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 skill set 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 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 road map for living well. The podcast is where we slow down and examine one part of that road map 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. 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. So 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 6 seconds. So 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?
Oh, 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, you know, 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. Like, I don't think that's going to happen. And so 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 and 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 the arguments off the table because there's no point in vilifying it. It's not a helpful exercise to help her get to where she needs to be.
Yeah. It's just it has 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 Dario Amodei, all making these public statements about like a huge job loss.
Can I also though frame that like they're also raising billions and billions of dollars for their company. They're leading the biggest secondary transactions for their employees in the history 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 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 about AI anxiety in China that are a fraction of the anxiety levels that they have here in the US. 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 US are the biggest doomsayers. It's radical. But 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. That doesn't mean that some didn't lose their job. I just think we're prone to getting overexcited about these things as humans.
Yeah. I think 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 venture capital. Is that actually happening?
Yes, I think that's actually happening. Now look, I don't want to suggest that... I want to be very clear. I'm not making the argument that this won't disrupt certain jobs. I think the paralegal space, it 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 the 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. 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. 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, a prompt away. Like Wikipedia was pretty cool but this is even that on steroids.
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, 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 locally. I've met a lot of local entrepreneurs that 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 like.' They're just blown. They're giddy. They're happy, giddy about this. And one of the tenets that I attach to highly successful people is continuous learning and learning 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, the amount of knowledge that's right there in front of you one click away is almost staggering. It's unbelievable.
I mean, I totally agree with you. I think I had a moment last year where I was like, 'Wow, this deep trove of information.' Like I would have had to pay someone like $10,000 an hour for certain things. Yes. 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, 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 got a job? Because the reason I bring that up, well, first of all, I think that our society 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. It is an instinct. I have three children. There's an instinct to worry about them, especially from a financial economic stability standpoint. But if someone ends up... and there's some data from a 2023 Gallup poll that suggested over 50% 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. You're not doing that. 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. You really might get run over. And so 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 rechannel the anxiety you have about this current job you don't love, having risk to explore what's possible and go into a field where you have the right kind of passion where I think you can outrun 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 rapid. I mean, you have the internet which pops out in the '90s and then social media and then all the smartphone and then all the apps that are put on smartphone. Now you have AI which is like condensed three-year period. And so how do you see this moment versus previous moments? Do you see this just as a next chapter in the story or do you think that this technology is different than the other technologies that disrupted?
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. And since, you know, 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. And I don't recall any of those having... I mean 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 disrupt them. And the other thing is I think technology in the previous waves threatened mostly blue-collar jobs and this is clearly with paralegals and computer scientists at the forefront. This is the first time I think white-collar jobs have been threatened which I guess for the intellectuals that's a new reality. So the investment community, and they're always prone to hyperbole so 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 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 or the cognitive labor shifts dramatically, what do you... I mean there's been much that have been made about like megatrends. What are you anticipating like the fields will morph into or changes or things?
Well, so I think you got to segment the word knowledge into a couple 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 counting 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. Another, the paralegal one, you're doing searches, you're summarizing anything with language, quite frankly, and I would say customer service and paralegals. LLMs are really good at language and sorting and synthesizing and identifying like search type query things and those are threatened. 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 is 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 scientists, it was always about understanding the potential, coming up with the proper algorithm structure. It was never about the rote work. But the rote work is the thing that's most in danger. If you are hyper intellectually curious in your field, 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, you've already... AI has been out for a couple years now. You've already played with it. You already know what it's capable of. If you're the most cog, 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, you know, 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... well, you did the large study with Wharton. 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 their work.
Right. Yeah. So this Gallup poll which anyone could go find from 2023, that like 23% of people considered themselves highly engaged or passionate about what they do and some number north of 50 were kind of meh. And then there were like 18% that were actively like angry and messing up their work environment. But none of that sounds great, right? You'd like those numbers to be better. And the question is how do you end up in that place and why? And somewhere along the way while we were studying the latest academic work, we on a whim, 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 10 said yes. And we redid the 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 10. And you know there's this great book by Daniel Pink called The Power of Regrets. 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, move on.' They don't sit there and ruminate for the next 30 years about this mistake they made. But the thing they never tried, that itch that was in the back of their mind that '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 like pushing myself forward in time. And 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 time across 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 seemed 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 he went out 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. The 80-year-old self said, 'Life is short, take the chance. You can always go back.' Like what, David Shaw's going to have him back, right? It's kind of a one-time shot. And he calls that his regret minimization framework, which he admits 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 short time is by using one of these exercises, they might have a better perspective about whether they want to take the risk to try something else.
Yeah, I think that is... yeah, it's so relevant that the fact that people are in these jobs that they are not happy with because that's another way of looking at the moment that we're living in. 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 stuck in things that they didn't love doing. And so if you hate what you're doing for so many hours out of the week, then this becomes like a pathway. I think the thing that people wrestle with and I've wrestled with in the past 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 that's higher than that of like, 'Oh, I would love to do something that I'm really fascinated by.' It gives you fulfillment. 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, you know, 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 a hundred 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 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 developed a newsletter and a podcast and wrote books and 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 and he was talking about this whole thing of like work becoming optional or will become optional and any product or service that you want you can have and so these futuristic scenarios that were painted. But when you actually break down how many different fields that there are, it's so enormous. Like 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 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... it would require so much.
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, you know, someone that is taking an income from the government and not doing anything, 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? Is 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 was just completely stripped away from someone's existence. Even if they were getting financial support, it was just like they're just sitting around all day.
No, I don't think it works. Yeah, for a variety of reasons. But I agree with your premise that like 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. Like there's 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 system of record. There 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 there's a ton of rhetoric out there today. A ton of rhetoric. And 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. But people are taking it too far.
Yeah. I think people just hear these statements but then the kind of logical thinking part of their brain of teasing out these scenarios and then replicating every human task that possibly exists across every single field. 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 super intelligence. You don't believe that either?
No. No. And there are plenty of AI researchers who don't believe it. 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 is... what's like the best long-term, if you have practical... 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 this thing that they're so obsessed with that this continuous learning 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 on 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 battlecard scenario, also go study five to 10 people that have made a success in a career like that. They do podcasts. They do interviews on YouTube. Go listen to them. By the way, if any of that feels spurious, cross that card off like you should want to go do this. You understand what I'm saying? 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 would 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. I keep going back. If you're high agency, man, this stuff'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 Atkins enrolled in a free cosmetology class in LA offered by the city and became the top hair stylist 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, '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've taught our children so much, 'You got to get into Harvard and Yale.' No one would say go take the $200 occupational course offered at the community college. No one says that. It's not pushed as a way to get to the top.
I think that piece though is one of the things that feel uncertain to people 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 the past 50 years. But I think there's a lot of uncertainty that people feel about like 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 are your thoughts about...?
I think that anxiety is mostly in these safe jobs like where we cram... 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 we 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's 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 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 The 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 that 'oh I've invested all 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... in Dave Evans' book, he says after 10 years, less than 50% of people are still in the career 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 they feel stuck on it. 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 like dead ends? So even if you became fascinated by something, are there certain paths or careers or trends that you see like probably shouldn't?
Well, paralegal... 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... because there's a lawyer that I've gotten to know, Neil Katyal, who's done a TED talk and but last week, you know, he got this victory at the Supreme Court. He was the one arguing in front of the Supreme Court on the Trump tariff situation. Now, if you know Neil, I guarantee you he thinks about being a lawyer as a craft. I'm certain of it. But if you ask the average human, is being a lawyer a craft? They'd probably giggle or laugh or say no. And so I think in almost any field, you can think about it that way. 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, 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.
You know, obviously you had a lot of involvement in Uber. So someone like 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, is that fascination that's driving a person like that when they're a founder entrepreneur in a company that they're just pouring into this thing and obsessed a lot?
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 am I 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. Like 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 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 Clawbot in the past three weeks. But I bet you most the top 40% of founders in the world launched a Claw in the past three weeks. They couldn't not do it. You know what I'm saying? They just couldn't not know why this thing was fascinating so many people, you know? And that gets back to this is learning free for you. And so I do think most founders have this fascination. They know they're also competitive 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, it's ironic that like the same AI that threatens job stability also may accelerate self-discovery. And so, you know, in the past...
Well, and I would say enhance the competitiveness of people that are able to weaponize it.
So, like leveling the odds essentially.
Let's use it in a game context. Your character, if you have AI, you now have extra weapons and credits and lives and everything. It's like you're more enhanced than the person who's not using it. It's pretty clear that that is true in our society.
Now that kind of brings a question which is very meta is the concept of information itself, right? So if you spend 10,000 hours on a craft in the past, that has 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 like 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...
Know that's 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 old school. But if you study the pioneers of the field and have instant recall about them, 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. Yeah. 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 artisan than a robot, you know, if you will. And so I think him knowing the history of all the famous chess plays and how the best masters learned things and did things. I think having that in your walk brain is very different from being able to do a prompt and pull it up when you need it.
Yeah. No, I've felt that even in my own experience is 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 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're lined up in a slate of interviews because that's what 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 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 TikTok 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 knowing 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 problems or things that even just off the fly for someone that is in a 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 could move in this direction. And the things 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 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. But if you... 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 risk. Like you see a potential technological disruption and the feasibility of investing in that but then also like the risk of it blowing up and then not becoming anything. So if someone's in a similar position with their risk tolerance on something, right? So 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. Like 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 what... If you're unhappy in your job, if you have anxiety that your job's going to be replaced by AI, if going out and putting your resume out there again is going to be hyper painful, you're not economically stable anyway. Like you're fearful you might lose that job. Like 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. Then this opportunity is... I think people, I think humans just generally don't like at some level stepping into the unknown. I get it, or the uncertainty.
That's why Seinfeld 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 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 just immediately start learning like 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, you know, 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 and it's a great way to test whether you really have the passion or not. Now are there certain set of skills that you would look for in... let's just say someone pursues something maybe they start at the bottom or wherever they start on this new journey, are there certain set of skills that would be universally attractive to people hiring?
Immense fascination. Like do you know... It's funny, I think that we have a certain set of rules and 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 trained for 80 hours a week.' If you hear that a programmer did that, you'd go, 'Oh, they're a workaholic. What a boring life.' Like we have different ways we analyze these things, you know? 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, you know, yes, I would like... 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 being a physics major, mechanical engineering, you're going to go work at SpaceX. Elon talks about in the interview process, you know, trying to find out exactly how much you know. And for those types of things, you're going to have to be really skilled in that field to be able to interview into those positions. But and 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 mail room, you know, they literally started sorting mail and found their way up the chain. Lots of them. And 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 like 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 like people usually look at other people as competition, right? And so there's a very cutthroat type of mentality like even if somebody's 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 to...
