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Mental Models That Change How You Think | Bill Gurley

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Bill Gurley advocates for systems thinking as a foundational approach to navigating complex environments where small changes can trigger delayed, nonlinear consequences rather than immediate linear results. He illustrates this with the example of dating sites, noting that while increasing profile length initially boosted engagement, it eventually harmed conversion rates due to user fatigue, demonstrating why optimizing single metrics deterministically is often flawed without understanding the entire system. This philosophy extends to his investment strategy, which rests on a bedrock of classic financial knowledge from figures like Warren Buffett and Peter Lynch but has evolved through mentorship to appreciate network effects and growth investing beyond traditional value models. Gurley argues that while many Silicon Valley venture capitalists lack deep finance training, grasping the mechanics of eventual liquidity events such as IPOs or mergers is essential for accurately evaluating early-stage ventures. Beyond financial metrics, Gurley emphasizes the critical importance of combining historical context with obsessive learning about emerging technologies to differentiate oneself in a competitive career landscape. He cites examples like John Lasseter's mastery of animation history and Magnus Carlsen's chess trivia to show how deep domain knowledge provides an edge, while also highlighting that general AI models may eventually dominate but vertical-specific workflows will persist due to specialized data needs. In the realm of global dynamics and regulation, he contrasts China's open-source ecosystem, which fosters rapid innovation through forced knowledge sharing among competitors, with Western duopolies that often seek restrictive regulations to protect market share. Furthermore, he critiques Wall Street's inefficient IPO pricing mechanisms compared to tokenization-enabled anonymous auctions and points out how stablecoins challenge entrenched payment infrastructures by bypassing slow banking settlement times like ACH systems. The discussion also covers the unique traits required for success in venture capital and entrepreneurship, where storytelling serves as a vital tool for founders to recruit talent, raise capital, and close customers while writing cogent documents forces deeper problem-solving skills. Gurley identifies product instinct—the ability to build new categories—as another unfair advantage that requires deep conviction, contrasting this with traditional corporate models by noting how companies like Uber sustained unprecedented burn rates unlike their peers. He explains Benchmark Partners' unique equal partnership structure among five founders as a way to eliminate political overhead but acknowledges the scaling challenges it presents when removing clear leadership roles leads to simplified operations, such as maintaining basic websites for decades despite complex internal needs. Additionally, he observes that venture capital increasingly favors younger investors who can dedicate eighty-hour weeks to mastering niche technologies like esports or YouTube, whereas older generalists often face limitations due to age-related responsibilities. Ultimately, Gurley defines his own success not by continuous accumulation but by the decision to retire when feeling no work remained, signaling a desire for a new chapter in life. He aims to apply his analytical skills honed through venture capital—specifically synthesizing problems and understanding complex issues—to address broader societal challenges rather than remaining solely within traditional financial sectors. This transition reflects his belief that true expertise comes from staying on the bleeding edge of knowledge while maintaining a holistic view of systems, whether in finance, technology, or global markets. By integrating deep historical study with forward-looking innovation, professionals can navigate inefficiencies and structural barriers to create more equitable outcomes for capital allocation and societal progress.
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We do live in a world where information is really cut up, but we also live in a world where you can have access to more information than you ever could. [music] >> What are the key mental models that you keep coming back to that sort of explain how the world works to you? >> I'm a big believer in systems thinking. There's a there's a book called Thinking in Systems that I read. >> What does that mean to think in systems? >> I'm on the board of the Santa Fe Institute. The Santa Fe Institute studies complexity theory. I would describe complex systems as multivariable nonlinear systems. And multivariable nonlinear systems are very hard to predict. They can behave one way for a long time and then one variable can switch and they can behave another way. The weather, stock markets, all these things. There's consequences that can be first, second, third derivative. And you know, you you can't just think with a linear model or just think one variable because things can can go way off the path. Being aware that if you make a change here, it could change something here which could change something there and it has to be the whole system. >> How does that help you when you're solving problems or thinking about stuff? >> I think it keeps you out of trouble because you can avoid consequences that you might find out later. You know, I was I was talking to a guy that worked at one of the large dating sites. They had this this idea making the profile longer would lead to more engagement. Simple, you know, heruristic. And they tested it and it was true. And so they rolled it out. They found out many many months later that it let it it was negative for conversion like when people knew more at that level. >> Oh, interesting. >> And so but but you find that out way later. There's my point about like a second derivative effect. And so you just got to you got to be really conscious of the consequence and not get too deterministic about a single metric or a single variable and know what's important and what's on top. >> What was the process you took to go about learning the craft of investing and who were the mentors and peers that played a role in that? So because I started on Wall Street, you know, and not in venture directly, I got caught up in all the people you would expect, you know, around Wall Street and stocks. And so, you know, that starts with Peter Lynch, One Up on Wall Street, you know, best-selling book, probably the first book I read about investing, a random walk down Wall Street, Burton Male, all the Buffett letters, you know, uh, Ben Graham. Once you read Buffett, you have to read Ben Graham. And so, and then Howard Marx, uh, who's just incredible. And you were talking about the purpose of your podcast. those those people have spent their whole career assembling their thoughts and publishing them, you know, along the way. So, so that those were the ones that I read everything. I I think I had a very strong kind of bedrock of financial understanding. It's >> it's interesting because as you're saying that, I'm thinking like value investing and then you went into nonvalue investing in a way, right? Like how did that translate? How did what Buffett said translate into seed investing and sort of venture investing? >> I think having a firm understanding of the bedrock is super valuable and then when you recognize the need to innovate on top of it, it's just really good to have that foundation. I have an incredible peer in this guy, Mike Moeson. I don't know if you've heard of him, but he's a writer of financial books. We started at First Boston. He had probably been there a year year or two ahead of me. So it it you know just super fortunate that I landed in the same place as him and we've been lifelong friends since then. He introduced me to a gentleman named Bill Miller who ran leg mason and had this like 15-year run of beating the S&P one of the most famous investors of all time. And he claimed to be a value investor and he was the largest shareholder of Amazon for a very long period of time. And what he would say, I'm getting back to your question. He would say that, you know, value just means that the asset is underpriced relative to what you think it will be worth in the future. I spent a lot of time talking with Bill about network effects. And if you believe in that, then Amazon might be able to grow at a unreasonable growth rate for a very long period of time, which he believed. And so that that's how you get there. But yeah, I I I've often thought that many of the VCs in Silicon Valley would benefit from having a better understanding of finance. And one other answer to your question about how it becomes valuable. You know, I've always thought of Wall Street as the buyer of the product that venture capitalists create >> because of the eventual liquidity is either an M&A or an IPO. And now the price is being set by that group and that institution. So if I know what they value, even if we're starting at a very early place, two people in a PowerPoint, you're still thinking about when this thing grows up, is it going to be something they're excited about? >> Yeah. The trajectory matters more than the starting place, I think. >> Yeah. That that's where you're going to end. That's the out that's the output at the end of the day. >> What does it mean to know the bedrock of the industry? We live in a world where people skim. They want the gist of things. They want, "Give me the summary. Give me the executive summary." >> I'm going to tell you a story. So, um, my partner at Benchmark, Alex Balcansky, would go to this charity auction that I think Andre Agassi would run in in Vegas. And one year, he bought a dinner with John Lacier, the creative genius behind Pixar. Mhm. >> And we go to John's house and he serves us in his [clears throat] movie studio. He serves us in his viewing room a 10 course meal. And each piece of the meal is tied to a classic cartoon that he believed was was super important to understanding animation. And he would show it and he would talk through it and explain it. And you see that and you're like, "Holy crap." like he knows more about the history, you know, and and then here's another data point that I just love. There's a, you know, world chess tournament and they take a break and run a trivia contest and [snorts] Magnus Carlson wins the trivia contest and it's all about the history of chess. We do live in a world where information is really cut up, but we also live in a world where you can have access to more information than you ever could. And that's even more true now with LLMs. I mean, you could just sit there. You have an hour drive and you could sit there and talk to OpenAI and learn about anything you want to. And I think more people would benefit by studying the history of whatever field they're in. The there's another one that we mentioned is uh Picasso was a wildly successful realist painter by the time he was 14. If you go to the Barcelona Museum, you can see that. And I don't think anyone that looks at his cubis paintings would in intuitit that that was true. And then one last thing I would just say about this, and I think this is broadly applicable to almost anyone in any career. Imagine, let's just pick a field. I'm going to pick marketing. All right? Imagine you're interviewing for a job at PNG or Pepsi out of college and there's 20 people there and you're the one that understands the masters of marketing more than the others and you're able to bring that up in the interview. Isn't that wildly differentiating? >> Yeah, totally. I can't I can't imagine how it would land on me if I that I met that person and and yet other than fields like I think in like literature you probably everyone studies the greats but in these other fields it's not a practice and I I just think it would be like remarkably differentiating for people to walk around with the history of their field. I had a friend who actually recommended to people that their college essays do that when their admissions essays talk about like if they want to go into physics talk about the forefathers of like physics and and show them and like you'll instantly create tons of contrast with everybody else >> and you'll show a passion like it it it infers passion >> to want to know that. Um, and then the other part I get into, if that sounds tedious, it's probably not the right [laughter] like like if it's tedious to learn that this isn't a passion like you're not in the right I don't think you're in the right lane. >> So you've spent your life working with outliers, all these founders. Are there is that a common trait? And I mean not just the the history of the field but the details as well. >> I don't know if the history is a common trait. I would say that that a more common trait that's related in the entrepreneurial world is obsessive learning like constant learning because the disruptions that allow for the technology waves that allow for companies to be disruptive and take market share from an incumbent are all tied to something dynamic that's happening on the edge. And every entrepreneur that's exploiting that, it's AI right now. They're they're going home at night and reading everything they possibly can cuz the edge is moving and they need to be right there and they need to be a top 1 percentile person that understands this new thing that's happening. >> And today it's AI, but that was true of the mobile wave. Like like when the mobile phone came out, there were no engineers that had written apps for mobile phones. and a few people got on that edge and figured out what that meant. And that requires obsessive learning on the edge. >> The way that I'm thinking about that, and maybe I'm coming at this wrong, is, you know, if I'm young and upcoming, I'm on that edge. And I'm going to dive into it, but if I'm an incumbent, it's much harder to dive into that because it might mean, it's the innovator's dilemma in a way, but it might mean giving up a previous decision I've made or saying that I've been wrong and going backwards. How do you think about that in terms of competition? >> I mean, I think that anybody in any field should want to be on like curious about the bleeding edge and what happens. And, you know, as a venture capitalist, you know, we're always definitely afraid that some new app's going to pop in the app store that we haven't seen or and so everything that comes up, I play with, I roll around. Right now, I have like five premium AI accounts cuz I just don't want to miss something. and you get trained that way. I think everyone should operate that way. I mean, it's kind of an interesting contrast. I'm suggesting you should understand the really old stuff, the history, because it's differentiating and shows a passion and it gives you a great frame of mind, but you also want to really understand the new edge. If you do both of those things, like you're I think you're a power player in your field, you know. And the the second one is a great way for young people. That's another thing that could really differentiate you in an interview. If you're applying for that marketing job and you understand all the legends and the history, but you also really get Tik Tok, like that's super like that's going to be a very differentiated skill going into those companies and it matters. Like it really matters. Gives you a chance to shine. If I was to observe you use AI for a week, what would surprise me about the ways that you're using it? >> You often underestimate how much it can do. So you might ask it um to f identify the top 10 of something and then you're going to take those 10 and go study them. But you can say identify the top 10, list their pros and cons, and then rank order them based on this dimension. and then rank order them again based on another like stuff you would have done later you can just build into the prompt and it can it can do more of the work earlier for you early on I would often ask it for numbers and then I would go add them up and I'm like oh you can just tell it to do that part too >> do you find chat GBT is the best one >> I I like the project structure and I'm being sucked into the memory element in that it knows who I am and it knows things about me for for restaurants and stuff I' I've been using Gemini just because it has all the Google review data and you can, you know, you you don't just ask it which restaurants are good. You can say what are three plates people rave about and what have people warn against. Like you can go deep into the menu, which I I do all the time. You know, the coding people swear by uh Claude. >> Yeah. And I met a guy this morning who says for finance he prefers perplexity, but if he's doing deep research on companies or like companies and countries he doesn't know, he find Claude does better. So I think it's still a mix. >> Do you think we're going to end up with like one model that just sort of like dominates or do you think we're going to end up with niche models and they're effectively going to be commodities in some way? >> I think it's highly dependent on how things play out. There are certain examples in the verticals especially in the coding one which is probably the largest vertical right now where people have swapped out models you know cursor even lets the the user pick the model that they're using and as we move towards optimization and price optimization which isn't really the objective function right now but it will be in a few years um you may see more people try and do those swaps. I think the thing you know that could cut against that if [clears throat] the regulation gets extremely difficult and mundane and expensive that could actually lead to more igopoly and I think some of the players know that and are begging for regulation. [clears throat and laughter] >> Oh cuz they want that because it's a protective mode >> pulls up the bar against especially against the Chinese open source models. >> How do you think about regulation in the global sense? Just zooming out a little bit here. If if one country is regulated on AI and it slows them down effectively and another country is not regulated on AI and it speeds them up like how do you think >> this has come up especially around copyright you know and if if if if our models all have to adhere to some special rule and there's already been settlements and whatnot and the Chinese open source models don't it it could have it could have an effect you know it's very un I'm very uncertain how the EU might rule in that type of situation. So, I don't know. You know what I'm saying? I don't know how they might view it. >> How do you think about it from a systems point of view? Just from like China seems they have four open source models now that are really good. Is that >> By the way, this is a great a great question just to talk more about systems thinking. So um they have like 10 open- source models and so you have a situation where the competitive dynamic in China is more intense because it's more intense. Everyone's chosen to go open source and that creates a system that in my mind is capable of innovating far faster than the competitive system we have here. All the models learn from one another. You can actually have a model train another model or test another model. I'll use a simple metaphor but imagine you have two societies and both agricultural societies and one of them when all the farmers come to market they just sell each other goods and then they go back and the other society when the farmers come to market they're forced to share best practices with all the other farmers. Which which one of those is going to going to evolve faster? And open source allows me to see what they're doing, how they're doing it. Are they open sourcing weights too or just the >> Yes. And a lot of them are publishing how they figured it out like new techniques and and things like that. So it's more it's way more dynamic. >> And does that help Western nations then too? >> Well, there's an irony that a lot of the startups are forking those models and this would be a question of how regulation plays out and whether you know someone tries to stomp those out or not. I would say it's kind of a quiet secret just because I haven't read it on the front page of of the journal that you know especially from a breath standpoint like a volume companies are using these models all over Silicon Valley. >> The sponsor of this show is Coin Shares. While most of the industry was still arguing about whether digital assets were legitimate, Coin Shares was quietly building the infrastructure to invest in them properly. They now manage over 6 billion in assets and have stayed profitable through every market cycle. Fully regulated with the kind of transparency and governance that serious investors actually expect. 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Once you try it on a first meeting, it's hard to go without. Head to granola.ai/shane. And get 3 months free with the code shane. That's granola.ai/shane. If AI is really going to change everything or, you know, have such a big impact, how does it change how you invest? and you look at a company, are you looking like this is a rapper on AI? You're effectively like a calculator app on the iPhone or like how do you think about >> I I I think that question is up for grabs and it's a hot discussion between everyone. So, you know, if if you believe that these models [clears throat] become near sentient, then that there will be no need for a vertical model because this one model will just do everything. I probably come down on the other side of that. I think that there are workflows and data modes that if you get and and also just understanding like there's three or four legal startups in the AI space, they're just spending so much more time making sure they ingest all the case law and and really understand, you know, the processes and principles there and and then you implement with them and they're writing stuff on your behalf and you're building new databases out of there. I just don't know that you then switch that to chat GBT as they climb up the stack. But and I'll take I'll flip back to the other side. You know, they have talked about in their product groups, you know, going after verticals. So, it's I think it's a TBD. People point to Microsoft, you know, starting with the OS and then, you know, there were there was Lotus one 123 and there was I forget I can't even Oh, there was a word perfect like I can't remember the the specific apps, but you know, they eventually moved up the stack. That could happen. We're going to see how it goes. Do you think there's limitations to how we're training the models now, which is sort of they're trained on all the data from the internet, including like, you know, Elon has the opposite approach where he's like, we're going to take all the data and then we're going to filter out clear untruths. We're going to use that as the starting point versus the other. I do think that there is a valid argument that we might be running out of data, you know, that that we're I call it painting in the corners like you know, just we've filled in everything right now. One of the most powerful um solutions to improving the models is hiring experts. literally hiring experts for thousands of dollars an hour to to sit in and fine-tune and and you know ask very hard questions and then tune them to to be able to solve those. I there's got to be a limit to that like where's the edge of of human knowledge. So it's a big question like do do we run into asmtopes or not? And part of it goes back to do you believe these things can become [clears throat] super intelligent at which point they start solving things that we've never imagined. There's a lot of debate about that. >> I mean the I guess the theory correct me if I'm wrong is like the minute that they are super intelligent they can effectively make themselves a little bit better and at that point you just you enter a nonlinear curve. >> That that's an argument that some people have made. I I don't know that I believe it but but >> give me give me the other side of it >> rather than me stand on that hill like Yan you know Yan Lum you know makes that point like he says that that the next version of AI is not it's not LLM it's it's outside of LLMs it's broader than LLMs and that that we're going to run into a a asmtote with these because they're language based and there's just a limit to what language what you can capture with language which is part of why they're not specifically great with math and numbers, right? There are much better people to talk about this than me, but there's a people point to this famous game that Google Alph Go where Google implemented and the bot eventually came up with a move that was shocking to all humans and that I forget the number. It's like a famous move number, whatever. And that is proof that they can innovate, you know, beyond what they're taught. The people that take the other side say that's a very constrained game and environment. And the computers can search a field of possibilities that's impossible for a human to search because there's just too many, right? And that that gives it the ability to find that move that that we didn't know about before. But in the real world, it's not constrained enough where you can tell it to walk all the possible paths. There's an infinite number of paths in a complex in a big complex system. And by the way, those AI models aren't LLM based like AlphaGo is not LM based. It's a AI model trained to a very specific constraint system. >> And that was trained just by playing. Is that true? >> Yeah. Yeah. Yeah. Exactly. But and even FSD is you know at Tesla is a constrained environment like there's the inputs are the brake and the steering wheel and the gas pedal >> and or those are the outputs actually the inputs are are all the visual data >> it's scary good [laughter] I mean I was telling someone the other day I was like I would be comfortable sitting in the back seat at this point with full self-driving like I don't I don't feel a need to drive anymore. >> Yeah. >> What's your take on that? the corner cases. >> Would you sit in the back seat with your Tesla driving? >> The the the corner cases are impossible to fathom at this, you know, right now. Yeah, maybe at some point. I mean, I certainly think if it were in a world that didn't have the randomness of the real world. So, if you were in a g geographic area where all of the cars were that, it'd be easier to to to go into that mindset. >> Is that We got humans that think it's fun to test. People are jumping in front of these cars like that's that's that's not good. >> I was talking to Rory Sutherland. He's like, "You can just have fun with this. They're going to stop. You know they're going to stop." And so like you don't even have to look both ways now. What are the consequences of that? >> Yeah. Yeah. That's not good. >> What do you What opinions do you have today that are sort of non-conensus that you you think are correct? Having spent ton of time in China over the past 20 years, it's hard for me to adopt this mindset of vilification that's heavy amongst many in Washington and now many in Silicon Valley. The US is like 3, four, 5% of the global population. >> Yeah. >> American exceptionalism. When people utter that word, I always wonder like imagine the other 95% of the planet thinks when they hear someone say that. You know, that's probably a non-consensus viewpoint. >> Are there Do you think we're overfunding this buildout? How do you think about that? >> I saw that smile on your face. >> I mean, it's such a hard question to know. If you told me five years ago that the that these uh max seven would become worth $3 trillion and then turn around and take their free cash flow from 50 to 100 billion a year down near zero because they were going to spend it all on capex, I'd have been like no way. Like I wouldn't have believed it. So from a certain standpoint, I'm shocked that the money's this big. I will tell you that the venture capital community, you know, I meant we talked earlier about increasing returns and and that concept and other people call it power laws like when startups have become important in an ecosystem and then they've been able to prove that they can grow and that that growth might be a function of their size already or their footprint or their users and that would include everyone from Google to Amazon to Meta that they end up being worth way more than anyone thought. And I think the investor community writ large has slowly become aware of and believes it strongly in increasing returns and power laws. And so over time, if they all believe that, they're going to be more willing to invest on the come and take risk. Right? That that makes sense that follows. And so, you know, someone forwarded me a chart this morning of the losses of the leading company in the field prior to going cash flow positive. And you look at, you know, what for for for Amazon it was like two or three billion. For Uber it was like, you know, 15 billion. And now for these companies, it's going to be way bigger than that. And so the venture capital community as a whole is is getting more risk-seeking and taking on more risk because of their knowledge of how things have played out in the past. >> What do you think are assuming we are overfunding? We haven't had a correction like >> not not really >> like a mini one kind of like and usually that that weeds out sort of the weak competitors the strong ones survive and >> it depends. Yes, but but it can be, you know, if you look at what happened with the.com crash, you know, there was a four year, three or four year lull before the Amazon of the world started climbing out again, you know, it was it was like a nuclear winter like right now there's so much optimism and belief in AI. you get to the place where there's very little, you know, um I don't know, some of these the these quote circular deals that people are talking about >> [snorts] >> um enhance the probability that we'll have a correction, but also extend the time before we have one. >> Wait, how so? >> Yesterday at the dealbook conference, Daario was asked about circular deals and he goes, "Well, maybe people just don't understand. Let me explain how this works." Um, you know, imagine you're a cloud service I'm I'm echoing what he said. Imagine you're a cloud service provider and you notice that this company Anthropic wants to develop this model. It's going to cost maybe $5 billion, but they don't have that money. So, you give them that money so that they can spend it. And I'm like, well, if you didn't give it to them, they wouldn't spend it. And so like the growth of everything is enhanced by the fact that you're giving money to companies to spend back on your services they wouldn't have otherwise. And so if you were in a more constrained environment where you didn't do that, things wouldn't be growing as fast. You inflate you inflate what's happening. >> So you push further ahead faster. >> Yes. >> But there still is likely to be sort of a culling of the the weaker competitors. Look, first of all, if a company's successful, someone will knock on your door and try and give you more money. So, like almost every round is preemptive for successful companies. And when you take that much money, $300 million, the only way to spend it is to take your burn rate up. And I always thought of burn rate as a measure of risk. 10 years ago, like it was super risky to burn a million a month. You know, today these companies are burning five billion a year. Like like you know, you're you're burning a hundred million a month or more. Like it's really hard and this may go back to financial bedrock and whatnot. It's really hard to know what your unit economics are >> when you're being that aggressive financially. >> Do you think things will change? Like I I wonder about the role of retail investors in this like if you tokenize some of these assets like they might be competing with VCs in some way to fund some of these startups. How how do you think about all of that playing out? >> Well, first of all, there is zero lack of fund availability right now. So >> that's not the bottleneck. >> Yeah, there's [laughter] >> the pricing would change, right? There's no con. >> This is kind of played out in the public markets. I mean, I think you look at obviously like stocks like GameStop, but I I think most people believe Palunteer is a stock that retail investors really love and take it to a valuation that it's very hard for institutional investors to get their head around. So, some of some of that has played out. Yeah, it's it's there's a there's a risk with tokenization, especially if it happens on assets that don't have regulation around financial disclosure that you get a ton of speculation and even worse manipulation. >> Do you think that that would affect private companies if there was like if somebody figured out a way legally to tokenize Stripe, for example, and the price of the the Stripe share that's tokenized effectively fluctuates wildly? Yeah. Do you think that has an impact on Stripe or its employees? >> Well, it would. One of the reasons they're staying private is so you don't have that dynamic >> because they have more control over sort of like the market cap pricing >> when they do um liquidity events for their employees. They sit down with a handful of investors they trust and they negotiate a price and so it's done on a one-off basis. And I think we're going back to the financial bedrock. The underlying asset probably does move around a lot. It's just it never it never gets recorded so you don't see it. >> Right. >> And that's a I think from the operator standpoint that's a benefit. Like if you've heard any public company CEO, if their stock moves around a lot, it creates a lot of chaos for the employees who are owners who are wondering what it means. This is already starting to play out, right? Robin Hood announced they were going to do what you just said and and the companies, you know, threw up a a a strong argument that that would be illegal, like you don't have a right to do that. So, we'll see how that plays out. >> Yeah, it's fascinating how all that plays out. Or you tokenize real estate and what effect that would have on. >> Look, I I I think that and I've been outspoken on this particularly around the IPO process. I think it is insanely unfair to the companies the way they're forced to go through this process where the bankers pick the price and pick the shareholders. There's just no need to do that. If you took a freshman computer science student and a freshman finance student and said, you know, imagine how a company should go public. They would match supply and demand anonymously like you would in any auction. And exactly the way a a ICO works. Yeah. With tokenization, no one would invent this thing where you you cherrypick your best customers and give them this sweetheart price. No one would do that. So, I do think that Wall Street because they just can't get out of their they can't let go of this greedy power grab they have around the IPO. you know, we we pushed direct listings for a while, which which uses this auction mechanism, and they could have embraced that, but they didn't. They've gone back to this kind of controlled igopoly. I I think that is an area where where tokenization like just merely getting to the first base of how the share should be allocated um could be very disruptive. Stable coins could be very disruptive too to credit cards. >> Well, go deeper on that. most of the rest of the developed world, the governments um established a an ability to do instant transfer from bank account to bank account and from bank account to a partner or retailer, whatever. UK faster payments did this 20 years ago. Recently, Argentina did it with picks in the past six years and it quickly became 60 70% of transactions and precisely because of regulatory capture the banks have kept our government from doing that. They've the government wanted to they have something called Fed now but there's massive push back in the finance committee in Washington so it never happens and as a result you know we have credit cards that charge two two and a half% in a whole ecosystem of companies that live underneath that umbrella. If you have a Coinbase account you can put your money in a USDC stable coin and earn 4% and within seconds immediately transfer money to someone else for pennies. What is a stable coin? Like I'm totally naive here. >> It's a cryptocurrency that if the company's following the regulation, I believe that USDC is is in fact doing that. Um where they have they have created a dollar fordoll holding in treasuries, US treasuries. Okay. For each each stable coin that's represented. >> So that's kind of like the gold standard back to the dollar almost. >> Yes. But because it's on the crypto rails which are now quite proven and quite fast and global and immediate, it gives you the ability for me to to give you or for a company to give a company or anyone um a dollar, you know, immediately. Who holds the dollars in this case? It's like if a bank transfers a dollar to another bank, I I just in my head I'm like, you know, it's it's an electronic transfer, but in reality, it's probably like there's a dollar actually transferring at some point. >> Well, no one's taking a physical cash dollar, right? Like that's all it's all digital anyway, right? In America, if I want to send you 50 bucks digitally, I've got to go through AC, which is three-day settlement, which is part of this regulatory capture in in in Argentina now it's immediate because of pics but >> so we don't actually need the three days we do like the regulatory makes that happen >> no I can I can wire to you same day but it cost me $25 and I have to fill out a page of forms and I might have to do a verbal commit with my bank >> so the way around that is stable coins because you're really just working around the regulation >> same yes and credit cards which cost 2 and a half% but this there's no reason that it should and once again >> these other countries which include UK, Australia, India, China, Argentina, they've all done this but we never did it and probably won't like I at this point I think stable coins will get there faster than than the government will will be able to do it. >> Video is the most effective way to communicate, but it's always been too slow and expensive to produce. 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That's drinklmnt.com/tkp. >> How do you think about the competitive mode of Visa and Mastercard? I think they will be heavily threatened by this. And historically what they've done in and by the way those two companies have two of the highest operating margins in [snorts] the history of business. They have like 60% operating margins and they're they're duopies and and they were created by the banks. So and the banks have a stake in it. So it's like the the whole industry is is kind of stuck in this world where they make a lot of money because it is this way. But there's zero reason why it should cost 2 or 3%. Just zero. And it will change in China because they had this digital immediate transfer. Um Alibaba and Tencent were able to very quickly build digital wallets that people carry around. And so if you walk around China, if you want to buy a hat from a street vendor or or a car, you know, in a Huawei store, you you use we we we chat pay and Alip pay for everything. You scan a QR code like at a you check out of a restaurant like you can just pay at your table. There's a QR code on the table. You just take your WeChat pay or Alip Pay and scan it and you're done. like one click. I so they they've innovated their entire payment system way further than we have because because of this the decision by the government to make money transfer easy >> and that means like no three-day settlement sort of >> exactly >> and it doesn't necessarily mean stable coin it just means >> that's true I just think because they waited so long in the US you know this Fed now project's been just out there forever that that the threat becomes this new thing and especially with the momentum the crypto momentum in Washington that could change with a new administration. >> As you were talking about that I was also thinking about Moody's and AI and I was like oh Moody's you know basically they sold analysis on debt. >> Yeah. How do you think AI changes their competitive position? Because like in theory AI would be able to do that better than or equal to Moody's which also makes great margins. >> Yeah. I think Moody's power comes from the fact that um that it's a standard and everybody trusted as a standard, >> right? So even if they used AI on the back end, they're still the >> the Yeah. the the the watermark. Someone could pop up. I mean, there's been a lot of talk about these companies like ISS that that that tell shareholders how to vote. That came up yesterday um at at the Debook Conference and whether or not AI could solve that problem as well. It's possible. Yeah. I mean, I think everything's up for grabs. >> What do you think about independent sort of like services like that that that profer advice on how to vote your shares? Oh, I think in the US it's gotten to a really bad place because of the rise of the index funds. Um, the index funds and this is why they're asking Larry Frink about it at Black Rockck like they don't the index funds don't have the time to truly evaluate the what the vote should be in these situations. And so the they rely on these services, but these services have been built. They play this game that that that it's not particularly um settling, but they they score you, but they score you with a black box. They don't tell you how they score you, right? >> You and guess how you can learn more? >> You you hire them. >> Yes. >> So they get paid on both sides. And it's just it's more of a heist, I think, than anything else. And I'm I've I've spent some time talking to I don't know that they they they they got focused on issues that weren't shareholders interest like what what's like what they really care about is is um what what's best for shareholders, >> right? >> And they got away from that. Um the the Tesla case is a great example that that package that type of package that they did for Elon. I've said this, you know, publicly. I would agree to that type of package for every company I've ever worked with, and most CEOs wouldn't take it. Uh, it basically says you don't make money unless the stock goes way up. And if you stock goes way up, you make an obscene amount of money. And I would do that deal over and over and over and over again. None of these ISS like evaluators agree with that. like they just in fact they take the opposite. They say oh no that's a negative we should vote against it. >> Is it just because they're looking at the headline number and they're like that's egregious not looking at what's required to make that happen. >> Yeah. And they started from a place of corporate governance where they were looking out for fraud. And so so risk mitigation rather than shareholder interest. And so when you come at it from that perspective, you're like, there should be rules and people should adhere to the rules and when people get outside of the rules, that's bad. >> Yeah. >> I think that's their legacy. >> What do you think are sort of the second order effects of the rise of passive like we've uh indexing which is mostly post the GFC. How do you think it plays Well, this is one of those things like this this wouldn't be a problem were it not for because it's the large number of shares held by the uh the passive it one one thing that would be really great is if they just wouldn't vote um because then the people that are active shareholders would have more of a say in what happens with these companies but there's they own such a large percentage. Um >> there's also an argument that they should have to vote in the same proportion that direct holders vote. Yeah. Well, if they didn't vote, that would happen just by natural because the the vote would just be it'd be more like how unfortunately how voting works in America where you only have like a 20% turnout. But >> the second order factor that like I could have control of the company with a very small share of >> Yeah. At first, I think the public investors got really scared because they were marked to the index and they ended up doing what people call closet indexing to make sure that they didn't >> um lose out. And like when the MAG 7 took off, um if you didn't own those, like you had a bad year, as an example, and so you're forced to kind of closet index. But they were they had kind of reached a point where they think the number of active investors is so few that the ability to get an edge has maybe increased as a result of the of the massive indexing. >> Do you believe that? >> I don't know. I mean it's it's the buy side is a very hard job like to to beat the S&P. Some people have even highlighted the fact that, you know, QQQ has probably outperformed 80 or 90% of venture funds. >> One of the surprising things that I learned about you through reading your book was that you love the craft of storytelling and writing. >> Yeah. >> Talk to me about what you've learned about storytelling over the years and because that's really important to founders. It's really important to anybody trying to get a message out in today's world. Someone asked me like the top three traits of founders that are successful and I put storytelling in there. Um the the there's another thing that happened you know when I prior to going to business school I didn't read much but some bit flipped when I was in business school. I started reading and I I started with business books that most people know. Um, I got into personal development books, which I find a lot of successful people have this moment in their life where they roll through, you know, Dale Carnegie and like like Seven Habits and stuff like that. Um, and then and then biographies. >> Um, but but after that, I I I've kind of fell in love with with long form non-fiction journalism that reads in an exciting way. And part of it was the wave that was Malcolm Gladwell and Michael Lewis and John Crockower and those books that read like fiction, you know, even though they're non-fiction. And there's actually multiple books written on that art. It's called the new journalism and the new new journalism. And I've read those books about that writing. And I just find it super powerful that someone can maybe put together 20 pages that like really impacts you in a certain way. And so I started studying the craft, studying Buffett and Howard Marx and seeing these investors that were successful like putting their stuff out there. If I was thinking through a problem about a new most of my most successful investments fall in this category people call marketplaces and before there was a first marketplace like there wasn't a knowledge base and you know we crafted that along the way and codified it and wrote it down and that in addition to helping you think through all the corner cases and this is exactly why Bezos has his six-page letter concept at Amazon. He he believes that if you have to write it out and make it stand alone and be cogent that you'll think through more of the the problems and you'll it'll be more cohesive and it'll it'll um you you'll figure out the loose ends and you'll tie them up. Um, and but in addition to that, in the venture world, for the founder that doesn't know you, when they see your knowledge on a subject or they see what you're talking about in their own business, they reach out to you. So, it becomes a calling card. >> It's like a magnet. >> Yes. Yeah. And I I'm not the only one that's done it. A lot of people have done. And some people don't use that technique. There's other ways to to get deal flow, but it's powerful if if you do it right. >> You mentioned storytelling. What are the other uh you know chosen unfair advantages that founders have? You said there was three. >> Oh, right. I have a fourth one. I hope I can remember it. I think product instincts is another one that that that comes partially from understanding the new edge which we already talked about but like it probably took my whole career for me to fully understand how hard it is to hire someone who's not a product first individual and then get them to be good at it. I'm sure there there are examples, but it's got to be 5% or less of the use case. super hard. >> Um um so uh storytelling is so important because in the founder case, you're recruiting employees, you're you're you're recruiting executives, you're raising money, you're closing customers, you're closing partnerships, you're selling all the damn time. Yeah. >> And the best ones are just super effective at it. Um and you can see it with Bezos. You can see it with like Toby at Shopify. I mean, God, like, listen to any Toby podcast you possibly can. Like, of course, the world's going to follow this guy, Daniel E. Like, they're just so gifted at describing what they're trying to do, you know, and that's that's just just, you know, super super valuable. I once asked Jeff Bezos, "How have you had such a successful angel portfolio? You don't have any free time." And he says, "Oh, when I meet an entrepreneur, there's only one thing I ask myself. Is this person gonna do this no matter what? Come hell or high water, they're doing this. Like, they're just already convinced that this is so important, they're not going to stop. And I think that level of determination is present in all the great founders. Like, they're just going at it, you know, full blast. What are the what are some of the real world lessons you learned while working with Uber that you wouldn't find in like an HBS case study? >> Well, that that's that's an easy answer to get to quickly. Although now uh [snorts] because I had I had a moment in my brain where where that exact phrase you just said popped into my brain. We were, you know, in a situation where I think most people that were investing in the category knew it had winner take all dynamics and network effects. And as a result, there was this determination that they were just going to have to fund it kind of ad nauseium. And you had a situation where the burn rates, you know, where okay, well, someone's hands lift a billion dollars. Well, then we get handed three billion. And so, and and and once again, the only way to compete in that world is to spend that money. And so, you have these burn rates that are bigger than any pro public company would ever spend going after a new category. And and so aggressive. And I thought to myself, at the moment, um there is no HBA case study. You could take the board members from Walmart and Costco and GM and and General Electric or whatever you consider the top 10 best companies and they would have never been in this situation before. So there was no there was no one to call. There was no there's no mentor to go find. Um which was uh horroring a bit to recognize you're in that situation. But now all the AI companies are in that situation. So, I uh I feel for him. >> Uber was kind of the first in the in the >> in the mega burn. Yeah. I mean, well, Amazon was, you know, they they had a big burn rate, but then Uber took it to a new level. Um, but now it's at a they've added a zero. [laughter] >> I'm curious from the like how Benchmark was structured on the inside and how that structure contributed to its success. >> I've talked about this a lot. I I was very fortunate to get invited into Benchmark. I was I I joined on the third fund so I wasn't there early. Um they had left the founders of Benchmark had been at hierarchical firms where they felt like the senior patriarchs were maybe taking too much of the money and too much of the credit and not doing the work that was imperative for the firm's success. Um most partnerships, you know, you think law partnerships or accounting firm partnerships work in a way where the the senior people have more power and take more of the economics and the junior people have to work their way up over a long period of time. The founders decided at Benchmark that they were just going to make it equal, an equal partnership. And there's no there's no lead partner, there's no king, there's no president, there's just five equal partners. >> So what are the second and third order consequences? >> There's a bunch of them and I think most of them are positive. The first thing is it makes it very easy to recruit exceptional talent from other firms because they're not in that situation and you immediately and I was at a firm that was hierarchical and you know even if you went back and said well I'm going to leave to go to this equal partnership and they said oh we'll make you equal well you did it because I was leaving not because it works that way >> right >> that's one the second one is it really encourages development of the new people that come in because I'm going to take an equal part of their success when they start delivering. And so I'm not I want them to be super successful and I'm going to spend time and and I boy on my way in I felt that like I just felt like you know and the type of support it if you're in a up or out firm I bet it feels kind of lonely. I bet you know you're competing against that person over there. Are you going to share ideas with them? Maybe, maybe not. Like, and in this equal partnership, you know, if one of my companies needs a new CFO and they know of one, they'll probably just give it to me right away. My company succeeding is no different than their company succeeding. So, you just create a a different dynamic. And you don't spend any time annually on comp review and recutting the pie. You don't like it's all it's always equal. it's always going to be equal like that that amount of political overhead just goes away. It there is there's one huge negative. So I don't want to just say it's all um the it's almost impossible to have uh because you don't have a CEO. It's hard to scale out and it's hard to have new initiatives like because there's no like oh maybe we should you know the website was always a funny one like who's going to own the website? Well, are we going to hire, you know, someone to do that? And well, who owns that responsibility? >> Yeah. >> And when Matt Kohler came in, he had he's like, "Oh, man. I'll take it on. I love I know exactly what we need." He created this super complicated website and it had all the founders on it and now they're connected to all the partners and and people started complaining because stuff wasn't right. And one day, Mac came in [laughter] and uh he said, "You know what? I'm taking it all down and I'm putting up a splash page. And he did that. He did that like I don't know 15 years ago. And still today, Benchmark has a single page. And that's a result of this issue that I'm describing. >> Well, you know, it's interesting you say that because I find a lot of websites have such a high cognitive load to use a splash page with like, you know, four or five sentences or Berway's website. I totally get it. I don't there's not a lot of cognitive like [laughter] if I you know I heard this example um from a guy a couple weeks ago. He's like if I'm going to buy a sweater I don't want to know your mission statement. I don't want [laughter] like I just want to buy a sweater. >> There's a little bit of bespoke confidence in in just having a splash page. I would just add that there are plenty of highly successful venture firms that aren't structured that way. And so I don't it's not I'm not saying it's the only way to do it. It's clearly there clearly many ways to do it >> in a world of wash with capital. What makes a founder choose Benchmark or somebody else? Like what goes into that? >> First of all, at a high level, if you're successful as a venture capitalist, people want to work with you. you know, when I came in, you know, the Mike Moritz, you know, John Door, like they've had so much success that that not only, you know, is it likely that they >> are are great at what they do and know people that will help your company succeed, but their stamp of approval of you will carry weight in and of itself. And so there some people have said it's the only investing category where there are network effects because once you have a reputation it it you have an unfair advantage in deal flow. Underneath that I would I would say founders are particularly um motivated to be around people who understand what they're doing u and are excited by it and excited about it. And one of the reasons young people can break into venture and be wildly successful is they're much more likely to be the age of the founder, they're much more likely to feel someone that understands what they're doing with with many of these technologies that are new. They're much more likely to understand them. And you know, I I've used examples describing this in the past, but let's say you're a really into esports or something. You you it would be very easy to know more than the successful generalist venture capitalist in that category. >> Yeah. >> Like you could very quickly know more. And that could be true of of YouTube video creations. Like it'd be very easy for a young venture capitalist to know more about what it takes to be successful on YouTube than John Door or Mike Moritz or me or whoever. Like because you could just go spend 100% of your time on that. So, so in that way, is it sort of like athletics where you you age out in a way and you're competing against younger people who know or understand a niche better or how >> I I I think the the whole industry bends towards youth for that reason and because it's a hustle business like there there's there's always a rock you haven't looked under and you know age brings children and homes and and and other requirements you get tied to and responsibilities and you're just not able to go spend 80 hours a week studying YouTube like you just can't. >> Um so I think it bends towards youth. Um which is great like like it's a it's a highly competitive industry. It's hard to get a job but if you get one there are reasons why you can break in. >> We always end with the same question Bill which is what is success for you? >> I think I think it's changed over time. I would say when I look back on my venture capital career, I made a decision, a very specific decision to say, "Okay, I'm done." And and I I don't think I would have done that if I felt there was work left to do. I think I reached a point where I felt there wasn't any work left to do. So, in that case, you know, that was my dream job. I was thrilled to do it. I loved every minute of it. I often said that I would if we lived in a socialist society and I everyone had to work for free, I would still take that job. Um or the same fe salary or whatever. Um >> might not be eating, but you'd be >> Yeah. But that's now done. And so as I look forward, you know, I was very moved by this book Arthur Books wrote called Strength to Strength to Strength where he talks about this next chapter in your life. I would like to take some of the techniques that I use to be successful as a venture capitalist mostly around the blog and understanding problems and synthesizing and see if I can apply those techniques to bigger broader problems in society and see if I can dent the universe a little bit that way. >> I love it. I wish you luck. >> Yeah, me too. Me too. >> Thank you so much for taking the time. Thanks for doing this. It's great.