Bill Gurley: How The A.I. Boom Shapes The Future Of Work

Everywhere you turned in 2025, it was the same headline: "AI will replace 50% of jobs, 70% of jobs. White-collar work won't survive the decade." If not now, then soon. You were told your industry might disappear, your skillset might expire, your role might be automated. And even if you tried to brush it off, it still created fear. Is my job safe? Is this overblown? Am I about to become irrelevant? You sit here now, not necessarily panicking, but waiting and watching, trying to figure out what's real and what's hype. And you're not alone. Everyone feels like they're in a holding pattern. Is this the greatest technological shift of our lifetime or the most sophisticated product marketing campaign ever executed?

Are the tech founders forecasting the future, or are they selling it? Because the louder the noise gets, the harder it becomes to separate signal from speculation. And when your livelihood is on the line, speculation isn't good enough. If there's anyone who can help us make sense of this moment, it's Bill Gurley. For decades, he's been at the center of the biggest shifts in Silicon Valley, not watching them from the outside, but inside the rooms where they were unfolding. He was an early investor in Uber, not because it was trendy, but because he can spot technological disruption from a mile away. He's built a reputation not for hype, but for seeing how new technologies reshape labor, incentives, and entire markets.

And right now, the question isn't whether AI is impressive. It's whether it will fundamentally change how we work. And if anyone can separate fear from reality, it's him. And that matters because modern life has changed in ways that make living well harder than it should be. And the coming wave of AI threatens to accelerate that instability. Most of us are already operating in survival mode—reactive, guarded, just trying to keep up, feeling behind before we even made a choice. And that's why Mighty Pursuit exists, to give you a North Star, integrating mind, body, and spirit into one clear roadmap for living well. The podcast is where we slow down and examine one part of that roadmap at a time.

And today, we zoom in on purpose: how AI may reshape our work, our careers, and whether we'll still be able to spend our days doing something we actually care about. Think about this episode as a survival guide for the coming age. It's practical, it's clear, and it's actionable. So let's get into it. So, I want you to picture a 26-year-old named Maya. So, she went to a decent school, earned good grades, landed a role in a safe field. However, she spent all of 2025 hearing that job loss is going to be catastrophic due to AI. Now she's kind of afraid not only that her livelihood is going to go out the door, but her entire sense of meaning is going to be erased by a machine that could kind of do her work in six seconds.

I think it's an interesting premise because, as an investor, you know, you've built a 30-year career making bets on technology that's going to change the future. And you've been right many times. And so, when you look at Maya and the people that represent her, do you feel like her fears about the coming age are irrational?

I don't think they're irrational at all. Any technology wave is likely to have an impact on society and an impact on certain industries. People have no reason to have knowledge of this, but the US used to be 98% agricultural. That was the only career that existed. And it's less than 2% today. And if you remember all the Farm Aid concerts and all that, that was a slow reaction to that. And the notion of a Luddite goes back to mid-century Europe when the loom first was created. And people pushed back against that as well. I think that the reality is there's this chapter in – Stephen Covey's The Seven Habits of Highly Effective People, where he says, know what's inside of your control and outside of your control and focus on what you can control.

I don't think that there's a reasonable reality where technology is kind of put in a box or turned off or stopped. I don't think that's going to happen. If you recognize that it's outside your circle of influence, then the question becomes, how do you think about this and how do you respond to it? How do you most effectively surf this wave that's happening, if you will, even if it may represent a threat? I think it's a threat you can't stop from happening. And putting it in that pragmatic mindset takes a lot of, a lot of the arguments off the table. 'Cause there's no, there's no, like, you could vilify it, but there's no point in that. Like, or it's not a helpful exercise to help her get to where she needs to be.

Yeah. Yeah. It's just, it's been so dominant in the news headlines over the past year of a lot of big people behind the technologies, Elon Musk and Sam Altman and, you know, Dario Amodei, all making these public statements about, like,

Huge job loss. Um, can I, can I also though frame that, like, like they're also raising billions and billions of dollars for the company? They're leading the biggest secondary transactions for their employees in the history of, of venture capital, the history of the world, and so people are putting billions of dollars in their pocket. And so there's also a huge incentive from the two leading model providers to seek regulatory protection, which most people wouldn't think regulation is, but they've been begging for regulation since they started, from three years ago. And the reason I think they want it is the biggest threat to their businesses, where they're cashing in billions of dollars, is the open source movement.

And so I don't know that I buy all of it. I think some of it's theater. There have been polls. This is super interesting. There probably weren't where you thought this was going, but there have been polls about this AI anxiety in China that are a fraction of the anxiety levels that they have here in the U.S. Why? I think it's because the leaders over there that are working on these products aren't doing the doomsday stuff that Dario is doing. It's just bizarre. The people leading the effort at the top companies here in the U.S. are the biggest doomsayers. It's… radical but i i would also say we have been prone to overstating these risks in the past there's still people working in banks today despite the fact that the atm there have been studies that say there's more bank tellers today than there were like 40 years ago yeah um and that doesn't mean that some didn't lose their job we're prone to getting over excited about these things as humans yeah

Yeah, I think that that's a really interesting observation. And I think people would be curious because as an investor, right, you have been in these rooms for 30 years. And so one of the theories that has emerged over the past few months or even six months is that the hype around these technologies—and while the disruption might be real, the hype around them is being driven by people trying to sell their own products, which will allow them to raise more eventual capital. Is that actually happening? Yes, I think that's actually happening.

Now, look, I don't want to suggest it. I want to be very clear. I'm not making the argument that this won't disrupt certain jobs. I think the paralegal space is already happening.

I think the number one way to protect yourself against dislocation from AI...

...is to be the person in your field or your company that understands what AI is capable of the most. And there are anthropologists who have talked about the fact that we evolve with our tools. A farmer with a modern-day set of tractors and drones, even, like, have worked their way into agriculture, would crush somebody trying to use a hoe and a horse and a plow. Like, they would just crush them. And that farmer's evolutionary fitness is... commingled with his tools that he has. And this is a new tool. No one that works as a paralegal or a computer scientist would think about trying to do what they do without a computer. That's a tool that evolved to be a part of the work environment if someone were in a role like that.

And this is a new tool. It's a pretty powerful tool. If you've played around with it, you have... the intelligence, the broad intelligence of the world, you know, a prompt away. Like, like Wikipedia was pretty cool, but this is—this is even that, yeah, on steroids. And I would argue that if you're a high-agency individual who has determinism about where they're going and views their career and what they do in an artisan kind of, craft kind of way, those people think about AI as this massive jetpack that helps them be a better version of themselves. And I know these people. Even, even local, I've met a lot of local entrepreneurs that, like, um, run, whether it's restaurants or storage facilities or laundromats, and...

These are pretty entrepreneurial people, mind you, but they're like, "Holy crap, I asked it to find a third location for a laundromat in town based on the demographics of where this is working, and it gave them five addresses and then looked at what buildings were." They're just, like, blown—they're giddy. They're like happy-giddy about this. And if you—one of the tenets that I attach to highly successful people is continuous learning. And learning from not just up and through college, but every day. And once again, you have to have this mindset of high-agency and developing a craft. But if you want to learn, if you just want to proactively learn, there's never been a better time in the history of the world.

It is so amazing how much you can learn at any point that you want on any topic that you want. And by the way, it doesn't just include AI. Podcasts, YouTube videos—like, the amount of knowledge that's right there in front of you, one click away, is almost staggering. Like, it's unbelievable.

I mean, I totally agree with you. I think I had a moment last year where I was like, "Wow, like, this deep trove of information, like, I would have had to pay someone, like..."

$10,000 an hour.

Certain things. That doesn't mean that there's not value in sitting with people and learning things, but the amount of wealth of information that can be accessed at this point in time is staggering. Like, literally impossible before. Like, you couldn't do it at this level before, you know?

Yeah, and look, going back to the story that you started with, I mean, I think a big question for her is, is this something you truly love or is this something you fell into, you know, by following a normal college career path and just, you know, got a job? And because the reason I bring that up, well, first of all, I think that our society, you know, has evolved to a place where we have a lot of structural systems that push people towards safe jobs. Both the way the college process has evolved, which we could get into, which I think is highly stressful and not ideal, and parents who I think are remarkably well-intentioned. There's an instinct. I have three children. There's an instinct to worry about them, especially from a financial, economic stability standpoint.

But, um, if someone ends up—and there's some data from a 2023 Gallup poll that suggested over 50 percent of people are quiet quitting. They're in jobs they're not highly engaged at work. And if you're not highly engaged at work, that means you're doing no continuous learning. You're not trying to—I think another Covey principle was "sharpen the saw"—like, you're not doing that, you know, you're just sitting there. And if you're just sitting there and you're kind of meh about your job anyway, and you're not playing around with what AI can do in your field, you might get run over. Like, you really might get run over. And so, I would—might—I would want to spend time with her to understand, like, is this your calling? And if it's not, maybe this is a great time to re-channel the anxiety you have about what the—this current job you don't love...

now, having risk to explore what, what's possible and go into a field where you have the right kind of passion, where I think you can outrun, um, things like this.

You spoke about there was a time when your profession was inherited, right? So, you know, you go back to the early 20th century and then before that, right? So, it's, like, usually by your bloodline. And then 20th century gave rise to, I guess, what you could call knowledge work today. And so, the knowledge class is barely 70 years old. So, there have been a series of evolutions. It feels like, in some ways, the technological evolution over the past 30 years have been—I mean, you have the internet, which pops out in the '90s, and then social media, and then all the smartphones, and then all the apps that are put on smartphones. Now you have AI, which is, like, it's condensed three-year period. And so, how do you see this moment versus previous moments?

Do you see this just a next chapter in the story, or do you think that this technology is different than the other technologies that exist?

It's certainly different. So, the venture capital community, which was my dream job and where I spent a quarter-century working, always gets very excited about new technology waves because they allow for disruption and allow for new winners. Since I was operating as an investor, we had a PC wave, then a client-server wave, and then the internet popped up, and then we had a SaaS wave, and then a mobile wave. I don't recall any of those having... There were periods where... When Facebook went public, it fell from 42 to 18 because the world was afraid they didn't understand the mobile wave. And then Zuck got his crap together. And so, that's a threat. But I don't remember any of those previous waves feeling like they threatened so broadly.

And the past week in the financial markets, like, a whole bunch of companies traded down because of fear that this would—would disrupt them. And the other thing is, I think technology in the previous waves threatened mostly blue-collar jobs, and this—this is clearly, with paralegals and computer scientists at the forefront, this is the first time, I think, um, white-collar jobs have been threatened, which, I guess, for the intellectuals, that's a new reality, you know? So, it's—I—the—the investment community, and they're always prone to hyperbole, so you have to—you have to tone it down a bit, but certainly believes this is the biggest one they've seen. If you think about—so, estimates suggest there's over 100 million knowledge workers in the—in the US alone, 1 billion globally.

So, that means approximately, yeah, probably upwards of 60% of the US workforce are considered knowledge workers. So, people who think for a living, like analysts, engineers, marketers. So, if there's changes there, the cognitive labor shifts dramatically, what do you—I mean, there's been much that's been made about, like, megatrends. What are you anticipating, like, the fields will morph into, or changes, or things like that?

I think you got to segment the word "knowledge" into a couple of different buckets. One, if you're merely answering the phone and reading a script that the computer is telling you to read, I think that qualifies broadly as a knowledge worker in your accounting, your 100 million. But you're not using that much of your brain to execute that. You're typing. You know what I'm saying? You're doing rote skills with technology. Um, another, the paralegal one: you're doing searches, you're summarizing, anything with language, quite frankly. And I would say customer service and, and paralegals, um, LLMs are really good at language and sorting and synthesizing and, and, and identifying like search-type query things, and those are threatened, you know? But I would argue...

I guess it's a subtle use of the word "knowledge." I would argue there's not much knowledge that was going into that actual work product. The coding thing's another one. I mean, I think if you talk to people that work in computer science—and I did many years ago—the best computer scientist, it was always about understanding the potential, coming up with the proper algorithm structure. It was never about the rote work. Yeah. But the rote work is the thing that's most in danger. If you are hyper-intellectually curious in your field, one, I think you're going to be at this higher level, or you're trying to get to that higher level anyway, where you're trying to understand the problem that's being solved, and how it's actually solved is not something you're probably overly concerned about.

And then the second thing I would say is if you truly are focused on being the best that you can possibly be in that role, AI has been out for a couple of years now. You've already played with it. You already know what it's capable of. If you're the person who has the most knowledge about AI in your company, in your role in your company, they're not firing you. You're not going anywhere. They're going to be asking you questions all day long. You're going to rise to the top. And so part of this goes back to, are you sitting back on your heels with a lot of anxiety? And if so, you're making it worse for yourself. And it's hard to get out of that mindset, I'm sure. But once again, going back to your example, I would use it as an opportunity to really test, do I really love what I'm doing here?

I mean, you did these large studies.

Yeah. And then that kind of mirrored some of the other data that was already coming out about this. But can you share about that, the idea that most people are currently—

not infatuated with what they're doing. So this Gallup poll, which anyone could go find from 2023, like 23% of people considered themselves highly engaged or passionate about what they do. Some number north of 50% were kind of meh, and then there were like 18%—they were actively like angry and like messing up their work environment. Um, but none of that sounds great, right? Like, you'd like those numbers to be better. Um, and the question is, how do you end up in that place and why? And, and somewhere along the way, while we were studying the, the latest academic work, we, on a whim—we, as my co-writer and I, were doing a ton of reading together and researching—we launched a SurveyMonkey study, and it just said, and it was for people that had gone to college, and it said, "If you could go back and start over, would you do it differently?"

And seven out of ten said yes. Wow. And we redid this study with Wharton to make sure we had done it scientifically as opposed to just launching something on SurveyMonkey. And it was six out of ten. And, you know, there's this great book by Daniel Pink called The Power of Regret. And he makes a point in the book that the biggest – the regret that weighs most on people's mind and gets worse as they get older are regrets of inaction. He calls them boldness regrets. And he separates – regrets of action are I did something, it didn't work, or I made a mistake, and how much do I worry about that? And he argues humans are really good at kind of giving themselves, you know, 'That's all right, you learned, you know, move on.'

Like they don't sit there and ruminate for the next 30 years about this mistake they made. But the thing they never tried, it was that itch that was in the back of their mind that they, 'Oh, I always wanted to do that.' That lives with them all the way to the end. And there's a couple of exercises, one I did and one that Bezos is famous for that I think are a great way for someone that's in this situation to really test how much they love it. And one thing that I did twice in my career was ask myself, 'Do I see myself doing this 30 years from now?' and pushing myself forward in time. One way you can do that, there are people in most organizations that have been around a while and maybe have served a lifetime in that career.

And you can meet them. You can talk to them. You can ask them what their day is like. You can ask them if that was a good decision for them and give yourself a little perspective on whether you want to really be doing that and making yourself think about that. Thinking across time that way, I think, is super helpful. Bezos did it a different way when he was thinking about leaving D. E. Shaw to go start Amazon, which would seem like a really risky move. He was here in New York. David Shaw was like one of the top hedge fund guys in the world. David loved him. I'm sure he was making incredible money, and, um, he went for a walk in Central Park and asked himself, 'What advice would my 80-year-old self give me in this situation?' And he said the minute he framed it that way, he had to go. Like, the 80-year-old self said, 'Life is short. Like, take the chance. You can always go back. Like, what, David Shaw's gonna have him back, right? Like, it's kind of a one-time shot, and...'

He calls that his regret minimization framework, which is a little nerdy. You can go watch that on YouTube. But both those things, I think, are congruent with the Stephen Covey habit, 'Begin with the end in mind.' But just when you're young, life seems like it's forever. But by the time you get to about 40, it starts to really look short. And the more, I think, a young person can try and think a little bit more about how, how short time is by using one of these exercises, they might have a better perspective about whether they want to take the risk to, to try something else, you know? Yeah, I think that that is, uh, yeah, it's so, it's so relevant, the fact that people are, are in these jobs that they...

...not happy with, because that's another way of, of looking at the moment that we're living in, um, and this coming AI boom, and the AI boom that's here, is going to force a reckoning in some ways with people that were already in things that they didn't love doing. And so if you hate what you're doing for so many hours a week, then this becomes like a pathway. I think what, I think the thing that people wrestle with, and I've wrestled with in the past, is, is doing something that you love almost, like there's two things that are at play. There's a survival aspect of, 'This job is giving me income, right? It's paying the bills or whatever.' And then there's this other thing of like, that's higher than that, of like, 'Oh, I would love to do something that...

...I'm really fascinated by.

It gives you fulfillment.

And gives me fulfillment.

Yes.

But people feeling like it's almost like a luxury to bypass the survival thing to get to that moment. What do you think of that mindset? Do you think it's valid?

One potential irony that may exist in this modern time is we may have pushed people towards safe jobs that aren't safe. And so the premise was for economic certainty, which may not be there. So if you're blowing that up, maybe you're blowing up the whole notion that that's something you should do. But I personally – look, I personally believe that life is very short. I believe that you – I think there are way more career opportunities out there than people are willing to admit, like sports or music or movies. And they think they can't go do them because they're not the talent. But the truth of the matter is there's 100 jobs for every one talented person in these support roles in those industries.

And we have a lot of stories of people that rose up in those ways. So even things that seem hobbyish, you know, can be careers if you're willing to tilt against them. There's a gentleman that fell in love with the Grand Canyon, just loved it and, you know, developed a newsletter and a podcast and wrote books. And like he's very successful and insanely fulfilled. He is considered like the top voice on the Grand Canyon.

I think it's funny because I think I saw maybe it was a couple months ago, but an interview that Elon Musk did with Joe Rogan. He was talking about this whole thing of working can become optional or will become optional and any product or service that you want, you can have. These futuristic scenarios that were painted. But when you actually break down how many different fields that there are, it's so enormous. I was just thinking about my building, like an apartment building, right? What it takes to actually build that building. And so the idea that intelligence on its own, artificial intelligence, would replace all of these fields and the fields in the physical world too, like all the fields that you're referencing, like hospitality and stuff.

It would require so much advancement.

I don't believe it, quite frankly. I think a lot of that rhetoric comes from some of these Silicon Valley nerds that have read too many sci-fi books. It's not realistic or pragmatic when you think about it in the way that you did. That's my own personal. I also, and this gets super philosophical, but I don't believe in the notion of UBI or anything like that. I think humans need to feel important and need to feel fulfilled. And I think there's studies that show someone that is taking an income from the government and not doing anything, that that won't be a great life and they're likely to become disruptive.

Yeah. I mean, that's the other piece to it, right? It's like these ideas of universal basic income. It's like the meaning piece, which is really the essence of what you were getting at is the purpose and fulfillment that we get from doing a job or fulfilling a role or working towards a goal. Like these ideas of universal basic income, it just completely strips that away from someone's existence. I know. I don't think it'll work. Even if they were getting it, it's just like they're just sitting around all day like,

No, I don't think it works for a variety of reasons. But I agree with your premise that if you really think about it, it can't do all these things all at once. It just can't. But I think there's an overstatement of it broadly. These people have been... taking down many of the SaaS company stocks. There's no reason, even if you could tell your AI, "Build me a financial ledger that I would use instead of SAP," that's not realistic, because the auditors need to come in and use this thing also to make sure they can audit your books. There needs to be confidence that it's a—a system of record that can't be errors, and there's no reason you would do... And someone highlighted Anthropic is a customer of Salesforce and Workday, and like, they're paying for... So, it's some... There's, there's, there's a ton of rhetoric out there today, a ton of rhetoric. And it's... I'm a believer. Like, I think you can tell from our discussion already, I'm a believer that this is cool and interesting and, wow, yeah. But, but people are taking it too far.

Yeah, I think people just like hear these statements, but then the kind of logical thinking part of their brain of like teasing out these scenarios and then like replicating every human task that like possibly exists across every single field, how it just feels like so unlikely that that would happen. I guess the counterargument to people who are proposing these scenarios is that this technology is going to reach a certain point where it gets to be so smart and it's a superintelligence. You don't believe that either.

No, no. And there are plenty of AI researchers who don't believe it. Like, I'm not like, you know, there are people that study it that don't believe it.

So if someone were to move forward, and whether they lose their job or they kind of on their own accord decide to shift into another career or another path, what's the best long-term—if you have practical doubt, what's the best long-term investment that someone can make in themselves?

I mean, I think the best thing they can do is try and find—try and find this thing that they're so obsessed with that this continuous learning, it comes free. One thing I would tell very young people is don't freak out if you don't know the answer. There's an idea that came from one of the founders of the Acquired podcast where he always had a side hustle in his job. So he would go to his employer and say, "If I work extra hard at nights on the weekends, will you let me do this other thing?" And what's really cool about that: one, that makes you look pretty interesting to the employer, like that you're that proactive, but then you get another rep to see if that's something you might love more.

And he started Microsoft Garage inside of Microsoft while I was there, which is how they stay in touch with entrepreneurs, which I think the company looked on very positively. And he was working at a venture capitalist, Madrona in Seattle, and asked, "Can we start a podcast?" And they said yes. And he started a podcast inside of Madrona and found that that was his life's calling. He's one of the most fulfilled, happiest people I've ever met doing what they're doing. Jerry Seinfeld was in New York, thought he might want to be a comedian, but didn't have the confidence that that was something legitimate for you to go do. And he found this book called The Last Laugh, where someone had profiled 14 comedians and their career arc.

And just reading that was disinhibiting for him. It told him, "Oh, you can go do this." So if you're thinking about a field, and maybe even in that battle card scenario, also go study five to ten people that have made a success in a career like that. Yeah, they're—they do podcasts, they do interviews on YouTube. Go listen to them. By the way, if any of that feels studious, cross that card off. Like, like you should want to go do this. You understand what I'm saying? But, but just listening to people that have done it and been successful can be disinhibiting and give you the permission you need to go do it. Because before you did that, you just didn't know it was real or didn't know how you'd go about it, and just hearing them talk, it will be comforting and give you confidence to jump at it. And it's all out there. This—I keep going back—if you're high agency,

man, this stuff, it's available. It's right there for you to go take advantage of. I love some of the exercises that you're talking about with the AI as well. I mean, you can do so much like modeling, too, of, "Give me,"

Not only with your current career path, but like things that you want, like medium-case, worst-case scenarios, high-case, and sort of these predictive models, and then exploring interests at the same time.

So Danny Meyer was a wildly successful salesperson, did very well as a salesperson for this technology that pins on clothes so you can't steal it out of the store. But he made this decision because his uncle gave him the confidence to do it, to go be a restaurateur. The next day, he enrolled in a class that cost $200 that he found in a magazine on the corner of the streets of New York. Jen Atkin enrolled in a free cosmetology class in L.A. offered by the city and became the top hairstylist of all time. And so people say, "Oh, I don't have the money," or whatever. But I don't think it was the cost of either of those programs that were an issue for those people. One of them was free. One of them was only $200.

But a willingness to say, "Oh, I need to learn about this thing," and to step onto that first rung and get started. And I love both of those stories just because there was this intent: "Oh, okay, I'm going to go do this." And then the resources: "I'm going to take advantage of what's out there for me." And then we—we've taught our children so much, "You got to get into Harvard and Yale." No one would say, "Go take the $200 occupational course, you know, offered at the community college." No one says that. You know, it's not pushed as a way to get to the top. I think, I think, I think that piece, though, is one of the things I feel uncertain about the most because

Throughout history, really, the entry-level jobs and starting at the bottom of a ladder and then climbing that was something that was assumed, at least for the past 50 years. But I think there's a lot of uncertainty that people feel about if those entry-level jobs or the things at the bottom of a ladder are going to exist and if those opportunities are going to shift or go away. So what, what are your thoughts about that?

I think that anxiety is mostly in these safe jobs. Like, like where we cram, like—the college process has gotten, I think, more intense and more structured than it's ever been before. They used to tell you you couldn't declare a major until the end of your sophomore year of college. And there was this philosophy that you should take a variety of core classes so that you can experiment and see what you love before you declare and specialize. Today, at many colleges, you have to apply to the major as a junior in high school. And so that mindset has been lost. And in addition to that, from sixth grade to 12th grade, your parents are remarkably afraid that you can't get into the right school.

Getting into school, every school has gotten harder—every single one—because we've increased the number of people that want to go to college, but they haven't increased enrollment. And so Jonathan Haidt calls it the resume arms race. We start scheduling kids with chess lessons and lacrosse lessons and volunteering at the SPCA. And their schedule looks like a worker—like a white-collar worker, like their daily schedule. And kids weren't like that 30 years ago. They'd roam around and play. Haidt has a chapter in *Coddling of the American Mind* titled "The Decline of Play," where he raises the question, is this the right thing for us to be doing? But it's what we do. And so by the time this high-stress kid reaches college and then gets to the end of it, they're burnt out.

They're burnt out before they start their job because they've been running and grinding so hard. And I also think they feel a massive amount of sunk cost, which—'Oh, I've invested all of this, I now have to go do this.' And I worry that that makes them have blinders relative to exploration even once they get out. And so one thing I love to communicate to young people is, you know, your first job doesn't have to be the career you're in forever. There's plenty of—there's, in Dave Evans' book, he says after 10 years, less than 50% of people are still in the career that they—where they got their major. And just knowing that, I think, might help people relax a little bit and think more about what's possible.

I just feel we've put them through this conveyor belt and there's—there, they feel stuck on it. Yeah, if you know what I mean.

Yeah, I mean, limited in terms of exploration. As somebody would go through the exploration process, are there things that you foresee that would simply be dead ends? So even if you became fascinated by something, are there certain paths or careers or trends that you see probably shouldn't—

Well, apparently, like if you're getting in—here's a really interesting thing I thought of the other day, you know, that's kind of an interesting test. Do you think of it as a craft? Like, do you think—cause I—there's a, there's a, um, lawyer that I've gotten to know, Neal Katyal. I guarantee you he thinks about being a lawyer as a craft. Like, I—I'm certain of it. But if you ask the average human, you know, 'Is being a lawyer a craft?' they'd probably giggle or laugh or say no. And so, if—I think in almost any field, you can think about it. I think you can find computer scientists that are truly enamored with computer science and view the best people in that field as craftsmen. Product people like Tony Fadell, who's a friend of mine who helped build the iPhone.

I know he thinks about what he does. You know, he learned from Jobs. Jobs thinks about what he does as a craft. And I'm sure the guy that did the Grand Canyon work, he thinks about his job that way. And if you get into that mindset, I just don't think you view AI as this thing that's coming after me. You view it as, 'Well, how can I use this to get better at what I do and explore what's possible?' It's just a different frame of mind. And if you're in a career where you don't feel like it's a craft, then I think you are at risk. You're at risk. You're at risk from two things. You're at risk from AI, but you're also at risk if the person sitting next to you does think that way.

Obviously, you had a lot of involvement in Uber. So someone like a Travis Kalanick or an entrepreneur like that, what do you feel like the driving force is? Because a lot of the media depictions that we've seen—like, is that fascination that's driving a person like that when they're, like, a founder, entrepreneur in a company, that they're just pouring into this thing and obsessing?

Well, two things on that front. One, I once asked Jeff Bezos how he was able to be such a good angel investor while he runs the largest company in the world. And he said, 'I only look for one thing: just the determinism of the founder. Like, how... convinced they are they're going to go do this come hell or high water.' So I do think that element's a part of what makes them successful because they become dogged. But most of the founders I meet are fascinated with technology and disruption. That's the thing that they study. And when something like AI comes along, you know, I said, 'Do you spend the time at night learning about this thing instead of watching Netflix?' Most of the founders that are, like, really great, when AI popped up, they did that.

Like, one of the reasons that I know I made the right decision finally deciding to retire, I didn't launch a Claude bot in the past, you know, three weeks. But I bet you most, the top 40% of founders in the world launched a Claude bot in the past three weeks. They couldn't not do it. You know what I'm saying? Like, they just couldn't, like, they couldn't not know why this thing was fascinating so many people, you know, and in the zeitgeist. And that gets back to, is learning free for you, you know? And so I do think most founders have this fascination. They know they're also competitive and, and some of it may be money. They know that if they can surf a new wave faster than the rest of the other people, that there's reward for that.

As we've been talking, like, it's, it's ironic that, like, the same AI that threatens job stability, like, also, um,

may accelerate self-discovery. And so, you know, in the past, when I would say, enhance the competitiveness of people that, that are able to weaponize... So, like leveling the odds? Yeah, essentially. Let's use it in a game context. Your, your character, if you have AI, you now have extra weapons and, and credits and, like, lives and everything. It's like you're more enhanced than the person who's not using it. Like, it's pretty clear that that is true in our society now. Would

That kind of brings a question, which is very meta, is the concept of information itself. So if you spend 10,000 hours on a craft in the past, you kind of get this label of being an expert on it. Or if you know substantially more about a subject than other people, then you're also labeled as an expert. But if information is accessed on demand, is your acquisition and possession of that information, is the value of that changed?

I personally believe that there's a difference between being able to access it and having learned it and truly understood it and synthesized it in your brain. I like to say that for young people in particular, there's this... super weapon that you can have with learning where, you know, it's a barbell: know the history of everything in your field and know the edge of what's in your field. And the history one's kind of, it's, it's kind of old school, but, but if you study the pioneers of the field and have instant recall about them, you will... One, you'll learn whatever they thought. Two, you will have shown reverence for the field in a way that you think may not matter, but for an elder that might be making a decision about whether to hire you or not, will look particularly differentiating.

And then three, you build this habit of trying to learn and understand what the bedrock principles are in the field. There's a great story in the book where there's this world chess tournament, and they take a break and do a trivia contest. And Magnus Carlsen wins the trivia contest. And you say, is that happenstance or is that, like, for a reason, right? And he did an interview on, I think, Lex Fridman, which I would highly recommend people listen to. He hates rote exercise. He hates the kind of stuff you do in school. He loves and adores the art of playing chess, and that's why he read all the history stuff. And he definitely thinks about it more as an artist than a robot, you know, if you will. And so I think that him knowing the history of all the famous chess plays and how the best masters learned things and did things, yeah, I think having that in your walk-around brain is very different from being able to do a prompt and pull it up when you need it. Yeah, yeah. No, I—I've felt that even in my own experiences, that, you know...

There's so much information in front of you, but it's a completely another paradigm to actually process and, like, download essentially the information, internalize it, and understand what it actually means. Otherwise, you're just, like, having information pulled and then you're pushing out without any clear understanding, which I guess wouldn't really help you in the field.

By the way, the other half of this barbell is know what's on the edge. And I'll give an example. Let's say you're a marketing major and you're interviewing at PepsiCo and Coca-Cola or whatever the top people that hire marketing people are. one you you know you're lined up in a slate of interviews because that's what your your career counselor told you at school there's 30 people coming in that are going to get 10 minutes or 15 minutes each if you have instant recall about the pioneers of of the marketing field i guarantee you the 19 other don't like they're just kids don't do that and you're going to stand out secondly if you fully understand how tick tock works you're going to stand out because if someone's in marketing, if there's an adult in marketing that's been in marketing for 20 years, they don't understand how TikTok works.

And one of their biggest anxieties is we need people inside this organization that understand these modern tools. And so I really think learning on the edge and learning way in the past are really these two differentiators that could help anybody in any field.

Now, are there specific prompts or things that, even just on the fly, for someone that is in the self-discovery process trying to figure out what they're fascinated by, you think that could be helpful?

One other reason everyone should play around with AI: the types of prompts that you can make, they increase as you play with it more, like the types of things you could have it do. But you could literally tell it all about yourself. Say, 'I want to go into this new career.' Explain your constraints and say, 'Give me five scenarios that might be how I can move in this direction.' The things that it spits out will be relevant to you thinking about whether it's possible or not, and it's information you don't have today. Like, it doesn't hurt to read it, right? You could ignore it, but I think it—I think you won't ignore it. I think it'll give you answers that help you start to fill in the pieces. It's easy to say no if you don't consider it at all.

You know what I'm saying? Because you can let the impossibility of it just shut off your brain. Yeah. But that's why I say that little itch kind of maybe needs to be there, because you need to go start the exploration.

As an investor, so much, I guess, of what you do is based on—you see a potential technological disruption and the feasibility of investing in that, but then also the risk of it blowing up and then not becoming anything. If someone's in a similar position with their risk tolerance on something, let's just say they do have a family or they have a certain set of constraints, how would you coach people to navigate whether to take on risk or the benefits of pursuing something that's risky versus playing it safe?

Well, the first thing I would say is don't ignore the counterfactual. We often criticize a path without recognizing that not doing it means, okay, well, then you're staying in this role. And so that's not a fair comparison. You have to compare it to... like if you're unhappy in your job, if you have anxiety that your job's gonna be replaced by AI, if going out and putting your resume out there again is gonna be hyper painful, you're not economically stable anyway. You're fearful you might lose that job. I'm just saying staying and doing nothing has its own consequences. So make sure you compare and contrast action versus inaction.

It's a really interesting way of putting it—the illusion of something being safe. And to your point with the Wharton study, I mean, 70% of people are in a place where they wish they could have a do-over, and this opportunity is... I think humans just generally don't like, at some level, stepping into the unknown. I get it. Or the uncertainty.

That's why simply reading about 14 people that have done it makes it more plausible—like, more plausible that, 'Oh, I could study them. I could borrow techniques. I could learn how to do this and be successful.' This disinhibiting part of the journey is maybe the most important first part to get you thinking that it's possible.

Let's just say someone finds what they're fascinated about. They've located something that they're—that they feel like they want to pursue. What would be the next step after that?

Well, I mean, we've talked about some of it, but I'd just immediately start learning. Before you take the jump, start this learning exercise. We talked about maybe profiling 10 people that are successful in that field. Get to know them all. Find a biography, find a YouTube interview, find a podcast. Study each of them for a week and build a profile. Write a Google Document, like, what do you like about them? What do you not like? What makes them particularly special? Like, going through that exercise alone will be a part of this disinhibiting process that will make you think of and imagine what it's going to be like for you to go to that place, and that can be done without ever stepping away from the current job that you're in.

It's a great way to test whether you really have the passion or not.

Now, are there a certain set of skills that you would look for? Let's just say someone pursues something, maybe they start at the bottom or wherever they start on this new journey. Are there a certain set of skills that are—would be universally attractive to people hiring?

Immense fascination. Like, do you know, it's funny. I think that we, um, we have a certain set of rules and, and, um, admiration for, like, athletes and artisans that we just don't apply to other crafts. Like, if you see an athlete that you know, and you hear a story that they train for 80 hours a week, like, that's like, 'Wow, they train for 80 hours a week.' If you hear that a Fortran programmer did that, you'd go, 'Oh, they're a workaholic. What a boring life.' We have different ways we analyze these things, and I think it's unfair. I think that if someone walks into an interview and you're interviewing them, and they are so fascinated by this world that they can name all the pioneers, and they know what's happening on the edge, and you visibly see them smiling, that's powerful.

You would hire someone just based off that? I would be motivated to take the next step and figure out. Yes, I would, and I think most people would. Like, that kind of energy is infectious. Like, people want to be around people like that. Yeah, I think it'd be highly differentiated.

I do. So then, how much does that matter versus...

their ability to do a certain set of tasks for that job well? I mean, look, there are jobs that are very task-oriented, and programming is one of those, like, um, being a physics major, mechanical engineering. You're going to go work at SpaceX. Elon, Elon talks about in the interview process, you know, trying to find out exactly how much you know, and I don't... Like, for those types of things, um, you're going to have to be really skilled in that field to be able to interview into those positions.

But, but, and I, I...

say this again, that may not be true at the first rung at the entry level. There are all of these people in Hollywood, Barry Diller, David Geffen, that started in the mailroom. They literally started sorting mail and found their way up the chain, lots of them. And for that person in that interview, I guarantee you, like, 'Oh, I've loved Hollywood my whole life. I'll take any job to get in the door.' Yeah, they'll hire that person. Definitely hire that person.

And the demand to be with other people, to learn from other people, I think, when everything is so automated, I think, could increase.

I've heard other people make this argument that social skills, networking, personal skills become amplified in a world where the rote automation is free.

And so, yeah, I think that... My next question is really, people usually look at other people as competition, right? And so, there's a very cutthroat type of mentality. Even if somebody is in the office with you, it's just like, 'Well, I don't want them to get the promotion, or I don't want them to get ahead, so I'm going to try to stomp on them.' And so, what do you think of those sorts of attitudes, and what is a proper orientation towards people?

Well, unfortunately, I think they're programmed into that college, industrial college process that I talked about, and, and, and the athletic thing. I mean, we push kids into athletics like crazy, and, and athletics is a zero-sum game. There's a winner and there's a loser. And, and, you know, there's only one valedictorian and all that. And I think we borrow a lot of our memes and metaphors that are in our head from finite games. You know, Simon Sinek wrote this book about infinite games, and he borrowed it from a guy named James Carse, who had written a book called Finite and Infinite Games. Life's an infinite game. Most careers are an infinite game. There's not one winner in the field of dentistry.

There's just not. There's a ton of great dentists and wonderful dentists in the world, like a ton. And so, I think getting out of that finite mindset that it's a zero-sum game will unlock so much potential for you. And I give many examples of people that were able to find like-minded people on the same rung of the ladder you're on, and they create a friend group. And today in the digital age, that's easier than ever to do. You can just use WhatsApp, or you could get more ambitious and do a Slack group or Google Workspace or something like where anytime you discover something, you can make sure these other people know about it as well. And, um, what I have found when people are able to do this, first of all, I've found there's a reluctance to do it, to your point. Like, I think somewhere along the way, we program people to be a little too sharp-elbowed and not to, to have this type of friend group. But what I've seen is it's super powerful if you go do it. And it could be people in your org. I think it's better if they're not in your org because they're going to bring

more diverse experiences to the table. So the group will get the collective learning of everyone there. You will also share a network. So if your network is valuable to you, if you can plug four people together and share, now you've got a network four times as large, which is super powerful. And then it also has the potential to create optionality. Like one of those people may know about a job opportunity that you didn't know about or a technique that you can use in your field or that's used in their company that no one in your company is using. And now you look even better. And then also that group can provide support. And every one of these I found that we talked to, everyone in it, that part's very real. So everyone has a bad day. Everyone feels at some point in time like, 'Oh, maybe I'm not going to make it in this field,' and having this group you can go talk to and be vulnerable. But like, it's hard to be vulnerable with mentors because, you know, there's this hierarchical relationship and you want to only look successful to your mentor, yeah, but to your peers, it's not that way. And so look

In addition to finding those people that are on your journey, they need to be your friends. So they need to pass certain social tests. If it's that sharp-elbowed person that might step on your head, don't put them in your group. Kick them out. Fast, kick them out. They'll just take and they won't give. But if you can find this group and co-learn together, there's a great anecdote in the book about MrBeast when he was 17 years old. And he told this to Joe Rogan, so that's where I heard about it. But he's 17 years old. He's fascinated with YouTube. And he finds three other people that are equally fascinated with YouTube. And they're very lucky to be at the beginning of the YouTube business. And the reason I say lucky is discovering new tricks that make you successful are remarkably valuable at that moment.

And this is what founders do with new technology waves, right? Because if you discover something and can figure it out, then you get to—it's almost like a video game—you get to go right up to the next level.

It's like an early-mover type of thing. Yes.

But because there were four of them, he used a phrase that was very clever. He borrowed Gladwell's 10,000 hours and said, 'We got 40,000 hours because we combined the learning of everybody.' He claimed they were on Slack like 16 hours a day for four years. And he even said they all became millionaires. And if there had been a fifth person on the Slack, he's highly convinced they would have become one as well. It's a very collaborative approach to looking at doing something that you love in your career.

I mean, imagine it in your field if there are four great podcasters that share information.

I mean, they were down to, like, if you listen to this thing on Rogan, they were down to, like, what color is the thumbnail, you know, that goes on the promotion. And that gets back to nuance and details that artisans care about. You know, it's not... It's not like, 'Oh, don't be nice to your coworker.' It's not that kind of advice. It was way deeper than that.

Is there something that needs to be released in order to look at or let go of in order to look at other people that way?

Yes. I mean, you already said it. It's this notion that it's a zero-sum game and only one person's going to get to the top. There's another thing they have to let go of: this silly idea that you have proprietary information in your brain that you can't let go of because then it's going to propel them. Yeah, yeah. I mean, it's—it's just silly anyway. Especially in AI, with all this information out there, the notion that you have this permanent, like, intellectual advantage is foolhardy. And—but you gotta let go of that, too. One good test of whether you really are approaching that the right way is if one of those people gets a promotion or one of those people gets a new job, how happy it makes you feel.

Because I think in the right scenario, you're thrilled. You're just tickled pink. The group's working. That person was able to take advantage, and you should think about them like a teammate or a sibling succeeding.

Is this easier to do if someone's within your own company versus you find them outside?

I think it's better out. I really do. It's diversity. The likelihood that the network expands, that the learning expands is higher. And there's zero chance that they're going to take your job. So I think it's better.

So networking itself is another interesting thing because, like you said, it requires social skills. And I feel like for some people that could be awkward, right?

Yeah, although there are new digital forms like, like, like if you want to be an artisan on some, you know, random field, there's probably a subreddit out there, right? And you can get in there with, with less social skills and start communicating and sharing. Once again, you need to be less concerned about some type of proprietary advantage you have because the more you're willing to be vulnerable and put ideas out there and share and, and the, the better chance you're going to connect with others. But, but, you know, I saw some crazy stat like, I think it peaked, but like the number of people over 25 that found their, their mate online, it went up to like 40 or 50. Like, there's no reason why your, your business network wouldn't be the same way. Yeah, LinkedIn, I mean, there's all kind of amazing tools where you...

I mean, the word that you just said that struck me is vulnerability. And so at what level in the professional space do you feel like people should be truly, I mean, there's so many different levels to this of how vulnerable you should be with your colleague versus your person who's your boss versus a mentor, all of those things.

I mean, look, I think with boss and mentors, it's difficult to go in and say, 'Oh, I'm...' you know, it depends how good they are. Like if they're really good, you could actually be quite vulnerable, but— Like about your emotions and stuff? Yeah, yeah, if they're really good, like if they're really good leaders, but I don't think, I think that's maybe five or 10% of leaders. Like you'll know, you'll know, because you'll have that trust. Like if you have one of those, you'll know. But it doesn't matter. I think this whole idea that you're running a race, a zero-sum race by yourself, I think will prohibit you from being wildly successful and also will make it harder for it to ever feel like fulfillment.

Even if you win, I think you don't feel the same. And that comes more from just my experience. And there's a story in the book about Bobby Knight, and most people probably think of him as the angry man that threw the chair. But if you study both how he came up and then how he developed other coaches later in his career, he probably has the deepest coaching tree of anyone, of anyone, which means he let people come into his orbit. He shared all of his knowledge and let them go out of his orbit. And he didn't think about them as being disloyal or anything like that. He loved sharing. And on the way up, in his biography, there's an example of a coach sharing defensive strategy with his coach that he notices, and then his team ends up beating that team.

And he has the intellectual conversation with himself, 'Should that not have happened?' and then says, 'No, that's part of how this works,' and came around to the other side, which I think is the right answer.

What's the difference between information that you can uniquely get and learning you can uniquely get from another person versus what's available through AI now?

I think a lot of that comes down to nuance and how new the information is. I mean, at least AI as it exists today—and we'll take superintelligence off the table for the point of this conversation—it is synthesizing what's in the public record. And so things that are novel, it doesn't know about. And that's an area where I think the humans figuring things out is especially interesting. And so that's one area that's certainly different. And then, I mean, there's a whole bunch of soft skills that matter in being successful in any field. I mean, AI may tell you what to do, but I don't know that it will convince you on how to personify it. Danny Meyer, the great New York restaurateur, his book, Setting the Table, is all about hospitality.

And one of his protégés has a top-selling book called Unreasonable Hospitality. And there's nuance in that that I don't think you get from AI. I think you have to feel it.

Yeah, from another human being.

Yeah. Or practice it and see it work in a way. For it to really come alive in your brain, I think it's different.

So when it comes to mentors and then even people that are farther ahead of you, bosses or whatever, I mean, that could be like another potentially awkward point of, "How do I get the attention of a mentor? Will they even want to mentor me? Do I have to pay them?" How would you advise someone to go about that process?

So I think most people make a huge mistake on mentors. They shoot for the top and fail and say it didn't work and that's it and then done. And they get way too greedy on who they try and cold call. Especially there's some really ambitious young adults, which I give them credit for ambition, but they overshoot. And they need to be more nuanced in that activity as well. What I recommend is you divide mentors into two groups: aspirational mentors and then real mentors. For the aspirational one, the exercise I said that Danny did—he profiled 10 people that were changing the restaurant world. This is right when he started and he kept a journal on each one of them. And, as I said, you could do that as an exercise to maybe see whether you want to go into the field, but you can do it the minute you start in the field.

So keep a notebook or a digital notebook or a Google Doc or whatever on these aspirational mentors. If they're ever on a podcast, find a way to have alerts. You want to learn from them. By the way, if you try and cold call them today, they're going to say no, so that was a mistake. But if you're in the field for five more years or 10 more years and you have a chance to meet one of them and you've been studying them the way I just said, the chance that you're going to have a successful interaction is much, much higher. You're going to know more about them. You're going to be able to bring up something relevant. You're going to be able to thank them for teaching you about the field. And then, so that's the aspirational.

I think that's an easy one. And once again, when you say "aspirational," how high are you talking? Just someone who's a leader in the field who's part of why you're drawn to go into it.

So is that like you're a high school basketball player and you want to talk to LeBron James?

Yeah, but you don't talk to him. You just study him. For now, I'm just saying for now, Danny Meyer literally mapped out: these are 10 people who are changing the restaurant industry in a way that I find interesting and are part of the reason why I'm drawn to this field, and he studied them. That's all I'm saying. And I want to... pound the table again, although he told us not to touch the table. The ability to do that today is off the charts, like, better than any time in history. There's more information available and more ways and more media forms. For real mentors, just cool your jets, like, come down a few notches. There's someone that's two levels above you on the ladder that's not four, who maybe no one's asked to be their mentor before, and the sheer gesture of recognizing that they know more than you and that you respect what they've achieved will be so flattering to that individual that the odds of the yes are 10 times higher.

No, it makes total sense.

And people always overshoot. And so just don't shoot as high. Probably try and target five. Don't try and find the perfect mentor. Find people that spike particularly well on a dimension or characteristic that matters in that field. And different people will have different superpowers. Um, and don't shoot so high. And, and I give in the book a lot more kind of details about how to come to the meeting and how to prepare and how to—what to ask for and what not to ask for, like, just so that your chances of success are higher. Is there a risk in sounding transactional to, to somebody when you reach out to them, like, coming off of, like, 'I just want to get something out of you'? Or it's like, 'Yes, but I talked about studying the history.'

If you walk in with knowledge of the pioneers of the field and show this reverence and think about it, if you can convince them that you view that field as an artisan, you're not going to have that problem that you're talking about. If you look like you're a climber with no... What's the word I'm looking for? With no... fascination, really, with the art or craft itself, you're going to have the problem you're talking about. So much nuance. There's a lot of nuance.

In these, like, personal interactions.

There is.

And I feel like the nuances, in some ways, make or break whether you'll be successful in the endeavor.

It could be, but one thing that is a solve for most of those human, nuanced things is authenticity. And this is where I go back to: if you really love—like, love is an interesting word—if you love the idea of being successful in this field, it will show. It will affect your—how you show up emotionally in those meetings. I have zero doubt about that. So, I was thinking about, you know, we're talking about mentors...

The other place that feels like authenticity can be a little fragile is in the hiring process. I once heard someone say, 'A job interview is a conversation between two liars.' The candidate over-exaggerates, the company oversells, and everyone is essentially performing. How much do you think that's actually a true depiction of reality?

I wouldn't be that cynical. I do think that the candidates are in a very performative mode. And there is this tension in the air that doesn't feel great, I think, probably from both sides. One of the reasons I wrote this book was a reflection on both undergrad and graduate school about how much I hated the traditional college hiring process where you line up in a room. Everyone has their resume. You all get 15 or 20 minutes. There's 30 of you. You got to stand out next to everyone that's just like you. And it seems so suboptimal to me. Now, I recognize why the schools have to do it, because they have to mass produce some kind of outcome. But the individual doesn't have to do that. And many of the people I cover in the book, many of my friends, quite frankly, made themselves a candidate of one and created a job opportunity on their own that wasn't through a job opening post, interview session, get the job, which is how most humans think about finding a job.

And so, um, I use a phrase in the book, you know, 'make yourself a candidate of one,' and I talk about how to really differentiate yourself in that way. Um, but especially for entry-level jobs, people will hire based on energy and emotion, as we already discussed. They just will. And so I hate—I hate the classic interview channel so much that I do think you can optimize yourself with this knowledge of the pioneer stuff we've talked about, true emotion and passion, understanding nuance. All those things will help differentiate yourself. But I hate the concept of it, like the whole industrial side of that way of getting a job.

Yeah, because I mean, people apply to jobs online and they have—they see 700 other people apply to this job. It's probably a lot of one-click buttons and not the level.

Oh, the Indeed stuff is just crazy. Like, you know, you're just—you're everyone's clicking boxes and no one knows.

It seems almost impossible, that it's like a needle in a haystack that you would actually connect or be hired through that way.

The thing I thought about, even at the time, way before the concept of this book ever came up, I literally said to myself, 'What are the odds that the company that I ideally want to work for is interviewing at this campus?' It's a low probability. But that's how they tell every college kid to get a role. And I think if you can be more creative about how you go identify a place where you might possibly work and enter through the side door... How would you go about doing that strategy? Well, I mean, a lot of the techniques we've talked about you could use for employers, as I talked about mentors or aspirational mentors. You could use AI to help you identify, like, 'Oh, I want to find a job at an entry level in this field I love.'

What are some great places to start? Or where are the types of organizations people love doing that? And then you study those companies the way I talked about studying these pioneers. And then by the—at some point, you've identified an individual in that company that you might have a connection to, and you're sending them a letter and say, 'I love your company so much, and I aspire to work there so much. I'd love to, if I could get 20 minutes of your time—here's how much I know about the field. Here's why I know your org is the best place to go do that. And I just want 15 minutes of your time to hear about the best pathway for me to possibly find a job there.' And there's an awesome story in the book about Tony Fadell, who—who decided—Tony Fadell created the iPod.

He was head of engineering for the iPhone and created Nest. While he was in college at Michigan, he fell in love with Apple as a company, and he had read an article in Rolling Stone magazine. I went and found a copy of the magazine as I was writing the book on eBay, a perfect copy, and I've gifted it to Tony. And I actually happen to know the guy that wrote the article, but in that article, five of the top people at Apple were leaving to go to this company that Tony had no idea what it was called, General Magic. And if you read the book, the amount of effort Tony put into getting inside of that company, I don't... Then part of this goes back to whether you're really passionate, want to tilt against something this much.

Yeah. But he... knocked on the door forever and finally got in. And for your listeners, there's an amazing free documentary. This company he went to is called General Magic. It was a massive failure, but there's a brilliant documentary. All the people that worked there went on to do amazing things. And being inside of that org, I think, was part of what helped propel Tony to greatness. But the dogmatic way he went about getting inside will be inspiration for anybody that might want to create a bespoke job path versus the traditional way. And there's massive lessons to be learned from failure. We study success so much. It's a great, great, great episode. General Magic.

Yeah, I mean, it seems like in the coming age, that level of pursuit and determination, I feel like probably is going to stand out as one of the things more than anything. Because, I mean, even on LinkedIn right now, I mean, I get a lot of generic messages. I think a lot of emails are going to feel generic because of AI. And they're all going to have this certain type of formula. But you can't really replace that type of relentless pursuit.

Noise is going to go up. Yeah. And that's where we had already kind of both agreed that human connectivity, the value of high-quality human connectivity may really stand out more in a world where the perfect email is always at your fingertips.

So, you know, on the back end of this, in terms of someone's, you know, I just said relentless pursuit, but in terms of someone's time commitment, the hustle to the... though actually what's required to live out something that you love and find something that you love, especially in today's climate, what is a realistic expectation of what someone should expect?

I'd go back to something I said earlier, that if you know people who are in these areas, they love the exploration and the learning so much that it doesn't... I don't know the exact number, maybe it's 50 hours a week, maybe it's 60, but none of those people feel like it's that, because it's too much fun to them every single step of the way. And so I'm a little hesitant to jump at the question because you get back to this workaholic mentality. And how hard does the greatest ballerina work? The greatest painter, how hard do they work? People in those fields, they have this idyllic notion of hard work. And I think it should be that way. If you met a pastor that worked 80 hours a week, would you think that was good or bad?

You know what I'm saying?

I think part of it is like, I mean, there was so much that was made 10 years ago about, you know, Marissa Mayer came out and said the 130 hours a week type thing about working as the Yahoo CEO. I think, honestly, maybe it's a question about, and I don't even know if this is the right word, but balance, or how do you juggle the different responsibilities of life and how do you do this in a way that's like... faithful and in a way that is actually going to lead to a destination that you would like.

This is my belief as someone who had a very successful career in a very intense, competitive industry. If you love what you do, you get energy from your work. If you don't like something you're forced to do, it saps energy from you. If you—if there's some tasks you don't normally do that you have to go do for eight hours a day, like, you get done and you're deflated and you're exhausted and you're like, 'I need a drink,' or, 'I need to go watch—zone out and watch TV,' or whatever. If you love what you do, that doesn't happen. And I don't know all the physiology that causes that to be true, but we all know people that are bouncy about what they do. And so I think they're able to be more present for the, the, the other aspects of life because they're not exhausted by what they're doing, what they're doing.

Yeah. And then they're able to be more present in, in those moments and show up more. So I, I do think, I think it actually helps with work-life balance in an odd way, um, because you're not, you're not coming home like Archie Bunker.

So let's just fast forward five years. Imagine someone who takes everything we've been talking about seriously. How different does their trajectory and their life look?

By the way, I've already got these stories. So part of what motivated me to write the book—the original video presentation is still out there on YouTube. I met—as part of marketing the book, a guy reached out to me who saw the original video, who had been a teacher his whole life, but he was fascinated with football. So he always begged to coach the eighth-grade team or the Pop Warner team or whatever. He always was fascinated with football, and he saw that video and said, 'One day I'm gonna have a career in football.' And he—I mean, this is so modern—he built a podcast. He started studying offensive football plays. He wrote an application that allows you to experiment with different football plays and to see all the historic football plays.

He's now a full-time football analyst. He's known by many of the great public football commentators. They follow him on Twitter. He has hundreds of thousands of followers, and he's giddy, and he's thankful that that helped give him the permission to go do this. And you can see, your audience, I'm smiling in the end because I love—the truth be told—I'm a closet American Idol fan. I've watched every episode. And this notion that someone can be discovered and then rise, something in my brain is wired. I get kind of sentimental about those things. And if I can help any number of people achieve that, it's going to make the days I have left on this planet much, much better. That's why I said I hope to find people with this little spark or itch and then help turn that into a wildfire.

I don't necessarily have much ambition to tell the cynical person who's just angry that they need to go do this. I'd much rather help the people who have a little bit of a desire to head in this direction. I'm also starting and launching a foundation. I've already set aside the money, but I'm going to give $105,000 uh grants a year to people who want to chase their dreams but maybe a little stuck financially and need a little help to get there and so i'm putting together a team that's going to analyze the applicants and uh and we'll see where that goes i don't know where that'll go but i thought that's incredible i thought it'd be a fun thing to do alongside of this and some of the pushback i get like when i talk about it is what if someone's stuck yeah and so we're gonna that was a lot of the questions yeah yeah we're gonna go do this and see if it can

can help. Running Down a Dream, RDAD.org, is the website for the foundation, and it's already up. So, you know, closing word, you know, if you zoom all the way out, um,

If there's one thing that people are dangerously underestimating about the coming age—consider everything we just talked about—what would you say that is?

I feel like they're overestimating—you didn't ask that question, but they're overestimating the gloom and doom. There's this great book by Matt Ridley called The Rational Optimist, where he highlights that the exchange of money and the exchange of ideas is what's led to the most prosperity in every region. And so there's a simple construct of two farmers meeting at the market. And one of them knows how to get twice as much out of their crop as the other. And they share that. That's a zero-cost transaction, but now the other farmer's making more. Like, and, and I've only—like, that's, that's the, the—you know, Xi Jinping brought 900 million people out of poverty in China by introducing, you know, free trade and capitalism.

And I've only seen that happen. Technology allows us to create more things at lower prices than we have before and solve more healthcare problems and all these things. So gloom and doom, I just—I don't think it's going to play out that way. Yeah, well, no, that doesn't answer the question.

I think people are underestimating, potentially, based on what you're saying, hope.

Yes. Possibility and potential.

Yes, yes. And unlocking human potential, yeah.

You spun it in the way I wanted to and couldn't do. Yeah.

Yes, that's what I would say. I think it's going to be okay.

Yeah. I really think it's going to be okay. And the things that humans can accomplish will increase with these tools rather than decrease if you start to be fascinated with them and play around with them.

Well, thank you for being here today. Thanks for having me. Appreciate the conversation.