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

I learned a lot from the mailroom.

The key thing I learned is that really talented people were very generous and untalented people weren't. Hi, everyone, from New York Magazine and the Vox Media Podcast Network. This is On with Kara Swisher, and I'm Kara Swisher. My guest today is famed venture capitalist and author of Running Down a Dream: How to Thrive in a Career You Actually Love, Bill Gurley. Bill was a top-ranked research analyst on Wall Street. When I met him, he covered the PC industry. He worked as the lead analyst on the Amazon IPO before decamping for Silicon Valley. There, he became a general partner at Benchmark Capital, a celebrated VC firm there, known for early-stage investing and very tall venture capitalists.

Bill was an investor in companies like Grubhub, Nextdoor, OpenTable, Stitch Fix, Zillow, and most notably Uber. After a long and successful career, he's retired from venture capital and written a personal development book about finding the career you actually love. I was surprised when I got it, when he wrote me. I thought I was in a beef with Bill Gurley because I'm in a beef with all the Silicon Valley people, but I wasn't because Bill is thoughtful. He's a great debater. Even when we don't agree with him, he's always been a gentleman. And he actually reads and is an intellectual in many ways. He's always been that way. And so I'm excited to talk to him. He's also the polar opposite of what Scott preaches on Pivot, so that's a relief.

So I'm curious to hear Bill explain why it's actually important to do what you love. And of course, I'll ask him about President Trump and politics because now it's inescapably intertwined with everything in American life, especially the tech industry. Our expert question comes from Dara Khosrowshahi, the CEO of Uber. So stick around. Support for this show comes from Kohler Health. The body sends you answers to important questions every day. How's your digestion? Are you drinking enough water? But most of us don't know how to interpret them. For over 150 years, Kohler has redefined innovation and craftsmanship in the bathroom. Now Kohler Health is reimagining its role in personal health with Kore.

Kore is an attachment that fits discreetly on your toilet. Learn more at KohlerHealth.com and use the code CARA1YEAR for a free annual app membership when you purchase Kore. Support for this show comes from Odoo. Running a business shouldn't feel like surviving a software group project. One app for accounting, another for inventory, another for sales, and somehow none of them ever talk to each other. That's where Odoo comes in, an all-in-one business management software that brings every part of your business together, from sales and accounting to inventory and marketing, all in one powerful platform. No messy integrations, no bouncing between tabs, and best of all, no spreadsheets. Stop managing software and start managing your business with one unified system.

Try it today for free at odoo.com/Cara. That's O-D-O-O.com/Cara. Hey, quick thing before we get into it. I'm doing a live taping in Washington, D.C. on July 16th at the Johns Hopkins University Bloomberg Center. My guest is Gina Raimondo, the 40th Secretary of Commerce and the 75th Governor of Rhode Island and someone who has a lot to say about AI and what it's actually doing to the American economy. She may also run for president, so we should listen to what she has to say. It should be a good one. You can be in the room. Head to voxmedia.com/KaraSwisherLive to register. Spots are limited. We always sell out. The link is in the show notes. Bill Gurley, thanks for coming on On.

Thanks for having me on, Cara.

I'm going to get into a bunch of stuff, but let's start with you. Within Silicon Valley, you're incredibly well-known as a renowned former VC. I met you when you were investing.

I was a stock analyst, and then I spent a year and a half at Hummer Winblad, and then I went to Benchmark. I think it was probably back when I was a stock analyst.

I did. I met you when Mary Meeker was also a stock analyst and you both became investors. And then I think I ran into you again at Hummer. And then I think I wrote the story when you went to Benchmark and then you invested in eBay. But fans of the show, people who know you actually know you from Super Pumped as the fictionalized version of you played by Kyle Chandler. Tell people who don't know who you are, who you are.

I grew up in Texas. My father was a very early employee at NASA, which was, I think, quite influential on me that he did that and had such a ride. I was an end-of-the-bench D1 basketball player that didn't get very many minutes. I got a lot of experiences and became a computer scientist, worked at Compaq, which you'll remember, but most people won't. Um, as an engineer for two years and then business school, then Wall Street analyst for three years in New York City. And then a year with Frank Quattrone, he's the one that took me out to Silicon Valley.

Famous banker, famous banker. He got in a bit of trouble, but also very famous, important banker in early, especially in early days of the Internet.

Yeah, we kind of historically won the mandate for the Amazon IPO, which was fun, over Morgan and Goldman. And then I got into venture, which is really what I wanted to do and was always my dream job and loved it, loved it, loved it, and spent 25 years doing it. And eventually got to the point where I realized it was time to kind of hang up my boots and let the next generation take over. I think the Valley and the venture capital are bent towards youth, which is awesome when you get in at 30, but I think it's harder to keep up as you get older.

Well, they don't leave. It's very much like Congress. They actually do stick around the basket, so to speak.

But I'm not sure that's a good idea. It's not a good idea.

It's not. That's why I'm only getting you to say, because my listenership has broadened quite a bit from tech. And just for people that don't know, you're 6'8". Correct. All the Benchmark people—I remember sitting across, tiny me across.

They were. I think the new guard's not noticeably tall at all.

No, not as tall, no. But you're 6'8", hence the basketball thing, but you're being very polite about yourself. But, Bill, you were sort of the hot ticket item of venture capitalists. There's always a hot person at the time, and you were when I first got there in the '90s. So you've decided to hang up your spurs, whatever Texas analogy you want to make. Spurs, boots, yeah. Spurs, whatever. Your stated reason for writing this blog is, quote, 'to give everyone as much permission and as much confidence they need to pursue a career they love.' Talk about why you decided to do this and who or what is stopping people from pursuing careers they love.

So for the better part of two decades, I wrote what was a newsletter. It actually started as a fax and became a blog post called Above the Crowd, a reference to the hype. And I would synthesize ideas that came to me. So about new industries that were breaking out, marketplaces, things I was seeing in the venture world. And in the background while I was doing that, you know, some type of digital note-taking, you know, whether it's in Microsoft Word or now Notion, you know, moved through Quip, but I would start ideas—and you probably do this too as a writer—like, I would start ideas, they didn't all finish, right? And so there were little pockets of stuff, and if I added to them, sometimes they'd come to life, and

There was a point in my career where I was reading a lot of biographies, and I read this third biography and noticed these through lines with two others. Who were they?

Yeah, it's a weird array of people. It was Bob Dylan, Bobby Knight, and Danny Meyer, the New York restaurateur.

Bobby Knight, the college basketball?

The college basketball. They all started with intentionality on the very bottom rung, which was interesting. And they all rose to the top of their industry. And they all used a lot of very similar techniques to get where they were going. And that led to me, just as I would analyze how an internet marketplace business is evolving, I wrote down some themes. And then I got invited about eight years ago to give a talk at the University of Texas. And I asked them, "Do you mind if I use this?" And they said, "Great." So I kind of turned it into a presentation and gave it. And then they uploaded it to the internet, and a few different people took notice. The probably most noticeable, and the thing that kind of woke me up that it could be a book, was James Clear, the author of Atomic Habits.

He posted it on his website. Right.

So then a few different people kind of poked me and told me, you know, "You should go do this." One of those was Tony Fadell, who's become a close personal friend. And Tony wrote this book, Build. You've probably—you're probably aware.

And Tony told me it's the best thing he had ever done. And this is the guy that invented the iPod, ran engineering for the iPhone, and launched Nest. And you're like, "And that's the best thing?" But he just talked about how fulfilling it was. And so he pushed me to do it. And when I was, in my brain, moving past VC and thought about, "Hey, if I ever wrote a book, what would it be about?" A lot of people wanted me to write a VC book or an investing book, and none of those really—I didn't have a calling to go do that. How many people would read a book about how to be a good VC anyway? Not that big an audience. So just thinking about it from an impact standpoint, I really wanted to do this.

So you wanted a bigger impact. You're meaning to touch more people and what stops them from pursuing the careers they love. So as you began to collect all these notes, what is stopping people from pursuing them?

Yeah. You—you asked that earlier. Let me get to it. Um, there was a Gallup poll in 2023 that like 53% of people are disengaged at work, and that's not great. We've all heard about quiet quitting. This is pre-AI, by the way. So there seems to me to be somewhat of a problem out there, and that people aren't landing where—where they're passionate about what they're doing. The second thing that I think has happened and, um, you know, I don't think it's anyone's fault, but I think we've turned the college matriculation process into this pressure cooker. And other people have mentioned this. Jonathan Haidt in Coddling of the American Mind called it the resume arms race. But somewhere starting around sixth grade—and you're a parent, I think you felt these pressures, right?

You start worrying about getting your child into college. I have.

I resist. I never was like that, but go ahead. I was different.

No, I'm just saying you're aware that these societal pressures are there totally, and so people start, you know, worrying about cello lessons and chess lessons and volunteer work, and the kids today are programmed from a time perspective way more than than our generation was growing up. We just weren't scheduled that often. And what some people believe, and and I think is consistent both with with the advice in my book but the research we did, is that that leads to a lack of kind of play and discovery. They're not allowed to just wander around and figure out what they're fascinated by. And another weird thing happened. Colleges used to say you can't pick your major until the end of your sophomore year.

Now they make kids apply to majors when they apply to college in a lot of schools. They do indeed. You've brought that forward like three years.

One of the main takeaways, obviously, is the old "follow your passion." The word passion or "passion" appears over 50 times in your book. Oddly enough, I agree with that. I love what I do. I love, like, I can't explain how much I love what I do. But according to Scott Galloway, my Pivot co-host, he said, if someone tells you to follow your passion, it means they're already rich. You most certainly are. I'm not doing so bad. So is he. According to Scott, making your passion a career will spoil it, turning it into a thing you do for money, not love. So I think he's wrong. I want you to tell me why he's wrong so I can underscore it with him.

Well, one of the things we did, and the book's divided into profiles and principles, so it's stories of success.

But almost every single one of these people started on the bottom rung. My favorite story from that perspective is Jen Atkin, who's probably the most famous hairstylist of all time. But she moved to L.A. with $200 in her pocket 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. I think Palmer Luckey said it the other day.

I'm going to take his advice, but go ahead.

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 passion. If winning is your passion, it would be logical to do whatever you're most skilled 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.

Right, absolutely.

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 a real passion for.

For economic reasons.

Right. So let's dive into a few of the six principles you lay out in the book to achieve a flourishing, purpose-filled career. 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?

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 belt 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. So one, one thing is just to give your permission—yourself permission. That's not failure if you want to go try something else.

Um, 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, at this 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? Yeah, 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?' 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.

You also have to have a boss 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 think this, 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.

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.' 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, and so it was this push with both support, but responsibility and, you know, as a parent, and I've seen this, you want to push them towards the safe job with the money. And it's just an instinct that people have.

Well, they often want to do it. I just had a discussion with my oldest son about it. 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 an odd thing. But speaking of Angela Duckworth, who you mentioned, when I interviewed you in 2016, you brought up her book, Grit. I don't know if you remember that. This is 10 years ago, almost. Yeah. 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 overlooked part of finding your passion or fascination. In other words, purpose matters. What is your "why"? And talk to me how you figured it out and why that is important, why the "why" is important, I guess.

Well, the second principle in 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" and 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. 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.

So talk about your "why." Talk about how did you figure out what that was?

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

Both. Try venture capital. What was your "why"? Why did you decide that?

When I was an engineer at Compaq 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, a highly-ranked technical person here. And that was an easy no for me, you know, for whatever reason. And, and I'm, I'm thankful that I had that kind of ability to think forward like that. Bezos had something similar, his 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?"

It's kind of similar.

I was at The Washington Post, and I looked around and I said, "I don't want to be anybody here." Right. Yeah, exactly. So I need to go.

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

Let me press you. Does that require—like, I finished up this longevity thing, and one of the speeches I used was, was Jobs's famous speech to Stanford, Steve Jobs's, and it was about not having regrets. And if you say, "No," when you wake up every morning, you need to get out. Like, right, he was using death as the way, you know. 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?

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 time. It's not part of their mental framework. And I don't necessarily think filling their brain with anxiety is necessarily a positive.

You know, actually, death acceptance makes you live longer versus death avoidance.

And I think Jobs was onto something.

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.

Right, the things we don't do. So when you left Compaq, what was the why? 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?

Well, 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. I had started reading the tech magazines that you were familiar with back in the day, PC Magazine and Byte, and

What was the other? InfoWorld? 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, Doerr was on the board, so I had a sense that there was this venture thing there. But I didn't really know how to get at it.

It's John Doerr. Yes.

And it was interesting to me, but I didn't know how to get at it.

So business school was the way it got you to your why.

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.

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 manservant. 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 a great group of peers. You illustrate that with a profile of Jimmy Donaldson, also known as MrBeast. Even though you push companies to formalize these principles, none of them ever did it. 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.

Yeah. So what I'm talking about, and it's better exemplified in all the stories in the book and the MrBeast ones. Let's just do the MrBeast 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. 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 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.

So why are so many people unwilling to do it?

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. And then the second thing is people get overly concerned about sharing proprietary advice. And I, personally—and others have said this, but I think Altman said it recently—I think ideas are a dime a dozen.

You think you have a proprietary idea, but there are other people that have the same information.

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.'

And you build trust, and you build better—you build 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.

We'll be back in a minute. Support for this show comes from Kohler Health. What if the most routine part of your morning could give you valuable insights about your health? Kohler defined the modern bathroom. It's where your daily routine already happens. Now it's bringing health tracking into that same space. That means automatic insights into your hydration, gut health, and irregularities that often signal a flare-up. How? Kohler Health's Dakota slips seamlessly onto your toilet and passively captures your everyday biometrics. Without any manual logging, you'll see hydration and digestion patterns and even be alerted about the presence of blood in the Kohler Health app, giving you a clear picture of your internal health and helping you build habits that truly work for your body.

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With Cohere, you don't have to give up control to gain capability. You can have both. Cohere started seven years ago with a bold mission: scale enterprise intelligence without sacrificing sovereignty. Their solution? AI leaves you in charge of your data and infrastructure, allowing you to maintain your competitive edge. It's designed for enterprises, governments, and organizations that refuse to give up control in pursuit of innovation. From frontier models to out-of-the-box tools, Cohere gives you everything you need to build and deploy secure, scalable AI that drives growth and delivers results. Their platform is designed around your business with models that can be customized and trained on your proprietary data so the solution is uniquely yours.

And control doesn't stop at customization. Cohere is built with multi-layered protections, access, and industry-certified security standards that help safeguard your data while supporting privacy compliance and other requirements. As AI continues to transform every industry, Cohere gives you the power to put it to work today on your terms. Take charge of your AI with Cohere. To learn more, visit Cohere.com/Vox. Support for this show comes from Cohere. As AI advances, one thing matters more than ever: staying in control. Most AI comes with strings attached, like sharing your data and infrastructure or compromising your independence. With Cohere, you don't have to give up control to gain capability.

You can have both. Cohere started seven years ago with a bold mission: scale enterprise intelligence without sacrificing sovereignty. Their solution? AI leaves you in charge of your data and infrastructure, allowing you to maintain your competitive edge. It's designed for enterprises, governments, and organizations that refuse to give up control in pursuit of innovation. From frontier models to out-of-the-box tools, Cohere gives you everything you need to build and deploy secure, scalable AI that drives growth and delivers results. Their platform is designed around your business with models that can be customized and trained on your proprietary data so the solution is uniquely yours. And control doesn't stop at customization.

Cohere is built with multi-layered protections, access, and industry-certified security standards that help safeguard your data while supporting privacy compliance and other requirements. As AI continues to transform every industry, Cohere gives you the power to put it to work today on your terms. Take charge of your AI with Cohere. To learn more, visit cohere.com/box. 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—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. Um, tell us a little bit about his story. His is how hard it can be to thrive in the job you love. I constantly quit things like that. I didn't dare to try. Like, I started podcasting in my fifties, right? Not at a young age.

By the way, Jay is one of the happiest people on the planet right now. Yes. Like, if you could just spend time with him.

So talk about his story. Yeah.

He saw me and he said, "I saw your presentation. I am that person." But 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, 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, that 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 *The Mailroom* about starting in the mailroom, because Geffen and Diller and all these people started at the very bottom rung in what was the mailroom in Hollywood and all succeeded.

You know, I started in the mailroom. Do you know that?

What?

I started in the mailroom of *The Washington Post*. Absolutely.

This goes back to, to, to a pushback on Scott's thing. Like, like you can start on the bottom rung. Like, there's no—there's no reason you should even have the perception you should start higher than the bottom.

No, you know what it did give me? 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 for me.

Well, that fits nicely with my sixth principle, so I would love to have had that information. It's always give back, like starting from the very beginning, from the first chance you have the ability to say thank you, be generous and grateful and thankful, you know, as much as you possibly can, because it creates, you know, you can 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.

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

Bill, one of the principles of your book is to go where the action is. In the tech 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 new technology takes over?

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

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?

So I make the argument that if you are certain that you want to pursue a career in an 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 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 in Silicon Valley, you can schedule something every night where you might meet someone or learn something.

And there's just that much going on.

Is that changing? Not in tech necessarily, but are there epicenters anymore? I think there are.

I mean, fashion and theater in New York, banking in 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 to about their career path has had one, if not two or three meetings that seem hyper fortunate or maybe even low probability. 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.

Like, the probability coefficient's just higher.

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 single most important skill.

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

Right. So talk about what you look for when you're looking for passionate people.

I mean, I think there's a big difference between a founder maybe and a CEO hire. So 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 we all know. And there are different people that are skilled at it in different ways. So that's one thing you need. Josh Wolfe 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 works. Barry Diller's been very open about the conversations he had with Dara about taking that job and encouraging Dara to take that job.

And I think in there was 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.

That was a good choice, by the way.

Well, there's another thing that Dara was great at, which was 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 was able to slowly, one by one, take care of each of those, which was imperative for the company.

And not easy. I mean, look at the London situation. It was remarkably bad and hard. And he went in and made that better.

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

Yes.

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. Yes. 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— He's usually pretty good.

I know. That was bad.

That was like, "Oh, my God, that's the plot of The Matrix." He talks a lot.

But the problem of AI is worrying people that they can't do their passion. 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?

Well, I think that you bring up a good point. Like, are you looking at it from a bottom-up or a top-down perspective? Either way. And from a top-down perspective, you know, 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. Um, you know, uh, 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, and, and I don't mean to be defeatist by that, but, you know, the country used to be 98 percent agriculturally employed and it's 2 percent now.

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 US 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, understand what it's capable of in your industry and be the—what I said—be the most AI-aware person in your job, 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, 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. 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. The truth of the matter is, you could never learn faster, quicker, more thoroughly than any time in history, than right now. And so if you're constantly learning, honing, you know, if you're figuring out how to get AI to help you be more productive, like, you're going to have 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.' Yeah.

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.

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, uh, 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 purpose for it. We'll be back in a minute.

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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. 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? Right. I really didn't. Someone said, what were they like? I'm like, I have no libertarian light.

It didn't come up.

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. I'd love to know what that means. You're going to obviously try to tackle big policy issues like U.S.-China, the U.S. healthcare system, regulatory capture. Talk a little bit about what that means.

And by the way, 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.

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. Right. The solutions you suggested—overturning Citizens United, mandating transparency, political fundraising, get rid of a revolving door between government and lobbying—are versions of regulation. Talk a little bit about that.

Yeah, and by the way, 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.

So talk about how that's changed your personal political philosophy and what you're trying to do here with these Three Ps.

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 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. 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. 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 financial literacy as a required course in high school. He's got 20 states to put that on the ballot. 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.

What does "three Ps" mean? Purpose, progress, prosperity?

Um, it's something that spoke to me. I—Matt Ridley's book, *The Rational Optimist*, is one of my favorites, where he talks about what's driven prosperity around the globe. And, um, and yeah, just having the biggest impact you can possibly have. Like, and, um, I'm a big fan of this 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. We have that in Austin for the mayor's race. And you end up with a centrist Democrat instead of a far-left Democrat. And it can work on both sides. Because the—more of the citizenry is involved in the actual vote that matters, the last vote, which doesn't happen if you have traditional primaries.

FYI, though, Matt Ridley is a libertarian with a staunch support of Brexit. May not have been right about that, necessarily.

May not. But I love his book, *The Rational Optimist*, covering about, like, a thousand years prior to now.

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 solutions-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. Yeah. 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." "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, trying to insert himself everywhere.

It feels very Putin-esque to me, you know, in terms of what Silicon Valley used to hate. Right? And then the high-skillings, 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.

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 that... 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.

Where does it go next? Because he's inserting himself.

I'm not a fan of backing weapons companies as venture capitalists. Look, I'm out now. No, I get it.

But where does it go? You're a smart guy. Someone asked me this the other day, and I'm like, I don't know how they're going to get themselves back.

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 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. 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, you know?

But what has to happen? Because I've never seen a group of people that have gone from, 'We love you,' you know, the imagery now is very different. Billionaires, 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.

Well, I think a lot of people are worried about that. I mean, even on the famous All-In podcast, I think Friedberg 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. I think Anthropic is going to be enormous. That's my feeling, because I think they're the next version of Silicon Valley.

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.

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 moneymaking, and that's very different. But coming back to regulatory capture, as I mentioned earlier, your solutions like overturning Citizens United and

Well, I think that would be big. I don't know if it's possible, but it would be huge.

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. This is in Maine?

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.

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. And when you do that, you lose innovation there. You lose disruption. You lose all the things we watch happen in Silicon Valley.

Is that the direction tech feels headed in? Because it feels rather oligopolistic.

I think, for that very reason, Anthropic and OpenAI are begging for regulation 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.

So, just a couple more questions. After the Supreme Court struck down Trump's use of the 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 practices, including discrimination against U.S. tech companies—for example, with European regulations on the block, I would assume. You've spoken out against the tariff. So have I. And you, more against tech regulations in general. I would like, if you... What do you make of this approach of, like, punishing the EU for writing regulations that affect America?

By the way, I'm not against uncaptured regulation. There's just not much of it. But on the tariff thing, look, I, you know... And by the way, you've spent way more time in D.C. and I'm just getting started. So I say all this with a lot of humility and naïveté. But the, the abuse of the executive power, which has happened on both sides of the aisle for many, many presidencies now, I think is 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.

Do you think it will be effective, given that unitary executive is one of tech's favorite things, isn't it?

I don't know. I don't know. I don't know. Do you think it'll be effective?

It's been turbocharged with Trump in this case.

Do you think the decision will be effective?

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 run 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 the globe that they will—it would be more easier for them to rationalize agreements with China. That's correct. And 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.

Yeah, I think in everything, including health care, 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 industry. When I last interviewed you, I called you the worrywart of Silicon Valley.

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 mags 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? Or when you talk about these MAG-7 having these caps, I think it's extraordinarily dangerous.

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, you know, philosophers that wrote in the 17- 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—and one of—but one of the checks and balances against it is always, you know, there's a—there's a notion in academia called pure competition, and in pure competition, marginal cost, you know, marginal price eventually reaches marginal cost and there's no excess profit there

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. 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?

And more innovation, presumably.

Yes, possibly more innovation. And that ties into regulatory capture because in some cases that can be what might lock in a monopolist.

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. You know, 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? What would be your three things, very briefly, you would tell them?

One thing I would do is just tell them to take a really deep breath. I don't think that attacking your life with the weight of severe anxiety is going to be very helpful. 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, read more like a textbook, it's not, it's not necessarily believable, right? It's just this bunch of words. And hearing about other people that have started on—the, I believe, and the reason the book's structured that way is I think it can be inspiring.

Like, it can tell you, 'Hey,' and maybe you see something in one of those stories that, that fits you particularly well. Um, and, 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, 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, being pushed towards that is just not inspiring and doesn't give you the sense that you're in control.

And one of the takeaways from the book is—I use a 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?

Yeah, that's absolutely true. You know, it's also—I just recently taught at the 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.

Well, you know, I'm thrilled that you called the book, like, hopeful. Like, 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.

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.

Today's show was produced by Christian Castro-Cid, Michelle Loo, Catherine Milsop, Megan Burney, and Kaitlin Lynch. Nishat Kurwa 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 Vox Media, New York Magazine, the Vox Media Podcast Network, and us. We'll be back on Monday with more. Thanks to Cologuard for their support. We focus a lot on what we put in our bodies, but not nearly as much on what comes out.

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