Why ‘Playing It Safe’ In Your Career Doesn’t Pay with VC Bill Gurley

12:25Kara Swisher:Right, we're going to get to those in a second.

12:26Bill Gurley:But almost every single one of these people started on the bottom rung. My favorite story from that perspective is Jen Atkins, who's probably the most famous hairstylist of all time. but she moved to LA with$200 in her pocket, like to start this journey. And so, I mean, that's just one anecdote, but that's not necessarily consistent with starting on third base or being rich when she decided to do it. The other thing I would say is, you know, Scott's not the only one that says that. I've heard another VC say that. And I think Palmer Luckey said it the other day.

12:59Kara Swisher:I'm going to take his advice, but go ahead.

13:02Bill Gurley:Well, but I wonder if there are people that are hyper competitive and just love winning. Maybe not in Scott's case, but in this VC's case and maybe Palmer's case. And if you love winning to death, like then that is your passage. If winning is your passion, it would be logical that do whatever your most skills at because that's your best chance of winning. Yet the number one reason I think parents get into that game of the grind and pushing, we didn't mention pushing kids towards safe jobs is a worry about economic stability.

13:39Kara Swisher:Right. Absolutely.

13:39Bill Gurley:I think the way you end up with 53 % of the population uninspired by work is you were sent to do a job that was a safe job that you don't have. For money. A real passion for.

13:51Kara Swisher:For economic reasons.

13:52Bill Gurley:Yeah. Yeah. Yeah. Yeah.

13:53Kara Swisher:Right. So let's dive into the few of the six principles you lay out in the book to achieve a flourishing purpose-filled careers. You wrote, finding your fascination is the hardest, most mystical of all the principles in the book. If you were talking to a young person who's tried to figure out their passion or fascination and failed, what would you tell them? And what's the process for figuring that out?

14:12Bill Gurley:Yeah, and I've got a whole chapter dedicated to this. And I think there's a number of things that are important. One, give yourself permission to move on. One of the problems, I think, when you push these kids so hard through that college conveyor about is they develop a sense that they've made an investment that they can't move away from because of sunk costs. Like, oh my God, I've invested so much in this. And yet many, many people shift careers that aren't consistent with their major. Dave Evans at Stanford has studied this like 10 years out, less than 50 % of people are still in that place.

14:50Bill Gurley:So one thing is just to give yourself permission that it's not failure if you want to go try something out. You know, Angela Duckworth has, in a graduation speech, said, act like a paramecium, move towards warmth and nutrients. And just really pay attention, even within a company, that the stuff, you know, anyone working within any company probably has at least eight different things that they do. Which ones do you like the most and move in that direction? One of the founders of the Acquired podcast had this thing he used called side hustles, where if he got a job, he would ask the employer, in my spare time, can I do this other thing to help the company out?

15:32Bill Gurley:And they almost always said yes. They almost always gave him kudos for being innovative and pushing some new direction. And that's how he discovered he loved podcasting. He was at Madrona and asked if he could start a podcast.

15:46Kara Swisher:And you also have to have a job person that's willing to do that. When I had a very successful conference series. I had a very successful website, journalism career. And I got paid a lot of money for selling it to Jim Bankoff. And I said to him, I'm going to do a podcast. This was 10, 12 years ago because I love it. And you have to have someone willing at a company to say, every time she has a passion, it works out well financially for everybody. So that's one of the things is not just finding your fascination, but getting support for that, presumably.

16:18Bill Gurley:There's no doubt. And parental support's a really interesting thing. There's an anecdote I discovered after the book was out where McConaughey was, another Austinite here, was at Texas. And he had told his father he wanted to be a lawyer for a long time. And his father had started repeating that to family and friends. So it was kind of this expectation that was in the water and he decided he wanted to go to film school. And he had all this anxiety about calling his father, you know, what's he going to say? Am I going to, and he finally gets him on the phone and tells him and his dad pauses and then says, well, don't half-ass it.

16:56Bill Gurley:And McConaughey says it was the last thing he expected and the best thing he could have said. Because it said, not only is it okay, but if you're going to do it, like I expect you to do it really well. And so it was this push with both support but responsibility. And, you know, as a parent, and I've seen this, like, you want to push them towards the safe job with the money. And it's just an instinct that people have.

17:24Kara Swisher:Well, they often want to do it. I just had a discussion with my oldest son about it. And he's like, well, I have to. I'm like, why don't you figure out what you're good at and then you will earn money. It's, you know, an odd thing. But speaking of Angela Duckworth, who you mentioned, when I interviewed you in 2016, you brought up her book, Grid. I don't know if you remember that. This is 10 years ago almost. Her thinking has clearly been influential on you. She comes up a lot in the book. One of her findings is that the why is usually the overt part of finding your passion or fascination. In other words, purpose matters.

17:52Kara Swisher:What is your why? And talk to you how you figured it out and why that is important, why the why is important, I guess.

17:59Bill Gurley:Well, the second principle of my book is titled Hone Your Craft, and it's about lifelong learning. And there's a real symmetry between what we call chase your curiosity or find your fascination in this hone your craft. Because for people that are in a job they love, the honing's free. And what I mean by free is you don't have to schedule it. You don't have to convince yourself to do it. It's not like going to the gym and working out for an hour. If there's some new paper published in your field, you chew it up. You just go read it. You prioritize it. And I think most importantly, you get energy from it.

18:36Bill Gurley:So rather than it being an energy sink, which studying in many cases for children is, it becomes an energy boost. And so it really becomes an unfair advantage in almost any industry if you're that person, because you're learning constantly.

18:53Kara Swisher:So talk about your why. Talk about how did you figure out what that was?

18:57Bill Gurley:Let me ask you a question. Are you interested in that for venture capital or that now, post-venture capital?

19:03Kara Swisher:Both. Try venture capital. What was your why? Why did you decide that?

19:06Bill Gurley:So when I was an engineer at Compact and I got started on our third project, it looked like the second, looked like the first. And I got intellectually bored, especially when I did this exercise, I asked myself, you know, do I see myself still here in 30 years? And I could imagine, even if I do well, I'm going to move up the engineering ranks. I'm either going to run an engineering group or become a highly ranked technical person here. And that was an easy no for me, you know, for whatever reason. And I'm thankful that I had that kind of ability to think forward like that. Bezos had something similar as regret minimization framework where when he was trying to decide to start Amazon, he asked himself, if I were 80 and giving myself advice, what would I say about this decision?

19:55Bill Gurley:It's kind of similar. No, it's similar.

19:57Kara Swisher:I was at the Washington Post and I looked around and I said, I don't want to be anybody here. I don't, so I need to go.

20:03Bill Gurley:Without necessarily judgment on anyone there, it's just not a fit for what you see as something that gives you energy.

20:09Kara Swisher:Let me press you. Does that require, and like I finished up this longevity thing. And one of the speeches I used was Jobs' famous speech to Stanford, Steve Jobs'. And it was about not having regrets. And if you say no when you wake up every morning, you need to get out. He was using death as the way, he said death is the greatest motivator. He had a sense of the longevity of a career. Is that hard to do when you're younger?

20:35Bill Gurley:I think it is. I mean, I think that's why I mentioned that exercise. And look, young people don't see the end of times. It's not part of their mental framework. And I don't necessarily think filling their brain with anxiety is necessarily a positive.

20:54Kara Swisher:You know, actually, death acceptance makes you live longer versus death avoidance. Okay, I'll buy that. And I think Jobs was onto something.

21:01Bill Gurley:But I wanted to pivot to one thing on the regret side. So Daniel Pink wrote a whole book about regrets and how they can motivate you to actually take these harder steps. And one thing he talks about in that is that the biggest regrets that cause the most anxiety for people, not just Americans, but he studied it in a bunch of different geographies is what he calls regrets of inaction or boldness regrets. And so we're relatively good as a species at forgiving ourselves for mistakes. We just don't dwell on them after they're done. But the thing we never did, the thing we always thought we should do that we didn't get to, those things weigh on our brain more and more and more as we get older.

21:45Kara Swisher:Right, the things we don't do. So when you left Compaq, but you have to have the why to go to. You don't want to just run away from something. You want to run to it. So why did you want to become a VC of all the many choices you had?

21:57Bill Gurley:So I don't know that it was that fine-tuned at that moment. And maybe this is part of the lesson. Like, it doesn't have to be. You're moving towards things that are interesting. You don't necessarily know where you're going. So while I was at Compaq, I had read One Up on Wall Street by Peter Lynch. And I had started studying and trading tech stocks just at home. And that's a really interesting place to look for what your fascination may be. If you're doing something in your free time that's different from what you're doing at work. And so I went to business school. I did have this sense at Compaq that there was a broader world.

22:31Bill Gurley:I had started reading the tech magazines that you were familiar with back in the day, PC Magazine and Byte. What was Arthur? Info World. Yeah, there were a lot of them. Yeah, so I started reading those and you could see there was more than just what was at Compaq. And I was curious about that. And then when I got to business school, I started reading way more books. I started reading the journal, Forbes, Fortune, and started to see a bigger world. Now, I did get options at Compaq. My sister was an employee there early. And so I had a sense, you know, Doar was on the board. So I had a sense that there was this venture thing, but I didn't really know how to get at it.

23:09Kara Swisher:It's John Doar. Yes.

23:10Bill Gurley:And it was interesting to me, but I didn't know how to get at it.

23:13Kara Swisher:So business school was the way got you to your why.

23:16Bill Gurley:Yeah, but I went through New York first. So I noticed that when I was reading those periodicals, the dream team at Goldman at the time that covered all the tech stocks, they were just mentioned constantly. And I really enjoyed my corporate strategy class at school. And these guys were answering those types of questions on these fascinating big tech companies. And so I kind of wanted to be a part of that and came to New York.

23:47Kara Swisher:Right, but it's interesting because to me, whenever I looked at investment banking, I thought about it, and I was asked by many people, it was always like, oh, you're the servants of the people who are actually doing things. Like, you're the man. Yeah. Or a lawyer or something like that. You're not the one doing. You're the one facilitating. But one of the things that was interesting that I think your book is unique is how you emphasize the need to find great group of peers. You illustrate that with a profan, Jimmy Donaldson, also known as Mr. Beast. even though you push companies to formalize these principles, none of them ever did it.

24:18Kara Swisher:What do you mean embrace your peers? Because there's so much infighting at these companies. And you even see it today in these AI companies. I'm exhausted by these people. The drama is ridiculous on some level. And of course, you were involved with Uber, which was the biggest telenovela of all time.

24:34Bill Gurley:Yeah. So what I'm talking about, and it's better exemplified in all the stories in the book and the Mr. Beast ones. Let's just do the Mr. Beast one really quickly because I think it highlights quite a bit. So he's 17 years old and develops a fascination for YouTube. And at the time, very few people share that fascination, but he finds three others that do. He finds them digitally and they end up spending, he says, 17 hours a day on Skype together for four years. And so what's going on there? Well, they're co-learning what it takes to be successful on YouTube. And he says all four of them ended up with over a million followers, all four of them ended up millionaires.

25:19Bill Gurley:And he says, if you were a fifth person on the Skype calls, you would have had that same outcome. Like it was that fresh of an information. And I think this could potentially be mirrored in almost any industry. And there's another example in the book of these people that were all in athletic departments working up from the very bottom, but had a connection together. I think you can form peers in your company. I think it's way better if they're not in your company, if they're outside your company. And what you're looking for is a group of people who all have the same ambition that you do, who are all on the same rung of the ladder moving up, that you're going to share ideas with, share your network with, root for, and then they're going to be there to support you when you have bad days.

26:05Kara Swisher:So why are so many people willing to do it?

26:08Bill Gurley:I don't know why. I think that there's two things that I think are fallacies. One, that you need to be sharp elbowed and you're climbing and stepping on the next person. And a lot of our strategies we come up with come from finite games like board games and sports games that have a beginning and a single winner. In most industries outside of downhill skiing, there are many, many winners. There's lots of successful VCs. There's lots of successful writers. There's lots of successful podcasters, engineers, salespeople. There's not one winner. And so I think getting that out of your brain is helpful.

26:48Bill Gurley:And then the second thing is people get overly concerned about sharing proprietary advice. And I'm personally, and others have said this, but I think Altman said it recently. Like, I think ideas are a dime a dozen. Like, you think you have a proprietary idea, but there are other people that have the same information.

27:08Kara Swisher:One of the things when you're writing above the crowd, people are like, why is he giving away his secrets? I'm like, he's not. He's not giving away. He's thinking it out. I remember having an argument with someone, and often when people ask me, especially other podcasters or anyone in my area, like, I share everything. And I'm like, you can't do it. I mean, you're not going to hurt me by me telling you my secret, my supposed secret.

27:29Bill Gurley:And you build trust and you build better, you better trust in those networks that get more information sharing the other way. It just, and I think it's just more fulfilling to have more people in your circle, you know, rooting for you and you rooting for them.

27:48Kara Swisher:We'll be back in a minute.

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30:23Kara Swisher:That's HungryRoot.com slash onwithKara. Code onwithKara to get 40 % off your first box and a free item of your choice for life. That means for life. It's delicious. You'll feel better. When you want your spring break to feel like... And your kid's pool day to feel like. And your hotel bed to feel like. Ooh, and room service to feel like. Because at Hilton, hospitality feels like. Your cabana's ready. Would you like fresh towels? It matters where you stay. Book now at Hilton.com. Hilton, for this day. Now, another profile in the book tells the story of a guy named Jay Sweet. He quit a job teaching English at Princeton Day School.

31:14Kara Swisher:That's where I went to school, by the way. And bought a one-way ticket to Ecuador. It was the first step towards eventually landing a dream job running the Newport Folk Festival. By 2009, he took it over. The festival was a shell of its former self. He made only$16 ,000 his first year on the job. He was 40 years old with a mortgage and a family. Tell us a little bit about his story, how hard it can be to thrive in the job you love. I constantly quit things like that. I didn't to try. Like I started podcasting in my fifties, right. Not in young age.

31:44Bill Gurley:By the way, Jay is one of the happiest people on the planet right now. Like if you could spend time with him.

31:49Kara Swisher:So talk about his story.

31:51Bill Gurley:He saw me and he said, I saw your presentation. I am that person, but you know, it took him forever to get there. One thing that he struggled with that I see in many people is he loved the music industry and thought he had to be the artist, you know, or in his case, the lyricist. And once he finally recognized that there were these other roles that would allow him to be a part of it is where he found his way towards and then eventually to running Newport. And so I think that's an important thing to realize. You know, if you love basketball, if you love Hollywood, I mean, there's a book called, like about starting in the mailroom because Geffen and Diller and all these people started at the very bottom rung, you know, in what was the mailroom in Hollywood and all succeeded.

32:42Kara Swisher:And so, you know, I started in the mailroom. Do you know that? I started in the mailroom of the Washington Post. Absolutely.

32:48Bill Gurley:This goes back to, to, to a pushback on Scott's thing. Like, I like you can start on the bottom rung. Like it does. There's no, there's no reason you should even have the perception you should start higher than the bottom row. No, you know what it did give me?

33:04Kara Swisher:It gave me perspective and I could watch everything. Like I learned a lot from the mailroom. I learned. That's what they all said. The key thing I learned is that really talented people were very generous and untalented people weren't. Like the ones who are not as good. It was such, from that little perspective of delivering mail, it was really, like it was an eye-opener.

33:24Bill Gurley:Well, So I would love to have had that information. It's always give back. Like starting from the first chance you have the ability to say thank you, be generous and grateful and thankful as much as you possibly can. Because it creates, you know, you could say it's karma. I don't think you have to believe in magical powers. It just gives goodwill. And it spreads goodwill and people appreciate it. And it's not hard to do.

33:54Kara Swisher:Yeah, absolutely. So, speaking of which, every episode we get an expert to send us a question for our guest. Yours comes from Dara Khosr-Shahi, the CEO of Uber. Someone you helped get his job. You're instrumental in getting his job. I feel like I helped him too, but let's listen to it.

34:10Bill Gurley:Bill, one of the principles of your book is to go where the action is. In the tank industry, that's always been San Francisco. Do you think now with Texas coming up, you move to Austin or Miami or even in the autonomous vehicle space, Detroit, could other centers of talent become where the action is as AI and

34:32Kara Swisher:new technology takes over?

34:34Bill Gurley:So not only did you get Darf, the CEO of Uber, to ask a question, but he's clearly read the book, which is awesome.

34:41Kara Swisher:Well, I don't talk to dummies. So talk about that because, you know, San Francisco is kind of back as the center of technology, but he's talking about a broader thing. How do you know where to go, where the action is, and how do you spot talent?

34:55Bill Gurley:So I make the argument that if you are certain that you want to pursue a career in a industry and that industry has an epicenter and you have the wherewithal to get there, you should go. and I think the reason people don't is they have this fallacy that being a big fish in a small pond is a win or they're worried about overt competition but the thing the thing is many of the principles that I have in the book from constant learning to peers and mentors are just 10 to 100 times easier if you're right in the middle of it with everybody else and I mean you live there like you could if you're a young energetic person at Silicon Valley you can schedule something every night where you might meet something or learn something.

35:42Bill Gurley:And there's just that much going on.

35:44Kara Swisher:Is that changing? Not in tech necessarily, but are there epicenters anymore? I think there are.

35:50Bill Gurley:Yeah, I think there are. I mean, fashion and theater in New York, banking New York, songwriting Nashville. Yeah, I think there are. There are industries that don't have it because they're distributed, like sports. It's just naturally distributed. And I think in those cases, you want to use a lot of conferences and virtual meetups to try and help. But there's another thing that happens, and that is luck increases. I use a different word, optionality. Almost everyone you talk through their career path has had one, if not two or three meetings that seem hyper fortunate or maybe even low probability.

36:30Bill Gurley:And you're like, wow, I sure got lucky that person picked me for this or whatever. The chances of that happening if you're in the epicenter are just way higher. The probability coefficient's just higher.

36:44Kara Swisher:Now, speaking of which, Dara happened to be in Seattle when you picked him. Talk a little bit about spotting talent when you're trying to give people those kind of breaks and putting the right people in the right position. It's an important skill for VCs. It's probably your only most important skills.

36:58Bill Gurley:And it's hard. I think most people would say CEO hires fail at least 50 % of the time.

37:04Kara Swisher:Right. So talk about what you look for when you're, are you looking for passionate people?

37:08Bill Gurley:I mean, I think there's a, there's a big difference between a founder maybe and a CEO hire. So I would, um, most of the time, by the time you get to a CEO hire, you need someone who's capable of leadership because you usually by that time have a thousand employees or more. And leadership isn't easy as, as we all know. And there are different people that are skilled at it in different ways. So that's one thing you need. Josh Wolf has this great saying chips on shoulders, put chips in pockets and, you know, finding people that still have something to prove in one way or another. I think Barry Diller has been very open about the conversations he had with Dara about taking that job and encouraging Dara to take that job.

37:52And I think in there was

37:54Bill Gurley:a sense that he felt Dara was capable of something bigger than what he was working on at Expedia and encouraged him to go chase it. And having that determinism is certainly helpful. And I think that's helpful at the founder level.

38:10Kara Swisher:That was a good choice, by the way.

38:12Bill Gurley:Well, there's another thing that dar was was great at which was um he is he is a diplomat writ large and there was a lot of issues with the company at the time as you're aware and he he was able to slowly one by one take care of each of those which was imperative for the company right and not easy i mean look at the london situation it was remarkably bad um and hard and he went in and and made that better

38:42Kara Swisher:Right. Well, I mean, his greatest qualification is he wasn't an asshole. But the threat of AI-driven job losses.

38:47Bill Gurley:Yes.

38:48Kara Swisher:You said the best way to avoid losing your job is to become the most AI-enabled version of yourself. That works on an individual level. It doesn't necessarily address the problem at scale. So you're writing a book about building a career you love when people are deeply worried about their careers. Unfortunately, Sam Altman just made a stupid remark about how hard it is to train a human compared to data center energy. I'm not sure why he did that. But he needs to not talk so much. But talk about that because there is—

39:16Bill Gurley:He's usually pretty good. I know. That was bad. That was like, oh, my God. That's the plot of the matrix.

39:23Kara Swisher:He talks too much. But the problem of AI is worrying people that they can't do their— if you're talking about do your passion and you have AI, which is the latest of many in history, bearing down on people, how do you square that circle?

39:38Bill Gurley:Well, I think that you bring up a good point. Are you looking at it from a bottom-up or a top-down perspective? Either way. And from a top-down perspective, it does look scary and threatening. And I've talked to people, I've talked to lawyers that run large firms that have already drastically reduced the number of paralegals. So it's not theoretical at this point. It's real. So, you know, Stephen Covey talks about this circle of influence, like know what you can control and what you can't control and worry about what you can control. I don't know that there's anything we can do. And I don't mean to be defeatist by that, but, you know, the country used to be 98 % agriculturally employed and it's 2 % now.

40:25Bill Gurley:So change has happened. This is new and fast and it's attacking jobs that haven't been attacked in the past. And so it's creating a lot of anxiety, but I don't know that we can put it back in the bottle. I don't know that I'm highly skeptical is what I would say that the government could pass some kind of regulation that would make it all better. Even retraining. I can't imagine the U.S. government having a wildly successful retraining program over the next five years. I don't imagine that. And so if it's out of your control, I just would say, you know, understand what it's capable of in your industry and be the, what I said, be the most AI aware person in your job.

41:08Bill Gurley:And you're going to then be the last person that they want to get rid of. They're going to be very curious why you're able to harness this power and how you're able to do it. And it ties in with continuous learning. Like if this technology has the ability to impact your industry, you need to know about it. And, you know, there are other tools that have come along, you know, along the way, you know, a modern farmer has tractors and is using drones now and all kinds of stuff. And they didn't in the past. And so I don't even know that like trying to hide it or put it away. I don't think it would work.

41:42Bill Gurley:So but I do think here's an interesting paradox that I would have for you. I think a lot of the people that go through that college conveyor belt that are chasing a safe job that end up working as a widget or a cog in an industry they may not love, I think they are ripe for disruption. And if you have the wherewithal, and I'm not saying this is easy, to craft your own career path and to really make it bespoke, and that's what I would encourage with this book. I think you view AI as jet fuel, as something that's going to make what you're capable of even better. Like if you're like the truth of the matter is you could never learn faster, quicker, more thoroughly than any time in history than right now.

42:31Bill Gurley:And so if you're constantly learning, honing, if you're figuring out how to get AI to help you be more productive, you're going to have an even better chance of winning. And so I just think it's an interesting paradox that some people would view it as, oh, this is a superpower. I'm going to be even better. And some people view it as, oh, my God, I'm dead.

42:53Kara Swisher:Well, one of the things, the safest jobs are the ones that, like lawyers, software engineers, right? Those were always considered the safer choices, right? Yeah, you are correct. Which is interesting.

43:05Bill Gurley:And so maybe I can't solve the entire AI unemployment problem, but if you were put in a safe job that you don't truly love, I would encourage you to consider this alternate door that I'm representing to maybe find something you're passionate about and get away from that risk. Because I do think the people that are most at risk are the ones that are sitting idly in the job and don't really have a why or a purpose for it.

43:36Kara Swisher:We'll be back in a minute.

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44:27Bill Gurley:The first is mental clutter. The second is physical clutter. One requires meditating. The other requires Stanley Steamer. Start with what you can control. Then go outside. It's cheaper than a spa. No appointment required. Book your deep clean now at stanleysteamer.com.

44:47Kara Swisher:Everything feels a bit uncertain right now. A few months ago, you never would have expected eggs being factored into your monthly budget. New sources of stress equal more opportunities for breakouts to strike. Luckily, Mighty Patch Original shrinks the look of pimples in just one use. We'd say that's a pretty good deal. Shop Mighty Patch at all major retailers. Let's talk a little bit about Silicon Valley and what's happening right now, because you have left sort of as a big leader there. But, you know, politics has now sort of entered the picture in a really significant way. It's unavoidable, really, pretty much.

45:25Kara Swisher:I wouldn't even know what your politics were. I didn't know what Elon's were. I didn't know what any of them were, right? I really didn't. Someone said, what were they like? I was like, I have no libertarian light.

45:35Bill Gurley:It didn't come up.

45:36Kara Swisher:It didn't come up. And they, in fact, disdained it. And the first time I had Bill Gates to the Washington Post, he's like, I don't have lobbyists. I never come here. You know, it was interesting. You retired from venture capital. you're considering starting a public policy institute you're calling p3 for purpose progress and prosperity yeah um i'd love to know what that means um you're going to obviously try to tackle big policy issues like u.s china u.s health care system regulatory capture talk a little bit about

46:03Bill Gurley:what that means yeah and by the way you know i gave this talk that i was originally going to give at your conference i gave it a year later at all in because unfortunately my mother passed away about regulatory capture.

46:17Kara Swisher:Let me note that. It's a phenomenon for people who don't know where regulators end up being captured by industry leaders, and so regulators write laws that benefit the largest and most powerful corporations in history. The solutions you suggested was overturning Citizens United, mandating transparency, political fundraising, get rid of a revolving door between government and lobbying. Our versions of regulation, talk a little bit about that.

46:42Bill Gurley:Yeah, and by the way, but I was going to just say that the punchline of that talk, it was called 2 ,851 miles. That was the distance from Silicon Valley. And I said, you know, the reason that Silicon Valley works is because it's so far away. And yet after that, that has changed dramatically after that talk. And they're so close.

47:04Kara Swisher:So talk about how that's changed to your personal political philosophy and what you're trying to do here with these three Ps.

47:09Bill Gurley:Well, what I would like to do is just focus on individual issues. I don't have an interest of getting into particular candidates or particular parties. And so like, I'd love to go, like one idea we have that I may work on with some schools is to create an index of regulatory capture of all the countries around the world. And because if you have ones that have less and some that have a lot more, you can ask what kind of policies do they have that allow for that. That'd be an example. I'm really blown away by the people that helped shift the mindset on nuclear energy over the past five years. It went from being considered bad to good in a very short window of time.

47:55Bill Gurley:And there were people like Steve Pinker, the Collison brothers, Josh Wolfe, and Elon that were saying, that had the guts, I would say, to come out and say, no, we should be celebrating this technology. We shouldn't be vilifying it. They were kind of lone wolves when they were doing that, but they were able to move. And so I view that as a massive win. And I don't know if you can find enough of those. There's another one that I consider a big win. There's a gentleman I've been backing that helped push through financial literacy as a required course in high school. He's got 20 states to put that on the ballot.

48:35Bill Gurley:I think that's good. These credit card companies chew these kids up and they have no awareness of this type of stuff coming at them.

48:43Kara Swisher:What does three Ps mean? Purpose, progress, prosperity?

48:48Bill Gurley:It's something that spoke to me. Matt Ridley's book, Rational Optimist, is one of my favorite where he talks about what's driven and prosperity around the globe. And, um, and yeah, just having the biggest impact you can possibly have, like, and, um, you know, I, I'm a big fan of this, uh, this, uh, non-primary voting that's moved into a lot of cities and States. I think that tends to keep radical candidates out on both sides and gives, you know, we, we have that in Austin for the mayor race. and you end up with a centrist Democrat instead of a far-left Democrat. And it can work on both sides. You can keep, you know, because more of the citizenry is involved in the actual vote that matters, the last vote, which doesn't happen if you have traditional primaries.

49:41Kara Swisher:FYI, though, Matt Ridley is a libertarian with a staunch supporter of Brexit. May not have been right about that necessarily.

49:47Bill Gurley:May not. But I love his book that rational optimism is covered about like a thousand years prior to now.

49:55Kara Swisher:Yes, I got that. But one of the things that is happening is you're trying to be a solutions-based person, presumably. You've always been that way. But President Trump has changed the calculus for the tech industry, which most people were solution-based, I would say. Leaders used to be, I would say, apolitical, again, maybe libertarian-like, kind of liberal, tolerant on the social issues, everything else. They tried to stay out of politics, as was always my experience. They have now publicly embraced Trump in ways that are so awkward. Some of them, I would put them into camps. Okay, I'm going to give him a statue because he likes statues.

50:29Kara Swisher:Oh, I really like this stuff, actually. This is what I'm like. And others are, you know, shareholder value. You know, he's trying to insert himself in the Netflix series. He's trying to insert himself everywhere. It feels very Putin-esque to me, you know, in terms of what Silicon Valley used to hate, right? Right. And then the ice killings, I think, have put pressure on some of these tech companies when they're sitting there in the front row of the things. Talk about what happens to the tech industry, because it seems like they're Trump captured.

50:58Bill Gurley:Yeah. As I said in my original speech, like, I hate it. Like, I always felt like Silicon Valley was this place where everyone believed that anyone could do anything that was possible, you know. And if being connected in Washington is part of the requirement of being successful, it's not the type of place where two young people in a PowerPoint can get together and start a company that will do really well because you'll need more. So I don't like it as someone who wandered into Silicon Valley with very idyllic notions and thought of it as this kind of corporate version of American Idol. I don't like that element of it.

51:47Kara Swisher:Where does it go next? Because he's inserting himself.

51:50Bill Gurley:I'm not a fan of backing weapons companies as venture capitalists. And look, I'm out now. So like I'm not. No, I get it.

51:57Kara Swisher:But where does it go? You're a smart guy. Where is it? Because someone asked me this the other day and I'm like, I don't know how they're going to get themselves back.

52:05Bill Gurley:Well, two things I would say about that. One, venture has gotten more industrialized and it got more competitive every year I was in it. But now, because, you know, several people have decided to get really big, whether it's Andreessen or Thrive or Sequoia or whoever, it just becomes more like a big PE shop. And of course, you're going to have government relations. And of course, you're going to have lawyers and media and PR people like you just you're not going to be that big and not hire people in those roles and do everything you can to win. And so part of it may be that the industry grew up in a way that maybe you and I might not like, but it may be happening.

52:47Kara Swisher:But what has to happen? Because I've never seen a group of people that have gone from, we love you. The imagery now is very billionaire, scary billionaire, evil billionaire, right? It's not a good look for tech, which can be, as you know, I love tech, but at the same time, lots of anger everywhere.

53:06Bill Gurley:Well, I think a lot of people are worried about that. I mean, even on the famous All In podcast, I think Freebird is concerned about this writ large, that it encourages behavior that could become anti-capitalist and therefore it's very dangerous. And I think you've got to be careful what you say. I do think Anthropic particularly, but even OpenAI, are begging for regulation. Yeah, yeah, yeah.

53:35Kara Swisher:I think Anthropic is going to be enormous. That's my feeling, because I think they're the next version of Silicon Valley.

53:40Bill Gurley:And they've been spending money, you know, not just at a national level, but at a state level, trying to write all these laws. And I really, I don't love that, but that is what's happening out there.

53:52Kara Swisher:Yeah, I mean, I think it's going to be a negative. It's definitely going to be, I mean, you couldn't say all the good things you want about Elon before, but Elon now is not good for tech. It's just not, but it's good for money making and that's very different. But coming back to regulatory capsule, as I mentioned earlier, your solutions like overturning Citizens United and.

54:10Bill Gurley:Well, I think that would be big. I don't know if it's possible, but it would be huge.

54:14Kara Swisher:I actually just did a really interesting interview with Larry Lessig, and there's a case that will basically kneecap Citizens United, and that's good enough. I'm familiar with this.

54:22Bill Gurley:This is in Maine.

54:23Kara Swisher:Yeah, exactly. But does that call for more regulation? Take it from the other side. Obviously, tech hasn't been particularly regulated. Talk about the paradox of tech needing some guardrails.

54:35Bill Gurley:The problem is that in almost every industry in the U.S. where there's heavy regulation, you've ended up with less diversity, fewer companies, more of an oligopoly. I mean, look at it in plane building. We're down to just like one company, basically. Yeah. And when you do that, you lose innovation. You lose disruption. You lose all the things we watch happen in Silicon Valley. And so I'm—

55:03Kara Swisher:Is that the direction tech feels headed in? Because it feels rather wealthy.

55:08Bill Gurley:Oh, I mean, I think for certain reason Anthropic and OpenAI are begging for regulation is so that they can write rules that make it harder for startups, especially open source models, to be competitive with them, which I think is very rational for them to do, but I don't think it's good for society.

55:25Kara Swisher:So just a couple more questions. After the Supreme Court struck down Trump's use of International Emergency Economic Powers Act to enact tariffs. The administration announced 15 % tariffs across the board. Also, it would begin official inquiries into unfair trade priorities, including discrimination against U.S. tech companies, for example, with European regulations on the block, I would assume. You've spoken out against the tariffs, so have I, and you more against tech relations in general. I would like a few. What do you make of this approach of this punishing EU for writing regulations that affect American tech?

55:55Bill Gurley:By the way, I'm not against uncaptured regulation. There's just not much of it. But, but, but on the tariff thing, look, I, you know, and by the way, you've spent way more time in DC and I'm just getting started. So I say all this with a lot of humility and naivete, but the, the abuse of the executive power, which has happened on both sides of the aisle for many, many presidencies. now, I think it's not good. You know, I don't think it's good. And so I think it's good that the Supreme Court pushes back on any of the branches that tries to assume too much power relative to one of the others.

56:37Kara Swisher:Do you think it will be effective, given that Unitary Executive is one of Tech's favorite things, isn't it?

56:42Bill Gurley:I don't know. I don't know. I don't know. Do you think it'll be effective?

56:45Kara Swisher:It's been turbocharged with Trump in this case.

56:48Bill Gurley:Do you think the decision will be effective?

56:50Kara Swisher:I don't know. I don't know because a lot of people, I think we've learned that there's not so much laws as there are, I think I'll do this or not, and this person's just rolled through it because there isn't something in his way. And so we always had agreements that weren't necessarily, you know, it's happened before in our history, but no one's ran through stuff as much as this. I do think there's a risk that people aren't considering, which is that if we are undiplomatic with our partners around

57:25Bill Gurley:the globe, that it will be more easier for them to rationalize agreements with China. That's correct. China is, I just spent some time there in August, is hitting on many, many cylinders. I won't say all because they do have some issues, but they've figured out how to be hyper competitive, especially in a lot of important new technologies, which would include solar, EVs, phones. They're getting there in chips. They're there in energy, which is pretty wild. They're increasing their energy production way fast. And so if you alienate the rest of the world, I think there's a chance. I think this could even happen with AI models where there's a fence around America and China's serving the rest of the world.

58:14Kara Swisher:Yeah, I think in everything, including healthcare, too. I mean, I was just talking to mRNA technologists, all of whom are moving to Canada. And they said, we're going to have to be begging China for a vaccine during the next pandemic. And obviously cars and everything else. So you're absolutely right. So let's finish up. You're known for being a voice of warning in the industry. When I last interviewed you, I called you the worrywart of Silicon Valley.

58:38Bill Gurley:That's fair.

58:38Kara Swisher:Let me read two quotes of yours from recent interviews you gave. They highlight your reflective nature. And one is, capitalism and democracy corrupt each other over time. And the other question you asked, does America really benefit by the fact that the MAG-7 have$3 trillion market caps? You asked it earnestly. Your answer is essentially maybe it doesn't. I know you, so it's not surprising to me, but it's probably surprising to hear a different voice from Silicon Valley that's talking about, is this the best route we should go? When you talk about these war reward things, do we need more democracy or more capitalism?

59:10Kara Swisher:Or when you talk about these MAG-7 having these caps, I think it's extraordinarily dangerous.

59:16Bill Gurley:So I think there's a lot of people that believe that capitalism is the best way to distribute work and to balance things, going way back to the philosophers that wrote in the 1700s and 1800s. And I think for the most part, that's been true. I think people confuse how we vote for candidates with the system of how your corporations work. And so capitalism, you can have capitalism within a democracy, but you can also have it within a dictatorship, which I think is what's happening in China. And one of, but one of the checks and balances against it is always, you know, there's a notion in academics called pure competition.

1:00:02Bill Gurley:And in pure competition, marginal costs, you know, marginal price eventually reaches marginal costs and there's no excess profit for the corporation. And that's because competition has whittled it away. And I think many economists would argue that's the ideal state where competition leads to lower prices, more prosperity. Everything works better as a result. If you have really big market cap companies, maybe they're monopolies, right? And they're not, for whatever reason, there's not this opportunity for competition to whittle away at that excess profit. And so it's just a question I had. It seems pretty apparent to me that the Chinese government doesn't care for that.

1:00:49Bill Gurley:And so that caused me to reflect on, well, is it good or not? There aren't a lot of employees. There's a lot of wealth that's created. And then that wealth could get spent, which does increase GDP. I think those are the arguments why it's okay. I think the questions are, if those industries were more competitive, would those numbers be lower? Would prices be lower? Would you have more companies with more employment, necessarily?

1:01:17Kara Swisher:And more innovation, presumably.

1:01:19Bill Gurley:Yes, possibly more innovation. And that ties into regulatory capture, because in some cases, that can be what might lock in a monopolist.

1:01:29Kara Swisher:Right. So, you know, a lot of young people, they've been through a lot, right? You're writing something hopeful for them. You can follow your bliss. You can do this. You can do that. What would you say a young person comes to you and says, I just, this fucking world, it looks like the billionaires are running everything. AI is going to kill me. I don't have a lot of choices. My prospects are lower. I can't buy a house. What would you say to that person? How would you reassure them that these things that feel so heavy, right, that seven people run the world, they're kind of jerks. um what would you be your three things very briefly would tell them one thing i would do is

1:02:07Bill Gurley:just tell them to take a really deep breath i don't think that that attacking your life with the weight of severe anxiety is going to be very helpful um and even if you want to change the world i don't know that it's going to be helpful if you're paralyzed um the second thing i would say is one of the reasons I put so many stories in the book, if I hand someone a book that's a textbook and many of the career, the better books in the career space are read more like a textbook. It's not, it's not necessarily believable, right? It's just a bunch of words and hearing about other people that have started on the bottom rung and made it can be, I believe, and the reason the book structured that way is I think it can be inspiring.

1:02:55Bill Gurley:Like it can tell you, Hey, and maybe you see something in one of those stories that fits you particularly well. And then it's impactful and then I would, and I can't do this with everybody, I would just spend more time with the individual. I think you can tease apart what people really love and try and find it. And I would love to be a part of that journey. I was helping a student last week. It's fun to talk to them about what it may be. And I think they've been told by so many well-intentioned, I always want to make that point, people to chase these safe jobs. And I can see why that, if you don't have any interest in those things and being pushed towards that is just not inspiring and not, doesn't give you the sense that you're in control.

1:03:48Bill Gurley:And one of the takeaways from the book is, I use the phrase, be a candidate of one. How do you build your career path such that you look completely different from everybody else, which I believe is totally doable.

1:04:02Kara Swisher:Yeah, that's absolutely true. You know, it's also, I just recently taught at University of Michigan, largely to spend time with my second son. But one of the things I was struck by is how great the kids are. I have to say, the kids are all right. The adults, not so much. That's how I feel.

1:04:17Bill Gurley:Well, and I, you know, I'm thrilled that you called the book hopeful. There's a lot of negativity out there. There is nothing in this book that's meant to dwell on problems. It's all about what's possible. And I hope I can have a positive, hopeful impact on as many people as possible.

1:04:37Kara Swisher:So now you're not the worrywart, but that's because they're also acting so badly. Anyway, Bill, thank you so much. It's great talking to you.

1:04:43Bill Gurley:Appreciate it.

1:04:48Kara Swisher:Today's show was produced by Christian Castro-Sel, Michelle Loy, Catherine Millsop, Megan Burney, and Kaylin Lynch. Nishat Kerwa is Vox Media's executive producer of podcasts. Special thanks to Bradley Sylvester. Our engineers are Fernando Arruda and Rick Kwan, and our theme music is by Trackademics. If you're already following the show, you get to be the CEO of Uber. If not, you're fired as the CEO of Uber. Go wherever you listen to podcasts, search for On with Kara Swisher, and hit follow. Thanks for listening to On with Kara Swisher from Podium Media, New York Magazine, the Vox Media Podcast Network, and us.

1:05:22Kara Swisher:We'll be back on Monday with more.

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