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

26:47He 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. 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 is my high school wrestling coach, very tough, very, very, very tough. 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.

27:35And sometimes you need someone to kick you in the ass and make you do that. You know, I remember training and wrestling with Mr. Bucks and there's a garbage pail in the corner when you had to vomit. He'd make us through these just awful drills, metabolic conditioning drills. 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 going to sit down, you're going to work on A, B, and C until dinner. Holistically, he was also a very good caregiver and shepherd for his flock of student wrestlers.

28:09Going 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. I talk about flow and chemistry and 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.

28:41And I'm curious how much you think about one versus the other and what governs your behavior. 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 touchdown. Don't fuck it up. 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 going to be received the way that it was.

29:18So 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 200 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 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.

29:53But 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, the scope would be much more constrained so that I could find my 1 ,000 true fans more quickly and reliably.

30:32It would just need to be a long tail search term at this point. 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 expressed lots of different ways? How variant is the story or the scaffolding behind the performance of all these people that you've explored? 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.

31:13You 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 for 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. 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%.

31:56It is a winner's 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, say, product people or engineers. You see a couple of different overlapping circles where they're top 20. They're not necessarily the best of the best, the LeBron James 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.

32:36It'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. Because you think that their performance in a second domain proves that it's not just like a genetic advantage or something? That's part of it. There's something that can be done about it? 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.

33:13When you really dig into these stories, it's not quite so simple. 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.

33:53Everyone 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? 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 iBankers 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.

34:29Number 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 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 to podcast successfully. It's like, what? You're like stressed out any of them. They just fall apart.

35:10But I have never offered payment terms, as an example, to sponsors. If you want to pay for the podcast, you have to pay up front. 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. 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 were like$10 or$12 CPM.

35:52I 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 moved the needle, like the newsletter, the blog, which people forget the blog was the connective tissue that allowed the books to provide 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 on Tim.blog. But zooming out to the macro for a second, my ideal is a sponsor who sticks around for five, six, seven, eight, 10 years.

36:36I 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, whatever it is, checkout process sucks so badly that there's all this slippage.

37:20And 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 very well. It's straightforward. forward. We have it incredibly streamlined. There is demand.

38:02It 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, could be anything. And then, of course, as a 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. 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 sort of enthusiasm to intent to click through to conversion, how my audience behaves.

38:52And that would also keep my team quite happy and interested if they're able to engage with some of those metrics. Why don't you have one? 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.

39:35Do 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. I'm sure there's many more. Would the perfect model be you just did whatever you want? 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 different methods. And then you own equity and stuff.

40:11and that's the whole business? Like, is that the platonic ideal of the business model because of how powerful it can be when it goes well like it did for you with Uber and some of these other businesses? 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.

40:53And 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 angel investing. Very uncrowded. I will say that I'm 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 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.

41:30Once 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 a time, certainly, when I'm promoting startups in which I own some equity on the podcast, that would make sense. There are also, 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, I was also the first advisor to clear the biometrics company.

42:14Oh, wow, cool business. Yeah, really cool business. They've executed incredibly well. Those take a long time. I mean, most of these startups you mentioned, Shopify became an advisor when they had eight employees, maybe eight to 12 employees. And that's a seven to 12-year journey. and 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. What's behind your ability to find the uncrowded emerging spaces? It does seem like you've done that. A certain number of times you start to not think this is luck and there's something else going on.

42:53It does seem like you showed up early or at a good time in a couple of 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? 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?

43:27what'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 network channel. The process is very simple. I talk to a handful of friends or I reach out to strangers who've 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?

44:07What 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 four hour work week. For The Four Hour Chef, my third book, the answer came back podcasts, absolutely 100 % podcasts. And so the foundation of my entire launch plan for that book was podcasting, meaning as a guest, appearing as a guest.

44:44And then I got a taste of it and I looked at it and like 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 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 was like, okay, this has all the ingredients of something that's going to go completely ballistic.

45:27So 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, I would say, responding to doors that opened as much as anything else as a byproduct of the launch strategy for the four-hour workweek. So there's an expression, I can't recall who first said it. I certainly did not originate it, but the target is not the market. Meaning my target for the initial launch of the four-hour workweek was, let's say, 20 to 35-year-old tech-savvy males in San Francisco and 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.

46:18So 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. 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.

46:55Then 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, 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 Hobies and I would help him with various questions around the fitness stuff and also marketing and launches because my book had just exploded.

47:35And 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 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 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.

48:11And 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 the dynamics of the ecosystem and where some of the gaps were.

48:49So at that time, there were only a few people, very few, two or three who were known who were 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 audience after the first book and that's how it started.

49:30That was more of a response to a lot of the inbound that I received after the first book. 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 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 trying to keep things on track on a quarterly basis, et cetera, but a few things come to mind.

50:30The first is really trying to connect everyone to what impact the collective effort is having in the world is really important. 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 the F1. 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.

51:12My 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 proud of from this last week and things like that that I 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.

51:51And therefore I have created constraints that force me to operate within my zone of competency, which is very small team. 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? 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?

52:27Like George and Seinfeld. Exactly. Yeah, like George and Seinfeld. Yeah, exactly. Just draw me on rye. Yeah, exactly. Exactly. So for instance, the Costanza 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 out.

53:07It is the anti-video, and I feel better doing it. And so far, every conversation I've loved doing, how my audience responds, TBD, but a lot of my audiences really appreciate it because they're like, you know what? You're right. We do sit in front of screens way too much. Thank you. Because 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.

53:43at least with some frequency. It could be a two-week experiment, it 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 it could be a constraint of subtraction. Like, what if you couldn't use your phone 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.

54:18And I like that. I enjoy that type of experimentation. 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 major reasons we don't do video. And I took my picture of everything. And what 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.

54:53And 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. 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.

55:26If you have kids, you should also look at it because 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 at a restaurant.

55:48Access, 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 or 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 sometimes a challenging conversation to have with my team because they like to see the podcast grow.

56:32They 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 to peg it geographically. Fam. 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. I say to me at one point, he said, yeah, DC is just like Hollywood, but with uglier people.

57:12So 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 has 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.

57:58Yeah, 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 it 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.

58:38I don't 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, 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 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.

59:22I definitely end up here. Every once in a while, I'll be thinking about the podcast and we can do A, B, and C, and D, and F, 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. And I think part of it is that fame, power, money, they're all amplifiers, just like alcohol, let's just say.

59:57If 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? 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.

1:00:38He'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, 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. That's a great, great, simple heuristic or something. I think so much of the challenge is 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.

1:01:17So 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 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.

1:01:51All 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, 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.

1:02:25Doesn't roll off the tongue. Yeah. I struggle with this. It makes me feel 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 tenth grade teacher, specifically because it seems like kids, especially in ninth grade, they kind of have many branches in the tree, many different decisions they can make.

1:03:09And 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 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 chef.

1:03:45I break it down, but I have a framework for doing that. I'm a very, very fast learner. 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.

1:04:28compared to something like a book. For that reason, I think I will continue to write. 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. I'm really curious about 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 a 500 to 1 compression ratio be 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 freaking guy that you can read about in a week or two is pretty wild.

1:05:06I'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? I think I need to have some kids, frankly. I think that's the next big adventure because 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. We got out of a very long relationship just a year and a half or so ago.

1:05:44If you had to condense down that meta-learning chapter, what do you think the key framework is? I can explain it. I'm happy to explain it. I use it all the time for everything imaginable. The process is as follows. 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 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.

1:06:28And 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. 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. It has a lot of words.

1:07:07English 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, 1500 words, be conversationally fluent and able to read most things in terms of frequency of appearance. 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.

1:07:46But the things I get done tend to be very high leverage, or a lead domino that knocks over other dominoes. 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, and I grew up on Long Island, keep in mind. I had a couple of near-drowning experiences, and 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.

1:08:27Total 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. 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.

1:09:02I've done that before with selection, for instance, for purposes of tango. 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.

1:09:37You would have been a good quant investor. you're basically describing good quads 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.

1:10:09And it needs to be really compelling. And if you do that, a lot of these other things fall in line. 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? What is it that unlocks such good teaching for yourself or others?

1:10:40Let'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 them how to learn, 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.

1:11:14Next week you're learning this. Week after you're learning this. If you know how to apply this now, holy shit, man, with ChatGPT and other tools at your disposal, perplexity is really good. 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 a systems to do this faster? Yeah, you have to get really good with the spellcasting with prompts to make it conform to this because the machines aren't going to necessarily understand the terminologies I'm using them.

1:11:48But I know people who have learned to code video edit in next to no time using just chat GPT. all of that is going to 10x in the next six months and then the next six months. Do you feel 10 years in like you're at any sort of crossroads? 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.

1:12:26I 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 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, in television or film, but I don't really want to deal with the machines of Los Angeles very much.

1:13:11Who 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. Retrospective on everything, not just podcasting, but all the teaching that you've put out and 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? 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.

1:13:42I feel very good about that. It's also SEOed 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.com, it's about as fun as it sounds. The episode, I put it out September 2020, My Healing Journey 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.

1:14:27I 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 a 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 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.

1:15:04It 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 that 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 weekly letters from people related to that podcast. I'm proudest of those two, I would say. What's underneath that?

1:15:42Because they obviously share a common pattern. 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? There's some power in speaking the hardest truths or something? 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.

1:16:18I'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. 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.

1:16:55But 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. If you allow yourself to be purely shaped by your audience feedback, you will become a caricature of your most extreme behaviors and beliefs. And if you sustain that long enough, you will become the mask that you're wearing.

1:17:29And 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. Nuts. Millions upon millions upon millions upon millions of downloads. Unfortunately for me, I don't charge dynamically in that way. So sponsors paid exactly the same as everybody else.

1:18:10So 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 Because I'm not going to be the only one hijacked by this. There are other people who are seeing the same trend. This is like a lemming transmogrifier, to use Calvin and Hobbes' term.

1:18:48It'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. You're going to make yourself very hard to disambiguate from other people. So I constrained 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 throw the entire crypto world under the bus.

1:19:22I still think there's a lot that's very interesting about blockchain. But when people get this messianic zeal about it, I suppose that just about everywhere bugs the shit out of me. 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. It doesn't matter.

1:19:57I 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 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? 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?

1:20:36Not 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. 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. 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.

1:21:18What's the practical value of that time? It's diminished, obviously. So getting really good at paying attention to your nonverbal 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 a slight wince? Is it like slight slump, energy down? When you see that call come in from someone, like, what does your body do? The green button test. 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.

1:22:05That'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. 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?

1:22:44is 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. 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 too it's part of the journey for crowbar 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.

1:23:46And 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? 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.

1:24:20And 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 gonna 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, 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.

1:25:05They'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. 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.

1:25:39So thank you, Tim, for your time and for your friendship. Thanks, Patrick. Thanks to you as well. Thanks for having me. 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.

1:26:11Thank you.