Deep Questions with Cal Newport - IN-DEPTH: The Game of Life (w/ Tim Ferriss)

Episode Date: September 4, 2025

In this episode of IN-DEPTH, Cal is joined by bestselling author and podcaster, Tim Ferriss. Tim rocketed to prominence with his 2007 book, “The Four Hour WorkWeek” which basically redefined a generation’s relationship with work, meaning, and the possibilities for building an interesting life. More recently, Tim created a card game! It’s called Coyote. And he created it with one of the top designers in the business, the same company that created Exploding Kittens.Video from today’s episode:  youtube.com/calnewportmediaINTERVIEW: The Game of Life (w/ Tim Ferriss) [3:16]Links:https://www.explodingkittens.com/products/coyoteSponsorshttps://www.reclaim.ai/calThanks to Jesse Miller for production, Kieron Rees for the theme music, and Mark Miles for mastering. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

I'm Cal Newport, and this is In-Depth, a semi-regular series in which I talk to interesting people about the quest to cultivate a deep life. Today's episode is brought you by our presenting sponsor, reclaim.a.I. This is a product I'm actually really excited about. I mean, they use the word deep work when they describe it. So I'll come back a little later to tell you more about that. But what I want to tell you about right now is today's guest, the one. one and only Mr. Tim Ferriss. Tim, of course, rocketed to prominence with his 2007 book,

The Four-Hour Work Week, which basically redefined my generation's relationship with work and meaning and the possibilities for building an interesting life, a major influence on my work for sure. He followed that up with a series of other massive bestsellers, including The Four-Hour Body, The Four-Hour Chef, Tools of Titans, and Tribes of Mentors. most people probably know him today for the podcast he started right around the time he was

wrapping up the four-hour series. It's called The Tim Ferriss Show. And there's one of the first big business interview sort of self-development podcast out there. Some people have called him the Oprah a podcast. And I see why. This show has been wildly successful. It's surpassed more than a billion downloads. Tim has interviewed countless major figures from Jane Goodall to Jerry Seinfeld to LeBron James. And his big, as Git of all, of course, myself. More recently, Tim put out a card game. It's called Coyote, and he created it with one of the top designers in the game business,

the same company that invented exploding kittens. The game is a blast. Okay, so given all of these things, what did Tim and I talk about in this discussion you're about to hear? Well, we started with Coyote. I wanted to know why did he build a card game? And more importantly, like, how does that world work? like how do you become the top designer in the card game business what does it take to really strike it big in game designing and how is that different than what other people who try to strike it big in game designing and don't succeed what's the difference there like how i'm just curious about that world so we start there

but then we go deeper tim and i talk about his path to stardom we talk about the autonomy and depth he had in his life circa the time when he was writing to four-hour work week and then how his own success stripped some of that away and his effort since then to get it back. We talk about his future plans for his podcast and for writing where he wants to go from here. We really get into some really interesting territory about one of the masters of this topic, how he feels what he's thinking about and what he wants to do. This is a must-listen episode if you have any interest in the deep life. Tim really is sort of the OG of the deep life.

life as a concept and he obviously has a lot of interesting things to say he speaks from a place of deep experiment deep experience so anyways let's get right into it without further ado here is my conversation with tim ferris all right tim thank you for joining me always a pleasure great to talk with you of course yeah yeah lovely to be have the band back together that's that's the way to think about it uh so i mean i want to open with the reason why we originally thought about talking, which is you made a game. Yeah, WTF. I'm holding this up to the camera.

Coyote, walk us through just to set the foundation, just give us the basics here, what type of game it is, who you did this with and where is it, just so we know where we're on the same page. Sure, so the basics are, and there's a lot of backstory, but I grew up kind of saved by games, mostly very complex games like Dungeons and Dragons. I still have all of my materials downstairs from when I was a kid.

and I, for a host of reasons, felt like games, analog, social is just every year. As kind of digital goes vertical, the counterbalance of analog and social is becoming more and more important. So I thought, you know what? Maybe I should make a game. And it is a fast, casual, social game, made it with exploding kittens because I became close friends with Alon Lee, used my podcast to sort of test the waters. And they've made a whole host of great games and tested a few dozen games with my friends and came across poetry for Neanderthals,

which is an exceptional game. Maybe it's just by me and my dumb friends, but that's the one they wanted to play over and over again. And I was like, well, who made this game? Oh, Exploding kittens. Who's behind Exploding kittens? And that's how I kind of pulled on the thread. And right now, Coyote is...

It's doing very well. It's got like 300 million plus social views of gameplay online. And you can find it everywhere. Just launched. And plays three to eight folks, typically kids can play. I'd say 10 plus. So very, very simple to learn, but different every game. It seems like it's physical memory.

How do you describe this game? It's like you have to do motions. And the ones and the cards, as the cards come down, it changes what people have to do. and trying to keep track of where everything is. Totally. And it gets kind of frenetic. So under the hood, and all of my books are designed this way as well,

there is a Trojan horse with this game. So it has to be fun, and people need to want to tell their friends about it and play again, right? That's table stakes. But under the hood, it is also a workout for your brain. And I've spent a lot of time thinking about this kind of thing. But by and large, people are not interested in buying things to make them smarter. I know it sounds crazy.

But I've tried this multiple times in the U.S. at least. It does not work. So this has to be a side effect. But yes, it's basically a gesture, rhythm, and verbal game, where it's almost like rock paper, scissors on steroids for a group where you try to match all these things as you go around the table. And if anyone makes a mistake, they lose. a life and then last person standing wins.

You can also play cooperatively if you have someone in your family who's a really sore loser or a friend who just complains too much. But the competitive mode is really kind of where the smack talking and I think the adrenaline and a lot of the fun is. So it is a rhythm and gesture game where people have to perform in action, say what's on the card and go around in a circle, keeping a certain rhythm. And the reason it's called coyote is because I'm I want people to find their inner trickster.

If you think of the mythologies around coyote in many of the indigenous cultures in North America, also in Mexico, I suppose that includes Mexico on some level. But this coyote character pops up again and again. In every culture, whether it's Loki, Ictomy, or others, there is some type of trickster. And the reason that's part of the game is you can sabotage other players. So if you have somebody who's really good at say math or music,

those folks tend to be very good at this game, you can handicap them by slapping them with the tack cards and things like that. So that's the game. And you can learn to play in a few minutes. But as someone who spent 20 years in Silicon Valley, still also to this day investing in tech startups

and everything else, I think we're wading into some very risky waters with a lot of the technological saturation and everything else, which we could talk about. So getting offline, giving people a light lift that provides sort of a little bit of vitamin P, vitamin play, I think is really, really, really important. So I've been playing a lot more games versus just staring at a screen 18 inches away all day, every day. And that's why I made it.

I'm curious about this world because I think about this type of game that you call it casual or fast casual? Is that what was the term? Yeah, yeah. And there are lots. One thing I realized, and part of the reason this took two years to make is there's so many different... If you say I want to make a game, it's kind of like saying, I want to start a business. It's like, okay, well, we need to drill down a little bit. So you could call this, I would describe it as fast casual.

There are other ways to describe it, but meaning after dinner, you've got an hour, maybe a few people have had some drinks, what do you play? If you try to play some of these other games, which are fine games, wonderful games, terraforming Mars, you're never going to get it done, right? And furthermore, if people are tired or a little fatigued after a long workday, it's going to be hard to recruit people, at least my friends, to play it. So this is along the lines of an Uno or the Monopoly Go card game, something like that. It's closer to that side.

So because what fascinates me is it reminds me of screenwriting. And here's the connection I want to make there, is that. I'm excited about this. When you talk to screenwriters, they say, look, people think this is easy. Because when a script is on the screen and it works, you're like, I could think up a similar idea for a movie and I know how to talk. But I'm not watching someone drill, you know, Steph Curry drill a three-pointer from six feet behind a line. Like, oh, I can do this. This is a great.

The alien attacks or whatever. A good, fast, casual game, if constructed, right. You're like, oh, this is just fun. Like, you have some rules. You have some ideas. It kind of goes back and forth. But when I talk to screenwriters, they say the issue with the screenplays, everything has to be right. It's a watch mechanism.

Like everything and you don't realize. That's a very good way to put it. If you introduce like Chekhov's gun, like you mentioned this here, it better pay off there. No dialogue cannot have a purpose. Like this has to connect to this. And even a bad screenplay, you have to be a professional screenwriter to have written the bad screenplay because there's a technical complexity. the just making a script that everything connects together. I assume this is similar for making a game like this.

You said two years. I'm curious about that world, the world you met with, Ilan Lee, what you learned from him. What is it like in the world of trying to make a card-based game that is easy to learn if on the play? What goes on in that world to actually make a game like that? Yeah, let's talk about it. And what we're about to talk about, right, how that watch is built is part of the reason why I decided to do something completely off-menu. completely different from what I am accustomed to doing because I choose, and maybe we'll get more into this later, but I choose projects based on the density of learning, skill acquisition,

and relationship development, all of which should transcend that project even if it fails. And so the question of how do I win even if this fails is always present in my mind. So with this, let's dive into it. How do you build this watch and rest assured whether you make a very very very, very obviously sophisticated game or a very, very simple game, there's a lot of complexity or there can be in the process if you want it to work consistently. So I've learned so many things from Milan.

And he's such a sweetheart of a guy and such a polymath. I mean, he'd worked on the original, on the Xbox, on HALO, on entirely new genres of games. I've seen him make entirely new types of games that have not existed in the world before. But he comes out of video games. He comes out, well, let's see, what does he come out of? I mean, he comes out of so many different places. It's hard to slap a clean label on him, which I like.

I remember I asked him to send me his bio, and I was like, I don't even know what to do with this. And I was like, okay, I like this guy. And he cannot help himself, but create games. And also, and I'll get into the kind of the process in a second, but games are fundamental to human life past a certain rung on Maslow's hierarchy of needs. I think, I'm sure you and I could talk about this forever. So it's like you are, if you're listening to this podcast, there are many games you are playing in life with rules, with stakes, maybe with a quitting time, whether you're aware of them or not.

So studying games helps you kind of peer behind the curtain to see the games everywhere. where around you and to choose better games also. Okay, process-wise, what did I learn? Well, number one, there are a hell of a lot of different types of games. You can have magic type games where you're building decks, where you're collecting cards. You could have a D&D role-playing game, very, very, very, very complicated and involved. Then you have all the way over on the other side. You have some very seemingly, at least when it's done right, simple to learn games.

And what I realized, at least for me, was number one, just deciding on the direction was the most challenging part as a first-time game designer because I was involved in every single step of the process, which I'm sure slowed things down for them. And then 10 minutes of trying to prototype is worth 10 hours of talking. That's something you learn very, very quickly.

What does a prototype look like? for a game like... I'll tell you, for a game like this. Yeah. We applied a bunch of constraints. So I started with, and in conversations, we did a number of sprints. Alon and I, friends of mine,

just as testers, right, as players. And we're trying all sorts of different original games than we're looking at potentially taking an easier path, which would be taking, say, the game that led me to Ilan. Poetry Fernandrthals, creating a variation of, of that with new rules or a twist on the rules. And ultimately wanted a few things to be true.

Because I played, for instance, chess with my brother. My brother is very mathematically inclined. I'll leave it at that. But he always will beat me at chess. And that's annoying. Number one. Number two, he also wants me to like suffer through going all the way to the end to get knocked off even if I see very quickly oh I just painted myself into a corner I'm doomed this is checkmate so I wanted to be closer meaning the game that I would make closer to backgammon or poker than chess in the sense that there is a chance for a weaker player to win if they have some good luck and that also came from playing magic with a couple of friends of mine and I was like this sucks not because magic sucks but because they would always beat me

Always. And I was like, well, this isn't fun. I don't want to play this game again. So it was a constraint. And then thinking of other constraints, like, well, what can be prototype quickly? Cards. We could also use chits, meaning something you use to keep track of lives. And we played around with a bunch of other accessories.

But here's what the first prototype looked like. We were doing a sprint, the last sprint, because we had tried sprints over the course of 9 to 12 months. and we hadn't found something yet. Because for me, if I'm going to put my name on something, man, I need to be willing to live with this forever, which means it's got to be something I'm excited to talk about, which is a high bar for me.

And then we decided, look, we're both very busy. We haven't found something yet. Let's make this the last sprint. We either commit, well, we do commit, to either finding something and running with it or calling a spade a spade. And we're just grasping in the dark here. and it's probably better for us to focus on other things.

And what's physically, like, what are you physically using in a sprint? I'll tell you. Yeah, I'll tell you. So the sprint, first of all, just looks like us walking around, well, this happened to be in Toronto. So walking along the waterfront, drinking copious amounts of coffee, talking about games. What if this? What if this? What if this?

And the breakthrough moment came when I think prompted by either Alon or Ken Gruel, who is one of the employees that explains. splitting kittens, an amazing game designer. I think it might have been a lot. I think he broadened the question, and we ended up with a better question. So the question was no longer, what tabletop games have you really liked?

He's like, let's broaden that. It could be kickball. What are the games you've liked? Any kind of game. And I was a little shy because I've got professionals here who have done also very, very, very, very complicated games. Sophisticated, I should say.

And I said, you know what, this is embarrassing to say, but if my friends and I have had a few drinks, even if we haven't, playing rock paper scissors, we really enjoy it. These are smart friends. And I was expecting an eye roll, but instead they were like, okay, let's roll with it. Like, what does that look like? And I was like, well, what could it look like in a group of, say, four or five people? And let's say we're only using cards, but we could add in some dice

because I wanted that chance opportunity for a weaker player to win. So I was attached to dice because I love like a 20-sided die out of D&D. I just really wanted to use a D20. So D20, I really want to use a D20. Now, in retrospect, I'm glad that we applied more constraints to use only cards because, for instance, Exhibit A, tariffs, uh-oh. It's adding these components adds a lot of cost. And we had this kernel of an idea and we basically raced back to the kitchen table

and had a bunch of blank decks of cards. Could just be index cards, doesn't matter. Markers and a bunch of accessories. Kind of looks like a craft shop in Alon's house. You can imagine. He's got every possible little knick-knack you can use for making games. And Ken and Alon and I just sat down and started making cards and tried a bunch of things

and literally had a V1, like version 1, ready to playtest in 15 minutes and then tried it barely worked but there was like something so we're like okay let's double down on that piece let's take this other thing out throw away a bunch of cards or just cross them out and put something different on the card try again try again so we were able to iterate sitting at a table with blank cards over and over and over again for a few hours And by the end of that weekend, I had to rely on Alan in the sense of pattern recognition and his taste sensors, his kind of water feel for games. Because I felt like there was something there. But Alon has seen hundreds and thousands of games, right?

As has Ken. And I was like, what do you think here? Right. Like 0 to 10, a question I like to ask, right? Zero to 10, no 7 allowed. I learned this from Kyle Maynard who learned it from somebody. else, but like zero to 10, no seven allowed. Where do you rate the potential of this game and don't blow smoke up my ass? And I think it was like an eight or a nine, the possibility of getting it higher. And I was like,

okay, if that's true, let's pause for now because we were wiped out. You know, after playtesting and especially this game also, if you want to, if you have trouble getting to sleep and you want to get to sleep, like play a couple of rounds of this before bed. And you, you know, you It might just be easier to sleep. I say that as a lifelong insomniac. So we were wiped out. But there was enough proof of concept there to say, okay, let's expand this, make a very, very rough deck, and playtest it with other people to see what happens.

Was the motions in the beginning, like the initial play testing, was it closer to rock paper scissors? Like at first, was it just, hey, we have different hand motions. The details didn't matter? The details didn't The details do matter But in the beginning And this is again Keep in mind

I'm like the skier Who's been on the like a couple of slopes six times So I'm like tell you let me tell you all about skiing Right Here's what you got to know When you're jumping off a cornice It's like whatever you know But keeping all that in mind

Big Grand of Salt I have learned a lot of taking a lot of notes I've documented everything So here's what I would say The details do matter But in the beginning you don't know Which details matter So you just throw a lot against the wall.

So we tried tons of stuff. And what Alana is very good at doing is, and I would say I'm not terribly good at this, is brainstorming and testing without too much judgment. So leave the editor aside. And no matter how hairbrained, how boring, try everything. Because it's so fast prototype. The turnaround time is so fast with this type of game construction. that you should just try it.

You'd never really know. So in the beginning, there were a lot of gestures, for instance, that we ended up pulling out later example, anything that's kind of not suitable for work, which were very reliable at getting laughs. If you're going to distribute at Walmart and Target where you want to, chances are you're going to have to yank some of those out.

And similarly, some of the cards had people standing up from a table to do something. Well, if you have somebody at the table who can't do that, you've just run into a big problem. Yeah, right? So yanking those out. Now, later, you can have expansion packs and you can have print-to-play PDFs

and all that stuff, which I plan on doing. But there was a lot of vetting. Now, once it goes back to Explanickinson's headquarters and they're playing it internally with employees, then they have an entire system for play testing. They have an entire, very refined system for play testing. And at that point, we also were creating spreadsheets with multiple tabs of different gestures, which have corresponding words.

So you can change the gesture, you can change the word, you can change both. And we had a ranking system for everyone. So we just had hundreds of these things. And what's the data to rank them? Yeah. So there was a, as I remember it, there was a one to three ranking system. And one was this isn't interesting at all. Two is it's sometimes interesting.

Three was it seems to hit most of the time and get a laugh, right? There were a lot of questions around like how many kind of laugh out loud cards should you have. And if you only aim for those laugh out loud cards, does that actually handicap the game? Because it makes you kind of deaf to it after a while. Do you want to preserve it for like variable reward? and in addition to that, there are some decisions to be made about just, hopefully this doesn't sound boring, but deck construction, like there are 66 cards, why on earth 66 versus 86 versus 36, all of that revolves around a combination of variety.

Things are color-coded because you can play with people's brains in weird ways once you add colors. So a certain amount of repetition with colors deciding which cards to replicate and it comes down to a lot of probability. How often do you want certain cards to show up and over many, many games? What do you observe? And mathematically, what should you see?

Which then feeds into questions like, for instance, initially we had the game produced where you do what you do with every game. You shuffle the deck. Right? Yeah. But if you have the gesture cards or action cards, they have salamanders on them, can explain why there's salamanders on them.

There's a good reason for that. But then you have the action cards, then the coyote cards. They're all grouped together initially. And when you would shuffle, you wouldn't get, most people don't shuffle very well. If you just do a riffle shuffle, it doesn't actually mix the deck that well. So they would end up with these solid groups of identical cards. That doesn't work very well. You're seeing this in play testing.

Like the people are shuffling not. not well and you're getting like six elements in a row or something. Yeah, exactly, exactly, or six coyote cards or whatever. So then you go back to the manufacturing and manufacturing cards is surprisingly challenging. The actual manufacturing facilities are gigantic. They are huge. And they're relative to many other types of games or things you could produce, a few, relatively few of these manufacturers.

Are they in China? At high volume. A lot, most of them are in China. Same as bookprinting, basically. The same as book printing. And what you can do is off the line, you can manufacture a shuffled deck. So you can indicate what type of composition you want the deck to have as a quote-unquote shuffled deck. So then when people pull it out of the box, they have a really good first time out-of-box experience.

It's so important. It's like if the first two rounds with or they're just me, that. is going to crush you. And particularly since it's like this thing's cheap, right, it's half the price of a movie ticket basically in the U.S., right? It's $9.99 or around $10. So if they play twice and it doesn't totally work, if it doesn't make them laugh,

are they going to play again? Maybe, maybe not. So you need the out-of-box experience to be really good. It's the amount of time that you spend on the instructions also, play testing the hell out of that. because once you do the internal testing, then you can go out to families and other people you've recruited to playtest.

And this is also, there's so many parallels with tech and any type of product really, I think direct to consumer, but it could be applied anywhere. If, for instance, I think user testing.com might still be around. I'm sure there are better tools now. But back in the day,

it's like, right, if you want somebody to try signing up for your software as a service on a website, you could ask them, what did you find confusing, how was it? Or you could just do a screen capture with a video and watch their facial expressions and see where they pause and take too much time. So similarly, with playtesting a game, you don't want to just ask somebody what did you think and have a list of seven questions. Do you want video of them playing? Like how long does it take certain parts of the game to transpire? Are there huge pauses where people get? gummed up. Where do they laugh versus where do they report they laugh? These are, these are

often things that have huge discrepancies. So suffice to say, to figure out a simple game is not so simple. And it has given me so much more appreciation. It's kind of like if you, for instance, I'll give people a recommendation. I love drawing. I've done, I was very involved with all the artwork for every aspect of this game and did a lot of hand sketching and so on. But if you have somebody take you, let's just say a nature guide, take you on a tour somewhere around your house and introduce you to all the tree species. Usually easier to start with trees versus general plants, right? So you get maybe like in most places in North America, a half dozen trees, maybe. And now when you walk through the forest on your usual height,

you're just going to see things completely differently. Yeah. You're seeing games. The fidelity, it's like, boom. Suddenly it's 3D instead of green trees. Your labels change. And with your labeling change, your reality changes. And the same thing happens to me now.

If I see other games, I'm like, oh, my God. This is so smooth and so simple for me as the user. Right. It's like if you open any product, let's just say a really well-due. designed to Apple product because most people had that experience and you're like, oh my God, to get the AirPods paired to my phone and to do this and this is so easy. And then you compare that with like, I'm going to throw them under the bus,

but buying like a brother printer. And you're just like an hour and a half year later, you're like, what does it take in God's name to get this thing on Wi-Fi? What is this Wi-Fi button about? Like there's a feature that no one has ever used, this like Auto-Connect protocol that, yeah. So you can have the same experience with the game. where you read the instructions, you're like, I have no idea what this means.

So to answer your question, I suppose, yes, there's a lot that goes into it. And then also, there are things that you can do that translate or can transfer from other places. So for instance, I used a bunch of websites, and there are a million of them, but I think Intellivie is one. Pickfoo.com is another where, you know, I created like, I don't know. We created six to eight variations of this box in terms of the cover art. Right. And then split tested it by serving it to different demographics

and having them select their favorites, meaning one out of two at a time. And then the winner would proceed to be compared against the next variation. And we did a ton of split testing. And just like I did the Google AdWords way back in the day to test the four hour week and the subtitle, you can, where possible, test. With a few hundred bucks, you can get great signal. Not always, but often you can.

With this, it was really clear because the winner was like 10x, right? The standard deviations out was so significant. I was like, yeah, this is very clearly. Did you predict that or are you surprised? In this case, I did predict it. Yeah. I have whatever it is, I don't know what it is. But from a visual perspective, I think I'm just maybe.

a little more acute than a lot of folks. I don't know what that is. But certainly my OCD probably feeds into it. I mean, I have been diagnosed with that, which was no surprise. I had to do it as like a formality. And the therapist was like, or the, I guess he was like, psychiatrist was like, I know this could be a lot to take in. If you need to like pause the Zoom and come back tomorrow, I'm like, this is not news to anybody. Let's just keep going. I need this for the insurance. Come on. Yeah, I need this for the insurance. Let's keep going. But I can draw almost any layout of any restaurant I've ever been in. Like, just like my mind just works that way visually.

So in this case, I was able to, I was able to predict. And I should say also, it's not just data, data, data. It's like, can you, if your name is on this, goes for book covers too, can you live with this forever? Which is why I sometimes, I guess no longer because the publishers can make pretty good money reliably, so they won't say this. But I was a problem author. Like, I was a problem author because I would.

fight. I was like, you guys don't have to live with this. Your name is not on this. And I understand the incentives are slightly different, but like I'm going to see this so many times I need to be happy with it. And if that ends up being the second choice instead of the first choice based on the data, so be it. Yeah. Yeah, I was wondering if there's a drug dealing for fun and profit box that you test equivalent, referring to the listener back to your original title for our work week. Maybe a a coyote with a bloody maw or something that just did not

test well. Well, figuring out just the name took a long time. I tested so many different names and it can become just like with book titles sort of a emotional

not necessarily heated but it can become a conversation based on opinion and you want to test that. You want to test. So for instance, one of the counter arguments against the name of this game was that coyote is very much sort of an animal of the Americas. Let's just call it, maybe down into some of Central America, but mostly Canada, US, and Mexico. And will people actually, will this mean anything to people in other places?

and so I had to do a bunch of polling, which I'll very often do with very short social posts at very odd hours that hit particular time zones, just to see, and also texting friends and so on about this. But then there are, there's so many different variables to land on something that finally works, including box design, box size, pricing, negotiating and handling the politics of very, very large retailers.

These are all independent arts in the decathlon of creating a game. And Alon is just an excellent decathlet. He's good at all of it. So what's that, this is my, I'm curious about new worlds. What's that industry like? Is there big players? It's a lot of independent players. Is anyone making money?

Like, what is the game world? Yeah. a pay to a lot of people. Yeah, this might be a good one where we have the Wayne's world like, we cut to Alon Lee giving an answer. Listen to that podcast episode with you and Alon is probably the best answer. I would say it's a lot like other industries in the sense that you have a few 800-pound gorillas who are gigantic.

You know, Hasbro's Mattels, et cetera. They have internal divisions that are doing what like exploding kittens is doing. like just working on game variations. Oh, yeah. Yeah, yeah. So you'll absolutely. And you'll have these giant within the scope of games. You'll have these gigantic companies that do a lot of things, including something like, you know, the fast casual category.

And then you have a ton of... Then you have the very successful, and Exploding Kittens would be one of the very most successful, let's call it more independent... games studios that make tabletop games. And Exploiting Kins is definitely one of the most successful. I mean, they had one of the most, if not the most successful Kickstarter of all time initially with Exploding Kittens

and then parlayed that into creating a real amazing company with many, many bestsellers. And then you have a super long tail of, let's say, independent game designers and people who are taking a stab at making a game. Yeah. And those folks, almost all. always will license their game to a publisher. It's just like books in a sense and take a royalty because they're not capable of and or they do not want to contend with all the logistics of like supply chain management,

dealing with retailers and all that stuff. And if you only have, say, one skew and you're relatively new to the game, It could be the best game on the planet, but just as with book publishing, if you try to approach big retailers by yourself, they are not going to carry your game. It does not matter how good it is. They do not have the infrastructure to handle thousands upon thousands of independent contacts. So you'll have brokers, which would be the equivalent of, say, book agents, right? It's the same. It's the same thing. Yeah. It's the same same. And that's also part of why I like stepping into these realms that seem to be. completely unrelated, but you start to spot things that you can conceptually at least copy and paste.

The brokers are negotiating licensing deals on your behalf of you're an independent? Those would probably be, this is probably a lot, I'm getting into the deep end of my ignorance pool here, but the brokers would help you potentially place, even for the larger game companies, they would be your interface to someone like a buyer, category buyer at a Walmart or a Target, for instance. and you would have fun you would probably need to find representation of some type to submit games to larger game companies if you want a little bit of leverage

that could also be an attorney potentially I mean that's how I lean with any new industry so for instance like screenwriting right you mentioned screenwriting like that I have had it for like a decade but I have a screenplay that's like 80% done and you're the only one you're the only Yeah. Yeah, right, exactly. So at some point, lawyers are very neglected, right? They get a bad rep in some senses, right? But they are the ultimate connective tissue that holds a lot of any industry together. So I suppose what I would say is that there are these intermediate parties. And very often you will need. need the assistance of one or more to get any type of deal done if you were part of that long tail. Yeah. Which is another reason why it wouldn't have made sense for me to try to do this solo.

Yeah. My learning would have been much flatter. I would have made many more mistakes. And I wouldn't have possibly had the distribution. Would have been, I would say, impossible. It's probably a fair word to use. What's the best case scenario for, like, someone's dream? I mean, you're independent and you just.

stumble across, your playtesting with your friends, and it's just like a brilliant game, like a tabletop game or something like this. And you have someone approach and you license it and it hits, right? When we're talking about like the blue sky scenarios for someone who's thinking about

that, what are we talking about? Are we talking about someone getting rich? Are we talking about? That's a great question. And I can't contractually get into like the details of my deal. But I would say it's very similar to books. Similar to books. I would say that if you have a mega, mega, mega hit, then you can do well.

Is there like an atomic habits of tabletop games? Like you could just, something about what you're doing takes off for years and generates, yeah. I mean, those games definitely exist. I will say that I know for a fact a lot of the game designers who have done deals with publishers who, who later have those games go parabolic and just insane for many years in terms of incredible sales seem to like a DIY their lawyering or otherwise a lot of game designers

and this is true for anyone who's new to anything it's easy to be penny wise and pound foolish so I've seen a lot of let's just call them inventors because this is also true in pretty much any product category and there's a great book on just inventing in general and sort of licensing versus venturing called

I think it's one simple idea by Stephen Key, Stephen with a pH, who's just, he's created stuff for all these gigantic brands. He does almost all of his prototyping with like construction paper and really basic stuff around the house and he's been massively successful. But pay a lawyer to review contracts. Pay a good lawyer.

Like really invest in that. even if you're going to put yourself, obviously not dangerously in the red, but that is where you want, one of the places where you want to spend money. If you do that correctly, then yes, there are people who can make a good living doing this. If your goal is to make billions of dollars or tens of millions of dollars, I would not bank on trying to be in atomic habits, right? Yeah. Like that may be, I hope it's not for James.

I hope he has 10 more of those. But the magnitude of sales of that book might just be a non-recurring phenomenon. Yeah. It's kind of like I was talking to an entrepreneur recently and Taylor Swift wore one of her rings to an NFL game. And I'm like, okay, you saw this huge bump in sales. You cannot in any universe depend on that happening again.

Yeah. That is you stumbled across a bag of money. That's exciting. But don't make your business plan stumbling across bags of money. Yeah. Exactly. Yeah, business plan. Step one. Pick up bags of money.

It's like, ah, that might be hard. If you just keep getting Taylor Swift to wear your stuff, it's a great business plan. What's the problem? But I will say that it is possible to make money in games, but you're not dealing with, say, the margins of software. Yeah. And that's just the reality of a physical product.

It's like books, it sounds like. It's very similar. Yeah, you can make money. Even the price point is similar. Interesting. There are much more expensive games. So if you get into the realm of involved strategy games, like there are games that definitely,

you walk into a game shop, there are games that sell for 50, 75 bucks. I mean, you can find those games. Yeah, but they don't sell very many. Exactly. So you're going to be looking at, I mean, they can sell, but you're going to be looking at, they're always tradeoffs.

They're always tradeoffs. And my goal with this was, and I'm fortunate to be in this position, but the business can work. Exploding Kins has done a really amazing job of building a business. It's not a not-for-profit. So you can make money in this world, but my advice to someone who is thinking they might want to make a game would be the same advice that I would give to someone

who's thinking about writing a book, right? be slightly different. I would say in the case of a book, I'm like, if this can't be your top priority for the next year from a time perspective, don't do it because you're going to have to live with it forever. And if it can, then consider it. Similarly, I would say if you assume that you do not make any money, you don't lose money, but you don't make any. Is this still worth doing for you? And if the answer is no, I would not suggest doing it. Just like if someone said, I'm thinking about becoming a country musician to make my riches, I would say, but if you said, I think I'm going to make an album because I've always loved music, my friends love my music, and I just, I can't rest knowing I never gave it a shot.

Okay, that's a good reason. Then give it a shot. And maybe lightning will strike and you'll capture it in a bottle. Maybe. A fascinating world. Well, let me, okay, so let me zoom out on this a little bit then. Oh, can I say one more thing? Sure.

That I have tried more and more. to immerse myself in worlds where the people are friendly. This sounds so maybe, I don't know, like Mr. Rogers, but some worlds are friendlier than others. Yes. Right? It's just true. So if you go to any of these big trade shows related to games,

or you go to even like Comic-Con, right, to expand it a little bit. But if you go to JenCon, for instance, I have not yet been from everything I've heard. And in tandem, I'll give another example. of archery, specifically bear bow archery, which we don't have to spend a lot of time on. But there are many different disciplines within archery, and the people in barebow are the friendliest.

They're happy to help. They don't have any cutthroat competitive mentality, generally speaking. Everybody helps everybody. That makes a difference. It makes a huge difference. That's like the neighborhood where you choose to raise your kids. It's like, where do you want to be? Who do you want to be around?

Because you are going to be influenced by all of that. And the gaming world, the tabletop gaming world, to be clear, I think when the stakes get higher, it gets weird, like video games, then there's a lot. The dynamics could be very, very, very, very different. Just like all the prize money for archery, or a lot of the prize money is in compound archery. And it's like, things change when you start to add in that incentive as a primary driver. Right, the people matter. Yeah, yeah. And the incentives matter.

It's like if you added the same amount of money into Barabot, I'm sure people would stop sharing their secrets. It's the money, yeah. But you probably have the same experience I've had because we both obviously had a lot of exposure to the publishing world, but also some exposure to Hollywood in like that world. And the difference, both of them, people are meaning a different way.

In Hollywood, it's like they're satirical how nice they are to you. And then behind the doors, it's so brutal. So like in Hollywood, it's always like, you know, I got to tell you, this idea is so good. I would give one of my kids away for adoption just to work with it. You have, I could die tomorrow. You have given me a reason to live. And then, you know, you never hear from them again.

It's so bad. And then you go to the publishing world dealing with Hollywood some. I was like, ah, New York-based agents. They're like almost, they're brutal, right? But at least like they're honest. They're also just as meme, they're more honest. Like, that's a dumb idea and that's not going to work and we're not going to publish it. But at least they're clear about it.

So you have different flavors of meanness. It's nice to get out of those worlds. I can see that. Yeah, for sure. I mean, I'll actually speak to that too, because games have a huge benefit that is similar to maybe stand-up comedy, and here's the benefit. If you have a passion project that's music or art or whatever,

for a lot of different types of projects, people can lie to you to be nice. Yeah. Right. If you get up in front of an audience and try to do a 30-minute set in comedy, you might get one or two courtesy laughs, but then it's going to be dead silent.

You're going to bomb, and you are going to know that your material doesn't work. With the game, if your game doesn't work, your game does not work. It really doesn't. You can tell on those game testing videos. Oh, you can tell. Even if somebody's trying to be nice,

they have that kind of plastered fake smile on you're like, ooh, that's not good. Right? Or if they're like, yeah, that's fun. Like the damning with faint praise. I mean, like, you can tell watching the, like, colors were great, Tim. The colors were great.

Yeah, I really like the size of these cards. His cards are laminated, like really smooth. Like, you have really good job, yeah. I want to take a quick break from our conversation to talk about the presenting sponsor for today's episode, reclaim.aI. Now, those of you who have heard me talk about AI, know that my big interest,

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That's reclaim.a.ai slash Cal. All right, that's cool. But now let's get back to my conversation with Tim Ferriss. A huge benefit is you will know if your baby's ugly very quickly. And you don't have to ask people for their opinion. You'll see it. And I would, just to speak to the Hollywood piece also, and maybe I'm biased having grown up in New York,

people can be brutal, and the people who are brutal are not always going to be right. But if the idea is truly bad, they just saved you a lot of time by being honest. If you pay attention to it, it doesn't mean you should just follow it, wrote. But separately, if someone's brutal to you and you fold, it means you didn't have the necessary enthusiasm or focus to have endurance pursuing that project.

So even if it's a good idea, they saved you time because you wouldn't have been able to execute in the long term on it. Does that make sense? Yeah, if they've been too supportive of a bad idea, it would have been six months later, you would have folded when it got hard. Exactly. Or if it was, even if it were a good idea, that's, I think, the thing that I'm very, in articulately trying to convey is that even if it is a

the idea could have product market fit for say a book but the book is going to take you a year and a half to write and underneath all of the surface enthusiasm you don't actually have the juice to fuel that year and a half

great idea but like execution risk right like key man risk with endurance the agent or whoever it is who insults that book or judges it really harshly, if that causes you to fold, you wouldn't have made it anyway.

And I mean, that gets into some very smoky territory where when do you listen, when do you not? And my very brief answer to that is you workshop the hell out of it in advance. You pay a lot of attention to your energy levels if it recharges you or not and know what works before you even get to the agent. I mean, this is another divergence, but why do you think a nonfiction book publishing? People don't like, not everyone, but I run into people who want to be writers who do not like the fact that the book is bought first before you write it. To me, I'm like, this is great.

Like, money is a neutral indicator of value, Derek Sivers. You don't have to put in a huge amount of effort before you get like a very definitive, okay, this could work. We're investing in it. And then, you know, and people, there's a lot of first time. writers who just don't want that to be true. What do you think's going on there? Well, tell me more about that. So with the folks who have voiced that to you,

is it that they want to follow the romantic image of the writer, come out of a cave with this beautiful diamond and then get what they're worth? Is that what they hope to do? Or is it something else? I think, well, here's what I'm trying to figure out. I think it might be, it makes the rejection. proximate. Right.

So it makes it too close. When you say to them, oh, great, all you need to do is query an agent, you could do that tomorrow. Maybe it's, I'm not ready for this to be rejected yet. I want to have a thousand words a day with the perfect, you know, Urbamoth AT that I Instagram and do this for two years. And I don't want this to be derail. I don't know if that's what's going on.

But there's such, I have these conversations with the writers all the time where they invent the most elaborate ways that they're going to get around selling the book first. And I was like, well, why not just see if the idea, maybe it's their mind knows, like, it doubts them. I'm not, but it's always a fascinating thing. I was like, this is the huge advantage we have over novelist is we find out up front. We don't have to wait until the box office numbers come back. Yeah. I would, I think that now that you're explaining it and giving some examples, it's avoiding judgment. It's avoiding feedback. And, this is where Seth Godin has so many great things to say.

And I can't remember who first said this, but no product survives first contact with customers. And what Seth would say, and I'm paraphrasing here, but he said, you know, changing the world and creating this and da-da-da-da, and doing these giant things. You can hide behind the big. He's like, find your smallest viable audience and get in front of them as quickly as possible.

Yes. And then you can't hide, right? If having three of my friends playtest, my shitty prototype is doable tomorrow. It's almost impossible for me to come up with excuses why that isn't something I can do. But if I'm like, I want to create the game that's the combination of this, this, this, this and this bestselling game, it's going to take me nine months. I have a plan and then I'll be ready to finally show it, to debut it on the stage at the World Expo or whatever. I think underneath it all. And it's often, I would suspect, subconscious,

people are just afraid of it being rejected. And for me, the problem is the label, as is often the case. It's like the labels you use and the words you use matter. They form your thinking and your beliefs and your reality. So for me, it's just feedback. It's people who are helping me make something better. That's it. That's it.

and that's like having a very rough draft and having people who care about you who have a good eye giving you feedback on that rough draft. They are helping you make something better. Now, if you're dealing with strangers, of course, they may not do it in the most delicate fashion possible, but nonetheless, they're still helping you get closer to something better. So the first contact is tough. And a lot of people may not realize, I mean, if you get good, especially in the early days at selling nonfiction books, you're basically fundraising for a startup, right? Yeah.

It's like you're putting together. There's a business model. You're putting together a book proposal. What is that? It's a pitch deck slash fundraising presentation is what it is. And a lot of the stuff you would see for people raising money for Uber or anything else. It's going to be the same stuff. How big is the market?

Yeah. Right. Do you have access to the market? What's the basic? premise. Why doesn't this exist in the market or why does it echo something that's already working? Okay, let's see a sample, right? Which would be the equivalent of like a super rough mock-up prototype. And they want to know that it is as close to a sure thing as humanly possible. And then you get this advance, aka seed funding, right, to get you to the next

milestone. And they're like, well, if this goes well, we'll have more to pay you, right? Which is paying you in installments. It's the same thing. Same idea. Whereas fiction, man, that's a tough game. I mean, having to write it first. I mean, that's, I would prefer to do it honestly because the prospect of selling a fiction book, which I could probably strong arm someone into doing if I wanted to, right? I could have some publisher cover their eyes and say, I hope you don't get me fired, right? Yeah, because you have channels. I wouldn't want to do it because the pie on the face would be so much more dramatic if it came, whatever it is, six months before this thing's supposed to be published. I'd rather just have a couple of sample chapters in there like, Tim, I love you, and this is

terrible. But good news, there are steps you can take to make it not terrible. We love you, your book about barebow archery. We get that you're passionate about it, 800 pages? I don't know. A lot in here about string density or attention or whatever. Yeah. Yeah. Yeah. So tell me if this is right or not. Like if I'm,

this is like I'm putting in an arc from afar on your life. So you can tell me if this is, this is right or not. Because I've been writing recently about this idea. I've been using a term engineered wonder. I had a recent newsletter post about this talking about Walt Disney. And there's a certain point in his career, his post-World War II, the studio was struggling.

He was in a malaise. And he went all in on, he was building a one-eighth scale model. working steam train. He went all in on this for like a couple years. And then he shut it down and like came out of that and built Disneyland. But there was like something about this activity. He was all in on something. It was like it wasn't a core.

This is the next movie we're doing as our studio or whatever. It like re-energized him. They sort of got different parts of his brain and nervous system active again that weren't before. And it led to, you know, all sorts of other stuff as well. And I was making this argument like this is important. Like engineered wonder. project you do just because my two aspects where it's fascinating and then you tend like you take it

far it can't just be i took dance lessons it has to be like you know i i want to compete and win it's not just hey i built a game to put with my friends it's like i want it and let's let's try to go all the way and do it in walmart yeah so it seems like i mean if we're looking at your life pre-four hour work week because in four-hour work week you talk about your life like right before four-hour work week, like this period where brain quicken, you stepped away and made it, like, I'm going to have a lot more time. You had a lot of that going on, right? A lot of the things you document in, like, your first book was just things that were interesting

and you pushed it really far because, like, life is, I mean, that's, that was the thesis of that book. You're doing this now as well. I mean, you have, there's cockpunch before that and you have the game and just like things that are just interesting to you, right? Like that are... You heard that right, folks. That's what it was called. Everyone knows what I'm talking about.

And there's a lot of this going on. And it seems like from afar, this is where I'm right or wrong, is that there was like a period in between where things seemed maybe a little more grinding. Yeah. I'm thinking about like when Ryan was working for you. It was like this book was successful

and there's these events we're doing and the new books were taking like forever to write or whatever. Yeah, yeah. Is there an arc there where like you're returning the engineered wonder or am I simplifying things? I don't think you're simplifying things. So I would say you are simplifying things, but you're simplifying correctly.

That's the right direction. Yeah. Yeah. So here's what I would add to that, because I think you're right. The, I've always, well, let me rewind. I think we can mine a lot of very valuable stuff from our childhood and younger lives. The obsessions that we never got tired of. I think there's a lot there

which doesn't mean oh I liked my little pony so I'm going to go strike a licensing deal with my little pony but it's like what is that what about it? Yep right and like dig in and surprisingly often I've tried this a number of times

in the last handful of years that stuff still works there's like this little genie in a bottle that you can tap if you figure out why those things did what they did Things when you were young, like really captured you, gave you those feelings of locked in fascination. Like, you plain vengeance and dragons when you're 12. Obsession, losing track of time.

Yeah. Those things still work. So for instance, in the last few years, I wanted to be a comic book penciler forever, meaning I wanted to draw comic books like Marvel stuff. And I used to get lost in art for decades. And then when I graduated from college and I got serious job and I was like, okay, that stuff's for kids. Let's move on. Like focus on the real stuff, read books by Richard Branson and this and that, the other thing. And put on some blinders.

And what I realized over time is that those activities, those time passing without you realizing it, kind of loss of the self, like the fixation on the self, dissolving away, those are, aren't optional frivolous things. And I would maybe compare them to like the, I don't know, the coal like furnace room in a gigantic ship. It's like the energy that is produced from that, preserved and produced, right? Just like the recharging and everything that that room provides

is necessary for the entire ship. It's not compartmentalized in that one area. So when you find something like this, which doesn't need to take a long time, honestly, for me, it could just be screwing around with a tutorial on YouTube with Procreate on an iPad and doing 20 minutes of drawing at some point after work, just to bookend work, right?

The shutdown complete, right? Now, typically if I do 10 or 15 minutes, it's going to turn into an hour and I'm going to be like, oh my God, I'm hungry. I totally forgot. that I was doing this. And that is like an extra four hours of sleep. It's incredible how much energy you can derive from that.

And so I would say like four hour work week, another way to chart the course would be like four hour work week, which was about, let's just call it, like per hour productivity. How do you maximize that? And then for our body, once again, about performance, but everything physical. For our chef, confusingly to a lot of people, actually a book about accelerated learning, right?

But once again, it's like how do I do more with each minute, basically? Then started extending into tools of Titans and tribal mentors where we get a little more philosophical. Maybe that's me getting older. I think it's me also realizing how much with every passing year, like how few things really matter. Again, any possible way you could assess it, but certainly just in terms of quality of life, relationship quality, the things that make humans human. And so I had the philosophical kind of stoicism angle, right? It was writing about stoicism and other schools of philosophy

starting maybe, let's call it 10 years ago. And the missing piece was just this engineered wonder that you're describing, right? I touched on edges of it. This engineered wonder awe in the last few years. like really paying attention to awe and what it does to people. There are some very interesting discussions of this in the scientific literature. And achieving that in a number of different ways, right? Immersive nature with very close friends, which I'm doing next week,

literally taking a week completely off the grid up in the mountains of Montana with a few friends, learning wilderness survival skills, carrying stuff around all day. And then also play. And I think play sounds frivolous to a lot of folks who are like, I still have places to go, things to do. And I guess my point would be like, play feeds into productivity. If I need to present it in a way that is palatable to type A people like myself, right? It's that engine room in the ship.

Your former right-hand man wrote a book about that. that. Charlie Hohn. I remember that. Exactly. Yeah. It's an influential book. Play it away.

Yeah. Charlie Hohn. Yeah. So, and it doesn't need to distract. It honestly preserves and fuels use that you can be actually better at discerning what matters, I think. Yeah. Like if you don't have time to meditate for 10 minutes, if you don't have time to play a game for 10 minutes, like you need to take a full week and sit down and do some.

hard thinking and journaling. Yeah. Right. Yeah. Because that is basically a preview of burnout and implosion, I would say, based on my lived experience and the lived experience of a lot of people in my audience. And we could certainly talk about a lot of other elements. But I do think the engineered wonder, the play, the joy, the awe, which are kind of, I would say,

kind of the ends of the spokes feeding back to something central that is kind of the same thing. It's like a constellation of all of those is incredibly valuable. And if you get a little, this is going to be a big word, folks. Sorry if this sounds overstated, but like transcendence.

And all I mean by that is you stop the me, me, me, me, I, I, song for 10 or 15 minutes. Oh my God, can that be just a revelatory experience that you can build into your life? And with all of the powers that be and teams that exist every time you open your phone to exploit the me, me, me, I, I song to make you use these things incessantly. I really think you need these moments where you are not fixated on themselves. just for self-preservation, but also just to enjoy this, as far as we know,

one-way ticket ride that we all have. I mean, it seems like there's an irony that, like, you wrote a book trying to explain to people. Because you were talking about many retirements, it was to go have these moments. Yeah, they get the helicopter ride up to the wine country in, you know, Argentina, right? Like, go to do the tango dancing, you know.

There's like, yeah, right? But write a book to tell people, about this, right? Like you said, yes, it was about getting more out of each minute, but on behalf of reducing the footprint of work. But then this seems ironic, but maybe I'm just misreading. It's a little bit ironic that writing a book, explaining other people, hey, here's what I'm doing. And I'm getting all these moments. My life is built around these moments of like transcendence and like engineered wonder. The success of that book then like took a lot of that out of your life. Because now it's like, I have to write the next one and I want to try TV and let me try this. Let me try this instead. Like it seems like,

I don't know if that's quite right, but like the ironies of the professional world is you're so successful telling people about the joys of it that they took away your time to keep doing that. I think that's true for anyone who is successful in anything to the extent that they get noticed in any way. It could be as a chef, it could be as a writer, it could be as a coder, as a programmer, like we're a really good UX designer. The thing that you love doing, right, to come back to that endurance, right, you're not only good at it, but you really enjoy doing it, which gives you all the fuel, the endurance to outlast other people who might have, hypothetically, the chops, but they don't have the, like, so you've got the love, you've got the ability, you're really good at doing something.

Before you know it, you're going to get more attention and you will almost inevitably get pulled away from that thing. So if you're the, this is just an example, it's really common in startups, but it's like if you're really good at that thing, boom, before you know it, you're a manager. And then a few years later, you're going to be like, how did this happen? My whole week is meetings. I'm not doing the thing I want to do. But if I wanted to be an independent contributor, like I'm going to have to take this big cut in my pay and da-da-da-da-da-da-da-da-da.

And then you have golden handcuffs in a way. With authors, very frequently, I'm sure you've seen this before. It's like you've created this thing while nobody's really paying attention to you. And then all of a sudden the floodgates open. And we chatted about this before recording a little bit, but this is why I have this 800-page draft. Please shoot me now. but of a book about all the ways that you can say no and the strategies I've used for the last whatever, almost 20 years,

I didn't have that toolkit because I didn't have the problem of this huge paradox of choice in the same way. So what did I do? Just like many authors, I was like, you're going to pay me to talk for 60 minutes? Hell yeah, I'll do that. And just said yes to everything.

And then you end up this like traveling salesman like George Clooney and what is it? up in the air or whatever that movie is. And you realize, this sucks. The thing that I was good at that got me here, I no longer have the space to do. Because as, I mean, you're kind of the archdeacon of deep work, right? You can't cobble together half hour here and 45 minutes there

to get what you would get out of a half day or full day of writing. You just cannot do it. At least I haven't met anybody you can do it. And this then becomes, right, the great divestiture, figuring out how to get back to these things that got you there in the first place without getting distracted by, and you're going to get distracted. So it's kind of like meditation.

Like your monkey mind is going to be like, yeah, email, porn, here's calendar. Like the argument you had with your ex 20 years ago, whatever, like your mind is going to do that. Well, if you could combine email calendar and porn, though, I think you have a startup. I think you got a unicorn. Corn. Email hub. So

that stuff's going to come up, but the point that I think it was Sharon Salzberger made this point to me, she said, maybe it was Tar Brock, I can't remember, but she said it's, you're not trying to eliminate thought. Every time you take the fishing rod and reel yourself back from those thoughts to your breath or whatever, that's a rep.

That's like doing a bicep girl. So it's like you're going to get distracted by shiny things. Every everything, at least once you set foot in this like attention UFC that is digital anything, you're going to get distracted. So the question is, how do you reel yourself back in? How do you create scaffolding and systems? And you're right.

So I have at various points been pulled away. That's going to happen. So it's just a question of how you get things in your calendar. that actually matter, right? So for me, it's like one group dinner a night with, it seems to be like three plus friends, but not too many, like, I don't know, it's called like three to six people total.

Huge quality of life. Yeah. Improver, huge, huge. Like, I can't even put any kind of number on it. And get those, if they're not in the calendar, they are not real. Like, get them booked, get the people committed. And so you can't back.

out with some lame-ass excuse because you're like watching an extra TED talk that you don't need to watch or whatever. You're on your calendar porn email. Calendar porn. Yeah. Well, can I, I kind of want to get your help on this. This is when I would probably at three of the, probably at two in the morning, you know, like in the middle of the night tonight, I'm going to buy yet another useless domain. You're like, I got to have before this interview air. It's going to be huge just in case before this podcast comes out.

most popular things out there. Well, I feel like you're ahead of me on the divestiture, right? Like, you got more serious about this. I don't know when you would say you got more serious about it. It's why I like that you were working on this concept. I feel like right now in my life, I call it the, I'm the great disappointer. And I feel like you went through this. There's your next book title.

Because the way people, which is natural, the problem is, it's asymmetric. For like an individual who's asking you for something, they're simulating just the time commitment of the thing they're asking you about. And when seeing in isolation, it's like often reasonable, or as you said, with speaking, the reward is really high. And in isolation, they're like, I don't understand why you want it. It's 60 minutes and it's some absurd amount of money. Or it's like, can't you just come by our company and just like talk about deep work for a while?

Or let's just meet up and have a coffee. Yeah, me up and have a coffee. Yeah. And they're like in isolation, it's nothing. But then it's asymmetric because there's 30 of those coming in. And then that's all you're doing. And so I feel like my speaking agent thinks I'm clinically insane. Because like I don't want to speak.

I'm like the worst speaking client. I was like I'll do three times a year. Right. Like I just say no to everything. All of our like extended circle, it's like all friends of friends are always like, why can't you just come talk about deep work? You know? And I'm always like I just I can't.

Or like I'm just saying no to everything. But it feels sort of haphazard. When did you're like when did you switch to the great divestiture? Like at some point I don't. Yeah, I started, it took different forms. So I'd say the great divestiture in terms of figuring out strategies and tools and systems for saying no or simply not seeing categories of things that I have decided I need to say no to even for a limited period of time. And you do full categories. It's just easier.

It's just easier. No speaking for six months. policy, right, no speaking for six months, zero. And if you break your own rules, all is lost. Yeah. Like, you can't. Yeah, because here's, and this is going to get into some woo-woo, like Venice slash Topanga, hand-wavy stuff.

But my experience is, as soon as you set a policy, like no speaking for six months, the best offer you have ever seen is going to come through the doors in two weeks. So you can almost like trick the universe. Yeah, you just have to be, and you just have to say, not today, say, not today. You gotta say no. Yeah, I mean, and this is literally true. Like, I literally, it just makes me think about it, getting, you know, an offer from a sultan.

And that sounds like a made-up thing, but actually I was talking to someone else who had the same offer come across. That's the type of thing that comes across. We like your book. We're bringing you out. You can, like, dance for us and, you know, whatever. And I just keep saying, well, keep adding zeros until you saying, like that type of stuff should.

I said no to that. I say, this is why my speaking agent thinks I'm crazy, by the way, is. Yeah, yeah. I'm not moved by money. But, okay, yeah. So whole category. You should write a book called Tactically Insane.

Maybe that's the next one. I like this, yeah. And, God, I mean, just brings up the Gidu Krishna-Murdy quote. Like, it is not the indicator of health to be profoundly adjusted to a sick society, something like that, right? I like this. And so in the beginning it was figuring out systems for saying no, because it was literally just like, how do I stop drinking from this fire hydrant?

How do I just get out of this flow? Because currently the inbound is so overwhelming. That had to start around 2008. Now, given the book came out April 2007, it took a while to get to, I mean, it hit the New York Times right away, but tickets number one took until August. And then as soon as that happened,

then all the offers start coming in. And then you pay the piper like six months later. six to nine months later. And then I was like, oh my God, is this my life now? Wait a second. It's like, it's a quality problem. But this is also in some ways like a very, it's a creative, it's a creatively terminal problem. Right.

Like if I keep doing this, my creativity, my flexibility, my identity becomes fixed if I keep doing this. And that's, so it wasn't until later, I tried to find ways around it, tried to find ways to massage. what I would say yes or no to. Okay, I'm going to add a, I'll keep adding zeros until people start saying no. All of those things can help, but they don't provide the psychological reprieve and the energy benefits of just categorically saying this is a no, which I also did for other things that have been like the most lucrative thing in my life, Angel Investing. In 2005, I was like, why I'm taking a long startup vacation or in parentheses, why does they know?

How does they know when it matters most? and I stepped out kind of at the peak of my powers in Silicon Valley to stop completely for three to five years probably. Yeah. And that's what allowed me to really focus on the podcast. Did you get a reprieve when you said break from books? Oh, huge, huge, huge, huge. Yeah, huge reprieve. You know you could just like not pitch a new book.

Was there something psychologically different by actually like saying to yourself, I'm not working on, I'm not just waiting to pit something next? It's like I'm not writing right now. I'm doing the podcast. And frankly, for that, that was I may not ever write a book again at that point. I was so burned out from, and this is partially my fault, certainly, but committing to do what should have been a three or four year book in a year and a half. I mean, it was an insane deadline for this book. I'm just so proud of that book, but if people look at it, I was thumbing through it. I still use a four-hour chef because it's got a lot of great recipes in addition to all the

accelerated learning stuff. And I was flipping through it and I was like, what was I thinking? Yeah. This like four color, hundreds and hundreds of photographs, maybe a thousand plus. With a brand new publishing house. Yeah, brand new publishing house. It was upsetting the entire world of publishing. Going through Amazon publishing.

I boycotted by everybody. And I decided. Wasn't BitTorrent involved for some reason? Yeah. For some of the promotion. Well, every time I do promotion, I try to learn something new using a brand new channel or something. So we did a BitTorrent bundle, which was actually super. successful with a free audio version of the 4-Hour chef and all this other stuff.

This is something like my kid's generation with like those words mean nothing to us. Yeah, a bit torrent bundle. Yeah, like with, you know, launching the game, I'm going to have one or two kind of just completely off-menu new technologies I'll play with to learn about them. And saying no to doing another book, just saying, you know what, I don't know how long this pauses, maybe it's indefinitely, was incredibly important also to

not to address the isolation and loneliness that I felt. Because even in producing that book, a lot of it, as you know, is very solitary. It's very, very, very, very solitary. And I spent so much time alone working on that book. It wasn't good for me. And I don't think it's good for

most people to be alone all the time. Very few people have, I would say, the mutation. It's not an evolved capacity. Like Robert Carrow, like some of the great, like historians who just want to be, David Grant at the New Yorker,

he wants to be in archives. Yeah, just like turning, but it's a very specific thing. I mean, that is, I really feel like, and sure there are people who are like, I've been reading so much Buddhism. I'm like, you just need to be a peace with yourself

and talk about your childhood and forgive your parents and then you can be alone and be happy at any time with yourself. I'm like, maybe, but if you talk to evolutionary biology, I think evolution drives a lot and genetics drives a lot. We are evolved to be social period, full stop.

And if Robert Caro, by any measure, is a complete mutant, right? It's kind of like if you're like, well, LeBron James can jump that high. Like, yeah, I mean, I should be able to jump that high. And you're like, let's just jump higher. Let's hold on for a second here. I mean, you are not the same, barely the same species. So similarly, after that, the biggest, psychological reprieve was spending time with more people.

And the podcast was intrinsically social. Yeah. It was having conversations with people I deeply cared about in the beginning. It was close friends. And then people I was, whose work or lives I was deeply interested in. Yeah. It had a social piece built into it.

And it doesn't have the footprint on the rest of your life. I'm writing a book now. You know, I'm never not writing a book, but man, it gets brutal. Because you want every moment of your life that you're not writing, you're a little bit worried. I probably should be writing because you're thinking about deadlines. That's the thing about writing, which is, for instance, right,

with Coyote, with this game, it's like, yes, because of the way my mind works, I thought about it a lot while doing other things. But books are a different level of preoccupation. and not preoccupation necessarily in a negative way, but when you are not writing, if you're taking a book really seriously, you are consciously or subconsciously thinking about the book. It's kind of an all-consuming thing,

at least in my experience, and it sounds like to a greater or lesser extent, your experience as well. And it has to be. It's like you can do the math. It needs about X number of thousands of hours of concentrated attention to generate enough words for the book.

So, like, you're in the red massively when you start writing a book. And, like, I have to, this needs 10,000 hours of attention or whatever the actual time is. And so it's a, it's not just, oh, it's, in a degenerate way, occupy in my mind, it really shunits, distract me by showing it. It's like, no, it, like, needs,

if I don't get another 50 hours in this week on this, I'm kind of falling behind, like how it has to have. Making my cortisol go up, just listening to you. You can tell I'm, yeah. I'm on a New Yorker deadline right now, so I had to take a step away from my book, and it's stressful every day. I'm like, these are days I could be writing.

Glutton for punishment. Yeah, you should get your Opus Day whips out. Just do that while you're saying. So I've got the thing wrapped around my leg right now, yeah. I was asked to do a speaking thing for Opus Day once. This is the back in the early days in Cambridge, yeah. Wild. Okay. Interesting.

If you haven't seen the DaVinci Code movie, you can get preview. It was exactly like that. It was exactly like that. I was very much like Tom Hanks in that movie. It was an albino who was whipping himself. It was an odd. It was just a weird speaking event. It was a weird speaking event.

It was just two of us in a room. Just in a room hitting each other with whips. But good money though. So, you know. Yeah, you know, but the money was so good. Yeah. Yeah. I remember BJ Novak, who's famous from the office, writer, director, actor,

extraordinaire. And one of his tips, this helped me to say no to a lot of stuff. actually was effectively in paraphrasing, right? This podcast was a long time ago. But whenever you say blah, blah, blah, blah, blah, blah, blah, blah, but the money's so good. Whenever there's a but the money's so good or some variation of that, that is a clear red light. Stop and take a really close look about whatever it is that you're considering doing. Yeah.

If there's an and it's different. Yeah. And the money is also really good. And the money happens to be great. That's a different thing. But the money is so good. Podcasting seems like at least it was, and then I'm going to ask you if this is changing. But it seems like the perfect refuge from that, right?

Because for whatever reason, unlike these other industries, you could just podcast and be good at it and successful at it. And people are happy to listen to your show. And there was no one, no one not. There's no scaffolding of people knocking on the door. Be like, great, now come do this time consuming thing or that time. It could just exist as a creative, skilled thing. where people were just happy for you to do this creative skilled thing. There's just not that many people.

You know, you have to deal with like ads or something like that. I mean, so did you find, I've loved it about podcasting is that. Oh, me too. No one else bothers you. Do you think it's still that?

Is it going to stay there? I mean, I'm curious about your trajectory because you were there early. Like, are you sticking around in podcasting? Are you changing? Like, well, how do you,

what's your read? You got to help me here. What's your read on what's happening in this industry? What's your relationship to it? Like, is it still going to be this great refuge for people? like semi-interverted creative people like us or is this changing?

I think it will be it can continue to be a refuge but I think it requires setting rules and policies that you've thought through very carefully at least in my case. So I found myself getting pulled into the floats and jetsam of

all sorts of things and then put out and this is one of the benefits of having a blog by the way anyone can have a blog, log, but you put out a public policy, which depersonalizes saying no to a lot of people. Because you can just say, hey, I put this up six months ago. I got to follow my own advice. Because you have an interview show. So everyone is probably saying, can I come on to, oh my God. And so I put up some new rules for podcasting to keep it interesting, something like that, and explain it.

It's like, okay, here are the rules I'm going to follow. And I was actually literally just having a conversation with one of my employees who's like the C-O-O-Produce. sort of editorial handles a lot of the podcast logistics. And we had a possible guest, great guest, but A-List celebrity and has been on before, amazing conversation. But the rule that I said in that new blog post was, I'm not doing book lunches anymore.

I won't be one of 20 podcasts to come out the same week. And because it seems redundant. And what I will do, though, Like if I'm going to consider any book, I need to record and publish three months ahead of publication. Yeah. And that rules out a million people because they don't have necessarily the forethought to do that or they miss the post or whatever. But I can still point to it. And in this particular case, this is an amazing guest who is incredibly good in conversation and at telling stories on podcast.

I mean, A plus, plus, plus. But they were definitely not going to do me any favors. So it would have been at the same time as everybody else. And I said to my producer, I just said, look, if I show people that I am not following my own rules, no one's going to respect my rules. Yeah. And rightly so. They're like, look, you had Brad Pitt on during the F1 launch like everyone else.

So like now you can have me on the talk about my ebook. Whatever it is. And which is not to. cast aspersions on anyone or what they're doing. But for me, it really comes back to like for me to continue to have the energy and the love of the game to do this long term, I just for myself realized I need to change a bunch of different rules. So another one was, for instance, I want to have a barbell approach to most guests on the show, most guests on the show, which is sort of everybody knows them or almost no one knows them, right?

But trying to stay away from like the very highest point of the, of the, bell curve distribution there. And these are kind of arbitrary in a sense, but that's rules. And sometimes there is no perfect line that you can point to. So you have to pick a line. This is true with moral judgments also and ethics, right? Sometimes it seems arbitrary, but often it's always going to be arbitrary, so you must pick a line so that you can make decisions. And it's a hell of a thing.

Podcasting, I think, will continue to be a refuge. If you want to play in the major leagues using video as a growth engine, then there are a lot of compromises compared to what you and I are accustomed to doing. and many of those compromises would require doing things that are completely antithetical to my reasons for starting and enjoying a podcast in the first place. So I have accepted that I'm going to make, this has been true for probably a number of years, significant economic compromises and growth compromises

in order to continue doing this the way that I enjoy doing it. And what that means is, I think, think for a lot of podcasts that are not fixed location TV shows. It's like to call them podcast now, it's even kind of silly. There is an audio component. Yeah, there are TV shows that have an audio feed for people who want to just do the audio. I think it will return to some of the early days, right? It'll be more like 2017, maybe, 2016, for a lot of folks.

I'm totally fine with that. Totally fine with that because I love having these conversations. And the only thing that grows without restraint is a cancer. So you've got to be careful which professional cancers you choose. And that isn't to say you can't have something very big that is very good. You can. But in my particular case, I need to be very personally interested in whatever we're talking about. At least that's my bar.

because I have all these other things. I don't need to do the podcast. It's like I've got the angel investing and the book writing and the game and I'm going to trial sorts of other hairbrain stuff. I mean, you're about to become a billionaire. You're going to get that card game money. Get that card game bank.

Yeah, yeah, exactly. Scrooge McDuck backstroking through my pool of gold coins. And it's this is also my assumption with any of these projects, whether it's the podcast, which I gave myself a graceful exit from, if needed, when I started.

I just told my audience, I'm going to try like six to ten episodes and see how this goes. And I expect I'll learn these following things, even if I shut it down. The same thing goes with the game. It's like, I have no idea what kind of doors are going to open, what type of email are going to come over the transom, what type of opportunities might kind of present themselves in one way or another. So if you were to ask me, what are you doing after the game? I have no idea.

I have no idea. I mean, I'll continue doing the podcast because having these conversations, right, seeing your face, having this conversation, just, again, coming back to evolved, what we have evolved for, it's like, it's very nourishing for me. Yeah. Like, I'm in a good mood. And. So that's why you care so much about making it sustainable for you. So you keep doing it. Like, that's the plan.

It's like you're continually looking for some kudzu has grown in. Let's trim that off because I want this to be able to keep going. Let's get the partner. What is the cutzoo? It's an invasive plant that has, like, native to the American South that is sort of taken over a lot of places. It's maybe like barnacle on the side of the sailing ship. Like, you're like, I got to get those off so this can keep moving. Yeah, yeah.

I mean, if I really think about pruning as much as adding. I love Japan. My first time ever outside of the United States was as an exchange student when I was 15, going from Long Island to Tokyo, which completely shattered my mind. in a great way. It took a long time for me to get used to being in Tokyo. But should the Japanese aesthetic to paint with a broad brush

of some of these gardens where you'll visit some of these gardens and you'll see someone on the ground with toenail clippers basically pruning away at moss, which is not to say that's what I want to do, but what you remove mattering as much as what you add. I like that.

it appeals to me not because it's minimal but because it's elegant like I love elegance in every possible form whether it's calligraphy whether it's art like a Frank Miller for instance legendary comic book

writer and artist one of the Watchmen few people in the way actually I'm making these themes up yeah that was Alan Moore he had like a dark Batman or something at some point

Yeah, the Dark Night, he did Sin City 300. Since City is what I was thinking about. He's got tons and tons. But one of the few people to be a top five writer of all time, let's just say, and a top five artist. That's unheard of. And his style has gotten more and more economical. But economical sounds like you're selling widgets.

It's become more and more elegant. Like what he can transmit with fewer lines has become more and more powerful. Do you think this is possible with podcasts? You're saying you want to get like, what is the core, like for you? It's like, if it's the conversation, there's some platonic ideal of like the interesting conversation,

like let me carve everything else out of it. Like we don't need a camera on a boon. Yeah, totally. Which I've been on those shows before. Yeah, and frankly, you can just listen to your inner animal too. It's like, what pleases you?

It seems maybe primitive, but I mean our biology has millions of years of fine-tuning pre-language. So just paying attention to that. This is super fun for me. So if I'll probably sit down, have some tea after this, maybe do some journal, I'm like, okay, why was that fun? What was it? Right?

Because Cal's a sweet, swell, smart guy? Like, that's definitely a part of it. Not to buddy you up too hard. But it's like, that's a part of it. And we have some, we have quite a bit of kind of shared history. So that's a piece of it for sure. You also see things, observe things that other people often don't, right? So the trajectory that you pointed to, like that discussion I haven't had before.

And the list could go on and on. Like maybe it's time of day. Yeah. Okay. Like before getting reactive with any kind of inbox or anything, I did this. I happen to think that's really important. Yeah. I'm also creating something before I do any management, right?

So making before you manage for me psychologically, psycho-emotionally, huge, huge thing. I don't feel like I'm just slapping duct tape on holes in a ship or putting out fires. This is something else entirely. And so paying attention to that and then testing, okay, let's follow these rules, right? And I put in the blog post of my new rules. I was like, yeah, I could revise these at any point. Yeah. These are dumb.

If they don't work, yeah, I'll change them. I'm going through life. I'm going through something similar with the podcast where we're, Jesse and I are talking about timing. And time of day is very relevant

because I'm realizing, I think the best time for me to record my show where it's just monologue is like, I think it needs to be at the end of the day. Because I was finding, like, okay, you have a show,

it's like midday. I'm prepping. We record. I can't do anything else after that, right? Like, I don't want to do anything else. I can't,

going to my email inbox after that or whatever. And so it was like crushing days. I was like, actually, this should be like the end of the day. Like we're, we record above a restaurant. There's kind of like an energy to it. Like, why don't? And then you can just be like done with work. And I was thinking like, yeah, that's the whole point is like with this medium.

Make it the way you want it to be. Like, yeah, how should it be? It should be like one day a week. It should be do it in the evening. It should be we decompress at the bar down. Whatever it needs to be. Like, why not? It's something we can still own.

Yeah. And also just interrogating what rules you are playing by that you can completely alter. Like what rules are you currently following? Let's start there. And how can you play with them? Do a two-week experiment. And you and I have landed in the same place, by the way, with, in your case, kind of the monologue. But in my case, it's like there's a reason why we're doing this conversation,

morning, like my time. and your time and then I'm recording my own show later as a bookend at the end of the day. Because I know like this is my show and doing my show can be energizing but there's a lot of heavy lifting also.

And particularly if it's very technical this is going to be a researcher and a professor and ophthalmology. It's going to be very technical. Practical but technical. So I know that after that, that's like after doing a VO2 max workout or something, I'm going to be spent. And that'll be a great place to just like wipe the sweat off my brow and have a snack and jump in the pool or something like that at the end of the day. So that's like the order matters. And over time you can just pay attention to like how your body feels.

Are you excited to hop on? I was excited to hop on and see it and catch up and just riff because I knew that it would be also. unexpected in terms of direction, which is fun for me. Not as excited as you'll be for the ophthalmologists, though, because that's going to bang right there. Well, you know, not... Actually, Andrew Huberman's an ophthalmologist, so I guess I should eat my words.

Yeah, yeah, yeah. And this, also not to turn this into a, oh, woe is me, you know, I remember back when we were youngsters, but very personal interest, right? For the last year, for the first time, I've had presbyopia, which is age-related visual decline. also interestingly because I looked it up because I was like, is that the same as Presbyterian?

Like the etymology and it is. Presbyterian is something like governed by the old, governed by elders. So the actual word origins are related. But presbyopia, it's like, okay, like looking at my phone, looking at a supplement bottle, looking at a menu and dim light,

all of that is starting to go. I'm like, I don't like it. I don't like it. I do have some glasses. Welcome to my life. Yeah, I don't want to immediately. hop to that. So, super personal.

You're swimming against the current here, Tim. I was just complaining to my wife before I got on the air here. I literally said I was at my coffee shop down the block trying to read a book. And I was like, it's too dim in there. I was like, I can't read there. Too dim. I'm sorry. I laughed because it's sad and it's true and it's also, has been my experience.

Well, I'll tell you something crazy, which it could be placebo effects. So I don't want to get too ahead of myself. But I've been experimenting with software from this tiny startup, and it is intended to train simplifying it here. But instead of doing anything to your eye structurally, it's training your visual cortex to reinterpret information and to improve your reaction speed in ways that actually change your near vision. and I've only been doing it for 26 days. It's like eight minutes a day. It seems to be helping. I've heard about something like this.

And it's different from visual education where you're training the muscles in the eyes. That's what I've heard about. Okay, this is different. It's your brain. Yeah, this is training your brain. So super interesting. I tell you what, I realize I'm swimming against the current,

but this is also kind of what I do. This is peak, too, Paris. Yeah, this is Peekton Farras. I get my kicks out of like, okay, I am going to go all in. And then I'm going to find all this stuff and I need someone to tell me if I am being a crazy person. So this interview is actually happening. Okay, I see. So I get somebody on who can be like, that's interesting. That's nonsense. Further studies needed. But like trial data actually pretty interesting. Don't do this. That's a terrible idea. You're actually going to blind yourself if you look into whatever or whatever for 20

minutes a day. Don't do that. And that's great. Okay. All right. Well, now I will look forward to that. Yeah, I'll bring the adults into the room. All right. Final question. Have you found this, because you've been at this longer than me, have you found the sweet spot for staff size? What does it take to run? I know it's confusing because you don't just podcast. But what does it take to run, you know, Tim Ferriss, allied conglomerate? Yeah. Tim Ferriss, international. Allied media. Global H. HQ. Yeah, exactly. I think that I am excessive in my fixation on leanness and elegance. I think sometimes I overdo it.

Actually, often I overdo it. But what I can say is what currently works for me after a lot of testing. And I will also preface that by saying, I think I am, and maybe this is for another call, but I think I'm a very good leader, but a very mediocre or average manager. Right. So I really require people who are incredibly self-sufficient and self-driven and who have a lot of self-inquiry, which often requires a lot of self-awareness,

and those people are just very, very, very hard to find. But you can build them from starting with simpler tasks and then cultivating that if they have the raw characteristics. You break them down psychologically. Until they're up and then you rebuild them. Yeah. Yeah. Tim Ferriss.

The training center you have, the re-education center. Yeah. Please relinquish your phone. So currently I have three full-time employees. And a lot of contractors. And I have tried to contract out as much as humanly possible. So this will certainly have echoes of four-hour work week.

Right. So my staff size compared to my business has not scaled proportionally. What I will say is contractors have, and people might say, well, what's the difference? Well, if you live in the U.S., there are a lot of differences here. There are a lot of differences. And you have to be very careful with this. You can't get cute and have full-timers who are classified as contractors. The contractors have to be doing a specific thing.

It is clearly hourly. it's But I am willing to And I'll put this in quotation marks Overpay hourly For contractors I am especially willing to overpay For

Let's just say companies Where you don't have any A single point of failure Let me give an example So there is I use an outsourced Sort of fractional family office, which handles all of my, so there's various annual fees and so on, but they handle all

of my bill pay. They handle all of my effectively bookkeeping. They handle, they can give feedback on investments, some considering. I can just float tons of stuff to them that they have a first pass on. And what's nice about that as opposed to having a single contractor, before we started recording, I was like, let me put on some backup audio. Right? And I'm recording on QuickTime just in case. So I am excessively hypervigilant. And the military has this expression, or I mean the military, but you'll get the idea. Two is one and one is none.

It's like if you have two, you're going to lose one. If you have one, you're going to have none. So always have redundancy. And I've been in a position before where do you have a key function, Let's just say it's for the podcast, could be sound editing, could be video editing, and you have a fast turnaround for whatever reason and somebody gets sick. Uh-oh. If you don't have a backup, you're in a scramble and a bad situation.

So particularly with something that is mission critical like Bill Pay, if somebody gets sick, I want to know that my profile, my information is within a system and a company such that there's a backup person. Yeah, someone can pick it up and do it. Who can swap in and handle it. So I'm particularly willing to overpay for that. And I think part of that is that I've seen the employee tail wag the dog in some cases to borrow from the tax expression, where people hire, higher and higher.

Maybe it's during like a 2020 boom cycle because there is a company that benefited from that. Or who knows? They start adding folks. but then they run into the discomfort and possible complications of firing. So they don't want to fire. So they start inventing lots of things to keep people busy. So they can, in their mind, justify the salaries they're paying. And I try to avoid putting myself in a position where even subconsciously I can be influenced by those types of incentives.

Yep. They're on the payroll. You're going to event work. And then suddenly you have. you know, you're doing live shows and you've got your selling T-shirts and... Exactly. Exactly.

So to try to avoid that, I really apply constraints, right? The beauty of constraints, whether you're writing a book, creating a game, or building a company, guess what? Like, Derek Siverts speaks on this really well with respect to CDBA.

It's like, this is your chance to try to create your version of a utopia. Yeah. Sounds maybe ridiculous, but it is. Right? Like, there's, you have to do certain things, checks and balances and dot your eyes across your T's from a legal perspective, from a health insurance perspective, et cetera.

But there's a lot of room to do things in an interesting way. I think, you know, Jason Freed and DHA 37 signals do a great job with this. Maybe they renamed it Basecamp. I can't remember. They renamed a Basecamp, yeah. Yeah. So they have some incredibly innovative ways of approaching things. Then you see like a Coinbase and like what they did and public pronouncements

and kind of excluding discussions of politics from the workplace. Like, you can do a lot within your company. So for me, just like my house, just like hopefully my books or podcasts, it's like my company is a reflection of my personality with its strengths and almost certainly with its weaknesses. I try to cover for them. I think I try to make it perhaps too aggressively like a bonsai tree. Maybe I would benefit from having an extra person or two.

but I have recognized my hyper aversion to waste means that I will also try to invent things for people to do if I feel like they have too much idle time. That's interesting. Yeah. Yeah, yeah. So contractors won't make you do that. Yeah, three employees.

Okay, that's good. Yeah, and that determines what I can do or not do. Yeah. But also that leads me to more productive solutions. Like if I had 10 people who, let's just say, a number of them were kind of off-cycle and had a lot of time. I might have tried to do a game internally. That would have been, I don't want to say a disaster,

but I would have wasted so much time. Everybody would have been learning from square one. And instead, because I've applied the constraint of keeping the company small, it's like, no, let's go collaborate. Let's somebody else who does this every day, who's A-plus at it, do that stuff. Yeah, otherwise, not that this, he loves this, but it wouldn't be good for you and I. You'll end up with, like, Brandon Sanderson's warehouse. And Brandon Sanderson loves having a lot.

He loves that stuff. I find it insane. I've talked to him, I know some of his people, but he loves it. And I'm like, oh, my God, it's my nightmare. Yeah, he loves it. Like, that's part of his art. Yeah. And I recognize that I, he also has, in his wife and other people, folks to run a lot of the logistics and other aspects.

Yeah. One thing I recognize about myself also is I have a tendency to metal. This comes back to being an average manager. You're not going to be happy with happiness. I get my hands dirty often when I probably should just leave everything alone. I'm like maybe an executive chef who's like running from station to station like, come on, come on. Let's not the right place to put the sauce.

Come on. Yeah, it's just like, you know, I got to recognize that this OCD thing is sometimes very helpful. Yeah. But also leads me to make some pretty dumb decisions. So I try to, you know, like, you know, Charlie Munger would often say and Warren Buffett too, right? It's not about being super smart. It's just trying not to be stupid.

Not to be dumb. Yeah. I hear you. Well, Tim, maybe that's a great place. That's a great piece of advice to leave it on. Don't worry about being smart. Just try not to be stupid too often. I always appreciate you.

I always appreciate our conversations. I feel like we do in both places. It's always a pleasure. And I enjoyed it. And Coyote. Coyote. Check that out. It's everywhere.

Amazon, Target, Walmart, wherever. So hope you try it. It's, it works. Yeah. People laugh. Yeah. It's a, it's a dumb game for smart people. So check it out.

And always nice to spend time together, Cal. All right. Thank you, Tim. Thanks, man. All right, so there you go. That was my conversation with Tim Ferriss. We started talking about his game. I actually have it right here.

Here's Coyote. And we went from, how do you build a game that is really good, to playing the game of life. in a way that's going to give you real meaning and depth. Have you tried this yet, Jesse? I did. I brought it to the beach.

Yeah, you took one of the copies. Yeah. It's fun, right? Yeah, it's fun. I like it. It was really cool to hear from Tim how hard it is to get one of these games perfectly calibrated. That was the cool part where you have like the prototyping and it's just tweaking this. What if we change this card to this card to that card?

It's one of those things you think it's like, oh, I could invent a card game. You realize like, oh, my God, it's so hard to make one that's fun. This is a good one. Tim is always fantastic to talk to. He's a team thinker. He sits and he thinks and he cares about living deeply in a shallow world. To me, that is what the four-hour work week is about. The four-hour work week, as much as any book, probably help set those seeds in my thinking about crafting a life that matters and that it's enjoyable and that you enjoy.

As opposed to just pursuing a particular goal or a single grand accomplishment that you think is going to solve everything. So I always enjoy going on Tim's show and it's been a pleasure to have him on mine. So thank you, Tim. Check out his podcast, the Tim Ferriss Show, which I'm sure you already know. Buy Coyote. This is everywhere, isn't it? Yeah, you can get in all stores. That guy's got it dialed in.

This is not some, you know, Patreon product or whatever. It's a Walmart. Yeah. Yeah, good for him. All right. Thanks, Tim. Thanks for listening. We'll be back next week on Monday with a normal episode of the show.

But until then, as always, stay deep. Hi, it's Cal here. One more thing before you go. If you like the Deep Questions podcast, you will love my e-mail. newsletter, which you can sign up for at calnewport.com. Each week, I send out a new essay about the theory or practice of living deeply. I've been writing this newsletter since 2007, and over 70,000 subscribers get it sent to their inboxes each week. So if you are serious about resisting the forces of distraction and shallowness that afflict our world, you got to sign up for my

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