Tim Ferriss - Curating Curiosities - [Invest Like the Best, EP.369]

My guest today is Tim Ferriss. Tim is a writer, podcaster, and investor. He has written five best-selling books, has been an early-stage investor in Facebook, Uber, Shopify, & other household names, and is the host of one of the biggest podcasts in the world. He started The Tim Ferriss Show as an experiment in April 2014 and has deconstructed world-class performers ever since. Last year, his show crossed 1 billion downloads. Together, we deconstruct his podcast and approach to life. We talk about the art of interviewing, the business behind his podcast, and what motivates Tim to keep teaching through his writing and podcast. Please enjoy this great conversation with Tim Ferriss. Check Out Invest America 2024 Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the only investment research platform built for the investor. With traditional research vendors, the diligence process is slow, fragmented, and expensive. That leaves investors competing on how well they can aggregate data — not on their unique ability to analyze insights and make great investment decisions. Tegus offers an end-to-end platform with all the data you need to get up to speed on a company or market: up-to-the-minute financials, customizable models, management and culture checks, and, of course, our vast and growing library of expert call transcripts. Tegus is changing the world of expert research. Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:03:32) The Evolution of Podcasting with Tim Ferriss (00:09:56) Crafting Meaningful Conversations (00:13:26) What Makes Tim Feel The Most Alive (00:24:06) Who Tim Considers To Be His Mentors (00:29:06) The Ingredients Of A World Class Performance (00:31:06) The Business Side of Podcasting (00:43:15) Identifying Emerging Trends (00:50:12) Lessons From Building a Small, Efficient Team (00:52:32) The Power of Constraints in Personal and Professional Growth (00:53:10) Innovating Against the Grain (Anti-Video Experiment) (00:54:54) Navigating Fame, Money, and Power (01:02:00) The Impact of Sharing Difficult Stories (01:06:18) Meta-Learning: A Framework for Fast, Effective Learning (01:12:32) Reflecting on a Decade of Podcasting & What’s In Store (01:24:41) The Kindest Thing Anyone Has Ever Done For Tim

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Patrick O'Shaughnessy?

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• 0:35Patrick O'Shaughnessy?

  Hello and welcome, everyone. I'm Patrick O'Neal and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories and strategies that will help you better invest both your time and your money. Invest Like the Best is part of the Colossus family of podcasts and you can access all our podcasts, including edited transcripts, show notes and other resources to keep learning at joincolossus.com.

• 1:00Speaker 01

  Patrick O'Neal is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.

• 1:29Patrick O'Shaughnessy?

  My guest today is Tim Ferriss. Tim is a writer, podcaster and investor. He has written five bestselling books, been an early-stage investor in Facebook, Uber, Shopify and other household names, and is the host of one of the biggest podcasts in the world. He started The Tim Ferriss Show as an experiment in April 2014 and has deconstructed world-class performers ever since. Last year, his show crossed 1 billion downloads. Together, we explore his podcast and approach to life. We talk about the art of interviewing, the business behind his show and what motivates Tim to keep teaching through his writing and podcast. Please enjoy this great conversation with Tim Ferriss.

• 2:05Patrick O'Shaughnessy?

  So Tim, you're coming up on 10 years, billion downloads, all sorts of cool, fun accolades. I would love to begin by asking you, what has changed the most about what you enjoy about the process of learning from other people by getting to ask them questions? It's a very selfish question. I'm just curious how it's unfolded for you. It's something I think about a lot. What has changed the most in the first 10 years of you doing this? And maybe extra points for anything that is most surprising about what's changed in the first 10 years.

• 2:36Speaker 02

  Well, I would say there are a number of phase shifts in the last 10 years. It started off as purely an exercise for me to try something fun in 2014 that would also allow me to win even if it failed. What I mean by that is I wanted to ask myself, what skills could I develop or deepen? What relationships could I develop or deepen that would make it worth it even if I stopped doing the podcast after six episodes? And I think my initial commitment, public commitment was something along the lines of six to 10 episodes. And that gave me the option of a graceful exit if I wanted to stop doing it. That was never intended to be a business.

• 3:18Speaker 02

  Podcasting as a business wasn't really a thing at that point, at least not in any meaningful way.

• 3:22Patrick O'Shaughnessy?

  Podcasting wasn't?

• 3:23Speaker 02

  Yeah, yeah, exactly.

• 3:24Patrick O'Shaughnessy?

  There's none of them.

• 3:25Speaker 02

  And I did it to deepen my relationships with my friends because I could do all sorts of Google sleuthing that would be creepy otherwise and make it Charlie Rose for my friends. And also to remove verbal tics and get better at asking questions and follow-up questions and weaving conversations, which is something I was already doing for the nonfiction books. So the way I viewed it was as cross-training for later transfer to my nonfiction book writing and research. That worked, but then podcasts and my podcasts took on a life of their own and then it turned into a business. So I would say for me, in terms of what has changed, the first is that it was a sole

• 4:07Speaker 02

  focus on craft in the beginning, and now there's a business to run and there are business considerations. And it's very easy to get pulled away from and maybe oppose your original reasons for doing something. Once the complexity of capitalism is added to the mix, I'm not saying complexity is a negative thing, but I do think that those incentives can be terrible masters at times and sometimes beneath the level of awareness bend the way that you do things or approach things, what you say yes to, what you say no to. I've developed over time more and more awareness of that type of application running in the background

• 4:51Speaker 02

  so that I can hopefully make choices that are true to the craft and many of my reasons for choosing this medium in the first place. A lot of things have changed in the ecosystem, of course. It is much more saturated now than was the case at any point in the past. It's going to continue to get more saturated because the hurdles are lower and lower and cheaper and cheaper. And I'd say what I get out of it, as you said, it was a selfish question. It's funny to use that word because I often think that the podcast is basically my public exploration of things that interest me. And that could be a problem, that could be a goal, that could be something I'm thinking about doing in six to 12 months. There's perhaps

• 5:33Speaker 02

  an extreme point at which that no longer serves the best interests of the audience, but by and large, number one, I would say, if I don't continue doing the podcast, then it really doesn't serve any interests of the audience because podcast ceases to exist. So even if something is self indulgent, and this is true with my books too, sometimes I write stuff simply because I want to write them. I don't particularly care if any reader reads a given subchapter or something like that, but it's important to keep me going to finish the book. And I would say separately that as long as I remain deeply interested in the person or the subject matter, deeply curious and engaged, my audience seems to

• 6:13Speaker 02

  read that very clearly and borrow that enthusiasm and they'll stick with it. So they're pretty subject agnostic, I would say. What has changed with respect to my audience is that they have a paradox of choice challenge, as we all do. There's just such an overabundance of good, great podcasts, TV shows, films, you name it. There's just too much. You can't physically consume even a tiny fraction of it. So choosing that, I think, has led to some interesting dynamics in listenership and certainly. The bull run, very unexpected massive podcast bull run with influx of capital in 2020,

• 6:53Speaker 02

  2021 especially would not and has not been sustained. So I do think that from a business perspective, a lot of the podcast networks are going to be going into a world of hurt in the next few years. And there'll probably be a lot of consolidation would be my guess. On a personal level, to have started at my kitchen table, some things don't really change. I'm now sitting at my kitchen table. And that's a deliberate choice. It's not accidental that I'm not sitting inside a large fixed studio with a staff of 20. That's not accidental. Those are choices I've made. Sometimes to the detriment of growth, that's a very conscious trade off. But I still love doing it for the reasons that I loved

• 7:36Speaker 02

  in the beginning. I get to explore and I'm going to have these conversations anyway. So I might as well record them and share them, at least for the time being. And I'd say when I have strayed, if I've strayed, it's when I've ended up in this middle ground of author press junkets, because there's so much inbound and some of the guests are very good, where I end up in this soup of 15 other podcasts who are publishing with the same guest in the same week. And I'm going to use the 10th anniversary as a way to set some very strict policies for myself moving forward so that the podcast and I remain a little more focused with some exclusionary criteria so that I continue to enjoy doing the show. Priority number one is I enjoy continuing to do this.

• 8:21Patrick O'Shaughnessy?

  Of the people I know, you're the top of the list of someone that's just constantly trying to figure stuff out. I'm curious if there's a question behind all these questions. What are you trying to figure out in the most basic sense? Is there like a core question that animates your behavior and your curiosities in life? Because you've studied and shared studies about lots of different things over the years in your books, on the podcast, et cetera. Could you narrow it to like a question that your life seems to be attempting to answer?

• 8:53Speaker 02

  If I had to pick something, and this is going to sound pretty highfalutin, but I'll use it anyway. I would save something along the lines of how people find or make meaning. In a world that one could argue is pretty intrinsically meaningless, but full of suffering. So how do you compensate for that? I think you compensate for suffering by having a higher level of meaning. You're not going to remove the suffering, or at least not the pain. So how people then create meaning for themselves, the stories that they author for themselves or borrow from other people or other traditions, those are all incredibly interesting to me. And I think the older I get, the more interesting that specifically becomes.

• 9:35Patrick O'Shaughnessy?

  If you had to think viscerally of who comes to mind when you think of a meaning maker of all the people you've interacted with, is there someone that you think has done just an exceptional job of making meaning in their lives?

• 9:48Speaker 02

  I could probably think of a hundred people, at least from the podcast, because it doesn't need to be abstract. I've never interviewed Jiro of Jiro Dreams of Sushi, but it could just be making the perfect

• 10:02Patrick O'Shaughnessy?

  The world's best sushi.

• 10:03Speaker 02

  The world's best sushi, the world's best Japanese egg. That poor guy had to make eggs for 10 years before he was allowed to touch the sushi rice. It could just be that. That's it, right? Could be, I'm going to write the saddest poetry I can possibly muster to elicit the deepest feelings that people try to suppress so they can feel more expressed, whatever that is, right? It could be anything. And I would say if that is simply, I'm not providing answers that these people gave me, but let's just say you're LeBron James and it's family, community excellence in the game, hypothetically, and it's like, boom, you have that scaffolding and you build off of that.

• 10:44Speaker 02

  And that's how you organize your orientation of the world and make sense of all the ups and downs or weather the ups and downs that come with being human. It really could just be any one of those things. And I would go further to say that the more abstract it gets, the more it sounds good, like something from Deep Thoughts from Jack Handy. Or if it starts to sound like a book you'd find, like the spiritual self-help section, the worse off you're going to be in actuality.

• 11:17Patrick O'Shaughnessy?

  So sushi and egg is maybe a great candidate.

• 11:20Speaker 02

  Yeah, get your feet on the ground to the extent possible. So for myself, and I've seen a lot of guests do this. I've tried to pre-schedule every year buckets of time. Let's just say it could be a long weekend, could be a week, could be a month with activities and groups of people where I know that I will be deeply present, not focused on the normal preoccupations. Archery, for instance, that's something that I've been very focused on in the last little stretch of time. And I love it because you get immediate feedback. If you're distracted, it does not go well. Therefore, I find it very, very grounding.

• 11:59Patrick O'Shaughnessy?

  What role does creating things, or I like the term used, works of imagination? What role does that play in your experience kind of studying this idea of meaning-making in this whole thing? Like LeBron, like obviously he's creating a body of work that's like itself sort of an artwork or something. But what have you learned about the things people make? The literal things that they make, product, works of art, whatever, and the role that that plays in meaning-making?

• 12:26Speaker 02

  Well, I would say broadly speaking, that it doesn't really seem to matter as long as you are making something. As long as you feel like you have a product of some type, not necessarily a commercial product, but just something that wasn't there before that is there now. And that could be a performance that people see, it could be a performance that only you see. It could be Jerry Seinfeld working on his material and developing it from the punishing writing stage all the way through to the final delivery. I think the act of making is a very innate human drive. And much like walking, it's like we're built, we are evolved to walk and make stuff.

• 13:10Speaker 02

  And if you don't do those things, I do think there are problems tend to surface if you don't exercise those things enough. I would say the relationship between making and making meaning, making something just seems to be tightly correlated. The people who make things regularly are either better at making meaning seeming, and that translates into seeming more at ease with themselves in the world, or they are better able to.

• 13:40Speaker 02

  Prevent the existential distress of being human from eating away at them because they keep themselves busy with their hands doing something. I mean, all of the people I would consider having good peace of mind, who are highly functional, are very physically active and very often make something of some type.

• 14:00Patrick O'Shaughnessy?

  During the making of what thing did you personally feel the most alive or aliveness? Like, if you think back on all the stuff you've made, you've made a lot. What made you feel the most alive?

• 14:12Speaker 02

  I would say if we're looking at work product, the podcast, because the podcast to me is, and there are many different ways, as you know, of constructing interviews. The way that I construct interviews is with some scaffolding, but it very often turns into improv jazz, and I like the challenge of that. It's not dissimilar from archery. If I tightly scripted everything, like inside the actor's studio, James Lipton, excellent, incredible, what a corpus of work, and he never deviated from his cards. A stack of blue cards, they were in a particular order. If the guest opened the most interesting side alley opportunity, he would never take it. And he had his script, he followed his script. There is very little in terms of surprise.

• 14:55Speaker 02

  Also, he very frequently knew the answer, or some version of the answer the guest was going to give. I find the improv nature of how I try to conduct interviews to be very similar to playing a tennis match or something along those lines that has a game dynamic and a spontaneity and improv requirement. So I would say the podcast, certainly more than writing. The moments of being in the zone writing are very fleeting for me. It's mostly bricklaying, and it's very challenging, very, very challenging. The moments of being in flow with writing are much harder to engineer, whereas with

• 15:38Speaker 02

  a podcast, with the right vetting, with the right guest, with the right subject matter, being in the proper state myself, if I have my nutrition. Dialed, which doesn't need to be anything fancy, but there are some basic do's and do not do's. Then I could pretty reliably end up in what I would consider a state of flow where there's a certain ego dissolution. It's not like a psychedelic experience, but it's a minimizing of the self that is very relaxing to me. It's very intently focused, but in this case, it's also very relaxing at the same time. So I can do a two and a half, three hour conversation as I did yesterday and feel energized for four or five hours afterwards,

• 16:23Speaker 02

  even though I'm very, very introverted.

• 16:25Patrick O'Shaughnessy?

  Every single person listening would benefit from more engaging conversations in their life, even those that are great at conversation. You've now made a practice of getting better at this and doing a million of them with the most interesting sparring partners. Say a bit about like the ingredients of a great conversation that you think people could actually take away and do something with. There's probably some innate ability, like some people are just better at others at whatever. But what do you think are the ingredients that you've learned to inject or look for in a conversation that you think would be broadly applicable to everyone that's having conversations all the time and would have a better life if their conversations were better?

• 17:02Speaker 02

  For me personally, this is a learned skill. This is a trainable skill. I wouldn't say that this has been my natural default. I'm very introverted, as I said before. One thing you can do is read interviews as much as you listen to them and you'll pick up a bit more of what the interviewer is doing. It's kind of like watching sleight of hand in slow motion. You'll have a better view of things. So when I was starting the podcast, I mentioned James Lipton. I hired one of his former researchers to go through my transcripts with me and show me where I could have improved. Now, if you're just improving your conversational abilities and not doing a podcast, then maybe you don't want to do that. Although my recommendation to everybody listening would be record six to 10 episodes of a podcast. It's so cheap for a hundred bucks.

• 17:47Speaker 02

  You can have a good mic, just get it done and listen to yourself and look at a transcript. And you will notice plenty of things you want to fix. So that would be a very easy recommendation. And if. You wonder what the conversation should be. Interview your parents, do something for posterity. Interview your kids. Interview one of your best friends and have a couple of drinks. Other recommendations would be to ask very basic follow ups. The reason for that is that most humans who interact a lot have set pieces, even if they don't realize they have set pieces. So they're not going to necessarily be working their material like a stand up comic who's prepping for a 60 minute special. They are always working on material as far as I can tell. Dinner is wherever they might be.

• 18:32Speaker 02

  But as anyone with parents, which is all of us can probably attest, some people tend to repeat stories. If somebody, let's just say, is sitting next to you at a small dinner party and they give you some basics, you can ask very simple follow ups. What did you learn from that? Oh, that's really curious. You say more about that. How did that feel? What was the experience like the 24 hours before that? 24 hours after that? Very simple follow up questions as opposed to rapid fire, small talk that you might find if you're on a first date or second date. And then I would also say, let the silence do the work. This was advice that I got from Cal Fussman way back in the day,

• 19:16Speaker 02

  who wrote the What I Learned column for Esquire magazine for ages, interviewed Muhammad Ali, Korba Chaff, you name it. And his feedback to me when he listened to the first handful of my podcasts was let the silence do the work. Give a little bit more space so that it gets a little uncomfortable and people will give you more. Now, you don't want to be a freak show when you're at a cocktail party staring at someone in silence, but don't rush to fill the space. Space is fine. No one's going to get hurt.

• 19:44Patrick O'Shaughnessy?

  What's the most uncomfortable that you ever felt in an interview?

• 19:48Speaker 02

  There have been moments when people have had very emotional experiences. I have a lot of capacity for absorbing that or handling it, but it presents a challenge as an interviewer because it's hard to know what to say in those circumstances. So I've had people come on my podcast and for the first time ever. Talk about childhood sexual abuse they've mentioned to no one, or alcoholism that they have mentioned to no one, and they come from a community and a family who would condemn that. Or they talk about a friend's death that had a tremendous impact on them. And I see them tearing up and I can tell that they were not expecting to talk about it and they were not expecting to tear up.

• 20:34Speaker 02

  So navigating those emotional moments, which I usually just let sit with silence. I don't rush into something. If I get someone who's just a prick, that happens occasionally. Some salty old dog is just beyond difficult. But once again, silence does a lot of work. If they're not letting you get a word in edgewise and you just go dead silent, eventually they'll pause and then you can get a word in. You can also interrupt, but I try to head a lot of that off at the pass with pre-game conversation. So I think the art of the interview starts before the interview. For me, it's making someone as comfortable as possible in the five minutes of pre-talk before hitting record. Making the ground rules clear. You have final cut. This isn't live.

• 21:20Speaker 02

  You'll see a transcript before anything goes out. We can cut anything, so please just be as open and as loose as possible. We can always cut things. We can't add interesting things in. This isn't a gotcha show. My job is to make it look as good as possible.

• 21:35Speaker 02

  And here's what I'm thinking. There's a broad arc of the conversation. Here are the first two things I'm going to ask, just so there are no surprises out of the gate. You can always take a bathroom break, water break. My job is to make this as easy as possible. That first five to 10 minutes is really important before hitting record.

• 21:53Patrick O'Shaughnessy?

  Do you have, after all these years, a favorite question? Like if you had to just start every conversation with a single question, is there an obvious candidate for that?

• 22:04Speaker 02

  I usually try to start the conversation with a question that reflects a deep level of prep and research, especially with people who've been interviewed a lot, because I want them to turn off the autopilot. They may already be on autopilot. Publicist is making them do A, B, and C. And suddenly they're put in front of a microphone. They're like, this is Tim Ferriss, go. And they're already on autopilot to give me their set piece. To try to circumvent that, I mean, one way you do that is by having a podcast that's long enough that you can burn through that material. But the second way is by asking them a question that they're not going to be asked typically. So I might look for a very brief mention of a third grade teacher who had an incredible impact on their life that is glossed

• 22:49Speaker 02

  over as just a passing comment and some type of print interview. And I'll say, tell me about so and so. Right. And they'll go, oh, oh, wow. Okay. Wasn't expecting that as the opener. Although generally I tell them upfront, but I don't always get to do the pre-talk. If somebody's in a rush and they're jumping from gig to gig to gig, or if it just doesn't come together for whatever reason, I will usually use something like that. I will look for the footnotes in Wikipedia that are least likely to have been explored by other journalists and things like that. But if I had to start with something, I would probably ask about mentors, something that would allow us to get into something reasonably quickly, that

• 23:30Speaker 02

  would depersonalize things a little bit. So it's probably not something they have rehearsed a lot. So non-family mentor, or someone who had a big impact, positive or negative, that really shaped them in a way that made them who they are. I'd probably start with a question along those lines, or that wouldn't be a bad candidate.

• 23:48Patrick O'Shaughnessy?

  And like the general category of mentorship, seeing examples of excellence is like such an interesting subcategory there. And if you think about standards of excellence, like someone who themselves held themselves to a very high standard amongst people that you would consider like mentors or quasi mentors, what's an example there? Like, I'm very curious to explore with you, like the standard that you're holding yourself to and what inspired it in the form of another person?

• 24:14Speaker 02

  All of the mentors I would name. I'll give you one, Ed Schau, S-H-A-U. I've actually had him on the podcast. He's in his 80s now, still teaching. Ed is fascinating. He taught at Harvard Business School forever. He was a computer science, one of the very first computer science professors at Stanford. He was a competitive figure skater, I think up to the national level, took a few companies public. He was a congressman in Silicon Valley, the guy's done everything. So first of all, just an amazing character. And inspiring to students, I think in part because he had this Feynman-like diversity of interests.

• 24:55Speaker 02

  And I just saw him again and again and again, go above and beyond with his students and he kept in touch with a lot of students over the years, including me. I mean, he's responsible for my first book, Four Hour Work Week, in the sense that he invited me to come back to speak to the class, High Tech Entrepreneurship. This is ELE 491, way back in the day at Princeton, because everyone else had venture-backed companies who came in to guest speak and he wanted somebody who had bootstrapped. So that was a little on me. And the notes and the prep and everything from all those classes, I went and spoke twice a year for ultimately, I think 13 years, might have been somewhere between 10 to 13 years. Those notes formed the basis for the first book. I owe Ed a lot.

• 25:37Speaker 02

  And he's incredibly good at asking the right probing questions to get his students to think more critically, to think more orthogonally, to just think more incisively versus giving advice. He also gives advice, but he's almost always using the case study method, one way or the other, whether he has a module or not, right? He's like, here's the situation, what would you do? Okay, great. Why would you do that? He's one who comes to mind. Also wrestling coaches that I've had, John Buxton, who was my high school wrestling coach, very tough, very, very, very tough.

• 26:15Speaker 02

  And I would say all of the mentors I can think of, most of the mentors, not all, have a pretty tough love style. I don't think it's possible to reach your potential of excellence in any given field without somebody... There are a few mutants who can do this on their own, but most folks can't really reach beyond what they think is possible unless they're pushed into discomfort. And sometimes you need someone to kick you in the ass and make you do that. You know, I remember training and wrestling with Mr. Buxton, there's a garbage pail in the corner when you had to vomit. He'd make us do these just awful drills, metabolic conditioning drills.

• 26:56Speaker 02

  And I would say that, in addition to many other things, led to a really strong team. And if kids on the team had, say, an academic problem, he would bring them over to his house and he'd be like, you're gonna sit down, you're gonna work on A, B, and C until dinner. Holistically, he was also a very good caregiver and shepherd for his flock of student wrestlers.

• 27:15Patrick O'Shaughnessy?

  Going back to the making instinct of humans, can you compare and contrast the feeling of making the thing with the experience of watching the thing get received? One that comes to mind is the Seinfeld interview, which I thought was one of your best by far and just one of the all-time great interviews. I don't know what happened there, like talk about flow and chemistry and like something that got just kind of unlocked for whatever set of reasons. What would you say is different about being in that versus the feeling of watching it get so positively received? Sort of the participation versus the reward? And I'm curious like how much you think about one versus the other and what governs your behavior?

• 27:51Speaker 02

  I don't think about the reception very much. I know if an episode has the potential to be a blockbuster. And halfway through that episode, I was like, yeah, okay. Now I'm just like, don't, like I'm running towards the

• 28:04Patrick O'Shaughnessy?

  Don't fuck it up.

• 28:04Speaker 02

  Touchdown, do not trip over your shoelaces. Yeah, do not trip over your shoelaces. That's been true for every episode that I know has the potential to do well. Now, they won't always do well, but they have the potential. And I knew with Jerry, people would give it the benefit of the doubt. So I knew in the midst of doing that, that it was gonna be received the way that it was. So I just wanted to enjoy the ride. There are other episodes, though, that don't get the visibility because the name isn't as recognized, like Claire Hughes Johnson, who worked at Stripe and helped build it from a few hundred to 6,000 plus employees. And that episode was so strong and so dense, and it did do well. But because her name is not as recognizable as, say, a Seinfeld, it didn't get the sheer

• 28:47Speaker 02

  volume of people giving it the benefit of the doubt, as I would hope. I mean, she's incredible. That was an episode also that I think had a lot of flow and serendipity and incredibly tactically dense. But the name recognition does matter for a lot of folks. And as things get more and more crowded, I think that is the case, unless you go super niche. So if I were to do this now, because it is so saturated, if I wanted to develop a decently sticky dedicated audience of, let's just say, 100,000 downloads per episode minimum, I wouldn't have the luxury of going as broad as I did, which was deconstructing world-class performers. That was necessary for me to have the endurance and interest to sustain it over time. But I think that if I were to do it now,

• 29:31Speaker 02

  the scope would be much more constrained so that I could find my 1,000 true fans more quickly and reliably. It would just need to be a long tail search term at this point.

• 29:43Patrick O'Shaughnessy?

  What are the most basic ingredients of that question you always ask? Like, the ingredients of world-class performance? Is it lots of recipes? Is it just a couple recipes, you know, expressed lots of different ways? How variant is the story or the scaffolding behind the performance of all these people that you've explored?

• 30:03Speaker 02

  My knee-jerk response, I'd want to really sit on this, but it's quite varied because world-class in one field can require a certain level of capability in being a generalist, let's just say, perhaps as a director, for instance. You might have a lot of camera experience, some experience writing. You've worked to various different stations and that informs your ability to be a really good director. Whereas if you are a pure play athlete, you are highly specialized from a really young age, as would be the case with, say, a Kelly Slater or LeBron James or someone else, Sean White. I think what qualifies as world-class, it does depend a lot on the domain.

• 30:47Speaker 02

  So if you have something like sports or acting, there are many other examples I could give. I'm sure this is true for a lot of investing, depending on which category you choose. You get rewarded for being like top 1%, top 0.01%, right? It is a winners take most type of scenario, which is also true in podcasting from a financial perspective. There are other areas where to be world-class, you actually have to be. More of a Venn diagram where you might be top 20% in a few things that then go together. I think that's true for a lot of tech CEOs who start as a product people or engineers. You see a couple of different overlapping circles where they're top 20.

• 31:31Speaker 02

  They're not necessarily the best of the best, the LeBron jams of any one of those three. But when those three are combined, they end up being sort of a category of one, so to speak. It's very different. I'm particularly interested in people who seem to achieve some kind of excellence in a field that is secondary to what they first explored or who hit their escape velocity later in life. It's harder to find, frankly. I'm increasingly interested in those folks.

• 32:00Patrick O'Shaughnessy?

  Because you think that their performance in a second domain proves that it's not just like a genetic advantage or something?

• 32:06Speaker 02

  That's part of it.

• 32:07Patrick O'Shaughnessy?

  There's something that can be done about it?

• 32:09Speaker 02

  Yeah, it's more of a training versus attributes in a sense. But a lot of these genesis stories of so and so didn't, you know, Colonel Sanders didn't start Kentucky Fried Chicken until he was 58. When you really dig into these stories, it's not quite so simple.

• 32:23Patrick O'Shaughnessy?

  What do you think about the business of media? Like, obviously, you've been very successful in media, but it's certainly like a power law game like so many other things. And not that many people can do what you've done or what a handful of other people have pulled off. What are your reflections 15 years into writing and publishing so many things? And having a business that's built around those things on whether or not it is or can be a good business? Cautionary points or lessons, encouraging points or lessons? It seems like everyone has some of this impulse because the frictions are so low to publish stuff. Like, everyone kind of likes the idea of having, whatever, a media business, a podcast, a this, a that. What have you learned about the actual realities of business around media?

• 33:09Speaker 02

  I think making something a business is a great way to hate that thing if you don't budget for that. In the sense that if you surf to relax on Saturday mornings, that's very different from being required to show up at the break of dawn to take cantankerous eye bankers out to their first surfing lesson or whatever. That's a different experience. And a few weeks into it, you could decide you don't really like surfing so much anymore. That's number one. Number two is in terms of lessons learned, I really designed this operation from the outset to have constraints within which it had to operate. In other words, I didn't want to have more than a few employees and that constraint would then dictate

• 33:54Speaker 02

  a lot of the policies. So as an example, when I started, there's so much dogma everywhere. It gets cobbled together very, very quickly. In retrospect, it's even more hilarious. 2014, everyone's telling me the rules. These are the rules you have to follow if you want a podcast successfully. What? You're like stressed out. Any of them, they just fall apart. But I have never offered payment terms, as an example, to sponsors. If you want to pay for the podcast, you have to pay upfront. That's it. That's the only way you secure spots. Never offered net 30, net 60, net anything. That has been predominantly a function of admin overhead, just back office headache. I wanted to remove as much of that as possible.

• 34:38Speaker 02

  So people prepay. No one that I talked to was doing that and most don't do that today. But if you want to be on my show, fortunately, we have more demand than supply. If you want to sponsor the show, those are the rules. Separately, the CPMs for my show, at least at the time, I want to say the CPMs for NPR and so on are like $10 or $12 CPM. I think my podcast is right now $60 CPM. It's very expensive. As podcasts go, now I've since changed my approach a little bit because I'm going to be offering partnerships across all of my platforms that I think move the needle, like the newsletter, the blog, which people forget the blog was the connective tissue that allowed the books to provide

• 35:23Speaker 02

  me with direct contact with my audience, which then allowed the podcasts to launch the way that it did. It's easy to forget that I have a thousand blog posts, tim.blog.

• 35:35Speaker 02

  But zooming out to the macro for a second, my ideal is a sponsor who sticks around for five, six, seven, eight, 10 years. I want them to do really well. It's also less work for my team to minimize the churn of sponsors, which is why I'd say one out of 20 sponsors makes it in terms of inbound sponsorships, because we're going to test everything. We're going to survey my audience. I'm going to have my employees test everything. And if it's not, how strongly would you recommend this to a friend from one to 10, no seven allowed? If it's not an eight, nine, or 10, it doesn't make the cut. And once that's done, though, you can run into a situation, for instance, where the ad read is great, the product is great, but their funnel, their website, and their sales flow, their onboarding,

• 36:19Speaker 02

  whatever it is, checkout process sucks so badly that there's all this slippage, and then they could come back to you and say the podcast didn't work, when in fact, we sent them a ton of traffic, but they didn't capture it effectively. So I will also look at their flow, have my team look at their flow, and then help to fix their capture process, so that I can improve the likelihood of them being retained as a sponsor, because they'll see the ROI. The business, I would say, is, for me, an exercise in resisting temptation to diversify. What I mean by that is, the sponsorship model works. It works

• 37:02Speaker 02

  very well. It's straightforward. We have it incredibly streamlined. There is demand. It works. There are alternate opportunities, and you see people taking various approaches to this, where you might have something behind a paywall, like a Patreon, or through an app. You might have products that are in-house products. There are some compelling reasons to do something like this, but with a course, or a membership platform, beverage, you name it, it could be anything. And then, of course, there's YouTube game, but I don't really participate in the monetizing side of YouTube. It's not significant enough for me to pay attention to it at this point. So I don't really pay attention to that.

• 37:43Speaker 02

  What I will say is that from an analytics perspective, it would be very helpful for me to have an in-house product because then I could see from enthusiasm to intent to click through to conversion, how my audience behaves. And that would also keep my team quite happy and interested if they're able to engage with some of those metrics.

• 38:04Patrick O'Shaughnessy?

  Why don't you have one?

• 38:06Speaker 02

  I haven't found the right fit. I mean, I've had 101 things pitched to me. I've considered 101 things and I just haven't hit on the recipe that feels like it's sufficiently energy in versus energy out. A lot of the options I just mentioned would be over time, if you just look at like the mental, not just the capital carrying costs, but like the mental carrying costs would just be too expensive. They're not worth the kind of marginal upside for me. So it would have to be something that I am incredibly, incredibly stoked about.

• 38:41Patrick O'Shaughnessy?

  Do you feel like that's a trade-off where, again, just kind of reading between the lines from what I can see publicly, like it seems as though some major part of your business and financial success is certainly equity owned in what have turned out to be incredible businesses like Shopify, like Uber, like Duolingo, you know, I'm sure there's many more. Would the perfect model be you just did whatever you want, like the value creation was, people seem to want to tag along to your curiosities and you do an awesome job of curating those things and teaching people about those things in a couple of different methods. And then you own equity and stuff and that's the whole business. Like, is that the platonic ideal of the business model because of how powerful it can be when it

• 39:24Patrick O'Shaughnessy?

  goes well, like it did for you with Uber and some of these other businesses?

• 39:28Speaker 02

  It could work out that way. I've thought about moving from, say, sponsorship to a more hybrid model in the sense that I have startups I'm promoting, that I have a large equity stake in. And I'd be open to that, but given how I have invested in the past with startups, which tends to be very early stage, most of those are going to turn into fatalities. So with the inventory that I have on the podcast, I would have to pick and choose very carefully on some level, who and what I promote. And I still do a fair amount of angel investing. I'm not as prolific as I once was. I mean, it's quite a thing to be starting your angel investing at the right time. 2008 was a great time to start

• 40:10Speaker 02

  angel investing, very uncrowded. I will say that pretty good at finding uncrowded playing fields. And that was true with angel investing when I started in the valley, certainly. You didn't really have micro VCs. You didn't have like the Tiger Global starting to come down and invest in earlier rounds. You didn't have that type of bottom up and top down pressure and saturation. And as soon as that started to happen, then I stepped out in 2015 or so. Once the term sheets and so on started looking pretty nutty to me, I stopped for quite a while. And not coincidentally, that is when I started focusing on the podcast, 2014, 2015. And so I'm looking for that next. But I could see there being

• 40:52Speaker 02

  a time, certainly, when I'm promoting startups in which I own some equity on the podcast. That would make sense. There are also, now I would just want to balance the cash requirements of the business because I have employees and so on, right? And we have ad spend and various things that we need to cover with the long-term bets. Since in my case, if I'm investing, when I tend to invest, right? I was also the first advisor to clear the biometrics. Oh, wow. Cool, cool business. Yeah, really cool business. So they've executed incredibly well. Those take a long time. I mean, most of these startups, you mentioned Shopify became an advisor and they had eight employees, maybe eight to 12 employees. And that's a seven to 12 year journey. And

• 41:37Speaker 02

  Duolingo, same thing. It's a long road. So I would just need to balance some of the cash requirements of the business with the long-term bets. I'm sure there's a way to do it.

• 41:47Patrick O'Shaughnessy?

  What's behind your ability to find the uncrowded emerging spaces? It does seem like you've done like

• 41:54Speaker 02

  Yeah.

• 41:55Patrick O'Shaughnessy?

  A certain number of times you start to not think this is luck and there's something else going on. Like it does seem like you showed up early or at a good time in a couple emergent secular trends. So what do those spaces feel like? Like what does angel investing in 08? What does podcasting in 2014? What does blogs and whatever year? What is like the feeling of those things when you've been in them?

• 42:16Speaker 02

  Well, first, how do I identify them? So identifying them, I think, comes from a few different angles. And people may have heard some of these, but they're worth repeating. One is like, what are the nerds doing on the weekend? What are the best in certain subcultures doing on the weekends with their free time? What's happening there? I think you can spot a lot. The second would be, I'm always looking for uncrowded channels for, say, promotion. And sometimes that overlaps with all sorts of opportunities. So give you an example, in the case of podcasting, I came across podcasting because for every book I launch, I look for the under-crowded, undervalued promotional platform or channel. The process is very simple.

• 43:01Speaker 02

  I talked to a handful of friends or I reach out to strangers who have launched books in the last 12 months that have become massive bestsellers. And I asked them, what performed much better than you expected in terms of driving book sales? What performed worse? What do you think is getting more important with time? What is getting less important? And for our work week, the answer was blogs in terms of what was really delivering above its weight class. Yet publishers paid almost no attention to. I was like, okay, that sounds like a good combination. And that ended up driving blogs ended up driving for our work week. For the for our chef, my third book, the answer came back podcasts, absolutely 100% podcasts.

• 43:40Speaker 02

  And so the foundation of my entire launch plan for that book was podcasting. Meaning as a guest, appearing as a guest. And then I got a taste of it and I looked at it and I really got front row seats to how engaged these audiences were. And I thought to myself, okay, this is kind of a no brainer. Once you have broader smartphone adoption, once you have broadband adoption and availability.

• 44:12Speaker 02

  In every nook and cranny of the world, it's almost a foregone conclusion that as a secondary activity, audio on these devices is going to be huge. And you look at the diehard behaviors of some of these crowds who were followers of each of these podcasts, I'm like, okay, this has all the ingredients of something that's going to go completely ballistic. So let me start to dabble, roll up my sleeves and play around with it. And I think that in 2008 with startup investing, that was, that was, I would say responding to doors that opened as much as anything else. As a byproduct of the launch strategy for the four hour work week. So there's an expression, I can't recall who first said it, I certainly did not originate

• 44:56Speaker 02

  it, but the target is not the market. Meaning my target for the initial launch of the four hour work week was, let's say, 20 to 35 year old tech savvy males in San Francisco, New York. Those were the target. That doesn't mean it's the entire market, of course, but I wanted to hit a core audience of people online who had the ability to propagate and promote something widely. So I focused on, let's just take San Francisco as an example, and I asked myself, okay, well, fortunately I'm in that demographic, so I have some idea of what they do day to day. What are the main outlets? How could I achieve a surround sound effect where I look ubiquitous for a short period of time?

• 45:40Speaker 02

  Okay, TechCrunch, Gizmodo, Lifehacker, a handful of sites. If I'm on all of those in the same two weeks, I will appear to this target group like I am everywhere. So I took that approach. That got me in front of a lot of people in tech. It had the desired effect. Then it leapt across the country geographically to New York, then it expanded to women in the same psychographic, and then it expanded in various directions from there. What that did by getting me in front of tech folks is gave them a familiarity with me and founders started to reach out to me for various reasons. Simultaneously, I was helping a friend of mine, Mike Maples Jr. at the time.

• 46:22Speaker 02

  Now Floodgate. At the time was an angel slash kind of micro VC. I think he was still an angel and I was helping him with some exercise programming. We met at Hobie's and I would help him with various questions around the fitness stuff and also marketing and launches because my book had just exploded. And the exchange was I would ask him to tell me how he had chosen different deals and explain deal structure and so on related to angel investments. And I'd been fantasizing about going to Stanford Business School. I think this was like my third time of bringing this fantasy to the forefront and I would audit some classes and I'd get excited, but then I'd be in a bunch of theory and I'd find it boring as hell. And I realized, huh, I could just run an experiment and I

• 47:07Speaker 02

  run most of my life as an ongoing series of experiments. I could just make a real world MBA where I take what I would have spent $60,000 a year at the time at Stanford, okay, 120K, and let me budget that for my real world MBA and I'll use it for angel investing. If I can get some help along the way. So I kind of saw the access that I had through the book. I had the opportunity by meeting Mike Maples and spending time with him and then asked if he would be open to me co-investing with him on a very small fry basis, being like the smallest player on the cap table and then really over-delivering for a handful of startups to get referrals, diehard supporters, and then kind of letting it go from there. But I was familiar enough through just talking to Mike and others with

• 47:52Speaker 02

  the dynamics of the ecosystem and where some of the gaps were. So at that time, there were only a few people, very few, two or three who are known who are doing well as advisors to startups, taking advisor equity. And there were a few, and I really mean a few, maybe six to eight angels who were reasonably well-known as angels, you know, Ron Conway and so on. And then you had this huge gap up to the blue chips and there was a lot of space in between and I thought there was room for me as someone with audience to come in and materially increase the value of certain types of companies since I had access to this large

• 48:32Speaker 02

  audience after the first book and that's how it started. That was more of a response to a lot of the inbound that I received after the first book.

• 48:45Patrick O'Shaughnessy?

  What have you learned about working well with a really small team? I've interacted a little bit with your team and I've just really enjoyed it and found the people to be super curious and low key and I'm curious what you've learned in the however long you've been doing it. Seems like you've always kind of had a small team and that's a deliberate choice that you've made. What are the things you've learned about really good working relationships with a very small team, even when the reach and the impact is large?

• 49:12Speaker 02

  First and foremost, I should say that I don't think I am a great manager. I don't think that is one of my superpowers. I think I'm a very good leader, but I don't think management per se is my superpower, which means I need folks who are very self-organizing. I can help them with priorities and high-level objectives and trying to keep things on track on a quarterly basis, et cetera. But a few things come to mind. The first is really trying to connect everyone to what impact the collective effort is having in the world is really important, right? Because they might work on A, B, and C, all sorts of things behind the scenes, kind of make the cars that get shipped out and then they don't get to see the car winning

• 49:52Speaker 02

  the F1, you know? So constantly trying to bring examples in of impact on real people in the world so that they are reminded, and it's to remind myself as much as anyone else, why I am doing and why we are doing what we are doing. That I think is very critical. Because with a small team, especially a distributed team, it is easy for people, I think, to potentially feel isolated. My entire team is distributed. And there are, I think, many things that Tim of 15 years ago would have deemed really inefficient and therefore unimportant, like weekly team calls where we don't talk about business or we do like a team huddle on like one thing you're happy about and one thing you're

• 50:36Speaker 02

  proud of from this last week and things like that, that I would have, would have just made me squirm and scrunch my face 15 years ago are actually really important. Occasional offsites and so on. I don't think I'm the best person to opine on management, but I will say that I recognize that management is not my superpower and therefore I have created constraints that force me to operate within my zone of competency, which is very small team.

• 51:05Patrick O'Shaughnessy?

  Say more about what makes a great constraint. It seems like that is the real insight is that constraints are powerful and maybe underestimated. So how have you gotten better at designing and implementing constraints? What's the anatomy of a great constraint?

• 51:21Speaker 02

  The anatomy of a great constraint is trying a bunch of different constraints and considering, you know, what if I did the opposite of X? If everyone's telling me I need to do X, what if I did the opposite of X, negative X for two weeks, for instance?

• 51:33Patrick O'Shaughnessy?

  Like George and Seinfeld.

• 51:35Speaker 02

  Exactly. Yeah. Like George's, like George and Seinfeld. Yeah, exactly.

• 51:38Patrick O'Shaughnessy?

  The straw me on ride.

• 51:39Speaker 02

  Yeah. Yeah, exactly. Exactly. So for instance, the Kestrel principle. So for instance, algorithmically and platform wise, almost everything's pushing to video. So people are building out TV studios. That's fine. It is antithetical to my reasons for beginning podcasting and embracing this medium in the first place. So what if I began doing walk and talks, which is what I use this headset for, where I go out, I'm getting exercise, having a conversation with a good friend and we record it as is, and then we put that up. It is the anti-video. And I feel better doing it so far. Every conversation I've loved doing how my audience responds TBD, but a lot of my audience has really appreciated it. So they're like,

• 52:24Speaker 02

  you know what? You're right. We do sit in front of screens way too much. Thank you. So I'm encouraging my listeners to also get out and walk when they listen to these things. That would be an example. Now, whether that works, what does working even look like? I know that that is going to be more energy in for me than energy out. So I'm happy to test it simply on that basis. And if it does not perform significantly worse than the alternative, I'll keep doing it, at least with some frequency. Could be a two week experiment, could be a two month experiment, but the constraints that I find most interesting are constraints that force you to do something very differently from how most people do it. So could be a constraint of subtraction. Like, what if you couldn't use your phone

• 53:06Speaker 02

  for a week? What if you could not use this for a week? What would that look like? In October, I went two or three weeks without a phone. I do a lot of experiments like that. And we frequently figure things out that save us a lot of work or point out that 20% of what we're doing, we don't need to do it all in the first place. And I like that. I enjoy that type of experimentation.

• 53:28Patrick O'Shaughnessy?

  Not to ask nine questions at once, but I really would love to hear you pick any combination that's interesting to you of the good, the bad, and the ugly of money, power, and fame. In many ways, it was you that convinced me, one of the amazing reasons we don't do video, and I took my picture of everything, and was that post you wrote about fame, that look, fame's appealing in some ways, but it's not a universal good. And it's cool because you're an experimenter. You've experienced money, power, fame in different forms over a period of time. And I love the good, bad, ugly framework. I'll let you answer any part of that you want, but I'm super curious for you to riff on any parts that you think are the most interesting.

• 54:07Speaker 02

  I would love to know how some of your other guests have responded to this in a way that has stuck with you. The post, if people are interested, I would recommend a lot of folks, everybody should read it. It's not too long a read, but 11 Reasons Not to Become Famous. If you want to see what the reality looks like, and by the way, micro-famous still means famous to a small subset of people, and you're going to see the same types of effects and side effects that I talk about in this particular post. If you have kids, you should also look at it because if kids are being effectively raised on social media, many of the landmines and risk factors are going to apply. So fame, I would say, almost entirely corrosive. I see no upside other than maybe getting a slightly better table

• 54:50Speaker 02

  at a restaurant. Access, there is a certain degree of access that you're granted if you have fame, but you can get that if you have sufficient power of money as well. And I think those are, I don't want to say cleaner, but they have a more favorable side effect profile. And by fame, I also mean just broad facial recognition. Name recognition, not as bad. In fact, really all the upside of fame that I can think of comes from name recognition and not facial recognition. Yeah, I would highly discourage, which is another reason why I have throttled back a lot of my video activity. And this is a, sometimes a challenging conversation

• 55:35Speaker 02

  to have with my team because they like to see the podcast grow, they like to see big numbers. And podcasts have a severe discovery problem. YouTube solves that, in a sense, although it turns into clickbait heaven. It's kind of a disaster. Like, everything is the New York Post. It's very dystopian. It's pretty bad. All right, just like peg it geographically. Fame, that's like LA. And then you have money, that's New York. And then you have power, that's DC. That's kind of how I would think about it. And power, well, let's talk about DC for a second. So I had a mentor who had a lot of experience in all three of these say to me at one point, he said, yeah, DC is just like Hollywood, but with uglier people.

• 56:18Speaker 02

  So I do think that power can be really corrosive. I don't have as much experience with this outside of the context of audience. I can bend the arc of a lot of things with a large audience. I would say my experience is that people who are really, really driven by fame often house a lot of neuroses and kind of mental health disorders, but it comes from a place of insecurity, not always. And then on the power side, you run into more genuine sociopaths. That'd be true for money, too. I would say that on the money side, a lot of people who are really dedicated to money and pursue that to the exclusion of many other things are also using it as a proxy for power, if that makes sense.

• 57:03Speaker 02

  Yeah, money for me, I would say, is fantastic fuel, if you can use it in the right ways, if you can be a good shepherd of that capital. I think the book Die With Zero has some interesting points, Bill Perkins. I think that's worth reading. I don't plan to be the richest corpse in the graveyard. And I think, seems to me, if you give more than, I don't know, 20 million bucks to your kids, you ruin them, basically, from what I can tell. There are a few outliers here and there. So when I break that down, I would say that I think of money as stored potential energy. So I think of how to convert that into something more interesting. I don't

• 57:44Speaker 02

  have a very high burn lifestyle, but I have put, I don't know, 10 to, depending on the point in time that we're talking about, but if you took a blended average, 10 to 20% of my net worth into my foundation, like, that's been deployed. It's not just holding it as a tax play. This is money that's all been granted out, it's gone. And I feel really good about that because of the impact that can be measured with the types of things that I've funded. I would say that this is an ongoing challenge, because money is so quantifiable, it's such an easy way to gamify your life, that it's incredibly tempting to revert to that when you don't have something that is easily measurable, that isn't as discreet.

• 58:28Speaker 02

  I definitely end up here. Every once in a while, I'll be like thinking about the podcast and we can do A, B, and C, and D, and F, and spending all this energy on it. I'm just like, it doesn't make any difference to me in terms of my quality of life. But it's seductive as a sport. I get it. And I will say that you're not going to be surprised by this. I don't think anybody in your audience is going to be surprised. But I know more people who have $500 million who seem miserable than people who have $500,000.

• 58:56Speaker 02

  And I think part of it is that fame, power, money, they're all amplifiers, just like alcohol, let's just say. Like if someone's a raging asshole on alcohol, it's not that aspect of their personality doesn't exist. It's that it gets liberated by the catalyst of alcohol. And money, power, and fame are very similar. They're amplifiers. So if you have insecurities, fears, paranoia, those are all going to get amplified by any one of these three. How do you think about these things?

• 59:26Patrick O'Shaughnessy?

  I think Kevin Kelly is the best in the world at this because he's so succinct about it, which is like, I'll butcher the exact line, but something like, you should seek fame amongst the group of those people you respect. And you should try incredibly hard to never have a billion dollars.

• 59:44Patrick O'Shaughnessy?

  He's like, everyone I've ever met that has a billion dollars is the worst. So if you're coming up against that, just get creative and make sure it never gets to that number.

• 59:55Patrick O'Shaughnessy?

  Which I thought was very, very funny and very him. I agree with everything you said. I love your comment on name recognition versus visual recognition. Like, that's a great, great, simple heuristic or something. I think so much of the challenges, these things are all stand-ins. They're all terrible objective functions or things to optimize for. You can kind of feel and touch them and it's harder to quantify, like, am I doing great work by some other metric? That is subjective or other people can't validate, or it's not something I can point to. So there's tremendous insecurity that gets wrapped up in it all. And what I've loved about watching your trajectory is it just seems like you give such a shit about the things you're putting out. I was going to ask about marketing next. I just saw your thing with Seth, Walk and Talk with Seth Godin, who I think is

• 1:00:37Patrick O'Shaughnessy?

  Such an interesting guy, but this notion of caring that you've got something you're interested in, you do the work to learn about it, to distill it down, to package it in a certain phrase, or sentence, or title, or whatever. And then you are thoughtful, like you talked about earlier about distribution channels and way to disseminate those packets of information. All of that is not as simple as like, I have this many dollars. To do all of that well is the impressive thing to me about you. But how do I say that? It's actually much easier for me to be like, well, he made all this money in Uber and Shopify.

• 1:01:11Patrick O'Shaughnessy?

  But that's not the impressive thing. Like, that's the thing that happened that happened to be like a commonly accepted yardstick. But the impressive thing is this guy goes out. He's curious about stuff at frontiers. He figures it out. He packages it up. He serves it back to me in the places where I exist. That's the motion that's impressive, but that doesn't really roll off the tongue.

• 1:01:31Speaker 02

  Doesn't roll off the tongue, yeah. I struggle with this. If it makes feeling better, I struggle with this. People are like, what do you do? I'm like, that's a damn good question. What the hell do I do? I think of myself as a teacher first and foremost. A teacher slash participatory journalist. I have had my life shaped so incredibly and pointed in the right direction, where it could have ended very badly otherwise, by teachers. I, for a very long time, thought I was going to go back and become a ninth or 10th grade teacher, specifically because it seems like kids, especially in ninth grade, that kind of have many branches in the tree, many different decisions they can make.

• 1:02:15Speaker 02

  And some of them take them in a very good direction and others take them in a very bad direction. I saw that certainly amongst my friends. Best friend growing up died of a fentanyl overdose. A number of them committed suicide, lots of drug issues on Long Island when I was growing up. And I managed to get out of there due to a number of really good influences, including a few teachers. So I always thought I would go back and teach. And if I have a superpower, I would say. What comes to mind is I'm a very fast learner. I have an approach to it. It's in that meta learning section in the four hour shop. I break it down, but I have a framework for doing that. I'm a very, very fast learner.

• 1:02:57Speaker 02

  However, once I learn something, I can get someone to that same point in probably half the time. I'm a very fast, I think, very good learner. I'm a much better teacher. Whatever I have learned, then I can strip out the dross, streamline things, repackage it so that I'm teaching it the way I wished I had received it. And I can do that in different formats. I can do that via podcast. I can do that via book. I can do that via anything imaginable, television. Podcasts are great, but they have a pretty rapid decay rate compared to something like a book. For that reason, I think I will continue to write.

• 1:03:39Speaker 02

  And there's a good chance that I'll return to more writing as opposed to seeking out something brand new. See where that takes me.

• 1:03:45Patrick O'Shaughnessy?

  I'm really curious about like much higher compression rates, which is kind of what you're saying. Okay, a podcast takes not that long to record. It doesn't take people that much longer to listen to this than it took us to record it. What would like a 500 to one compression ratio be like? Like you learn for 500 hours and give me something I can consume in an hour. Like Robert Carroll, maybe the master of spend his whole life studying one fricking guy that you can read about in a week or two is pretty wild. I'm curious in what ways you feel like you can get even better in these two things than you already are. Like, as you think about the next 10 years of getting yet better at learning, but then doubly as good at teaching. Where do you feel like you still have the most room for improvement in that skill?

• 1:04:30Speaker 02

  I think I need to have some kids. Frankly, I think that's the next big adventure. Cause I'll just have a chance to do it constantly. So that is not a facetious answer. I think that's the next big adventure. I need to figure out some prelims. As you know, we don't need to get into the specifics, but got out of a very long relationship just a year and a half or so ago.

• 1:04:50Patrick O'Shaughnessy?

  If you had to condense down that meta learning chapter, what do you think the key framework is?

• 1:04:55Speaker 02

  I can explain it. I'm happy to explain it. I use it all the time for everything imaginable. The process is as follows.

• 1:05:03Speaker 02

  You can abbreviate the framework as D I S S S. The I is omitted, it's just to make a vowel in there. D is deconstruct. Then you have selection. Then you have sequencing. Then you have stakes. There are ways that all of these can be used independently, but I like to use them in the sequence. So deconstruct simply means you're taking learn X, learn tennis, learn Japanese, learn archery, learn tango, whatever it is. And you're breaking it down with the help of experts, hopefully, into some constituent parts. Then you have selection. Let's just say in the case of any of these things, you're doing an 80/20 analysis.

• 1:05:47Speaker 02

  If I could only choose 20% of each of these categories or 20% of the categories. And this is, let's just say for the first month of practice, what should I focus on? Okay, great. Talk to some experts and you'll be able to figure that out. And this is very important because selection, for instance, with vocabulary for languages. English has, how many words? 300,000, 400,000, has a lot of words. English has very high volume of words compared to many different languages. But if you take something like Japanese, I speak Japanese, Spanish and a couple others. You can, with say 1,500 words, be conversationally fluent and able to read most things in terms of frequency of appearance.

• 1:06:30Speaker 02

  So you want to select your material first and then your method. The material beats method every time. So material over method is another principle. Put another way, what you do matters more than how you do it. I think that's something people would find most shocking about me. If they were to observe me for a day, they'd be like, this guy gets nothing done most days. But the things I get done tend to be very high leverage or a lead domino that knocks over other dominos. So I choose the things I do very well. As for method, I'm often a sloppy mess, if I'm honest. Then sequencing, this is putting things in a logical order so that you are learning in the proper order. For instance, I didn't learn to swim until I was in my 30s.

• 1:07:13Speaker 02

  And I grew up on Long Island, keep in mind. I had a couple of near drowning experiences and I was, I just swore off water, basically. And nothing worked. None of the coaching sessions, training sessions, teachers I tried worked, until I found something called total immersion. And total immersion exemplifies this process brilliantly. Total immersion swimming basically has you practice hydrodynamic positions before you ever practice breathing or strokes. So you're kicking off the side of the pool in the shallow end, so you can just stand up, experimenting with being in like fuselage right position, fuselage left position, getting your body in the proper position so that you're not wasting 90% of your energy trying to propel yourself on top of the water, all of which is wrong for most people.

• 1:07:58Speaker 02

  So the sequencing, putting things in a logical sequence is really, really key. And you can get expert help. You can experiment. You can try to do things out of order if you want a competitive advantage. I've done that before with selection, for instance, for purposes of Tango. Like I ended up setting a world record in Tango and going to the world championships and stuff in 2004, 2005 because I looked at what teachers were teaching, what they claimed was important. And then I reviewed competition footage and looked at sort of the characteristic techniques and patterns and so on of the dancers I thought I could emulate. And there was this huge discrepancy between what was being taught and what was actually being performed in competition. And so I just honed in on selecting certain things to emulate in teachers who had similar body types.

• 1:08:43Patrick O'Shaughnessy?

  You would have been a good quant investor.

• 1:08:46Patrick O'Shaughnessy?

  You're basically describing good quants.

• 1:08:48Speaker 02

  Yeah. And so I, you know, I had this handheld. This is before smartphones. I would review and categorize all my footage at night. It was very involved, but that was with primarily deconstruction and selection in that Tango example. Then the sequencing, logical sequence. A lot of folks who think that they're bad at languages, you're not bad at languages. It's just that you've never had someone do this. Run the language through these filters properly. Stakes, there must be a consequence, positive or negative, for hitting your goal and not hitting your goal. And it needs to be really compelling. And if you do that, a lot of these other things fall in line.

• 1:09:20Patrick O'Shaughnessy?

  So if you've gotten good at this process, which is so interesting and compelling, what is the equivalent process of being so good at then repackaging and teaching it faster than you learned it? Is it just a better appreciation of that same process and a better framing of that same process to others and a better Pareto understanding or something like that that helps you do that so effectively? Is it clever copy? Is it clever framing? Like, what is it that unlocks such good teaching for yourself or others?

• 1:09:46Speaker 02

  Let's just assume I have a student in front of me. There are really two things I can teach. One is a given subject matter. Tango, charcoal drawing, whatever it might be. I would use this process or the output of this process to teach them and then probably set up some stakes. And then the second thing I can teach, so there's the subject, or I can teach meta learning. Learning how to learn, in which case I would walk them through this process and give them examples, just like I'm doing with you. And then I would have them test it. I would give them projects. I'd be like, okay, this week you're learning this. Next week you're learning this. Week after you're learning this. If you know how to apply this now, holy shit, man.

• 1:10:26Speaker 02

  With ChatGPT and other tools at your disposal, perplexity is really good.

• 1:10:32Patrick O'Shaughnessy?

  Have you tried that? Have you tried to say like, this is the way I like to learn. Here's my method. Give me the deconstruction. Give me the Pareto distribution of what matters. Have you tried using assistants to do this faster?

• 1:10:42Speaker 02

  Yeah, you have to get really good with the spellcasting with prompts to make it conform to this because because the machines aren't going to necessarily understand the terminologies I'm using them. But I know people who have learned to code, video edit in next to no time using just ChatGPT. All of that is going to 10x in the next six months and then the next six months.

• 1:11:07Patrick O'Shaughnessy?

  Do you feel 10 years in like you're at any sort of crossroads?

• 1:11:10Speaker 02

  Oh, for sure. I'll tell you something that I haven't really talked about publicly. I actually crossed a billion downloads last year, like middle of last year. So I've crossed a billion downloads. That was a big milestone. Haven't celebrated it yet. I'm going to celebrate that at the same time as the 10th anniversary. And this is the longest I've ever done anything consistently that still resembles what it looked like in the beginning. I love doing it. I'm going to have these kind of conversations anyway. I expect I'll continue to do it, but I'm not playing the game as the platforms are incentivizing the players to play the game. Which means I do think that I'm going to have to stress test my motivations very carefully

• 1:11:51Speaker 02

  because the decisions that I'm inclined to make to protect the foundational reasons for starting a podcast will compromise my growth, which will compromise the business in some way. And I'm okay with that. So it is a crossroads for me to think about what the next big set of experiments might be. I could see it being something in screenplays and television or film, but I don't really want to deal with the machines of Los Angeles very much. Who knows, it might be some indie self-finance stuff. I'm fine with that. TBD, still very interested in graphic novels. I wanted to be a comic book illustrator for a long time when I was a kid.

• 1:12:26Patrick O'Shaughnessy?

  Retrospective on everything, not just podcasting, but all the teaching that you've put out in all its forms into the world. Is there anything that stands out that you're most proud of having created, looking back on it all?

• 1:12:36Speaker 02

  Yeah, these are not light topics, but I did a blog post called Some Practical Thoughts on Suicide, because I almost offed myself in college. And I know that post has saved hundreds of lives. I feel very good about that. It's also SEO'd very cleverly so that people come across it when they may be considering doing something bad to themselves. And that was very uncomfortable to put out because my family didn't know about it. Then, secondly, I suppose on a similar vein of sorts, I did a podcast, if you go to tim.blog/trauma, it's about as fun as it sounds. The episode, I put it out September 2020, My Healing Journey

• 1:13:17Speaker 02

  After Childhood Abuse. So this is a conversation with a friend of mine about being sexually abused as a kid, from two to four or so, two to five, maybe. And that was very challenging for me to put together, very challenging for me to put out. I was planning on putting it in a book after my parents passed because I didn't want them to blame themselves. And it's 2020, COVID has hit, people are dying, and my girlfriend at the time, who I really owe debt of gratitude on many levels, but for this as well, which was a conversation we had over dinner. And she said to me, have you ever thought about how many people are going to die or take their own lives?

• 1:13:57Speaker 02

  Before you have a chance to put this book into the world. And I thought about it. I was like, you know what? You're right. And it's middle of COVID, uncertainty abounds. So I decided to record this. Took months for me to get there. As a conversation with a friend of mine named Debbie Millman, who was actually the guest who spoke about her own childhood abuse for the first time on my podcast. We had it as a conversation and then talked about our respective paths, the resources and tools we had found individually really helpful. And our paths were completely different. Our approaches were completely, completely different. And I know that episode has had, I mean, I still get

• 1:14:40Speaker 02

  weekly letters from people related to that podcast. I'm proudest of those two, I would say.

• 1:14:47Patrick O'Shaughnessy?

  What's underneath that? Cause they obviously share a common pattern. Like it was you being very open about something very difficult that happened to you. Do you think that that's something people should think about? Like there's some power in speaking the hardest truths or something?

• 1:15:01Speaker 02

  That can sometimes be the case. I should clarify though, that I'm proudest of those for unburdening myself by telling the stories. I don't give a shit about the audience response. I mean, I do and I don't, if that makes sense. That's completely secondary, tertiary. It's so far below the importance of me unburdening myself that it's almost a non-consideration. I'm thrilled by the impact they have had, but principally it was about unburdening myself. And I wouldn't make it a recipe. There is a lot of kind of trauma theater these days where it's like, I live in Austin, you meet somebody here, within five minutes, they're telling you like their deepest, darkest childhood wounds. And you're just like, fuck me. God, this is just too much. It's so performative.

• 1:15:45Speaker 02

  I find it disgusting and offensive when it becomes performative, especially because so many people struggle with these secrets and. Capital T trauma, that word gets overused a lot. It's become diluted because it gets used for everything imaginable. But some people have had horrible things happen to them. Really, really horrible things, very high percentage of the population in the case of sexual abuse. So I never made a recipe out of it. And in fact, whenever there's something that really works, my inclination is not to try to repeat it. I know that might sound counterintuitive, but the reason for that is you have to be very careful about being shaped by your audience.

• 1:16:22Speaker 02

  If you allow yourself to be purely shaped by your audience feedback, you will be a comic caricature of your most extreme behaviors and beliefs. And if you sustain that long enough, you will become the mask that you're wearing and then you're fucked. And I've seen that. I've seen lots of internet celebrity types who have kind of become these monsters of their own creation by allowing themselves to be shaped by audience and algorithm. That is the road to identity oblivion in a sense is allowing yourself to be overly shaped. So for instance, I think it was around 2020, maybe 2021, had a few episodes that touched on crypto and they went completely ballistic.

• 1:17:04Speaker 02

  Nuts, millions upon millions upon millions upon millions of downloads. You know, unfortunately for me, I don't charge dynamically in that way. So sponsors paid exactly the same as everybody else, so they were happy. But as you might imagine, we're looking at the traffic from these various episodes. And someone on my team said, well, here are three other guests we could have on who are top of the field in crypto, based on how well this did. And I was like, thought about it? And I said, no, we're not going to do that because as soon as we start doing this, instead of me following what I'm most interested in, we're dead. Yeah, we're hijacked because I'm not going to be the only one hijacked by this.

• 1:17:47Speaker 02

  There are other people who are seeing the same trend. This is like a lemming transmogrifier to use Calvin and Hobbes term. It's like, as soon as you step into this slipstream, you are coming to group think and group pressure. And you're going to become something you don't want to be, going to make yourself very hard to disambiguate from other people. So I constrain that and didn't do it. There are other times occasionally, if I do something that gets a great response and I'm still super excited to dive into it, fantastic. But frankly, after a while, I was so sick and tired of crypto. I just did not want to talk about it for another second. I was done, which is not to like throw, you know, the entire crypto world under the bus. I still think there's a lot that's very interesting about blockchain.

• 1:18:30Speaker 02

  But when people get this messianic zeal about it, I suppose that just about everywhere bugs the shit out of me.

• 1:18:40Patrick O'Shaughnessy?

  We got pretty far without talking about investing, and that's great because I think fundamentally what's interesting to me is allocation, allocation of energy, of resources, of all these things. And people that find a way, my version of like works of imagination is figure out how to allocate this limited energy you've got in cool, interesting ways. I don't really care what it is, sushi, rice, or whatever it is, doesn't matter. I wonder if you have any closing thoughts that we haven't talked about, or even just ways of summing up as someone that I respect, that I think has been a great allocator of time and energy in these things. For that thing itself, for living this very short life in such a way that the energy is well spent and well used,

• 1:19:20Patrick O'Shaughnessy?

  and creates that joy of making that you open the conversation with, the works of imagination, all these great terms. Any closing thoughts on allocating this precious set of resources we're giving well in life?

• 1:19:33Speaker 02

  Give it a stab. It's a big one. I still have a lot to learn, but I would say at this point, as you get older, you just have, what would we call it? Not to get too hand wavy, but less chi, less vital force. You just look at little kids running around, bouncing off the walls. There is something to it. Like you do slow down a bit, and I think that the most precious non-renewable resource, I used to say is time. I don't think it's time any longer. I think it's energy. I think you have energy fundamentally as the most important, primary resource to guard. And that in turn determines the value, there's a little more to it.

• 1:20:15Speaker 02

  I'm thinking a lot about this these days, but determines the value of your time. If you don't have any energy, it doesn't matter if like, okay, you're with your kids or you're trying to work and you have no energy. What's the practical value of that time? It's diminished, obviously. So getting really good at paying attention to your non-verbal creature responses, these highly evolved sensory tuning forks that we have that predate language by a very, very long time. Pay attention to your body responses to things. Just say, like, is it like slight wince? Is it like slight slump, energy down? When you see that call come in from someone, like, what does your body do? Right? When you see

• 1:20:57Patrick O'Shaughnessy?

  The green button test.

• 1:20:58Speaker 02

  Yeah, when you see, when you see that, when you see, yeah, when you see that text come in, what does your body do? Pay attention to that and make that part of your calculus for deciding what to say no to and what to say yes to, what to cut out, what to add. That'd be the biggest one for me. And no is a complete sentence. Can't make it, sorry. That's fine. You don't owe everyone in the world a big explanation. You know, I like to say, sorry, I'm in monk mode. Can't do it.

• 1:21:25Speaker 02

  The investing stuff, everyone's an investor. Everyone has a set of resources, a set of currency. How are you going to place it in places that are higher ROI, higher leverage, high enjoyment, energy in versus energy out? It's all the same thing. I see a lot of people invest and get great compounded returns and are very stressed out doing it. And I'm like, well, what is the point of all this investing in the first place? Is it to improve your quality of life? If so, maybe you should shift things into your portfolio that lets you sleep better at night. Or is it to win the game? Okay, if it's to win the game, be really explicit that that's why you're playing it. And maybe that'll affect how you center yourself around possible stressors associated with it.

• 1:22:10Speaker 02

  So the investing game is fascinating. I'm only really good at a very narrow band of early stage consumer facing stuff, I would say. The rest of it, I've had my face ripped off so many times in the last few years. Oh, my God, I shouldn't give advice to anybody. I've learned a lot of things that I'm extremely terrible at. Particularly ill suited to. It's part of the journey.

• 1:22:33Patrick O'Shaughnessy?

  To corroborate what you're saying, I think, I can't attribute it because he's like the most private guy ever. But maybe the second best living investor after Buffett has this concept of like, and he himself is the second best, probably like IRR or compound at annual growth rate for decades and decades. His entire focus is like, are you enjoying what you're learning and the people you're learning it with and from? And if you do that as an investor, like, you're going to have fantastic returns. Like, the returns are going to be great. And that's what people will point to and say, wow, look, great investor. And what they don't realize is that the entire driver is the fun and the people and the learning. And it just seems like you've so exemplified that. And it's been really fun to watch and learn from you near and far. I ask everyone that I do this with the same traditional closing question. What's the kindest thing that anyone's ever done for you?

• 1:23:19Speaker 02

  I mean, there's so much kindness. I could rack my brains trying to come up with the best example, but I'll give you the one that immediately popped to mind. And that is a close friend of mine, I won't name him, but I was going through a very tough time, or I was about to go through a very tough time. This was after my breakup a year and a half ago. Very amicable, but very sad on a lot of levels because I thought for sure we were going to build a family together. And he just flew out and was kind of on hand not to fix anything, not to do anything, but just to be there in close proximity, very busy guy, just flew out. And I've had a few friends do that at various points where they're simply aware,

• 1:24:00Speaker 02

  they have the presence of sensing that I could be on the verge of going into a tough time or a dark place and they show up as presence. They're not trying to solve any problem, but just their presence alone. And that proactivity has been so moving to me. And I've tried to reciprocate that in various ways and do that for other people as well. Yeah, that comes to mind. That comes to mind for me.

• 1:24:26Patrick O'Shaughnessy?

  Beautiful closing thought. I'm really appreciative of the time today and just the cool example that you've set. Now there's proliferation around a lot of the things that you were early to. I'm sure no small part to people having been inspired by your lead. And certainly I count myself in that category and it's been tons of fun learning from you. So thank you, Tim, for your time and for your friendship.

• 1:24:47Speaker 02

  Thanks, Patrick. Thanks to you as well. Thanks for having me.

• 1:24:51Patrick O'Shaughnessy?

  If you enjoyed this episode, check out joincolossus.com. There you'll find every episode of this podcast complete with transcripts, show notes, and resources to keep learning. You can also sign up for our newsletter, Colossus Weekly, where we condense episodes to the big ideas, quotations, and more, as well as share the best content we find on the internet every week. [Music]