00:00:00What got you into thinking about the idea of career regret?
00:00:04As somebody that's had a very seemingly successful and fun career, why did you think about it?
00:00:09I 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.
00:00:18And through that process, I started writing as a way to differentiate myself.
00:00:23And so I was an early blogger, it was actually a fax, that's how old I am, when I started.
00:00:29And I got in the habit of when I had ideas, jotting them down.
00:00:34And then either developing them, a lot of them ended up just undeveloped, but if I developed them they would become a blog post.
00:00:42And there was a period in my career where I was reading a ton of biographies.
00:00:46And 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.
00:00:55And that thing kind of simmered and breathed and took on a little bit of a life.
00:01:00And I got asked by the dean of the business school here in Austin at the University of Texas to talk to the MBA class one day.
00:01:08And I was like, "Can I do this?"
00:01:10And he said, "Sure," so I pulled it out and developed it a little bit as a PowerPoint presentation.
00:01:15Anyway, they posted that on YouTube, a few people noticed, some people that have been on your show, James Clear, noticed.
00:01:23And he posted it on his website, and people started prodding me to develop it as a book.
00:01:28And a few years ago, I decided to begin retirement as a venture capitalist, it actually takes a while, unfortunately.
00:01:36And 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.
00:01:43A 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.
00:01:51And 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.
00:02:01And I was drawn to that at this moment in my life, I was drawn to this particular thing.
00:02:06So I spent like six years working with a co-writer and researcher, developing it further and making it this way.
00:02:14But you used the word regret.
00:02:16We did, along the way, I launched a survey on Survey Monkey that said, "If you could go back and start over, would you do a different career?"
00:02:26And seven out of ten people said yes.
00:02:29And I eventually took that to work in people analytics, and they did a more scientific version of it, a much broader audience, and came back six out of ten, but very similar.
00:02:39And that notion of career regret's interesting, I had the opportunity to talk to Daniel Pink, who you may know, who wrote a book—
00:02:47He's been on the show about regret.
00:02:48About regret.
00:02:49Yep.
00:02:49And 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 end of life, are regrets of inaction.
00:03:02He calls them boldness regrets, it's what you didn't do.
00:03:05Humans 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.
00:03:14And so I've thought about this long and hard now since I've been working on it for six years.
00:03:20I fear our current education path has become a bit of a conveyor belt.
00:03:26We'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.
00:03:40And I think they're learning to grind.
00:03:44That's what Angela Duckworth's been saying.
00:03:46Now, the perseverance part, we've taught them, but if they don't have the love for it, it turns into burnout.
00:03:53And 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.
00:04:03And 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.
00:04:17I think the people that do that are the people – you know these people that just love what they do.
00:04:24And not only are they more successful, but I think they radiate a bit and spread positive energy.
00:04:30Well, they're mimetic as well.
00:04:32They become a role model for other people to go and do.
00:04:34Oh, he took a chance on that thing that he wanted to do, and wow, it didn't work out.
00:04:39And his life didn't blow up, or it did work out, and he's really happy.
00:04:42That's right.
00:04:43Thinking about the fact that we seem to regret inaction, boldness, regret.
00:04:49Yeah.
00:04:49Have you reflected on why you think that is, what it is in the human mind that causes us to prefer decisiveness over –
00:04:59I 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.
00:05:11Our brains constantly are replaying things in our minds, and maybe that's what dreaming is, too.
00:05:22But 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.
00:05:33And then you compare that to your current life, and unfortunately that can create anxiety, but I do think that might be part of it.
00:05:41You'll be familiar with the Zeigarnik effect.
00:05:43I'm not. Tell me.
00:05:44Oh, cool.
00:05:45So 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.
00:05:57You know, you've ever been to a restaurant, and you see some waiter come up, and they're stood, no pen, no pad, no iPad, hands behind their back.
00:06:06And they go, "This guy's crazy. He's insane. I'm definitely going to get something wrong."
00:06:10And 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 pad."
00:06:21And the study ended up finding out the Zeigarnik effect, which is an open-loop, closed-loop bias that exists inside of the human mind.
00:06:33While the tables were still open, the servers were able to recall what the orders were very closely.
00:06:38And as soon as they went, nothing at all.
00:06:43You 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.
00:06:50Let's say that you're moving from city to city to city.
00:06:53You're not bad at remembering the hotel room of where you are now.
00:06:56Yeah.
00:06:56But if I was to say, "Which hotel room did you stay in two hotels ago," all right, 735 -- I have no idea.
00:07:03It's the same reason why cliffhangers work at the end of TV shows to get you to watch the next one.
00:07:10Yes.
00:07:11The open-loop -- the human mind abhors an open-loop.
00:07:14Yeah.
00:07:14And I get the sense that --
00:07:17I see what you're saying.
00:07:18-- when it comes to boldness, regret, the main thing that you have is an open-loop.
00:07:23Yeah.
00:07:23Now, the human mind abhors open-loops and uncertainty and ambiguity so much that we'd rather imagine a catastrophe than deal with the uncertainty.
00:07:35That's what a lot of anxiety, sort of future projected regret kind of is, right?
00:07:39I 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.
00:07:45And this is the same thing, I think, in some regards, but in reverse.
00:07:49What could have happened?
00:07:50Yeah.
00:07:51What could I have done?
00:07:51And there's an interesting way to flip it on its head.
00:07:54When 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.
00:08:06And 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.
00:08:15And he just imagined he's 80 years old and was trying to get advice from his 80-year-old self about what to do.
00:08:23So he put himself in that future place where he might have that boldness regret.
00:08:28And 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.
00:08:40And in both of those cases, a couple of years in, I paused and reflected, and I only thought about this as I've been promoting the book.
00:08:52I paused and reflected, do I want to do this for 30 years, and was able to fast-forward that in my brain, and I was unhappy with that reflection, which encouraged me to think about what's next.
00:09:09When 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, but it is a really wonderful idea.
00:09:23And I guess Jeff's got other stuff that he can be well known for, so perhaps, you know.
00:09:29Well, it's actually quite synonymous with one of the seven habits of highly effective people begin with the end in mind.
00:09:38It has a similar kind of --
00:09:40When looking at the regret minimization framework, what are the things that -- what are the common pitfalls that you've seen people do, even both inside of their career and outside of it?
00:09:53You must have reflected on this a lot.
00:09:54Yeah, I have. One thing that I think, especially 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, Jonathan Haidt called it a resumé arms race, we've built 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.
00:10:23And they feel like tweaking any way away from that is throwing away the investment. Does that make sense?
00:10:32Like a loss aversion type thing?
00:10:34Yes, 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 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.
00:11:00And 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.
00:11:10And when I mention this to young people, there is this weight, there is this weight they feel, like an obligation to, especially...
00:11:21Decisions that they're locked in when they were 17.
00:11:23Yes, well, and that's another thing. 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.
00:11:35So 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.
00:11:44Like that's, you know, three years forward and less time to... There's a lot of people, a lot of smart people that just say we don't allow children enough time to explore.
00:11:58And, you know, Hite says it. He has a chapter called Let the Awesome Play or something. Rick Rubin's been pounding on this. He talks about it in his...
00:12:09We looked at Gene Twenge's work, Generations.
00:12:12Is that another one?
00:12:13Yeah, Generations is really fascinating. This stinks of you. Highly recommend it.
00:12:17Okay, I will.
00:12:18And she talks about extended adolescence, sort of twins with some of Hite'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.
00:12:35We 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.
00:12:44And then at the same time, kids are moving out of the house later, they're getting their driver's licenses later, they're getting employment later, they're getting into relationships at lower rates, less alcohol, less casual.
00:12:55All 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.
00:13:08They're socially very immature, professionally expedited.
00:13:12And he ties them together?
00:13:14Gene Twenge, yeah, for sure. I think that...
00:13:17Oh, actually, no, no, no, no, no.
00:13:19Great point. And I don't know. And I don't think so.
00:13:23Now, there might be some rebellion going on.
00:13:26Like, "Oh, God, everything just feels like I need to get my act together. How can I do these other things that just so much of my cognitive real estate is taken up?"
00:13:36I could see that.
00:13:37Maybe that would be compensatory.
00:13:38Yeah. Like I mentioned, I think when... about 10 years after Duckworth wrote Grit, she said that she wished...
00:13:49she positioned it as 50/50 passion and perseverance, and if she could do it again, she'd put more on the passion because she thinks we taught a whole generation of the high performer children how to grind.
00:14:02Like, we taught them to persevere, which is...
00:14:05Well, and so I get that.
00:14:08Grit was a massive book.
00:14:10I don't think that she should lay at the feet of her pen the issues of this stuff.
00:14:16But I think one of the reasons why, from a personal development standpoint, it's a bit more seductive to over-index on the perseverance than the passion is that passion feels more difficult to engineer.
00:14:26Fair enough.
00:14:27So, "Oh, how do I get the thing, the line, the stuff?" It feels a bit more egalitarian to say, "No matter what it is you're doing, if you hold hard enough, you can get things."
00:14:39I do think it is the hardest question.
00:14:41What is?
00:14:42Finding it. Finding it and knowing it. Knowing it's a little easier, but finding it.
00:14:47There 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."
00:14:57Because it's the truth. They don't know.
00:14:59But I think that's okay. It's just we shouldn't force the question upon.
00:15:04You've got this line, "Life is a use it or lose it proposition."
00:15:08Yeah.
00:15:09What's that mean?
00:15:10It's tied to the boldness regret, right? Like you're going to get to the end and then it's done.
00:15:17And 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.
00:15:30The recognition that life moves much faster than any of us realize and then it's done.
00:15:38And you can get locked in even sooner. If you spend up to your limits, you can freeze yourself in a job that you can't leave.
00:15:48And you can do it with personal commitments as well.
00:15:51My second career was going to Wall Street.
00:15:55And I can't tell you the number of people I worked in with Wall Street that had, for their age, ridiculously high salaries.
00:16:03But they had the place in the Hamptons, the summer lease. They tried to get into the membership club.
00:16:08They spent right up to the limit. And now you can't switch. You can't switch.
00:16:14You're locked in at this very high burn rate, which means you need to keep pouring fuel in the top of it.
00:16:19Yes. 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.
00:16:33Move cities, change jobs, all of which may be the right path for them.
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00:17:39Yeah, it's weird isn't it? Because flexibility is actually a really difficult thing to show off. Even flexibility is only showoffable 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.
00:18:04So I've always thought about this, the difference between hidden and observable metrics will often trade a hidden metric for an observable one, trade the quality of our sleep for a slightly bigger pay packet, will trade the hours of peace that we have on a Saturday for position improvement.
00:18:27Some people will trade a caring supportive wife for a very difficult younger hot one. The trades are everywhere.
00:18:37Yes, I think that's a good framing.
00:19:06I guess what I would say is I have an immense amount of respect for someone who adopts that mindset, the one you described, especially if they're really thriving in something that they may not perceive to be an occupation. That could be a religious community, it could be volunteer work that they do.
00:19:28I would highlight to them there might be a career in that 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.
00:19:42If they're happy and passionate about that lifestyle, that's great. I'm not casting any shadow on that whatsoever. If you are the type of person that is either unhappy with your work, so much so that it's impacting your quality of life.
00:20:02Or 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.
00:20:16That's who I really, really want to read my book. There's a great story. There's a couple of these actually, but I'll choose the Steve Harvey one. I don't know if you've seen this, but you know who Steve Harvey is, the comedian who does the family feud now?
00:20:33Yep. He tells this story, I think he told it on Oprah, that when he was seven, the teacher asked them as an exercise to write down a sheet of paper what they wanted to be when they grew up.
00:20:46And 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."
00:21:03And she thought he was 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.
00:21:16So 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."
00:21:34And you hear a story like that, and I don't think—there's a lot of people—I think that that's a very hard thing to do. I think that for parents, and I'm a parent of three and I've lived through this phase that we're talking about, your intuition as a parent, like in your DNA somewhere, is to look after the economic welfare of this child.
00:21:58You want them to live a good life, and it's very hard not to associate that mostly with money.
00:22:05And 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.
00:22:16And I hear a story—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." He said that was the last thing. He thought his dad was going to yell at him, and his dad kind of gave him this push.
00:22:32And that's what I want the book to do. 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.
00:22:45You 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?
00:23:01Yeah.
00:23:03So 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.
00:23:16Yeah.
00:23:17Why do some people successfully pivot and others end up getting stuck?
00:23:23Well, I mean, you could come up with a number of things. One of them is financial, which we talked about. You could be overspending. There's a different case where you're stuck financially, like you need your living hand to mouth.
00:23:37I 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, not only achieved, touched the top rail of that, but then launched beauty products, sold that company.
00:23:53But she moved to LA with $300 in her pocket. And that's not to say anyone can do that, but there are stories of people with near nothing starting on the very bottom rung and finding their way to be successful.
00:24:07There's this classic meme of starting in the mailroom in Hollywood, and David Geffen and Barry Diller, all these people started in the mailroom. It's about as low a rung as you have in that business.
00:24:21So I think it's possible, but you may feel stuck financially. You may feel that you can't get there. And then the other one, it could be like this perception, McConaughey had this perception that his father wanted him to be a lawyer.
00:24:36It's probably just that Matthew had told him he was going to be a lawyer and he was supporting that, but that weight can be there too. You may feel, I think there are certain cultures where being a doctor is considered really, in Russia, being an academic.
00:24:57So 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 kinds of things that could restrict this movement.
00:25:10What about the fear? There has to be a huge chunk of people that just, what if this doesn't work? It's sort of ambient, ephemeral, this few fog thing that's come down on them.
00:25:25If you allow me to give you a little history of how, or why I would say, I spent six years turning the original presentation into a book.
00:25:35And 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 Housley on.
00:25:47He's the GOAT. He's the absolute GOAT.
00:25:49And he was on a podcast called Why We Write, talking about 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.
00:26:05And so every other chapter is an Atlantic-sized article about someone that started on the bottom rung with intention and made it to the top.
00:26:15And 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.
00:26:25A lot of the books in the category that have done extremely well in career read like a textbook. Do A, do B, then do C.
00:26:34But 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?
00:26:42It's 100% correct. I mean, Ben Shapiro's famous line of facts don't care about your feelings is as backward as it could be, that feelings don't give a single fuck about the fact.
00:26:52Yeah, so we have eight, nine, or ten, I should know the exact number, but I can't recall right now, of these profiles.
00:26:58And I alternated them with the principles. And I always thought about it like candy and vegetables, you know, or something. But you get some of both.
00:27:07It brings the ideas to life.
00:27:09Yes. And I think the reason I told that long story was an answer to your question about fear. I think seeing this many stories, and they're all -- by the way, I chose every one of them from a field that your parents would probably tell you not to go into.
00:27:26I intentionally skipped, you know, investment bankers and --
00:27:30Doctors.
00:27:31Yeah, all the stuff that everyone knows is --
00:27:34Nice linear progression.
00:27:35Yes, 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.
00:27:49I hope it works.
00:27:51Me 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.
00:28:02Yeah.
00:28:03Pithy 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.
00:28:16Yes.
00:28:17I 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.
00:28:35The 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 onto.
00:28:41Yeah.
00:28:42But if you give somebody a story, how are you going to forget that?
00:28:45Years ago -- and I don't know when it started. Actually, it's funny. I just said I don't know where it started and then something popped in my brain. I fell in love with these long-form nonfiction articles. There's a website called Long Reads.
00:28:57Okay.
00:28:58It 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 Times Magazine when I was -- it was in '93 or '94, and it was 20 pages. That may have been the first one that got me into this.
00:29:22But 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 being beat writers on newspapers and started doing this longer-form journalism and how it brought stories to life.
00:29:41I think Truman Capote's highlighted in that. Tom Wolfe put together the first one. And then the second one has Krakauer and Lewis and all the modern --
00:29:52Well, now we've seen this pivot into Substack, right, that 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 looped back on yourself enough, and you end up in charge of CBS, Matt Taibbi, and you end up in charge of the Twitter files or whatever.
00:30:12I'm a huge Barry fan.
00:30:14So talk to me about the risk of starting over in your 30s or 40s.
00:30:19Yeah.
00:30:20The idea of not just what am I going to do, but I should have had my life together by now. 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.
00:30:35What are people going to think of me? What's the real risk of starting again in 30s and 40s?
00:30:40Well, one thing I would encourage you to do -- there was this book I read when I was really -- I think back in business school called Shark Proof by Harvey McKay. He's known for his sales book, but he wrote a book about careers. And he said to keep your dream job -- this was an older book, so he said keep it in a manila folder in a file, but you could create it in a Google Doc or something.
00:31:01Where you're just keeping notes. Like, well, if I do it one day, 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.
00:31:16You can begin the process before you make the leap. 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.
00:31:34You 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 learned about stocks, and I was trading stocks.
00:31:50You 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. That's what I was doing in my spare time. So if you're doing something like that in your spare time, it's calling you.
00:32:07And 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.
00:32:27But 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.
00:32:41And the boom-bust cycle. Became a mortgage broker. Didn't really love it. Not sure he equated his identity to being a mortgage broker. And one night -- this is such a -- it's part of why I love self-help books and ideas so much.
00:33:00He'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."
00:33:13And he's looking at this sheet of paper and realizes he wants to start a spirit company. He's got chemistry on the right, hanging out at bars on the left.
00:33:25And 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 Texas.
00:33:39But of course, Tito's is now the most best-selling spirit in North America. He owns 100% of it himself.
00:33:48No way. The whole thing's bootstrapped?
00:33:50Yes, credit card. Yeah, 19 credit cards. But it's such a great story. Like, it's just such a great story.
00:33:58And now, you know, he's at the phase in his life where he's giving back and launching foundations.
00:34:05And this is my point. Like, I had a young person at Johns Hopkins raise their hand and say, "But I don't want to chase my passion. I want to be purpose-driven."
00:34:14And I thought to myself, you know, every profile in the book, these people are touching more lives than they could have ever imagined.
00:34:23I don't want to chase my passion. I want to be purpose-driven.
00:34:27I think it's part of a new movement to just, like, feel good about yourself. Like, my main goal in life is to help other people.
00:34:35Serve. Okay, that's interesting. Well, it's noble on the surface.
00:34:41And there's certainly some things, you know, in the same way, this person has a high burn rate, family to support.
00:34:48You don't have the luxury in quite the same way. This person -- there are some jobs that just suck.
00:34:55There are some jobs -- you're serving your country. You know, I'm sure lots of people love street cleaning.
00:35:01But I would imagine that some people do it more out of a sense of service than they do out of a sense of passion.
00:35:07My 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.
00:35:17They're serving in a much more seamless way that's leveraged as well.
00:35:21Yeah. I mean, one of my favorites on that front is, many years ago, because I was involved with Open Table,
00:35:29I met Danny Meyer, 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.
00:35:39But 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.
00:35:50Like, it's on their resume. They talk about it all the time.
00:35:53Like, there's almost this church of Danny Meyer, like, for everyone that rolled through it.
00:35:58That's got to just feel amazing.
00:36:01What is it about his demeanor or culture or ethos?
00:36:04The book talks about this kind of understated sensibility to his book, to hospitality.
00:36:13Like, 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.
00:36:26But his journey is about more than that. That's what his book's about.
00:36:30His journey is about being hyper-curious and an excessive learner.
00:36:38Like, every single step along the way, including today, he's still doing it.
00:36:44You know, last time I talked to him, he just got back from Europe. He'd taken all his chefs on a tour of Europe together.
00:36:50Jotting notes, learning, like, just constant learning.
00:36:55That's so cool.
00:36:56Which I think is, that's the second principle in my book, is continuous learning, but it ties in with the first one.
00:37:04The best test as to whether you've found your passion is, does the learning feel like free?
00:37:10Like, would you do it instead of watching a TV show?
00:37:12Like, is it something you enjoy so much that continuous learning is just you enjoying life, you know?
00:37:22And if you find that, you found it. You found your passion.
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00:38:42Joe Hudson's got this line, "Enjoyment is efficiency," he says. I think it's really, really true.
00:38:50People have this relationship between discipline, motivation, and obsession.
00:38:56Discipline's always there, but there's a lot of friction.
00:38:59Motivation, the friction gets removed a little bit, but it's sort of harder to grab ahold of.
00:39:04You don't really know where it comes from. Maybe it's a rock playlist or maybe it's the right amount of caffeine or something.
00:39:08And obsession is friction inverted as opposed to you having to push through resistance.
00:39:14The resistance pulls you toward it.
00:39:16That's exactly right.
00:39:17And the problem, I think, or the reason that obsession is difficult is that obviously if it's pointed in a non-positive direction, that's how you become obsessed with politics or porn or your toxic ex or something.
00:39:30But if it's pointed in the right direction, what from the outside looks like a superhuman amount of discipline.
00:39:36From the inside, feels almost like you haven't chosen it.
00:39:41I'm not choosing to do this thing.
00:39:44I 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.
00:39:55My house back in the UK has got a podcast studio on it.
00:39:57The one that I live in right now is still podcast eight years in, a thousand episodes.
00:40:02Every single house has had one, every Airbnb that I've stayed in, I get there and I'm like, fuck.
00:40:07I'm researching hotels to see if the depth of the table can withstand my MacBook, the stand, and the fucking tripod.
00:40:14Because that's what I want to do.
00:40:17That's what I want to do.
00:40:18I want to have these conversations.
00:40:19So, okay, my entire life gets warped around it.
00:40:22I'm sure you'd be familiar with the single-ordinating principle.
00:40:25I think Bezos has got one and I think Musk's got one.
00:40:28And Bezos' was always, does this make the customer experience better?
00:40:33So everything, every single decision in Amazon was threaded through this sort of single eye needle.
00:40:40And Musk says, does this get us closer to Mars?
00:40:44Does this get us closer?
00:40:45And by the way, both of those people did something that is super extraordinary, which is they took an innovative company,
00:40:55grew it to hundreds of thousands of employees, and kept it innovative.
00:40:59It's two of the only examples I know of.
00:41:02They didn't get laden down with diseconomies of communication, lumbering fucking behemoth bullshit.
00:41:08The bureaucracy that always lands in big companies.
00:41:11And it must be some heuristic, like the one you described, that allows the, in fact, I was just listening to Elon on Cheeky Pine, I think.
00:41:22There's Dwarkash.
00:41:23Yeah, this came up.
00:41:24This came up.
00:41:25Like, every leader wants to know how he does it.
00:41:28That's why I think Collison was asking him, like, how do you lead?
00:41:33He goes, well, I'm down deep.
00:41:35You can't be deep.
00:41:36There's 200,000 employees.
00:41:38And Elon jokes, yeah, there's 200,000 employees.
00:41:40Like, you have to have some heuristic, simplifying heuristic that can spread through their brain.
00:41:48Or else it's spinning too many plates.
00:41:49Yeah, exactly.
00:41:50Yeah, yeah.
00:41:51It's pretty impressive.
00:41:52It's super impressive.
00:41:53Okay, so career pivot fear.
00:41:57Yes.
00:41:58Someone is in the career, not super fired up.
00:42:02I used to be, and it just feels like it's time for me to grow now.
00:42:07What are the indicators that it's time to move?
00:42:12And what are the things that they should keep in mind to maximize their bravery?
00:42:19Give them a little exogenous amount of morale.
00:42:22So on the do you know, I mean, I love this test of do you see yourself doing this 30 years
00:42:30from now?
00:42:31Because if the answer to that is no, you should get busy.
00:42:34What's the line from Shawshank, get busy living or get busy dying?
00:42:37Like, if you know that's true, like, well, now is when you should start.
00:42:42I'm not saying like quit tomorrow, but like start building the plan.
00:42:46Like, and then there's all kinds of things you can do in designing your life.
00:42:52Dave Evans says, has this exercise where he says create three to five scenarios in battle
00:42:58corner of what you might do next.
00:43:00Like, you know, fill them out.
00:43:02AI can really help, right?
00:43:03Like, like you could build a 20 pager on each one of these career paths.
00:43:06What might I like?
00:43:07What might I not like?
00:43:08What are the three things people love in this career?
00:43:10What are the three things you can steer it at all, right?
00:43:12You can ask people in those fields, you can go find them.
00:43:15So you could, you could role play being in each of these.
00:43:19There's a, there's a, there's a heuristic in the book that I borrowed from, from Ben Gilbert
00:43:25had acquired a lot of podcaster, um, where he had side hustles at all his jobs.
00:43:32So at each job he went to, he would ask the employer, if I do it on my own time, can I
00:43:38do this other thing also?
00:43:40And what's, there's something really great about that.
00:43:43And in each of his cases, he ended up doing something pretty remarkable in the side hustle
00:43:48at Microsoft.
00:43:49He created Microsoft garage, which became this way for Microsoft to stay relevant with founders.
00:43:54And he met all these founders, like all this kind of extra goodies came from that.
00:43:59Um, but I think it all, like, so you learn more, you learn maybe two, you get two shots
00:44:05on goal instead of one.
00:44:06And I think the employer makes you look proactive.
00:44:10So it reflects positively on you.
00:44:12When he ended up at, at Madrona VC asked him if he could start a podcast and look for that
00:44:17lead.
00:44:18And, um, I just had dinner with the both of them and, uh, they were in Austin and man,
00:44:24they're happy.
00:44:25Like I got to tell you, like they are really happy people.
00:44:28So similar to you and, and, uh, your obsession and, and they fell into it through that, through
00:44:35getting there through that way.
00:44:36So I think those are some things you can do to, uh, to test and then look, what are you
00:44:43doing in your spare time?
00:44:44Like, are there any signals there?
00:44:46Um, those are all great ways.
00:44:48I wouldn't quit if you don't know where you're going.
00:44:50That doesn't make any sense.
00:44:51Yeah.
00:44:52Yeah.
00:44:53It's such a good shout to say, sort of, what are you thinking about in the shower?
00:44:56Yes.
00:44:57What are you doing in your spare time?
00:44:59I keep on fucking watching pickleball drills.
00:45:03I just keep on thinking about pickleball and I'm really interested in the sport and I'm
00:45:07interested in how it's growing and I love playing with my friends.
00:45:09But even when I'm not playing it, I'm always thinking about it a lot.
00:45:12Maybe this is, you know, maybe there's something going on.
00:45:15Let me share this fun story I just stumbled on.
00:45:17Cause I was, I was, I'm using some hacker techniques to promote the book and that led me to talk
00:45:24to this gentleman.
00:45:25And, uh, I, when I pinged him, he said, he said, Oh, please send me the book.
00:45:31He goes, I saw the video a long time ago and it changed my life.
00:45:34And I said, well, tell me that story.
00:45:36And, um, he was, he was a real estate lawyer and he loved football and he loved offensive
00:45:44plays and offensive diagrams in football.
00:45:47I love this story cause it fits with my thesis that the best stories are in jobs your parents
00:45:52would tell you to never go do.
00:45:54He launches a website to help people like manage and develop football plays.
00:46:01And then he builds software and then he starts a podcast.
00:46:04He has 900,000 followers and this is what he does all day.
00:46:08Now he talks about offensive football plays with the best and the brightest in the field.
00:46:14He's known throughout the industry.
00:46:16What a great story.
00:46:17Like how awesome is that?
00:46:18That's brilliant.
00:46:19It's so great.
00:46:20Like, like I think people don't realize that you can actually, there are careers in a lot
00:46:26of places.
00:46:27A lot of people, um, want to be in Hollywood or music and they think they can't do it because
00:46:33they're not talented, but there's a hundred support jobs for every artist that's out there
00:46:39and there's tons of work to go do.
00:46:42You know, if you really love being around that stuff, there's tons of opportunity.
00:46:46Well, especially given that you can fail at a job that you hate, you can, you can underperform
00:46:53in an industry that you don't want to be in.
00:46:56So the prospect of potentially doing okay at one that you love is infinitely better.
00:47:02I think so.
00:47:03I think so.
00:47:04That goes back to life is a use it or lose it proposition.
00:47:08Like give it a go.
00:47:09And then the other thing to know about failing in that is, uh, humans are like this, the,
00:47:16the research in psychology says humans are really good at forgiving themselves.
00:47:19Like you're not, the failure is not gonna, you're not going to ruminate on it forever.
00:47:25Especially if you tell yourself, well, I'm proud of the bravery to make the call.
00:47:30No doubt.
00:47:31Isn't there some evidence from psychology that humans prefer just making decisions generally,
00:47:37that if you make a decision, you tend to be happier.
00:47:39Someone's let's say it's a, maybe a slightly less momentous decision between one city and
00:47:46another, uh, or the city that you're in now are moving.
00:47:50Um, on average, people that move are happier.
00:47:52And I think part of that is just, well, life is like novelty and variety are pretty fun.
00:47:59It's different and no doubt exciting.
00:48:01And even if it's objectively a little worse, subjectively, it's all new.
00:48:06Yes.
00:48:07I liked it.
00:48:08I liked it.
00:48:09I just had a similar life experience.
00:48:11I spent 25 years in the Bay area, uh, living in one type of community.
00:48:15And when I moved to Austin, I moved downtown in a high rise, completely different repot.
00:48:20And it's invigorating.
00:48:22Like it's awesome.
00:48:23New place for coffee, new place to work, take your calls, your morning walk.
00:48:27All that's different.
00:48:28That's great.
00:48:29I agree with that sentiment.
00:48:30So you quit a successful job at Compaq.
00:48:33Yep.
00:48:34To start again.
00:48:35Yep.
00:48:36How do people know when they're plateauing versus they're just a bit bored or something?
00:48:43Yeah.
00:48:44Um, I, a few people have asked me this question.
00:48:47I, once again, I think the 30 year forward exercise gets you away from that because it's,
00:48:53it's, it's asking a different question.
00:48:56Um, one, one thing I'm really big on is, um, and there's a, there's a different chapter
00:49:04dedicated to this is, is developing peer relationships.
00:49:08And we can go into why I think that's such a huge unlock, but, but one of the benefits
00:49:13of having a group of peers, especially if they're outside your organization.
00:49:17So these are people on the same career path you're on, but, or maybe a bit distant, they're
00:49:23at a different company or whatever.
00:49:25And if you have a community like that, that you really trust and support one another, they
00:49:30can help you with that question you just asked.
00:49:33Like, am I, am I failing and I'm never going to succeed because I don't have the right
00:49:38talent for it?
00:49:39Am I, do I maybe have a shitty boss?
00:49:41Is their experience different?
00:49:43Like, like you can, it's a great group of people to ask those questions of.
00:49:48It's almost like being able to run a little split test of yourself.
00:49:51Yes.
00:49:52What are the things that are different in your experience and how much of those are fundamental
00:49:58to the role?
00:50:00Exactly.
00:50:01Yeah.
00:50:02Absolutely.
00:50:03There's 10 other reasons why you should build that group, but that's, it's good at helping
00:50:09with that problem that you just described.
00:50:11How do you deliberately upgrade your peer group without it being transactional?
00:50:17How can you make like-minded friends and peers without them thinking that you're constantly
00:50:24just wanting something?
00:50:25Yeah, it's a tough question because I think the number one reason people are bad at forming
00:50:30these peer groups is they've been taught to be a climber and they've been taught to, almost
00:50:38been taught to be a bit sharp elbowed and to outgun the next person.
00:50:42Zero summing.
00:50:43Yeah.
00:50:44And we borrow a lot of our mental frameworks from finite games that have a beginning and
00:50:50an end and a single winner.
00:50:51And careers just aren't that way.
00:50:53Almost any industry, if it's not downhill skiing, there's lots of winners.
00:50:58There's tons of winners.
00:51:00Podcasting is a great example of that.
00:51:02There's tons of winners in Austin.
00:51:04And so if you can build a peer network of like-minded people that you trust, and the great test of
00:51:16do you trust, would you share your best ideas with them?
00:51:19Like that you've learned this new thing that you just unlocked in your job, would you share
00:51:23it with them?
00:51:24You should actually, I believe, but a lot of people wouldn't.
00:51:27And so once you get to that place, it's a really special place.
00:51:33There's a story in the book about Chris Del Conte, who's the athletic director here at
00:51:38the University of Texas.
00:51:40And when he broke into sports administration, he was in the development office, he went
00:51:45to a conference.
00:51:46And it's a great place to meet peers.
00:51:49He went to a conference and met with a couple of other young men who were also at the beginning
00:51:55of their career.
00:51:56They exchanged numbers and started a text group.
00:51:58And over time, they added a few more people to that.
00:52:01It got up to like seven, seven or eight.
00:52:04All eight of them are D1 athletic directors now.
00:52:09And they all started on the bottom.
00:52:11And if you follow them along that journey, their learning elevated each time.
00:52:17Each year they met, each time they texted the problems, they were encountering, they were
00:52:22sharing, they were explaining.
00:52:24It got to the point where they would do weekends away with their wives and invite in guests.
00:52:30You know, you talk about external learning.
00:52:32Who's holding many conferences on their own nickel and bringing in external guests to help
00:52:40educate them so that they could rise and thrive together?
00:52:44There's another story that's perhaps more modern for the younger crowd.
00:52:53Mr. Beast did this when he was 17.
00:52:55He found three other people that were trying to hack YouTube.
00:52:59They were basically trying to figure out the game of YouTube.
00:53:02And they were on a Skype call for 16 hours a day together.
00:53:05And he says if there were a fifth person in that room, they would have made a million dollars also.
00:53:10Like it was just because the stuff they were uncovering was so usable and just deterministic,
00:53:17just no one else knew it.
00:53:19And he used a phrase I love.
00:53:21He said, "You know how they talk about 10,000 hours," referring to the Malcolm Gladwell book.
00:53:25He says, "We got 40,000 hours because we were sharing it all."
00:53:29That's not the exact math, but it's a cool reflection of the moment.
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00:54:48What do you think about mentors?
00:54:51Peers are great.
00:54:52They're struggling with the same challenges you're sharing and sort of going on the journey together.
00:54:56That feels cool.
00:54:57It's like a teammate.
00:54:58But presumably, there's a good argument to be made.
00:55:02Well, maybe you aim for someone that's already been through the pitfalls.
00:55:05Yeah.
00:55:06How do you come to think of the role of pitfalls?
00:55:08I think you do both.
00:55:09They serve very different purposes.
00:55:11The co-learning journey – I mean, peers give you co-learning, they give you support, which I talked about.
00:55:18They give you reflections.
00:55:20You can ask those questions.
00:55:22Is this the same in your job?
00:55:24You're vulnerable with peers.
00:55:27You wouldn't do that with a mentor, especially if you get the peer group in the right place.
00:55:32You tell them, "I'm struggling here."
00:55:34So, I think it's just a different purpose.
00:55:38I think mentors are extremely important, but I think the idyllic version of a mentor is a bit broken,
00:55:47because we encourage a lot of young people to cold call too high, where the rejection rate is going to be 98%.
00:55:54Because the CFO of this company doesn't want to be friends with you.
00:55:57Yeah, exactly.
00:55:58But it happens constantly.
00:56:00And so, what I encourage people to do is divide mentorship into two different categories. Have aspirational mentors.
00:56:08And just like that file folder for your dream job, create one for each of them.
00:56:13Like, study them like a kid might study Star Wars characters or something.
00:56:19You know what I'm saying?
00:56:20Like, really get enamored with these people that you idolize as aspirational mentors.
00:56:28And one, you're going to learn a lot studying them.
00:56:31And by the way, the resources are amazing right now.
00:56:34YouTube interviews, podcasts, like AI.
00:56:37You can learn faster than you ever could have learned before.
00:56:40So, study them.
00:56:42If you ever meet them one day, the fact that you studied them this long is going to prove super useful.
00:56:47And then, for the mentors you actually want guidance from, like, tone it down a bit.
00:56:52Like, go two levels below what you thought you were supposed to do.
00:56:55And 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.
00:57:10Like, the probability that you're going to get them to do the work is so much better.
00:57:15I noticed that when I first started the show in 2018.
00:57:18It's still not early, it felt late, but, you know, now it feels early-ish.
00:57:26It was so flattering for people to be invited on a podcast.
00:57:30You know, one of the other things, it's such a funny trick that I still use now, so the world can have this one.
00:57:37I realized that flattery was one of the big drivers, I think, for bringing people on the podcast.
00:57:45No one knows who it is, it's this random British guy asking you if you should come on.
00:57:49I always used to ask people, "Can you please put me in touch with whoever handles your podcast adverts?"
00:57:55And it's some small researcher at fucking University of Arizona.
00:58:02And they're like, "Oh, well, it's just me that handles my podcast."
00:58:07I'm seen in the echelons of those that would have an assistant or perhaps a receptionist that would handle my podcast ads.
00:58:13I get it.
00:58:14And that's still now. Please pass me on to whoever handles your podcast ads.
00:58:17And that's actually another good one, I think, just generally for any outreach to somebody.
00:58:21You want to be in front of the right person, and especially if you're starting to pitch up toward mentors.
00:58:26That right person who actually handles that thing might not be them.
00:58:30So, you know, reaching out, "Can you please put me in touch with whoever handles Bill's inquiries for coffee?"
00:58:38Or whatever it might be, to the admin inbox.
00:58:41Because the last thing that you want is some complex question that the person who handles the inbound open email thing or the LinkedIn DM requests.
00:58:50Is it them or is it going to be somebody else?
00:58:53Looking to get put in touch with the person who handles their partnerships or whatever it is.
00:58:57If it is them, they feel flattered.
00:58:58And if it's not them, the delegate person passes you on to the right department.
00:59:04And this isn't in the book, but if you ever meet the delegate person, pay as much attention to them as you possibly can.
00:59:14Just look through them.
00:59:16Oh, yeah. Learn all you can about them.
00:59:19Like, be generous and kind and thoughtful.
00:59:23It will pay off big time.
00:59:26Good story around that from the show.
00:59:29David Goggins. You familiar with David Goggins?
00:59:31I'm not.
00:59:32So he, ex-Navy Seal, endurance athlete, probably one of the most sought after podcast guests on the planet.
00:59:37In the last probably six years, he's done two podcasts.
00:59:42One of them was mine and the other was Rogan.
00:59:44Brought a brand new book out.
00:59:46His first book sold a gazillion copies.
00:59:48Brings a new book out.
00:59:50And for nine months, I'm back and forth with a person on his team.
00:59:57And checking in, seeing how everything's going, seeing the marketing, this, this, this, this, this.
01:00:01And then he cancelled every other podcast appearance except for Rogan.
01:00:06And they tried to cancel the one with me as well.
01:00:09And I got this message, really sorry, David's just going to have to, we're not going to be able to make it work.
01:00:15And I was like, look, I will do whatever it takes.
01:00:18I'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.
01:00:23And they said, a couple of days later, I got another reply, okay, we're in, we'll be able to make it work.
01:00:31And when I turned up, David, he's sort of stern, stern hard guy, comes up, very nice to meet you.
01:00:39The first thing he says after that is, I just want you to know the only reason that I'm here is because of her.
01:00:44And pointed to the person that I'd been emailing.
01:00:46Yep, precisely.
01:00:53So in your framework, loving the grind is sort of a non-negotiable.
01:00:58Can someone sort of learn to love grinding, or is that innate?
01:01:03I don't think so.
01:01:05But when you were talking about your love of podcasting, the word that popped into my brain, and there's a book by this title, was flow.
01:01:18And I just find people that are truly tilting against their passion, they never even think about it as work.
01:01:27And at times, the experience does go into this flow thing, like when you're done, you don't even remember doing it.
01:01:37Like you're just that much enamored with the whole thing.
01:01:41And because I've felt that, and I've seen it, I just, I really don't know how you could do that.
01:01:49I 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.
01:01:57And I don't know, I do think we get a lot of young people to do it for an extended period of time.
01:02:05The meat grinder thing.
01:02:09I just yesterday met with five of the top.
01:02:13I helped start this robotics honors program at Texas, and I met with five of them.
01:02:18And they're giving you their background, Eagle Scout, and it's 1580 SAT, and all that.
01:02:25Clearly, this human's been programmed to go take the hill on every single thing they do.
01:02:32But I don't think that's the path to greatness.
01:02:35You know what I'm saying?
01:02:37I just don't think, I don't think just being good at the grind is what it takes to be truly exceptional.
01:02:47Brute forcing creativity, sort of white-knuckling your way through miserable successes.
01:02:55It lasts for a good while, and might be sort of the activation energy you need to overcome some discomfort at the start.
01:03:01But I would agree, I think.
01:03:03And maybe if you're just so damn competitive, like winning all the time.
01:03:07That winning is your passion.
01:03:09It's a meta passion.
01:03:10That's possible.
01:03:11Yeah, that's interesting.
01:03:12And that's certainly some people, right?
01:03:13They just want to win.
01:03:14Yes.
01:03:15I think Michael Jordan would be a good example of this.
01:03:18Have you heard Novak Djokovic's interview where he's asked, "Why are you so good at tennis?"
01:03:24And he says, "I just like hitting the ball."
01:03:25I love that.
01:03:27Yeah, whereas, you know, Jordan invented rivalries.
01:03:33He invented slights against himself.
01:03:35Was it '92 or '93?
01:03:37Very driven human being.
01:03:38He wins some, I think it's his induction into the Hall of Fame.
01:03:41And during that speech, this is the moment that you've worked supposedly your entire career for.
01:03:49He takes a shot at somebody, right?
01:03:51He spends the entire speech just revealing all of the slights that from his past and this
01:03:59person and this person.
01:04:02You know, even at the moment where you've broken through escape velocity, you're out in space.
01:04:12I don't love that that much.
01:04:15You know, I love it.
01:04:16It's not the energy that I have.
01:04:17Yeah.
01:04:18So there's a, there's a, there's a counter example to that.
01:04:20There's this thing you can find on YouTube where Shaq was on that famous show that he
01:04:27does with Kenny and Charles and Ernie.
01:04:30And inside the NBA, I think it's called.
01:04:33He's at the All-Star thing and there's all these legends there.
01:04:39And he just kind of goes off on his own talking.
01:04:42And he talks for like five minutes and they don't interrupt him.
01:04:46And he's telling his story of how he made it and all the people that influenced him along
01:04:52the way and how he views all these legends as idols.
01:04:57And he just goes on.
01:04:58He's just thoughtful, like gracious for four or five minutes.
01:05:03And Ernie's crying by the time he's done.
01:05:06And I love watching it.
01:05:07I've watched it probably 10 times.
01:05:09I just love the notion that you carry that much, um, thankfulness for the others that
01:05:17helped you get where you are.
01:05:19And I think in conveying that and maybe in, and it makes him look like remarkable, you
01:05:27know, it really does.
01:05:29Like that he, that his brain's wired that way.
01:05:32I felt very proud of him.
01:05:34Like I have no reason to be proud of him.
01:05:36And he probably couldn't care less than I am proud of him.
01:05:38But it was, uh, his, I liked that.
01:05:42I liked that version better.
01:05:43It feels much more pro-social.
01:05:45Yes.
01:05:46I suppose the problem is, the problem is ultimately what matters is performance, especially in
01:05:54an industry like that.
01:05:55You know, if Michael Jordan was some middling or pretty poor quality basketball player, calling
01:06:04out all of these people and inventing random rivalries to try and motivate himself to go
01:06:10out, people would look and say, you're just bitter.
01:06:13And the same thing with Shaq.
01:06:15If Shaq who had a version of him that hadn't achieved all of that was, you know, proselytizing
01:06:22about these wonderful people and how grateful he would be called a suck-up.
01:06:26And this is, the medium is the message, but the medal is the message very much for this
01:06:33stuff.
01:06:34Well, and look, that is more of a finite game, right?
01:06:36Like that is, and I used downhill skiing, but there are like those kinds of competitive
01:06:41sports you may need to be sharp elbow to climb to the top.
01:06:45If you're an author, the same thing is not true.
01:06:47That's right.
01:06:48That's my main point.
01:06:49And most of the careers most of us chase, that's not, that's not a reality.
01:06:54Um, but, but I also have a principle, always give back, which is why I, I feel warmly about
01:07:01the Shaq thing, which is, I think that the minute you move from the first rung to the
01:07:07second rung of the ladder, if you take the time to appreciate the people that helped
01:07:12you with that movement, you will develop a process that you will feel really good about
01:07:17at the end of your life.
01:07:19And, um, your network of supporters will grow faster.
01:07:25You'll have more friends in your corner.
01:07:27You're seen as the pro-social hub as opposed to the person that stepped on a bunch as they,
01:07:33they come up.
01:07:34Yeah.
01:07:35You'll be able to weather the bad times and enjoy the good times more.
01:07:37But so you talk about honing your craft, kind of interested in what that looks like in knowledge
01:07:43work when there's, there's no clear scoreboard.
01:07:46Well, here, here's, here's what I would say is, and, and I think this relates to this college
01:07:52grind.
01:07:53I think some of these kids are so burned out by the time they get to the end of their senior
01:07:58year in college that they can't wait to not study anymore.
01:08:03Like they view it as, okay, 12 years plus four, 16, I'm done.
01:08:08And they're looking for a break from studying.
01:08:12And the best in their field, like Danny Meyer are studying all the time.
01:08:19And so that's a, that's a weird contrast like, and there are fields where continuous learning
01:08:26is somewhat required.
01:08:27The, the medical profession is one where that happens.
01:08:31Um, and obviously there are fields like a ballet where if someone says they work 16 hours a
01:08:38week or a day, we all applaud it, which is weird because if you said that about a engineering
01:08:44career, they'd say you're a bad human, you know, but whatever.
01:08:48Um, so this, this, this notion of learning constantly in your spare time, I think it's
01:08:55just the best test of whether you're truly obsessed with what you're doing.
01:08:59Do you remember when, do you remember when Elon took over X and he did that announcement
01:09:03post and he said, we are looking for people who want to work on the hardest problems possible,
01:09:08as long as they can at an unrelenting pace to try and change the world.
01:09:13And there was a lot of quote tweets of this saying, we're throwing it back to a version
01:09:19of work-life balance that is completely primitive.
01:09:23This is abuse.
01:09:25This is horrendous, all the rest of it.
01:09:27And don't get me wrong.
01:09:28There are certainly some bosses in some industries that will drive the employees so hard that
01:09:33it's irresponsible.
01:09:35But if you're stating it upfront, what all of those people that quote tweeted it and complained
01:09:42about Elon's horrendous working conditions failed to understand is there are people out
01:09:49there to whom that sounds like a dream.
01:09:53They want to work 18 hours a day, fueled exclusively on high quality stimulants and Chick-fil-A.
01:10:02Especially if they get to hang around with the smartest people.
01:10:04And they want to be pushing each other and they want, they want to send it.
01:10:07They want to send the living shit out of it.
01:10:09You know who's doing that right now, which is super interesting.
01:10:12The young AI founders.
01:10:14They've embraced this meme from China 996.
01:10:18It actually was developed in China, which means 9 a.m. to 9 p.m. six days a week.
01:10:25That's what it stands for.
01:10:26But they used the phrase and Silicon Valley got lazy in COVID.
01:10:31So you have the situation where the broader culture had moved from being formerly a bit workaholic to being lazy.
01:10:41And despite the, you know, they literally aren't coming into the office.
01:10:45You can go downtown San Francisco and look through buildings, you know, because there's so much cubicle space with no one there.
01:10:53And these young kids in this AI world are the ones you're talking about that want that experience.
01:11:00Who are some examples of those?
01:11:02I think almost all of, I'm serious, almost all of the AI companies in San Francisco have this mindset.
01:11:10Especially if they have a young founder, like a 2022, which is, but it, I'm agreeing with you.
01:11:19Like this notion that, okay, you don't like it because you don't think there's work-life balance.
01:11:24Do you think it should be illegal for them to do it?
01:11:27Like, I don't, they're going to choose their own life.
01:11:31It's kind of the argument for drug legalization, but it's workload legalization.
01:11:35Exactly.
01:11:36If you're doing it and it doesn't hurt anybody else, you do to your workload as you wish.
01:11:40But I would say this, if you're, you do need to recognize that you might one day be competing with someone that has that hunch.
01:11:50Absolutely.
01:11:51And that's where I go back to like, do what you love, because if you're sitting next to that person.
01:11:57And you're white knuckling it and they're loving every moment.
01:11:59Yeah.
01:12:00You're probably going to lose because they're at home learning in those extra hours stuff you're not.
01:12:05Like there's no way to keep up.
01:12:07Yeah, well, it is, even 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.
01:12:26Well, and the gap is going to grow.
01:12:28And I'll tell you one other thing which I stumbled upon, which I think is an interesting juxtaposition.
01:12:35If 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.
01:12:49But you don't love it.
01:12:50You're in that place you were talking about.
01:12:52I suspect for those people, AI scares the living shit out of them.
01:12:58Like they view AI as...
01:13:00Grind versus grind.
01:13:01It's going to crush me. I'm going to lose my job.
01:13:06Look at this world. It's unfair.
01:13:08Now, 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.
01:13:24They can now do more things faster than they wanted to do and they can achieve more than they were able to before.
01:13:34They get to run extra fast.
01:13:36So two people maybe in the same station in life, AI looks like the opposite to them.
01:13:44A threat or a nitrous turbo boost.
01:13:47Yes.
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01:14:58Can I read you an essay that I wrote?
01:14:59Sure.
01:15:00So, guidance doesn't sculpt us into something new. It exaggerates who we were already. The patent 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.
01:15:14Advice doesn't land evenly. It finds the path of least resistance and tends to be absorbed by people who already lean in its direction.
01:15:22So, I first started thinking about this when considering the post-Me Too instruction of "Don't be pushy with women," and I realized that it made conscientious, anxious guys even more timid, while the dudes that were blowing through boundaries just didn't take heed, exactly.
01:15:37Or another example of the prescription to just work harder. That gets devoured by the insecure overachiever, who's already bleeding effort into every crack of their day, while the genuinely lazy person just coasts past it unchanged.
01:15:51They're called to take more responsibility. It encourages the one who always thinks that it's their fault to carry even more of the load, while the ones who constantly point the finger elsewhere never change.
01:16:00There's a bunch of reasons. People filter it through their existing traits. It amplifies predisposition instead of correcting overbalance.
01:16:06We all want to be good, so we sort of over-index guidance that flatters our self-image, but I think the most influential one is that the pieces of advice that match our inner fears are the ones that we believe the most.
01:16:20So, 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.
01:16:28The sensitive man doesn't just hear "Open up more." He feels it confirms the worry that he's emotionally inadequate, even if he's already oversharing.
01:16:35For 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.
01:16:45This, to me, the disproportionate way that advice – call them advice hyper-responders – the same piece of advice goes in very different directions to two different people.
01:16:58I do still think that developing a grind capacity is important, but if you don't have the passion part, if you don't actually care about it, you can drive really, really fast in a direction that you don't want to go.
01:17:12And 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.
01:17:26Yeah. And look, I'm somebody that – I don't think you feel this if you switch jobs at three years, but when you reach a true retirement – and I'll be 60 next year.
01:17:41And when I decided that, okay, I loved every minute of being a venture capitalist, but it's time for me to pass it on to the next generation and move out of the way, it's reflective.
01:17:53Like, oh shit, I'm there. And I think it's hard when you're 25 – I think one of the benefits of being 18 is you don't see the end of times at all.
01:18:10And that gives you all kind of superpowers to play.
01:18:15There's some point at which you realize there's an end to all of this.
01:18:21And for this particular thing about your career, I think the sooner you can feel that, the better.
01:18:29Because if you do want a different at-bat – You want to front-load that fear a little bit?
01:18:36Yeah, if you can. I don't know if everybody can.
01:18:39Well, I certainly know that the regret-minimization thing – there's a variety of different exercises that have done.
01:18:48George, my housemate, he did this six years ago.
01:18:53I remember him telling me about this six years ago, and I thought it was insane.
01:18:56I kind of still think it's insane now, but I know he still does it.
01:18:58I think it's one morning a month he's got a reminder on his phone, and he wakes up, he lies in bed, and he imagines what it would be like to have no arms or legs.
01:19:10He viscerally thinks about what it would be like to have no arms or legs for 30 minutes.
01:19:19To be grateful?
01:19:20And then to be reborn into this body with the arms and the legs.
01:19:25So I've been really pushing hard over the last 18 months on emotional work, trying to get below the neck, as I've said.
01:19:36And I think a big part of it is this, that how many smart people who know all of the –
01:19:44they could do an expected value calculation about the likelihood of the success and what is the objective quantifiable utility of enjoyment versus –
01:19:54but then you've got hidden and observable problem coming through again.
01:19:57But 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.
01:20:07It's trying to overload emotion.
01:20:10It's like, oh my god, there's a great fucking workbook from – this is Tony Robbins, Unleash the Giant Within.
01:20:18But it's this weird 1994 Audible workbook, and it's only an hour and a half long.
01:20:25And I can't even find it.
01:20:26Listen, I've got it in my Audible.
01:20:27George has got it in his and a couple of our friends that we've sent it to.
01:20:29I can't even find it publicly.
01:20:31I don't know what fucking – it's your hacker friends that have got us under the back.
01:20:34And in it, he's got this thing where he says, imagine what it's cost you in the past.
01:20:39Imagine what it's costing you now.
01:20:41Imagine what it will cost you in the future.
01:20:43He wants you to overload the pain, like feel as much of it as possible.
01:20:48All of the rumination and the grief and the wistfulness and everything that's from what's happened.
01:20:54And right now, how is it affecting you?
01:20:57How is it limiting your time?
01:20:58How is it stopping your happiness and the future?
01:21:01What is it going to do to you?
01:21:03What's life going to be like if nothing changes for a decade, for two decades, three decades?
01:21:07What are you going to be like?
01:21:08What are your relationships going to be like?
01:21:10The quality of your mind, your health, everything.
01:21:12And then imagine what life could be like if you changed.
01:21:16And he's trying to get you to oscillate between this pain-pleasure principle.
01:21:20And I've had to make some – I moved from the UK.
01:21:25I was 32 years – nearly 33 years old with a successful career in the UK running nightclubs,
01:21:32one of the biggest events companies in the north of England.
01:21:34It's something I dedicated 15 years of my life to.
01:21:37COVID had just happened and nightclubs were just reopening.
01:21:39The clubs reopened and I didn't want to go back.
01:21:43I just wanted to do the podcast.
01:21:45And that was the exercise that you went through.
01:21:47And I presume zero regrets about the move.
01:21:51This is the best single decision that I ever made in my entire life.
01:21:55But even with that, going back, I don't have the borrowed authority of my fears from back then.
01:22:02So this is a great idea from Morgan.
01:22:05I'll send you this once we're done, this wonderful blog post.
01:22:09He talks about nostalgia and about how we were unable to see the pains from the past,
01:22:15especially when we've moved on.
01:22:17We don't see our fears from the past particularly well.
01:22:20So him and his wife are talking about when they used to live in New York
01:22:24and they were in their 20s before they had kids.
01:22:26And he's saying to his wife, "Wasn't it so wonderful?
01:22:28We used to wake up on a Saturday. We could lie in bed.
01:22:30We'd get a coffee. We could just walk around.
01:22:33We had no responsibility. We were just kids. It was so beautiful."
01:22:36And his wife goes, "What are you talking about? You were miserable.
01:22:42You had no idea if your career was going to work.
01:22:44We constantly had money problems. We didn't know if we were going to make it.
01:22:47You were worried about where your future was going."
01:22:51And Morgan realized that in retrospect, all of his fears that were a waste of time,
01:22:55he knows were a waste of time.
01:22:58He didn't need to worry.
01:23:00So what he sees is how he should have felt knowing how well life was going to go.
01:23:07So it's the same reason that no one ever believes we're living through a golden era.
01:23:11Golden eras only exist in our memory.
01:23:13And all of that together.
01:23:16I know that I had the fear. I've got the fucking journal.
01:23:20I've got the journals on my Apple Notes still of what if I do this thing and it goes wrong
01:23:25and everyone's going to laugh at me and I'm going to have to come back
01:23:27and live in my mom and dad's spare room and I'm going to have a gluten intolerance
01:23:30and a club foot and be under a bridge and it's all going to be...
01:23:33And yeah, had it not gone well, maybe that would have been the case.
01:23:37But that is the worst possible scenario.
01:23:42And there's gradations between the best one and the worst one.
01:23:46But yeah, I'm really proud of making that decision.
01:23:49But even that, the best single decision I ever made in my life,
01:23:55I still had to apply a fucking galactic volume of pain
01:24:01and the same amount of pleasure in a desperate attempt to galvanize me to do it.
01:24:07So yeah, even decisions which in retrospect feel very obvious,
01:24:13I think at the time require inhuman amounts of motivation
01:24:17to get the activation energy to get you moving.
01:24:20I like the battle card notion. I mean, it's similar to some of the Designing Your Life stuff,
01:24:25but allowing yourself to fully imagine the other reality and without the comparison.
01:24:34While you're doing it, really imagine every element of it on its own
01:24:41and then maybe go back and do the one you have and then battle card them.
01:24:45I love that idea.
01:24:46I think one of the reasons I was a useful venture capitalist
01:24:51and one of the reasons this regret minimization thing worked for me
01:24:56is I think I'm very good at bringing forward the future in my brain,
01:25:01like extrapolating back, if you will, almost like a life NPV kind of thing.
01:25:08I'm just able to do that.
01:25:10It's like reverse time travel.
01:25:12Yes, and it makes those exercises work better,
01:25:16the fact that I somehow can do that in my brain.
01:25:21Speaking of that, you're a very successful investor.
01:25:24What were you looking for in the founders that you invested in?
01:25:29What were the traits? What was the global decision framework?
01:25:33And a lot of VCs say the same things over and over,
01:25:37so I'm a little hesitant, but I'll do it anyway.
01:25:40The one that took me the longest to fully recognize
01:25:43is how important product instincts are, so that's critical.
01:25:48Most of these companies are riding some new wave, like this AI wave,
01:25:54and the product surfaces of the new thing aren't as well understood
01:26:00as the ones of the old thing.
01:26:02Think about the mobile movement.
01:26:04So you're predicting.
01:26:05And you need instinct to get that right.
01:26:07You just need instinct.
01:26:09Think about humans and how humans like to interface with things
01:26:13and a whole bunch of stuff, so product's a big one.
01:26:17Salesmanship is a huge one that people probably don't think about enough,
01:26:22but if you're a founder, you're selling to new investors.
01:26:27You're selling to employees.
01:26:28You own the company culture and the perception of the company.
01:26:33You're striking deals.
01:26:35You're selling to customers.
01:26:36You're just out selling all, you're the number one sales,
01:26:40you're the chief salesperson for your company,
01:26:42and if you're no good at it, you will struggle.
01:26:46So that's another one.
01:26:48Determinism, you know, and it kind of goes back to everything
01:26:51we're talking about with Chasing Your Dreams,
01:26:53but you know, Josh Wolf at Lux Capital says,
01:26:56"Chips on shoulders put chips in pockets."
01:26:59And like someone that maybe failed a couple times,
01:27:05Got a point to prove.
01:27:07Oh, man, you want to feel that.
01:27:09Like you want to feel that they're never going to give up.
01:27:13Bit of grit.
01:27:14Yes, like not a bit.
01:27:15Like you want top one percentile.
01:27:18Yeah, yeah, yeah.
01:27:19You want to be afraid a little bit about how determined they are, you know.
01:27:26What was that line,
01:27:27"Is this person going to do this no matter what?"
01:27:29Was that Bezos?
01:27:30Bezos, I asked Bezos, you found that.
01:27:33I asked Bezos once how he could be such a successful angel investor
01:27:38because he's running the largest employment company in the world.
01:27:42There's other shit to do.
01:27:43Yeah, exactly.
01:27:44He has less time than you to scrutinize.
01:27:46No, way less.
01:27:48And he said the only thing he looked for is the determinism.
01:27:52Is this person going to do this no matter what?
01:27:54And all of his questions.
01:27:55That's so cool.
01:27:56All of his questions were around that one very thing.
01:27:59What if this, how would you approach that?
01:28:01How have you in the past done the got over?
01:28:03Why are you doing it?
01:28:04Like, you know, what if this comes up?
01:28:07Like what if someone offered you the, you know.
01:28:09I had a conversation with a friend a few years ago
01:28:13and he gave this wonderful example of champions.
01:28:17And he says everybody looks at champions to try and find what they have
01:28:20that other people don't have.
01:28:22But they've got it completely backward.
01:28:24Champions miss something that normal people do have, which is an off switch.
01:28:28Yes.
01:28:29And when you're talking about a zero-sum game
01:28:32or a game that's more competitive now in the world,
01:28:35you're looking for somebody who will go to unreasonable lengths.
01:28:39And I suppose this is why strong ethics, too,
01:28:44if you care about the ethics of the companies that you're going to invest in,
01:28:47because that chip on shoulder, that determinism.
01:28:50Could push you right across the line.
01:28:52Very, very.
01:28:54A lot of these people live on the line.
01:28:56Yeah.
01:28:57It is what it is.
01:28:59When you said that, I couldn't help it.
01:29:01And it's horrible, the accident she had,
01:29:04but I couldn't help but think of Lindsey Vonn.
01:29:06Like she had a –
01:29:07Who's that?
01:29:08Lindsey Vonn's a downhill skier that's 41, 42 and is in the Olympics right now.
01:29:13Okay.
01:29:14And, you know, she had retired a while back and came back, trained again.
01:29:19Her trial times were highly competitive.
01:29:23But early when she got to Italy, she injured her ACL.
01:29:30And she put on a brace and said, "I'm going to compete anyway."
01:29:35And unfortunately had an accident.
01:29:38Went to the hospital, had three surgeries.
01:29:40Snapped her shit.
01:29:41Yeah.
01:29:42But to be in your 40s and coming back –
01:29:46In some ways –
01:29:47And somewhat injured.
01:29:48And I'm like, "I'm going anyway."
01:29:50I'm sending it anyway.
01:29:51Look, I didn't know about this story.
01:29:55This just happened like a week ago.
01:29:57I kind of like it.
01:29:58I kind of like it.
01:30:00What a way to go out.
01:30:01Yeah, fair enough.
01:30:02You're going to be laid up.
01:30:03Better to burn out than to fade away.
01:30:05Well, could you imagine, again,
01:30:07and this is a fucking wonderful little microcosm of exactly what we were talking about.
01:30:12What about that open loop?
01:30:13Yeah.
01:30:14Would my ACL have held up?
01:30:15Yeah.
01:30:16Would it have held up?
01:30:17Am I going to go back at 45?
01:30:19Nope.
01:30:20No, no.
01:30:21It's the last shot.
01:30:22This is it?
01:30:23Yeah.
01:30:24So, I kind of like it.
01:30:26Fair enough.
01:30:27I'm sure that her surgeon doesn't like it.
01:30:29Or maybe he does if he's paid well.
01:30:30But I'm sure her physio and her strength and conditioning coach don't like it.
01:30:33Yeah.
01:30:34Going back to the founder thing, is the founder more important than the company to you in some
01:30:40ways?
01:30:41Would you bet just on a founder that this person will find a thing?
01:30:44Well, here's one proof point that would speak to this is there are multiple companies that
01:30:53the original idea completely failed and the founder was able to pivot to something entirely
01:31:00new and be wildly successful.
01:31:02Like?
01:31:03Slack is an example.
01:31:04It was a game company and the game failed, but they had built this tool to develop the
01:31:10game.
01:31:11I didn't know about that.
01:31:12It's so cute.
01:31:13Discord, who's one of our companies, was also a game company that failed and launched this
01:31:21Skype alternative for communicating during games that became wildly successful.
01:31:27And for any venture capitalist that's been through one of those pivots, they're famously
01:31:32known as pivots now, it's all about the person.
01:31:36Like, it's all about the founder.
01:31:38Like, there's also a data point that most venture capitalists will quote, and I'm sure
01:31:44it's not scientific, but a new CEO hires a 50/50 bet at best.
01:31:50So why, if you're doing positive, like trying to run MPVs, would you even take the risk of
01:31:58hiring a CEO because you're going to, there's a 50/50 chance you'd just get a bad apple,
01:32:04in which case it's all toast.
01:32:06So, yeah, there's, and that lore goes beyond me.
01:32:10I mean, I think the founder mythology, if you will, is quite high in Silicon Valley, for
01:32:19all those reasons.
01:32:21Now, there are times where you have no other option and there are, there's way more stories,
01:32:26this is kind of an odd fact, but companies that serve businesses have a much higher success
01:32:32rate of replacing the founder than companies that serve consumers.
01:32:37Why do you think that is?
01:32:38My best guess is consumers are more fickle and that product thing is just more artistic,
01:32:46you know, more like
01:32:47That one's about to taste again.
01:32:48Yes, more like a movie than business, and business products are more systematic.
01:32:55Yeah, we can algorithm that down too.
01:32:58Steve Jobs once said that the difference is the buyer in a business isn't the user, and
01:33:06he made that point, and that may be it, like that may be the essence of it.
01:33:11That's cool.
01:33:12I, this thing that the beverage that you're drinking is mine, and that's the first big
01:33:17company that hasn't been something that I've directly operated aggressively myself that
01:33:21I've founded, and one of the interesting elements that I've seen with this, where we did a raise
01:33:30last year, we raised $3.4 million, and right now we're in the middle of raising six and
01:33:36a bit.
01:33:37I'm watching Luke, who is one of the co-founders.
01:33:41Today, he drove from Portsmouth on the south coast to Leeds, which is five and a half hours
01:33:51away.
01:33:52It's fucking forever away.
01:33:53Drove to Leeds for one investor meeting, just sit down with this guy, and when you think
01:33:58about as you're sort of reeling off all of these different traits that you would have
01:34:01sort of the obsession, the determinism, and what's been cool is to see, you almost get
01:34:07to learn what people think of you when you do fundraising, when you're trying to get cash
01:34:12to inject into a business that's yours.
01:34:14You almost see in the responses from people, and a couple of times, we sent the deck out.
01:34:21This was in the first one.
01:34:22So, we send this deck out, and it's all sexy, and it's got the numbers and the projections
01:34:28and all the rest of it.
01:34:29One of my friends sent a reply to the deck, and he made a meme.
01:34:34Have you seen the Midwit meme?
01:34:36Are you familiar with this?
01:34:37On the left-hand side is sort of a Neanderthal guy, and on the right-hand side is a sage that
01:34:41looks like a Jedi.
01:34:42In the middle is a guy that overcomplicates everything, and he's sort of screaming and
01:34:46getting...
01:34:47The joke is that the guy on the left and the guy on the right always agree.
01:34:50If it's going to the gym, it's lift weights, eat protein.
01:34:54Lift weights, eat protein.
01:34:55The guy in the middle, "I must ensure that my scientifically accurate and pre-digested
01:34:59whey is consumed within 30 minutes."
01:35:01And he replied with that meme, and the guy in the middle said, "Read the deck, make expected
01:35:08value calculation, check against finances."
01:35:11And the guy on the left and the guy on the right said, "I bet on Chris.
01:35:14I bet on Chris.
01:35:15I bet on Chris."
01:35:16And it was really interesting to see, do people look at you or Luke, who's my guy, or James,
01:35:23who's one of the other co-founders, do they look at you and go, "You'll make it work no
01:35:28matter what."
01:35:29That was cool.
01:35:30That was cool.
01:35:31It's the first time that I've ever...
01:35:32You can take that too far.
01:35:34I've met with founders who are anti-deck.
01:35:37I even wrote a blog post called "In Defense of the Deck," because they would walk...
01:35:41Gotta make sure that you don't misspell one of those words, but yes.
01:35:45They walk in the room and just want to chat, and you know nothing about the business.
01:35:50You know jack shit, and I don't want to learn about the business through a prompt with this
01:35:55human.
01:35:56It's too hard.
01:35:57You can't get enough information fast enough through that.
01:36:00So in this blog post, which I'd encourage people to find, I show Steve Jobs, Marc Benioff,
01:36:08Jeff Bezos in front of a deck.
01:36:09Look guys, it's good enough for them.
01:36:12No, no, no, no.
01:36:13I don't disagree.
01:36:14I'm not advising people.
01:36:15People are prepared.
01:36:16If you're fucking investing in your tonic, please scrutinize them.
01:36:19But I want to say one other thing about this, because I think it gets more to the point of
01:36:23what you said.
01:36:26Most people perceive venture capitalists to be making investments the way maybe a buy-side
01:36:32public investor might be.
01:36:34If it's positive IRR and I'll make 14%, I'll do it.
01:36:39But venture capitalists have a limited number of boards they can go on, probably two a year.
01:36:45And so they don't have unlimited shots on gold.
01:36:49They can't fund everything that's over 12% hurdle rate.
01:36:53They have to fall in love.
01:36:55And it goes back to what we were saying with stories and all this stuff about people.
01:37:00They're going to pull the trigger because they have an emotional positive bias to go do this
01:37:06thing.
01:37:07And that taps in, it's about Chris for sure, but they also need to love the category and
01:37:14love the idea and want to spend 10 years working on the problem, all those things.
01:37:21They have to flip from zero to one in their own head, in this human's head.
01:37:27Does that make it harder for businesses that are less sexy?
01:37:31Of course.
01:37:32Unquestionably.
01:37:33That's why it's like these mid-market PE people, they go do those things.
01:37:43I would never be motivated by it, but I'm not necessarily shitting on them too bad.
01:37:50You can make money.
01:37:51There are things to be done.
01:37:55But I also would say, and I think this is important, there are businesses that shouldn't take venture
01:38:02capital.
01:38:03And a series A typically leads to a B and typically leads to a C. And the ownership that a founder
01:38:10has can shrink pretty dramatically.
01:38:13And then the exit value you need to make the same amount of money had you sold it a hundred
01:38:21percent on sweat equity is now 10 times higher.
01:38:25And just make sure you think through all that.
01:38:27Somehow through the use of these 19 credit cards and everything, Bert Beverly retained
01:38:33100% of his.
01:38:34Unbelievable.
01:38:35Do you know Gymshark?
01:38:36Are you familiar with Gymshark?
01:38:37No.
01:38:38So it's probably one of the biggest British companies to activate.
01:38:43I'm actually wearing the trousers right now.
01:38:45And Ben, the CEO and founder, is a good friend.
01:38:49And it is a 2.6 billion pound company.
01:38:57And it is entirely private.
01:39:00And I think he's still got 75% of it himself.
01:39:04Yeah.
01:39:05It's a lot.
01:39:06But I would say even if you're going to sell for 20 million, there are far more companies
01:39:11that want to do a tuck in $20 million acquisition than want to do a half a billion acquisition.
01:39:16What's the size of the market you're selling it to?
01:39:19Plus, if you're a large public company, you can do a $20 million acquisition without filing
01:39:25anything, without telling anybody, your boss won't care.
01:39:29If you own 100% of a $20 million company, that's lifetime wealth.
01:39:34Trying to make $20 million selling a company for half a billion, that's hard, because it's
01:39:39hard to sell a company.
01:39:40So fewer people that can buy it, it's going to have more scrutiny that goes over the top
01:39:43of it.
01:39:44You've now diluted down.
01:39:45You need audited financials, they're going to have to file an essay.
01:39:51There's all this stuff.
01:39:52It gets really hard to sell a company for a lot of money.
01:39:55I don't ever think about the market of selling a company.
01:39:59You think about the market of the company that it sells to.
01:40:02Yes.
01:40:03That's so cool.
01:40:04Yes.
01:40:05Yes.
01:40:06It matters.
01:40:07It really matters.
01:40:08It really matters.
01:40:09And by the way, if you sell that first company for 20 million that you own 90% of, and you
01:40:14want to go take the big shot and raise money, well, great.
01:40:18Now you've got freedom, flexibility, you can take all the risk you want, you know?
01:40:22Do it the second time.
01:40:23I've seen, I've heard a bunch of different horror stories about founders who've diluted
01:40:27down and diluted down and diluted down.
01:40:30And then before they know it, they're like, what the fuck am I working for?
01:40:33No doubt.
01:40:34Lick pref is a beast.
01:40:36What's that called?
01:40:37Liquidation preference.
01:40:39So venture capitalists typically take preferred stock and it has a term called liquidation
01:40:44preference, which means in a sale, they get the option to basically treat it like debt.
01:40:49They get paid out first in a sale.
01:40:53And so if you've raised, in these days, these AI rounds, if you raise 500 million, Lake Common
01:41:00doesn't even participate until you get a sale over that, technically.
01:41:05Now it's often there are carve-outs because they have to get something done, but the bigger
01:41:11that number gets, the more weighty it is.
01:41:13Yeah.
01:41:14I mean, I feel fortunate when we did the first raise, I bought back in.
01:41:18I didn't want to dilute.
01:41:19Oh, nice.
01:41:20I threw more money in.
01:41:21I threw more money in, actually.
01:41:23And by the way, the investors love seeing that, love, love, love seeing that.
01:41:27I was like, I am not, in fact, I gained, I gained share of Nutonic when we did the raise.
01:41:34So I bought in over the top of where I was already while we were diluting down.
01:41:38It's hard to do.
01:41:39It was.
01:41:40I mean, James, James wanted a new Porsche and he was very gracious and we shifted some stuff
01:41:45around and I can't remember where else I took it.
01:41:47That's awesome.
01:41:48But no, it was, it was cool.
01:41:49And it's been really fun sort of learning about that world and now it, being able to see what's
01:41:57happening, especially in the world of AI at the moment.
01:42:00Well, that's a question, what, what are you most excited about with regards to the industry
01:42:07of AI and what do you think is overblown?
01:42:11I mean, it'd be a little redundant, but the thing I'm most excited about is just the personal
01:42:16empowerment.
01:42:17You know, there's all kinds of anthropologists that will tell you, we evolve with our tools.
01:42:23Like, like it's very clear, right, if I had a plow and a tractor and a, and a, and a computer
01:42:31and a chemistry set and the other guys, the guy in naked and afraid, like I'm going to
01:42:36be more involved than I can do more stuff.
01:42:40And this is the latest of those things.
01:42:43And anyone that is a skeptic or, and I've met a lot of like the top academicians that are
01:42:51skeptics and all this, you are, you're no different than the Luddites with the, with
01:42:57the looms in Europe.
01:42:58Like you're just not, it's the modern version of that.
01:43:02And the number one thing you can do to future-proof yourself is to run at it, like to know whatever
01:43:10industry you're in, there is an edge of what is AI capable of in this industry and you want
01:43:16to be right there, you want to be aware of exactly what that is.
01:43:22And if you are the most AI productive human in your field, you're not getting fired.
01:43:30You're, you're the one they're asking all the questions of, like, what's this capable
01:43:35of?
01:43:37And so I, in the, in the chapter I have on Hone Your Craft, I say, study the history and
01:43:42study the edge.
01:43:44Like if you can quote from the founding fathers of your industry and you know exactly where
01:43:49the technological edge is, you look like a unicorn.
01:43:53Going in the middle is where you die.
01:43:55Yeah.
01:43:56I mean, everybody knows the middle.
01:43:57Like I'm just talking about differentiating yourself.
01:43:58Of course.
01:43:59Of course.
01:44:00Yeah.
01:44:01So anyway, I, I find, I mean, I haven't, I, I, I'm anxious.
01:44:05This is why also why I was a useful, I use the word useful, venture capitalist.
01:44:10I have FOMO about new shit that I don't understand.
01:44:14So up until at least a year or two ago, if something, if there's an app in the app store
01:44:19in the top 10, I've never heard of, like hives, like I have to know.
01:44:26You're allergic to ignorance.
01:44:27Yeah.
01:44:28I'm coming off of it a bit.
01:44:29Cause I haven't done a claw bot yet, which I feel guilty about.
01:44:32Well, you can't get it.
01:44:33You can't get a fucking Mac mini.
01:44:34That's why.
01:44:35You're not going to be able to buy them.
01:44:36They're all sold out.
01:44:37But I feel guilty about that.
01:44:39Yeah.
01:44:40Yeah.
01:44:41You've got massive FOMO.
01:44:42But it's useful.
01:44:43Like, and so anyway, that I, I think that, um, the there, there, I would also say this
01:44:50about AI.
01:44:51If you're not leaning in, not only people have said there's prompt engineering skills.
01:44:56Not only are you not learning that, but I find every day I think of a new way to use it in
01:45:03a new way to test what it's capable of.
01:45:07And if you're in it every day, you're helping to explore that boundary and you're all the
01:45:14sudden learning new things.
01:45:16You understand what I'm saying?
01:45:18Like, um, I had this great experience with the, with the concluding chapter in the book.
01:45:24So my, you know, almost done wrapping up, feeling good.
01:45:30And the editor says, bill, take a shot at the conclusion this weekend.
01:45:35So I spent six hours, seven hours.
01:45:38I sent him something.
01:45:39He's like, this sucks.
01:45:40Like first time, like it was really the first critical, he didn't use that phrase.
01:45:44Yeah.
01:45:45I really don't like this.
01:45:46So I asked chat GPT in the pro version, the 200, 300 hours a month, whatever it is, write
01:45:52me a 20 page report on the best concluding chapters in nonfiction books of all time.
01:45:59And give me a summary of each and what made it special.
01:46:02And in reading through that list, I noticed that eight or nine of the 10 took an orthogonal
01:46:10direction to the book.
01:46:11So it didn't summarize well, it brought in a new, new perspective.
01:46:17And that gave me an idea.
01:46:19I then went and ideated on that concept and it gave me a new idea to take it in a different
01:46:25direction.
01:46:26And what was the editor loved it, huh?
01:46:30What was the idea?
01:46:33I'll give this one away.
01:46:37The concluding chapter is titled It Ain't Easy.
01:46:40And so the whole book is an exercise in trying to encourage you to go do this.
01:46:47And this is a little warning at the end, like, it ain't easy.
01:46:52You got to struggle.
01:46:53You got to suffer.
01:46:54You got to be okay with failure.
01:46:56In praise of the grind.
01:46:58Yes.
01:46:59And the editor loved it.
01:47:00He should.
01:47:01I think that's an important message.
01:47:02Yeah.
01:47:03So if I don't have AI, I don't do that.
01:47:06And it didn't write it for me.
01:47:09It just gave me a new lens for how to think about it.
01:47:13When it comes to the AI thing, what do you think it's going to do to the field of work
01:47:17generally?
01:47:18What areas would you be worried that are going to be obsolete?
01:47:23Anything that was synthesizing, I mean, so the LLM, large language model, is really good
01:47:31at text.
01:47:32Really, really good at text manipulation.
01:47:35So if your job involved searching for text, summarizing text, anything like that, paralegals
01:47:44are already under threat.
01:47:47And I have talked to lawyers that have drastically reduced the size of their paralegal force.
01:47:54I've talked to them.
01:47:56That has already happened.
01:47:58Coding, it turns out, is highly structured text.
01:48:03More structured than text itself, right?
01:48:07If you think about it, it's got more small rings.
01:48:11There's more freedom in actual language text than in coding.
01:48:15And so coding is under threat.
01:48:19And the best people that will write or will generate the most code in the future are the
01:48:24ones that learn to be able to harness that tool the way a farmer learned to use a tractor
01:48:31instead of plowing.
01:48:33And that's your only choice.
01:48:36There's no hand hoe-ers anymore.
01:48:39They don't exist.
01:48:41And so this text thing's a big deal.
01:48:45If you translated something, that's a dangerous job.
01:48:50Someone needs to kind of make sure the translation's right, but that's a different job.
01:48:56It's more of an editor of translation.
01:49:00And that's an opportunity to move upstream.
01:49:02Be the one that's best at exercising that with this tool.
01:49:07But the old tool doesn't work, like it's not going to be real.
01:49:12If you were 21 and starting again with no knowledge or connections, what do you think you'd be
01:49:17focused on?
01:49:18What would you do?
01:49:20It would definitely be related to AI, I mean it just would.
01:49:24Like I'd be rolling around in it more.
01:49:28I would definitely have already launched 10 clawbots versus now where I don't have that
01:49:34need to see what's possible.
01:49:37I'm fascinated by the agent idea for a personal assistant like a running buddy.
01:49:45I just find that fascinating.
01:49:50Another one that I kind of am fascinated by, I think someone will build a new CRM from scratch
01:49:57that will be used by small companies that don't have a CRM because it's easier to start with
01:50:03zero in the database.
01:50:05And I think that will be super clever, that product.
01:50:08I don't think you can get there from Salesforce because you've got this huge database with
01:50:13all these fields and forms that no one wants to look at.
01:50:17And if you start with that as your construct, I think you'd build the wrong thing.
01:50:21Does that make sense?
01:50:22Because you're trying to backwards integrate something that's already a little jagged.
01:50:28And I don't think the user wants to even see that stuff.
01:50:32That's interesting.
01:50:33And so whatever the storage mechanism is, I don't think it will be visible to the user
01:50:40in the way that a database-type enterprise app historically did it.
01:50:50So anyway, those are things that pop into my brain when you say that.
01:50:54Those are things I'd be playing with.
01:50:56I know that you're a big reader.
01:50:59What have been the books over the last couple of years that you have not been able to stop
01:51:03telling people about?
01:51:06The second half of Range impacted me in a good way.
01:51:11David Epstein.
01:51:12Yeah.
01:51:13And the book's known for being this antidote to Malcolm, although they're very close friends.
01:51:17In fact, Malcolm's quoted on the cover of Range, I think.
01:51:22But the book, people talk about this generalist versus specialist and this comparing of these
01:51:28two athletes.
01:51:30But he gets into a very different subject in the second half of the book.
01:51:33He gets into this notion, which I'd always heard a phrase called far analogies.
01:51:41But he gets into this notion that people that switch industries or switch careers or switch
01:51:47academic focuses tend to be the biggest innovators of all time.
01:51:54And they come into something with a different mental model than the people that came up through
01:52:01the field.
01:52:02Like if they enter through the side door.
01:52:04You understand?
01:52:05And it relates to the generalist.
01:52:06They see things differently.
01:52:07Yeah.
01:52:08Yeah.
01:52:09And they're able to bring patterns from or see patterns other people may not see.
01:52:14And I just find that fascinating.
01:52:16I touch on it in a couple of the chapters.
01:52:19In the learning chapter, in the peer chapter, I say, if you make it far enough, you want
01:52:25to stretch the peer to someone that's maybe in a different industry.
01:52:30You want to stretch the learning to other industries.
01:52:34And it's where you find some of the biggest nuggets.
01:52:38It's more noisy.
01:52:39You're wading through.
01:52:40It's harder.
01:52:41It's less aligned.
01:52:42Right?
01:52:43Yeah.
01:52:44Yeah.
01:52:45But the insights are power loss step changes.
01:52:46It'd be like you listening to someone talk about great writing technique and get an idea
01:52:53for the podcast.
01:52:55Well, one of the things that I did about four years ago when I first moved to America was
01:52:59I got obsessed with cinematography.
01:53:02We obviously there's cameras and videos and stuff here.
01:53:05But we started doing this thing called the Cinema Series.
01:53:07And this was shot like a movie.
01:53:09And it culminated Episode 1000 was me recreating the house from Interstellar on a 85-foot video
01:53:20wall, the biggest video wall in Texas, using the same technology that Star Wars uses.
01:53:24And we rendered the entire scene in Unreal Engine 5 and then did set dressing.
01:53:30So we had live elements of dirt on the floor and cactuses.
01:53:34And we reversed it fucking Airstream in.
01:53:37And I sat opposite McConaughey, and I sat him down, 11th anniversary of Interstellar.
01:53:44And we were sat in front of the house from the movie.
01:53:47And that was because I started learning about this and I started getting friends that were
01:53:50from the cinematography industry and I started asking them, "What would you do if you were
01:53:54trying to elevate a podcast?"
01:53:56And then we did some cool things.
01:53:58And it's largely a passion project wing of what we do, but it's cool.
01:54:05In his famous Stanford graduation speech, Jobs said if he had never taken the calligraphy
01:54:10class, he doesn't know if he builds the iPhone the right way, you know, and the Mac, you know.
01:54:16It may or may not be, it may be, it may just be kind of nostalgia speaking, but there are
01:54:23things you can borrow from learning far away that can be very impactful.
01:54:28And it's hard to know at the time, like when you're consuming it.
01:54:31That's why I call it a bit of a superpower or advanced level.
01:54:35I think I call it.
01:54:36It's not easy.
01:54:37Well, because you're translating, it's like an exchange rate between something else and
01:54:41this.
01:54:42So is that just cool for them to really take what that musician's doing or is this relevant
01:54:48to me?
01:54:49So I guess taste, discernment, and when I think about areas that AI can't replicate, community,
01:54:57networking ability, taste, discernment, those are the, I'm sure there's tons more, but those
01:55:03are the ones at least for me with what I do.
01:55:07It's not going to build a friendship with this other person that I want to hang out with.
01:55:13That's right.
01:55:14I agree with that.
01:55:15It can't choose, is this the right guest?
01:55:17And the MrBeast approach would be, well, there are just quantifiable metrics of how this person
01:55:24appears on a balance sheet.
01:55:25What's the likelihood of this person being a big play guest or whatever.
01:55:32But that also doesn't account.
01:55:33That's a local maximum, which is everybody's got the opportunity to operate for that, to
01:55:38optimize for that.
01:55:39Whereas if you're trying to refine for the taste, that's different.
01:55:44Bill Gurley, ladies and gentlemen, Bill you're fucking awesome.
01:55:47Thank you for having me.
01:55:48I really appreciate it.
01:55:49A lot of my friends said you're going to love his energy and sure enough, you're a legend.
01:55:53I'm glad that you're occupying some of those high rises.
01:55:56I've always wondered who lived in them.
01:55:58Where should people go to check out everything you're doing?
01:56:03So I've historically spent most time, we were an investor in Twitter early on.
01:56:07So I've developed my ex profile the most and that's where I post most stuff.
01:56:13So it's B-G-U-R-L-E-Y.
01:56:16There's an Instagram account that I'm, for the first time in my life, developing for the
01:56:21book.
01:56:22Congratulations.
01:56:23Welcome.
01:56:24Yeah, it's a different world.
01:56:25I feel like such a neophyte.
01:56:29In Twitter, I get everything in, like I understand Instagram.
01:56:33Instagram's a different language.
01:56:34Yeah, it's a different language.
01:56:35I'm figuring it out.
01:56:36Heck yeah.
01:56:37Bill, I appreciate you.
01:56:38Thank you, sir.
01:56:39Thank you very much for tuning in.
01:56:42Congratulations for making it to the end of an entire episode.
01:56:48Another one that I think you'll enjoy is right here.