The Exchanges

Q Why a four out of 10 day? Do you know, like, I'm always terrified of mediocrity. It's probably my biggest thing in life.

A Well, when I say four out of 10, I don't mean like the writing is a four out of 10, Or, you know, my happiness is a four out of 10. I'm saying that I just get a good hour, hour and a half of writing it, which, you know, if I'm, you know, if I look at all the days I've written in the past, there are a lot of days better than that, when I've really gotten into a three or four hour flow and written two or 3000 words. Um, that's an eight or nine out of 10 day as far as pure productivity, but there's a ton of zeros in there. A miserable zeros. Tons and tons of zeros. And so it's like, instead of having a Bunch of zeros, and then some huge days. Let's try something different, and let's try to have at least, um, you know, a mediocre productivity day every day, because that compiles, um, in, you know, eight months. You finished a book.

AI assessment note: “try to have at least, um, you know, a mediocre productivity day every day”

Q When did you start making money from it?

A Pretty soon, you know, the, the, the, it was about 10 posts in that the, that one post really blew up, and, you know, suddenly there were a decent amount of traffic after that. So we put Google AdWords, you know, on, and that generated some money, but I hated it. It was like, this is so, like, not authentic. It was not, like, in the spirit. It kind of, like, made this ugly, it's like, I feel like I created this, like, little special kind of custom Place for people to come, and suddenly there was, like, these other companies there, like, with their cheesy ads. I was like, get out of here. So, um, that stopped, and we turned to Patreon, um, to try that at the, uh, urging of a friend of mine, Philip Detmer from Kurzgesagt. He was like, you gotta just do it. So I tried it, and, um, it was great, and that, that's been a nice support ever since. And then, you know, when you have enough readers, you can start to supplement with stuff. We have merch. We started selling things, um, started doing some speaking, you know. So it's like, you know, you can, you can, there's a lot of ways to kind of cobble together revenue once you have a decent following.

AI assessment note: “Pretty soon, you know, the, the, the, it was about 10 posts in”

Q Why a four out of 10 day? Do you know, like, I'm always terrified of mediocrity. It's probably my biggest thing in life.

A Well, when I say four out of 10, I don't mean like the writing is a four out of 10, Or, you know, my happiness is a four out of 10. I'm saying that I just get a good hour, hour and a half of writing it, which, you know, if I'm, you know, if I look at all the days I've written in the past, there are a lot of days better than that, when I've really gotten into a three or four hour flow and written two or 3000 words. Um, that's an eight or nine out of 10 day as far as pure productivity, but there's a ton of zeros in there. A miserable zeros. Tons and tons of zeros. And so it's like, instead of having a Bunch of zeros, and then some huge days. Let's try something different, and let's try to have at least, um, you know, a mediocre productivity day every day, because that compiles, um, in, you know, eight months. You finished a book.

AI assessment note: “instead of having a Bunch of zeros... Let's try to have at least... A mediocre productivity day”

Q have to ask about the AI article before we do a quick fire. As I said, I studied it years ago to hopefully get a job and venture. It worked well for me. When you look back on the piece, it was 2015. So much has changed eight years on. What do you think you got right with the piece? I'm sure you've reflected on it a lot, especially recently.

A Um, I think that the general principles are pretty much correct. Um, I think, um, you know, the concepts that there's narrow intelligence and general intelligence and, you know, artificial super intelligence and that, and that the implications of the danger of these things are intense and that they, uh, AI is probably gonna be dangerous not because It's going to be evil Terminator robots, but because it's going to be super powerful with unintended consequences, um, I think, oh, that holds up pretty well. And, and, and, and to be clear, very little of that was my own research or principles. I, I was, I had a few major sources there. I had Nick Bostrom, Ray Kurzweil, and James Barat, and, you know, Elie Azurkowski, a handful of the, you know, of, of people who basically I synthesized what they were saying, and I tried to tell, you know, just, Distinguish which camps were, were rich and, um, what we, you know, which is again, part of my job is, is not necessarily to do the deep, deep research and actually come up with the original theories, but to try to summarize what the experts are saying and, and, and try to give a bird's eye view of what they're all saying, you know, and what, where is the, where is their agreement and disagreement? What's the best case scenario and worst. So I think it did its job. I'm proud of that piece. I think it holds up pretty well. Obviously, um, it's…

AI assessment note: “I think that the general principles are pretty much correct.”

Q Oh, I mean, you are very kind. I stalked the shit out of you, so I'm ready for this, but I hate shows which actually start conventionally, and so I want to start with a bit of a weird one, but think back to when you were a child. What did you want to be when you grew up?

A Well, I think it depends on the age. I think, like, Five, you know, six, I would have, it would have been something to do with space or dinosaurs. Those are my two obsessions then. Um, so probably just, you know, oh yeah, astronaut, something like that. Then, um, I think, you know, by the time I was 1314, 15, it was like I wanted max attention. So like president, uh, like it was just like hyper, hyper ambition, like want max everything, you know, and president or something like that. Um, and then that, I think, dissipated by, I was actually the class president at 17, and that was the end of me wanting to ever be a politician. Um, I was like, this is, this is not.

AI assessment note: “Five, you know, six, I would have, it would have been something to do with space”

Q Which piece do you receive the most pushback on, the most critic?

A Oh, without question, um, my stuff on, the stuff on this last book I wrote, and the series before, just anything to do with American politics. Um, there is not any single thing you could write about American politics that some people won't hate in America. Hate. So, um, for without question, you know, just wading into the world of politics and political tribalism, um, you know, again, I think a lot of people like those things. I think it clicked well with most of my audience, but there's a lot of, Um, I'm so disappointed this coming from you. I used to, you know, I used to respect you. There's a lot of that. Um, and, and you know, that's okay. Like, it's, it's okay. It's, I, I, I'm sad. I'm like, I wish, I wish all the readers liked it, but like, it's, it's, um, you know, it's inevitable. And, uh, and that's, you know, you don't get into the, you don't write about politics if you can't handle some of that.

AI assessment note: “Oh, without question, um, my stuff on... just anything to do with American politics.”

Q have to ask about the AI article before we do a quick fire. As I said, I studied it years ago to hopefully get a job and venture. It worked well for me. When you look back on the piece, it was 2015. So much has changed eight years on. What do you think you got right with the piece? I'm sure you've reflected on it a lot, especially recently.

A Um, I think that the general principles are pretty much correct. Um, I think, um, you know, the concepts that there's narrow intelligence and general intelligence and, you know, artificial super intelligence and that, and that the implications of the danger of these things are intense and that they, uh, AI is probably gonna be dangerous not because It's going to be evil Terminator robots, but because it's going to be super powerful with unintended consequences, um, I think, oh, that holds up pretty well. And, and, and, and to be clear, very little of that was my own research or principles. I, I was, I had a few major sources there. I had Nick Bostrom, Ray Kurzweil, and James Barat, and, you know, Elie Azurkowski, a handful of the, you know, of, of people who basically I synthesized what they were saying, and I tried to tell, you know, just, Distinguish which camps were, were rich and, um, what we, you know, which is again, part of my job is, is not necessarily to do the deep, deep research and actually come up with the original theories, but to try to summarize what the experts are saying and, and, and try to give a bird's eye view of what they're all saying, you know, and what, where is the, where is their agreement and disagreement? What's the best case scenario and worst. So I think it did its job. I'm proud of that piece. I think it holds up pretty well. Obviously, um, it's…

AI assessment note: “I think that the general principles are pretty much correct.”

Q day listening to you on This Week in Startups with Jason, uh, who we both like very much. You said of its ability, and this is AI's ability to shape civilization to its core. As you've thought about it over the last eight years, and now seeing it come into fruition more than ever, how do you think about the most dominant ways AI can shape civilization to its core?

A I mean, civilization is just a bunch of people with a certain shared set of understanding of the world and certain set of norms and, and, and processes and systems, institutions that we all share trust in. Um, and that is the, the kind of, uh, those are the support beams of the house we're in. And, um, AI can, is a giant seismic You know, asteroid landing in, in, in a fairly fragile set of equilibria, and it can just, um, it can very quickly, you know, what if we, no one can trust a video anymore? Every video might have been AI, might be real people. No one knows, you know, you're listening to, you're seeing a tweet, you're listening to a podcast or a talking head on Zoom on a TV interview, and you have no idea if that's a real person or not. I mean, There's a lot of assumptions that we, um, that we all take for granted that, that create a lot of stability. And so when suddenly a lot of the, yeah.

AI assessment note: “no one can trust a video anymore? Every video might have been AI”

Q Do you worry that to scale your revenue and scale your media business, you lose the constraint-free life that you craved? That's the exact position that I am.

A Well, that's why we haven't actually, I've been pretty resistant to doing too much that's focused on revenue. Because of that. Like, I just, and the same reason that, you know, I, we, six years ago, we hired Alicia, uh, who's the manager of lots of things, uh, which is just like the second in command at Wait But Why and does a little of everything. And that's about it. I was just like, I don't want a big team. And, you know, yes, we could have more money if we had more people writing, if we had a podcast production studio, you know, we can do those things under this brand. But I just kind of resisted that because I just want to be able to, like, indulge my curiosity full time and, and, and work on stuff. Um, Yeah.

AI assessment note: “I've been pretty resistant to doing too much that's focused on revenue. Because of that.”

Q what I mean by that is people often think that it's like, I did this interview, and it went bang, and then it went flat, and then I did this interview, and it went bang. And it's not true, really, actually. There was no, like, bang moment. It just gradually compounded over time. Was yours quite stack, kind of staccato, up, flat, up, flat, or was it much more linear?

A Yeah. Um, ok so, it's not exactly, like, the extreme is like, it's right angles, it's like straight up flat, straight up flat, right? And then versus the other extreme is a perfect diagonal. Um, I would say I'm in the middle where it's like, a steeper diagonal after something, after a big post, or sometimes it's, sometimes it's a tweet. You know, sometimes I'll, I'll put out a tweet that happens to go super viral, and a bunch of new Twitter followers come in, and then like the blog Um, traffic spikes. And then most of those people will come and then forget about, even if, even if they like what you're, what they see. But the people that happen to love it, they'll stay. And now like, it's like, so it's like, it's like a spike. And then when the dust settles, like the, the base number is a little higher. So there'll be those steeper moments, but then it's never totally flat because specifically because of the nature of wait, but why is the, like you mentioned like certain posts that are, um, Um, evergreen that are Um, they're kind of out there being salesmen all the time. So like, there's always some traffic on the really popular posts, even years after they're written. Um, and there's, you know, uh, so, so when you put work out like that, it's always, um, it's always going to be building your audience. Your audience is gonna be kind of, you know, building on its own, or people a…

AI assessment note: “I would say I'm in the middle where it's like, a steeper diagonal”

Q Can I, I, I actually never spoken about this, but I've never had the chance to with someone, um, in this position. When you think about the revenue makeup of the business today, what does it look like in terms of Patreon to merch to speaking? I'm happy to also share mine and share ours if interested.

A Yeah, sure. Yeah. Um, Uh, Patreon, trying to, it's hard to remember the exact percentages, but like, Patreon, you know, is bigger than merch, partially because we just haven't made that much new merch recently, um, but there's always, you know, there's always patrons, new patrons, um, and, um, and speaking on a really good year can be, you know, um, bigger than both of them combined, uh, and then, you know, COVID, that, that goes away, so that goes on and off, and then, um, Just put out a book for the first time. So that was a nice, like one off big, you know, chunk of revenue. Um, that's, you know, so, um, but you know, but part, part of the, the, the.

AI assessment note: “Patreon is bigger than merch... speaking on a really good year can be bigger”

Q topic is too complex or intellectually challenging, intense for a broad audience? When you talk about metabolism there versus whatever it was that you were talking about, I got no idea. Now, it may be intellectually interesting past a certain level, but unlike the zeitgeist of AI, crypto, climate change, hot topics of the day, it's almost too intellectually challenging for an audience. Is that ever a question for you?

A No, because this is, this is my job. So now my job, you know, basically as I read, right? So, you know, again, if I'm really trying to write a book chapter or good blog post, I'll read, you know, five or six books, maybe, maybe more. I'll skim through chapters of other books and a bunch of papers and YouTube, whatever. It's a lot. And along the way, you come across a perfect metaphor. That's a dopamine hit, you know, and I'm either going to use that metaphor and credit the person, or I, I have, I have my different version of, of, of, I, it, it stoked a metaphor that, you know, That made me realize I have a better metaphor for this that I'm going to use, but I will note all these like dopamine hit moments. I'm like, oh, that, that clicked, right? That's important. And at the end, basically my job is to, there is something, the origin of life is officially interesting, right? And now the question is, how deep do you go? So if you go, if you don't go deep enough, Now, most educated people, like, you're not teaching them something too new, and it's actually not that, you know, you know, if you're just saying that there was a molecule that had the property of self-replication, and that started happening, and sometimes it would replicate incorrectly, and then that was variation, and before you know it, there's, like, Darwinian evolution, and that leads to all of the animals we see to…

AI assessment note: “No, because this is, this is my job.”

Q Do you feel like you're selling your soul speaking? I've had many opportunities.

A No, I don't actually, because, because I don't, um, I don't say anything that's not, it's basically just me taking what I write in my blog. And translating it to a different medium, just speaking medium. I'm never going to, I'm not going to get up there and like speak. Um, I'm not going to do what the conference wants me to do. If they, you know, I mean, I'm not going to, if they say, you know, we want you to promote this company. I'm not going to do anything like that. I'm going to basically something like, you know, AI or the Fermi paradox you mentioned. Um, I'll go if, if, you know, if, if there's a topic that I've written about that, uh, that a conference wants me to speak about, I'll just go and do the talk version and their slides. And, um, you know, I did that with a Ted talk with my procrastination post. So that's why I don't feel like, I feel like it's just a way. It's like, um, it's like taking content that if I write this AI post, it actually doesn't make much money because it's just on a blog. If I now go do a bunch of talks on AI, to me, that's like, that's the way that, that the, all the work I did for that AI post actually can turn into revenue. It's like, it comes later in form of speaking.

AI assessment note: “No, I don't actually, because, because I don't, um, I don't say anything”

Q Tim, do you feel claustrophobic in relationships? It's like speaking to a mirror.

A I mean, actually, I don't in relationship. Well, I don't know, because I wasn't in many relationships until I met my wife. Um, and so, I'm not claustrophobic with her at all. Um, you know, we're just, there's, we're very on the same page about, you know, we're both very independent. We also like, like, kind of just coexisting in the same place, you know, but she's like very, um, Uh, very open to me, just like really deep. If I need to focus on something like that, that's always okay. And like, so I don't feel claustrophobic in this, so I don't know if I would feel claustrophobic. I think, yes, I think if I were in a relationship where she was like, okay, it's like, you know, five PM, like let's works over for the day. Let's go do something. And we're like, you know, it's, it's, it's like Saturday. We don't go on the computers on Saturday. I think I might want to like, yes, I might want to run away. I don't, that's not my situation. So, um,

AI assessment note: “I don't in relationship... I'm not claustrophobic with her at all.”

Q topic is too complex or intellectually challenging, intense for a broad audience? When you talk about metabolism there versus whatever it was that you were talking about, I got no idea. Now, it may be intellectually interesting past a certain level, but unlike the zeitgeist of AI, crypto, climate change, hot topics of the day, it's almost too intellectually challenging for an audience. Is that ever a question for you?

A No, because this is, this is my job. So now my job, you know, basically as I read, right? So, you know, again, if I'm really trying to write a book chapter or good blog post, I'll read, you know, five or six books, maybe, maybe more. I'll skim through chapters of other books and a bunch of papers and YouTube, whatever. It's a lot. And along the way, you come across a perfect metaphor. That's a dopamine hit, you know, and I'm either going to use that metaphor and credit the person, or I, I have, I have my different version of, of, of, I, it, it stoked a metaphor that, you know, That made me realize I have a better metaphor for this that I'm going to use, but I will note all these like dopamine hit moments. I'm like, oh, that, that clicked, right? That's important. And at the end, basically my job is to, there is something, the origin of life is officially interesting, right? And now the question is, how deep do you go? So if you go, if you don't go deep enough, Now, most educated people, like, you're not teaching them something too new, and it's actually not that, you know, you know, if you're just saying that there was a molecule that had the property of self-replication, and that started happening, and sometimes it would replicate incorrectly, and then that was variation, and before you know it, there's, like, Darwinian evolution, and that leads to all of the animals we see to…

AI assessment note: “No, because this is, this is my job.”

Q we think about, kind of, making something your readers love, we've mentioned the incredible research that you do, how you bring it all together. Now we need to get to the writing phase. What does the writing process look like for you? Literally, like, where do you do it? How long does it take? How do you do it? Does it differ by article? Can you take me to that?

A Yeah. Well, man, I mean, so blog posts is one way, right? It's like, I would have done all my research. I've learned the shit out of the topic, right? Or I've, I've, or I've like built the framework in my head for how I want to explain this psychological thing or this thing in society or whatever. And I've, I've toiled over the outline and I, and I, and I have, I know what I need to know and I have this, the plan and now I'll go right. Um, and that, you know, I don't know, I'll write, I can, I can usually pound out, I can have some paper, you know, Pretty big days there. If I have a, if I have a deadline I've imposed on myself, and I say, this post is going to be up Friday, then I can, like, probably write two or 3000 words a day, Thursday and Friday, and get it up, you know. My last book, my, my first real book that I just published in February, um, I tried to basically do it that way, to plan and research everything and then write, and that was just not okay. That's not how you do it. So, um, it's just too big, a book. You have to kind of read and research and outline and write all kind of intermingled as you go, at least for me. I'm sure some writers can do it the other way, but, um, uh, but, but so now I'm, um, so I think, I think blog post is a, is a, is a small enough thing that I think I can just kind of like get into a Multi-day flow, when you're just, um, Like my wife …

AI assessment note: “probably write two or 3000 words a day, Thursday and Friday, and get it up”

Q Tim, what do you know now that you wish you'd known when you started? There's a lot in terms of our growth that I wish I'd known. What do you know now that you wish you'd known?

A Um, I, I guess I just wish I had known, um, my, uh, Like I've gotten much better at managing my own issues. Like I wish I'd taken my own issues dead seriously from the beginning and been like, you know, the first year or two, there was such excitement and such pressure to be consistent that like that was an external deadline. But when there's less of that, um, like I just described, I would go and hit a snag and it's like three weeks. Now, I feel like I've gotten way better at managing my own situation. So, um, like, if I have to do a certain amount per day, or else I have to pay my friends a whole lot of money, um, and they can see the Google Docs, so, like, it's no way, no way to hide. The snag just doesn't last that long. You just push through it, you force through it. So, I've learned a lot of mechanisms like that, um, that are helping me be, like, a lot more productive and a lot less miserable during this process, because, like, it's, Yeah.

AI assessment note: “I wish I'd taken my own issues dead seriously from the beginning”

Q day listening to you on This Week in Startups with Jason, uh, who we both like very much. You said of its ability, and this is AI's ability to shape civilization to its core. As you've thought about it over the last eight years, and now seeing it come into fruition more than ever, how do you think about the most dominant ways AI can shape civilization to its core?

A I mean, civilization is just a bunch of people with a certain shared set of understanding of the world and certain set of norms and, and, and processes and systems, institutions that we all share trust in. Um, and that is the, the kind of, uh, those are the support beams of the house we're in. And, um, AI can, is a giant seismic You know, asteroid landing in, in, in a fairly fragile set of equilibria, and it can just, um, it can very quickly, you know, what if we, no one can trust a video anymore? Every video might have been AI, might be real people. No one knows, you know, you're listening to, you're seeing a tweet, you're listening to a podcast or a talking head on Zoom on a TV interview, and you have no idea if that's a real person or not. I mean, There's a lot of assumptions that we, um, that we all take for granted that, that create a lot of stability. And so when suddenly a lot of the, yeah.

AI assessment note: “what if we, no one can trust a video anymore?”

Q Okay, so what piece of content has been most transformative to your thinking?

A Um, oh, in general, wow. Um, um, I always like to cite, like, The Fountainhead as a book that, um, crystallized a really important concept in my head. It's, uh, about reasoning from first principles versus reasoning by analogy. Um, I think it's a great book, and people should read it. Um, um, and then, um, uh, And then, like, I've been really, I've had my whole worldview kind of, um, like, clarified and sharpened by listening to great history podcasts over the last few years. You know, Dan Carlin's Hardcore History, um, William something, I forget his first name, Stroud's History of English, um, uh, uh, again, I'm forgetting his name, but Fall of Civilizations, um, You know, so there's, I love history podcasts, um, and I've been, like, I feel like I've learned a ton from those and just feel like everything's a little clearer after having listened through to hundreds of hours of good history podcasts.

AI assessment note: “The Fountainhead as a book that, um, crystallized a really important concept”

Q I always say, I always say also whatever time you spend creating content, you should spend the same time or more distributing. How do you approach content distribution today? You press publish. What then?

A So if it's a blog post, honestly, we're not, like, we could be doing better at this. Like, I think, you know, right now, if it's a blog post, I'll publish something, and then I'll probably, like, pull out a bunch of potential, like, I'll pull out into a folder a bunch of things for, this is a bunch of good Instagram posts that can come out of this post. Here's a bunch of tweets, and Alicia might publish them over the next couple weeks. For the book that I published, like, we pulled out a bunch of potential, a bunch of social content that can be, you know, done for the book. But, but, but basically on day one, we have a very specific regimen, which is, um, publish, uh, then Basically put out a tweet, Facebook, Instagram, and send it to the big email list. Email list is the biggest thing for us. So send it there. Um, and then, uh, yeah. Patreon, you know, let page, we usually let patrons know the night before, right, right. When it comes out, be a little before everyone else. And, um, and that's about it, you know? And then after that, like, you know, what are some, you know, some, some extract some social media posts from this post for the next couple of weeks. I think other people probably are better than we are at this. Uh, I think again, once we have a podcast, okay, now it's, it's pretty obvious to make like video clips and post them on those places. Uh, you know, so we'll d…

AI assessment note: “publish, uh, then Basically put out a tweet, Facebook, Instagram, and send it to the big email list.”

Q Do you feel like you're selling your soul speaking? I've had many opportunities.

A No, I don't actually, because, because I don't, um, I don't say anything that's not, it's basically just me taking what I write in my blog. And translating it to a different medium, just speaking medium. I'm never going to, I'm not going to get up there and like speak. Um, I'm not going to do what the conference wants me to do. If they, you know, I mean, I'm not going to, if they say, you know, we want you to promote this company. I'm not going to do anything like that. I'm going to basically something like, you know, AI or the Fermi paradox you mentioned. Um, I'll go if, if, you know, if, if there's a topic that I've written about that, uh, that a conference wants me to speak about, I'll just go and do the talk version and their slides. And, um, you know, I did that with a Ted talk with my procrastination post. So that's why I don't feel like, I feel like it's just a way. It's like, um, it's like taking content that if I write this AI post, it actually doesn't make much money because it's just on a blog. If I now go do a bunch of talks on AI, to me, that's like, that's the way that, that the, all the work I did for that AI post actually can turn into revenue. It's like, it comes later in form of speaking.

AI assessment note: “No, I don't actually, because, because I don't, um, I don't say anything”

Q I find sometimes the best shows performing wise because they feature I'm not saying Elon Musk, I haven't had him on the show, but like, because you feature Neuralink or Elon, and it's a well-known name and brand association, or it's AI, or it's crypto, or whatever that is, versus what actually is natural and interesting. How do you think about that juxtaposition between the interest and the chasing viral?

A I think, um, it's not that I don't chase viral anymore, um, but I'll do it, it, it, it has to also go a lot. For example, crypto would have been a perfect post. I know it would have been viral at the moment when I, it was right at the heat when everyone was talking about crypto, and I got a lot of requests to write about it, and I just know people just were dying to learn about it. I could have, like, dug in for two weeks, read everything, talked to a bunch of people, written, like, the full crypto explainer, But I just didn't want to. Um, and I think early on, if I knew that I had almost a guaranteed, you know, you know, million people in the first few days, viral posts, um, I would have done it, right? It was just then it was like, Take that. Amazing. People are gonna, but I think, um, you know, I, I, I, I built up a readership now where it's like one viral post doesn't do that much for that readership. And I kind of already have what I was, what I wanted during those early days was a regular sizable readership. So now that I have that, it's just less, yeah, like it's, it's much more about like what I, my, my motive, um, my internal motive is always just, like I said, excitement, something that I, I think would be fun. My external motive now is more about, like, the existing readership and putting out something that they love. Like, that's, that's great. Like, if I think, lik…

AI assessment note: “my internal motive is always just, like I said, excitement”

Q Tim, what do you know now that you wish you'd known when you started? There's a lot in terms of our growth that I wish I'd known. What do you know now that you wish you'd known?

A Um, I, I guess I just wish I had known, um, my, uh, Like I've gotten much better at managing my own issues. Like I wish I'd taken my own issues dead seriously from the beginning and been like, you know, the first year or two, there was such excitement and such pressure to be consistent that like that was an external deadline. But when there's less of that, um, like I just described, I would go and hit a snag and it's like three weeks. Now, I feel like I've gotten way better at managing my own situation. So, um, like, if I have to do a certain amount per day, or else I have to pay my friends a whole lot of money, um, and they can see the Google Docs, so, like, it's no way, no way to hide. The snag just doesn't last that long. You just push through it, you force through it. So, I've learned a lot of mechanisms like that, um, that are helping me be, like, a lot more productive and a lot less miserable during this process, because, like, it's, Yeah.

AI assessment note: “I wish I'd taken my own issues dead seriously from the beginning”

Q background. I always think that one is running from and towards something, and that our backgrounds shape a lot of how we are today, and I know it's kind of armchair psychologist, but you know, I'm a venture investor, so we have a lot of time to think. Um, my question to you is, what do you think you're running from, and what do you think you're running towards, Tim?

A I'm probably running for, okay, you know, you spend your whole, for me, my whole first 22 years, um, some people a lot longer, um, you know, with, like, like, you're, you're, you're, you're not in charge of your own day, like, you have to go to class at this time, you have to turn in this paper by this time, you have to, you know, and then it's like the summer, and you're expected to do this thing, and then you have to take this standardized test, and then, like, you know, you have to go to this practice that your parents make you, you know, and I think I hated that, Um, a lot. And, um, even then at camp, you know, I loved camp. It's not like I hated school or camp. They were fine. But like, then you go, I'd go to camp over the summer and still it was like, now we're going to soccer. Now we're going to basketball. Now arts and crafts. And it was like, I think, um, running from like that, uh, I feel like is a lot of my life has been like since then has been basically centered around not having like total free, you know, just having as much freedom as possible to the point where now, if I have Anything on my schedule, you know, for five PM that day I have something that's like the whole day is kind of like I'm in a bad mood the whole day about it because I just want like total freedom.

AI assessment note: “running from like that... centered around... just having as much freedom as possible”

Q Have you ever had it where you thought a topic would be interesting, but post research, it is not as interesting as you thought?

A Yeah, because some topics are, you know, I, it's like I thought they were, I'm trying to think of examples of this, like, well, as I'm saying, usually, usually if you just get to the right level of depth, it is, I'm trying to think if there are topics that are just not interesting anywhere in the level of depth, and I don't know, I mean, I, I'm not sure I can think of that many topics that, um, That I would research in the first place, where I know that there's something that seems interesting to me, where there's not anything interesting there. Again, sometimes the, the depths of it are very boring, and sometimes, um, um, but, you know, but that, that is, you know, as a writer, I do, I will, I do a lot of filtering, so there'll be, yeah, there will be subtopics, um, uh, you know, I was just, um, I don't know, I was gonna put a section in my book about ice ages, and, and why they happened, and then I realized it's like, it's so, I mean, I'm still researching this, but I was like, this is so, um, Complicated. It's actually not. I thought it was because, like, the sun is just angled, you know, the earth angles this way every 26,000 years, and it changes, and I'm like, no, it has to do with, like, all this chemical stuff from the earth, and it has to do with the atmosphere, and I'm like, ah, I'm, I, if I feel bored, then I feel like I'm, like, then I'm back in, like, a boring high…

AI assessment note: “I was gonna put a section in my book about ice ages”

Q Which piece do you receive the most pushback on, the most critic?

A Oh, without question, um, my stuff on, the stuff on this last book I wrote, and the series before, just anything to do with American politics. Um, there is not any single thing you could write about American politics that some people won't hate in America. Hate. So, um, for without question, you know, just wading into the world of politics and political tribalism, um, you know, again, I think a lot of people like those things. I think it clicked well with most of my audience, but there's a lot of, Um, I'm so disappointed this coming from you. I used to, you know, I used to respect you. There's a lot of that. Um, and, and you know, that's okay. Like, it's, it's okay. It's, I, I, I'm sad. I'm like, I wish, I wish all the readers liked it, but like, it's, it's, um, you know, it's inevitable. And, uh, and that's, you know, you don't get into the, you don't write about politics if you can't handle some of that.

AI assessment note: “Oh, without question, um, my stuff on, the stuff on this last book I wrote”

Q Okay, so what piece of content has been most transformative to your thinking?

A Um, oh, in general, wow. Um, um, I always like to cite, like, The Fountainhead as a book that, um, crystallized a really important concept in my head. It's, uh, about reasoning from first principles versus reasoning by analogy. Um, I think it's a great book, and people should read it. Um, um, and then, um, uh, And then, like, I've been really, I've had my whole worldview kind of, um, like, clarified and sharpened by listening to great history podcasts over the last few years. You know, Dan Carlin's Hardcore History, um, William something, I forget his first name, Stroud's History of English, um, uh, uh, again, I'm forgetting his name, but Fall of Civilizations, um, You know, so there's, I love history podcasts, um, and I've been, like, I feel like I've learned a ton from those and just feel like everything's a little clearer after having listened through to hundreds of hours of good history podcasts.

AI assessment note: “I always like to cite, like, The Fountainhead as a book that, um, crystallized”

Q Why do you think that is? I'm the same as you, but why do you think there is that unwillingness to be constrained?

A I mean, I think that that's, that's, you know, I think part of what is, you know, the part of me that hates that is not necessarily, like, I think there's something to freedom and having actual choices that are yours and not, you know, so I think there's something important there, but I think more for me is, honestly, there's, you know, I always think of those two characters, there's this rational decision maker, this kind of a grownup, and then there's the instant gratification monkey in your head who just wants to, like, maximize the ease and pleasure of the current moment, and I think Uh, I think it's a lot that monkey that hates that. And, and I think that that's why, you know, to get to your other question, what are you running to? I think, you know, designing everything to not have to have the monkey be upset by saying, I don't want to go do this thing. Even though the other part's like, you should, it's good for you to go. You should have to go do this thing. It's like, once we're there, we're always happy and better than sitting around doing nothing. So I think you can go too far. And then if you don't have any of those external structured things, then you end up in a, Um, you can end up with the monkey kind of running your whole life suddenly. So now it's like, you're actually like the monkey is making the decisions, which is actually worse. So what am I running to? I …

AI assessment note: “I think it's a lot that monkey that hates that.”

Q Do you work best in morning, in evening, with coffee, in sitting room, on laptop, on iPad? What's the, like, take me to the magic.

A Honestly, that can be, for me, I like the computer, whether it's on my, uh, monitor, external monitor, which is, uh, you know, the, uh, 32 inch monitor in my apartment, or it's on my laptop. They're fine. The monitor's a little nicer and like a nice chair. It's like, great. But, Laptop is fine. I can have my workflow. I'm good with the keyboard shortcuts. I can, like, small screen. I can still do my thing. Um, iPad is good for, for me for reading Kindle research and highlighting, and that's about it. Because if I can't easily just while, you know, reading something, just like, boom, idea, keyboard shortcut to the doc, like, type it in, and, uh, it's just, to me, it's like now getting too, um, I don't know. Maybe it's, like, maybe I think someone who's better with, like, iPad apps, specific, like, apps that are made for both iOS and macOS, like, could do it better, but I don't like, and then phone, like, disaster. I can never, like, I can never, like, work on the phone other than, like, listening to an audiobook for research or something. For me, it's, it's, yeah, it's gotta be the computer.

AI assessment note: “For me, it's, it's, yeah, it's gotta be the computer.”

Q I always say, I always say also whatever time you spend creating content, you should spend the same time or more distributing. How do you approach content distribution today? You press publish. What then?

A So if it's a blog post, honestly, we're not, like, we could be doing better at this. Like, I think, you know, right now, if it's a blog post, I'll publish something, and then I'll probably, like, pull out a bunch of potential, like, I'll pull out into a folder a bunch of things for, this is a bunch of good Instagram posts that can come out of this post. Here's a bunch of tweets, and Alicia might publish them over the next couple weeks. For the book that I published, like, we pulled out a bunch of potential, a bunch of social content that can be, you know, done for the book. But, but, but basically on day one, we have a very specific regimen, which is, um, publish, uh, then Basically put out a tweet, Facebook, Instagram, and send it to the big email list. Email list is the biggest thing for us. So send it there. Um, and then, uh, yeah. Patreon, you know, let page, we usually let patrons know the night before, right, right. When it comes out, be a little before everyone else. And, um, and that's about it, you know? And then after that, like, you know, what are some, you know, some, some extract some social media posts from this post for the next couple of weeks. I think other people probably are better than we are at this. Uh, I think again, once we have a podcast, okay, now it's, it's pretty obvious to make like video clips and post them on those places. Uh, you know, so we'll d…

AI assessment note: “basically on day one, we have a very specific regimen, which is, um, publish”