an artist, individual creativity and that that like hits people emotionally. Patents, you know, in the US 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. And 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,

• 48:13Speaker 02

  our firm was lucky enough to be an investor in Red Hat. So we've been investing in open source companies for 25 years. 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, on, on this topic.

• 48:43Codie Sanchez?

  What about like name and likeness and, you know, that in the age of AI? Because so much of AI is just trained on our, you know, let's say

• 48:52Speaker 02

  Look, I recognize the copyright thing, you know, really gets people's skin up. And I, I would just say, you know, a 17 year patent is way too far. Like, 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, I, I visited China in August and I, 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, the higher ups are interested

• 49:33Speaker 02

  in. And open source was in the, the one five years ago. I think that China has been accused of being a, a IP thief for a long time. So it's very natural that they would see open source as a great place to run towards. And they have. And I think people may be making a mistake and not understanding why that, that might actually be the right perspective for a country to want to embrace.

• 50:04Codie Sanchez?

  Yeah. You told, you told a story that I thought was fascinating about

• 50:08Speaker 02

  And by the way, you know, 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 moves your products faster forward. And I'm not convinced, we're getting into really esoteric concepts.

• 50:24Codie Sanchez?

  That's good.

• 50:25Speaker 02

  I'm not convinced that, that having large market cap companies is necessarily a massive advantage, you know?

• 50:32Codie Sanchez?

  Yeah. Well, I think that's

• 50:34Speaker 02

  And it could be a sign of monopoly, right? Which

• 50:38Codie Sanchez?

  I think that's very reasonable.

• 50:39Speaker 02

  Yeah.

• 50:40Codie Sanchez?

  Well, you know, I have a question on that. Like, you know, 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.

• 51:04Speaker 02

  Yeah.

• 51:05Codie Sanchez?

  And 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, you know, basketball player.

• 51:19Speaker 02

  Yeah.

• 51:19Codie Sanchez?

  You're competing in deals. So like, should you try to crush your competition or should you work with them?

• 51:25Speaker 02

  Well, the, the advice in the book, most of it that gets into this topic you're, 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, of all the points that I, that I make. And I, I've found, I've found some amazing stories that, that I share in the book that you can go read. But like, I've found that far too often, humans, and I'm not talking about companies, like, I'm talking about, I'm not saying companies need to have friends, but like, they probably do, but of humans, when they're out trying to climb up the ladder, would do themselves

• 52:08Speaker 02

  a massive advantage if they would embrace a group of peers. So finding five to 10 other people who are climbing the same ladder you are and share, collaborate and support one another. And the number, you know, you, you learn faster, your network is bigger because it's not just your network, it's the group's network.

• 52:33Speaker 02

  If 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, it's, if you haven't been through it, it's really hard to say how big a deal that is. And, um, and you'll have fun and you'll sit like, wait, 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, um, you, one, you're gonna, your odds of success are gonna go way up, but I think you're gonna enjoy the journey a lot more too. I really do.

• 53:13Speaker 02

  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 crowding, 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.

• 53:34Codie Sanchez?

  It'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-competitive or who are anti-collaborative and who aren't actually wishing you the best.

• 53:45Speaker 02

  Stay away from those people. I'll be outspoken, like, uh, there are sharp elbowed people in this world and you can feel them a mile away and let them, 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.

• 54:00Codie Sanchez?

  Yeah.

• 54:00Speaker 02

  Like, don't even invite them.

• 54:02Codie Sanchez?

  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.

• 54:07Speaker 02

  Yes.

• 54:08Codie Sanchez?

  Cause I don't, you know, they don't want to let them in.

• 54:11Speaker 02

  Yeah. And, and look, um, I think I'm all about competing and winning and thriving. Like I, I don't want it to sound like I'm not, but, but you, your odds of getting to, from the bottom rung to the top rung go way up. If you, uh, if you're willing to, uh, share the ride and, and share your best ideas. That's the other thing, like, and one thing I definitely have learned over, over 30 years of working in business, like this thought that you have this unique idea in your head that no one else does is, uh, is far-fetched. Like it really is. And, and, and walking around thinking that is not helpful.

• 54:51Codie Sanchez?

  What's the worst thing somebody can say in a pitch to you?

• 54:55Speaker 02

  That was a bit of a orthogonal question.

• 54:58Codie Sanchez?

  Well, my thought process was.

• 54:59Speaker 02

  Yeah, tell me that, that'll be helpful.

• 55:01Codie Sanchez?

  You, you know, you hear ideas every day and I hear you, 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, which is probably why you come to think that no ideas are unique.

• 55:18Speaker 02

  Yes, yes, that's for sure. And, 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, 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 code and like, and zero, and will be better than, than Salesforce.com? And it won't evolve from all those fields, but it'll evolve in a different way. A hundred percent.

• 55:59Speaker 02

  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. Like it's silly to walk around with that notion.

• 56:14Speaker 02

  It's funny with the thing that I thought of when you asked about the founders. I, I was watching American Idol last night. I've watched it for since season one. It's like my guilty, it's my guilty pleasure. It's like my Hallmark channel. But they've really, 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. Like, you know, my mom almost died and that's the reason I'm starting this thing. And it gets a little cringy, you know, 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 then, and so I started an accounting software. You know what I'm saying?

• 56:58Codie Sanchez?

  So the total addressable market is.

• 57:02Speaker 02

  No, I'm just saying they're not connected, you know.

• 57:04Codie Sanchez?

  That's amazing.

• 57:05Speaker 02

  Be authentic, like be authentic, don't, don't be inauthentic.

• 57:08Codie Sanchez?

  You know, you, you, you have a lot of stories, I think, that kind of show how most of these people who win are authentically obsessed with whatever they're doing. And you told the story about, there was like a Steve Jobs of China and a ridiculous thing he did with Post-it notes on his employees' cars.

• 57:25Speaker 02

  Yeah, yeah, yeah.

• 57:25Codie Sanchez?

  You tell that story because I was like, that is a perfect example of obsession.

• 57:28Speaker 02

  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, a famous and very successful Chinese venture capitalist told me on my last trip. He said, um, every single founder and venture capitalist in China studies the US relentlessly. They watch the, the YouTube interviews, they listen to the podcasts, they study them like crazy. He said, founders and, and VCs in America don't study Chinese. And I said, oh, that's a profound statement, right? Like, just even thinking about that's pretty profound.

• 58:11Speaker 02

  So, in that spirit, I would encourage everyone to go watch the, I think it's the 2024, 2025 Lei Jun 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, as Toby and I, you know, I fortunately met him about 20 years ago and he's, this is his third company since then. But, um, about 10 years ago, he decided to build a phone, um, 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.

• 58:55Speaker 02

  And that car's now in production, sold out. There are some amazing reviews online of Americans who have gotten a hold of the car, including, uh, the CEO of Ford. So you can go watch those and read those to get a, to get a sense of this guy. 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 reapproach it. But he decided that he wanted to drive every car he possibly could to get experience and because he had been driven around by a driver, which is very common in China.

• 59:38Speaker 02

  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.

• 59:57Codie Sanchez?

  That's so interesting.

• 59:58Speaker 02

  And when you hear a story like that, you know, you could, you could be cynical and say, well, maybe he made that up. Like it's a founding story and like it's super compelling. But maybe he actually did it. And maybe he was a first principle learner, like going after this new thing. And, 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.

• 1:00:25Codie Sanchez?

  No chance.

• 1:00:26Speaker 02

  Like this kind of base rate, start at zero kind of thing. And when you see that, there's a, there's a notion that I get accused of being like an agent of the CCP because 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. It's just not true. Like it's just flat out not true.

• 1:00:56Codie Sanchez?

  I haven't been to China.

• 1:00:57Speaker 02

  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. Like.

• 1:01:20Codie Sanchez?

  Of course. And also, I mean, if you haven't been to China, but if, once you've been there, I mean, I remember I first went there like to probably. 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 it's European, right. It's 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, but

• 1:01:50Speaker 02

  Very different today.

• 1:01:51Codie Sanchez?

  Yeah, but even then, I remember thinking, 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.

• 1:02:00Speaker 02

  No doubt.

• 1:02:00Codie Sanchez?

  But, um, but you know, it kind of has this idea that I really liked from you too, which is, have you ever seen the, I can't remember, um, 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. You get paid to practice.

• 1:02:17Speaker 02

  Yeah.

• 1:02:17Codie Sanchez?

  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.

• 1:02:27Speaker 02

  Yeah.

• 1:02:28Codie Sanchez?

  And so I want to, I want your take on preparation. Like, how important is it? Do most people do it? And how should you prepare?

• 1:02:36Speaker 02

  You know, there's an anecdote in the book that

• 1:02:39Speaker 00

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• 1:03:16Speaker 03

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• 1:03:39Speaker 02

  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 offseason, 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. 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

• 1:04:19Speaker 02

  and did it. And, um, and, you know, the press showed up and they interviewed Olajuwon about it and all, but it's a, it's a, it's a powerful statement that someone with that much success was trying to find an area of where they could improve and was willing to kind of go to that length to go figure it out. And, um, I ask anyone who's chasing any career, are you like that? Like, 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

• 1:05:04Speaker 02

  has gotten perverse. Um, 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. Um, 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

• 1:05:46Speaker 02

  over again, she'd weight passion way more highly than perseverance because we've taught young adults to grind. We've taught them how to grind. You know, they get there, the Eagle Scout and the 1500 plus SAT and like they just, you know, achievement, achievement, volunteer, volunteer. But, but we, we, we, we didn't allow, we took away the opportunity to, to explore and learn and discover and find what they love. And when you love something like I gotta believe Kobe did playing basketball, that, that decision to go do the Elijah 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

• 1:06:31Speaker 02

  like Danny does restaurant, we talked to Danny, um, last year, finishing up the book. I, 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, 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, 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

• 1:07:15Speaker 02

  translated this from just a video presentation of book and did a whole bunch of research, we probably read a hundred more biographies. Um, the people that, that, that are wildly successful, they do this like intuitively, like 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, um, something we discovered in the book, a lot of people turn hobbies into careers. Like, cause that's the thing, the hobby's the thing they're studying for fun.

• 1:07:51Speaker 02

  And, 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. But I think they're going to be more fulfilled and they're going to impact more people if, if they go give that a shot. I really do.

• 1:08:14Codie Sanchez?

  It's so good. It's also so contagious when you feel another obsessed person.

• 1:08:19Speaker 02

  No doubt.

• 1:08:19Codie Sanchez?

  You know, 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, 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.

• 1:08:51Speaker 02

  Yeah. Well, look, I, I, I mean, I kind of have two reactions to this. One, I don't want to condemn people like the, it may be that you just have this perfect family life, this incredible church community. You, you may truly love those things so much and feel that, that, that that's not a career and that you're, 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. Like, and so that's, that's what I'm after. Like, if any, if you have that, an

• 1:09:34Speaker 02

  inkling, like if you just have this suspicion, maybe I should be doing something else, try my book. Like, I want to offer an alternative door for you to think about, you know?

• 1:09:45Codie Sanchez?

  But don't you also? I think we also have to be honest with people about like, have you ever met somebody that was semi curious and not obsessed, but won in huge, huge, three standard deviation ways?

• 1:10:00Speaker 02

  No.

• 1:10:01Codie Sanchez?

  So it's like, it's so, you're not condemning it at all by saying, live a beautiful life where work isn't the center of it, no prob.

• 1:10:08Speaker 02

  Right.

• 1:10:08Codie Sanchez?

  But don't assume you're going to go become a world changer.

• 1:10:11Speaker 02

  No, you should assume that this other person we're describing is competing with you.

• 1:10:17Codie Sanchez?

  Oh, gosh. That's scary.

• 1:10:19Speaker 02

  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 you're the person in your shop that played with Clawbot until all night, the answer's obviously yes.

• 1:10:48Codie Sanchez?

  Yeah.

• 1:10:49Speaker 02

  Right? And so it's a great, it's a great way to test whether you've found it. And that's the first principle in the book. It's the hardest part, like just knowing what it is.

• 1:10:59Codie Sanchez?

  That is hard.

• 1:10:59Speaker 02

  I think it's the hardest part.

• 1:11:01Codie Sanchez?

  I only have a few more questions, but one of them, I have like, we hear a lot, this idea of like, the young founder, 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, I'm mid-career. Like, I don't know if, 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.

• 1:11:27Speaker 02

  Yeah. Well, I have two, 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 US, across tons of different geographies.

• 1:11:45Speaker 02

  People, as they get older, the thing that that causes them the most rumination and anxiety is 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 and the older they get, he has this great graph, the older they get, the more it weighs on them. 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 he said it was nerdy, but he admitted it anyway, called

• 1:12:27Speaker 02

  the regret minimization framework, where he imagined himself being 80, and use that to reflect on the decision. And I think it's awesome. Like, and 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? So that's my first thing I would tell them, maybe go read Daniel's book and like, get in touch with, are you sure you don't ever want to do this? And then the second thing I would say is, there's a special chapter in the book for these people called Never Too Late. And I walk through, I give an example

• 1:13:08Speaker 02

  of about 20 people that that started really late in life, but I walked through four examples, including our fellow Austinite, Mr. Bert 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.

• 1:13:34Codie Sanchez?

  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, who's super obsessed with his craft, to this day, even though he's sold, didn't he?

• 1:13:44Speaker 02

  No, no.

• 1:13:44Codie Sanchez?

  No, he still.

• 1:13:45Speaker 02

  Not only did he not sell, this would be great for your audience. He's 100% of the equity cap.

• 1:13:50Codie Sanchez?

  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 Saronic. They're building ports and autonomous ships.

• 1:14:08Speaker 02

  I'm familiar with the company.

• 1:14:09Codie Sanchez?

  Yeah, of course, he's got to go raise a bunch of venture capital. Because he is, he is building these huge things that could change, you know, infrastructure trajectory. The cool thing about media companies is this is just another type of leverage.

• 1:14:21Speaker 02

  Yeah.

• 1:14:22Codie Sanchez?

  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.

• 1:14:36Speaker 02

  That's right.

• 1:14:36Codie Sanchez?

  And so you don't always have to go raise capital. And in fact, I love a venture capitalist that says, hey, you actually, we're not for everybody. And most people, most people shouldn't.

• 1:14:46Speaker 02

  Yeah.

• 1:14:46Codie Sanchez?

  And I invest in startups. So like, I want the best ones to win too.

• 1:14:51Speaker 02

  Yeah.

• 1:14:52Codie Sanchez?

  But I also want people to keep their company as much as they fucking can as a founder.

• 1:14:56Speaker 02

  No doubt, 100%.

• 1:14:57Codie Sanchez?

  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 the business model of giving away a dollar and getting paid 85 cents.

• 1:15:10Speaker 02

  Yes.

• 1:15:11Codie Sanchez?

  And I'm curious for you today, like, what do you see in this atmosphere of venture capital today? That you're like, we gotta be careful on this. Because you've been a canary in a coal mine a few times.

• 1:15:22Speaker 02

  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.

• 1:15:44Speaker 02

  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. Like the, it's preemptive. It's a hundred percent preemptive. And so you, 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. 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.

• 1:16:24Speaker 02

  Because they're, they're, 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 to 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. 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

• 1:17:07Speaker 02

  then this huge disruption, everyone gets excited, money flows back in, and we never had it. And so I, I can't predict when it will happen. It will, 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.

• 1:17:29Codie Sanchez?

  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. You're the fiduciary of this money.

• 1:17:41Speaker 02

  Yeah.

• 1:17:41Codie Sanchez?

  And then you give it to somebody else and you have some controls, but not all the controls.

• 1:17:47Speaker 02

  Yeah.

• 1:17:47Codie Sanchez?

  And especially in startup land, it's not like private equity where we can kind of run the show.

• 1:17:51Speaker 02

  Control.

• 1:17:52Codie Sanchez?

  We can, we can, which is good and bad.

• 1:17:55Speaker 02

  It's wildly different.

• 1:17:56Codie Sanchez?

  Right. So I'm, 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, the moon, you know, hit the stars while talking to you Timko about the fact that you're going to fiduciary their capital.

• 1:18:14Speaker 02

  I think it's really hard. Like, um, 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, um, sometimes a friend of yours had a bicycle that, that was a little old and rickety and not all together. And the, the handlebars weren't in perfect connection with the front wheel. There was slop in it. And so you, you would, you, you kind of thought you were steering, but you, 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.

• 1:18:57Speaker 02

  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. 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. And that makes it even harder. Cause 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.

• 1:19:38Codie Sanchez?

  Was that wild when the movie came out about?

• 1:19:43Codie Sanchez?

  You know, Uber and you and Travis and you were you were managing this bicycle in so many ways.

• 1:19:48Speaker 02

  Um, it was weird. Um, it it missed some points, you know.

• 1:19:52Codie Sanchez?

  I imagine.

• 1:19:53Speaker 02

  They like in the very first scene, they're in this super fancy office. You know, I can assure you Uber started in the dingiest, you know, 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 it wasn't. It wasn't so accurate and that allowed me to like view it in a different way, if you would.

• 1:20:33Codie Sanchez?

  Yeah, that's actually kind of helpful.

• 1:20:34Speaker 02

  Yeah.

• 1:20:35Codie Sanchez?

  Cause I think I I know I've never been at the I've been in the center of some things online, but it whenever I have been. You know, 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.

• 1:20:49Speaker 02

  I thought the WeWork film did a much better job of capturing some of the nuances like around Masa.

• 1:20:56Codie Sanchez?

  Yeah.

• 1:20:56Speaker 02

  Like and how Masa putting money in causes randomization and craziness. You know, Lido in the character and Lido did a ton of work for that role. I actually talked to him and and I don't know how they didn't win awards like they were so good in that. But he's he the character screaming Masa wants me to be crazier. And that was real. That's how it really was.

• 1:21:21Codie Sanchez?

  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.

• 1:21:28Speaker 02

  Adam's a force of nature. I've never this way 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 eight, right? So there's almost nothing there. And I knew we were gonna do the deal like 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.

• 1:22:07Speaker 02

  And so you take the flyer, like you have to take the flyer.

• 1:22:11Codie Sanchez?

  This is similar to that, but I, what I took away also was like, um, I think his wife is portrayed kind of in a gnarly way sometimes.

• 1:22:20Speaker 02

  Yeah.

• 1:22:21Codie Sanchez?

  But there were a couple of 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.

• 1:22:35Speaker 02

  Yeah, I'm, I'm not going to name any names, but there are some very successful founders that eventually reined it in and got it together, but where you, you could have easily seen them going over the edge, you know, at different points along the way, um, that didn't. But I think you're right. You may, you, being on that edge may be important.

• 1:22:54Codie Sanchez?

  Yeah. Bill Gurley, this is so amazing. I so enjoyed, I mean, we have, 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 like mutual friend and, uh, 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, 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, he's really not going to like quote unquote spill the beans on all this stuff.

• 1:23:21Speaker 02

  Right.

• 1:23:21Codie Sanchez?

  And then two, um, 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, the superheroes, but like everyone. So thanks for reading the book. Thank you for being on the podcast.

• 1:23:48Speaker 02

  Thanks for having me on.

• 1:23:48Codie Sanchez?

  It was so useful.

• 1:23:49Speaker 02

  Appreciate it.

• 1:23:55Speaker 00

  UKG is the workforce operating platform with unified HR, payroll and workforce management built to solve the unique challenges of frontline work powered by people first AI and decades of labor data. UKG turns workforce intelligence into real time decisions around staffing, pay, compliance and productivity, enabling every worker to confidently take action as work happens. Because when work works, everything works. Learn more at ukg.com/work. UKG, HR, Pay and Workforce Management.