How to Live a Life You Won’t Regret at 80 - Bill Gurley

1. 0:00 – 4:44

   What Career Regret Really Means

   1. CWChris Williamson0:00

      What got you into thinking about the idea of career regret? As somebody that's had a very seemingly successful and fun career-

   2. BGBill Gurley0:07

      Yeah

   3. CWChris Williamson0:07

      ... why did you think about it?

   4. BGBill Gurley0:09

      I, um, I used to, I-- So I spent twenty-five years as a venture capitalist and the four years before that as a sell-side analyst on Wall Street. And through that process, I started writing as a way to differentiate myself. And so I was an early blogger. It was actually a fax, that's how old I am, um, when I started. And I got in the habit of when I had ideas, jotting them down and then, you know, either developing them. A lot of them ended up just undeveloped, but I would-- if I developed them, they would become a blog post. And there was a period in my career where I was reading a ton of biographies, and I finished this third one and saw a through line with these other two from people that were in wildly different fields, and I jotted those notes down. And that thing kinda simmered and breathed and, and took on a little bit of a life. And I got asked by the dean of the business school here in Austin at University of Texas to talk to the MBA class one day. And I was like, "Can I do this?" And he said, "Sure." So I pulled it out and developed it a little bit as a PowerPoint presentation. Um, anyway, they posted that on YouTube. A few people noticed. Some people that have been on your show, James Clear, noticed.

   5. CWChris Williamson1:23

      Mm-hmm.

   6. BGBill Gurley1:23

      And he posted it on his website, and people started prodding me to develop it as a book. And, um, a few years ago, I decided to s- begin retirement as a venture capitalist. It actually takes a while, unfortunately. And in that window, I thought about doing this. I thought about doing a book, and a lot of people wanted me to do a book. A lot of people wanted me to do a VC book or an investment book or a tell-all book on the Uber experience.

   7. CWChris Williamson1:49

      Mm.

   8. BGBill Gurley1:49

      And I was more drawn to this idea. Um, and a few other people prodded me who said, you know, like, "Go, go do..." And it felt more authentic. It felt like something that could have a bigger impact.

   9. CWChris Williamson2:01

      Mm.

   10. BGBill Gurley2:01

       And I was drawn to that. At this moment in my life, I was drawn to this particular thing. So I spent, like, six years, uh, working with a co-writer to-- and researcher developing, um, developing it further and making it this way. But y- you used the word regret. We did... Along the way, I launched a survey on SurveyMonkey that said, "If you could go back and start over, would you, would you do a different career?" And seven out of ten people said yes. And I eventually took that to Wharton People Analytics, and they did a more scientific version of it, much broader audience, and came back six out of ten.

   11. CWChris Williamson2:38

       Mm.

   12. BGBill Gurley2:38

       But very similar. Um, and that notion of career regret's int- interesting. I had the opportunity to talk to Daniel Pink, who you may know, who wrote a book-

   13. CWChris Williamson2:47

       He's been on the show about regret

   14. BGBill Gurley2:49

       ... about regret.

   15. CWChris Williamson2:49

       Yep.

   16. BGBill Gurley2:49

       And in that book, he says the biggest regrets people have, and, and, and he showed me a graph, it actually gets worse as you get older towards end of life, are regrets of inaction. He calls them boldness regrets. It's what you didn't do.

   17. CWChris Williamson3:05

       Mm-hmm.

   18. BGBill Gurley3:05

       Like, humans are great at forgiving themselves, made a mistake, learn from it, won't do it again.

   19. CWChris Williamson3:11

       Yep.

   20. BGBill Gurley3:11

       But they ruminate about what they didn't try. And so I, you know, I've, I've thought about this long and hard now since I've been working on it for six years. I fear our current education path has become a bit of a conveyor belt. People like th... You, you... We're pushing these children into this meat grinder and, um, and we're pushing them towards jobs that are c- you know, typically called safe jobs, at least before AI. And, um, I think they're learning to grind. That's what Angela Duckworth's been saying now. You know, the perseverance part, we've taught them, but if they don't have the love for it-

   21. CWChris Williamson3:51

       Mm

   22. BGBill Gurley3:51

       ... it turns into burnout. And so the purpose of this book that I wrote is hopefully to give as, as many people permission to go do what they want in life, you know? And, and look, it, it... I'm sure it won't touch everybody, but if there's a subgroup of people who read this and have the conviction that they can go succeed in this thing they love-

   23. CWChris Williamson4:14

       Mm

   24. BGBill Gurley4:15

       ... I think that'll be a huge impact on the world. Like, I think the people that do that are the people... Y- you know these people, like, that are just love what they do, and not only are they more successful, but I think they radiate a bit, you know, and spread positive energy.

   25. CWChris Williamson4:31

       Well, they're mimetic as well. They become a role model for other people-

   26. BGBill Gurley4:33

       That's right

   27. CWChris Williamson4:34

       ... to go and do. "Oh, I, he took a chance on that thing that he wanted to do, and wow, it didn't work out, and his life didn't blow up," or, "It did work out, and he's really happy."

   28. BGBill Gurley4:42

       That's right.

   29. CWChris Williamson4:43

       Um,

2. 4:44 – 9:41

   Why Humans Struggle With Uncertainty

   1. CWChris Williamson4:44

      thinking about the fact that we seem to regret inaction, boldness regret-

   2. BGBill Gurley4:49

      Yeah

   3. CWChris Williamson4:49

      ... have you reflected on why you think that is? What it is in the, the human mind that causes us to prefer dec- decisiveness over, uh-

   4. BGBill Gurley5:00

      I was hoping to bring up one of the many biases I've read about in all the behavioral science books, but I, I'm gonna go to a different place, which is I think we ruminate a lot. Like, like our brains, you know, constantly, eh, are, are replaying things in our minds.

   5. CWChris Williamson5:20

      Mm.

   6. BGBill Gurley5:20

      Um, and maybe that's what dreaming is too. But I think because of that, it's very easy to imagine these what-ifs, like it's-- to build a story, especially a positive story, around the what if I... that didn't get done. And then you compare that to your current life, and unfortunately, that can create anxiety, but I do think that might be part of it.

   7. CWChris Williamson5:41

      You'll be familiar with the Zeigarnik effect.

   8. BGBill Gurley5:43

      I'm not. Tell me.

   9. CWChris Williamson5:44

      Oh, cool. So, um, there was a psychologist who began studying waiting staff, and they realized that these waiting staff had unbelievable recall while the tables were still open. You know, you, you've ever been to a restaurant and you see some wait- waiter come up and they're stoodNo pen, no pad, no iPad-

   10. BGBill Gurley6:05

       I have seen that

   11. CWChris Williamson6:05

       ... hands behind their back. And they go, "This guy's crazy. Like, he's insane. I'm definitely gonna get something wrong."

   12. BGBill Gurley6:10

       Yeah.

   13. CWChris Williamson6:10

       And sometimes you might go, "I'm gonna... We'll take the sprouts, but I, uh, extra bacon, uh, no-

   14. BGBill Gurley6:16

       Right

   15. CWChris Williamson6:16

       ... no goat's cheese," but you wanna just see if, if, "All right, Mr. No, No, No Pad."

   16. BGBill Gurley6:21

       Yeah.

   17. CWChris Williamson6:22

       And, uh, the study ended up finding out, uh, the Zeigarnik effect, which is a- an open loop, closed loop bias that exists inside of the human mind. Um, while the tables were still open, the servers were able to recall what the orders were very closely. And as soon as they went, they... Nothing at all. You know a perfect example in almost everybody's life with this, I'm quite bad at this actually, but it, it still holds true. Hotel rooms. Let's say that you're moving from city to city to city. You're not bad at remembering the hotel room of where you are now.

   18. BGBill Gurley6:56

       Yeah.

   19. CWChris Williamson6:56

       But if I was to say, "Where did you s- which hotel room did you stay in two hotels ago?"

   20. BGBill Gurley6:59

       Yeah.

   21. CWChris Williamson7:00

       I, I'd give it 735. I don't know. I have no idea. Um, it's the same reason why cliffhangers work at the end of, uh, TV shows to get you to watch the next one.

   22. BGBill Gurley7:10

       Yes. Yeah.

   23. CWChris Williamson7:11

       The open loop. The, the human mind abhors an open loop.

   24. BGBill Gurley7:14

       Yeah.

   25. CWChris Williamson7:14

       And I get the sense that-

   26. BGBill Gurley7:17

       I see what you're saying

   27. CWChris Williamson7:18

       ... when it comes to boldness regret, the main thing that you have is an open loop.

   28. BGBill Gurley7:23

       Yeah.

   29. CWChris Williamson7:23

       Now, the human mind abhors open loops and uncertainty and ambiguity so much that we'd rather imagine a catastrophe than, uh, deal with the uncertainty. That's what a lot of anxiety, sort of future projected-

   30. BGBill Gurley7:37

       Yep
3. 9:41 – 15:05

   Why Do We Feel Obligated to Stick to the One Career Path?

   1. CWChris Williamson9:41

      When looking at the regret minimization framework, what are the things that... What are the common pitfalls that you've seen people do, even in, both inside of their career and outside of it? You must have reflected on this a lot.

   2. BGBill Gurley9:55

      Yeah, I have. One, one thing that I think, I, especially with, with the modern young people, I think one problem that I think exists, because we've built this, I call it in my book, a conveyor belt, uh, Jonathan Haidt called it a regret, or a, I'm sorry, a, uh, resume arms race. We've built this-

   3. CWChris Williamson10:13

      [laughs]

   4. BGBill Gurley10:14

      ... this, this pipeline for these kids that's so intense. I think when they get to their first job, they feel like it's the result of all this investment, and they feel like tweaking any way away from that is f- is, is throwing away the investment. Does that make sense?

   5. CWChris Williamson10:33

      Like a loss aversion type thing?

   6. BGBill Gurley10:35

      Yes. Yes. Yes. I invested all of this to get to this college to get to this degree.

   7. CWChris Williamson10:40

      Yep.

   8. BGBill Gurley10:40

      And if I move away from that, did I just waste all that time?

   9. CWChris Williamson10:44

      Mm-hmm.

   10. BGBill Gurley10:45

       And, um, you know, this is despite the fact that in, in-- There's a lot of, of studies that have been done, like f- and I won't get the numbers exactly right, but like five years after college, forty percent of people are no longer working in the field that was their major.

   11. CWChris Williamson11:01

       Mm.

   12. BGBill Gurley11:01

       And that number gets bigger at 10. But I... But it doesn't mean that they don't feel trapped, or that that number might not be higher if they didn't feel trapped.

   13. CWChris Williamson11:10

       Mm.

   14. BGBill Gurley11:11

       And when I mention this to young people, the- there, there is this weight. There is this weight they feel.

   15. CWChris Williamson11:17

       Mm.

   16. BGBill Gurley11:18

       Like an obligation to, to e- especially maybe they didn't pay-

   17. CWChris Williamson11:21

       Decisions that they locked in when they were 17.

   18. BGBill Gurley11:23

       Yes. Well, and that's another thing. In... When, when, when I was younger, [chuckles] the colleges wouldn't let you declare a major until the end of your sophomore year. Many schools, you have to apply to the major now. So we've moved the decision of what major are you gonna pick from the end of your sophomore year to the end of your junior year in high school.

   19. CWChris Williamson11:44

       Mm.

   20. BGBill Gurley11:45

       Like that's, you know, three years forward and less time to... There's a lot of people, um, a lot of smart people that just say we, we don't allow children enough time to explore.

   21. CWChris Williamson11:58

       Yep.

   22. BGBill Gurley11:58

       And, you know, Haidt says it. He has a chapter called Let Them... or The Loss of Play or something. Um, Rick Rubin's been pounding on this. He talks about it in his-

   23. CWChris Williamson12:09

       We looked at Jean Twenge's work, Generations.

   24. BGBill Gurley12:12

       Does... Is that another one?

   25. CWChris Williamson12:13

       Yeah. So G- Generations is, is really fascinating. This stinks of you. Highly recommend that you read it.

   26. BGBill Gurley12:18

       Okay, I will. I will.

   27. CWChris Williamson12:19

       Um, and-She talks about extended adolescence-

   28. BGBill Gurley12:23

       Yeah

   29. CWChris Williamson12:23

       ... sort of twins with sort of height stuff. We've got a real interesting duality going on, which is in one world you've got these kids that are sort of being forced to become adults more quickly-

   30. BGBill Gurley12:34

       Yes
4. 15:05 – 23:04

   Is Life Really “Use It or Lose It”?

   1. CWChris Williamson15:05

      You've got this line, "Life is a use it or lose it proposition."

   2. BGBill Gurley15:08

      Yeah.

   3. CWChris Williamson15:09

      What's that mean?

   4. BGBill Gurley15:10

      Well, I mean, it's tied to the, the, the, the boldness regret, right? Like you're gonna get to the end and, and then it's done. And, and only if you think in the way that Bezos did, um, with his regret minimisation framework, are you going to hold yourself accountable, um, for that line, you know? The, the, the recognition that, that life moves much faster than any of us realize, and then it's done. And, and, and you can get locked in even sooner. If you spend up to your limits, you can, you can, you can freeze yourself in a job like that you can't leave.

   5. CWChris Williamson15:48

      Mm.

   6. BGBill Gurley15:48

      And you can do it with personal commitments as well. I-- my, my second [chuckles] career was, you know, going to Wall Street, and I can't tell you the number of people I worked in with Wall Street that had, for their age, ridiculously high salaries, but they had the place in the Hamptons, the summer lease. Like they tried to get into the membership club. Like they spent right up to the limit.

   7. CWChris Williamson16:11

      Mm-hmm.

   8. BGBill Gurley16:11

      And now you can't switch, you know? You can't switch.

   9. CWChris Williamson16:15

      Yeah. You're locked in at this very high burn rate, which means-

   10. BGBill Gurley16:17

       Yes

   11. CWChris Williamson16:17

       ... you need to keep pouring fuel in the top of it.

   12. BGBill Gurley16:19

       Yes. Yes. I, I have-- Like for young adults that are lucky enough to have a job with a decent salary, I would heavily encourage them not to spend against it just so they can have the flexibility to do other things, move cities, change jobs-

   13. CWChris Williamson16:36

       Mm

   14. BGBill Gurley16:36

       ... um, all of which may be the right path for them.

   15. CWChris Williamson16:38

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   16. BGBill Gurley17:49

       [laughing]

   17. CWChris Williamson17:50

       It's n- And even flexibility is only show-off-able insomuch as you can take a photo of you on a plane or you at a holiday, or you at a... Which again, is, uh, not quite the flexibility that we're-

   18. BGBill Gurley18:03

       I understand exactly what you're saying

   19. CWChris Williamson18:03

       ... that we're talking about here.

   20. BGBill Gurley18:04

       Yeah. Yeah.

   21. CWChris Williamson18:05

       So, um, I, I've always thought about this, the difference between hidden and observable metrics.

   22. BGBill Gurley18:11

       Yeah.

   23. CWChris Williamson18:11

       We'll often trade a hidden metric for an observable one.

   24. BGBill Gurley18:15

       Sure.

   25. CWChris Williamson18:15

       You know, trade the quality of our sleep for a slightly bigger pay packet. We'll trade the hours of, uh, peace that we have on a Saturday-

   26. BGBill Gurley18:24

       Yeah

   27. CWChris Williamson18:24

       ... for a position, uh, improvement. We'll trade... God, I mean, you know, to s-s-some people will trade a caring, supportive wife for a very difficult, younger, hot one.

   28. BGBill Gurley18:35

       [chuckles]

   29. CWChris Williamson18:35

       Um, you know, the, the, the trades are everywhere.

   30. BGBill Gurley18:37

       Yes. I, I think that's a good framing.
5. 23:04 – 30:14

   Why Some of Us Successfully Pivot and Others Don’t

   1. CWChris Williamson23:04

      so I guess one of the situations that so many people must be in is someone... One version of them successfully pivots, and another version of them stays stuck for life.

   2. BGBill Gurley23:17

      Yeah.

   3. CWChris Williamson23:18

      Why do some people successfully pivot and, and, and others end up getting stuck?

   4. BGBill Gurley23:25

      Well, I mean, there's a, there's a... You could come up with a number of things. One of them is financial, which we've, we talked about. You could be overspending. There's a, there's a different case where you're just, you're, you're stuck financially, like you need... You're living hand-to-mouth.

   5. CWChris Williamson23:37

      Mm-hmm.

   6. BGBill Gurley23:38

      Um, there's a... I have a, I have a profile in the book of Jen Atkin, who I don't know if you know who she is. She's probably the mo-most successful hairstylist of all time. Like, went-- not only achieved, touched the top rail of that, but then launched beauty products, sold that company. But she moved to LA with $300 in her pocket, and that's not to say anyone can do that. But, like, there, there are stories of people with near nothing starting on the very bottom rung and finding their way to be successful. There's this classic meme of starting in the mailroom in Hollywood, and David Geffen and, and Barry Diller and all these people started in the mailroom, you know? It's the, it's about as low a rung as you have in that business.

   7. CWChris Williamson24:21

      Mm-hmm. Mm-hmm.

   8. BGBill Gurley24:22

      So I, I think it's possible. But you may feel stuck financially. You may feel that you can't get there. Um, and then the other one, you know, it, it, it could be, like, this perception. McConaughey had this perception that his father wanted him to be a lawyer. It's probably just that Matthew had told him he was gonna be a lawyer, and he was supporting that. But, but that weight can be there too. Like, you may feel... I, I think there are certain, um-There are certain, uh, cultures where, where like being a doctor is considered really high. In Russia, like being an academic was con-- So you may, you may feel pressure from your family as this is the thing people in my family do.

   9. CWChris Williamson25:03

      Mm.

   10. BGBill Gurley25:03

       And I've seen that, and I've met people who have that weight upon them. Those are all kinda things that could restrict this movement.

   11. CWChris Williamson25:11

       What about the fear? Uh, there, there has to be a huge chunk of people that just... I, I, w-what if this doesn't work? It's sort of ambient-

   12. BGBill Gurley25:19

       Yeah

   13. CWChris Williamson25:19

       ... ephemeral, v-v-this fugue fog thing that's come down on the-

   14. BGBill Gurley25:25

       Well, well, if you, if you allow me like to give you a little history of how, um, or why I would say I spent, I spent six years turning the, uh, the original presentation into a book, and I, I, I had this thing I really wanted to achieve, which was to embed as much stories and narrative into it as possible.

   15. CWChris Williamson25:43

       Mm-hmm.

   16. BGBill Gurley25:44

       And, um, I was listening... I know you've had Morgan, uh, Housel on.

   17. CWChris Williamson25:48

       He's the GOAT. He's the absolute GOAT.

   18. BGBill Gurley25:50

       And he was on, um, he was on a podcast called "Why We Write," talking about-

   19. CWChris Williamson25:55

       David Perell

   20. BGBill Gurley25:56

       ... the power of, of narrative.

   21. CWChris Williamson25:58

       Yes.

   22. BGBill Gurley25:58

       And so the book is divided... It, it's structured unlike most books. It's divided into two parts, but they interleave. And so every other chapter is a Atlantic-sized article about someone that started on the bottom rung with intention and made it to the top. And the reason I wanted to include those is precisely for the reason Morgan talks about, which is, I think these things stick in your brain more. Like, a lot of the books in the category that have done extremely well in career, um, read like a textbook. Do a, do A, then do B, then do C. But they don't, they don't have this kinda spirituality to them that I think can infect the brain a little bit more. [chuckles] Does that make sense?

   23. CWChris Williamson26:42

       It's 100% correct. I mean, Ben Shapiro's favor- famous line of, "Facts don't care about your feelings," is as backward as it could be, that feelings don't give a single fuck about the facts.

   24. BGBill Gurley26:53

       Yeah, so we have eight, nine or ten, I, I should know the exact number, but I can't recall right now, of these profiles, and I alternate them with the principles. And it's... I always thought about it like candy and vegetables, you know, or something. But you get, you get some of both and, uh-

   25. CWChris Williamson27:08

       It brings the ideas to life.

   26. BGBill Gurley27:10

       Yes. And I think the, the reason I told that long story was in answer to your question about fear. I think seeing this many stories, and they're all... I-- By the way, I chose every one of them from a field that your parents would probably tell you not to go into. I intentionally skipped, you know, investment bankers and, and-

   27. CWChris Williamson27:31

       Doctors

   28. BGBill Gurley27:32

       ... yeah, all the stuff that everyone knows is, is-

   29. CWChris Williamson27:35

       Nice linear progression.

   30. BGBill Gurley27:36

       Yes. I got... I, I, I have none of those in there-
6. 30:14 – 38:42

   The Real Risk of Starting Over in Your 30s

   1. CWChris Williamson30:14

      Uh, w- So talk to me about the risk of starting over in your 30s or 40s.

   2. BGBill Gurley30:20

      Yeah.

   3. CWChris Williamson30:20

      You know, the idea of not just w-what am I gonna do, but I, you know, I should've had my life together by now. Is it really? You're telling me I'm gonna start again at 37? I'm gonna, uh, be at the bottom of the pile, and I've got all this sunk cost fallacy from before.What are people gonna think of me?

   4. BGBill Gurley30:38

      Yeah.

   5. CWChris Williamson30:38

      What, what's the real risk of starting again in thirties and forties?

   6. BGBill Gurley30:40

      Well, one-- I mean, one thing I would encourage you to do, there was a, there was a, this book I read when I was really in, I think back in business school, called Shark Proof by Harvey Mackay. He wrote... He's known for his sales book, but he wrote a book about careers, and he said to keep your dream job. He-- this was an older book, so he said keep it in a manila folder in a file, but you could create it in a Google Doc or something.

   7. CWChris Williamson31:02

      Yeah.

   8. BGBill Gurley31:02

      That, uh, where you're just keeping notes. Like, well, if I do it one day, you know, and, and, and everything you learn, people you might talk to, I think you just pi-pile more and more stuff in there, and it'll start to feel more real. Like you can, you can begin the process before you make the leap.

   9. CWChris Williamson31:20

      Mm-hmm.

   10. BGBill Gurley31:20

       Right? And then the, the, the second thing, I'm gonna say three things. The second thing I would say is if you have some curiosity that's occupying your downtime, that's a really interesting tell.

   11. CWChris Williamson31:35

       Mm.

   12. BGBill Gurley31:35

       You know, when I was an engineer, I, I got a computer engineering degree and I was working at Compaq Computers in Houston. That was a big hot company back in the day. And I was going home at night and I had started-- I'd learned about stocks and I was trading stocks. You know, I'd read One Up on Wall Street. I had this, uh, I forget what it was called, this book. You just get this book with all these one-pagers on every stock. Like I was... Uh, that's what I was doing in my spare time. So if you're doing something like that in your spare time, like it's calling you, you know?

   13. CWChris Williamson32:08

       Right.

   14. BGBill Gurley32:08

       And then the, the third thing, there's a chapter in the book actually titled "Never Too Late," and we list about twenty people that did post forty pivots, and we go deep on four of them. Uh, my favorite being local Austinite, Burt Beveridge. Um, Burt's, uh, nickname is Tito, so that'll, that'll tell you who he is. But, um, seismology degree undergrad, worked in oil and gas for, for several years. Um, ended up down in South America where he got frightened by a few experiences. Um, so he, he hung that up out of fear a-and the boom bust cycle. Became a mortgage broker. Um, didn't really love it, you know. Not sure he equated his identity to being a mortgage broker. And, um, one night, [chuckles] this is such a... Like, uh, it's part of why I love, like, self-help books and ideas so much. He's watching a PBS special that says, "Take out a sheet of paper, draw a line down it, put the stuff you love to do on the left side and the stuff you're good at on the right, and see if you can find a through line." And he's looking at this sheet of paper and realizes he wants to start a spirit company. He's got like chemistry on the right.

   15. CWChris Williamson33:22

       Mm.

   16. BGBill Gurley33:22

       He's like hanging out at bars on the left, [chuckles] like, and, and, um, he didn't know jack shit about launching a spirit company. And it turns out Texas is probably the worst place you'd ever... At the time, there was no one that had a license for a spirit company in Texas. Um, but of course, Tito's is now the most bestselling spirit in North America. He, uh, owns a hundred percent of it himself.

   17. CWChris Williamson33:48

       No way.

   18. BGBill Gurley33:49

       Yes.

   19. CWChris Williamson33:49

       The whole thing's bootstrapped?

   20. BGBill Gurley33:50

       Yes.

   21. CWChris Williamson33:51

       Oh.

   22. BGBill Gurley33:51

       Credit card. Yeah, nineteen credit cards.

   23. CWChris Williamson33:54

       Fucking hell.

   24. BGBill Gurley33:55

       But it's such a great story. Like, it's just such a great story.

   25. CWChris Williamson33:58

       [laughing]

   26. BGBill Gurley33:59

       And, and, and, and, and, and now, you know, he's at the phase in his life where he's giving back and launching foundations and this is my point. Like say I had a c- I had a young person at John Hopkins raise their hand and say, "But I, I don't wanna chase my passion. I wanna be purpose driven." And I s- I thought to myself, you know, every profile in the book, these people are touching more lives than they could have ever imagined. Like-

   27. CWChris Williamson34:23

       I don't want to chase my passion. I want to be purpose driven.

   28. BGBill Gurley34:27

       I think it's part of a new movement to just like, feel good about yourself. Like, I'm a, I'm... My, my main goal in life is to help other people.

   29. CWChris Williamson34:36

       Serve.

   30. BGBill Gurley34:36

       Yeah.
7. 38:42 – 41:54

   The Tricky Relationship Between Discipline, Motivation and Obsession

   1. CWChris Williamson38:42

      Joe Hudson's got this line, "Enjoyment is efficiency," he says. And I, I think-

   2. BGBill Gurley38:47

      I liked it.

   3. CWChris Williamson38:48

      I think it's really, really true. Yeah. That people-

   4. BGBill Gurley38:52

      It ki- yeah.

   5. CWChris Williamson38:53

      People have this relationship between discipline, motivation, and obsession. Discipline's always there, but it-- there's a lot of friction. Motivation, the friction gets removed a little bit, but it, it, it's, it's sort of harder to, to grab a hold of. You don't really know where it comes from. Maybe it's a rock playlist or maybe-

   6. BGBill Gurley39:07

      Right

   7. CWChris Williamson39:07

      ...it's the right amount of caffeine or something. Uh, and obsession is friction inverted, as opposed to you having to push through resistance. The resistance pulls you toward it.

   8. BGBill Gurley39:16

      That's exactly right.

   9. CWChris Williamson39:17

      And the problem I think, or the reason that obsession is difficult is that obviously if it's pointed in a non-positive direction, that's how you become obsessed with politics or porn or your toxic ex or something.

   10. BGBill Gurley39:31

       Yeah.

   11. CWChris Williamson39:31

       Um, but if it's pointed in the right direction, what from the outside looks like a superhuman amount of discipline, from the inside feels almost like you haven't chosen it. You, you, you, you're n-not... I'm not, I'm not choosing to do this thing. You know, I, I mentioned before we got started, there's not been a single house I've lived in for a decade that I've not turned one of the bedrooms, including most of the ones that I slept in, into a podcast studio-

   12. BGBill Gurley39:54

       [laughs]

   13. CWChris Williamson39:54

       ...for a decade. My house back in the UK has got a podcast studio in it. The one that I live in right now is still podcasting. Eight years in, a thousand episodes. Every single house has had one. Every Airbnb that I've stayed in, I get there and I... Fuck. I'm l- researching hotels to see if the depth of the table-

   14. BGBill Gurley40:10

       [laughs]

   15. CWChris Williamson40:11

       ...can withstand my MacBook, the stand, and the, and the-

   16. BGBill Gurley40:14

       Yeah

   17. CWChris Williamson40:14

       ...fucking tripod because that's what I want to do.

   18. BGBill Gurley40:17

       Yeah.

   19. CWChris Williamson40:17

       That's what I want to do. I want to have these conversations. So okay, I, I, I, I... My entire life gets warped around it. I'm sure you'd be familiar with the, uh, single ordinating principle. I think Bezos has got one and I think Musk's got one, and Bezos's was always, "Does this make the customer experience better?"

   20. BGBill Gurley40:33

       Yeah.

   21. CWChris Williamson40:33

       So everything, every single decision in Amazon-

   22. BGBill Gurley40:36

       Yeah

   23. CWChris Williamson40:36

       ...was threaded through this sort of single eye needle. And, uh, Musk's is, "Does this get us closer to Mars? Does this get us closer?"

   24. BGBill Gurley40:46

       And by the way, both of those people did something that is super extraordinary, which is they took an innovative company, grew it to hundreds of thousands of employees, and kept it innovative. It's, it's two of the only examples I know of.

   25. CWChris Williamson41:03

       They didn't get laden down with diseconomies of communication, uh-

   26. BGBill Gurley41:07

       Right. The bureaucracy

   27. CWChris Williamson41:07

       ...lumbering fucking behemoth bullshit.

   28. BGBill Gurley41:09

       Bureaucracy that always lands in big companies, and it must be some heuristic, like the one you described, that allows them... In fact, I, I was just listening to Elon on, on Cheeky Pine, I think.

   29. CWChris Williamson41:23

       With Dwarkesh. Yeah, yeah.

   30. BGBill Gurley41:24

       Yeah, this came up. This came up. Like, like, every leader wants to know how he does it. That's why I think Collison was asking him, like, "How do you lead?" He, he goes, "Well, I'm, I'm down deep and..." "You can't be deep. There's, there's two hundred thousand employees." And Elon jokes, "Yeah, there's two hundred thousand employees." Like, you have to have some heuristic, simplifying heuristic-
8. 41:54 – 48:30

   The Clear Signs It’s Time to Change Your Career Path

   1. CWChris Williamson41:55

      Okay, so career pivot fear.

   2. BGBill Gurley41:57

      Yes.

   3. CWChris Williamson41:58

      Someone is in their career. Uh, not super fired up. Or, "I, I used to be, and it just feels like it's time for me to grow now." What are the indicators that it's time to move, and what are the, um, things that they should keep in mind to, uh, maximize their bravery? Give them a little exogenous amount of morale.

   4. BGBill Gurley42:22

      Ooh. So, so on the, on the, um, do you know... I mean, I love, I love this test of is, do you see yourself doing this thirty years from now?

   5. CWChris Williamson42:31

      Mm-hmm.

   6. BGBill Gurley42:31

      'Cause if the answer to that is no, you should get busy. What's the line from Shawshank? Like, get busy living or get busy dying. Like, if you know that's true-Like, well now is when you should start. I'm not saying ju- like quit tomorrow, but like start building the plan. Like, and then there's all kind of things you can do. Um, um, in Designing Your Life, uh, Dave Evans says-- has this exercise where he says, "Create three to five scenarios and battle card them of what you might do next." Like, you know, fill them out. AI can really help, right? Like, like you could build a 20-pager on each one of these career paths. What might I like? What might I not like? What, what are the three things people love in this career? What are the three things... You can steer it at all, right? You can ask people in those fields. You can go find them. So you could, you could role-play being in each of these. There's a, there's a, there's a heuristic in the book that I borrowed from, from Ben Gilbert at Acquired, [chuckles] a lot of podcasters, um, where he had side hustles at all his jobs. So at each job he went to, he would ask the employer, "If I do it on my own time, can I do this other thing also?" And what's-- Th-there's something really great about that. One, in each of his cases, he ended up doing something pretty remarkable in the side hustle. At Microsoft, he created Microsoft Garage, which became this way for Microsoft to stay relevant with founders, and he met all these founders. Like, all this kind of extra goodies came from that. Um, but I think it all... Like, so you learn more. You learn maybe two... You get two shots on goal instead of one, and I think the employer makes you look proactive.

   7. CWChris Williamson44:10

      Mm-hmm.

   8. BGBill Gurley44:10

      So it reflects positively on you.

   9. CWChris Williamson44:12

      Mm-hmm. Mm-hmm.

   10. BGBill Gurley44:12

       When he ended up at, at Madrona VC, asked him if he could start a podcast, and look where that led. [chuckles] And, um, I just had dinner with both of them, and, uh, they were in Austin. And man, they're happy. Like, [chuckles] I gotta tell you, like they are really happy people. So similar to, to you and, and, uh, your obsession. And, and they fell into it through that, through getting there through that way. So I think those are some things you can do to, uh, to test. And then look, what are you doing in your spare time? Like, are there any signals there?

   11. CWChris Williamson44:46

       Mm-hmm.

   12. BGBill Gurley44:46

       Um, those are all great ways. I wouldn't quit if you don't know where you're going. That doesn't make any sense.

   13. CWChris Williamson44:51

       Yeah. Yeah. Uh, it, it, it's such a good shout to say, so what are you thinking about in the shower?

   14. BGBill Gurley44:57

       Yes.

   15. CWChris Williamson44:57

       What are you doing in your spare time? I keep on fucking watching pickleball drills. I just keep on thinking about pickleball, and I, I'm really interested in the sport, and I'm interested in how it's growing, and I love playing it with my friends. But even when I'm not playing it, I'm always thinking about it a lot.

   16. BGBill Gurley45:12

       Let, let me, let me-

   17. CWChris Williamson45:13

       Okay, maybe there's a... you know, maybe there's something going on there.

   18. BGBill Gurley45:15

       Let me share this fun story I just stumbled on, 'cause I was, I was... I'm, I'm, I'm using some hacker techniques to promote the book, and, and that led me to talk to this gentleman. And, uh, [chuckles] I-- when I pinged him, he said, he said, "Oh, I... You please send me the book." He goes, "I saw the video a long time ago, and it changed my life." And I said, "Well, tell me that story." And, um, he was, he was a real estate lawyer, and he loved football, and he loved offensive plays and offensive diagrams in football.

   19. CWChris Williamson45:47

       Mm. Mm.

   20. BGBill Gurley45:48

       [chuckles] I love this story 'cause it fits with my thesis that the best stories are in jobs your parents would tell you to never go do. He launches a website to help people, like manage and develop football plays, and then he builds software, and then he starts a podcast. He has nine hundred thousand followers, and this is what he does all day now. He talks about offensive football plays with the best and the brightest in the field. He's known throughout the industry. What a great story. Like, how awesome is that?

   21. CWChris Williamson46:19

       That's brilliant.

   22. BGBill Gurley46:19

       [chuckles] It's so great. Like, like I think people don't realize that you can actually... There, there are careers in a lot of places. A lot of people, um, want to be in Hollywood or music, and they think they can't do it 'cause they're not talented. But there's a hundred support jobs for every artist that's out there.

   23. CWChris Williamson46:40

       Mm.

   24. BGBill Gurley46:40

       And there's tons of work to go do. You know, if you really love being around that stuff, there's tons of opportunity.

   25. CWChris Williamson46:47

       Especially given that you can fail at a job that you hate. You can, you can underperform in a industry that you don't want to be in.

   26. BGBill Gurley46:56

       Yeah.

   27. CWChris Williamson46:56

       So the prospect of potentially doing okay at one that you love i- is infinitely better.

   28. BGBill Gurley47:02

       I think so. I think so. That goes back to life is a use it or lose it proposition. [chuckles]

   29. CWChris Williamson47:08

       Mm.

   30. BGBill Gurley47:08

       Like, give it a go. And then the other thing to know about failing in that is, uh, humans are... Like, the s-- the, the research in psychology says humans are really good at forgiving themselves. Like, you're not... The failure's not gonna... You're not gonna ruminate on it forever.
9. 48:30 – 50:12

   Plateau or Boredom: How to Tell the Difference

   1. BGBill Gurley48:30

      sentiment.

   2. CWChris Williamson48:31

      So you quit a successful job at Compaq-

   3. BGBill Gurley48:33

      Yep

   4. CWChris Williamson48:34

      ... to start again.

   5. BGBill Gurley48:35

      Yep.

   6. CWChris Williamson48:36

      How do people know when they're plateauing versus they're just a bit bored or something?

   7. BGBill Gurley48:43

      Yeah.Um, I-- a few people have asked me this question. I, I o-once again, I think the thirty-year forward exercise gets you away from that because it's, it's, it's asking a different question. Um, o-one, one thing I'm really big on is, um, a-and there's a, there's a different chapter dedicated to this, is, is developing peer relationships.

   8. CWChris Williamson49:07

      Mm.

   9. BGBill Gurley49:08

      And we can go into why I think that's such a huge unlock. But, but one of the benefits of having a group of peers, especially if they're outside your organization. So these are people on the same career path you're on, but are maybe a, a bit distant. They're at a different company or whatever.

   10. CWChris Williamson49:25

       Mm.

   11. BGBill Gurley49:26

       And if you have a community like that, that you really trust and support one another, they can help you with that question you just asked. Like, am I, am I failing and I'm never gonna succeed because I don't have the right talent for it? Am I-- do I maybe have a shitty boss? Is their experience different?

   12. CWChris Williamson49:43

       Mm.

   13. BGBill Gurley49:44

       Like, like you can... It's a great group of people to ask those questions of.

   14. CWChris Williamson49:48

       It's almost like being able to run a little split test of yourself.

   15. BGBill Gurley49:52

       Yes.

   16. CWChris Williamson49:53

       What are the things that are different in your experience, and how much of those are fundamental to-

   17. BGBill Gurley50:00

       The role.

   18. CWChris Williamson50:00

       Exactly.

   19. BGBill Gurley50:01

       Yeah.

   20. CWChris Williamson50:01

       And how much of that is transient that I could just-

   21. BGBill Gurley50:03

       Absolutely. Absolutely

   22. CWChris Williamson50:05

       ... finesse my way out of.

   23. BGBill Gurley50:06

       There's ten other reasons why you should build that group, but that's-- it's, it's good at helping with that problem that you just described.

10. 50:12 – 54:49

    Can You Upgrade Your Circle and Stay Genuine?

    1. CWChris Williamson50:12

       How do you deliberately upgrade your peer group without it being transactional? How can you make like-minded friends and peers without them thinking that you're constantly just wanting something?

    2. BGBill Gurley50:26

       Yeah. It's a tough question because I think the number one reason people are bad at, at forming these peer groups is they've been taught to be a climber, and they've been taught to-- almost been taught to be a bit sharp-elbowed and to outgun the next person.

    3. CWChris Williamson50:42

       Zero-summing.

    4. BGBill Gurley50:43

       Yeah. And, and we borrow a lot of our mental frameworks from f-from finite games that have a beginning and an end and a single winner. And careers just aren't that way. Almost any industry, if it's not, uh, downhill skiing, there's lots of winners. You know? There's tons of winners. Um, podcasting is a great example of that.

    5. CWChris Williamson51:03

       Mm.

    6. BGBill Gurley51:03

       There's tons of winners in Austin.

    7. CWChris Williamson51:05

       Mm-hmm.

    8. BGBill Gurley51:05

       Um, and so if you can build a peer network of like-minded people that you trust... And, and, and the g- the great test of, do you trust, would you share your best ideas with them? Like, that you've learned this new thing that you just unlocked in your job, would you share it with them? You should, actually, I believe. But a lot of people wouldn't. And so if you, if you-- once you get to that place, uh, it's a really special place. Um, there's a, there's a story in the book about Chris Del Conte, who's the athletic director here at the University of Texas. And when he broke into sports administration, he was in the development office. He went to a conference, like... And it-it's a great place to meet peers. He went to a conference and met with a couple of other young men who were also at the beginning of their career. They exchanged numbers and started a text group. And over time, they added a few more people to that. Got up to, like, seven. Seven or eight. They're all eight-- all eight of them are D1 athletic directors now, and they all started on the bottom.

    9. CWChris Williamson52:11

       Wow.

    10. BGBill Gurley52:11

        And if you s- follow them along that journey, their learning elevated each time. The-- each year they met, each, each time they texted, the problems they were encountering, they were sharing, they were explaining. It got to the point where they would do weekends away with their wives and invite in guests. You know, you talk about external learning. Who, who's holding mini conferences on their own nickel and bringing, and bringing in external guests to help educate them so that they could rise and thrive together?

    11. CWChris Williamson52:44

        Mm.

    12. BGBill Gurley52:45

        Uh, it's just so... I, I just, like, I get, like... There's another story that's, that's p-perhaps more modern for [chuckles] the younger crowd. MrBeast did this when he was seventeen. He found three other people that were trying to hack YouTube. They were basically trying to figure out the game of YouTube, and they were on a Skype call for sixteen hours a day together. And he says if there were a fifth person in that room, they would have made a million dollars also.

    13. CWChris Williamson53:11

        Mm.

    14. BGBill Gurley53:11

        Like, it was just because the stuff they were uncovering-

    15. CWChris Williamson53:14

        Mm-hmm

    16. BGBill Gurley53:14

        ... was so usable and just deterministic, just no one else knew it. And he used a phrase I love. He said, "You know how they talk about ten thousand hours?" Referring to the Malcolm Gladwell book. He says, "We got forty thousand hours 'cause we were, we were sharing it all." It's not the exact math, but it's a, it's a, it's a cool reflection of the moment, you know?

    17. CWChris Williamson53:37

        A quick aside. You've probably heard experts like Dr. Rhonda Patrick talk about the benefits of omega-3s. They reduce... Hello. Omega-3s. There they are. They reduce brain function. [chuckles] No, they don't. They support brain function. Maybe I should take more. They support brain function, reduce inflammation, improve heart health, and are backed by hundreds of studies. But here's the thing: all omega-3s are not made the same. Most brands cut corners. They use cheap fish oil, skip purity testing, throw in fillers, and call it a day. But with Momentous, you know you're getting the highest quality omega-3s on the market. They're NSF certified for sport, and they're tested for heavy metals and purity. So you can rest easy knowing anything that you take from Momentous is unparalleled when it comes to rigorous third-party testing. What you read on the label is what's in the product and absolutely nothing else. Best of all, Momentous offers a thirty-day money-back guarantee, so you can buy it and try it for twenty-nine days. And if you don't love it, they'll just give you your money back. Plus, they ship internationally. Right now, you can get thirty-five percent off your first subscription and that thirty-day money-back guarantee by going to the link in the description below or heading to livemomentous.com/modernwisdom and using the code MODERNWISDOM at checkout. That's L-I-V-E-M-O-M-E-N-T-O-U-S.com/modernwisdom and MODERNWISDOM at checkout.What

11. 54:49 – 1:00:53

    Do Mentors Actually Matter?

    1. CWChris Williamson54:50

       do you think about mentors? You know, peers are great. They're struggling with the same challenges you're sharing and sort of going on the journey together. That feels cool. It's like a teammate. But presumably there's a, a good argument to be made. Well, maybe you aim for someone that's already been through the pitfalls.

    2. BGBill Gurley55:06

       Yeah.

    3. CWChris Williamson55:07

       How do you come to think about the role of mentors?

    4. BGBill Gurley55:08

       I think you do both. I think you do both. They serve very different purposes. The, the co-learning journey, uh, I mean, peers give you, give you co-learning. They give you support, which I talked about. They give you reflections to... You can ask those questions, "Is this the same in your job?" Um, um, you're vulnerable with peers. You wouldn't do that with a mentor, right? Like, e-especially if you get the peer group in the right place. You, you tell them, "I'm struggling here." Like, um, so I think it, I think it's just a different purpose. Um, with-- I think mentors are extremely important, but I think the idyllic version of a mentor is a bit broken because we encourage a lot of young people to cold call too high, where the rejection rate's gonna be 98%.

    5. CWChris Williamson55:54

       Because the CFO of this company doesn't want to be friends with you.

    6. BGBill Gurley55:57

       [chuckles] Yeah, exactly.

    7. CWChris Williamson55:58

       Yeah.

    8. BGBill Gurley55:59

       But it happens constantly. And so what I encourage people to do is divide mentorship into two different categories. Have aspirational mentors, and just like that file folder for your dream job, create one for each of them. Like, study them like a kid might study Star Wars characters or something. You know what I'm saying? Like-

    9. CWChris Williamson56:20

       Mm

    10. BGBill Gurley56:21

        ... really get enamored with these people that you, you idolize as aspirational mentors. And one, you're gonna learn a lot studying them. And by the way, the resources are amazing right now. YouTube interviews, podcasts, like AI. You, you can learn faster than you ever could have learned before. So study them. If you ever meet them one day, the fact that you studied them this long is gonna prove super useful. And then for the mentors you actually want guidance from, like, tone it down a bit. Like, go two levels below what you thought you were supposed to do, and you're gonna meet somebody who's so thrilled that you recognize that they were successful and worthy of giving advice that your hit rate is gonna go up 10X or more. Like, the probability that you're gonna get them to do the work is so much better. Like-

    11. CWChris Williamson57:16

        I noticed that when I first started the show in 2018, and still not early, it felt late, but, you, you know, now it feels early-ish. It was so flattering for people to be invited on a podcast. You know, one of the other things, s-such a funny trick that I still use now, so the world can have this one. Uh-

    12. BGBill Gurley57:36

        [chuckles]

    13. CWChris Williamson57:37

        I, I realized that flattery was, was one of the big drivers, I think, for, uh, bringing people on the podcast especially. No one knows who it is. It's this random British guy asking you if you should come on. I always used to ask people, uh, "Can you please put me in touch with whoever handles your podcast adverts?"

    14. BGBill Gurley57:55

        [chuckles]

    15. CWChris Williamson57:56

        And it's some small-

    16. BGBill Gurley57:58

        I get it

    17. CWChris Williamson57:59

        ... researcher at fucking University of Arizona.

    18. BGBill Gurley58:02

        Uh-huh.

    19. CWChris Williamson58:03

        And, uh, they're like, "Oh, well, it's just me that handles my pod-" I'm seen in the echelons of those that would have an assistant or perhaps a receptionist that would handle-

    20. BGBill Gurley58:13

        I get it

    21. CWChris Williamson58:13

        ... my podcast ads.

    22. BGBill Gurley58:14

        I get it.

    23. CWChris Williamson58:14

        So... And that's, that's still now. Please pass me on to whoever handles your podcast ads.

    24. BGBill Gurley58:18

        Yeah.

    25. CWChris Williamson58:18

        And that's actually another good one, I think, just generally for any outreach to somebody. You wanna be in front of the right person, and especially if you're starting to pitch up toward mentors. That right person who actually handles that thing might not be them. So, uh, you know, reaching out, "Can you please put me in touch with whoever handles Bill's-

    26. BGBill Gurley58:36

        Yeah

    27. CWChris Williamson58:37

        ... uh, inquiries for coffee?" Or whatever it might be-

    28. BGBill Gurley58:39

        Yeah

    29. CWChris Williamson58:39

        ... to the, to the admin inbox.

    30. BGBill Gurley58:40

        Yeah.
12. 1:00:53 – 1:07:37

    Can You Learn to Love the Grind?

    1. CWChris Williamson1:00:53

       So in your framework, loving the grind is sort of a non-negotiable.

    2. BGBill Gurley1:00:58

       Yeah.

    3. CWChris Williamson1:00:59

       Can someone sort of learn to love grinding or is that innate?

    4. BGBill Gurley1:01:04

       I don't think so. But, you know, when you were talking about, um, your, your love of podcasting, you know, the, the word that popped into my brain, and there's a book by this title, was Flow.

    5. CWChris Williamson1:01:18

       Mm.

    6. BGBill Gurley1:01:18

       And I-I just find people that are truly tilting against their passion, they never even think about it as work. Like, it... And, and at times, the experience does go into this flow thing. Like, where when it-- when you're done, you don't even remember doing it. Like, you're just that much enamored with the whole thing. And because I've felt that and I've seen it, I just... I really don't know how you could do that. I, I suspect some human is just wired in a certain way where they might be able to do it, but I don't know that most humans could. Like... And I don't know... I, I do think we get a lot of young people to do it for an extended period of time.

    7. CWChris Williamson1:02:06

       Mm.

    8. BGBill Gurley1:02:07

       Um, and, and I meet-

    9. CWChris Williamson1:02:09

       The meat, the meat grinder thing.

    10. BGBill Gurley1:02:10

        Yeah, I meet so-- I, I just yesterday met with five of the top... I, I helped start this robotics honors program at Texas, and I met with five of them. And like, you know, they're giving you their background, Eagle Scout and, and it's fifteen eighty SAT and all. Like, clearly this human's been programmed to go take the hill, like, on every single thing they do. But I don't think that's the path to greatness. Like, you know what I'm saying? I just don't think... I don't think just being good at the grind is w- is what it takes to, to be truly exceptional.

    11. CWChris Williamson1:02:48

        Brute forcing creativity, uh, sort of w- white-knuckling your way through miserable successes, uh, it lasts for a good while and might be sort of the activation energy you need to overcome some discomfort at the start. But I would agree, I think-

    12. BGBill Gurley1:03:03

        And may-maybe if you're just so damn competitive, like winning all the time is your-

    13. CWChris Williamson1:03:08

        That winning is your passion

    14. BGBill Gurley1:03:09

        ... is your juice.

    15. CWChris Williamson1:03:09

        It's a meta passion.

    16. BGBill Gurley1:03:10

        That's possible.

    17. CWChris Williamson1:03:11

        Yeah, that's interesting.

    18. BGBill Gurley1:03:12

        Yeah.

    19. CWChris Williamson1:03:12

        And that's certainly some people, right? They just want to win.

    20. BGBill Gurley1:03:15

        Yes.

    21. CWChris Williamson1:03:15

        Uh, I think Michael Jordan would be a good example of this. Have you heard, uh, Novak Djokovic's, uh, interview where he's asked why he's so good at tennis, and he says, "I just like hitting the ball"?

    22. BGBill Gurley1:03:26

        [laughing] I love that.

    23. CWChris Williamson1:03:28

        Yeah. Um, whereas, you know, Jordan invented rivalries.

    24. BGBill Gurley1:03:34

        Yeah.

    25. CWChris Williamson1:03:34

        Like he invented slights against himself. There was... Was it '92 or '93?

    26. BGBill Gurley1:03:37

        Very driven human being.

    27. CWChris Williamson1:03:38

        He, he wins some... I think it's his induction into the Hall of Fame, and during that speech, h- this, this is the moment that you've worked supposedly your entire career for.

    28. BGBill Gurley1:03:50

        He takes a shot at somebody, right? [laughing]

    29. CWChris Williamson1:03:52

        He spends the entire speech just revealing all of the slights that from his past and this person and this per-

    30. BGBill Gurley1:04:00

        [laughing]
13. 1:07:37 – 1:25:21

    The Pains and Pleasures of Reinventing Yourself

    1. CWChris Williamson1:07:37

       more.

    2. BGBill Gurley1:07:37

       Yes.

    3. CWChris Williamson1:07:37

       Well, so y- you talk about honing your craft. Kind of interested in what that looks like in knowledge work when there's, there's no clear scoreboard.

    4. BGBill Gurley1:07:47

       Well, here, here's, here's what I would say is... And, and I think this relates to this college grind. I think some of these kids are so burned out by the time they get to the end of their senior year in college that they can't wait to not study anymore. Like they, they view it as, "Okay, 12 years plus four, 16, I'm done." And they're looking for a break from studying. And the best in their field, like Danny Meyer, are studying all the time. And so that's a, that's a weird contrast. Like, a- and there are fields where continuous learning is somewhat required. The, the medical profession is one where that happens. Um, and obviously there are fields like, uh, ballet, where if someone says they work 16 hours a week, we... or a day, we all applaud it. Which is weird, because if you said that about a engineering career, they'd say, "You're a bad human," you know? But whatever. Um, so this, this, this notion of learning constantly in your spare time, I think it's just the best test of whether you're truly obsessed with what you're doing.

    5. CWChris Williamson1:08:59

       Do you remember when, do you remember when Elon took over X and he did that announcement post and he said, "We are looking for people who want to work on the hardest problems possible as long as they can at an unrelenting pace to try and change the world"? And there was a lot of quote tweets of this saying, "We're throwing it back to a version of work-life balance that is-"

    6. BGBill Gurley1:09:22

       Yeah

    7. CWChris Williamson1:09:22

       ... completely primitive. This is abuse. This is horrendous-"

    8. BGBill Gurley1:09:27

       Yeah

    9. CWChris Williamson1:09:27

       ... all the rest of it. And don't get me wrong, there are certainly some bosses in some industries that will drive their employees so hard that it's irresponsible. But if you're stating it up front-

    10. BGBill Gurley1:09:38

        Yep

    11. CWChris Williamson1:09:38

        ... what all of those people that quote tweeted it and complained about Elon's horrendous working conditions failed to understand is there are people out there to whom that sounds like a dream.

    12. BGBill Gurley1:09:53

        Yes.

    13. CWChris Williamson1:09:53

        They want to work 18 hours a day-

    14. BGBill Gurley1:09:56

        Yeah

    15. CWChris Williamson1:09:56

        ... fueled exclusively on high-quality stimulants and Chick-fil-A.

    16. BGBill Gurley1:10:02

        Especially if they get to hang around with the smartest people they probably know.

    17. CWChris Williamson1:10:05

        And they wanna be pushing each other, and they want, they want to send it. They want to send the living shit out of it.

    18. BGBill Gurley1:10:10

        You know who's doing that right now, which is super interesting? The young AI founders.

    19. CWChris Williamson1:10:14

        Mm.

    20. BGBill Gurley1:10:14

        They, they've embraced this, uh, meme from China, 996. It actually was developed in China, which means, uh, nine, 9:00 a.m. to 9:00 p.m. six days a week.

    21. CWChris Williamson1:10:25

        Yeah.

    22. BGBill Gurley1:10:25

        That's what it stands for. But they use the phrase. And Silicon Valley got lazy in COVID. So you have the situation where the broader culture had moved from being formerly a bit workaholic to being lazy. And despite the [chuckles] you know... They, they literally aren't coming into the office. You can go in downtown San Francisco and look through buildings, you know, 'cause there's so much cubicle space with no one there.

    23. CWChris Williamson1:10:54

        Yes.

    24. BGBill Gurley1:10:54

        And these young kids in this AI world-

    25. CWChris Williamson1:10:56

        Eating their lunch

    26. BGBill Gurley1:10:57

        ... are the ones you're talking about that want that experience.

    27. CWChris Williamson1:11:01

        Who are some examples of those?

    28. BGBill Gurley1:11:02

        Uh, I, I think almost all of... I'm, I'm, I'm serious. Almost all of the AI companies in San Francisco have this mindset, especially if they have a young founder.

    29. CWChris Williamson1:11:12

        Wow.

    30. BGBill Gurley1:11:12

        Like a 20, 22. Which is... But they're, but they, it, it, it, it... The... I'm, I'm agreeing with you. Like this notion that, okay, you don't like it 'cause you don't think there's work-life balance. Do you think it should be illegal for them to do it?
14. 1:25:21 – 1:30:34

    What Bill Looks For in the Founders He Backs

    1. BGBill Gurley1:25:21

       so-

    2. CWChris Williamson1:25:22

       Speaking of that, you're a very successful investor. What were you looking for in the founders that you invested in? What were the traits? What were the global-

    3. BGBill Gurley1:25:32

       Yeah

    4. CWChris Williamson1:25:33

       Decision framework

    5. BGBill Gurley1:25:34

       And, and a lot of VCs say the same things over and over, so I'm a little-

    6. CWChris Williamson1:25:38

       It's fine

    7. BGBill Gurley1:25:39

       ... hesitant, but I'll do it anyway. [chuckles] Um, the one that took me the longest to fully recognize is how important product in- product instincts are. So that's critical. Like, like new-- most of these companies are riding some new wave like this AI wave, and the product, uh, surfaces of the new thing aren't as well understood as the ones of the old thing. Think about the, the mobile-

    8. CWChris Williamson1:26:03

       Right, okay

    9. BGBill Gurley1:26:04

       ... movement. And, and-

    10. CWChris Williamson1:26:04

        So you're predicting

    11. BGBill Gurley1:26:05

        ... and you need instinct to get that right. Like, you just need instinct-

    12. CWChris Williamson1:26:09

        So you gotta be ahead of the market

    13. BGBill Gurley1:26:10

        ... about humans and how humans like to interface with things, and a whole bunch of stuff. So product's a big one. Um, salesmanship is a huge one that, that people probably don't think about enough. But if you're a founder, you're selling to new investors, you're selling to employees, you own the company culture and the perception of the company. You're striking deals, you're selling to customers. You're just out selling all-- You're the number one sales- you're the chief salesperson for your company. And if you're no good at it, um, it-- you will struggle. So that, that's another one. Determinism, you know, and it kinda goes back to everything we're talking about with chasing your dreams, but, you know, Josh Wolfe at Lux Capital says, "Chips on shoulders put chips in pockets." And-

    14. CWChris Williamson1:27:01

        Mm.

    15. BGBill Gurley1:27:01

        Like, like someone that, that maybe failed a couple times is-

    16. CWChris Williamson1:27:06

        Got a point to prove

    17. BGBill Gurley1:27:07

        ... oh, man, you wanna feel that. Like, you wanna feel that they're never gonna give up.

    18. CWChris Williamson1:27:13

        Bit of grit.

    19. BGBill Gurley1:27:14

        Yes. Like, not a bit. Like, you want, you want top one percentile. [chuckles]

    20. CWChris Williamson1:27:18

        Yeah.

    21. BGBill Gurley1:27:19

        You, you, you wanna be afraid a little bit [chuckles] about how determined they are.

    22. CWChris Williamson1:27:25

        Mm.

    23. BGBill Gurley1:27:26

        You know?

    24. CWChris Williamson1:27:26

        What was that line, uh, "Is this person going to do this no matter what?" Was that Bezos?

    25. BGBill Gurley1:27:31

        Yeah. Bezos. I, I asked Bezos-- You found that. I asked Bezos once how he could be such a successful angel investor, because he's running the largest employment count company in the world. Like-

    26. CWChris Williamson1:27:43

        He has other shit to do.

    27. BGBill Gurley1:27:44

        Like, like yeah, exactly.

    28. CWChris Williamson1:27:45

        He has less time than you to scrutinize the-

    29. BGBill Gurley1:27:47

        No, way less.

    30. CWChris Williamson1:27:48

        Yep.
15. 1:30:34 – 1:42:01

    Is the Founder More Important Than the Company?

    1. CWChris Williamson1:30:34

       Um, uh, going back to the founder thing, is the founder more important than the company to you in some ways? Would you bet just on a founder that this person will find a thing?

    2. BGBill Gurley1:30:45

       Well, here's one, one proof point that would speak to this is, um, there, there are m-multiple companies that the original idea completely failed and the founder was able to pivot to something entirely new and be wildly successful.

    3. CWChris Williamson1:31:02

       What like-

    4. BGBill Gurley1:31:03

       Slack is an example. It was a game company.

    5. CWChris Williamson1:31:06

       S-

    6. BGBill Gurley1:31:07

       And the game failed, but they had built this tool to develop the game.

    7. CWChris Williamson1:31:11

       [chuckles] I didn't know about that. That's so cute.

    8. BGBill Gurley1:31:13

       And it became Slack. Um, Discord, who's one of our companies, was also a game company that failed and launched this Skype alternative for communicating during games that became wildly successful. And for any venture capitalist that's been through one of those pivots, they're famously known as pivots now, um, it's all about the person. Like, it's all about the founder.Like, um, there's also a data point that most venture capitalists will quote, and I'm sure it's not scientific, but a new CEO hire is a fifty-fifty bet at best. So why, if you're doing positive-- like trying to run MPVs, would you even take the risk of hiring a CEO because you're gonna... There's a fifty-fifty chance you'd just get a bad apple-

    9. CWChris Williamson1:32:04

       Mm.

    10. BGBill Gurley1:32:04

        -in which case it's all toast.

    11. CWChris Williamson1:32:06

        Mm.

    12. BGBill Gurley1:32:07

        So yeah, there's... And, and that lore goes beyond me. I mean, I think the, the founder, um, mythology, if you will, is quite high in Silicon Valley, uh, for all those reasons. Now, there are times where you have no other option, and there are s-- there's way more stories... This is kind of an odd fact, but companies that serve businesses, um, have a much higher success rate of replacing the founder than companies that serve consumers.

    13. CWChris Williamson1:32:37

        Why do you think that is?

    14. BGBill Gurley1:32:38

        My best guess is consumers are more fickle and that that product thing is just more, um, artistic, you know, more like-

    15. CWChris Williamson1:32:47

        Sounds like a taste again.

    16. BGBill Gurley1:32:48

        Yes. More like a movie than, than-

    17. CWChris Williamson1:32:52

        I love that, I, I-

    18. BGBill Gurley1:32:52

        You know, business.

    19. CWChris Williamson1:32:53

        I love that.

    20. BGBill Gurley1:32:53

        And business products are more systematic.

    21. CWChris Williamson1:32:55

        Yeah. Yeah.

    22. BGBill Gurley1:32:56

        And, and-

    23. CWChris Williamson1:32:57

        You can algorithm that down to-

    24. BGBill Gurley1:32:58

        Steve Jobs once said that the difference is the buyer in a business isn't the user.

    25. CWChris Williamson1:33:05

        Mm.

    26. BGBill Gurley1:33:06

        And he made that point, and that may be it. Like, that may be the essence of it.

    27. CWChris Williamson1:33:12

        That's cool. I, um... Th-this thing, the, the beverage that you're drinking is mine, and that's the first big company that hasn't been something that I've directly operated aggressively myself, that I've founded. And, um, one of the interesting elements that I've seen with this, where we, we did a raise last year. We raised three point four, four million dollars, and right now we're in the middle of raising six and a bit. Uh, I'm watching Luke, who is one of the co-founders. Today, he [chuckles] drove from Portsmouth on the South Coast to Leeds, which is five and a half hours away. It's fucking forever away. Drove to Leeds for one investor meeting.

    28. BGBill Gurley1:33:56

        Yep.

    29. CWChris Williamson1:33:56

        To just sit down with this guy. And when you think about as you're sort of reeling off all of these different traits that he's-- that, that you would have sort of the obsession, the determinism. And, um, what's been cool is to see... You almost get to learn what people think of you when you do fundraising, when you're trying to get cash to inject into a business that's yours. You almost see in the responses from people. And, uh, a couple of times [chuckles] we've sent the deck out. This was in the first one. So we send this deck out, and it's all sexy, and it's got-

    30. BGBill Gurley1:34:26

        Yep
16. 1:42:01 – 1:47:13

    Why You Should Lean into AI When Honing Your Craft

    1. CWChris Williamson1:42:01

       question. What, what are you ex- most excited about with regards to the industry of AI, and what do you think is overblown?

    2. BGBill Gurley1:42:11

       I would-- I mean, it'd be a little redundant, but the thing I'm most excited about is just the personal empowerment. You know, there's all kind of anthropologists that will tell you we evolve with our tools. Humans, like, like it's very clear, right? If I had a plow and a tractor and a, and a, and a computer and a chemistry set, and the other guy's the guy in Naked and Afraid, like I'm gonna be more evolved than him. I can do more stuff.

    3. CWChris Williamson1:42:39

       Mm-hmm.

    4. BGBill Gurley1:42:40

       And this is the latest of those things. And, um, anyone that is a skeptic or... And I've met a lot of like the top academicians that are skeptics in all this. You are... You're no different than the Luddites with the, with the looms in Europe. Like, you're just not. It's the modern version of that.

    5. CWChris Williamson1:43:01

       Mm-hmm.

    6. BGBill Gurley1:43:01

       And the number one thing you can do to future-proof yourself is to run at it. Like to know whatever industry you're in, there is an edge of what is AI capable of in this industry, and you wanna be right there. You wanna be aware of exactly what that is. And if you are the most AI productive human in your field, you're not getting fired. [chuckles] Like you're, you're the one they're asking all the questions of, like what's this capable of? Um, and so I, I... In, in the, in the chapter I have on Hone Your Craft, I say study the history and study the edge. Like if you can quoteFrom the founding fathers of your industry and you know exactly where the technological edge is, you look like a unicorn. You look-

    7. CWChris Williamson1:43:53

       Going in the middle is where you die?

    8. BGBill Gurley1:43:55

       Yeah. I mean, everybody knows the middle. Like, I'm just talking about differentiating yourself.

    9. CWChris Williamson1:43:58

       Of course. Of course.

    10. BGBill Gurley1:43:59

        Yeah. So anyway, I, I find... I mean, I haven't... I, I, I'm anxious. This is why also why I was a, a, a useful, I use the word useful venture capitalist. I have FOMO about new shit that I don't understand. So up until at least a year or two ago, if something sh- if there's an app in the App Store in the top ten I've never heard of, like hives, like I have to know. I have to know.

    11. CWChris Williamson1:44:26

        [laughing] You're allergic to ignorance.

    12. BGBill Gurley1:44:27

        I'm, yeah, I'm coming off of it a bit because I haven't done a Clawbot yet, which I feel guilty about.

    13. CWChris Williamson1:44:32

        Well, you can't get a, you can't get a fucking Mac Mini. That's why. You're not gonna be able to buy them. They're all sold out.

    14. BGBill Gurley1:44:37

        [laughs] But I feel guilty about that.

    15. CWChris Williamson1:44:39

        Yeah, yeah, yeah. You've got massive FOMO.

    16. BGBill Gurley1:44:41

        Yes.

    17. CWChris Williamson1:44:41

        Pod FOMO.

    18. BGBill Gurley1:44:42

        That... But, but it's useful. Like, and so anyway, that... I, I think that, um, the, there, there... I would also say this about AI. If you're not leaning in, not only... People have said there's prompt engineering skills. Not only are you not learning that, but I find every day I think of a new way to use it and a new way to test what it's capable of. And if you're in it every day, you're helping to explore that boundary, and you're all of a sudden learning new things. Do, do you understand what I'm saying? Like, um, I had this great experience with the, with the concluding chapter in the book. So my-- you know, almost done wrapping up, feeling good, and the editor says, "Bill, take a shot at the conclusion this weekend." So I spent six hours, seven hours. I sent him something. He's like, "This sucks." Like, first time... Like, it was really the first critical fee- he didn't use that phrase. "Yeah, I really don't like this." So I asked ChatGPT in the pro version, the $200, $300 a month, whatever it is, "Write me a 20-page report on the best concluding chapters in nonfiction books of all time, and give me a summary of each and what made it special." And in reading through that list, I noticed that eight or nine of the ten took an orthogonal direction to the book. So it didn't summarize.

    19. CWChris Williamson1:46:13

        Well, that's interesting.

    20. BGBill Gurley1:46:13

        It brought in a new point.

    21. CWChris Williamson1:46:14

        Yeah, yeah, yeah.

    22. BGBill Gurley1:46:14

        A new perspective.

    23. CWChris Williamson1:46:16

        Yep.

    24. BGBill Gurley1:46:16

        And that gave me an idea. I, I then went and, and ideated on that concept, and it gave me a new idea to take it in a different direction. And-

    25. CWChris Williamson1:46:27

        What was the idea?

    26. BGBill Gurley1:46:28

        The editor loved it. Huh?

    27. CWChris Williamson1:46:30

        What was the idea?

    28. BGBill Gurley1:46:32

        Um, the, the... Not... I, I... All right, I'll give this one away. Um, the concluding chapter's titled It Ain't Easy. And so the whole book is an exercise in trying to encourage you to go do this, and this is a little warning at the end. Like, it ain't easy. You gotta struggle. You gotta suffer. You gotta be okay with failure.

    29. CWChris Williamson1:46:56

        In praise of the grind.

    30. BGBill Gurley1:46:58

        Yes. And the editor loved it.
17. 1:47:13 – 1:49:11

    What Careers Will AI Make Obsolete?

    1. BGBill Gurley1:47:13

       Um...

    2. CWChris Williamson1:47:13

       When it comes to the AI thing, what, what do you think it's gonna do to the field of work generally? What, what areas would you be worried that are gonna be obsolete?

    3. BGBill Gurley1:47:21

       Um, anything that was synthesizing... I mean, so the LLM, large language model, is really good at text. Really, really good at text manipulation. So if your job involved searching for text, summarizing text, um, anything like that, um, paralegals are already under threat. And I have talked to lawyers that have drastically reduced the size of their paralegal force. I've talked to them. That has already happened. Um, coding, it turns out, is highly structured text, more structured than text itself, right? If you think about it.

    4. CWChris Williamson1:48:08

       Mm.

    5. BGBill Gurley1:48:08

       It's got more constraints.

    6. CWChris Williamson1:48:10

       There's more rules.

    7. BGBill Gurley1:48:10

       It... There's, there's more freedom in actual language text than in coding. And that makes... And so coding's under threat. And the best people that will write or will generate the most code in the future are the ones that learn to, to be able to harness that tool the way a farmer learned to use a tractor instead of plowing.

    8. CWChris Williamson1:48:32

       Mm.

    9. BGBill Gurley1:48:33

       And that's your only choice. Like, the, the... There's no hand hoe-ers anymore. Like, they don't exist. And, and so this text thing's a big deal. Um, you know, if you translated something, that's a dangerous job.

    10. CWChris Williamson1:48:49

        Mm.

    11. BGBill Gurley1:48:50

        And someone needs to kinda make sure the translation's right.

    12. CWChris Williamson1:48:54

        Yeah.

    13. BGBill Gurley1:48:54

        But that's a different job. It's more of a editor of translation, right? And that's an opportunity to move upstream, be the, be the one that's best at exercising that with this tool. But the old tool doesn't, doesn't work. Like, it's not gonna be

18. 1:49:11 – 1:50:56

    The Best Way to Start Your Career in Your 20s

    1. BGBill Gurley1:49:11

       real.

    2. CWChris Williamson1:49:12

       If you were 21 and starting again with no knowledge or connections, what do you think you'd be focused on? What would you do?

    3. BGBill Gurley1:49:19

       Um, it would definitely be related to AI. I mean, it just would. Like, I'd be rolling around in it, um, more. I would definitely have already launched ten ClawBots versus now where I don't have that, that need, um, to see what's possible. I'm, I'm fascinated by the, uh, the agent idea for a personal assistant, like a running buddy. I just find that fascinating.

    4. CWChris Williamson1:49:47

       Mm.

    5. BGBill Gurley1:49:49

       I s-- another one that I kind of am fascinated by, I think someone will build a new CRM from scratch that will be used by small companies that don't have a CRM because it's easier to start with zero in the database. And I think that will be super clever, that product that... I don't think you can get there from Salesforce because you've got this huge database with all these fields and forms that no one wants to look at. And if you start with that as your construct, I think you'd build the wrong thing. Does that make sense?

    6. CWChris Williamson1:50:22

       Because you're trying to backwards integrate something that's already a little jank.

    7. BGBill Gurley1:50:28

       And I don't think the user wants to even see that stuff. Like-

    8. CWChris Williamson1:50:32

       That's interesting

    9. BGBill Gurley1:50:33

       ... and so it should-- whatever the storage mechanism is, I don't think it will be visible to the user in the way that it, a database like type enterprise app historically did it.

    10. CWChris Williamson1:50:47

        Mm. Mm-hmm.

    11. BGBill Gurley1:50:48

        You know. So, so anyway, those are things that pop into my brain when you say that. Those are things I'd be playing with.

19. 1:50:56 – 1:55:43

    Why Career Switchers Often Become Innovators

    1. CWChris Williamson1:50:56

       I know that you're a big reader. What have been the books over the last couple of years that you have not been able to stop telling people about?

    2. BGBill Gurley1:51:05

       Um, the second half of Range impacted me in a big way.

    3. CWChris Williamson1:51:10

       David Epstein?

    4. BGBill Gurley1:51:11

       Yeah.

    5. CWChris Williamson1:51:11

       Yeah.

    6. BGBill Gurley1:51:12

       And the book's known for being this antidote to Malcolm, although they're very close friends. In fact, Malcolm's quoted on the cover of Range, I think. Um, um, but the book, people talk about this generalist versus specialist and this comparing of, you know, these two athletes. But he gets into a very different subject in the second half of the book. He gets into this notion, um, which I had, I'd always heard, heard a phrase called far analogies. But he gets into this notion that people that switch industries or switch careers or switch academic, um, focuses tend to be the biggest innovators of all time. And they come into something with a different, um, mental model than the people that came up through the field. Like if they enter through the side door.

    7. CWChris Williamson1:52:04

       Mm.

    8. BGBill Gurley1:52:04

       You understand? The-- And it relates to the-

    9. CWChris Williamson1:52:06

       They see things differently

    10. BGBill Gurley1:52:07

        ... the generalist. Yeah. Yeah. And, and they're, they're able to bring patterns from... or see patterns other people may not see.

    11. CWChris Williamson1:52:14

        Mm.

    12. BGBill Gurley1:52:14

        And I, I just find that fascinating. I touch on it in a couple of the chapters. I-- in the learning chapter and the peer chapter, I say, "If you make it far enough, you wanna stretch the peer to someone that's maybe in a different industry. You wanna stretch the learning to other industries." And it's where you find some of the biggest nuggets. They're-- it's, it's more noisy. You're wading through-

    13. CWChris Williamson1:52:40

        Yeah

    14. BGBill Gurley1:52:40

        ... m- like it's harder-

    15. CWChris Williamson1:52:41

        Less aligned, right?

    16. BGBill Gurley1:52:43

        Yeah.

    17. CWChris Williamson1:52:43

        Yeah. Yeah. But the insights are power law step changes.

    18. BGBill Gurley1:52:46

        It'd be like you, like, listening to someone talk about, um, great writing technique and get an idea for the podcast.

    19. CWChris Williamson1:52:54

        Mm-hmm.

    20. BGBill Gurley1:52:55

        Y-you know? It's-

    21. CWChris Williamson1:52:55

        But one of the things that I did about four years ago when I first moved to America was I got obsessed with cinematography. And cinematog-- we-- obviously, there's cameras and videos-

    22. BGBill Gurley1:53:03

        Right

    23. CWChris Williamson1:53:03

        ... and stuff here. Um, but we started doing this thing called the Cinema Series, and this was shot like a movie, and it culminated... Episode one thousand was me recreating the house from Interstellar on a eighty-five-foot video wall, the biggest video wall in Texas, using the same technology that Star Wars uses.

    24. BGBill Gurley1:53:24

        Yeah.

    25. CWChris Williamson1:53:25

        And we rendered the entire scene in Unreal Engine five and then did set dressing, so we had live elements of, of dirt on the floor and cactuses, and we reversed a fucking Airstream in. And I sat opposite McConaughey, and I sat him down, eleventh anniversary of Interstellar, and we were sat in front of the, the house from, from, from the movie. And that was because, oh, I, I started learning about this, and I started getting friends that were from the cinematography industry, and I started asking them, "Well, what would you do if you were trying to elevate a podcast?" Da, da, da, da, da. And then it-- we did some cool things, and it's largely a passion project wing of what we do, but it's, uh, it's cool. It's different.

    26. BGBill Gurley1:54:05

        In, in his famous, uh, Stanford graduation speech, Jobs said if he had never taken a calligraphy class, he doesn't know if he builds the iPhone the right way, you know, and the Mac, you know. It, it may or may not. It may be-- it may just be kind of nostalgia speaking, but there, there are things you can borrow from learning far away that can be very impactful. And it's hard to know at the time, like when you're consuming it. That's why I call it a bit of a superpower or advanced level, I think I call it.

    27. CWChris Williamson1:54:36

        Mm.

    28. BGBill Gurley1:54:36

        It's not easy.

    29. CWChris Williamson1:54:38

        Well, because you're translating, it's like an exchange rate between something else and this. So does that w- Is that just cool for them to really take what that musician's doing? Or is this relevant to me? So I guess taste, discernment. And when I think about areas that, uh, AI can't replicate, uh, community, networking ability, taste, discernment.

    30. BGBill Gurley1:55:00

        Yes. I agree.
20. 1:55:43 – 1:56:52

    Where to Find Bill

    1. CWChris Williamson1:55:43

       different. Heck yeah. Bill Gurley, ladies and gentlemen. Bill, you're fucking awesome.

    2. BGBill Gurley1:55:47

       Thank you for having me. I really appreciate it.

    3. CWChris Williamson1:55:48

       A lot of my friends said, "You're gonna love his energy," and sure enough, you're-

    4. BGBill Gurley1:55:51

       [laughs] Thank you

    5. CWChris Williamson1:55:52

       ... you're, you're, you're a legend. I'm glad that you're occupying some of those high-rises down... I've always wondered who lived in them.

    6. BGBill Gurley1:55:57

       [laughs]

    7. CWChris Williamson1:55:57

       So it's, uh, it's good. Where should people go to check out everything you're doing?

    8. BGBill Gurley1:56:01

       Um, so, so I've historically spent most time... We were an investor in Twitter early on, so I've developed my X profile the most, and that's where I post most stuff. So it's B-G-U-R-L-E-Y. There's a, there's an Instagram account that I'm, for the first time in my life, developing for the book.

    9. CWChris Williamson1:56:22

       Congratulations. Welcome.

    10. BGBill Gurley1:56:23

        Which is bgurley. Yeah, it's a different world. Like, I feel like such a neophyte. [laughs] Like, in Twitter, I get everything.

    11. CWChris Williamson1:56:31

        Yeah.

    12. BGBill Gurley1:56:31

        In-- Like, I understand it.

    13. CWChris Williamson1:56:33

        Instagram's a different language.

    14. BGBill Gurley1:56:34

        Yeah, it's a different language. I'm figuring it out.

    15. CWChris Williamson1:56:37

        Heck yeah. Bill, I appreciate you.

    16. BGBill Gurley1:56:38

        Thank you, sir.

    17. CWChris Williamson1:56:39

        Thank you, man.

    18. BGBill Gurley1:56:40

        Bye.

    19. CWChris Williamson1:56:40

        [outro music] Thank you very much for tuning in. Congratulations for making it to the end of an entire episode. Uh, another one that I think you'll enjoy is right here.

Episode duration: 1:56:52