What began as a PowerPoint presentation Bill gave to an MBA class at the University of Texas turned into a six-year journey writing this book. At the heart of it is a question that I think resonates with many people: How do you make career decisions you will not regret? Bill became especially interested in the idea of career regret. And that work eventually contributed to a study showing that six in 10 people would have chosen a different career path. The book is really about helping people move past fear and giving themselves permission to pursue what they are genuinely passionate about. It is built around seven principles including chasing curiosity, honing your craft, developing mentors, embracing your peers, going where the action is, and giving back. We are very lucky to have both Bill and Vince with us today. So, please join me in welcoming Bill Gurley and Vince Hanks to MIT.
Thanks for being here, Bill.
You know, I actually think most people are probably wondering why are the two of us here because neither of us went to MIT. But it turns out if you back enough founders that went to MIT, they'll invite you back.
I think, you know, I was interested in doing this with you obviously around your new book. I think so many people come to me asking like, 'Oh, if you're successful, how do you find that path?' And I think a lot of things in the book resonate. I want to talk about the book a little bit today, but also I'd rather talk about putting it in context of both your career and the industry. Very few people I think that are close to the modern AI world have also seen the internet and mobile. And so experience is a good thing. And so I think we should try to talk about that a little bit today. You also, you know, you took Amazon public, but now we have some of the biggest modern companies going public. And so what are some of the things that were similar about that and will be similar today but different too. And I also find you to be a lifelong learner. Every time I see you, you're always asking and learning about the new thing. And your book profiled so many people in a way that I thought was very different where it wasn't really about tech entrepreneurs, but it was a very wide breadth of people. And so really I want to start with there, which is what you probably read so many biographies and met so many people. What was kind of the most wild or mind-blowing story you came across that didn't make it into the book?
Well, so one thing I would start with by the way before I get into the book just as because we're going to transition to other things. This is an interesting opportunity as you guys listen to us talk because I spent 25 years in venture capital and have for most respects started retirement which means I don't do new investments anymore. And so I did see two and a half decades of venture. Vince really represents the new guard, Thrive is one of the more disruptive innovative firms out there in venture capital and so you're getting two perspectives but one that's super modern and one that's kind of dated so I wanted you to have that context. One I'd say the key point in the book, and by the way, I intentional, the book's divided into two halves, principles and profiles. So, it's stories of success and tools of success. I intentionally, me and my co-writer read like a hundred biographies, but we intentionally only put the ones in here that are in fields your parents would tell you not to go into. That was very intentional. So, I left out entrepreneurs or doctors or lawyers or consultants or investment bankers. There's none of those profiles. And because I wanted to push people to believe they could go chase careers way outside their field. And the common trait that exists in all of these people, and we also only included people that started at the very bottom rung, so no one born on third base, also an intentional decision, is this commitment to lifelong learning which you brought up. So they have this insatiable curiosity and what I've come to believe is you can't force that as an action as like a discipline activity. You can't say oh I'm going to go be a lifelong learner. You'll just run out of steam. And Angela Duckworth who famously wrote Grit, ten years after it came out, so Grit says that it's half passion half perseverance and she said later she should have overemphasized passion because this generation of kids partially because of this stupid gauntlet you have to go on to get into these amazing universities have been taught to grind. They've been taught to grind to persevere. But she now says perseverance without passion is suffering. And so you know one I think the key test of whether you're really, so the mechanism that unlocks lifelong continuous learning is obsessive fascination and so if there's a topic that you're so fascinated with that you would study it instead of watching your favorite streaming series on Netflix that's the kind of thing you're looking for and almost all the people in the book were able to find that thing that allowed that. For a profile I didn't put in there, there might not be that many sports fans in the room, but it would probably be Mike Leach, this famous coach that he was a lawyer in his academic world. And despite being saddled with debt from pursuing the lawyer thing, he took like an assistant coaching job that paid like ten grand a year just to get into football. And then worked. He didn't end up winning like national championships, but if he passed away unfortunately a couple years ago and at his the service they did in Starkville, several coaches came out and talked about the influence he had on the industry and his coaching tree is amazing. So, the number of people that worked under him, but he was so fascinated with innovating in the game that he just lived on the edge. And there's an AI thing to this as well, which is I think people that are high agency and fascinated, they not only study the history of their field and all that, but they're constantly studying the edge of their field, which is a much safer place to be. If you just arm yourself with the rote algorithms that they taught you in school, those are in the models. And so that's not like just being able to execute the rote part of the job is a not safe place.
What do you, when you're talking to folks, you know, you obviously lived a career of investing and meeting lots of people, how do you, what threads are you looking for as someone's telling you about their story to identify if this person has that potential or has found their kind of fascination early?
Well, I mean, are you getting into like betting on a founder kind of thing?
Yeah, kind of. Or just in general like we have a lot of aspiring investors, entrepreneurs, people in this room and like as they're listening for from other people who are curious about things or even think about themselves, what were things that you are looking for on people that they should maybe be thinking about in their own right?
One thing about this fascination concept is if you kind of know it when you see it. It's like really noticeable when someone is captured by something in this way and because of that all kind of good things happen to them. So if there was someone in your organization that was just emphatic about robots like and that's all they talked about. When a startup came by that had anything to do with robots, you'd say, 'Oh, go talk to Sally. That's all she talks about.' And so like introductions come your way, like information comes your way. Oh, you probably want to see this. You love robots. Like there's this energy. Yeah. That they put off. And by the way, that shows up in interviews. Like imagine if you're going to the career center and you sign up for a job interview and there's 15 of your peers in that same group and one of you loves the industry so much that they know all the history. They've read biographies of all the founders. They like pop when they talk about it and they smile. They're going to crush you. Yeah. They're going to get the job. Yeah. Like so I just think in fact, one thing I might worry about in an AI world is these high agency fascinated people might separate even more than they do already because they can. Saying the amount of information you can adjust to with AI means you could, the ceiling can be even higher and so the delta. Look how fast you can learn like you could never learn faster than right now. Yeah. And I think it's exponential like with AI because even before AI, podcast, YouTube, interviews like your ability to just go home and self-learn like go back 40 years and imagine what self-learning looked like. You get a library card. I mean like it was hard but today you can learn and so if you're high agency and are just ridiculously curious you can run really fast.
If you're, I mean from the investing side, you know, I think about this when we're meeting founders, how do you pull these threads out of them? Do you think it's actually true there where actually it's very obvious in the first 30 minutes of meeting somebody whether they have an extreme fascination?
I think most founders do like and most founders are obsessed with the new technology and the wave that's happening. Yeah. And so, you know, I mean, take Brett Taylor who has been around for 20 years and has done amazing things, but a new thing pops up and of course he jumps over in front of it and studies it. And now if you listen to a Brett Taylor podcast like on merging models to solve real corporate problems, he's what top five? Yeah. In the world. And it's kind of my point about high agency people being able to run fast. But I think most of the people that succeed in Silicon Valley, both from a founder and an investor standpoint, are hyper curious about the technology itself and where it can go. I would include you in that.
Thank you. How do you know or like you've seen a lot of great people too. There's also to me I kind of always wonder this like how do we tell if someone's in the top, you know, there's a big difference between the top 0.1%, top 5%, top 10% and so many of the businesses that we're in a lot of it's on the margin or like you're saying like identifying information on the edge of what's happening is where it's most comfortable to live because like I think about our job a lot of it is making decisions very much on the margin not the baseline or professional athletes it's true restaurants it's true. How do you distinguish between that like the difference between top 0.1% and top 5%. Or does it matter?
I think it matters a ton in venture capital because of the power law. There's just asymmetric returns in venture capital. So, you can lose one times your money, but if you miss out on Google as I did, that's 10,000x, right? I had Larry and Sergey presented at, I brought them in 25 employees. So once you recognize that asymmetric outcome, you and you guys live this, but you're just constantly looking to try and put yourself in front of those things. So, you're in that game where you're looking for that ultimate. One of the things that I would say about founders that are going to go do that, it requires a little more multi-dimensional, for them to be more multi-dimensional than you would than just being fascinated with one thing because you're going to have to learn to, no one ever talks about this. Everyone assumes a founder can evolve into being a CEO, but if your company goes from 10 employees to 100 to 1,000 to 10,000, you got to lead an organization. Yeah. And so there's a scenario where you might be fascinated with technology, but are you fascinated with leadership techniques, you know, maybe not.
What's your advice in that situation? I mean, we see that all the time where like great technologist, but as you become a company of 500, your job is not technology anymore.
I mean, I've watched people like Michael Dell go on that journey. He promoted himself to chairman, kicked himself out, went back in like and it's a requirement. You know, people are like, this gets into the multi-dimensionality thing. Bezos and Elon have leadership techniques that are innovative. You know, how did Bezos keep Amazon innovative after 100,000 employees? He's not in every meeting. Yeah, he's created some heuristic that allows the whole organization to behave and his fascination with it and that was a big thing that people talk about and he got interested in, he convinced himself let's just say to be interested in the leadership component and it's but it's not a fact that a founder is going to solve that problem. Yeah, it's hard.
One of the other things that you talk about in the book that I find interesting is just age. Like does age matter? Or I think about this a lot in the investing career just in general when you're coming out of school and people want to be successful young. But I often think about like being successful young is either a combination of luck or it's ego driven, right? Because who cares if you're 32 and successful or 45 and successful. You'd rather be fulfilled and happy going and doing it. But yet a lot of people say, at least the world I work in, venture, it's a young person's business.
Yeah. Well, Doug Leone is back at Sequoia, you know, and I think he's in his late 60s or something.
I still stand by my... Would you go back to Benchmark? No. But I do think it's a young person's game.
Why do you think that or like when I think about what advantage does a young person have in the industry?
Well, before we get there, let me hit one thing you said just about age. And if you read the book, you'll get this notion, there's a chapter called chase your curiosity like you may not be fascinated with something at the level I'm talking about and I would just say that's okay. I would just say recognize it and experiment a lot. I think Angela Duckworth now says wander with a purpose like just move towards the stuff you find exciting. There's this interesting thing that one of the Acquired podcast guys did which was at each one of his companies he created a side hustle and so he would go to the people he worked with and say do you mind if I do this on the side which is actually I think it also differentiated him as someone that took initiative and whatnot and so at Microsoft he created Microsoft Garage which was this thing that allowed Microsoft to start talking to startups again and through that he met venture capitalist and one of those hired him at Madrona and when he got to Madrona he said what if I start a podcast on the side they said sure and that got him into podcasting and now Acquired one of I think from a revenue standpoint top. And so there are ways to wander and experiment and try different things and talk to people like who knows like you might meet someone that does something you would love to do and here's another thing for young people: don't get overextended financially because your flexibility to repot is dependent upon being able to jump from one place having low opex. We my friend group we say low opex. Yeah. For young people this is a question I often get which is you know you're trying to compete in a... I can ask the venture young game if you did you want me to finish that part or not?
Well that's why I'm kind of going there. You could say in the context of venture because I think some people here might want to go into investing or investing broadly. I think it's true in business too. You know, experience versus naive or in investing, how do you compete against the people that have lots of references and founder relationships and so forth. You know, people do say venture is a young person's business. And so I just I would love for you to kind of pull on that thread of the why.
So there's about three or four reasons. One of them is it's insanely hustle oriented. And I don't care what you say if you end up with a big house and three or maybe two or three houses and three or four children and you know you join a bunch of nonprofit boards like your day just gets taken up and there's no amount of rocks you can look under and go to sleep at night without anxiety. Like you can't because once again because of this asymmetric outcome thing you live in fear of missing just one or two deals a year. There's like how could you possibly minimize the chance of not finding that like it's hard and so that makes it a hustle business and you know can you be out meeting entrepreneurs four nights a week you know it's hard if you totally as you get older. Yeah so that's one reason. Two, I think and this all goes back to the asymmetric outcome thing as you get older you build more mental models and you become more cynical and that could make it very easy to miss this next thing. And the next thing may break the rules of the previous thing like you and I have talked about things like do you invest in hardware or not like an old venture capitalist would say no never do and then you might miss Tesla or you miss SpaceX like and so that I think being idyllically naive could be a powerful tool, you know not stupid, no but optimistically naive could be very helpful and then you're more likely to be close to the age of the founder you're trying to get close to which can be beneficial.
That I would say we, you know, Thrive itself is a young firm, we're only 15 years old and I think one of the things that we lean into because often people come and say oh well if you are already getting access to the companies isn't that good enough and I'm sure this resonates from the Benchmark perspective, we're not competing against someone that's, you know, nobody, we're competing against the best of the best and you're living on the margin. And so those competitions to win a deal, you have to sell and lean into things that are very specific. And I think a lot of what we do as young people is, yeah, we'll hustle for you, we'll work harder for you, we'll be an extension of you, which is very different than experience.
Yes. Yes. And I would add even to that if you are deep in a subject matter that matters to the founder, I've seen so many deals won that way. So you could be a 25-year-old venture capitalist that just understands agentic AI bots better than you. And if you're in it, you're going to outrun any generalist venture capitalist that's 50 years old because they can't be up at night putting 50 claw bots to work. But maybe you can. And when you meet a startup and they know you know this stuff, it shows. They're, you can win a deal based on that. I've seen it done.
Yeah. Shifting gears a little bit to AI. Many entrepreneurs, investors are sitting trying to figure out like what's the future of AI look like? And I like, I don't actually know that's easy to talk about that, but I do look back at the simulation of if we were sitting here 15 years ago, 2011, which I guess a lot of people in this room probably were in middle school or something. iPhone had just crossed 100 million users. You were investing, there's a period of time iPhone just crossed 100 million users. We would have said what are the big companies that'll emerge, I'm curious what people would have said based on your experience but I find it hard to believe they would have said food delivery from strangers to your home, you know, taxis called over your iPhone, staying in strangers houses and yet those are kind of the big apps that were built. So you know when you think about the pitches that we might hear as investors or founders who are looking for ideas to build, yeah, like what do you think stands out the most to you about AI right now that's not obvious?
Well, I mean one way you can get there is by talking about, I mean one thing that I witnessed in the internet so prior to the mobile was in the early days of the internet most venture-backed startups would spend 20 to 40% of their venture dollars on Sun and Oracle and that's how they set up their web servers. And I think when you're in an early phase of a technology, everyone's interested in differentiation. No one's thinking about unit economics because you just want to get out there and wow people. You know, five years later, almost all of the websites had switched to Linux and open-source and MySQL. It's completely different stack. And I think it was just you went towards optimization. So I expect we'll go through that window. I don't know what it'll mean. There are certainly inference focused chip companies that'll tell you that's exactly what's going to happen and open-source models and there like so but I do think that transition, and I think companies like Cursor have already been forced into thinking that way. There are other things we've seen before, companies moving up the stack. You know what Anthropic's done to Cursor. We've seen that movie before. Yeah. And there's lessons to take from that. I don't, you know part of why Uber happened is if you look prior to the mobile phone shipping, automating the location of every car would require you to put personalized hardware into those vehicles. And people had done it. There were systems inside of taxi cabs. You've seen them before. But imagine outfitting every car like and you know who did this? I think some of these people that were trying to do like car rental companies based on cars you own. They had these kits you like you're crushed, you know, and so but the minute the mobile phone's there, you don't have to install this hardware. And so it's a massive unlock. So that's the kind of frame of mind you need to be like what things could happen here that are enabled by this technology.
I mean there's definitely a thread that's connected which is do you, you know, being on, if you're living on the edge of something and we meet an entrepreneur who's studying the edge so much that they are stumbling into these insights. Do you think that is the thing that you should be looking for in an idea right now? I would just be... or is it more like you just want to be on the field and building and actually a lot of this doesn't matter. You just need to be getting the reps learning to find the idea.
Here's what I would say. So you and I were talking about this a little bit before, but the obvious stuff is priced in right now. Like these are the highest valuations, biggest dollars. So like I don't think it's a good use of marginal capital to say, 'Oh, I'm going to either fund a competitor to Anthropic or give Anthropic more money.' I don't think either of those is good return. I would be insanely curious about anything that looked unusual. I know that doesn't sound actionable, but I would just have my ear to the ground. I mean, you know, an AI psychiatrist or like I would be wildly open-minded to what might pop up. Do you think... I met a professor that's going to create an AI version of himself because he gets paid really high dollars to consult. I don't know if it'll work, but I would want to know like I would just be wildly curious about anything that seemed unusual. Would you be, would you, one of, yeah, I guess novel is a better word.
When you have, so I guess if you take this over, you've had a 10 year maybe 15 year period between kind of a major platform innovations and as that happens you get a lot of maturity in the business cycle and people what I find especially when we're hiring execs as an example of a company is people try to take patterns and just apply it and force it over a business as opposed to thinking about what the business is and how should it work and it feels a little bit like we were at that phase in this startup of the cycle where the average company was like a SaaS company which is what worked plus AI and I think a lot of the companies that have worked have defied that logic.
And this may get to the young person's game point but I've seen, yeah, some of my partners have wrote letters to their...
Companies saying you have to unlearn everything. Like applying the SaaS toolkit here is not going to work.
Yeah. And so in some sense you deprioritize the traditional heuristics of success. Like in some ways the market size for anything shouldn't really matter that much today because you're creating all these new markets with AI.
Yeah. Do you agree with that?
Yeah. And you know, someone like yourself who is in some of these model companies, if you had access to the API data and there was a company you hadn't heard of that was moving up, that's the kind of... that's like the WhatsApp investment story where all they did was look at the download sheet and see that WhatsApp was rising on the download sheet to find the investment.
Yeah. Yeah. Which... the other topic we're talking about in this new era is unlike software and the internet where you could marginally distribute for free over the internet, today it's super capital intensive in two ways. One, to maybe Sun's comment, it costs a lot of money to run inference today and it costs even more money to run it when you're going through the labs, but most companies are using that. And so there's a high startup cost to serve your customer base. And the second is most companies are raising a lot more capital today. And so just the business environment is very different.
How do you... Yeah, this is a bigger question. We can break it down, but how do you think in general about capital intensity in a business cycle and what it changes about the mindset for a company?
Well, I'd say a couple things. So, one, prior to AI and prior to the current version of venture capital, which I'll talk about in a moment, the proclivity to try harder style investments was always cyclical with how well the venture capital world was doing. So, people get more speculative and open-minded when they're winning. And the minute the market corrects, all that goes out the door. And the reason venture capitalists have stayed away from either long duration kind of I used to call them material science plays or low margin businesses is they're really expensive and when capital's highly available it's easy to ignore. If capital becomes scarce, you can die fast. Like especially like if you took on debt and like you can just... and people forget about that, you know, maybe because you transition to younger venture capital. But anyway, so I do think it's avoided for a rather good reason. You know, venture capital works best in high margin industries and industries where you can predict the time frame because people say Matt Kohler used to say we don't predict the future. We understand the present very clearly. And because if you haven't watched this movie General Magic, I would highly encourage everyone to go watch it. It's free and it's fantastic. And it's a bunch of really smart people that tried to build a smartphone too soon and there were three or four venture-backed companies that tried to do that and they all failed and they all raised a ton of money. And the problem with the material science plays we were talking about fusion earlier. You just don't know when is when.
Yeah. And if when is 15 years instead of five and your burn rate's a billion a year that's a huge problem. So anyway, then I want to transition into... and I think Thrive's part of how this happened so you should comment, but the venture capital world, you know, starting about when I stopped doing new investments, has industrialized. Like the amount of dollars under management, the way you guys are playing the game, the way you've forced I think the Cotés and Altimeters to react to what you're doing, and the fact that I don't know 50% of the brand venture firms have now scaled up to meet that as well. There's just dollars moving around at a size that I don't even recognize. And you may not believe this but like the majority of companies that get hot are approached for preemptive rounds. So they're not out raising money. People call them and say, 'I want you to take our money.' And there's an implicit threat that at least at SoftBank Masa was very very direct about, not implicit, that if you don't take it, I'll give it to your competitor. And it forces everyone to take the money. And so I'd like to... you look at either AI programming or AI lawyers. There's seven companies that have raised hundreds of millions of dollars. And that's not the venture capital I practiced. And if you're raising that amount of money and then you try to put it to work to win competitively, I did live through this with Uber/Lyft, you just start doing very aggressive things from a go-to-market or sales or distribution standpoint. Everybody's market share oriented right now. They're not unit economic. And do you think like... so this is something we talk about which is in a world that is that way, can you be unit economic focused as a company when you have to compete against your competitors who are not?
That's what I'm saying. I think all of those companies, let's leave the big model companies aside and just talk about AI lawyers or AI coders, what's the worst thing that could happen to you? Lose market share, like mind share. That's all anyone cares about. So you price to gain market. Sure. You don't price the unit economics and like you just can't.
