Bill Gurley on 'Running Down a Dream': hyper-curiosity as a career edge, AI as a superpower for self-learners, and warnings on retail VC access

Bill Gurley. He is the author of Running Down a Dream. Bill, welcome to the show. Thank you so much for taking the time on a busy launch day. Congratulations on the launch. It is a busy launch day.

I Yes. Yes.

How many podcasts are you doing this week?

I can't imagine. It's some number beyond my comprehension. Well, we appreciate you taking the time uh to come chat with us. Uh why

Well, before we jump into everything, I got to say somebody, I think it was a week or so ago made a fake TVPN graphic that was pretty silly, and I just wanted you I just wanted you to know we didn't make that. That was somebody.

Okay. I almost I almost emailed you about it, but uh

No, I tried to jump in on the parody myself.

Yeah. No, you did, but then I was like, wait, does he I I don't know.

Well Well, we did. We did early on when we were uh a little smaller and a little more free loose with the jokes. We we posted a picture of Bill at uh a basketball game as a spotted. And you replied and said like, "No, the person next to me is like the owner of the team." And the whole joke was like, "We know you. We don't know basketball,

but we're doing the paparazzi thing.

Never heard of him."

Uh but we're very excited to have you. Uh what what uh why the book now? what was the what was the impetu what was the impetus for actually writing the book? Yeah, look, I I think, you know, especially for a show like your own, I you know, I'm known as someone who spent 25 years in venture capital and um the book's not really about that, you know. So, I I developed a side passion project that started about eight years ago on this topic. And it was at a time where I was reading a ton of biographies and I noticed a through line um between three different subjects of things they were doing that I kind of felt most people weren't doing but could do. And uh I put it together. I gave it as a presentation at my alma mada where I got my NBA and they put it online. Few people noticed. James Clear noticed. That was one of the things that kind of woke me up to the possibility. And as I began to um hang up my boots in venture, which takes a while, um I turned my attention to this and it was something that um meant a lot to me. I could have written a book on VC. I I don't know how many humans that could have possibly helped, but a small fraction compared to what I hope this can do.

I I mean, I think the projections are by 2030 there'll be more venture capitalists than people if the trend continues. So, uh I I but but it is interesting point. Maybe I made a mistake. I do feel like this is a book that you can read if you're a venture capitalist insider startup founder and be like, "Okay, I'm I'm I'm seeing the world from Bill's perspective. That's helpful." But I could also give this to someone who's never heard of you or venture capital or knows what a safe node is, and they could get value out of it. And I'm interested to hear your thoughts on the the translation that's happening right now around AI narratives as they break into the public consciousness. We saw this with that viral X article. Something big is happening. I had that forwarded to me by family friends. I overheard someone in a restaurant talking about it who clearly is not, you know, an investor in an AI lab. They're just some random person and they realize that there's something happening. And I'm wondering about these transitions of communication that's what's happening in Silicon Valley is going to have an impact and how what you've seen in the past translates to average Americans. I haven't seen, you know, if you think of, so first of all, the venture capital community appropriately gets excited about these big tech waves because they lead to disruption and they lead to kind of accelerated um um new wealth creation around these companies that break out. And that's happened over and over and over in my career. And I don't remember one I mean if you take the mobile wave or the PC wave or the client server or SAS I don't remember any of those kind of being thrown at the public consciousness this fast. And so I do think I do think it's different this time on from that front alone. That said, you know, um we've had pretty high market caps for tech companies for a long time now, starting with the dessert period, and you're getting to a place where um you know, anytime the market switches from from half full to half empty and a skeptic's mindset, um you you do we have had those moments like so so maybe not driven by the wave, but we certainly have those moments. And it's all okay. It will always be okay. I think people freak out. Buffett says he's a net buyer of stocks. If if people are intellectual and curious and hungry, they should be sharpening their pencils right now trying to figure out where where they want to find entry prices on some of these companies.

Yeah, that makes sense. I mean, I I it feels like a lot of the book is about finding a career, and I feel like that will resonate specifically with people who are

Yeah, it with me because when I was thinking about when when John and I first met, we had both built some companies, we both invested in some companies, but we were trying to find our life's work. And it was such a it's such a pain like that period where you're you're searching is if you if you're a high agency person, you like doing a lot of things, it can be deeply painful because you're like, I want to be productive. I want to be I want to be making the number go up, but I don't have a number right now. And and if you had asked either of us when we first met, hey, would you ever think about broadcast media? Would you ever think about being in front of a camera? both of us, you know, John had made some YouTube videos, but it was just for fun. And if and if a big, you know, if a network like CNBC had said, "Hey, would you guys consider uh, you know, hosting a show?" We would have been like, "Yeah, like thank like honored, but no way that I never imagined." And then you sort of just

and and so as somebody who like wants a lot of control over their life and their destiny and and like feels like they have historically have had control, that period of just like searching is like is is painful. And I feel like a lot of the book is helping people through that moment. So in some ways when I got our copy I was like wow I really wish I had this

I' I'd like to go back to the word you the phrase you used of high agency. I I I think that um one of the problems that is that has kind of evolved is that our our college our common college pathway has actually become more restrictive and I think there's less agency and kids are being encouraged. They have to sign up for a major before they ever go to the college. They get stuck on these pathways and there's not a lot of exploration. there's not a lot of of search for creativity or obsession or the kind of thing that that really gets you going. And I think the journey you went on is perfectly fine. I think that's another thing which is um letting it be okay for people to bounce around and see what they can find because once they latch on and we have examples in the book where that doesn't happen till 40. Sometimes it's at 30, sometimes it's I didn't become a venture capitalist until I was 30 and that was clearly my dream job. I mean the first two two stops were were fine and interesting and building blocks towards that. Um so so I think it I think I think that is part of the message is to get comfortable with that and give people permission to do that type of exploration.

Yeah. Enzo, Enzo Ferrari, Estee Lauder, I think the Red Bull founder, too, all were, I think, in their 40s when they started their companies. And so there's this intense pressure in our industry and everywhere to figure out a job and then attach your, you know, make your entire identity that job and it's so it's so constrictive.

Yeah.

Yes.

Yeah. What are some I I circle back to to the the first question just about this AI stuff that's out there. I think there's this massive paradox where if you are not engaged at work, if you don't love what you do, you know, you go home and you don't try and improve on your own time. Um AI feels very threatening for high agency people who are kind of on their own custom career path, which I hope this book encourages more and more people to be on. AI is like a superpower. There's like you can learn constantly like you can find people who you should be connecting with. You can you can have it do things for you so that you're operating with the power of more than one person as you move forward. And I I I just think that's quite a quite an ironic paradox that for certain people this is the best of times. The best like like there's never ever in the history of the world been a better time to self-learn. Mhm.

Like it is it is all out there at your fingertips. It's like magic. Um but you have

Yeah. I think the ability to to uh you can anyone can ask a dumb question at any point all day long and you don't have to be you don't have to be embarrassed about it. And I think that that is underrated today in terms of how many if like generally no you know there are no dumb questions and yet people still don't like asking dumb questions to their peers or or mentors or or whatever and I feel like that's an underrated uh element of of AI today.

No doubt.

Yeah.

No doubt.

What do you think about uh hyper financialization young people day trading meme coins all of that? It feels like a trap for young people where it can feel like you're learning about AI or learning about technology, but then instead of actually building a product, creating value, you're sort of just trying to shuffle chips around the poker table and ultimately uh just take risk.

Yeah. I mean, based on my understanding of day trading in a in a Wall Street context, you know, prior to maybe the crypto world, I don't I'm I'm not aware of any signal that suggests that's a durable skill. And I think the data points the other way, but but but one of my messages is like do what you love, do what you're passionate about. So if that's if that's the thing that you're going to wake up every day, you know, I I I don't want to I don't want to be discouraging.

Yeah. Yeah. Yeah. just maybe you'll land or start a fund that it takes it really seriously and creates some some captured value or

you know I was probably overly skeptical of of at least many of the crypto messages that were out there but the the stable coin rails seem like a real real innovation and and something that has scale

and and I think maybe we're still yet to see some disruption coming down the path.

Yeah, I mean we just talked to the Collison about that. Uh Ken Griffin started as a day trader. He was in college. He was he was buying convertible debt and he was, you know, looking at like where the convertible debt was mispriced and and and made a bunch of money and then grid into a massive team with a fund and high frequency trading arm and all this stuff. Uh what are you making? Oh yeah.

I was just going to say the thing that will differentiate you more in your career than anything else is to be the most hyper curious person that that's trying to do this thing. And and once again, that's that's put on steroids with these AI tools. But if you are the most curious person that's constantly learning in your field, you will do extremely well. And I I said it in the book, but I'll say it here. Um I can't make you the most talented person in your in your, you know, company or your group or your field, but you have no excuse not to be the most knowledgeable person because the information is all out there. What kind of what kind of things were you doing to learn about industries and and companies, you know, at in the beginning of your venture career that maybe you'd be using a deep research query to do today? But

well, the first thing I mean the first thing is you develop and I think this is all the great VCs in the valley. You you develop this hyper FOMO uh of anything and everything. And um one of the way one of the reasons I know that um that it's time for me to move on is I I haven't I haven't put together a claw about yet, but I know my older self would have done it immediately. And and it's just that kind of thing. You can't sleep on not knowing something, you know, or hearing that there's a company you don't know about. And um you developed that as an instinct like as a positive tool um to just be hyper paranoid about new companies, new things, new information, new technologies.

Is venture capital eating the world? Are is venture capital scaling so much that it's eating into other asset classes? We're seeing mega funds. I'm interested to think about what's durable about your approach to investing. What's additional? What's substitutive? How is venture changing? I think from the minute I entered venture to to today, venture has gotten nothing but more competitive. It's uh it it it as an asset class, it's gotten more and more competitive and people get more and more aggressive. Um we're in a very interesting time where people have grown funds to the size of of equivalent to the largest PE funds

and um they're moving money um especially you know you just had the Collison on you know you look at the stripe or the data bricks case they're using those large funds to convince the companies to stay private longer maybe forever that's just a very different world than the one that I grew up in um I think they turn around And the people that do those rounds turn around and tell the LPs, their their investors, look, if you want exposure to these growth years in these companies, you need to come through us. And so you they've, if I were using cynical words, I'd say they've hijacked the the the growth years of these early IPO companies. You know, Amazon went public below a billion in market cap. Like it's hard to fathom that, you know, today with with what we have going on here. And that's

what's the what's the solution though

because because there's different there's different you know Angelist has been

uh you know available and scaling for a long time now. Robin Hood has their new

Yeah, I know. I know. The problem the problem with getting the retail investor into this crazy world of venture capital is most venture capitalists are well aware that in a fund of 10 investments, seven are going broke and bankrupt. And I don't know that the retail investors got the right frame of mind for that type of activity. I also um there's a reason that public companies have public audits and file these these financials in the way that they do. And I can tell you when a company gets ready to go public, everyone sharpens their pencils. The auditor, the lawyers, everyone really tightens up. And I think every venture capitalist knows that that numbers that are in a PowerPoint may or may not be correct. But I don't know that retail investors know that. So I think it could I think it could be a dangerous world to go down that path you're talking about.

Yeah.

Um but the I ideally the thing to do would just to make it a lot easier to be public, lower the cost of being public really scrutinize the cost of of DNO insurance and the lawsuits that come to the table because that makes people not want to be out there on the field. It it it would require the SEC to stare themselves in the face and say, "Look, the number of public companies in the US is half of what it used to be." And what is that a problem? I think it is, but is that a problem? And what are we going to do to fix it? But it there's not an overnight fix. It's going to take a it would take it would take someone being very determined to to make it happen. Do you think that there's a world where the AI backlash is less if the big labs got out earlier? I'm just thinking about the average American can't get allocation in SpaceX anthropic open AI and they're seeing bills go up and they're worried about AI but they don't have exposure and and if they could at least see that they're somewhat allocated to that

in the same in the same way housing prices going up sucks until you buy a house and then

the way you describe it sounds more like how a politician would describe But then I actually think it would might play. I don't know that there are that many retail investors out there going, "Oh, my job's under threat from AI. I wish I could own anthropic." Like I I mean,

well, isn't that part of Isn't that part of why I mean this sort of fear-based uh fundraising approach that that the lab, you know, some of the labs have taken where if if somebody's telling you your job's going to go away, of course you want to give them as much money as you can as a as a hedge,

you know. I I don't look I there there's an interesting irony that if you wanted AI exposure, you're pretty good just owning the index. Nvidia is such a large part of the index. You have exposure to Microsoft and Google and Facebook. Like I I don't know that you need to be in that place. And we are now already at a place I would say, you know, every time there's a new technology wave, um people get rich quick. When people get rich quick, speculators come in. Charlton's, you know, those kind of things. And eventually that leads to a bubble. People are confused when they think, you know, they say, "Oh, you you say it's a bubble, you're anti-age." No, the fact that it's real causes the bubble and that's why fools rush in. I mean, the beginning of the gold rush, there was really gold there. They were finding it. At the end, the point,

you know, it got speculative and so funny.

It will get speculative. I think it would be really ironic if we, you know, invite retail investors into a Goldman SPV of open hour an entropic right before the re which I think would be the most likely thing that would happen.

Sure. Sure. Uh

how how are you uh what are you thinking about around China as of today, February 2026?

Uh we have distilled Gate this week. Uh a lot of people are talking about it. Uh but what's on your mind?

Can I ask you a question about that? This is this is uh remarkably naive on my part. So these model companies are saying that their their API was hit 16 million times. Is that correct?

Something like that. I don't even know if a bunch of

How how did that happen? Are you not tracking who connects to

Yeah. You set up a whole bunch of different like front companies or you're reselling access. So if you go to the uh if you go to the iTunes app store right now, there will be an app to set up 16 million accounts

that or yeah or or if you just you can go to the app store right now and look for like chat AI and it will hit the other APIs but you're going through an American company maybe they don't have security. So there's a lot of different ways to to exfiltrate data and then also a lot of data just hits the open web because you go to chatbt, you run a deeper research report and then you just publish it on your blog or or on the internet.

But now they've been able to to those things down and now

I I you know I share the skepticism Elon does and it this goes way back to my speech at all in on regulatory capture. I said then and I still believe now the biggest threat to the US um let's call it AI hedge me is is the Chinese open source models and the developers um even in the US that are working on their own are using those and you can see that on all the on all the the uh the tables that are out there and so um

it is a highly competitive like just globally competitive reality that that in an ecosystem where there's six to 10 open source models that can all learn off of each other that's going to be high like that's going to be a really incredible primordial soup if you will for innovation to evolve and I fear ma mainly because I'm well aware that like open I mean anthropic is the biggest spender on lobbying whatsoever. I always fear when these things come out that they're um just trying to encourage more of that regulation. And if that happens, I think it could be like if they try and make it illegal to use a model that has any Chinese um

like ancestry. Um I think that could end up in a really weird place. Um and and and the place to really pay attention to and look out for is um who's going to serve the rest of the world. In the internet era, there was a fence around China and the US companies serve the rest of the world. If we if we get super heavy on US regulation, you may find there's a fence around the US and China serves rest of the world. That's what I'd be worried about.

How are you thinking about great power competition more broadly? Like I'm an American bald eagle. as American as they come. At the same time, I feel like uh I've been worried about a confrontation over Taiwan for years.

Things there's been trade wars. Yes, and things are tense, but nothing's really happened. Is China somehow like underrated in your mind? Is the geopolitical risk overstated in some way? Like what are you seeing that's not consensus? If you've seen some of the stuff I've posted and and and and I think the stuff I'm posting is highly consistent with Elon's point of view, it it it comes from a place of if you're going to declare that that there's

this this relationship that we need to optimize, I think, and and if your goal is to lower the risk of any any major glow up blow up between the two, I think it's imperative to have as much knowledge as possible. And so one of the things that I don't like is when you see people out there spreading rhetoric that's just not consistent with the reality. And so I'm I'm just like let's get eyes wide open first. I also think that there are things we could learn from China about how to run infrastructure in the US. They're clearly better at it than we are. And if you just, you know, close your ears and say, "Oh my god, they're the evil competitor and they cheat all the time." you don't ever get yourself in a position where you're going to learn, you know, from them maybe what they're doing well and what we're not. And so I'm I'm, you know, Elon, we were I guess he was on Cheeky Pint with the gentleman you were just talking to, John.

Yeah. He he talks about um how competitive they are like, and I'm just like, let's be realistic. Let's not I also worry a little bit that the venture community's gotten into all these military companies because I venture capitalists start to look like wararm mongers. Right. It's ironic way back when when the all-in pod just got started, they were giving uh um oh, what's her name was on the Boeing board. Nick uh Nikki Haley wasn't yet. And they were like, "Oh, she's a wararmonger. She's on, you know, looking after the defense company. Now every VC is in Andrew. They're doing the same thing. Let's be consistent."

Yeah. Yeah. Yeah. Yeah. Um I I are there any other industries that you do think are interesting that sort of butt outside of the tr the typical uh mandate of venture capital? You know like AI fits very neatly into the software continuum internet cloud mobile. Um I thought crypto was a little bit outside of the wheelhouse but a lot of VCs made it work. industrial, energy, defense. These are sort of things that are a little bit outside of the typical software business.

I would I'm I'm going to have to run, but I would tell you one thing.

Um, every time venture cap every time venture capital gets easy, people take or take risk with companies that are less of a great fit for the venture capital model. And when I say a great fit, like they're they're either heavy capex or they have they have low gross margins. They require tons of capital to keep surviving. And and

history's pretty good at at like bringing people back around to how hard those are to do with venture capital. So, it's interesting for me to see those experiments being run. um you know there there was near death with Tesla many times and it's a lot easier to get in those difficult situations when you're using debt and leverage which we're seeing all over these data centers and so um I just a word of warning be careful it ain't easy you know

okay Jordy last question

now we got to let uh let our guests jump but u congratulations hope everybody can get out and buy

running down a Dream. It's available everywhere. Books are sold. Go check it out. And thank you so much for taking the time to come chat with us. We'll talk to you soon. Good luck.

Goodbye.

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