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Bill Gurley

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2025-12-17
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2025-12-17
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  1. Usually successful, which I think then has a bigger impact than just on themselves. The number of humans positively impacted by Danny Myers' success is in the thousands, I'm certain. And I'm not counting customers of Shake Shack.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  2. Really started as a passion project, and I have no financial goals for whatsoever. In fact, I'm going to, as we get to book launch, I'm going to launch a foundation that gives grants to people who want to chase their dream job but don't have the financial wherewithal to do it. And so I'm going to start working on that in addition to P3. For me, it's all about how many people do I affect in the way that McConaugh's dad did or that this book did for Seinfeld. Like some of them saw the talk on YouTube from the UT presentation that I gave and have already reached out and said thank you and they've shared how it changed your life. But the more people I can do that for, I will just be tickled pink. I'd just be so excited because I think when people get out of this pragmatic lane and go do these types of things, they tend to be unusual.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  3. Oh, it's horrible for consumers. I mean, the US healthcare situation, which seems to be getting worse on a daily basis, is a huge example of regulatory cap. Somewhere in the past 10 years, they just told physicians they can't run hospitals. Who other than a doctor is going to go start a new hospital? The amount of competition you eliminated in this one swoop is enormous, just enormous. That's just a single example, but there's hundreds of them in that area.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  4. After 09, we wrote this thing Dodd Frank, and we thought, oh, we're going to make things better. And all you've had is consolidation in banking since. And if you look at the offering, especially at the low end for the poorest citizens of the U.S., like free checking went away, the poor people have a hard time paying their bills so they don't even have the tools to do it because free checking when it free checking went away after Dodd Frank.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  5. It's horrible. There's other things too in this category. The long kind of prevalence of Visa and MasterCard is just ridiculous. Two and a half percent in stablecoins have so much momentum right now. I just think those two companies are going to be in real trouble within a five-year window. By the way, most of the financial problems are pure regulatory capture. Like the reason that there's a problem.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  6. Yeah, no, it's been known for a long time. I uncovered an email from 1999 at Goldman Sachs, which I've posted on Twitter several times where they're like saying, oh, we can use this hot stock to reward our top clients. Like they know what's going on. And the fact that the SEC doesn't get involved really bothers me, but this tokenization thing is a real way to get around it because The crypto community has already decided to use algorithms to allocate and determine price. Like the price and the allocation should just be determined. It's how direct listing works. Everyone knows how to do it. They just don't do it.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  7. Yeah, when the company's coming public, the bankers literally they ask everyone for orders, but then they pick who gets the stock and they pick the price. Supply and demand can automagically pick the allocation and the price. It's not automatically is the wrong word, can algorithmically like this is super easy. Like it's not hard. Why don't they?

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  8. Real The way that an IPO is priced is so god awful stupid. They pick who gets the stock and they pick the price. And I've said it over and over again, but a freshman comp size student and a freshman finance student, if you told him to design the IPO, they would just match supply and demand anonymously. Like it's how every bond is priced. It's interestingly how coin offering works. And so I've become a late to the game crypto. Because I'm so sick of this damn IPO process being broken.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  9. I mean, if you tilt against the investment banks, you got to be comfortable not going to conferences, that's for sure. They owe some really nice funds.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  10. You know, I've been tilting against this insider's game of the IPO market for some time, and I'm very passionate that when you bring a public life.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  11. Think that using open source as a defensive tool instead of an offensive tool is one of the most sophisticated corporate strategies a company can possibly do. It's very hard to do because it goes against all of your instincts. But I would suggest that Amazon and Apple and maybe Meta who has toyed with it should run at the idea of jointly supporting an open source model. I don't think they're doing it, but I think they should because they're incumbenty's at risk if someone else has a massive proprietary advantage.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  12. Yeah, I think the society benefits from that. I use this example. Imagine there's two feudal societies that are all agricultural based. There's two of them, though. In one, once a week, the farmers come to market and just trade goods and then they leave. And the other one, the farmers come to market and they're required to share their best practices with everybody else and then they leave. Going back to this peer kind of example in the book, that one's going to be much more performant than the other one. This gets to Ridley's point about ideas having sex.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  13. You know, if you look at the big open source projects, Linux, MySQL, and you go on the web pages, like you'll see Alibaba, 10Cent, like these companies have been supporting these technologies for a while. But every five years they write this five-year plan, you know, the Chinese government puts it out. Five years ago, they had a huge section on open source. So they're clearly suggesting to the entrepreneurs that the government favors that approach. Going back to Ridley's book and the notion of pure competition, I think this is...

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  14. Interestingly, I found a document online that someone had put together a PowerPoint about the history of open source at China and it's 20 years old. So it's not like they just stumbled into it. I think when you consider that Know go back 20 years ago, the primary criticisms of China was that they stole IP. And so if you're the Chinese government and there's this new thing called open source, you're going to embrace it because there's no fault there because everyone's sharing and everyone. And so

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  15. And by the way, this, I mean, not to divert too much back, but right now China has 10 open source AI models that are all in hyper competition with each other. That is a dangerously effective primordial soup for innovation compared to what we have here.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  16. Paper they wrote was open source. OpenAI doesn't exist without that discovery which happened at Google In open source, you know, they just exploited it the fastest.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  17. If I have this particular genome sequence all of a sudden, like I get this huge proprietary window in the market, it's just nutty.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  18. If someone comes into our office and talks about patents, we roll our eyes because none of the types of businesses that we've backed at benchmark in Silicon Valley are ever about patents. Elon has famously open sourced all his Tesla patents, like such a bold thing to do and so gracious, I think, really to society. But his point is, oddly, I was talking to Ted Cruz about this, and he said, yeah, Elon thinks the same thing. He views the edge of competition as how fast you're moving, how great are your products. The consumers love them. Can I defend them in a court of law? And the protection that the drug guys get is so much. No one can really use software patents to get an algorithm or something. Like no one even tries.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  19. They cost you so high. They all cry. The VCs will tell you it'll never work. No one will have any incentive. If we don't have a 17-year protection, the entire Silicon Valley. I'm not saying. I've lived in a world where

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  20. And right now, there's a big fight over whether just their research papers have to go on non-private networks instead of the private ones they're on today. I mean, they just want the information out there. Like, that's a minor step. I would consider a major step. And you don't have to take the money. Why is the U.S. government giving people money that ends up becoming proprietary inventions? That makes no sense to me. Yeah

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  21. Here's an interesting thing the NIH gives out $40 billion a year, and a lot of that money goes to companies that end up getting venture capital back.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  22. Intellectual property is, I got to be a top 10,000% supporter of open source. And this gets back to Ridley's book, The Rational Optimist, but he talks about prosperity comes when ideas have sex and just the sharing of information in my mind should be free, that it shouldn't cost anything. And it's very unclear to me that the patent system actually adds value. I'm quite doubtful that the human mind wouldn't innovate if it didn't come with a 17-year financial protection. Like I just, I'm doubtful of that. There's great scientists at every university working on problems that aren't necessarily being patented. And your ability for hyper competition and innovation is so much higher when there aren't restrictions in place. I think the world's a better place when ideas are shared and not protected.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  23. We are seeing some. I think it could be pretty interesting and provocative. And could lead to positive change. I'd love to see I have this dream that some state and maybe this state that we're sitting in that has a surplus would do something crazy with teacher salaries. Like what if a state just all of a sudden said we're going to pay 50% more for teachers? Think about the dynamic that would create be pretty wild.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  24. But, you know, you see Newsom and Abbott, you know, fighting back and forth, and maybe there can be a positive outcome from this. And I think some of the federalist papers kind of envisioned that different states could try different experiments and we could see what happens as a result of that.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  25. I'm enamored by a state versus state competition. Part of it pops into my brain from the China experience and the provincial competition.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  26. Yes, yes, yes, yes. Our mutual friend, Rich Barton, talks about shining flashlights in dark places, this technology that we have access to. I think donation should be on the blockchain, quite frankly. Like there's no reason why this information needs to be in the dark. I think there's a lot of opportunity around data aggregation.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  27. They go around and meet with businesses that, because they're on that committee and have influence and they're raising money nationally. Like, I think that's ridiculous personally. And you could imagine restrictions against that, transparency towards it. Like if your congressman represents this zip code in Austin, wouldn't you want to know if they're raising money in Minnesota? Isn't that a little unusual?

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  28. Here in the U That would be the hope. And also, I think just shining a light on them. I'll give you an example that relates to regulatory capture. After you've been a senator or congressman for a while, you get invited on the committees. The minute you're on a committee, you are in charge of regulation that affects different industries. Well, what happens, I don't even know if most humans know this. What happens is your local senator or your local congressman who you think is representing your district now starts raising money nationally.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  29. And it identifies the best practices from the countries that have the best scores. That kind of thing, like investing in that type of data and transparency is pretty compelling to me. That's an example of what I might go do.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  30. Yes, yes, yes, but stablecoin may solve that. But this professor approached me about making a global database that scores countries on how captured they are.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  31. So there's a Nobel Prize winner from the University of Chicago named George Stigler. He's passed away, but who made the very strong argument that regulation is the friend of the incumbent, that large businesses learn how to lobby Washington. And no matter how well intentioned a policy is that's passed, it ends up benefiting the incumbent more than restricting the incumbent. And he won a Nobel Prize for that work. I gave a speech at the All-Nummit that you can go watch on YouTube as like 5 million views on this topic. But I think this happens in the majority of the time.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  32. Help shift these things. And I've already got to know some really innovative professors who are thinking and very innovative ways. And I look to use my financial capabilities to do grant writing through people like that and see what we can go do, see what we can go change. Regulatory captures, another one. That I've spent time tilting at.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  33. The past five years, as an example of what's possible with really great policy work. And it wasn't one person. I think, you know, the fact that Steve Pinker was banging the drum was super important, but Andreessen and Elon and all these people started pounding that same drum. Joe Gebby's wife made this like a big life passion project of hers. It's shocking how quick we went from this stuff's bad to, oh no, we made a mistake. It's actually good. And that could have a powerful impact on the planet. And so I don't know how many of those type things there are to find. I don't want to go grind on state-by-state legislation. I don't have any interest in that. But looking at big problems, looking at US-China relations, US healthcare system has some massive problems. Can you come up with ideas?

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  34. And so I found myself crossing them all off, and I couldn't discover something that got me excited and tied into this, what are you doing with your external learning thing? And slowly I've come around to an idea that I made up. So it's not a career that other people have. But I think I'd like to start a policy institute. I've come up with a name P3, which stands for purpose, progress, and prosperity. When I was doing the BG2 podcast, which I recently stepped away from, we did a episode at the Diablo Canyon Nuclear Facility. And before I did that episode, I spent three or four weeks calling everyone I knew to make sure that I was prepared for that. And that was one of our more successful episodes. And I just really enjoyed that. I look at the shifting mindset around the globe on nuclear energy.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  35. I just identified several people who had kind of successfully retired a strong word, but made a decision to stop doing a job they were very successful at. And then what do you do now? And it's similar to the Arthur Brooks book, but it was just a personal. And a lot of people ain't to invest, a lot of people go on boards. A lot of people manage their own money. I had this list and people teach and I slowly was checking them off like scratch them out. Yeah, like, man, don't really want to manage my own money. Don't really want angel invested. Don't want to start my own venture firm. I've done that.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  36. No. And as I mentioned when I made the decision to stop the venture career, which I think we talked about on the last podcast when I read the Steve Martin book, but I didn't know, I knew I wanted to do something else. And I went on a listening tour and I...

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  37. Because you've had two successful careers is not just a podcaster influencer, but as an angel investor, I would encourage you to read Arthur Brooks' book, Strength to Strength.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  38. And so he had the same thing. He's walking around Central Park. Should I stay in this incredible job at D.E. Shaw where he's making tons of money or should I take this flyer on this online bookstore I want to do? And he put it in his mind, that test, which is when I'm 80 and looking back, am I going to regret not doing this?

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  39. That night I made the decision that I got to go do something else. In Daniel Pink's book he talks a lot about boldness regrets, and this is where I say, do you want to do this the rest of your life? He says, one of the most robust findings in the academic research and my own is that over time we are as much more likely to regret the chances we didn't take than the chances we did. What haunts us is the inaction itself foregone opportunities all linger in the same way. And he says that they've studied this across China, Russia, Japan, common across all of them. And you may have heard of this YouTube video where Bezos talks about his regret minimization framework.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  40. It just stuck in my head. I went to the next one. Hopefully, I don't know who those people were, but I was like, no, I don't. Like that night.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  41. Yes, the thing that happened as a south side analysis, and this gets into, and I may partly this into something from the Daniel Pink book, but this notion of do you want to do this the rest of your life? The sell side job is wonderful. You get access so early in your life to so many amazing people, but you have to work really hard. And, you know, this classic thing where you're in your 20s and you're working on Wall Street, you know, they serve dinner at the office like cafeteria is open. That'll tell you something. And it was like 10.30 or 11 p.m. And the entire research department was on the 36th floor of Park Avenue Plaza. And I did a loop. The four corner offices were the most senior analysts. And for whatever reason, I popped my head in each of their office, and they were career cell site analysts. I said, do I want to be this person when I'm sixty?

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  42. I'm sure I've overplayed it in my brain, but they feel like very concrete moments where I had almost near certainty. The first one was I started my third project at Compact Computer Corporation where I was an engineer. And the projects were these computers we were releasing. And the third one was another computer with a little faster clock speed and a better Intel chip. But the rest of it was all the same. And we were going to do it again. And I'm like, that doesn't seem that interesting to me. And I'd become curious about other things. So when I was...

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  43. Valid motivator to get you to make good decisions. And there is A reality that that anxiety may feel may mean you're not in the right lane. And so when you were at that sales job, you got to the point where you're like, holy shit, I don't want to be doing this anymore. And I had two careers before I became a VC. One is an engineer and one as a sales site analyst. I enjoyed both. I think I was good at both, but I reached a point about three years in with each where I was like, I don't want to do this the rest of my life. And so I would say equally with like, don't give up too early, but if the signal is really telling you, I don't want to do this the rest of my life, jump out, that's the precise moment to move on and try something new. And I spend a ton of time in early chapters trying to get people to understand that's okay. Most people don't end up in a career that their major was. I think one of the reasons people

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  44. I'm sure it'll also give you five answers on how to deal with it. But by the way, one thing that's important when we're talking about this is Daniel Pink has this great book on regret and he talks about it as a

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  45. And so peers don't judge. That's why that trust thing really matters. Also, another reason why it matters. I think they can help you determine whether that is as big a blocker as it may seem like. But there's going to be some of that in any field. I don't think there's any run that's just without pain.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  46. Kind of at the end because I didn't want to leave people with the impression that it's just all smiles and babies and hugs. I don't think that's true in any field. And I guess my answer would be, you know, do you still feel this natural curiosity to learn the entire time? Is the impediment something that is truly means you should stop like I can't get around it Is it something that maybe can be avoided something I can get around I push heavily on the peer thing because one of the things a peer group can do is help you in those moments both just from emotional support but also to put perspective on whatever the speed bump is and whether it's insurmountable or not mentors can help with that too but I think peers are better for that because you were Worry about being judged in disclosing this.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  47. I wrote what I think most people would do, which is I just summarized the whole book and I submitted it to him and he said, no, this is no good. And so then I went to chat GPT research mode and I said, tell me about the 10 best nonfiction concluding chapters that you know of. And it went and did like a twenty page report and sent it to me. And what I noticed in reading that was that most of these great concluding chapters were orthogonal. They weren't a summary. They were kind of a different take on the whole thing. Well, my concluding chapter is now titled It Ain't Easy. To your point, and I went through all of the stories that we have in the book, and I pulled out the darkest hour moments for each one of those people and included it.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  48. It's funny. I'll take a short diversion in answering the question because people often ask me, you know, how do you use AI? When I was wrapping up the book, my publisher and editor said, you know, I want you to write the concluding chapter.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  49. Based on what you know of the two institutions. He ended up meeting Michael Lewis because he was in the Bay Area and some of the Stanford people knew Michael. And so he talked to the guy that wrote the book that inspired him. He hustled his ass off like, I don't want to make it sound like he kind of built his own curriculum, but it worked.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT

  50. Introduce you to these four people. And we're a lot like McConaughey's dad, you know, when Sam brought him that challenge.

    2025-12-17 · The Tim Ferriss Show · #840: Bill Gurley — Investing in The AI Era, 10 Days in China, and Important Life Lessons from Bob Dylan, Jerry Seinfeld, MrBeast, and More · IDENTIFIED FROM THE TRANSCRIPT