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

talented people were very generous and untalented people weren't.

Hi everyone from New York Magazine in the vox media podcast network. This is on with Kara Swisher and I'm Kara Swisher. My guest today is Fain Venture Capitalist and author of Running Down a Dream how to thrive in a career you actually love. Bill Gurley. Bill was a top rank 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 known for early stage investing and very tall venture capitalists. Bill was an investor in companies like Grubhub next to our open table, Stitch Fix, Zillow and most not only Uber. After a long 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 going to beef with all the Silicon Valley people but I wasn't because Bill is thoughtful. He's a great

debate or even when you don't agree with him. He's always been a gentleman and he actually

reads it as 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. 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 Costa-Shahi, the CEO of Uber, so stick around. Support for this show comes from Vanta. Vanta uses AI and automation to get you compliant fast, simplify your audit process and unblocked deals so you can prove

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And retail actually builds it. On your company's data in your cloud with enterprise security built in, go to retool.com/vox. We all need to retool how we build software. Build girly. Thanks for coming on on. Thanks for having me on here. 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 renown former VC. I met you when you were investing. I was a stock analyst and then I spent a year and a half at Hummerwind Blad and then I went to

“benchmark. I think it was probably back when I was a stock analyst.”

I met you and Mary Meeker was also a stock analyst and you both became investors. And then I think I ran into again at Hummer and then I think I wrote the story when you went to benchmark and then you invest in eBay. But fans of the show, people who know you actually know you from super pump as the fictionalized version of you play

by Kyler, 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 a end of the bench.

I got a lot of experiences. And became a computer scientist,

“worked at Compact, which you'll remember of most people”

want 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 Quattron. He's the one that took me out to Silicon Valley. Famous banker. Famous banker. Got in a bit of a 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, 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 were 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. They don't leave. It's very much like Congress. They don't 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 take. My”

listenership is broad and quite a bit from tech. And just for people who don't know, you're 68. You're all the benchmark people where I remember sitting across tiny me. They were, I think the new guards, not noticed. No, that is tall. No, but you're all the way, hence the basketball thing. But you're being very

polite about yourself. But Bill was sort of the hot ticket

item of venture capital. 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 text is announced. Yeah, whatever. You're stayed a reason for writing this book is quote to give everyone as much permission as much confidence they need to pursue a career they love.

Talk about why you decided to do this and who or what is something people from pursuing careers they love. So for a better part of two decades, I wrote what was a newsletter. It actually started as a facts and became a blog post called above the crowd of reference to the height. 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 is, you know, some type of digital note taking, you know, whether it's in myself word or now

notion, you know, moved to quit. But I would start ideas. And you probably do this to 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. And they were critical from who were the biographer.

But it's a weird array of people was Bob Dylan, Bobby Knight and Danny Meyer, the New York restaurant tour. Bobby Knight, the college basketball. They all started with intentionality on the very bottom wrong, 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, you know, analyze how an internet marketplace 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, who the author of Atomic Habits, he posted it on his website. So then a few different people kind of poke me and told me, you know, you should go do this. One of those was Tony Fidel, who's become a close personal friend and Tony wrote this book

build. You probably, you're probably. And Tony really

“well. And Tony told me it's the best thing he had ever done.”

And this is the guy that invented the iPod. We're ran engineering the iPhone and launched Nest and you're like 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 investment 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? Right. Yeah. 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

people from pursuing them? Yeah, you asked that early. Let me get to it. There was a Gallup poem 2023 that like 53% of people are disengaged at work. And that's not great. We've all heard about quite 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 they're passionate about

“what they're doing. The second thing that I think is happened”

and 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 about the fact that Johnathan, Hight and Colling of the American Mind, called it the resume arms race. But somewhere

starting around sixth grade and your parent, I think you felt these pressures, right? You start worrying about getting your

child in the college. I never was like that, but go ahead.

Yeah, no, I've just seen you, you're aware that these societal pressures are out there. And so people start, you know, worrying about cello lessons and chest lessons and volunteer work and students today are programmed from a time perspective way more than our generation was growing up. We just weren't scheduled

that often. And what some people believe and I think it's consistent both 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 school. So you've brought that forward like three years. When the main ticker is obviously is you'll 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 I know he said 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. We'll spoil it turning into 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 books divided into profiles and principles. So it's stories.

We're going to get to those in a second.

But almost every single one of these people started on the bottom wrong. My favorite story from that perspective is Jen Ackens, who's probably the most famous hairstyles of all time. But she moved to LA with $200 in her pocket. Like it 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, you know, Scott's not the only one that says that I've heard another receipts say that.

And I think Palmer lucky 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 logists love winning.

Maybe not in Scott's case, but in this receipts case,

and maybe Palmer's case. And if you love winning to death, like then that is your passage. And 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 economics 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 for money. A real passion for it. For economic reasons. Yeah, yeah, yeah, yeah. Right.

So let's dive into the view of the six principles you lay out in the book to achieve a flourishing purposeful 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? 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 thing is just to give yourself permission

You know, Angela Duckworth has, in a graduation speech, said, "Act like a pair of me seem to 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? One of the founders of the acquired podcast had this thing you used called side hustles, where if you 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 Medrona and asked if he could start a podcast. You also have to have a job person that's willing to do that. When I was 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. It's not just finding your fascination, but getting support for that presumably. There's no doubt. And parental supports a really interesting thing.

There's an anecdote I discovered after the book was out where Makana Hay was another austenite here was in 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 Makana Hay says it was the last thing he expected and the best thing he could have said. Right. Because it said not only is it okay, but if you're going to do it,

like I expected to do it really well. And so it was this push with both support for responsibility. And as a parent that I've seen this, like you want to push them towards the safe job with the money. Like it's just an instinct that people--

Well, they often want to do it. I just had a discussion with my oldest son about that. He's like, well, I have to remember.

“I'm like, why don't you figure out what you're going to add?”

And then you will earn money. But speaking of Angela Duckworth, who you mentioned when I interviewed you in 2016, you brought a purple grid. I don't know if you remember that.

This is 10 years ago almost.

First thinking has could have been influential on you.

She comes up a lot in the book. One of her findings is that the Y is usually the overlap part of finding your passion or fascination. In other words, purpose matters. What is your Y?

And how you figured it out? Why that is important? Why the Y is important, I guess. Well, the second principle of my book is titled "Home 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 is 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 sync, 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 we talk about your wife. 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 wife? Why did you decide? So I, when I was an engineer, compact, and I got started on our third project.

It looked like the second. It looked like the first. And I got intellectually bored, especially when I did this exercise. I asked myself, "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 know for me.

You know, for whatever reason. And I'm thankful that I had that kind of ability to think forward like that. Basos 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,

It's kind of similar.

So I was at the Washington Post and I looked around and I said,

"I don't want to be anybody here." Right. Yeah, exactly. Without necessarily judgment on anyone there, it's just not a fit for what you see as something

that gives you energy. Just let me press you. Does that require? And like I finished up this longevity thing and one of the speeches I used was 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," like writing. Yeah. 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 when you're younger? I think it is.

“I mean, I think that's why I mentioned that exercise.”

I think what, and look, young people don't see the end of time. Yeah. I just don't, it's not part of their mental framework. And I don't necessarily think, filling their brain with anxiety is necessarily a positive thing.

You know, actually, death acceptance makes you live longer versus death. Okay. I'll buy that. And I think Jobs was onto something. But I wanted to pivot to one thing on the regret side.

So Daniel Peak 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 caused the most anxiety for people not just Americans, but he studied it in a bunch of different geographies,

is what he caused regrets of an action or boldness for regrets. And so we're relatively good as a species that forgiving ourselves from mistakes. We just don't dwell on them after they're done.

And 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. That we did the things we don't do. So when you left compact,

“what was 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? Well, so I don't know that it was that fine tune 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 compact, I had read one upon Wall Street by Peter Lynch and I had started studying and trading text 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 the sense of compact 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 Biden. What was Arthur? Uh, Info World. Yeah. Yeah.

There were other sorts. But yeah. So I started reading those. And you could see there was more than just what was at compact. 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 compact. My sister was an employee there early. And so I had a cent, you know, door was on the board.

So I had a sense that there was this venture thing. But I didn't really know how to get into it. It's John Jones. Yes. And it was interesting to me.

But I didn't know how to get at it. So. So business school was the way got you to your why. Yeah, but I, but I went through New York first. So I, I noticed the safer.

When I, when I was reading those, man. No, when I was reading those, those periodicals. The dream team at Goldman at the time that covered all the text stocks. They were just mentioned constantly. And I really enjoyed my, 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 Jamie, New York. Right. But it's interesting because to me, whenever I looked at investment banking,

I thought about it.

Or, and it 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's. And it's like, 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 it's, your book is unique is how you empathize.”

They need to find great group of peers. You illustrate that with a program. Jamie Donaldson also known as Mr. Beast. 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 in fighting at these companies. And you see even see it in today in these AI come. 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, 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 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.

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 cause, 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 we're all in athletic departments working out 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. 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 wrong of the latter 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 willing 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. And most industries outside of downhill skiing. There are many, many winners. Lots of successful VCs. There's lots of successful riders.

Lots of successful podcasts. There's 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'm personally, others have said this. But I think I think all of them said it recently. I think ideas are a dime a dozen. Yeah, 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 about the crowd. People like, why is it given away? Because I'm like, he's not giving away. He's thinking it out. I was, I remember having an argument with someone. 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, what's the, I'm, you're not going to hurt me by me telling you my secret, my supposed secret. And then you build trust, and you build better, you better trust in those networks that get more information, sharing the other way.

“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 on with Keraswisher comes from groans. If you're looking for a health goal that you can actually stick to, you might want to check out groans. Groans is simply daily habit that deliver real benefits with minimal effort.

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Visit Stonyfield.com to find Stonyfield organic yogurt near you. Another profile on the book tells the story of a guy named Jay Sweetie quit a job teaching English at Princeton Day School. That's where I went to school, by the way.

But 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 this 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 try.

Like I started podcasting in my 50s, right? Not in young years. By the way, Jay is one of the happiest people on the planet. Yes. Like if you could just spend time with him. So talk about his story.

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, 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 weight 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 Gaffin and Delir and all these people started at a very bottom wrong. You know, in what was the mailroom in Hollywood and all succeeded. And so, 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 a pushback on Scott's thing. Like, you can start on the bottom wrong.

Like, there's no reason you should even have the perception. You should start how you're in the bottom wrong. No, you know, it didn't give me a give 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 were honest with it. That's true. It was such from that little perspective of delivering mail. It was really, like, it was an eye-opener. Well, that fits nicely with my sixth principle.

So I would like to add that information. It always gives back. Like starting from the very, 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.

Yours comes from Darra Costa, Shahi, the CEO of Hoover. Someone you helped get his job, your instrumental in getting his job. I think 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 what 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 Darra from the CEO of Hoover to ask the 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 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 and a small pond is a win.

Or they're worried about over competition.

But the thing is, many of the principles that I have in the book from constant learning to peers and mentors are just ten to a hundred 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.

And there's just that much. What is that changing? Not technically necessarily. But are there epicenters anymore? I think they're all I think.

Yeah, I think they're, I mean, you know, 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. You know, 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.

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 high. 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 positions. It's an important skill for VCs.

It's probably your only most important skills.

And it's hard. I think what people would say CIO higher is 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, there's a big difference between a founder maybe in a CIO higher.

So I would, most of the time by the time you get to a CIO higher, you need someone who's capable of leadership. Because you usually, by that time, have a thousand employees or more. And leadership is an 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 Miller's been very open about the conversations he had with Dar about taking that job and encouraging Dar to take that job.

And I think in there was a sense that she felt Dar 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. That was a good choice, by the way.

Well, there's another thing that Dar was, was great at, which was, 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 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 and hard. And he went in and made that better.

Right. Well, he made his greatest qualification as he wasn't an asshole. But the threat of AI driven in job losses. Yeah.

“You said the best way to avoid losing your job is to become the most”

and enable the version of yourself. That works on an individual level.

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... He's really pretty good.

I mean, that was bad. That was like, oh my God, that's the nature. That's the nature. That's a lot. You can't talk too much.

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

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, dear, you look 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. 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't control. I don't know that there's anything we can do.

And I don't mean to be defeatists by that. But, you know, the country used to be 98% agriculturally employed and it's 2% 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 as 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 our the US government having a wildly successful retraining program over the next five years.

I know imagine that. And so, if you're doubting 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. 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 along the way, you know, a modern farmer has tractors and is using drones now and all kind of stuff. And they didn't in the past. 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 that may not love. I think they are right 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 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 in some people view it as, oh my god, I'm dead. Well, one of the things, the safest jobs are the ones that read like lawyers.

Software engineers, right? Those were always considered the safer choice that's right. Which is interesting. 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 idily in the job and don't really have a wire or purpose for it.

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Let's talk a little bit about Silicon Valley and what's happening right now. Because you've left as a big leader there. But politics is now sort of enter the picture, 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? I really didn't. Someone said, "What were they like?" I have no libertarian life. They didn't come up. They didn't come up and they in fact disdained it. And the first time I had Bill Gates to wash impodesies.

I don't have lobbyists. I never come here.

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. I'd love to know what that means.

You're going to obviously try to tackle big policy issues. Like US China, US healthcare system, regulatory capture, talk a little bit about what that means. Yeah. And by the way, you know, I gave this talk that I was originally going to give it your conference. I gave it a year later at all and because I'm fortunate 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.

The solutions you suggested was over turning citizens united, mandating transparency, political fund writing get rid of a revolving door between government and lobbying. Our versions of regulation talk a little bit about that. Yeah. And by the way, but I was going to just say that the punch line of that talk it was called 2851 miles. That was the distance to the program. Yep, I remember.

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. Right, right. And they're so close. So talk about how that's changed.

“Are your personal political philosophy and what you're trying to do here with these three pays?”

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. And there were people like Steve Pinker, the callous and brothers, Josh Wolf and Elon that we're saying that had to 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. Like I think that's good. Like these credit card companies chew these kids up and they have no awareness of this type of stuff coming at him.

“So what is what is three piece meat purpose progress prosperity?”

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 prosperity around the globe.

And 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 and gives.”

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 the more of the citizen tree is involved in the actual vote that matters the last vote, which doesn't happen if you have traditional primaries. FYI, Matt Ridley is a libertarian with a staunch support of Brexit. May not have been right about that necessarily.

May may may may not. But I thought his book that the rational optimist covered about like a thousand years prior to that. But one of the things that is happening is, you're trying to be a solution-based person.

Presumably, you've always been that way.

But Resident 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 line, kind of liberal tolerant on the social issues, everything else. They tried to stay out of politics as we was always lying experience. They have now publicly embraced Trump in ways that are so awkward. As some of them, I would put them in a 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, sheer holder value. You know, he's trying to insert himself in the Netflix series, trying to insert himself everywhere.

“It feels very poot-nasked to me, you know, in terms of what Silicon Valley used to hate, right?”

And then the ice killings, I think, 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 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 as part of the requirement of being successful, it's not the type of place where, you know, two young people on 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 is very idyllic notions and thought of it as this kind of corporate version of American ice. Like, I don't like that element of it.

We're just gonna go next because he's so upset. And I don't, I'm not a fan of backing weapons companies as venture capitalists. And I look, I'm out now. So like, I'm not. I get it.

But where does it go? Your smart guy? Where is it? Because I just, as someone asked me to see 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, you know, several people have decided to get really big. Whether it's entry, center, thrive, or secure, 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, 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 billionaires, Gary billionaire, evil billionaires, 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 free bird is concerned about this writ large that it encourages behavior that could become anti-capitalist and therefore it's very dangerous. And, and I think you got to be careful what you say. I do think anthropic, particularly, but even open AI are begging for regulation.

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. They've been spending money, you know, not just in a national level, but in 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 mean.

I mean, you couldn't say all the good things about Elon before, but Elon now is not good for tech.

But coming back to regulatory capital, 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. Actually, just didn't really interesting interview with Larry Lessick, and there's a case that will basically kneecaps citizens united. And that's good enough.

I'll familiar with this, this is in Maine. Yeah, exactly. But, 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 US where there's heavy regulation, you've ended up with less diversity, fewer companies, more of a oligopoly.

I mean, look, look, it's looking at playing building, we're down to just like one company basically. And, and when you do that, you lose innovation, you lose disruption, you lose all the things we watch happen at Silicon Valley. And so, I'm-- Is that the direction tech feels headed in? Because it feels rather-- It might be--

Well, thank you so much.

“I mean, I think for certain the reason and anthropic and open AI 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. So, just a couple more questions.

That's in the Supreme Court.

Struct round, Trump's use of international emergency economic powers act to enact tariffs. The administration now is 15% tariffs across board. Also, it would begin official inquiries into unfair trade priorities, including discrimination against US tech companies, for example, with European regulations on the block I have assumed. I'm used to poking out against the tariff, so if I, and you more against tech relations in general, I would like a few. Would you make a this approach of this punishing EU for writing regulations that affect Americans?

But I'm not against uncaptured regulation. There's just not much of it. But on the tariff, and 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 naivety, but 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. Do you think it will be effective? Given the unitary executive is one of tech's favorite things, isn't it? I don't know. I don't know. Do you think it will be effective?

Yeah, it's been turbocharged with Trump in this case. Do you think the decision will be effective? I don't know, because a lot of people-- I don't 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.

So we always had agreements that weren't necessarily-- you know, it's happened before in our history.

But no one 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 un diplomatic with our partners around the globe, that they will-- it'll be more easier for them to rationalize agreements with China. 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 their 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 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, obviously cars and everything else." So it's-- you're absolutely right.

So let's-- let's finish up your known for being a voice of warning and industry. When I last interviewed you, I called you the Worry Ward of Silicon Valley. That's for you. Let me read two quotes of your recent interviews gave. They highlight your reflective nature, and one is capitalism and democracy corrupt each other over time.

And the other question you asked is America really benefit by the fact that the mag seven have three trillion dollar market caps. You asked it earnestly, your answer is essentially maybe it doesn't. I know use was not surprising to me, but it's probably surprising to hear a different voice from Silicon Valley

When you talk about these Worry Ward things, do we need more democracy or more capitalism? Or when you talk about these mag seven 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, you know, 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 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 the checks and balances against it is always, you know, there's a notion in academics called pure competition.

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, because competition is little bit 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, 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 with those numbers, be lower, would prices be lower, would you have more companies with more employment necessarily? And more innovation, for example. Yes, yes, possibly more innovation.

And it ties into regulatory taxes, because in some cases, that can be what might lock in a monopolist. Right. So, you know, a lot of young people that 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. If you, what would you say, a young person comes to you and says, I just this work.

Fug a moral, it looks like the billionaires are running everything. AI's 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 you be or three things very briefly 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.

“Even if you want to change the world, I don't know that it's going to be helpful if you're paralyzed.”

The second thing I would say is that 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 better books in the career space are read more like a textbook, it's not just fairly believable, right? It's just a bunch of words. And hearing about other people that have started on the bottom wrong and made it can be, I believe in the bookstructure that ways I think it can be inspiring, 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, like, it's fun to talk to them about what it may be.

And I think they've been told by so many well intention, 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, it's just not inspiring and not then 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?

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.”

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, and I'm thrilled that you called the book like 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.

So now you're not the worry work, but that's because they're all right. So badly. Anyway, build. Thank you so much. It's great to talk to you.

Appreciate it.

“Today's show was produced by Christian Castro Sal, Michelle Loi, Catherine Millsop, Megan Bernie, and Kaylin Lynch.”

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