


5 May 2026 · 43m · 22 chapters

Career regret and AI anxiety; why AI progress is real; US vs China AI strategies; venture capital dynamics behind OpenAI/Anthropic; regulation and “AI race” skepticism; practical ways to use AI to learn faster and stay competitive.
Bill Gurley, venture capitalist and author of a book about “avoiding career regret” (and referenced behavioral-science ideas about regret of inaction). Interviewer Daniel Pink is mentioned as an author of a regret book; Mark Cuban, Paul Graham, Ronan Farrow, and Carlotta Perez are cited.
People regret not taking bold actions more than mistakes; overscheduling and earlier career tracking reduce “fascination.” AI anxiety is low-agency; you can’t stop AI. AI bubbles/overinvestment happen but don’t negate reality. US is dominated by proprietary models (OpenAI, Anthropic); China favors open source (Linux-style ecosystem). “Win the AI race” is a finite-game mindset; no finish line. Regulation will likely come, but incumbents may shape it to protect a duopoly.
OpenAI/Anthropic valuations near ~$1T and $100B+ fundraising; New Yorker coverage of OpenAI chaos; Sam Altman’s Microsoft/Amazon deal flow; TED attorney Neil Cotill whose AI prep predicted Supreme Court questions; Alpha School (K-12 AI) and AI-aided pancreatic cancer advances; using AI for restaurant recommendations and for choosing storage-facility locations.
Written by AI. May contain mistakes.
Learn about the high valuations in venture capital for AI companies.
“For open AI and Anthropik, investors are rewarding them with the highest valuations we've ever seen in the history of the venture capital world.”
Explore the psychological impact of career choices and inaction over time.
“Well, Bill, thank you very much for joining us.”
Discuss how modern pressures affect the exploration and creativity of young people.
“I think it's worse today for the young people because there's so much or at least pre-AI, there's been so much pressure to get kids into the right lane, into the right school, into the right career.”
Address the rising fear and anxiety around AI among young adults.
“They don't think like that because of the way they've been brought up.”
Find out how AI can assist in the writing process and improve outcomes.
“I mean, this one's kind of fun because it relates to the book.”
Understand the implications of massive investments in AI infrastructure.
“I'm also very interested in the kind of AI naysayers.”
Learn about the contrasting approaches to AI development in the US and China.
“Well, let's talk then about what is being done because the US approach and the Chinese approach is very different.”
Explore the implications of a global AI race and the mindset behind it.
“Because I can imagine people listening to this thinking, well, why does it matter?”
Learn how OpenAI and Anthropic surpassed established tech giants.
“by focusing on what can we do better ourselves than trying to say, how can we prevent them from doing better?”
Understand the challenges faced by rapidly growing tech companies.
“And he was talking about, you might have seen it, the sort of chaos behind the scenes at OpenAI.”
Discuss the complexities and controversies surrounding Sam Altman.
“a strong opinion on someone like Sam Altman.”
Evaluate potential futures for AI regulation and its implications.
“Well, let's separate what I think is going to happen from what Bill Gurley might want to happen.”
Explore the challenges and complexities of regulating AI technology.
“The incumbents write the regulation and participate in it.”
Discuss how different generations perceive the evolution of AI and its reliability.
“And, you know, he's already had events at the White House where, you know, Sam Altman's there and Jensen's there.”
Examine how AI can enhance learning and curiosity in individuals.
“These are some of the smartest people in the world.”
Learn how AI can be leveraged for increased productivity in various roles.
“I think if you are truly curious and fascinated in a topic, you're using it to get going and moving even faster than you could before.”
Consider predictions about the future impact of AI and the pace of its evolution.
“But think about it this way, because this is super easy.”
Discuss the societal anxiety surrounding AI and its potential to revolutionize education and healthcare.
“But if you never start, you're probably, yeah, well, you're leaving yourself open.”
Discover practical ways to utilize AI in everyday life and enhance knowledge.
“AI needs a really big and good news story that affects the masses and impacts billions rather than just millions, I think.”
Learn how AI can help solve perplexing problems and enhance learning.
“Right, before we wrap up, Bill, three things you've done with AI or use AI for, and that could be one of them that you would love people to do after this.”
Discover how AI can transform your cooking experience and meal planning.
“And I could have just told it, oh, and then apply this math to it and give me the, you know, you can do multiple steps and iterations and it can give you answers.”
Find out how AI can enhance dining choices and recommendations.
“I'll say, what are the top three dishes people rave about at this restaurant?”

Get the gist, explore an idea or ask about something said.
On High Performance Business, what are the key points of this episode?
Automatic transcript. May contain errors.
0:01Bill Gurley: For open AI and Anthropik, investors are rewarding them with the highest valuations we've ever seen in the history of the venture capital world. When people get rich quick, you invite in charlatans, interlopers, speculators, like that's going to happen. And people have already gotten rich quick here. I'm not sure there's ever a finish line to this.
0:26Well, Bill, thank you very much for joining us. But in your new book, you talk about this concept of avoiding career regret. Why do you think so many people struggle with career regret?
0:37Bill Gurley: You know, Daniel Pink wrote a book about regret. And he said in there that there are studies across the globe. So not just in the US, across like different cultures, different countries. And as people get older, the number one thing that kind of weighs on them is what he calls boldness regrets or regrets of inaction. And so it turns out humans are really good at forgiving themselves for making mistakes after the fact. They like rationalize it. Oh, I learned something, whatever. But the thing they never tried kind of is always out there weighing on their brain. And so it's a bit of a like behavioral science problem where when people are young, it's easy to put off the thing that seems a little too bold.
1:24Bill Gurley: And then as you get older and you have more like restrictions on your time and your money, then it's then then it's harder to even consider that you could do that. And so it just never gets tried. I think it's worse today for the young people because there's so much or at least pre-AI, there's been so much pressure to get kids into the right lane, into the right school, into the right career. I think it's well-intentioned, you know, like they're worried about the economic stability of the young adult. But we've lost the time that when everybody, back in my day, but people used to run around a lot more and explore and discover, you know.
2:10Bill Gurley: And I fear that we've traded that for more of an industrial education complex that's putting people in places that, you know, were perceived to be safe, but lack this essence of what I refer to as fascination, which I think is an unbelievable superpower in a career. So do you think that we're removing the fascination, right, from young people because we restrict them more than ever, we monitor them more than ever? And then actually, in a behavioral sense, that leads to people at 18, 19, 20, when we started to think, well, what is out there? Let me go and explore it. They don't think like that because of the way they've been brought up.
2:51Bill Gurley: And they're remarkably overscheduled. Jonathan Hight calls it the resume arms race, but it's so hard to get into college these days that starting in sixth grade, you know, parents are pushing kids into Mandarin lessons and cello lessons and lacrosse lessons and volunteering. And like they're very overscheduled. The young kids are like way more overscheduled than we were when we were growing up. And in some sense, they get taught to grind, but that'll burn out. You know, that'll eventually burn out. And then the other thing, I don't have any analytical study on this, but I do think somewhere around 19 or 20, you get worldly enough to start thinking about possibilities.
3:39Bill Gurley: And it used to be that you weren't allowed to pick a major until the end of your sophomore year at college. So you're 20 years old, and they wouldn't have let you. They just said, no, you can't. You have to wait until that point in time. And I think everyone knows why that happened. But today, at least in the U.S., many schools, you have to apply to a major in your original application. You're applying to a particular, you know, program within a school. And so you're taking a 20-year-old decision to a 17-year-old decision. I mean, I don't think it's one thing. I think it's all those things. And what about people that listen to this and think, no, I just have a fear of AI.
4:15I don't even want to begin this journey because I'm nervous about it.
4:19Bill Gurley: Yeah, there are a lot of people out there that are like that. And I think it's probably growing, especially in the U.S. The polling of AI anxiety is really negative in the U.S. right now. And I think there was a wave of congressmen, especially at the state level, who feel like they didn't move fast enough on social media. and they're very afraid of a TikTok-like conversation with young people that kind of becomes overwhelming. So there's a lot of brake pumping happening in the U.S.
5:00Bill Gurley: I guess I'd tell people two things. One, if you're so reluctant that you're not curious about how you might be better at what you do every day, then I would go back to square one and read my book. I think you're in the wrong job.
5:20Bill Gurley: Because everyone I've met who's really fascinated at their career and super curious and excited would relish the idea of being able to go deeper, faster and know more. So that'd be my first thing. And then look, with that great book, Seven Habits of Highly Effective People, he talks about your circle of influence. Like, you're not going to stop AI. And you didn't stop the personal computer or the internet or any of these things. So sitting around having anxiety about something that's out of your control is not a very high agency decision. And what have you done on AI that has shocked even you the capability and the depth at which it was able to deliver for you?
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7:07Bill Gurley: I mean, this one's kind of fun because it relates to the book. when I was finishing the book, the editor asked me to write the conclusion. I hadn't done it yet. And I spent all weekend and I turned it in and I'd done a classic summarize the book thing. And he hated it. It was the least favorite piece of writing. And he was very frank with me. So I went back to the pro version of OpenAI and I said, tell me 10 amazing concluding chapters in a nonfiction book and why it worked. And it gave me a list of 10 books. And eight of the 10, the author had decided to make kind of an orthogonal move in the concluding chapter rather than summarize.
7:51Bill Gurley: It had like reflected back in a different way. And once I came upon that, I then asked AI, well, tell me a bunch of books that have done that even more. And a whole bunch of ideas popped in my head. And then I rewrote a different concluding chapter that wasn't a summary. And so, and the editor loved it. And so that was like a learning process for me that would have taken, I mean, if I had to read, I'd have to go read 400 nonfiction to get to that place. But it's just an example. I'm also very interested in the kind of AI naysayers. I almost feel like they're making themselves feel better all the time by clinging on to every possible shred of information or data that tells us that AI isn't here to stay.
8:36One of the things I've seen a lot of in the last few weeks is people saying the amount of money being invested in these data centers simply is not viable for people wanting to spend$5.99 or$8.99 a month to access chat GPT or whatever. What's your take on the hundreds of billions being spent on these data centers and whether they really do form part of the future?
9:00Bill Gurley: Well, I think it's interesting, the question is, as you talked about it, because there's this amazing book by Carlotta Perez, where she makes the point that technology waves, successful technology waves and bubbles always happen at the same time. And when it's phrased the way you phrased it, or someone phrased it to you, there's an implication, oh, people are spending too much money, therefore, this must not be real. And the fact that they're willing to bet that much money is precisely because it's real. Could they go over the top? They almost always do. And, you know, you go back to the gold rush.
9:42Bill Gurley: Like when people get rich quick, you invite in charlatans, interlopers, speculators, like that's going to happen. And people have already gotten rich quick here. And so you're going to see a fury of investment and speculation, not all of which will be successful, but it doesn't mean, you know, and there's these great articles about the internet boom and bust where everyone made fun of all these companies that went out of business in the bust. And then some new version of that company emerged, you know, 10 years later and was wildly successful. So the ideas were directionally correct. We just got over our skis a bit.
10:22Bill Gurley: And I think that happens every time and will happen here. But I don't think the implication that the question had loaded at the beginning that and therefore this wasn't real. I think it's the opposite. It happened because it's real. Does that make sense? Yeah, it does. It makes perfect sense. Yeah. Well, let's talk then about what is being done because the US approach and the Chinese approach is very different. For our audience, would you share the sort of different approaches from those two nations? In the U.S., two players have emerged that are investing tons of money in the model business, which are OpenAI and Anthropic.
10:59Bill Gurley: Investors are rewarding them with the highest valuations we've ever seen in the history of the venture capital world. What kind of numbers? Like they're both close to a trillion now in valuation as a private company. Unheard of. Like unheard of. before. And they're raising over$100 billion as a private company, by a factor of 20 or 25, versus anything we've seen before. But those two have kind of emerged as the leaders. Google and Meta, to a certain extent, and XAI are laying chase, but it looks like a two-hort race. And it's all proprietary, which means it's just classic business where you keep everything internal, even though they started a different way.
11:46Bill Gurley: Almost all the players in China are open source, which means they share the information about how their technology works with the world. And that technology wave is something that started about 25 years ago, Linux probably being the most famous example, which is the most pervasive operating system in the world today and open source. And there have been 50 other open source software projects that have been wildly successful. And there's reasons different people do that. But the Chinese government, starting with the, I think, 14th five-year plan, suggested it was a good idea to embrace open source.
12:28Bill Gurley: So they encouraged the companies to do this. I personally think that given enough time, because they do have They don't have access to these best NVIDIA GPUs, but given enough time, a whole bunch of players using open source models, I think will catch and pass a world where you just have two proprietary models. Just based on what I've seen over the years, because they can all learn from one another. But we'll see. I mean, I'm perplexed at how much attention is spent in the media and in Washington with this notion that, oh, America has a three-month lead. And therefore, we need to restrict this and invest here because we got to win.
13:15Bill Gurley: And like, if you're three months ahead, like, it doesn't seem to me like you have that big of a lead. And what is it? And then they start talking about, well, it's going to become super intelligent and program itself and it'll escape exponentially. And I'm like, OK, that's a that's a bit of a stretch. But anyway, it is it is two very different approaches and we'll see how it plays out, especially in the rest of the world. I think America is accustomed to winning in Europe and South America and non-China, Asia with their products. I think they're accustomed to that. And that may not play out that way here.
13:58And why does it matter so much who wins? Because I can imagine people listening to this thinking, well, why does it matter? Everyone will have something that's okay. But I think it actually is such a crucial point to dwell on for a second.
14:09Bill Gurley: Yeah, let me answer the question by telling you what other people say. They think that the system will eventually become super intelligent, start solving our biggest healthcare problems, and then potentially be used as part of government and part of the military. And it's with that mindset that they say we have to win the AI race. I, having spent a ton of time in China, I know how effective and intelligent their entrepreneurs are and creative. And in many fields, they're ahead of us in EVs and solar and batteries. And so the idea that we're going to develop this technology and have some kind of permanent massive advantage over them that then has some implication in how the world is run or managed, I don't buy it.
15:10Bill Gurley: But I'm not being called upon to offer that voice in Washington or whatever. But there are a number of people that do buy it. And the China Hawk message resonates with some of the American populace on both the right and the left. It's not, you know, it's a kind of a bipartisan tool that's used or fight that people want to get behind. so it gets attention. Yeah, you see, I think I'm in your camp. I'm not sure there's ever a finish line to this. I don't think there is. There's a wonderful book, I might have it laying around, called Finite and Infinite Games. Yeah. And it suggests that most of our game strategy we learn from playing games that have a beginning and an end, a game of tennis or soccer or whatever.
16:08Bill Gurley: And the many things are infinite games, which is, you know, the point you just made, like it never ends. So it's like to say I'm going to win the AI race. It's like, oh, we're going to win the nuclear race. When is the official going to blow the whistle and declare the victor? Like it doesn't happen. And the idea that you're going to keep a nation like China from using AI and developing AI, I think it's foolhardy. to think that that's even possible. And we might do better for all of our citizens by focusing on what can we do better ourselves than trying to say, how can we prevent them from doing better?
16:53Bill Gurley: It's kind of an odd mindset from my point of view. Yeah. Let's talk then about that because it's very interesting this situation in the United States where we've ended up with two main players being led by two powerful male individuals. I think the first question for me, which I haven't really managed to find the answer to, Bill, is with all of the money that Apple had and Google had and all these other big players that were already hugely wealthy at the very beginning here, how did OpenAI and Anthropic get the jump on everybody and end up as the two who were ahead here? One easy answer is, you know, look, that's the history of Silicon Valley and how these things work.
17:32Bill Gurley: kind of how did Yahoo and Microsoft, like Google, emerge? How did, you know, these things, like, it's kind of constant disruption and innovation. There's another element that is new in the American venture capital ecosystem where there is so much money available for the winners because some of these investors have institutionalized and gotten really big, and they've come to believe in power laws and network effects. We could explain what those are if you think your audience needs to know. But it means that in technology, oftentimes, you know, once someone gets a lead, it becomes self-compounding and they get bigger and bigger.
18:19Bill Gurley: So now you have investors that are confident investing ahead. And what this means is these companies are raising and burning more money than an incumbent would be comfortable doing. And that's part of how they got the lead. I mean, let's talk about Google, for example. You know, for many people, the starting place where they type in a question used to be Google, and now it's, you know, OpenAI or Claude. And you could say Google should have done everything in their power to prevent that from happening. But they had one of the most amazing cash flow printing machines in the history of the world running.
18:58Bill Gurley: And to make sure that that didn't happen, they would have had to put that at risk. And that's a hard thing for a management team to get behind. And they didn't know what the consequences would be. If they could run it twice, which is a poker phrase, if they could run it twice, they might do it differently at this point. But we kind of are where we are. There was a recent article actually by Ronan Farrow in The New Yorker. And he was talking about, you might have seen it, the sort of chaos behind the scenes at OpenAI. Oh, yeah, I did read that. And I think people are loving the fact that these companies with all this cash are in chaos, right?
19:37But also, is it not the most understandable and normal thing in the world? Because they're dealing with cash like no one ever has before. They're raising investment like no one ever has before. Dealing with valuations no one has ever dealt with before. But also operating in a technology field that no one's ever been before. So it sort of has to be chaos, doesn't it? All those things are true. Yes.
19:58Bill Gurley: When you grow headcount in an organization from one to a hundred to a thousand to ten thousand in rapid time, it's almost impossible not to have chaos. Like, just think about what that would mean. Like, there's new people every day. You don't know who they are. People are getting assigned management roles that have never managed before just because it's growing so fast. There's no way for that not to happen. And so, yes. And when the burn rates, you can't give somebody$50 billion in venture capital. They can't go use that effectively without taking on a massive burn rate. which is another thing that can kind of lead to chaos because it's hard to know what your real unit economics are once you get comfortable burning a billion a year, three billion a year, 10 billion a year.
20:57Bill Gurley: What's the constraint that causes you to not do this or to do that? and like it gets, yeah, I think I've never heard anyone describe it the way you did. But now that you have, I think it's a good lens from which to consider. I think so. And also like they're doing things we're not doing. So therefore, it doesn't sit comfortably with us. If they're burning 10 billion a year, once you've done that for two or three years, it's the norm. It's only abnormal to the people that aren't doing that.
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22:45Bill Gurley: yeah well if they ever run out of money it'll be abnormal also that is true um everyone has a a strong opinion on someone like Sam Altman. Where do you stand? Well, one, he's probably pulled off the most Herculean biz dev deals of any entrepreneur I've ever seen before. And so, you know, while the relationship with Microsoft appears rocky, he gets Amazon to write another$40 billion check. And that's after everything in that article, because most of those things, the article did a good job of kind of aggregating everything, but many of those data points were already out there. And so you've got all that data, and Microsoft, one of the biggest companies in the world, had bet on this company, and that relationship's fraying.
23:46Bill Gurley: And they get another one of the biggest companies in the world do part with$40 billion. That is unbelievable. Like the brinksmanship that must be required to go pull that off is just, it's breathtaking. And so, and, you know, Paul Graham once said that Sam's the most ambitious person he ever met. Paul Graham's met a lot of people. And so, you know, unbelievable biz dev skills and highly ambitious. and then you can sprinkle in the data that you read in the article. And I think that's a complex individual, but certainly one that's effective. But also someone who's incredibly powerful. Where do you stand on the conversation?
24:31Bill Gurley: Yeah, and has left many past relationships sprayed. Yes. And there's data in that too. um so look i mean in the in the history of silicon valley you know whether it's like steve jobs you know early days of bill gates like they're not perfect humans and there are plenty of data points of them kind of uh learning along the way um being sharp elbowed and uh but but but sometimes they mature in elegant ways, as I think Steve did for sure. And so the question is, is there still room for that? If the behaviors that are outlined in the article never subside and constantly come up again with even bigger stakes, there's always a chance that that won't end well.
25:26Where do you stand then on what the future of these businesses look like in terms of regulation? Are you a government regulation guy or are you of the mindset that, listen, Sam built it, Sam can run it, Sam can own it, and if it means he can control billions of people on the planet, so be it?
25:43Bill Gurley: Well, let's separate what I think is going to happen from what Bill Gurley might want to happen. So let me do the first part. For reasons that I don't fully understand, one of the biggest mouthpieces of of doomerism is Anthropica themselves. And I think, you know, you could I think that's just a fact. They put out more negative fear about AI than any other company. And that is starting to have an impact. And it's having an impact on these data center fights. Many, many states are trying to block it. And it's having an impact on the consumer sentiment in the U.S., which we already touched on, which is high, anxiety high on AI.
26:30Bill Gurley: And you already have a movement at the state level to want more regulation. for the other point I made, that they view this as way riskier than social media and they feel like they move slow on that. So I think the regulation's coming and it may come even faster sooner. Personally, so I'll go into my thinking, I've never been a big fan of regulation. I, in fact, gave a speech that's on the internet with like 4 million views about regulation and regulatory capture. I find that the incumbents often write the regulation to improve their lot in life and to block competitors from coming. And, you know, this Professor Stigler at Chicago won a Nobel Prize for figuring this out in the late 50s.
27:25Bill Gurley: So it's not my idea, but I certainly believe in it. And I'm not a no regulation guy. I'm not like a strict libertarian. I think you have to look out for safety and concerns. My fear is, you know, there was an article in the paper just the other day that was talking, I forget which state it was, it's some state like Nebraska. And it said OpenAI and Anthropic are wrangling over the terms of the state legislation. And I'm like, why are they writing any of it? Like, why are they in the room? You know, but that's what happens. Right. The incumbents write the regulation and participate in it. And I hate that part of it.
28:09Bill Gurley: So I'd feel way better about regulation if I thought that the people were doing it weren't compromised by the players themselves. It's hard with a technology that's new one. I talked to one senator and he said, how do you regulate something you don't understand? And it's not like you could say, list the top 10 U.S. regulations that have been most effective. No one could answer that question. Like, it's hard and a messy thing to go do. So I guess I recognize why it's probably going to happen. I think it's going to accelerate. I'd be very worried that the incumbents write it in a way that reinforces a duopoly.
28:53Yeah, you know, I kind of, I look at Donald Trump and I think AI is so much about control and power. You're a guy so much about control and power. I'm surprised he hasn't gone harder and faster to try and take control of this space.
29:05Bill Gurley: Yeah, I mean, it's, there's a lot of interested parties with a lot of money. And, you know, he's already had events at the White House where, you know, Sam Altman's there and Jensen's there. And like the most powerful people with all the money at stake are there. And so I'm sure that plays a role. I don't know.
29:31Bill Gurley: There's a chance the anxiety level gets so high that it will be popular to come up with a solution here from a regulatory standpoint. point. The China factor, though, looms large, because if you start pumping the brakes on all this stuff, someone else is going to scream, oh, but we only have a three-month advantage, and they're going to run past us. So it's a complicated situation. I still think we're in a very interesting place with AI, where, particularly for people of our generation, it feels new, right? Maybe if you're 17, it might not feel that new, right? I guess It's my 10-year-old son probably in his head thinks AI has been around forever because it's been there for the last four years.
30:15He might not even remember life before it. But a lot of the people of my age that I talk to, they say, oh, I've used it. It's not that reliable. Or, oh, I've used it. It didn't give me the answers I was looking for. I don't feel people are fully understanding the speed of improvement of AI. What would you say to those people that gave it a go?
30:33Bill Gurley: I couldn't agree with you more. I, through one of my nonprofit activities, I hang out with a bunch of professors and I heard this from them. These are some of the smartest people in the world. They got it to fail on a test they did two years ago and then they put it out of their mind. And I say the exact same thing to them, which is, have you done that exact same test over and over again with each model? Because you need to understand the rate of improvement. And it is vast. It is really improving quickly. And to your youth thing, I've always felt that young people had a massive advantage in venture capital, partially because they're just more open-minded to things as they come along.
31:16Bill Gurley: And the notion that a young person can use the new technology, even going back to the VCR, right? There are all these jokes comedians would do about how the kid could program it and the parent couldn't. You know, it's just a classic historical artifact. And I work with CEOs and founders that are, you know, finding, like, getting a 24-year-old into their companies better than a 48-year-old just because of this open-mindedness to AI. Like, it's a real, they have a plastic brain about it rather than a skeptical blocking brain. and it has a massive impact on how they adopt the new technologies. So let's talk then about the role of AI in this, because is AI doing all the exploration for us now?
32:09Did it actually remove us even more from needing to do this for ourselves? Or is AI, because people talk about, oh, we can explore the whole world now that we have AI. Well, we can, but AI does all the exploration and we just need to sit there in front of a screen. So what's the impact on that?
32:25Bill Gurley: Mark Cuban had a great quote in the past couple of months. He said, there are two types of people in the world, those that use LLMs to learn faster than ever and those that use LLMs to skip learning altogether. And I love that notion. I think if you are truly curious and fascinated in a topic, you're using it to get going and moving even faster than you could before. I just came back from TED, and one of the other speakers there is Neil Cotill, who is one of the top attorneys in Washington. He actually argued the case against Trump on the tariffs and won at the Supreme Court level. And he walked through in his TED Talk, it'll be released eventually, all the different advisors he had in preparing.
33:14Bill Gurley: but one of them was AI. And AI predicted six of the nine questions he was getting from the justices. Almost word for word predicted what would come. And I use that as an example of like, I think that's someone who is probably at the top of their field, maybe the top, leaning, you know, super curious, wanting to be successful and using it to get to an even higher level. There may be legitimate questions of like further inequality divide because the people I see that are most fascinated in their career, in their industry, they are the ones that, you know, AI kind of is a jet pack on their shoulders and now they can fly higher and see further.
34:03Bill Gurley: And, you know, if you're someone who's somewhat ambivalent about your job and you're not spending time trying to figure out how AI may make you more powerful in that role, you're a sitting duck. If there are 30 people all in the same job at the same company, the best way to protect yourself from disruption is to be the most AI-enabled version of yourself you can be. So if out of those 30, you know more about what AI is possible, of what it can do, then you're the best protector. But think about it this way, because this is super easy. You wouldn't go compete with a modern farmer with a hoe and a shovel, right?
34:42Bill Gurley: Like you just wouldn't. And no one would expect you to be successful. You'd be pounding on the dirt while the other guy's already reaping, you know, tons of money. And so if you know you wouldn't do that, then you really have to think about the fact that whatever job you're in, if there's a potential for the AI to enhance your productivity, you need to know what that is and understand what it is and spend time figuring that out. So I still think most people are using AI on a daily basis to answer a question they might not have an answer to or to improve a bit of work that they're already doing.
35:13When you see really high quality use of AI or the kind of use of AI that is going to bulletproof and future-proof the people that are listening to this conversation, what are they doing with it?
35:24Bill Gurley: I think they're extending the speed and productivity of whatever tasks that they're assigned to do and are asked to do. But that ties exactly to both the speed and the quality. So that example I gave of the lawyer, I think it enhanced his quality by figuring out and being better prepared for what might come. I've met local entrepreneurs. I met a guy that runs a business where he builds storage facilities for stuff. And this was a year ago. And he's like, I was thinking about opening a fourth location in my town. It was some small town in Texas. And he asked AI to help him figure out what would be the best three locations for an incremental unit.
36:17Bill Gurley: And he was shocked at how much information came back and how helpful it was even identifying lots for sale. And I think one thing I would tell everyone out there is the more you play with it, the more you start to get a sense of what it's capable of and when you would lean on it. And if you don't start that process, it's almost like an exponential learning curve of using it, if that makes sense. And so you'll start to understand more ways to kind of extend your capabilities once you use it. But if you never start, you're probably, yeah, well, you're leaving yourself open. And a few people understand it in the way that you do.
37:00So if we look into the future for a minute, does the future look like it looks now in 2026 with AI alongside us? Or is the future because of AI so different, we almost can't even predict anymore?
37:13Bill Gurley: I'm more likely, this is a very personal question, I think, because there are people that are out there that are way on opposite ends of this spectrum. I think the world bends kind of slowly. Like there's a lot of friction in the world, just like every day getting up, traffic, you know, building buildings. Everything's a little slower than people think. So to think you're going to blink your eye and robots are going to build everything and there'll be UBI and no one works, like there's very little chance something like that would happen quickly or cancer being cured. Like things take time to run trials and all this stuff.
37:54Bill Gurley: So I think it'll move slower than people perceive. And when I say people, in that case, I'm talking about some of the visionaries that are saying, you know, half the people be unemployed and cancer is cured in two years. Like I don't see that happening. and look people tend to get
38:17Bill Gurley: anytime these new things come along there's a period where people get overexcited and that resets and that happened with the internet like it happened with the gold rush it happened with the tulips back in the day like it's a natural human tendency to kind of get out over our skis and as someone that's seen so much and spoken to so many people about it what's the one thing you've heard about what AI could be doing in a few years' time that made even you open your eyes and think, that is what our future could look like? Okay, wow. I think that there is the possibility that people build models that are not LLMs.
38:55Bill Gurley: So famously, Tesla's full self-driving AI product, that's not an LLM, that's not the same technology that we're using when we type prompts into these other AIs. And there's a scale and capability and data set possibility in that dimension that could be pretty interesting to see what's possible in healthcare, what's possible in robotics, that kind of thing, as more and more of those things are developed. Once again, I think they're a little slower than people realize, but it will be fascinating and it'll be surprising to people. I think the biggest thing, just to touch on before we finish here, Bill, is this idea of anxiety, right?
39:45Because while there's anxiety from the masses, there isn't progress from the masses. We have to have a situation here where the more that we feel good about AI, the more we're going to use it, the more we use it, the faster it grows, the faster it develops. It's almost like, actually, we feel we don't control AI. So much of the power is our hands because we can grow this thing. What would you say needs to happen or what can we talk about now that just helps to ease this anxiety around it?
40:15Bill Gurley: It's funny because when you say this, I'm now being forced to think, oh, well, what could emerge that consumers get so happy about? And it just reminds me how things are slow, not fast, like just in the real world. So one idea that popped in my head, there are people that believe that K-12 education could be vastly improved by AI. And there are examples like Alpha School here in Austin that a lot of people are pointing to. But for us to run the proper test to see if that's true across a broad array of students, across many states, different income levels, that's going to take a long time to go figure that out, right?
40:56Bill Gurley: Right. So while I might be hopeful that that's going to happen, it is not going to happen overnight. But that's an area where it could happen. Health care is another area where where we might start to see pretty. There were some positive data out this week on pancreatic cancer and the solutions that led to that. Both had used AI in their development. And so people are talking about that. The health care is a big area where where it's possible. It can be impactful. I think that that's what AI requires now. AI needs a really big and good news story that affects the masses and impacts billions rather than just millions, I think.
41:39Bill Gurley: Not just helping you figure out what's wrong with your sync. There you go. Which, hey, let's be honest, when you've got a problem with your sync, you still need AI to solve it for you. AI's great at that stuff. I mean, that would be one thing I don't know if people have tried. But any device or system in your life that's not working, you take a picture of it and put it in there and you start getting answers fast. I think you're right. And people don't do this stuff. Right, before we wrap up, Bill, three things you've done with AI or use AI for, and that could be one of them that you would love people to do after this.
42:11So let's say, number one, take a photo of something in your life that's perplexing you and let AI give you an answer. What's the next thing you'd love people to do?
42:19Bill Gurley: I'd say learn faster. So if there's a subject in your life, and it could be a personal subject or something that relates to your career, some fascinated thing that you don't understand or might want to understand, you can have it go write a 20-page paper on a very specific topic area. Like, I'd like to, you know, know more about this precise thing. And you'll be shocked when it'll come back. And it might come back with 20 different links to articles you didn't know about. I mean, it's so powerful. And I think once you start playing with prompts, you'll realize how directive you can be. I mean, I remember one time I did a deep search like this and I asked for a bunch of numbers.
43:08Bill Gurley: And then I took the numbers and I was putting them in a spreadsheet. And I could have just told it, oh, and then apply this math to it and give me the, you know, you can do multiple steps and iterations and it can give you answers. And, but you don't, you don't start to, I already said this, I'm sorry for being repetitive. You don't start to figure out what's possible until you play with it some more. And now it's getting better at the, the prompting you back. That second thing where I said, and then I put the numbers in and did this. Now, a lot of times when you get the answer, say, would you like me to go a step further and do this next thing?
43:46Bill Gurley: It'll like it'll talk you into it and then do it itself. So it's it's really great. I think it's amazing at that. The kitchen. It's amazing. Like you could just put in the ingredients you have. You want to you brought home a chicken and you want to cook it in a different way. You can put in the most incredible data and ideas, and it'll take you to places you might not imagine. When I'm at restaurants, I usually use Gemini because Google has all the Google review data. I'll say, what are the top three dishes people rave about at this restaurant? Or I'll take a picture at a wine list. Like, you know, it's just, it's unbelievable what it can respond to quickly, especially with dense amounts of information.
44:44And listen, if all it ever gives us is a great dinner with a great glass of wine, it's done its job.
44:50Bill Gurley: That's pretty good. Phil, I really enjoyed that conversation. So much fascinating stuff in there. And I think both of us feel the same. Let's see what happens. But while we're watching, let's also be exploring.
Venture capital legend Bill Gurley joins Jake to challenge the "AI doomerism" narrative and expose the high-stakes power play defining our future. He argues that AI anxiety is a low-agency response to an unstoppable shift, warning that the real risk isn’t the technology itself, it’s the choice to ignore it.
Bill pulls back the curtain on the "safety" movement, questioning why the leading AI giants are suddenly the loudest voices calling for regulation. He explores whether this fear-mongering is a calculated move to invite state intervention, potentially allowing a handful of companies to write the rules and lock in a permanent monopoly.
Bill also reframes the US-China AI race as an "infinite game," questioning if America’s proprietary approach is actually prepared for the scale of China’s open-source strategy.
'Bill Gurley's new book Runnin' Down A Dream is available to purchase here: https://amzn.eu/d/0cCYDQH0
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