Modern Wisdom

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

117 min
Mar 14, 20263 months ago
Listen to Episode
Summary

Bill Gurley, former Benchmark venture capitalist, discusses his book on career pivots and regret minimization. He explores why 60-70% of people experience career regret, the importance of finding passion over pure perseverance, and how to strategically transition careers by building peer networks, continuous learning, and understanding your true motivations before making major life changes.

Insights
  • Career regret stems primarily from inaction (boldness regret) rather than failed attempts; humans ruminate about what they didn't try far more than mistakes they made
  • The education system has become a 'conveyor belt' that forces early career decisions (age 17) while simultaneously delaying adult independence, creating anxiety-driven career choices
  • Passion and perseverance are equally important; over-indexing on grit without passion leads to burnout, not success—the best performers are obsessed, not just disciplined
  • Founder success depends more on determinism and product instinct than the initial idea; pivots from failed companies (Slack, Discord) prove the person matters more than the concept
  • AI amplifies existing traits: those passionate about their field gain a 'jetpack' for productivity, while those grinding without passion face existential threat from automation
Trends
Rise of 'regret minimization framework' adoption in career planning and decision-making among high-performersShift from finite-game (zero-sum) career mentality to infinite-game peer collaboration models in knowledge workIncreasing recognition that generalists and career-switchers drive innovation by bringing cross-industry mental modelsGrowing emphasis on 'hidden metrics' (passion, fulfillment) over 'observable metrics' (salary, title) in career satisfactionAI-driven productivity tools becoming differentiators; those who master AI tools become indispensable rather than replaceablePost-40 career pivots becoming more viable and socially acceptable as lifespans extend and skills remain transferablePeer networks and continuous learning replacing traditional mentorship as primary career development mechanismsFounder-led companies maintaining innovation at scale through single-ordinating principles (e.g., customer experience, mission alignment)
Topics
Career Regret and Boldness RegretRegret Minimization FrameworkPassion vs. Perseverance in Career SuccessEducation System and Early Career Lock-inPeer Networks and Co-learningFounder Determinism and Product InstinctCareer Pivots and Second ActsAI Productivity and Job DisplacementContinuous Learning as Career DifferentiatorMentorship Models (Aspirational vs. Transactional)Financial Flexibility and Career OptionalityNarrative and Storytelling in Career MotivationGeneralist vs. Specialist Career PathsVenture Capital Investment CriteriaPost-40 Career Transitions
Companies
Amazon
Jeff Bezos's regret minimization framework and customer-centric decision-making cited as model for founder determinism
Slack
Example of successful pivot from failed game company to communication tool, demonstrating founder importance over ori...
Discord
Another example of failed game company pivoting to successful Skype alternative for gaming communication
Uber
Mentioned as company Gurley could have written tell-all book about but chose career regret book instead
Open Table
Company Gurley was involved with; used to illustrate Danny Meyer's restaurant industry impact and culture
Shake Shack
Danny Meyer's restaurant company demonstrating how founder passion creates lasting cultural impact on employees
Compact Computers
Gurley's early employer in Houston where he worked as engineer before transitioning to Wall Street
D.E. Shaw
Jeff Bezos's employer before Amazon; used as example of high-paying job that could lock someone in financially
Microsoft
Ben Gilbert created Microsoft Garage as side hustle, demonstrating how side projects lead to innovation
Madrona Ventures
VC firm where Ben Gilbert transitioned and started podcast, leading to Acquired podcast success
Lux Capital
Josh Wolf's VC firm; quoted on importance of 'chips on shoulders' in founder selection
University of Texas
Where Gurley gave MBA presentation that became foundation for his book on career regret
Wharton
Conducted scientific survey on career regret, finding 6 out of 10 people would choose different career
SurveyMonkey
Platform used for initial career regret survey showing 7 out of 10 people would start over
Gymshark
2.6 billion pound British company that remained private; founder retained 75% ownership without VC dilution
Tito's Handmade Spirits
Bert Beveridge's bootstrapped spirit company; post-40 pivot example from seismology to oil/gas to mortgage to spirits
Twitter/X
Early Benchmark investment; Gurley developed X profile as primary social platform for sharing ideas
People
Bill Gurley
Former 25-year VC discussing career regret, pivots, and his book on finding authentic career paths
Jeff Bezos
Developed regret minimization framework; uses determinism as sole investment criterion for founders
Elon Musk
Uses 'get us to Mars' as single-ordinating principle; maintains innovation at massive scale
Daniel Pink
Wrote book on regret; identified boldness regrets (inaction) as biggest life regrets, worsening with age
Angela Duckworth
Wrote 'Grit'; later acknowledged over-emphasis on perseverance without passion leads to burnout
Steve Jobs
Calligraphy class example of cross-industry learning influencing product design; cited on buyer vs. user
Danny Meyer
Example of founder creating lasting culture; continuous learner who influences entire industry
James Clear
Noticed Gurley's YouTube presentation on career regret and promoted it, leading to book development
Jonathan Haidt
Discussed education as 'resume arms race'; advocates for play and exploration in childhood
Jean Twenge
Wrote 'Generations'; discusses extended adolescence and premature career lock-in of young people
Rick Rubin
Advocates for play and exploration in child development; emphasizes importance of unstructured time
Bert Beveridge
Post-40 career pivot from seismology to spirits; bootstrapped to become best-selling spirit in North America
Chris Del Conte
Built peer network of 8 D1 athletic directors who all started at bottom; demonstrates power of peer learning
MrBeast
At age 17, found 3 peers to hack YouTube algorithm; 40,000 hours of shared learning vs. 10,000 individual
Ben Gilbert
Created side hustles at each job; Microsoft Garage led to founder connections; later started Acquired podcast
Steve Harvey
Father supported his TV dream despite teacher's criticism; example of parental permission enabling boldness
Matthew McConaughey
Father told him 'don't half-ass it' when switching from law to film school; example of supportive push
Jen Atkin
Most successful hairstylist; moved to LA with $300; built beauty brand and sold company
David Epstein
Wrote 'Range'; argues generalists and career-switchers are biggest innovators due to cross-industry patterns
Malcolm Gladwell
Wrote '10,000 Hours'; Epstein's 'Range' serves as counterpoint on generalist vs. specialist debate
Quotes
"Life is a use it or lose it proposition. You're going to get to the end and then it's done."
Bill GurleyMid-episode
"The biggest regrets people have are regrets of inaction. Humans are great at forgiving themselves for mistakes, but they ruminate about what they didn't try."
Bill Gurley (citing Daniel Pink)Early episode
"Enjoyment is efficiency."
Joe HudsonMid-episode
"I just want you to know the only reason that I'm here is because of her."
David Goggins (pointing to his assistant)Anecdote
"Chips on shoulders put chips in pockets."
Josh Wolf (Lux Capital)Mid-episode
"The only thing I look for is determinism. How is this person going to do this no matter what?"
Jeff BezosAnecdote
Full Transcript
What got you into thinking about the idea of career regret as somebody that's had a very seemingly successful and fun career? Why do 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. it. 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 MBA 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 it further and making it this way. But you used the word regret. We did, along the way, I launched a survey on SurveyMonkey 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 Wharton People Analytics, and they did a more scientific version of it, much broader audience, and came back six out of ten, but very similar. And that notion of career regret is interesting. I had the opportunity to talk to Daniel Pink, who you may know, who wrote a book about regret. And in that book, he says the biggest regrets people have, and he showed me a graph. It actually gets worse as you get older towards the 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, learned 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 belt. 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. 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. 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 they just love what they do. And not only are they more successful, but 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. and do oh i 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 um thinking about the fact that we seem to regret inaction boldness regret yeah have you reflected on why you think that is what it is in the the human mind that causes us to prefer this decisiveness over uh 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 ifs, to build a story, especially a positive story around the what if 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'll be familiar with the Zygonic effect. I'm not. Tell me. Oh, cool. So there 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. He's insane. I'm definitely going to get something wrong. And sometimes you might go, I'm going to, we'll take the sprouts by extra bacon, no goat's cheese. But you want to just see if, all right, I missed a no notepad. And the study ended up finding out the Zygarnik effect, 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 that you 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 room did you stay in two hotels ago i'd give it 7 35 i don't know i have no idea um it's the same reason why cliffhangers work at the end of TV shows to get you to watch the next one. Yes, yes. The open loop, the human mind abhors an open loop. Yeah. 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. Yeah. Now, the human mind abhors open loops 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? 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 boldness regret. And in my own career, 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 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 uh it is a really wonderful idea and um i guess jeff's got other stuff that he can be well known for so perhaps you know well it's it's actually quite synonymous with the uh the uh one of the seven habits of highly effective people begin with the end in mind it has 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 in both inside of their career and outside of it you must have reflected on this a lot yeah i have one one thing that i think i especially with with the modern young people i think one problem that i think exists because we've built this i call it in my book a conveyor belt uh jonathan height called it a regret or a i'm sorry a uh resume arms race we've built this 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 throwing away the investment. Does that make sense? Like a loss aversion type thing? 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, you know, this is despite the fact that 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 mention this to young people, there is this weight. There is this weight they feel, like an obligation to – Decisions that they're locked in when they were 17. Yes. Well, and that's another thing. And 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 you're 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. But 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. He has a chapter called Let Them Or The Loss of Play or something. Rick Rubin's been pounding on this. He talks about it in his book. 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, sort of twins with some of Hyde's stuff. You'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, the 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 uh less alcohol less casual so 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 the socially very immature professionally expedited and he ties them together it's just gene 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 um now there might be some rebellion going on that oh god everything just feels like i need to get my act together i how can i do these other things i just so much of my cognitive real estate is taken up i could see that maybe that would be compensatory yeah um like i i mentioned i think uh when when about 10 years after duckworth wrote grit she said that she wished she had positioned it as 50 50 passion and perseverance and she if she could do it again she'd put more on the passion because she thinks we taught a whole generation of of the high performer children how to grind like we taught them to persevere which is well and so i get that i grit was a massive book i don't think that she should lay at the feet of her pen the the issues of this stuff but i think one of the reasons why from a personal development standpoint it makes it's a bit more seductive to over index on the perseverance than the passion is the passion feels more difficult to engineer fair enough uh 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 what is 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 the the boldness regret right like you're going to get to the end and and then it's done and and only if you think in the way that Bezos 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 like that you can't leave. and you can do it with personal commitments as well. My second career was 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. They tried to get into the membership club. They spent right up to the limit, and now you can't switch. You can't switch. 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 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 um 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 those 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. Twice a year, they run lab tests that monitor over 100 biomarkers. They've got a team of expert physicians that analyze the data and give you actionable advice to improve your health and lifespan. And seeing your testosterone levels and tons of other biomarkers charted over the course of a year with actionable insights to actually improve them gives you a clear path to making your life better. Getting your blood work drawn and analyzed like this would usually cost thousands, but with Function, it's just $499. 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, it's weird, isn't it? because flexibility is actually a really difficult thing to show off. It doesn't... Even flexibility is only show-offable in so much as you can take a photo of you on a plane or you at a holiday, 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. and we'll often trade a hidden metric for an observable one. Sure. We'll trade the quality of our sleep for a slightly bigger pay packet. We'll trade the hours of peace that we have on a Saturday for position improvement. Some people will trade a caring, supportive wife for a very difficult, younger, hot one. 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 what why 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 uh why why should i try and optimize that is is being fulfilled at work a luxury um 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 may they may not perceive to be an occupation that could be a religious community it could be volunteer work that they do um 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 i'm not casting any any shadow on that whatsoever um if you are the type of person that is either unhappy with your work like so much so that it's impacting your quality of 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 the 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 um there's this there's a there's a great story that there's a couple of these actually but i'll i'll choose the steve harvey one there's a there's i don't know if you've seen this but you know who steve harvey He is the comedian who does the family feud now. Yep. He tells this story. I think he told it 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 it 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 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 bed stand, 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 for parents, and I'm a parent of three, and I've lived 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. 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 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 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 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 uh so i guess one of the situations that so many people must be in is someone one version of them successfully pivots and another version of them stays stuck for life yeah why do some people successfully pivot and and others end up getting stuck well i mean there's a there's you could come up with a number of things one of them is financial which we've we talked about you could be overspending there's a there's a different case where you're just you're you're stuck financially like you need your living hand to mouth um there's a i have a 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 went not only achieved touched the top rail of that but then launched beauty products sold that company but she moved to la with 300 in her pocket and that's not to say anyone can do that but like there there are stories of people with near nothing starting on the very bottom rung and finding their way to be successful there's this classic meme of starting in the mailroom in hollywood and david geffen and and barry diller all these people started in the mailroom you know it's that it's about as low a 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 um 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 that matthew had told him he was going to be a lawyer and he was supporting that but but that weight can be there too like you may feel i think there are certain um there are certain uh cultures where where like being a doctor is considered really in russia like being an academic was so you may 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 i what if this doesn't work it's sort of ambient yeah ephemeral this fugue fog thing that's come down on if you if you allow me like to give you a little history of how um or why i would say i spent i spent six years turning the uh the original presentation into a book and i i 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. 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 size 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 do a do a do b then do c but they don't 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 favorite 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 and uh 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 i 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 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 just straight up does not stick. Pithy mantras and quotes and stuff can do – they're a nice compression algorithm, 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, you know, 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 Longreads that 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 Suge Knight and Snoop and i think biggie were on the cover of new york time 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 uh 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 wolf put together the first one and then the second one has krakauer and lewis and like all the modern now we've seen we've seen this pivot into substack right that that uh people that were previously hardcore 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-turn thing and loop back on yourself enough and you end up in charge of CBS you're Matt Taibbi and you end up in charge of the Twitter files or whatever I'm a huge Barry fan uh so talk to me about the risk of starting over in your 30s or 40s yeah 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 is really you're telling me i'm going to start again 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 40s well what i mean one thing i would encourage you to do there was a there's a this book i read when i was really in i think back in business school called shark proof by harvey mckay he wrote he's known for a sales book but he wrote a book about careers and he said to keep your dream job he this was an older book so he said keep it in a manila a folder and a file, but you could create it 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 occupying 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, 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 Burt Beveridge. Burt's nickname is Tito, so 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, not sure he equated his identity to being a mortgage broker. And one night, this is such a, like, 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 the 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 and he's like hanging out at bars on the left like and and um he didn't know jack 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 text um but of course Cheetos is now the most best-selling spirit in North America he uh owns 100% of it himself no way the whole thing's bootstrapped yes oh but it's such a great story like it's just such a great story and and and and 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 see I had a I had a young person at john hopkins raised their hand and say but i i don't want to chase my passion i want to be purpose driven and i i thought to myself you know every profile in the book these people are touching more lives than they could have ever imagined like 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 i'm my my main goal in life is to help other people serve yeah okay that's interesting well it's like no it's 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 um this person there are some jobs that just suck yeah there are some jobs you're serving your country or you're you know 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 um 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 yeah i mean one of my favorite on that front is i 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, that'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 had taken all his chefs on a tour of Europe together, jotting notes, learning, like just constant learning. That's so cool. Which I think is, that's the second principle of my book is continuous learning, but it ties in with the first one. The best test is 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 that continuous learning is just you enjoying life, you know? and if you find that you you found 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 five takes things to the next level it now includes a temperature regulating duvet that works with the smart mattress cover to deliver full body climate control maintaining your ideal temperature from every angle all night long. The new base also includes a built-in speaker so you can fall asleep to ambient sound rainfall or Dr. Andrew Huberman, whatever helps you switch off. And with upgraded biometric sensors, it now runs nightly health checks identifying disrupted breathing, abnormal heartbeats or sudden changes in your HRV. 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Joe Hudson's got this line, enjoyment is efficiency. he says I like that I think it's really really true yeah that people 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 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 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 ex or something yeah um 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 you know i'm not 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 in it. The one that I live in right now is still podcasting eight years in, a thousand episodes. Every single house has had, every Airbnb that I've stayed in, I get there and I fuck. I'm researching hotels to see if the depth of the table can withstand my MacBook, the stand and the tripod because that's what i want to do that's what i want to do i want to have these conversations so okay i i my entire life gets warped around it i'm sure you'll be familiar with the uh 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 uh but Musk says, does this get us closer to Mars? Does this get us closer? 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 of. They didn't get laden down with diseconomies of communication, lumbering fucking behemoth bullshit. It's a democracy 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. It's Dworkesh. Yeah, this came up. This came up. 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. You can't be deep. There's 200,000 employees. and Elon jokes, yeah, there's 200,000 employees. You have to have some heuristic, simplifying heuristic that can spread through their brain. Or else they're spinning too many plates. Yeah, exactly. It's pretty impressive. It's super impressive. Okay, so career pivot fear. Yes. Someone is in the career. 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 so on the on the do you know? I mean, I love I love this test of is 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? Get busy living or get busy dying. And, like, if you know that's true, like, well, now is when you 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 of what you might do next. Like, you know, fill them out. AI can really help, right? Like, you could build a 20-pager on each one of these career paths. What might I like? What might I not like? What are the three things people love in this career? What are the 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 heuristic in the book that I borrowed from from Ben Gilbert at acquired a 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 proactive so it reflects positively on you when he ended up at Madrona VC asked him if he could start a podcast and look where that led and I just had dinner with both of them and they were in Austin and man they're happy like I gotta tell you like they are really happy people so similar to you and uh your obsession and and they fell into it through that through getting there through that way so i think those are some things you can do to uh to test and then look what are you doing in your spare time like are there any signals there um 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 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 with my friends but even when i'm not playing i'm always thinking about it a lot let me maybe this is you know maybe there's something going on let me share this fun story i just stumbled on because i was i was i'm i'm using some hacker techniques to promote the book, and that led me to talk to this gentleman. And when I pinged him, he said, oh, 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 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. 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 you can underperform in a industry that you don't want to be in yeah the prospect of potentially doing okay one that you love is infinitely better i think so i think so that goes back to life is a user list of propositions Like, give it a go. And then the other thing to know about failing in that is humans are like this. The research in psychology says humans are really good at forgiving themselves. Like you're not the failure is 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 exciting. And even if it's objectively a little worse, subjectively, it's all new. Yes. I liked it. 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 repot. 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. Yeah. 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, but are 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 asked. 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? 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 can just absolutely absolutely finesse my way out of there's 10 other reasons why you should build that group but that's 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 out gun 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 in 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 once you get to that place, it's a really special place. There's a story in the book about Chris Del Conte, 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 D1 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 sharing, they were 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 that 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. it's not the exact math but it's a it's a 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 improve heart health and are backed by hundreds of studies but here's the thing all omega-3s are not made the saying. Most brands cut corners, they use cheap fish oil, skip purity testing, throw in fillers, and call it a day. But with Momentus, you know you're getting the highest quality Omega-3s on the market. They're NSF certified for sport and they're tested for heavy metals and purity. So you can rest easy knowing anything that you take from Momentus is unparalleled when it comes to rigorous third-party testing. What you read on the label is what's in the product and absolutely nothing else. Last of all, Momentus offers a 30-day money-back guarantee. So you can buy it and try it for 29 days. If you don't love it, they'll just give you your money back. Plus, they ship internationally. Right now, you can get 35% off your first subscription and that 30-day money-back guarantee by going to the link in the description below or heading to livemomentous.com slash modernwisdom and using the code modernwisdom at checkout. That's L-I-V-E-M-O-M-E-N-T-O-U-S.com slash modernwisdom and modernwisdom at checkout. What do you think about mentors? You know, peers are great they're 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 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 i think you do both i think you do both they serve very different purposes the 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 is 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 because the cfo of this company doesn't want to be friends with you exactly yeah 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 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 noticed that when i first started the show in 2018 in 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 such a funny trick that i still use now so the world can have this one uh i i realized that flattery was was one of the big drivers i think for uh bringing people on the podcast especially no one knows who it is it's this random british guy asking if you should come on i always used to ask people uh can you please put me in touch with whoever handles your podcast adverts and it's some small i get it researcher at fucking university of Arizona and they're like, oh, well, it's just me that handles my podcast. 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 still now Please pass me on to whoever handles your podcast ads And that 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 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 Bill's 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 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 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 through them oh yeah learn all you can about them like like be generous and kind and thoughtful you know good uh it will pay off big time good story around that from the show uh 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 yeah brings a new book out and uh 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 gonna have to we're not gonna be able to make it work and i was like look 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 um 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 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 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 it and and at times the experience does go into this flow thing like where when 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 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. And I don't know. I do think we get a lot of young people to do it for an extended period of time. The meat grinder thing. I just yesterday met with five of the top. I helped start this robotics honors program in 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 is what it takes to to be truly exceptional. brute forcing creativity uh sort of white knuckling your way through miserable successes uh 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 and maybe if you're just so damn competitive like winning all the time is winning is your passion it's a meta passion that's possible yeah that's interesting and that's certainly some people right they just want to win yes uh i think michael jordan would be a good example of this if you heard the novak jokovic's uh 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 um whereas you know jordan invented rivalries yeah he invented slights against himself there was 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 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 you know even at the moment where you've broken through escape velocity you're you're out in space still i don't i don't love that that much you know i love it's not the energy that i have yeah so there's a there's a there's a counter example to that there's this thing you can find on youtube where shack was on uh the that famous show that he does with with kenny and 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 thoughtful 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 ten 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 makes him look like remarkable. It really does. Like that his brain's wired that way. i i felt very proud of him like i have no reason to be proud of him and he probably couldn't care less that i am proud of him but it was uh his i like that i like that version better it feels much more pro-social yes i suppose the problem 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 true calling out all of these people and inventing random rivalries to try and motivate himself to go people would look and say you're just bitter and the same thing with shack if shack 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 sucker yeah and this is that's fair the the medium is the message but the medal is the message very much for this well and look that is more of a finite game right like that is and i did use 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. So you talk about honing your craft. Kind of interested in what that looks like in knowledge work when there's no clear scoreboard. And 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, OK, 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 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 yep what all of those people that quote tweeted it and complained about elon's horrendous working conditions fail to understand is there are people out there to whom that sounds like a dream yeah they want to work 18 hours a day fueled exclusively on high quality stimulants and chick-fil-a especially if they get to hang around with the smartest people. And they want to be pushing each other and they want to send it. They want to send the 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. six 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 are the ones you're talking about that want that experience. There were 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 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. yeah 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 um you do need to recognize that you might one day be competing with someone that has that height 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 gonna 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 the the 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 and and i'll tell you one other thing which i 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 the program you're 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 gonna out it's gonna crush me it's gonna i'm gonna lose my job look at this world it'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 than they wanted to do, and they can achieve more than they were able to before. They get to run extra fast. like so so two two people maybe in a in the same station in life ai looks like the opposite to them it's 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'm such a huge fan of Timeline. They developed this pill right here that helps clear out damaged mitochondria so your cells can actually renew themselves. And this isn't just theory. In clinical trials, people saw mitochondrial renewal increase by more than 40% in just 16 weeks, along with improvements in their overall energy. Timeline is backed by over a decade of research, has more than 50 patents, and is the number one doctor-recommended mitochondrial supplement on the planet. I started taking it nearly two years ago because it was recommended to me by my doctor. And that is why I've used it for so long, since way before I knew who made the product. And that is why I partnered with them. Best of all, there's a 30 day money back guarantee plus free shipping in the US and they ship internationally. So right now you can get up to 20% off and that 30 day money back guarantee by going to the link in the description below by heading to timeline.com slash modern wisdom. That's timeline.com slash modern wisdom. Can I read you an essay that 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 already lean in its direction. So I first started thinking about this when considering the post-MeToo instruction of don't be pushy with women right i realized that it made conscientious anxious guys even more timid yes while the dudes that were blowing through boundaries just didn't take heed exactly or another example of the prescription to just work harder yeah 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 the cults take more responsibility 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 the pieces of advice that 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 the um 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 um i do still think that developing a grind capacity is important yeah 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 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 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 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, 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. Like I've, and, uh, 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. Like, 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, the 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 are done. George, my housemate, 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 legs viscerally thinks about what it would be like to have no arms or legs for 30 minutes to be grateful is that to to and then to be reborn into this body yes with the arms and the legs so i've been i've been really pushing hard over the last 18 months uh on emotional work um trying to get below the neck as i've said and uh i think a big part of it is this that how many smart people who know all of the inside they could do an expected value calculation about the likelihood of the success and what is the objective quantifiable uh utility of enjoyment versus but then you've got hidden and observable problem coming through again um but ultimately what that strategy from george is trying to do what your regret minimization thing is trying to do is not really front load more information it's trying to overload emotion it's like oh my god there is a there's a great fucking workbook from this is tony robbins unleash the giant within but it's this weird 1994 Audible workbook and it's only an hour and a half long and I can't even find it. Listen, I've got it in my Audible. George has got it in his and 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. He wants 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 yeah three decades 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 yeah and he's trying to get you to oscillate between this pain pleasure principle yeah and uh i've had to make some you know i 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 happened and nightclubs were just reopening and 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 the movie 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 uh so this is a great idea from morgan you should 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 we did it 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 i got knowing how well life was going to go yeah so this it's the same reason that no one ever believes we're living through a golden era golden eras only exist in memory and uh 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 on my apple notes still of what if i do this thing and it goes wrong and everyone's gonna 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 for under a bridge. And it's all going to be. And yeah, I had it have not gone well. Maybe that would have been the case, but that is the worst possible scenario. And there were a million, there's gradations between the best one and the worst one. But yeah, I, I, I'm really proud of making that decision, but I, 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 even decisions which in retrospect feel very obvious i think at the time require the inhuman amounts of motivation to go to get the activation energy i get you moving i like the battle card notion i mean it's similar to similar design in your life stuff, but like allowing yourself to fully imagine the other reality, you know, and, and, 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. 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 worked for me is I think I'm very good at bringing forward the future in my brain, like, like extrapolating back, if you will, almost like a life in PV kind of thing. Just able to do that. And like reverse time travel. Yes. And, and it makes those exercises work better. You know, the fact that I somehow can do that in my brain. Um, so 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 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 right okay so you're predicting and you need instinct to get that right like you just need you got to be ahead of market humans and how humans like to interface with things and a whole bunch of stuff. So product's 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 of 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 of grit. Yes. Like not a bit. Like you want top one percentile. Yeah, yeah, yeah, yeah. You want to be afraid 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 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 yeah exactly he has less time than you to scrutinize no way less yeah and he said the only thing he looks for is the determinism how is this person going to do this no matter what and all of his questions 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 got over why are you doing it like you know what if this comes up like what if someone offered you that 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 go to 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 round a world you're looking for somebody who will go to unreasonable lengths and i suppose this is why uh 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 a lot of these people live on the line yeah it's just it is what it is um when you said that i couldn't help but and i it's horrible the accident she had but i couldn't help but think of lindsey vaughn like she had a lindsey vaughn's a downhill skier that's 41 42 and is in the olympics right now okay and um you know she had retired a while back and came back trained again was her And 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. Went to the hospitals, had three surgeries. It's not for sure. Yeah. But to be in your 40s and coming back somewhat injured. and i'm like i'm going i'm sending it anyway look i i i didn't know about this story um this just happened like a week ago i kind of like it i kind of like it you want 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 40 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 or maybe he does if he's paid well but i'm sure her physio and her strength and coaching coach don't like it yeah um 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. 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 capitalist that's been through one of those pivots, they're famously known as pivots now. It's all about the person. 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 hires a 50-50 bet at best. So why, if you're doing positive, like trying to run MPVs, would you even take the 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 product thing is just more artistic. Sounds like a taste again. Yes, more like a movie than business. I love that idea. And business products are more systematic. You can algorithm that down to Steve Jobs once said that the difference is the buyer in a business isn't the user. And he made that point. And that may be it. Like that may be the essence of it. That's cool. I am this thing that 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 founded. and um one of the interesting elements that i've seen with this where we we did a raise last year we raised 3.44 million dollars and right now we're in the middle of raising six and a bit uh 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, fucking forever away, drove to Leeds for one investor meeting to 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 uh a couple of times sent the deck out this was in the first one so we send this deck out and it's all sexy and it's got 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 familiar with this on the left hand side is sort of a neanderthal guy and on the right hand side is a sage that looks like a jedi in the middle is a guy that over complicates everything and he's sort of screaming and getting. The joke is that the guy on the left and the guy on 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 and pre-digested way is consumed within 30 minutes. 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 on the left and the guy on the right said, I bet on Chris. yeah i bet on chris i bet on chris yeah 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-founders do 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 i've 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 gotta 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 and i in 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 enough for them no no no i don't i don't disagree i'm not advising people people are prepared if you want fucking investing in newtonic please scrutinize but i want to say one other thing about this because i think it gets more to the point of of what you said um most people perceive venture capitalists to be making investments the way maybe a buy-side public investor might be. If it's positive IRR 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 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 taps in it's it's about chris for sure yep but there's they also need to kind of love the category and love the idea and want to spend 10 years working on the problem like all those things like it means it they have to flip from zero to one in their own head yeah 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 it but but you know i'm not 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, 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, Bert Bevers, the guy behind Tito's, yeah, yeah, yeah. 100% of his. Unbelievable. Do you know Gymshark? Are you familiar with Gymshark? 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. 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 acquisition than want to do a half a billion acquisition. What's the size of the market you're selling it to? 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. Fewer people that can buy it. It's going to have more scrutiny that goes over the top of it. You've now diluted down. You need audited financials. You need like they're going to have to file an essay. There's all this stuff. It gets really hard to sell a company. 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. It matters. It really matters. It really matters. 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. 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 term 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 raise $500 million, Common doesn't even participate until you get a sale over that, technically. Now, 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 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 see i i was like i am not in fact i gained i gained share of newtonic when we did the raise so i bought in a over the top of where i was already while we were diluting down it's hard to do it was i mean james james what i did new portia um and he was very gracious and we shifted some stuff around and i can't remember where else i took that's awesome but no it was it was cool and um it's been really fun sort of learning about that world and now it being able to see what's happening especially in the world of ai at the moment oh that's a question what what are you most excited about with regards to the industry of AI and what do you think is overblown I would I mean 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 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 guys, the guy in Naked and Afraid, like I'm going to be more involved than him. I can do more stuff. And this is the latest of those things. And anyone that is a skeptic, and I've met a lot of like the top academicians that are skeptics and all this, you are 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 hone your 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 you look 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 i find i mean i haven't i i i'm anxious this why also why i was a a useful i use the word useful venture capitalist 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 i and uh you're allergic to ignorance yeah i'm coming off of it a bit because i haven't done a claw bot yet which i feel guilty about oh you can't get it 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. 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 a 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 of a 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, you know, almost done wrapping up, feeling good, and the editor says, Bill, take a shot at the conclusion this weekend. So I spent six hours, seven hours. I sent him something. He's like, this sucks. It was really the first critical. He didn't use that phrase. I really don't like this. So I asked ChatGPT in the pro version, the 200, 300 hours 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. What was the idea? I'll give this one away. The concluding chapter's title, 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 gotta struggle you gotta suffer you gotta be okay with failure in praise of the grind yes and the editor loved it good i think that's i think that's an important message yeah so i 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 um when it Because 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 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 small rules it there's there's more freedom in actual language text than in coding 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 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 holders 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 an editor of translation. Right. And that's an opportunity to move upstream, be the 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. 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 janky. 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-type enterprise app historically did it. 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. 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. But the book, people talk about this generalist versus specialist and this comparing of 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 I'd always heard a phrase called for 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 generalist. Yeah, yeah. And they're able to bring patterns 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 and 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 there it's it's more noisy you're wading through like it's harder less aligned right yeah yeah but the insights are power loss step changes it'd be like you like listening to someone talk about um great writing technique and get an idea for the podcast you know well 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 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 1000 was me recreating the house from interstellar on a 85 foot video wall the 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 it 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 the house from 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 and the Mac. It may or may not. 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 does that what is that just cool for them to 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 uh ai can't replicate uh 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 like it's not going to build a friendship with this other person that i that i want to hang out with i agree with that it can't choose is this the right guess and you 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 um but that also doesn't account that's a local maxima which is everybody's got the opportunity to operate for that yeah to optimize for that whereas if you're trying to refine for the taste i agree different i can bill gurley 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 you're 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 uh it's good where should people go to check out everything you're doing um so so i've historically spent most time we were an investor in twitter early on so i've developed my x 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. I feel like such a neophyte. In Twitter, I get everything. I understand it. Instagram is a different language. Yeah, it's a different language. I'm figuring it out. Heck yeah. Bill, I appreciate you. Thank you, sir. Bye.