Modern Wisdom - #1071 - Bill Gurley - If You Hate Your Job, This is How to Start Over

Episode Date: March 14, 2026

Bill Gurley is a venture capitalist, general partner at Benchmark, and a former Wall Street analyst. How do you find work you actually enjoy? So many people warn about the jobs they hate and the dreams they never chased. But turning passion into a career is harder than it sounds. So how do you reinvent yourself and build a life where work feels meaningful instead of miserable? Expect to learn why most people end up having careers they regret, how to build a framework for regret minimisation, what people do that achieve success in their dream career, how to know when you’re plateauing versus when you’re just bored, what great mentors actually do that books and podcasts can’t, if someone can learn to love the grind or if it is something that’s innate, how you know if you’re in the wrong field versus just in the hard phase of the right field and much more… Sponsors: See discounts for all the products I use and recommend: ⁠https://chriswillx.com/deals⁠ New pricing since recording: Function is now just $365, plus get $25 off at https://functionhealth.com/modernwisdom Get up to $350 off the Pod 5 at https://eightsleep.com/modernwisdom Get 35% off your first subscription on the best supplements from Momentous at https://livemomentous.com/modernwisdom Get up to 20% off the leading longevity and cellular health supplement at https://timeline.com/modernwisdom Extra Stuff: Get my free reading list of 100 books to read before you die: ⁠https://chriswillx.com/books⁠ Try my productivity energy drink Neutonic: ⁠https://neutonic.com/modernwisdom⁠ Episodes You Might Enjoy: #577 - David Goggins - This Is How To Master Your Life: ⁠https://tinyurl.com/43hv6y59⁠ #712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: ⁠https://tinyurl.com/2rtz7avf⁠ #700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: ⁠https://tinyurl.com/3ccn5vkp⁠ - Get In Touch: Instagram: ⁠https://www.instagram.com/chriswillx⁠ Twitter: ⁠https://www.twitter.com/chriswillx⁠ YouTube: ⁠https://www.youtube.com/modernwisdompodcast⁠ Email: ⁠https://chriswillx.com/contact⁠ - Learn more about your ad choices. Visit megaphone.fm/adchoices

What got you into thinking about the idea of career regret as somebody that's had a very seemingly successful and fun career? Why did you think about it? I used to, so I spent 25 years as a venture capitalist and the four years before that as a sell side analyst on Wall Street. And through that process, I started writing as a way to differentiate myself. And so I was an early blogger. It was actually a fax. That's how old I am when I started. and I got in the habit of when I had ideas jotting them down and then, you know, either developing

them, a lot of them ended up just undeveloped. But if I developed them, they would become a blog post. And there was a period in my career where I was reading a ton of biographies. And I finished this third one and saw a through line with these other two from people that were in wildly different fields. And I jotted those notes down. And that thing kind of simmered and breathed. and took on a little bit of a life.

And I got asked by the dean of the business school here in Austin University of Texas to talk to the NBA class one day. And I was like, can I do this? And he said, sure. So I pulled it out and developed it a little bit as a PowerPoint presentation. Anyway, they posted that on YouTube.

A few people noticed. Some people that have been on your show, James Clear noticed. And he posted it on his website. And people started prodding me to develop it as a book. And a few years ago, I decided to begin retirement as a venture capitalist. It actually takes a while, unfortunately. And in that window, I thought about doing this.

I thought about doing a book. And a lot of people wanted me to do a book. A lot of people wanted me to do a VC book or an investment book or a tell-all book on the Uber experience. And I was more drawn to this idea. And a few other people prodded me who said, you know, like go do. And it felt more authentic. it felt like something that could have a bigger impact.

And I was drawn to that. At this moment in my life, I was drawn to this particular thing. So I spent like six years working with a co-writer and researcher developing, and developing it further and making it this way. But you use the word regret. We did, along the way, I launched a survey on survey monkey that said, if you could go back and start over, would you do a different career? and seven out of ten people said yes.

And I eventually took that to work in people analytics, and they did a more scientific version of a much broader audience and came back six out of ten, but very similar. And that notion of career regrets interesting. I had the opportunity to talk to Daniel Pink, who you may know, who wrote a book. It's been on the show about regret. About regret.

And in that book, he says the biggest regrets people have, and he showed me a graph. actually gets worse as you get older towards end of life are regrets of inaction. He calls them boldness regrets. It's what you didn't do. Like humans are great at forgiving themselves, made a mistake, learn from it, won't do it again. But they ruminate about what they didn't try. And so I, you know, I've thought about this long and hard now since I've been working on it for six years. I fear our current education path has become a bit of a conveyor. about people like we're pushing these children

into this meat grinder. And we're pushing them towards jobs that are typically called safe jobs, at least before AI. And I think they're learning to grind. That's what Angela Duckworth's been saying. Now, you know, the perseverance part, we've taught them, but if they don't have the love for it,

it turns into burnout. And so the purpose of this book that I wrote, is hopefully to give as many people permission to go do what they want in life, you know. And look, I'm sure it won't touch everybody. But if there's a subgroup of people who read this and have the conviction that they can go succeed in this thing they love, I think that would be a huge impact on the world. Like, I think the people that do that are the people, you know these people, like, that are just love what they do.

And not only are they more successful, but I'm not only are they more successful, I think they radiate a bit, you know, and spread positive energy. Well, they're mimetic as well. They become a role model for other people. That's right. Go and do. Oh, he took a chance on that thing that he wanted to do. And wow, it didn't work out.

And his life didn't blow up. Or it did work out. And he's really happy. That's right. Thinking about the fact that we seem to regret in action, boldness regret. Yeah. Have you reflected on why you think that is, what it is in the human mind that causes us to prefer dis-

decisiveness over... I was hoping to bring up one of the many biases I've read about in all the behavioral science books, but I'm going to go to a different place, which is I think we ruminate a lot. Like our brains, you know, constantly are replaying things in our minds. And maybe that's what dreaming is too.

But I think because of that, it's very easy to imagine these what-fs, to build a story, especially a positive story around the what if I, that didn't get done. And then you compare that to your current life. And unfortunately, that can create anxiety. But I do think that might be part of it. You'd be familiar with the Zygarnic effect. I'm not. Tell me.

Oh, cool. So it was a psychologist who began studying waiting staff. And they realized that these waiting staff had unbelievable recall while the tables were still open. You know, you've ever been to a restaurant and you see some waiter come up and they're stood, no pen, no pads, no iPad, hands behind their back. And they go, this guy's crazy. Like, he's insane. I'm definitely going to get something wrong.

And sometimes you might, I'm going to, we'll take the sprouts by extra bacon, no, no goat's cheese. But you want to just see if, oh, all right, Mr. No, no, no pad. And the study ended up finding out the Zygarnica. which is an open-loop, closed-loop bias that exists inside of the human mind. While the tables were still open, the servers were able to recall what the orders were very closely. And as soon as they went, nothing at all. You know, a perfect example in almost everybody's life with this.

I'm quite bad at this, actually, but it still holds true. Hotel rooms. I'd say that you're moving from city to city to city. You're not bad at remembering the hotel room of where you are now. Yeah. But if I was to say, where did you, which hotel rooms are? room did you stay in two hotels ago? I'd give it 7.35. I don't know. I have no idea.

It's the same reason why cliffhangers work at the end of TV shows to get you to watch the next one. Yes, yeah. The open loop, the human mind abhors an open loop. And I get the sense that I see what you're saying. When it comes to boldness regret, the main thing that you have is an open loop. Now, the human mind abhors open loop. and uncertainty and ambiguity so much that we'd rather imagine a catastrophe than deal with the uncertainty. That's what a lot of anxiety,

sort of future projected regret kind of is, right? I don't know what's going to happen, so I'll imagine the worst thing, and at least for a moment I have certainty, even if the certainty is horrible. And this is the same thing, I think, in some regards, but in reverse. What could have happened?

Yeah. What could I have done? And there's an interesting way to flip it on its head when Jeff Bezos was trying to convince himself, to go start Amazon. He had this incredible job at D.E. Shaw, and David Shaw didn't want him to leave, so he was trying to talk him out of going. And Bezos has this thing. It's on YouTube. You can go watch it, but he self-proclaimed it was very nerdy, but he called it the regret minimization framework. And he just imagined he's 80 years old and was trying to get advice from his 80-year-old self

about what to do. So he, like, put himself in that future place where he might have that that boldness regret. And in my own career, people, I had two different jobs I started and then switched before I got into venture capital, which was definitely my dream job. And in both of those cases, a couple years in, I paused and reflected, and I only thought about this as I've been promoting the book, I paused and reflected, do I want to do this for 30 years? And was able to like fast forward that in my brain. And I was unhappy with that reflection. Which encouraged me to think about what's next.

When it comes to the regret minimization framework, which I love and I kind of can't believe isn't bigger. I'm aware it is among people that read the sort of stuff that you do or maybe I do. Yeah, yeah. It is a really wonderful idea. And I guess Jeff's got other stuff. that he can be well known for. So perhaps, you know.

Well, it's actually quite synonymous with the, the, one of the seven habits of highly effective people begin with the end in mind. It has a similar kind of. When looking at the regret minimization framework, what are the things that, what are the common pitfalls that you've seen people do? Even both inside of their career and outside of it,

you must have reflected on this a lot. Yeah, I have one thing that I think, especially with, with the modern young people, I think one problem that I think exists. Because we've built this, I called in my book a conveyor belt, Jonathan Haidt called it a regret, or a, I'm sorry, a resume arms race. We've built this, this pipeline for these kids that's so intense. I think when they get to their first job, they feel like it's the result of all this investment. And they feel like tweaking any way away from that is is is is throwing away the investment does that make

sense like a loss aversion type thing yes yes yes yes I invested all of this to get to this college to get to this degree and if I move away from that did I just waste all that time and um you know this is despite the fact that in in there's a lot of studies that have been done like I won't get the numbers exactly right but like five years after college, 40% of people are no longer working in the field that was their major. And that number gets bigger at 10. But it doesn't mean that they don't feel trapped or that that number might not be higher if they didn't feel trapped. And when I mentioned this to young people, there is this weight. There is this weight they feel, like an obligation to, especially maybe they didn't pay.

Decisions that they're locked in when they were 17. Yes. Well, and that's another thing. And when, When I was younger, the colleges wouldn't let you declare a major until the end of your sophomore year. Many schools, you have to apply to the major now. So we've moved the decision of what major are you going to pick from the end of your sophomore year to the end of your junior year in high school. Like, that's, you know, three years forward and less time to, there's a lot of people, a lot of smart people that just say we don't allow children.

enough time to explore. And, you know, height says it is a chapter called Let Them, or The Lawson Play or something. Rick Rubin's been pounding on this. It talks about it in his... We looked at Gene Twangy's work, Generations. Is that another one?

Yeah, so Generations is really fascinating. This stinks of you. Highly recommend it. Okay, I will. And she talks about extended adolescence. Yeah. Sort of twins with some of height stuff. We've got a real interesting duality going on, which is in one world, you've got these kids that are sort of being forced to become adults more quickly than ever before.

We expect you to know what you potentially, this set of railroad tracks for the rest of your life, the next 30 years of your career, and you're only 17, and you've got to know and apply. And then at the same time, kids are moving out of the house later. They're getting their driver's licenses later. They're getting employment later. They're getting into relationships at lower rates. less alcohol, less casual stuff. All of the things that we would have typically associated with being an adult

are not present as we're trying to force structural adulthood onto them. That's socially very immature, professionally expedited. And he ties them together? Gene Twangy, yeah, for sure.

I think that... Oh, actually, no, no, no, no. Great point. And I don't know. And I don't think so. Now, there might be some rebellion going on. Like, everything just feels like I need to get my act together. How can I do these other things that just so much of my cognitive real estate is taken up?

I could see that. Maybe that would be a compensatory. Yeah. Like I mentioned, I think when about 10 years after Duckworth wrote grit, she said that she wished, she had positioned it as 50-50 passion and perseverance, and if she could do it again, she'd put more on the passion because she thinks we taught

a whole generation of the higher performer children how to grind. Like we taught them to persevere, which is... Well, and so I get that. Grit was a massive book. I don't think that she should lay at the feet of her pen the issues of this stuff.

But I think one of the reasons why, from a personal development standpoint, it's a bit more seductive to overindex on the perseverance than the passion is the passion feels more difficult to engineer. Fair enough. So how do I get the thing, the line, the stuff, right? It feels a bit more egalitarian.

Yes. To say, no matter what it is you're doing, if you hold hard enough, you can get. I do think it is the hardest question. What is? Finding it. Like, finding it and knowing it, you know. Knowing it's a little easier, but finding it.

There are a lot of 17-year-olds who appropriately, if you ask them, where's your passion, what do you want to do? They appropriately say, I don't know. Because it's the truth. They don't know. But I think that's okay. It's just we shouldn't force the question upon. You've got this line,

life is a use it or lose it proposition. Yeah. What's that mean? Well, I mean, it's tied to the boldness regret, right? Like you're going to get to the end and then it's done. And only if you think in the way that Beazel, did with his regret minimization framework, are you going to hold yourself accountable for that line?

You know, the recognition that life moves much faster than any of us realize, and then it's done. And you can get locked in even sooner. If you spend up to your limits, you can freeze yourself in a job that you can't leave. And you can do it with personal commitments as well. My second career was, you know, going to Wall Street. And I can't tell you the number of people I worked in with Wall Street that had, for their age, ridiculously high salaries.

But they had to place in the Hamptons, the summer lease. Like, they tried to get into the membership club. Like, they spent right up to the limit. And now you can't switch. You know, you can't switch. Yeah, you're locked in at this very high burn rate, which means you need to keep pouring fuel in the top of it. Yes, yes. I have like for young adults that are lucky enough to have a job with a decent salary,

I would heavily encourage them not to spend against it just so they can have the flexibility to do other things, move cities, change jobs, all of which may be the right path for them. We'll get back to talking in just one second, but first, if you have been feeling a bit sluggish, your testosterone levels might be the problem. They play a huge role in your energy, your focus, and your performance. But most people have no idea where there's are or what to do if something's off, which is why I partnered with function because I wanted a smarter and more comprehensive way to actually understand what's happening inside of my body.

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And right now, you can get $100 off, bringing it down to $399. Get the exact same blood panels that I get and save that $100 by going to the link in the description below or heading to functionhealth.com slash modern wisdom. That's functionhealth.com slash modern wisdom. Yeah, and it's weird, isn't it? Because flexibility is actually a really difficult thing to show off. it doesn't it doesn't

it's and even flexibility is only show offable in so much as you can take a photo of you on a plane

or you at a which again is not quite the flexibility that we're talking about here so I've always thought about this

the difference between hidden and observable metrics yeah will often trade a hidden metric for an observable one sure

you know trade the quality of our sleep for a slightly bigger paper packet will trade the hours of peace that we have on a Saturday for position improvement. We'll trade, I mean, you know, some people will trade a caring, supportive wife for a very difficult, younger, hot one.

You know, the trades are everywhere. Yes. I think that's a good framing. So is many people, especially people who maybe aren't so fired up with their jobs and their careers might think I can get my fulfillment elsewhere. Why should I care about my career is just it's just the thing that I do from nine to five or whatever, eight to four every day. Why should I try and optimize that? Is being fulfilled at work a luxury? I guess what I would say is I have a immense amount of respect for someone who adopts that mindset, the one you described,

especially if they're really thriving in something that may not, they may not perceive to be an occupation. That could be a religious community. It could be volunteer work that they do. I would highlight to them there might be a career in that, you know, like if they wanted to be around it all the time. But my main goal isn't to tell those people they aren't being successful. Like if they're happy,

and passionate about that lifestyle, like, that's great. I'm not casting any shadow on that whatsoever. If you are the type of person that is either unhappy with your work, like so much so that it's impacting your quality life, or even better, if you're someone that has this inkling, this little notion in their brain, but maybe doesn't have the confidence or the permission, they don't feel like they have their permission to go do it.

That's who I want to read my book. Like, that's who I really really want to read my book. There's this, there's a great story. There's a couple of these, actually, but I'll choose the Steve Harvey one. There's a, I don't know if you've seen this, but you know who Steve Harvey is, the comedian who does the family feud now? Yep. He tells this story, I think he told her on Oprah, that when he was seven, the teacher asked them to,

as an exercise to write down a sheet of paper what they wanted to be when they grew up. And he claims he got called last, and the teacher said, the others she read, but for his, the teacher made him come to the front of the room and read it out loud. And apparently he had a stuttering problem. But he said, I want to be on TV. And she thought he was like not taking the exercise seriously. And she condemned him for writing that. So much so. that she called her, his mother, and he got in trouble when he got home. So he got sent to his room. He's worried that his dad's going to come in there and read him the riot act. And his dad comes in and sits next to him. Here's the whole story. And he says,

here's what we're going to do. Let's take that piece of paper and put it right here in your bedstand. And I want you to read it every single day. And you hear a story like that, you know, And I don't think there's a lot of people, I think that that's a very hard thing to do. I think that for parents, and I'm a parent of three and I live through this phase that we're talking about, your intuition as a parent, like some in your DNA somewhere is to look after the economic welfare of this child. You want them to live a good life. And it's very hard not to associate that mostly with money. And so this thing that's,

Steve Harvey's dad did for him, I think, is kind of a really, like, a very unique thing. I think it's very hard to do. And I hear a story that McConaughey has a very similar story about when he switched from law school to film school, his dad told him, well, don't half ass it. And he said that was the last thing. He thought his dad was going to yell at him. And his dad kind of gave him, like, this push. And that's what I want the book to do.

Like, if someone has that inkling that they want to go do something that the world may not think they're capable of or think they should do. I'd love to unlock this latent human potential. You know what it comes back to? It's quantifiable, observable and observable and hidden metrics again. The observable metric of financially free, this is how much they earn, this is the track that they would be on, hidden metric, how passionate are they? Are they happy when they're 35?

Yeah. So I guess one of the situations that so many people, people must be in is someone, one version of them successfully pivots and another version of them stays stuck for life. Yeah. Why does some people successfully pivot and others end up getting stuck? Well, I mean, you could come up with a number of things. One of them is financial, which we've talked about.

You could be overspending. There's a different case where you're just, you're stuck financially. Like you need your living hand to mouth. I have a profile in the book of Jen Atkin, who I don't know if you know she is probably the most successful hairstylist of all time. Like, when not only achieved touched the top rail of that, but then launched beauty products sold that company. But she moved to L.A. with $300 in her pocket. And that's not to say anyone can do that, but like there are stories of people with near nothing starting on the very bottom rung and finding their way to be successful. this classic meme of starting in the mailroom in Hollywood and David Geffen and

Barry Diller and all these people started in the mailroom, you know. It's about as low rung as you have in that business. So I think it's possible, but you may feel stuck financially. You may feel that you can't get there. And then the other one, you know, it could be like this perception, McConaughey had this perception that his father wanted him to be a lawyer. It's probably just, you know, it could be a lawyer. It's probably just, you know, it could be, that Matthew had told him he was going to be a lawyer and he was supporting that. But that weight can be there too. Like you may feel, I think there are certain cultures where like being a doctor is considered really in Russia, like being an academic.

So you may feel pressure from your family as this is the thing people in my family do. And I've seen that. And I've met people who have that weight upon them. Those are all kind of things that could restrict this movement. What about the fear? There has to be a huge chunk of people that just, what if this doesn't work? It's sort of ambient, ephemeral, this fugue, fog thing that's come down on that. If you allow me to give you a little history of how, or why, I would say, I spent six years turning the original presentation into a book.

and I had this thing I really wanted to achieve, which was to embed as much stories and narrative into it as possible. And I was listening, I know you've had Morgan, how's the goat. He's the absolute goat. And he was on, he was on a podcast called Why We Write,

talking about David Pearl. The power of narrative. And so the book is divided, it's structured unlike most books. It's divided into two parts, but they interleave. And so every other chapter is a Atlantic-sized article about someone that started on the bottom rung with intention and made it to the top. And the reason I wanted to include those is precisely for the reason Morgan talks about, which is I think these things stick in your brain more. Like a lot of the books in the category that have done extremely well in career read like a textbook.

do A, they do B, then do C. But they don't have this kind of spirituality to them that I think can infect the brain a little bit more. Does that make sense? It's 100% correct. I mean, Ben Shapiro's famous line of facts don't care about your feelings is as backward as it could be, that feelings don't give a single fuck about the fact.

Yeah, so we have eight, nine or ten, I should know the exact number, but I can't recall right now, of these profiles. And I alternated them with the principles. and it's, I wasn't thought about it like candy and vegetables, you know, or something. But you get, you get some of both. It brings the ideas to life. Yes.

And I think the reason I told that long story was an answer to your question about fear. I think seeing this many stories, and they're all, by the way, I chose every one of them from a field that your parents would probably tell you not to go into. I intentionally skipped, you know, investment bankers. and doctors. Yeah, all the stuff that everyone knows is. Nice linear progression. Yes, I have none of those in there for this reason, because I wanted to help people get past the fear

by giving them the motivation and the method to do it. I hope it works. Me too. Well, you're certainly right about changing people's opinions with, beating them over the head with frameworks and justifications. It's straight up. does not stick. Pithy mantras and quotes and stuff can do,

they're a nice compression algorithm. Yeah. I think for bigger things. But really what you're optimizing for, and I'd be interested to know if you agree with me on this, I think you're optimizing for memorability. Yes. And I'm just,

I just don't think that, regardless of how well-written, whimsical, insightful something is, it doesn't, the human brain, the keyhole, isn't the same it doesn't retain things quite as easily the aphorism and stuff is nice

that's kind of like the tune from a song it's the lead melody from a song that you can hold on to but if you give somebody a story how are you going to forget that? Years ago and I don't know when it started actually it's funny I just said I don't know where it started and then something popped in my brain I fell in love with these

long form nonfiction articles there's a website called Long Reeds that it has best of And it's a lot of Atlantic stuff, that kind of thing. The thing that popped in my head was there was a New York magazine article, Shug Knight and Snoop and I think Biggie were on the cover of New York Times Magazine when I was, it was in 93 or 94, and it was 20 pages. That may have been the first one that got me into this.

But that led me to a book called The New Journalism, and there's another one called The New New Journalism, about these writers that kind of left the being beat writers on newspapers and started doing this longer form journalism and how it brought stories to life. I think Truman Capote's highlighted in that. Tom Wolfe put together the first one. And then the second one has Krakauer and Lewis and like all the modern. Well, now we've seen this pivot into substack, right? That people that were previously hard, core journalists have made their entire careers on substack. And then if you're somebody like Barry Weiss, you've done this sort of double U-turned thing and loop back on yourself enough. And you end up in charge of CBS. You're Matt Taibi and you end up in charge of the Twitter files

or whatever. I'm a huge Barry fan. So talk to me about the risk of starting over in your 30s or 40s. You know, the idea of not just what am I going to do, but I, you know, I should have had my life together by now. Really? You're telling me I'm going to start a guy. gain at 37. I'm going to be at the bottom of the pile and I've got all this sunk cost fallacy from before. What are people going to think of me? What's the real risk of starting again in 30s and 40? Well, I mean, one thing I would encourage you to do, there was a, there was this book I read when I was really, and I think back in business school called Shark Proof by Harvey McKay. He wrote, he's known

for his sales book, but he wrote a book about careers. And he said to keep your dream job. This was an older book, so he said, keep it in a manila folder and a file, but you could create in a Google Doc or something, that we're just keeping notes. Like, well, if I do it one day, you know, and everything you learn, people you might talk to, I think you just pile more and more stuff in there, and it'll start to feel more real. Like you can begin the process before you make the leap, right? And then the second thing, I'm going to say three things. The second thing I would say is if you have some curiosity that's occupied,

pying your downtime, that's a really interesting tell. You know, when I was an engineer, I got a computer engineering degree, and I was working at compact computers in Houston that was a big hot company back in the day. And I was going home at night, and I had started, I'd learned about stocks, and I was trading stocks. You know, I'd read one up on Wall Street. I had this, I forget what it was called, this book, you just get this book with all these one pagers on every stock.

Like, I was, that's what I was doing in my spare time. So if you're doing something like that in your spare time, like, it's calling you, you know. And then the third thing, there's a chapter in the book actually titled, Never Too Late. And we list about 20 people that did post-40 pivots, and we go deep on four of them. My favorite being local Austinite Bert Beverage, um, Bert's nickname is Tito, so that'll, that'll tell you who he is. but seismology degree undergrad, worked in oil and gas for several years, ended up down in South America where he got frightened by a few experiences.

So he hung that up out of fear and the boom-bust cycle, became a mortgage broker, didn't really love it, you know, and not sure he equated his identity to being a mortgage broker. And one night, this is such a, like, it's a... It's part of why I love, like, self-help books and ideas so much. He's watching a PBS special that says, take out a sheet of paper, draw a line down it, put this stuff you love to do on the left side and the stuff you're good at on the right and see if you can find a through line. And he's looking at this sheet of paper and realizes he wants to start a spirit company. He's got, like, chemistry on the right. It's like hanging out at bars on the left.

play and and um he didn't know jack's shit about launching a spirit company and it turns out texas is probably the worst place you'd ever at the time there was no one that had a license for a spirit company in texan um but of course chitos is now the most best-selling spirit in north america he uh owns 100 percent of it himself no way the whole thing's bootstrapped yes credit card. Yeah, 19 credit card. But it's such a great story. Like, it's just such a great story.

And now, you know, he's at the phase in his life where he's giving back and launching foundations. And this is my point. Like, I had a young person at John Hopkins raised their hand to say, but I don't want to chase my passion. I want to be purpose driven. And I thought to myself, you know, every profile in the book, these people are touching more lives than they could have ever imagined.

I don't want to chase my passion. I want to be purpose-driven. I think it's part of a new movement to just like, I feel good about yourself. Like, I'm a, my main goal in life is to help other people. Serve. Yeah. Okay, that's interesting.

Well, it's like, no, it's noble on the surface. And there's certainly some things, you know, in the same way, this person has high burn rate, family to support. You don't have the luxury, in quite the same way. This person, there are some jobs that just suck. There are some jobs. You're serving your country.

I'm sure lots of people love street cleaning, but I would imagine that some people do it more out of a sense of service than they do out of a sense of passion. My only point was these people that are able to climb from the bottom rung to the top and do it in the right way end up touching hundreds and hundreds of lives. They're serving in a much more. seamless way that's leveraged as well.

Yeah. Yeah, yeah, yeah. I mean, one of my favorite on that front is many years ago, because I was involved with Open Table, I met Danny Meyer, and who's the famous restaurateur in New York that also built Shake Shack. He has a great book setting the table if people haven't read it. But if you talk to people in the restaurant industry and they worked even for a year at a Danny Meyer restaurant, it's like meaningful to them. Like it's on their resume. They talk about it all the time.

Like there's almost this church of Danny Meyer like for everyone that rolled through it. That's got to be, let's got to just feel amazing. What is it about his demeanor or culture or ethos? The book talks about this kind of understated sensibility to his book, to hospitality.

Like just trying to read the room on each and every customer and really understand, you know, what they're trying to optimize and to help them do that as much as possible. But his journey is about more than that. That's what his book's about. His journey is about being hyper-curious and an excessive learner. Like every single step along the way, including today, he's still doing it. You know, last time I talked to him, he just got back from Europe.

he'd taken all his chefs on a tour of Europe together. Jodding notes, taking learning, like just constant learning. That's so cool. Which I think is, is, it's also, that's the second principle in my book is continuous learning, but it ties in with the first one. The best test as to whether you found your passion is, does the learning feel like free? Like, would you do it instead of watching a TV show? Like, is it something you enjoy so much?

the continuous learning is just you enjoying life, you know. And if you find that, you found it. You found your passion. A quick aside, I've been using eight sleep for years and I genuinely can't imagine life without it. Having a mattress that actively cools and heats, each side of the bed is a total game changer. And the newest model, the Pod 5 takes things to the next level. It now includes a temperature-regulating duvet that works with the smart mattress cover to deliver a full-body climate control, maintaining your ideal temperature from every angle all night long.

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by going to the link in the description below. I heading to 8Sleep.com slash modern wisdom and using the code modern wisdom at checkout. That's E-I-G-H-T-Sleep.com slash modern wisdom at checkout. Joe Hudson's got this line, enjoyment is efficiency. He says, I think it's really, really true. Yeah, that people have this relationship between discipline, motivation, and obsession. Discipline's always there, but there's a lot of friction. Motivation, the friction gets removed a little bit, but it's sort of harder to grab a hold of. You don't really know where it comes from.

Maybe it's a rock playlist or maybe the right amount of caffeine or something. And obsession is friction inverted, as opposed to you having to push through resistance. The resistance pulls you toward it. That's exactly right. And the problem, I think, or the reason that obsession is difficult is that, obviously, if it's pointed in a non-positive direction, that's how you become obsessed with politics or porn or your toxic X or something. Yeah. But if it's pointed in the right direction, what from the outside looks like a superhuman amount of discipline, from the inside feels almost like you haven't chosen it. You know, I'm not choosing to do this thing.

I mentioned before we got started. There's not been a single house I've lived in for a decade that I've not turned one of the bedrooms, including most of the ones that I slept in, into a podcast studio, for a decade. My house back in the UK has got a podcast studio on it. The one that I live in right now is still podcasts eight years in, a thousand episodes. Every single house has had, every Airbnb that I've stayed in. I get there and I'm researching hotels to see if the depth of the table can withstand my MacBook, the stand, and the fucking tripod.

because that's what I want to do. That's what I want to do. I want to have these conversations. So, okay, my entire life gets warped around it. I'm sure you'd be familiar with the single ordinating principle. I think Bezos has got one and I think Musk's got one. And Bezos's was always, does this make the customer experience better? Yeah.

So everything, every single decision in Amazon was threaded through this sort of single eye needle. And Musk says, does this get us closer to Mars? does this get us clear? And by the way, both of those people did something that is super extraordinary, which is they took an innovative company, grew it to hundreds of thousands of employees,

and kept it innovative. It's two of the only examples I know. They didn't get laden down with dis-economies of communication, lumbering, fucking behemoth. Bureaucracy that always lands in big companies. And it must be some heuristic, like the one you described that allows them.

In fact, I was just listening to Elon on cheeky pine, I think. This is Dwarkesh. Yeah, this came up. This came up. Like, like every leader wants to know how he does it. That's why I think Collison was asking him, like, how do you lead? He goes, well, I'm down deep. He can't be deep.

There's 200,000 employees. And Elon jokes, yeah, there's 200,000 employees. Like, you have to have some heuristic, simple. horrifying heuristic that, uh, that can spread through their brain. Or else just spinning too many plates. Yeah, exactly. Yeah. Yeah. It's pretty impressive. It's super impressive. Mm-hmm. Okay. So career pivot fear. Yes. Someone is in the career. I'm not super fired up. I used to be and it just feels like it's time for me to grow now. What are the indicators that it's time to move and what are the things that they should keep in mind to maximize their bravery, give them

a little exogenous amount of morale? So on the, do you know, I mean, I love this test of, do you see yourself doing this 30 years from now? Because if the answer to that is no, you should get busy. What's the line from Shawshank, like get busy living or get busy dying? Like, if you know that's true, like, well, now is when you're. should start. I'm not saying, like, quit tomorrow, but like start building the plan. Like, and then there's all kind of things you can do. In designing your life, Dave Evans says, has this

exercise where he says, create three to five scenarios and battle card them of what you might do next. Like, you know, fill them out. A.I. can really help, right? Like, like, you could build a 20-pageer on each one of these career paths. What might I like? What might I not like? What are the three things people loving this career with a three things, you can steer it at all, right? You can ask people in those fields, you can go find them. So you could, you could role play being in each of these. There's a, there's a, there's a, there's a heuristic in the book that I borrowed from, from Ben Gilbert had acquired a lot of podcaster, where he had side hustles at all his jobs. So at each job he went to, he would ask the employer, if I do it on my own time, can I do this other thing also?

And there's something really great about that. One, in each of his cases, he ended up doing something pretty remarkable in the side hustle. At Microsoft, he created Microsoft Garage, which became this way for Microsoft to stay relevant with founders. And he met all these founders. Like, all this kind of extra goodies came from that. But I think it all, like, so you learn more.

You learn maybe two, you get two shots on goal instead of one. And I think the employer makes you look perfect. So it reflects positively on you. When he ended up at Madrana VC, ask him if he could start a podcast and look for that led. And I just had dinner with both of them and they were in Austin and, man, they're happy. Like, I've got to tell you, like, they are really happy people. So similar to you and your obsession. And they fell into it through that, through getting there through that way.

So I think those are some things you can do. to test and then look what are you doing in your spare time like are there any signals there those are all great ways i wouldn't quit if you don't know where you're going that doesn't make any sense yeah yeah it's such a good shout to say sort of what are you thinking about in the shower yes what are you doing in your spare time i keep on fucking watching pickleball drills i just keep on thinking about pickleball and i'm really interested in the sport and i'm interested in how it's growing and I love playing it with my friends. But even when I'm not playing it, I'm always thinking about it a lot. But let me, let me, maybe there's something going on that. Let me share this fun story I just stumbled on

because I was, I was, I'm using some hacker techniques to promote the book and that led me to talk to this gentleman. And I, when I pinged him, he said, he said, oh, you please send me the book. He goes, I saw the video a long time ago and it changed my life. And I said, well, tell me that story. and he was a real estate lawyer, and he loved football, and he loved offensive plays and offensive diagrams in football. I love this story because it fits with my thesis that the best stories are in jobs your parents would tell you to never go do. He launches a website to help people, like, manage and develop football plays.

And then he builds software, and then he starts a podcast. He has 900,000 followers. And this is what he does all day now. He talks about offensive football plays with the best and the brightest in the field. He's known throughout the industry. What a great story. Like, how awesome is that? That's brilliant.

It's so great. I think people don't realize that you can actually, there are careers in a lot of places. A lot of people want to be in Hollywood or music and they think they can't do it because they're not talented. But there's 100 support jobs for every artist that's out there. And there's tons of work to go do. You know, if you really love being around that stuff, there's tons of opportunity. Especially given that you can fail at a job that you hate. You can underperform in a industry that you don't want to be in.

So the prospect of potentially doing okay at one that you love is infinitely better. I think so. I think so. That goes back to life is a user or lessive proposition. Like, give it a go. And then the other thing to know about failing in that is humans are, like the research in psychology says humans are really good at forgiving themselves. Like, you're not, the failure's not going to, you're not going to ruminate on it forever. Especially if you tell yourself, well, I'm proud of the bravery to make the call.

No doubt. Isn't there some evidence from psychology that humans prefer, just making decisions generally, that if you make a decision, you tend to be happier. Let's say it's maybe a slightly less momentous decision between one city and another. The city that you're in now are moving. On average, people that move are happier. And I think part of that is just, well, life is, like novelty and variety are pretty fun. It's different and no doubt exciting.

And even if it's objectively a little worse, subjectively, it's all new. Yes. I like that. I liked it. I just had a similar life experience. I spent 25 years in the Bay Area living in one type of community. And when I moved to Austin, I moved downtown in a high-rise, completely different. Repet.

And it's invigorating. Like, it's awesome. New place for coffee, new place to work, take your calls, your morning walk. All that's different. That's great. I agree with that sentiment. So you quit a successful job at Compaq to start again. Yeah.

How do people know when they're plateauing versus they're just a bit bored or something? Yeah. A few people have asked me this question. Once again, I think the 30-year forward exercise gets you away from that because it's asking a different question. One thing I'm really big on is, and there's a different chapter dedicated to this, is developing peer relationships. And we can go into why I think that's such a huge unlock. But one of the benefits of having a group of peers, especially if they're outside your organization.

So these are people on the same career path you're on, or maybe a bit distant. They're at a different company or whatever. And if you have a community like that that you really trust and support one another, they can help you with that question you just ask. Like, am I failing and I'm never going to succeed because I don't have the right talent for it? Do I maybe have a shitty boss? Is their experience different? Like, it's a great group of people to ask those questions of.

It's almost like being able to run a little split test of yourself. Yes. What are the things that are different in your experience? and how much of those are fundamental to the role. Exactly. Yeah. And how much of that is transient that I could just. Absolutely.

Absolutely. Finesse my way out of. There's 10 other reasons why you should build that group, but it's good at helping with that problem that you just described. How do you deliberately upgrade your peer group without it being transactional? How can you make like-minded friends and peers without them thinking that you're constantly just wanting something? Yeah, it's a tough question because I think the number one reason people are bad at forming these peer groups is they've been taught to be a climber and they've been taught to almost been taught to be a bit sharp elbowed and to outgun the next person. Zero summy.

Yeah, and we borrow a lot of our mental frameworks from finite games that have a beginning and an end and a single winner. And careers just aren't that way. almost any industry, if it's not downhill skiing, there's lots of winners. You know, there's tons of winners. Podcasting is a great example of that. There's tons of winners in Austin. And so if you can build a peer network of like-minded people that you trust, and the great test of do you trust, would you share your best ideas with them,

like that you've learned, this new thing that you just unlocked in your job? Would you share it with them? You should actually, I believe, but a lot of people wouldn't. And so if you, once you get to that place, it's a really special place. There's a story in the book about Chris Delcante, who's the athletic director here at the University of Texas. And when he broke into sports administration, he was in the development office, he went to a conference. And it's a great place to meet peers. He went to a conference and met with a couple of other young.

men who were also at the beginning of their career, they exchanged numbers and started a text group. And over time, they added a few more people to that. Got up to like seven, seven or eight. They're all eight, all eight of them are D-1 athletic directors now. And they all started on the bottom. And if you follow them along that journey, they're learning elevated each time. Each year they met, each time they texted the problems. They were encountering. They were shoddering. They were sharing, they're explaining. It got to the point where they would do weekends away with their wives and invite in guests.

You know, you talk about external learning. Who's holding many conferences on their own nickel and bringing in external guests to help educate them so that they could rise and thrive together? It's just so, I just like, I get like, there's another story that's perhaps more modern for the younger crowd. Mr. Beast did this when he was 17. He found three other people they were trying to hack YouTube.

They were basically trying to figure out the game of YouTube, and they were on a Skype call for 16 hours a day together. And he says if there were a fifth person in that room, they would have made a million dollars also. Like, it was just because the stuff they were uncovering was so usable

and just deterministic, just no one else knew it. And he used a phrase, I love. He said, you know how they talk about 10,000 hours referring to the Malcolm Gladwell book? He says, we got 40,000 hours because we were sharing it all. That's not the exact math, but it's a cool reflection of the moment, you know. A quick aside, you've probably heard experts like Dr. Ronda Patrick talk about the benefits of omega-3s. They reduce, hello, omega-3s, there they are. They reduce brain function. No, they don't. They support brain function. Maybe I should take more. They support brain function, reduce inflammation.

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or heading to livemomomomomomom slash modern wisdom and using the code, Modern Wisdom, a checkout. That's L-I-E-M-O-M-T-O-U-S dot com slash modern wisdom and modern wisdom. A checkout. What do you think about mental tours, you know, peers are great that struggling with the same challenges you're sharing and sort of going on the journey together. That feels cool. It's like a teammate. But presumably there's a

good argument to be made. Well, maybe you aim for someone that's already been through the pitfalls. Yeah. How do you come to think of the role of the pitfalls? I think you do both. I think you do both. They serve very different purposes. The co-learning journey, I mean, peers give you, give you co-learning. They give you support, which I talked about. They give you reflections to, you can ask those questions. Is this the same in your job? You're vulnerable with peers. You wouldn't do that with a mentor, right?

Like, especially if you get the peer group in the right place. You tell them, I'm struggling here. Like, so I think it's just a different purpose. I think mentors are extremely important, but I think the idyllic version of a mentor's a bit broken because we encourage a lot of young people to cold call too high where the rejection rate is going to be 98%. The CFO of this company doesn't want to be friends with you. Yeah, exactly.

But it happens constantly. And so what I encourage people to do is divide mentorship into two different categories, have aspirational mentors. And just like that file folder for your dream job, create one for each of them. Like study them like a kid might study. study Star Wars characters or something. You know what I'm saying? Like really get enamored with these people that you idolize as aspirational mentors.

And one, you're going to learn a lot studying them. And by the way, the resources are amazing right now. YouTube interviews, podcasts, like AI, you can learn faster than you ever could have learned before. So study them. If you ever meet them one day, the fact that you studied them this long is going to prove super useful. And then for the mentors you actually want guidance from, like, tone it down a bit. Like, go two levels below what you thought you were supposed to do. And you're going to meet somebody who's so thrilled that you recognize that they were successful and worthy of giving advice

that your hit rate is going to go up 10x or more. Like, the probability that you're going to get them to do the work is so much better. Like, I, I noticed that when I first started the show in 2018, still not early, it felt late, but you know, now it feels early-ish. It was so flattering for people to be invited on a podcast. You know, one of the other things is such a funny trick that I still use now, so the world can have this one. I realized that flattery was one of the big drivers, I think, for bringing people on the podcast,

especially no one knows who it is. It's this random British guy asking you if you should come on. I always used to ask people, can you please put me in touch with whoever handles your podcast adverts? And it's some small researcher at fucking University of Arizona. Uh-huh. And they're like, oh, well, it's just me that handles my part. I'm seen in the echelons of those that would have an assistant or perhaps a receptionist that would handle my podcast ads. I get it. So, and that's still now.

Please pass me on whoever handles your podcast ads. And that's actually another good one, I think, just generally for any outreach to somebody. You want to be in front of the right person. And especially if you're starting to pitch up toward mentors, that right person who actually handles that thing might not be them. So, you know, reaching out, you please put me in touch with whoever handles bills, inquiries for coffee or whatever it might be to the admin inbox. Because the last thing that you want is some complex question that the person,

person who handles the inbound open email thing or the LinkedIn, you know, the LinkedIn DM requests. Is it them or is it going to be somebody else? Are looking to get put in touch with the person who handles their partnerships or the whatever it is? If it is them, they feel flattered. And if it's not them, the delegate person passes you on to the right department. And, and this isn't in the book, but if you ever meet the delegate person, pay as much attention to them as you possibly can.

Like, learn all you... Just look through them. Oh, yeah. Learn all you can about them. Like, be generous and kind and thoughtful. You know, good... It will pay off big time. Good story around that from the show.

David Goggins. You familiar with David Goggins? I'm not. Okay, so he, ex-Navy SEAL, endurance athlete, probably one of the most sought after podcast guests on the planet. In the last... Probably six years, he's done

two podcasts. One of them was mine and the other was Rogan. It brought a brand new book out. His first book sold gazillion copies. It brings a new book out. And for nine months, I'm back and forth with a person on his team and checking in, seeing how everything's going, seeing the marketing, this, this, this, this, this. And then he canceled every other podcast appearance except for Rogan. And they tried to cancel the one with me as well. And I got this message. really sorry, David's just going to have to, we're not going to be able to make it work. And I was like, I will do whatever it takes. I'll move heaven and earth. I'll come to you. I'll bring you to me. We'll change the date. We'll do whatever it is.

And they said, a couple of days later, I got another reply. Okay, we're in. We'll be able to make it work. And when I turned up, David, he's sort of stern, stern, hard guy. Comes up. Very nice to meet you. The first thing he says after that is, I just want to you to know, the only reason that I'm here is because of her and pointed to the person that I'd been emailing. Yep. Precisely. So in your framework, loving the grind is sort of a non-negotiable. Yeah. Can someone sort of learn to love grinding, or is that innate? I don't think so. But, you know, when you were talking about your love of podcasting,

You know, the word that popped into my brain, and there's a book by this title was flow. And I just find people that are truly tilting against their passion, they never even think about it as work. Like, and at times, the experience does go into this flow thing. Like where when you're done, you don't even remember doing it. Like, you're just that much enamored with the whole thing. And because, I've felt that and I've seen it, I just, I really don't know how you could do that. I suspect some human is just wired in a certain way where they might be able to do it, but I don't know that most humans could. Like, and I don't know, I do think we get a lot of young people to do it for an extended period of time. And, and I meet the meat grinder thing. I meet, I just yesterday met with five of the top.

I helped start this robotics honors program at Texas, and I met with five of them. And, like, you know, they're giving you their background, Eagle Scout, and it's 1580 SAT, and all. Like, clearly, this human's been programmed to go take the hill, like, on every single thing they do. But I don't think that's the path to greatness. Like, you know what I'm saying?

I just don't think, I don't think just being good at the grind is what it takes. to be truly exceptional. Brute forcing creativity, sort of white-knuckling your way through miserable successes, it lasts for a good while and might be sort of the activation energy you need to overcome some discomfort at the start.

But I would agree, I think. Maybe if you're just so damn competitive, like winning all the time, is your passion? It's a meta-pashion. That's possible. Yeah, that's interesting. And that's certainly some people, right, they just want to win. Yes.

I think Michael Jordan would be a good example of this. If you heard Novak Djokovic's interview where he's asked, why are you so good at tennis? And he says, I just like hitting the ball. I love that. Yeah. Whereas, you know, Jordan invented rivalries. He invented slights against himself. Was it 92 or 93?

Very driven human being. He wins some, I think it's his induction into the Hall of Fame. And during that speech, this is the moment that you've worked, supposedly your entire career for. He takes a shot at somebody, right? He spends the entire speech, just revealing all of the slights that from his past and this person and this, but they didn't believe I'm getting, da, da, da, da, da.

You're even at the moment where you've broken through escape velocity, you're out in space. I don't love that that much, you know. It's not the energy that I have. Yeah. So there's a, there's a, there's a, there's a counter example to that. There's this thing you can find on YouTube where Shaq was on, uh, the, that famous show that he does with, with Kenny and Charles and Ernie.

And, um, inside the NBA, I think it's called, uh, the, uh, he's at the All-Star thing. And there's all these legends there. And he just kind of goes off on his own. talking and he talks for like five minutes and they don't interrupt him and he's telling his story of how he made it and all the people that influenced him along the way and how he views all these legends as idols and he just goes on he's just thought thankful like gracious for four or five minutes and ernie's crying by the time he's done and i love watching it i've watched it probably 10 times i just love the notion that you carry that much thankfulness for the others that helped you get where you are.

And I think in conveying that, it maybe in, it makes him look like remarkable, you know, it really does, like that he, that his brains wired that way. I felt very proud of him. I have no reason to be proud of him, and he probably couldn't care less than I am proud of him. But it was, I like that. I like that version better. It feels much more pro-social. Yes. I suppose the problem is ultimately what matters is performance,

especially in an industry like that. You know, if Michael Jordan was some middling or pretty poor quality basketball player, calling out all of these people and inventing random rivalries to try. try and motivate himself to go, people would look and say, you're just bitter. And the same thing with Shaq. If Shaq, who had a version of him that hadn't achieved all of that, was, you know, proselytizing about these wonderful people and how grateful he would be called a suckup. Yeah.

And this is, that's fair. The medium is the message, but the medal is the message very much for this stuff. Well, and look, that is more of a finite game, right? Like, that is, and I did you, downhill skiing, but there are, like, those kind of competitive sports, you may need to be sharp elbow to climb to the top. If you're an author, the same thing is not true. That's right. That's my main point. And most of the careers, most of us chase, that's not a reality. But I also have a principle always give back, which is why I feel warmly about the shack thing, which is I think that the minute you move from the first rung to the second rung of the ladder, If you take the time to appreciate the people that helped you with that movement,

you will develop a process that you will feel really good about at the end of your life. And your network of supporters will grow faster. You'll have more friends in your corner. You're seen as the pro-social hub as opposed to the person that stepped on a bunch as they come up. Yeah, you'll be able to weather the bad times and enjoy the good times more. Yes. But so you talk about honing your craft, kind of interested in what that looks like in knowledge work when there's no clear scoreboard. Well, here's what I would say is, and I think this relates to this college grind.

I think some of these kids are so burned out by the time they get to the end of their senior year in college that they can't wait to not study anymore. Like they view it as, okay, 12 years plus 4, 16, I'm done. And they're looking for a break from studying. And the best in their field, like Danny Meyer, are studying all the time. And so that's a weird contrast. And there are fields where continuous learning is somewhat required. The medical profession is one where that happens. And obviously there are fields like ballet where if someone says they work 16 hours a week or a day, we all applaud it, which is weird because if you said that about an engineering career, they'd say you're a bad human, you know, but whatever.

So this notion of learning constantly in your spare time, I think it's just the best test of whether you're truly obsessed with what you're doing. Do you remember when Elon took over X and he did that announcement post and he said, we are looking for people who want to work on the hardest problems possible as long as they can at an unrelenting pace to try and change the world? And there was a lot of quote tweets of this saying, we're throwing it back to a version of work-life balance that is completely primitive. This is abuse. This is horrendous and all the rest of it.

And don't get me wrong. There are certainly some bosses and some industries that will drive their employees so hard that it's irresponsible. But if you're stating it up front, what all of those people that quote tweeted it and complained about Elon's horrendous working conditions failed to understand is there are people out there to whom that sounds like a dream. Yes. They want to work 18 hours a day, fueled exclusively on high. quality stimulants and chick fillet. Especially if they get to hang around with the smartest

people. And they want to be pushing each other and they want they want to send it. They want to send a living shit out of it. You know who's doing that right now, which is super interesting? The young AI founders. They've embraced this meme from China 996. It actually was developed in China,

which means 9 a.m. to 9 p.m. 6 days a week. That's what it stands for. But they used the phrase. And Silicon Valley got lazy in COVID. So you have the situation where the broader culture had moved from being formerly a bit workaholic to being lazy. And despite, you know, they literally aren't coming into the office. You can go in downtown San Francisco and look through buildings, you know, because there's so much cubicle space with no one there. And these young kids in this AI world eating the lunch are the ones you're talking.

about that want that experience. It was some examples of those. I think almost all of, I'm serious, almost all of the AI companies in San Francisco have this mindset, especially if they have a young founder, like a 20, 22, which is, but there, but it, it, it, it, I'm agreeing with you.

Like this notion that, okay, you don't like it because you don't think there's work life balance. Do you think it should be illegal for them to do it? Like, I don't. They need to choose their own life. It's kind of the argument for drug legalization, but it's workload legalization. Exactly. If you're doing it, it doesn't hurt anybody else.

You do to your workload as you wish. But I would say this, if you're, you do need to recognize that you might one day be competing with someone that has that high. Absolutely. And that's where I go back to, like, do what you love. Because if you're sitting next to that person, And you're white knuckling it and they're loving every moment. Yeah, you're probably going to lose because they're at home learning in those extra hours, stuff you're not. Like, there's no way to keep up.

Yeah, well, it is, even if every small, if every iteration of you doing a thing degrades your willpower, drive, whatever, even by the tiniest, tiniest, tiniest, amount, it is just a single direction trajectory from you to crash land into burnout. Well, and the gap is going to grow. And I'll tell you one other thing which I stumbled upon, which I think is an interesting juxtaposition, if you're a grinder, if you followed the path you were told to follow, you went to the school you were told to go to, you got in a program you were told to go to, you became certified as an accountant or an engineer,

whatever this thing is you did, but you don't love it. You're in that place you were talking about. I suspect for those people, AI, scares the living shit out of them. Like, they view AI as grind versus grind. It's going to crush me. It's going to, I'm going to lose my job.

Look at this world that's unfair. Now, if you contrast that with someone who is a proactive, independent climber, who's trying to build their craft, their world, their continuous learner, for that person,

AI is a jetpack. Like, they can now do more things faster that they wanted to do and they can achieve more than they were able to before. They get to run extra fast. So two people, maybe in a same station in life, AI looks like the opposite to them. A threat or a nitrous turbo boost. Yes. A quick aside, if you've noticed your energy isn't quite what it used to be, even though you eat well and stay active, there might be a reason for that. As we age, our mitochondria, which is the parts of our cells that produce energy, become weaker and make less energy, which is why I am such a huge fan of timeline.

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off and that 30-day money-back guarantee by going to the link in the description. below are heading to timeline.com slash modern wisdom. That's timeline.com slash modern wisdom. Can I read you an essay? Did I wrote? Sure. Cool. So, guidance doesn't sculpt us into something new. It exaggerates who we were already. The pattern is almost cruel. The ones who least need the medicine are the ones most likely to overdose on it, while the ones who need it desperately are immune. Advice doesn't land evenly. It finds the path of least resistance and tends to be absorbed by people who all lean in its direction. So I first started thinking about this when considering the post me-me-to instruction of don't be pushy with women. And I realized that it made conscientious,

anxious guys even more timid, while the dudes that were blowing through boundaries just didn't take heed, exactly. Or another example of the prescription to just work harder. That gets devoured by the insecure overachiever, who's already bleeding effort into every crack of their day, while the genuinely lazy person just coasts past it unchanged. They're called to take more responsibility. It encourages the one who always thinks that it's their fault to carry even more of the load, while the ones who constantly point the finger elsewhere never change. There's a bunch of reasons.

People filter it through their existing traits. It amplifies predisposition instead of correcting overbalance. We all want to be good, so we sort of over-index guidance that flatters our self-image. But I think the most influential one is that the pieces of advice that most match our inner fears are the ones that we believe the most. So an anxious man doesn't just hear don't be pushy. He feels that it confirms the fear any move he makes is already too much. The sensitive man doesn't just hear open up more. He feels it confirms the worry that he's emotionally inadequate, even when he's already oversharing. And for what we're talking about, the insecure overachiever

doesn't just hear work harder. They feel it confirms the suspicion that they're never enough regardless of how hard they try. And this to me, the disproportionate way that advice, you call them advice hyper responders, right? The same piece of advice goes in very different directions to two different people. I do still think that developing a grind capacity is important. But if you don't have the passion part,

if you don't actually care about it, you can drive really, really fast in a direction that you don't want to go. and that's the problem that you will look back on a career where you white-knuckled a shit ton of lauded but largely unfulfilling wins yeah and and look i'm i'm somebody that i don't think you feel this if you switch jobs at three years but when you when you reach a true retirement and i'll be 60 next year and when I decided that, okay, I loved every minute of being a venture capitalist, but it's time for me to pass it on to the next generation and move out of the way, it's reflective. Like, oh, shit, I'm, I'm there. And I think it's hard when you're 25, I think when you're, one of the benefits of being 18 is you don't see the end of times at all.

And that gives you all kind of superpowers, like to play. There's some point at which you realize there's an end to all of this. And for this particular thing about your career, I think the sooner you can feel that to better. Just because if you do want a different at bat, like. You want to front load that fear a little bit? Yeah, if you can. I don't know if everybody can. Well, I certainly know that the regret minimization thing, there's a variety of different exercises that have done.

George, my housemate, used to think he did this. He did this six years ago. I remember him telling me about this six years ago, and I thought it was insane. I kind of still think it's insane now, but I know he still does it. I think it's one morning a month. He's got a reminder on his phone. He wakes up, he lies in bed, and he imagines what it would be like to have no arms or leg. He viscerally thinks about what it would be like

to have no arms or legs for 30 minutes. To be grateful? Is that? And then to be reborn into this body. Yes. With the arms and the legs. So I've been really pushing hard over the last 18 months on emotional work. Trying to get below the neck, as I've said.

And I think a big person. Part of it is this, how many smart people who know all of the insight, they could do an expected value calculation about the likelihood of the success and what is the objective quantifiable utility of enjoyment versus, but then you've got hidden and observable problem coming through again. But ultimately, what that strategy from George is trying to do, what your regret minimization thing is trying to do, is not really frontload more information. It's trying to overload emotion. It's like, oh my God, there's a great fucking workbook from Tony Robbins unleashed the giant within, but it's this weird 1994 audible workbook and it's only an hour

and a half long. I can't even find it. Listen, I've got it in my audible. George's got it in his, a couple of our friends that we've sent it to. I can't even find it publicly. I don't know what fucking, it's your hacker friends that have got us under the back. And in it, he's got this thing where he says, imagine what it's cost you in the past. imagine what it's costing you now, imagine what it will cost you in the future. You want you to overload the pain. It's like feel as much of it as possible. All of the rumination and the grief and the wistfulness and everything that from what's happened.

And right now, how is it affecting you? How is it limiting your time? How is it stopping your happiness? And the future, what is it going to do to you? What's life going to be like if nothing changes for a decade, for two decades, three decades? Yeah, yeah, yeah, yeah. What are you going to be like? What are your relationships going to be like?

The quality of your mind, your health, everything. And then imagine what life could be like if you changed. And he's trying to get you to oscillate between this pain pleasure principle. And I've had to make some, I moved from the UK. I was 32 years, 33, nearly 33 years old. With a successful career in the UK, running nightclubs, one of the biggest events companies in the north of England. It's something I dedicated 15 years of my life to.

COVID had just had. happened and nightclubs were just reopening. The clubs reopened and I didn't want to go back. I just wanted to do the podcast. And that was the exercise that you went through. And I presume zero regrets about to move at this point. The best single decision that I ever made in my entire life. But even with that, in going back,

I don't have the borrowed authority of my fears from back then. So this is a great idea from Morgan. I'll send you this once we're done. this wonderful blog post he talks about nostalgia and about how we we sort of were unable to see the pains from the past especially when we've moved on we don't see our fears from the past particularly well so him and his wife are talking about when they used to live in New York and they were in their 20s before they had kids and he's saying to his wife wasn't it so wonderful we used to wake up on a Saturday we could lie in bed we'd get a coffee we could just walk around we had no response but we were

just kids it was so beautiful his wife goes what are you talking about? You were miserable. You had no idea if your career was going to work. We constantly had money problems. We didn't know if we were going to make it. You were worried about where your future was going. And Morgan realized that in retrospect,

all of his fears that were a waste of time, he knows were a waste of time. He didn't need to worry. So what he sees is how he should have felt, knowing how well life was going to go. Yeah. So it's the same reason that no one ever believes we're living through a golden era. Golden era's only exist in my memory.

And all of that together, you know, I can't see, I know that I had the fear. I've got the fucking journal. I've got the journals on my Apple notes still of, what if I do this thing? And it goes wrong and everyone's going to laugh at me and I'm going to have to come back and live in my mom and dad's spare room. And I'm going to have a gluten intolerance and a club foot and be under a bridge. And it's all going to have not gone well. be that would have been the case, but that is the worst possible scenario. And there were there's gradations between the best one and the worst one. But yeah, I'm really proud of making

that decision. But even that, the best single decision I ever made in my life, I still had to apply a fucking galactic volume of pain and the same amount of pleasure in a desperate attempt to galvanize me to do it. So, yeah, even decisions which in retrospect feel very obvious, I think at the time require the inhuman amounts of motivation to get the activation energy to get you moving. I like the battle card notion. I mean, it's similar to similar designing your life stuff, but like allowing yourself to fully imagine the other reality, you know, and without the comparison, like while you're,

while you're doing it, like really imagine every element of it and on its own and then maybe go back and do the one you have and then battle card them. I love that idea. I think one of the reasons I was a useful venture capitalist and one of the reasons I, this regret minimization thing work for me is I think I'm very good at bringing forward the future in my brain, like extrapolating back, if you will, almost like a. a life in PV kind of thing. Yeah, yeah, yeah, yeah. Just able to do that. It's like reverse time travel. Yes, and it makes those exercises work better, you know,

the fact that I somehow can do that in my brain. Speaking of that, you're a very successful investor. What were you looking for in the founders that you invested in? What were the traits? What was the global decision framework? And a lot of, VCs say the same things over and over, so I'm a little hesitant, but I'll do it anyway. The one that took me the longest to fully recognize is how important product instincts are.

So that's critical. Like new, most of these companies are riding some new wave, like this AI wave, and the product surfaces of the new thing aren't as well understood as the ones of the old thing. Think about the mobile movement. So you're predicting. And you need instinct to get that right. Like you just need instinct about humans and how humans like to interface with things and a whole bunch of stuff. So products are a big one. Salesmanship is a huge one that people probably don't think about enough.

But if you're a founder, you're selling to new investors, you're selling to employees. You own the company culture and the perception of the company. you're striking deals, you're selling to customers. You're just out selling all. You're the number one sales. You're the chief salesperson for your company, and if you're no good at it, you will struggle. So that's another one.

Determinism, you know, and it kind of goes back to everything we're talking about with chasing your dreams. But, you know, Josh Wolf at Lux Capital says, chips on shoulders put chips in pockets. And like someone, that maybe failed a couple times. Got a point to prove. Oh man, you want to feel that.

Like you want to feel that they're never going to give up. A bit. Yes. Like, not a bit. Like, you want top one percentile. Yeah, yeah, yeah. You want to be afraid of a little bit about how determined they are, you know. What was that line?

Is this person going to do this no matter what? Was that Bezos? Bezos, I asked Bezos, you. found that. I asked Bezos once how he could be such a successful angel investor because he's running the largest employment account company in the world. There's other shit to do. Yeah, exactly. He has less time than you to scrutinize. No, way less. And he said the only thing he looked for is the determinism. Is this person going to do this no matter what? And all of his question. And that's so cool. All of his questions were around that one very thing.

What if this? How would you approach that? How have you in the past and the good old? Why are you doing it? Like, you know, what if this comes up? Like, what if someone offered you, you know? I had a conversation with a friend a few years ago, and he gave this wonderful example of champions. He says, everybody looks at champions to try and find what they have that other people don't have,

but they've got it completely backward. Champions miss something that normal people do have, which is an off switch. Yes. And when you're talking about a zero-sum game, or a game that's more competitive around a world, you're looking for somebody who will go to unreasonable lengths. And I suppose this is why strong ethics too,

if you care about the ethics of the companies that you're going to invest in, because that chip on shoulder, that determinism. Could push you right across the line. Very, very, very. A lot of these people live on the line. Yeah. It's just, it is where it is.

When you said that, I couldn't help it. And it's horrible. The accident she had, but I couldn't help but think of Lindsey Vaughn. Like, she had a- Who's that? Lindsay Vaughn's the downhill skier that's 4142 and is in the Olympics right now. Okay. And, you know, she had retired a while back and came back, trained again.

Her trial times were highly competitive. But early, when she got to Italy, she injured her ACL. and she put on a brace and said, I'm going to compete anyway. And unfortunately had an accident that went to the hospitals, had three surgeries. Snap to shit. Yeah, but to be in your 40s

and coming back. In some ways, like, somewhat injured, and I'm like, I'm going anyway. I'm sending it anyway. Look, I didn't know about this story. This just happened, like a week ago. I kind of like it. I kind of like it.

What a way to go out. Yeah, okay. Fair enough. You're going to be laid up. Better to burn out than to fade away. Well, could you imagine, again, that is, and this is a fucking wonderful little microcosm of exactly what we were talking about. What about that open loop?

Yeah. Would my ACL have held up? Yeah. Would it have held up? Am I going to go back at 45? No. Not going back at 45. No, no.

It's the last shot. This is it. Yeah. So I kind of like it. Fair enough. I'm sure that her surgeon doesn't like it. Oh, maybe he does if he's paid. well, but I'm sure her physio and a strengthening

commission coach don't like it. Yeah. Going back to the founder thing, is the founder more important than the company to you in some ways? Would you bet just on a founder that this person will find a thing? Well, here's one proof point that would speak to this is there are multiple companies

that the original idea completely failed and the founder was able to pivot to something entirely new and be wildly successful. Slack is an example. It was a game company, and the game failed, but they had built this tool to develop the game. I didn't know about that. It's so cute.

Discord, who's one of our companies, was also a game company that failed and launched this Skype alternative for communicating during games that became wildly successful. And for any venture capitalists that's been through one of those pivots, they're famously known as pivots now, it's all about the person. Like, it's all about the founder. Like, there's also a data point that most venture capitalists will quote, and I'm sure it's not scientific, but a new CEO hire is a 50-50 bet at best. So why, if you're doing positive, like trying to run MPVs, would you even take the wrong? risk of hiring a CEO because you're going to, there's a 50-50 chance you'd just get a bad

apple, in which case it's all toast. So, yeah, there's, and that lore goes beyond me. I mean, I think the founder mythology, if you will, is quite high in Silicon Valley for all those reasons. Now, there are times where you have no other option, and there are, there's way more stories. This is kind of an odd fact, but companies that serve businesses have a much higher success rate of replacing the founder than companies that serve consumers. Why do you think that is? My best guess is consumers are more fickle and that that product thing is just more artistic. You know, more like to taste again. Yes, more like a movie than business. And business products are more systematic.

Yeah. Yeah. And you can algorithm that down to... Steve Jobs once said that the difference is the buyer in a business isn't the user. Hmm. And he made that point. And that may be it, like, that may be the essence of it. That's cool.

I, um, this thing, the beverage that you're drinking is mine. And that's the first big company that hasn't been something that I've directly operated aggressively myself that I've founded. And one of the interesting elements that I've seen with this, where we did a raise last year, we raised $3.4 million, and right now we're in the middle of raising six and a bit. I'm watching Luke, who is one of the co-founders. Today, he drove from Portsmouth on the South Coast to Leeds,

which is five and a half hours away, It's a fucking forever away. Drove to Leeds for one investor meeting. Just sit down with this guy. And when you think about, as you're sort of reeling off, all of these different traits that you would have, sort of the obsession, the determinism. And what's been cool is to see,

you almost get to learn what people think of you when you do fundraising. When you're trying to get cash to inject into a business that's yours, you almost see in the responses from people. And a couple of times we've sent the decade, out. This was in the first one. So we send this deck out and it's all sexy and it's got the numbers and the projections and all the rest of it. One of my friends sent a reply to the deck and he made a meme. Have you seen the Midwit meme? You're familiar with this? On the left hand side is sort of a

Neanderthroar guy and on the right hand side is a sage that looks like a Jedi. In the middle is a guy that overcomplicates everything and he's sort of screaming and getting. The joke is that the guy in the left and the guy in the right always agree. If it's going to the gym, it's lift weights eat protein, lift weights eat protein, the guy in the middle, I must ensure that my scientifically accurate, predigested way is consumed within a 30 minute. And he replied with that meme. And he said, the guy in the middle said, read the deck, make expected value calculation, check against finances. And the guy in the left and the guy in the right said, I bet on Chris. Yeah. I bet on Chris. I bet on Chris. I bet on Chris. And it was really interesting to see, do people look

at you or Luke who's my guy or James who's one of the other co-founder to they look at you and go I just you'll make it work no matter what yeah and uh that was cool it's the first time that you can take that too far I've met with founders who who are anti-deck I even wrote a blog post called in defense of the deck because they got to make sure that you don't misspell one of those words but yes they walk in the they walk in the room and just want to chat and you know nothing about the business. You know, Jack, shit, and I don't want to learn about the business through a prompt with this human. Like, it's too hard. You can't get enough information fast enough through that. So I, and I, in this blog post, which I'd encourage people to find, I show Steve Jobs,

Mark Benioff, Jeff Bezos in front of a deck. Like, it's good. It's good enough for that. No, no, no, no, I don't disagree. I'm not advising people. People are prepared, if you fucking investing in Newtonic, please scrutinize that. But I want to say one other thing about this because I think it gets more to the point of what you said. Most people perceive venture capitalists to be making investments the way maybe a byside public investor might be. If it's positive IRA and I'll make 14%, I'll do it. But venture capitalists have a limited number of boards they can go on, probably two a year. And so they don't have limited shots, the unlimited shots on goal.

They can't fund everything that's over 12% hurdle rate. They have to fall in love. And it goes back to what we were saying with stories and all this stuff about people. Like, they're going to pull the trigger because they have an emotional, positive bias to go do this thing. Does that tap's in, it's about Chris for sure. Yep. But they also need to kind of love the category and love that. idea and want to spend 10 years working on the problem, like all those things.

Like it needs, it, they have to flip from zero to one in their own head, in this human's head. Does that make it harder for businesses that are less sexy? Of course. Unquestionably. That's why there's like these, uh, these mid-market PE people. Like they go do, they go do those things. I don't even, I would never be motivated by. Right, but, you know, I'm not necessarily shitting on them too bad.

Like somebody, there are, you can make money. There are things to be done, you know. But I also would say, and I think this is important, there are businesses that shouldn't take venture capital. And a series A typically leads to a B and typically leads to a C. And the ownership that a founder has can shrink pretty dramatically. And then the exit value you need to make the same amount of money had you sold it 100% on sweat equity is now 10 times higher. And just make sure you think through all that.

Somehow, through the use of these 19 credit cards and everything, fucking guy behind Tito's. A hundred percent of his. Unbelievable. Do you know Jim Shark? You're familiar with Jim Shark? No. So it's probably one of the biggest British companies to activate.

I'm actually wearing the trousers right now. And Ben, the CEO and founder, is a good friend. And it is a 2.6 billion pound company. And it is entirely private. And I think he's still got 75% of it himself. It's a lot. But I would say even if you're going to sell for 20 million, there are far more companies that want to do a tuck-in 20-million.

million acquisition, they want to do a half a billion acquisition. What's the size of the market you're selling it to? Well, plus, if you're a large public company, you can do a $20 million acquisition without filing anything, without telling anybody, your boss won't care. If you own 100% of a $20 million company, that's lifetime wealth. Like, trying to make $20 million selling a company for half a billion, that's hard. Because it's hard to sell a company. There's fewer people that can buy it.

It's going to have more scrutiny that goes over the money. the top of it. You've now diluted down. You need audited financials. You need like, they're going to have to file an S8. There's all this stuff. It gets, it gets really hard to sell a company. I don't ever think, I don't ever think about the market of selling a company. You think about the market of the company that it sells to. Yes. That's so cool. Yes. Yes. Yes. It matters. It really matter. It really matter. And by the way, if you sell that first company for 20 million that you own 90% of and you want to go take the big shot and raise money. Oh, great. Now you've got freedom, flexibility, you can take all the risk you want, you know. Do it the second time. I've seen,

I've heard a bunch of different horror stories about founders who've diluted down and diluted down and diluted down. And then before they know it, they're like, what the fuck am I working for? No doubt. Lickpref is a beast. What's that called? Liquidation preference. So venture capitalists typically take preferred stock and it has a turn. called liquidation preference, which means in a sale, they get the option to basically treat it like debt. They get paid out first in a sale. And so if you've raised, in these days, these AI rounds, if you've raised $500 million, like Common doesn't even participate until you get a sale over that, technically. Now, it's often there are carve-outs because they have to get something done. But

the bigger that number gets, the more weighty it is. Yeah. I mean, I feel fortunate when we did the first raise. I bought back in. I didn't want to dilute. Oh, nice. I threw more money in. I threw more money in, actually.

And by the way, the investors love seeing that. Love, love, love seeing that. I was like, I am not. In fact, I gained share of Newtonic when we did the raise. So I bought in over the top of where I was already while we were diluting down. Hard to do. It was. I mean, James wanted a new Porsche,

and he was very gracious, and we shifted some stuff around, and I can't remember where else I talked about that. That's awesome. But no, it was cool. And it's been really fun sort of learning about that world. And now being able to see what's happening, especially in the world of AI at the moment. Well, that's a question.

What are you most excited about with regards to the industry of AI, and what do you think is overblown. I mean, it would be a little redundant, but the thing I'm most excited about is just the personal empowerment.

You know, there's all kind of anthropologists that will tell you we evolve with our tools. Humans, like, it's very clear, right? If I had a plow and a tractor and a, and a computer and a chemistry set,

and the other guy's the guy naked and afraid, like, I'm going to be more involved than I can do more stuff. And this is the latest of those things. And anyone that is a skeptic or, and I've met a lot of, like the top academicians that are skeptics and all this, you are, you're no different than the Luddites with the looms in Europe. Like, you're just not. It's the modern version of that. And the number one thing you can do to future proof yourself is to run at it. Like to know, whatever industry you're in, there is an edge of what is AI capable of in this industry,

and you want to be right there. You want to be aware of exactly what that is. And if you are the most AI productive human in your field, you're not getting fired. You're the one they're asking all the questions of, like, what's this capable of? And so in the chapter I have on Honia Craft, I say study the history and study the edge. Like if you can quote from the founding fathers of your industry and you know exactly where the technological edge is, you look like a unicorn. Going in the middle is why you die. Yeah, I mean, everybody knows the middle.

Like I'm just talking about differentiating yourself. Of course, of course. Yeah. So anyway, I find, I mean, I haven't. I'm anxious. This is why I also why I was a useful, I use the word useful venture capitalists, I have FOMO about new shit that I don't understand. So up until at least a year or two ago, if something shit,

if there's an app in the app store in the top 10 I've never heard of, like hives, like I have to know. You're allergic to ignorance. I'm coming off of it a bit because I haven't done a claw bot yet, which I feel guilty about. Well, you can't get a fucking Mac Mini. That's why. You're not going to be able to buy them.

They're all sold out. But I feel guilty about that. Yeah, yeah, yeah. You've got massive FOMO. Yes, but it's useful. Like, and so anyway, I think that there, I would also say this about AI. If you're not leaning in, not only people have said there's prompt engineering skills. Not only are you not learning that, but I find every day I think of an,

new way to use it and a new way to test what it's capable of. And if you're in it every day, you're helping to explore that boundary and you're all the sudden learning new things. Do you understand what I'm saying? Like, I had this great experience with the concluding chapter in the book. So my, you know, almost done wrapping up, feeling good. And the editor says, take a shot at the conclusion this weekend. So I spent six hours, seven hours. I sent him something. He's like, this sucks.

Like, first time, like, it was really the first critical, he didn't use that phrase. I really don't like this. So I asked Chat GPT in the pro version, the $20,000 a month, whatever it is, write me a 20-page report on the best concluding chapters in nonfiction books of all time. And give me a summary of each and what made it special. And in reading through that list, I noticed that eight or nine of the ten took an orthogonal direction to the book. So it didn't summarize. It brought in a new perspective.

And that gave me an idea. I then went and ideated on that concept. And it gave me a new idea to take it in a different direction. And the editor loved it. Huh? What was the idea? Um, the, not, I, I'll give this one away. Um, the concluding chapter's titled, It Ain't Easy. And so the whole book is an exercise in trying to encourage you to go do this. And this is a little warning at the end. Like, it ain't easy. You got to struggle. You got to suffer. You've got to be okay with failure. In praise of the grind. Yes. And the editor loved it.

Good. I think that's an important message. Yeah, so if I don't have AI, I don't do that. Like, you know, and it didn't write it for me. It just gave me a new lens for how to think about it. When it comes to the AI thing, what do you think it's going to do to the field of work generally? What areas would you be worried that are going to be obsolete? Anything that was synthesizing, I mean, so the LLM, large language model, is really,

really good at text, really, really good at text manipulation. So if your job involved searching for text, summarizing text, anything like that, paralegals are already under threat, and I have talked to lawyers that have drastically reduced the size of their paralegal force. I've talked to them. That has already happened. coding, it turns out, is highly structured text, more structured than text itself, right?

If you think about it, it's got more... There's more rules. There's more freedom in actual language text than encoding. And that makes... And so coding's under threat. And the best people that will write or will generate the most code in the future are the ones that learn to be able to harness that tool the way a farmer learned to use a tractor instead of plowing.

And that's your only choice. Like there's no hand hoars anymore. Like they don't exist. And so this text thing's a big deal. You know, if you translated something, that's a dangerous job. Someone needs to kind of make sure the translation's right. But that's a different job. It's more of a editor of translation, right?

And that's an opportunity to move upstream. Be the one that's best at exercising that with this tool. But the old tool doesn't work. Like, it's not going to be real. If you were 21 and starting again with no knowledge or connections, what do you think you'd be focused on? What would you do? It would definitely be related to AI.

I mean, it just would. Like, I'd be rolling around. in it more. I would definitely have already launched 10 claw bots versus now where I don't have that need to see what's possible. I'm fascinated by the agent idea for a personal assistant like a running buddy. I just find that fascinating. Another one that I kind of am fascinated by, I think someone will build a new CRM from scratch that will be used by small companies that don't have a CRM because it's easier to start with zero in the database. And I think that will be super clever, that product that I don't think you can get there from Salesforce because you've got this

huge database with all these fields and forms that no one wants to look at. And if you start with that as your construct, I think you'd build the wrong thing. Does that make sense? Because you're trying to backwards integrate something that's already a little giant. And I don't think the user wants to even see that stuff. That's interesting. And so it should, whatever the storage mechanism is, I don't think it will be visible to the user in the way that a database, like, type enterprise app historically did it.

Mm-hmm. You know. So, so anyway, those are things that. pop into my brain when you say that. Those are things I'd be playing with. I know that you're a big reader. What have been the books over the last couple of years that you have not been able to stop telling people about? The second half of range impacted me in a... David Epstein. Yeah. And the book's known for being this antidote to Malcolm, although they're very close friends. In fact, Malcolm's quoted on the cover of range, I think. Um, um, um, but the book's known for being this anecdote. And

book people talk about this generalist versus specialist and this comparing of, you know, these two athletes. But he gets into a very different subject in the second half of the book. He gets into this notion, which I had always heard a phrase called far analogies, but he gets into this notion that people that switch industries or switch careers or switch academic focuses tend to be the biggest innovators. of all time. And they come into something with a different mental model than the people that came up through the field. Like if they enter through the side door, you understand? And it relates to the generalists. Yeah, yeah. And they're able to bring patterns from or see patterns other people may not

see. And I just find that fascinating. I touch on it in a couple of the chapters. In the learning chapter, in the peer chapter, I say, if you make it far enough, you want to stretch the peer to someone that's maybe in a different industry. You want to stretch the learning to other industries. And it's where you find some of the biggest nuggets. It's more noisy. You're waiting through. Like, it's harder. Less aligned, right? Yeah, yeah, yeah. But the insights are power loss step changes. It'd be like you, like, listening to someone talk about, great writing technique and get an idea for the podcast. You know,

but one of the things that I did about four years ago when I first moved to America was I got obsessed with cinematography. And cinematography, we obviously, there's cameras and videos and stuff here, but we started doing this thing called the cinema series, and this was shot like a movie, and it culminated episode 1,000, was me recreating the house from Interstellar on a 85-foot video wall,

biggest video wall in Texas using the same technology that Star Wars uses. Yeah. And we rendered the entire scene in Unreal Engine 5 and then did set dressing. So we had live elements of dirt on the floor and cactuses and we reversed a fucking airstream in. And I sat opposite McConaughey. And I sat him down, 11th anniversary of Interstellar. And we were sat in front of the house from the movie.

And that was because, oh, I started learning about this and I started getting friends. that were from the cinematography industry, and I started asking them, what would you do if you were trying to elevate a podcast? And then we did some cool things. And it's largely a passion project wing of what we do, but it's cool. In his famous Stanford graduation speech,

Jobs said if he had never taken the calligraphy class, he doesn't know if he builds the iPhone the right way, you know, and the Mac, you know. It may or may not. It may be, it may just be kind of nostalgic, speaking, but there are things you can borrow from learning far away that can be very impactful. And it's hard to know at the time, like when you're consuming it. That's why I call it a bit of a superpower, or advanced level, I think I call it.

It's not easy. But because you're translating, it's like an exchange rate between something else and this. So is that just cool for them, can really take what that musician's doing? Or is this relevant to me? So I guess taste, discernment. And when I think about areas that AI can't replicate, community, networking ability, taste, discernment. Yes, I agree.

Those are the, I'm sure there's tons more, but those are the ones, at least for me, with what I do. It's not going to build a friendship with this other person that I want to hang out with. I agree with that. It can't choose, is this the right guess? And the Mr. Beast approach would be, well, there are just quantifiable metrics of how this person appears on a balance sheet. What's the likelihood of this person being a big play guest or whatever?

But that also doesn't account. That's a local maxima, which is everybody's got the opportunity to operate for that, to optimize for that. Whereas if you're trying to refine for the taste, that's very different. Heck yeah. Bill Golly, ladies and gentlemen, Bill, you're fucking awesome. Thank you for having me. I really appreciate it. A lot of my friends said you're going to love his energy, and sure enough, you're a legend. I'm glad that you're occupying some of those high rises down.

I've always wondered who lived in them. It's good. Where should people go to check out everything you're doing? So I've historically spent most time. We were an investor in Twitter early on, so I've developed my ex-profile the most, and that's where I post most stuff. So it's B-G-U-R-L-E-Y. there's a there's an instagram account that i'm for the first time in my life developing for the book

congratulations welcome yeah it's a different world like i feel like such a neophyte like in twitter i get everything in like i understand instagram's a different language yeah it's a different language i'm figuring it out heck yeah bill i appreciate you thank you sir bye if you're wanting to read more you probably want some good books to read that are going to be easy and enjoyable and not bore you and make you feel despondent at the fact that you can only get through half a page without bowing out. And that is why I made the Modern Wisdom Reading List, a list of 100 of the best books, the most interesting, impactful and entertaining that I've ever found. Fiction and nonfiction and there's real life stories, and there's a description about why I like it,

and there's links to go and buy it. And it's completely free. You can get it right now by going to Chriswillex.com slash books. That's Chriswillex.com.com Books.