Tim Urban: How "Wait But Why" Grew to 600k Readers; AI's Revolutionary Impact on Media | E1048

1. 0:00 – 0:49

   Intro

   1. TUTim Urban0:00

      We really need well-known media brands or personalities or science institutions that we all can say, "Well, if they're saying it, then it's probably true." That creates a shared reality. We already see, of course, the fracture of the shared reality 'cause of tribal narrowcast media, you know, each telling their own story, and social media creating bubbles of reality, and I think AI can just accelerate these trends.

   2. HSHarry Stebbings0:22

      Tim, I am so excited for this. As I just said to you before, I've been a big, big fan of your writing for many years. I just mentioned that I actually tried to pass some of it off as my own intellect on AI about seven years ago and it worked.

   3. TUTim Urban0:34

      (laughs)

   4. HSHarry Stebbings0:34

      So, I owe you for that, but thank you for joining me.

   5. TUTim Urban0:37

      Yes. Thank you for having me.

   6. HSHarry Stebbings0:40

      No, that's cool.

   7. TUTim Urban0:40

      And for being so well-prepared.

   8. HSHarry Stebbings0:41

      Oh, I mean, you're very kind. I stalk the shit out of you, so, uh-

   9. TUTim Urban0:44

      (laughs)

   10. HSHarry Stebbings0:44

       ... I'm ready for this. But I hate shows which actually start conventionally, and so I wanna start with a bit of

2. 0:49 – 5:20

   Tim Urban’s Early Life

   1. HSHarry Stebbings0:49

      a weird one. But think back to when you were a child. What did you want to be when you grew up?

   2. TUTim Urban0:54

      Well, I think it depends on the age. I think, like, f- five, you know, six, I would've, it would've been something to do with space or dinosaurs. Those were my two obsessions then.

   3. HSHarry Stebbings1:08

      (laughs)

   4. TUTim Urban1:08

      Um, so probably just, you know, oh, yeah, astronaut, something like that. Then, um, I think, you know, by the time I was 13, 14, 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.

   5. HSHarry Stebbings1:36

      (laughs)

   6. TUTim Urban1:37

      Um, (laughs) uh, it's like, this is, this is not, this is not-

   7. HSHarry Stebbings1:41

      The pressure was too much-

   8. TUTim Urban1:42

      ... what I like. It just-

   9. HSHarry Stebbings1:42

      ... too much for you.

   10. TUTim Urban1:42

       No, just campaigning, trying to get people's votes, like, and then for what? So that you can have, like, what's actually just kind of like a glorified bureaucratic, like, you know, administrative role? Uh, I was like, "No. I don't want that." Um, and, uh, and then from then on it was basically like I- I probably, uh, I always wanted to be in something creative, music or writing.

   11. HSHarry Stebbings2:03

       Okay.

   12. TUTim Urban2:04

       Um, yeah.

   13. HSHarry Stebbings2:04

       So, we have these different stages of your 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 ambassador, 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?

   14. TUTim Urban2:26

       I'm probably running fr- okay, I, 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, s- I loved camp. It's not like I hated school or camp. They were fine, but, like, e- then you'd go to, 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 fr- you know, just having as much freedom as possible, to the point where now if I have anything on my schedule, you know, for 5:00 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, 'cause I just want, like, total freedom.

   15. HSHarry Stebbings3:31

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

   16. TUTim Urban3:41

       I mean, I think that the- that's- that's, you know, it, I think part of what is, you know, the- the part of me that hates that is not necessarily, like, I think there's something to freedom and having actual ch- 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 that's kind of a grownup, and then there's the rat- 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, h- you know, designing everything to not have to have the monkey be upset by saying, "I don't wanna 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 it's be- better than sitting around doing nothing. So, I think you can go too far and, uh, then if you ha- don't have any of those external structured things, then you end up in a, um, you could 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 feel like I'm now trying to regain that structure, but kind of on my own terms. But kind- trying to, like, find that medium where I'm not, like, being told by someone else or someone else's schedule what to do every minute, but I'm, I am doing stuff that makes sense every hour and I'm not just doing nothing. So, I feel like a- so- I'm trying to now capt- recapture some of that actual structure.

   17. HSHarry Stebbings5:07

       In terms of recapturing that structure, the realization of the freedom of the, what you have today with Wait But Why came really with, you know, a couple of hit pieces. You know, one of them being the Fermi paradox. Massive hit at the

3. 5:20 – 11:27

   Making Money from "Wait But Why"

   1. HSHarry Stebbings5:20

      time. W- when did Wait But Why really come to be as a very viable pathway for you to pursue as a very meaningful career?

   2. TUTim Urban5:29

      So, I, since I was, you know, I was at like 17, 16, 17, I was like, "I need to do something creative in the arts," you know, music or w- writing. And I moved to LA after college to write music and that was my first thing, and then I was blogging on the side. But then I started this business with my friend Andrew Finn, and that was, um, that was fun. We were running, running this tutoring test prep company together and it was great. We were working with a friend, you know, but I was, I had this voice that was like, "Ah, this isn't the thing that you said you were gonna do. You're, you're, you know, you're macro-procrastinating." And, um, and so actually I talked, I remember it was actually, like, summer of 2012 w-... I was walking down the s- Manhattan Beach boardwalk with Andrew, which is where he lived, and I was like, "I'm going crazy. I need to do one thing." I'm doing, writing a musical right now on the side. I'm doing a blog on the side. I'm r- running this business with part of my time with you, and I need to, like, go. And so, like, why don't we do something, you know, where you, you know... We've done this before where he went and worked on a project while I held down the business, and now he was like, "Okay, why don't..." You know, he's gonna keep growing this and I'm gonna go and take one of these creative pursuits, and it'll be part of the kind of joint business world that we, we're in. And I went in, so I was like, "Okay, musical is fun but it's not a great business." Um, but writing can turn into, like, m- you know, a media empire. Who knows? Like, you know, maybe we hire a bunch of writers, maybe, you know, there would be... Maybe it, it becomes a platform that can have influence and... E- e- either way, it could be, like, an actual... It's not just interesting to me as a creative, it can be interesting to, to you as well, um, as a, as a businessperson. So we were like, "Okay, that's a good choice." And the, the key was, I'm going full time, s- you know, 60 hours a week on one project, and that was Wait But Why. Um, and that was kinda the beginning. Then it took a year before I launched 'cause of procrastination, and, you know, it was, uh, uh, it was this thing I was gonna do but I had to... How do I... I have to get a domain somehow, I have to figure out how to, like, get social media buttons on a blog page. I have to write the things. What's the... Is there like a... Is everything, like... Is every post like seven things I think about this, that, that? Is it like that or i- is it longer things? Um, is it funny or is it... I don't know. I didn't know anything. Are, are we hiring other people? Is it just me? So for the sake of money, we were gonna start with it being just me, um, and it was just kinda like, uh... Finally, you know, uh, got, got it together in, uh, summer of 2013, got it started.

   3. HSHarry Stebbings7:44

      When did you start making money from it?

   4. TUTim Urban7:48

      Pretty soon. You know, the, the, the... It was about 10 posts in that the, that one post really blew up and, you know, m- 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 of kinda, like, up- made this ugly... It's like, I feel like I, 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, Phillip 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, 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, like, ways to kind of cobble together revenue once you have a decent following.

   5. HSHarry Stebbings8:47

      Can I... I, I, I've actually never spoken about this but I've never had the chance to with someone, um, (laughs) i- 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. (laughs)

   6. TUTim Urban9:04

      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 'cause 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 s- you know, chunk of revenue. Um, that's, you know... So, um, but, you know, but part, part of the, uh, the, the, um-

   7. HSHarry Stebbings9:49

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

   8. TUTim Urban9:52

      No, I don't actually, because, because I don't, um, I don't say anything that's not... It, it's basically just me taking what I write in my blog and translating it to a different medium, to speaking medium. I'm never gonna... I'm not gonna get up there and, like, speak, um... I'm not gonna do what the conference wants me to do. If, if they, you know, I mean, I'm not gonna... If they say, you know, "We want you to promote this con-" I'm not gonna do anything like that. I'm gonna 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 a, that a conference wants me to speak about, I'll just go and do the talk version in their slides and... Uh, I mean, I did that with the TED Talk with my procrastination post. So tha- 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'd written this AI post, it actually doesn't make much money 'cause 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's a... It comes later in form of speaking.

   9. HSHarry Stebbings10:46

      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'm in.

   10. TUTim Urban10:56

       Well, th- th- that's why we haven't actually... I, I've, 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 Alisha, 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 'cause I just wanna be able to, like, indulge my curiosity full time and, and, and work on stuff.

4. 11:27 – 17:03

   Tim Urban Considers Being a Venture Capitalist

   1. TUTim Urban11:27

      Um, yeah.

   2. HSHarry Stebbings11:28

      Why have you never done a venture? I'm totally going off schedule but I'm loving this.

   3. TUTim Urban11:32

      Yeah, I know. Cool.

   4. HSHarry Stebbings11:32

      Why have you never done a venture fund? It's perfectly placed. I would put a place... And I, like, I keep going back as to why you should do it. Why have you not done it?

   5. TUTim Urban11:42

      I, I, I think... It's not that I'm not open to some of these things, it's just that it's like that's gonna take a lot of time, you know, and it's gonna take a lot of brain space. Um, and, and I just, uh... It feels like I got out of the business world so that I could just spend my time thinking about making cool, like, pieces of creativity. You know, art, whatever you wanna call a blog post or a book. Um, and so I just, um...... I kinda wanna just keep doing that until I'm bored. Maybe at some point, I'm like, I don't... You know, I am starting a podcast later, uh, you know, li- this year probably, and it's like, that will be a different thing, but it's still the same- it's still, you know, i- i- it's, it's, it's about, like, expressing things that I'm learning or going on in my brain or talking to interesting people, so that, to me, still fits within the realm of, like, what I got into this for, and I'm just trying to keep it... I don't wanna, like, you know, in five years or 10 years turn around and say, "Oh, you know, I'm, this business got so big but I, like, actually lost what I cared about for it." I'm like, well, you know. So I think there are... I think, like, look, there's, there's a lot of, um, uh, you know, someone like Sam Harris, right? He has this big loyal audience. He's doing what he does for, you know, pretty pure purposes. He cares about, you know, ideas, and he wants to... But he, you know, one thing that f- one revenue-making idea that came- that fit perfectly with what he really does is his meditation app, and he makes a lot of money off that, you know? So it's like, if there's, if there comes around an idea, and we have a few kicking around, that's like, "This fits with the, what, what we're doing. It's, it's part of the, the thing I wanna be doing and it also can make a lot of money," then great. We should do that. But, like, th- uh, part of what's nice about having had that business before is that, um, there, you know, we, we have some, um, uh, other revenue sources that allows Wait But Why to kinda have pure motives, um, and not have to do anything that I- I don't think it fits with the brand.

   6. HSHarry Stebbings13:30

      I, I just think of venture investing, like, you have to have a brand that the best founders want to take. You have that with Wait But Why. You have to then be able to pick founders and companies in a better or more accurate way than others. You are able to do so through your incredible research and investigation, and then you have to be able to help founders in a variety of different ways. Your chocolate box of options, you have that most definitely in your platform distribution reach. Across the venture landscape, you have those very synchronously with your business, plus with a $10 million venture fund, which is quite small in venture funds, it really is, like, an hour or two a week, and actually, you could raise it in an afternoon, and that-

   7. TUTim Urban14:13

      Is it an hour or two a week to, uh... You know, the, I do a lot of research, but it's not that often from, you know, startups. It's- it's- it's often in, you know, established companies or in-

   8. HSHarry Stebbings14:22

      Yeah, it-

   9. TUTim Urban14:23

      ... history, or-

   10. HSHarry Stebbings14:24

       Dude, I think you're ri-... I think it would- w- we're really being, like, off-script here, but like, yeah, like your Benchmark Sequoias of the world and the best funds will bring you in for your distribution reach, intellect, thought, uh, so you'd get incredibly high-quality flow. Um, your selection ability would be very high given the deep dives that you do, um, and so I honestly think, yeah, you could constrain it, and then with a platform like AngelList, the back office and admin is minimal, minimal. And so maybe it's not an hour or two, maybe it's half a day, max four hours, but it's pretty light for a potential 8 to 10 million windfall on a 4X or 5X fund, and actually-

   11. TUTim Urban15:03

       Yeah.

   12. HSHarry Stebbings15:03

       ... pretty good. Like, I would make-

   13. TUTim Urban15:05

       Well, may- may- may- maybe, maybe, maybe we should talk more and, uh-

   14. HSHarry Stebbings15:07

       (laughs)

   15. TUTim Urban15:07

       ... you can continue talking me into it 'cause, um-

   16. HSHarry Stebbings15:11

       Sure.

   17. TUTim Urban15:11

       ... every time I hear anything like that I'm always like, icky, icky, like other whole thing that I have to do, like... This is kind of what I was saying with stuff on my schedule. I have such a resistance to- I know what that would turn into, which is like, it's Thursday night, I'm like, "Ah, so much, like, writing I need to do tomorrow," and then I look, and I'm like, "Oh, second half of the day is blocked off for this VC," and then I'm like, "Oh, no, no, no, no, go away." And that's the fear. That's always the fear, and may- maybe that's too- maybe I, I go too far in that direction, but just, like, anything that's gonna start, like, having stuff on the schedule, it feel very claustrophobic suddenly, and it feels like, um, it's, like, invading my space to just, like, think and learn and write, um, but, you know, maybe again, as I said, I'm also trying to run two m- trying to kind of get out of that mindset a little bit and, like, be kind of more okay with, like, having an efficient block for writing every day and I don't have to have the whole day open. Um, you know, that's a pretty big constraint. If you have to have the whole day open, you can't take on other things.

   18. HSHarry Stebbings16:01

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

   19. TUTim Urban16:05

       Uh, 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, uh, 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, y- 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 claustropho-... I think yes. I think if I were in a relationship where she was like, "Okay, it's like, you know, 5:00 PM. Like, let's... Work's over for the day. Let's go do something," or like, you know, "It's- it's- it's like Saturday. We don't go on the computers on Saturday," I might think I might wanna, like, yes, I might wanna run away. I- I don't- uh, that's not my situation, so... (laughs) Um...

   20. HSHarry Stebbings16:54

       Oh, by the way, I loved your piece on picking the right partner, which goes to my- (laughs) which goes to actually what I did wanna talk about before I went di- drastically off-piece there, but it's actually

5. 17:03 – 29:55

   Tim Urban’s Selection & Research Process

   1. HSHarry Stebbings17:03

      on topic selection because you have this incredible variety of topics that you focus on, and the first thing I wanted to break down in the process of your work is topic selection. One of your friends who I spoke to described you as the most genuinely curious person they've ever met. My question from that was how do you determine between interests to pursue v- and write about versus those that you won't cover and won't write about and examine deeper?

   2. TUTim Urban17:32

      Um, I, I think it- it- it really is, um... It- it is about kind of my... It's, it's, like, curiosity and kind of almost, I wanna say just kind of excitement. Like, um, you know, if I think about, like, there's certain, I don't know, topics that I would think about or, um, where I'm like, I- I'm, like, excited to do it, and it's not just, you know- you know, curiosity is one thing. Like, you know, when I, um, when I, when I first read about Neuralink and I started to understand what they were doing, I was like s- I was, like, jumping out of my seat to, like, write about it 'cause it seemed so cool, and I just wanted to, like... I- I suddenly, it was like- it seemed like a game to try to, like, take everything I was learning and, like, what's the story here? How- what's really g- like, like, how- how would I, if I had a bunch of friends sitting around, like, how would I explain this to them and, like, um...... this, like, incredible story. Like, how do I tell it? Okay, but then there's also sometimes just like, I don't know, like, yeah, like procrastination or, uh, life partner, stuff like that. That's not, like, necessarily curiosity as much as it is, um, uh, I know I have a bunch of swirling thoughts in my head. A lot of times those to- those, those posts emerge from conversations with friends, like, we're always just talking about this. We're always talking about, like, I'm always, you know, I'm always thinking about my own, you know, work habits and procrastination and what's going on there in the head. And I have this idea that there's characters in the head. Or I'm always talking about relationships with my friends, and we, we're saying that these are the three things that actually matter, you know, or whatever they are. Um, and, uh, and so then it becomes like I'm- what, the thing that would excite me there is like, I'm gonna now take that s- kind of scattered thoughts and I'm gonna make, like, an official framework, which is just the kind of thing I would just do when I'm procrastinating, you know? Or, like, uh, I'd wanna be, um, I would think, okay, how many gen- you know, it, it's been six million years since we diverged from chimps. Okay, like, how many generations is that? Like, how many great-great-great grandfathers do you have to go back before you get to, like, a, a, like, a full, full monkey situation? And like, that's so interesting to me, so then I wanna like, okay, I'm gonna make a chart and like how would ... I would just do that on my own just to like be like, okay, so that's, you know, I don't know, six million years and just say there's, you know, 30 years, um, uh, so that's 200, you know, per generation, that's 200,000 generations. Okay, so if there's like 100 ba-da-da, you know, that's 2,000 in a row and I'm trying to picture, wow, that's how many, like, great-great-grands you have to go back to get to monkeys. So I would just do this in my own head. So that's a perfect topic. W- there's a lot of topics I'm not curious about or that I th- I think, I think about writing about and I'm like, ugh, ah, sounds icky. Like, there's a lot of stuff about like, I don't know, philosophy, people talk about, like, the self and, like, consciousness. I'm kinda just like, ugh. Just like, I don't know, it's abstract and crypto. People wanted me to write about crypto and I was kinda just like, ugh. I, I don't, I don't, I don't ... This is, it's j- it's like this hasn't proven yet to be a huge part of the future and if not, then it just seems so boring to write about. So, there's plenty I'm not curious about. (laughs) So it's just what kinda grabs me or it seems like a delicious topic, potentially.

   3. HSHarry Stebbings20:27

      When you find something that is a delicious topic, but you're not versed enough to write the incredible works that you do about it, but you've decided you want to do the work, what does that learning process look like from decision to write about it to starting to write about it? How do you do your research and learning?

   4. TUTim Urban20:48

      Yeah, so, um, this part is a fun process. I mean, it's, 'cause if, if it's the right topic, it's a fun process because it's just like, yeah, it's just fully indulging curiosity and it's, and it's, it's kind of exhilarating going from, I always use the, you know, the scale of like, a 10, a 10 out of 10 knowledge is like the world's leading expert and a one out of 10 is you haven't even, like, heard of the topic. Um, and so, you know, for most topics, I don't know, I'm a two or three or four, something around there where I'm like, you know, I know something about, I know a decent amount about this. But, and, and I could talk about it with smart people and, you know, not say anything stupid and I have a sense of how it works. But as soon as I like, but, but I don't actually really know what's going on here. You know, there's mil- endless topics like this. Um, and, uh, so my goal is never to get to like the eight or nine or 10. You know, that, that would take years. You really, you know, that takes, you know, years and you have to understand all the different schools of thought and how they interact with each other and you have to deeply understand the technical, you know, nitty-gritty of it, uh, and, um, and you know, have, have debated it and argued a b- and written, you know, written dir- dissertation, you know, toiled through something like that and then had to defend it. No interest. No. There's too many, there's too many to, I don't think that's, I think it doesn't, that, that's a limit on how interesting th- you know, there's a diminishing return on, like, excitement as, as you, as you keep putting those years in. So for me, it's like, I wanna get from like a two or three, you know, to a six. Five or six, something like that where it's like, oh, okay, I understand this way more deeply now and actually like, I have a really intuitive sense of like what's going on. So, I don't know, like, um, yeah, like, I'm, I'm currently, you know, researching something on, um, like the origin of life, right? And like, uh, and before I was like, okay, there's like some kind of, um, you know, first cell. There's some kind of like par- or- or early particle that has like the property of self-replicating and f- it goes from there. But that's not actually knowing very much, and now I'm like, you know ... So, so anyway, to answer your question, here's what I would do. Here's what I'd do at that point, is I just, first I'm like, what are the ... H- honestly, sometimes I just start Wikipedia. Just read the Wikipedia article, 'cause Wikipedia's often a good overview of the schools of thought, of the controvers- you know, what's controversial, what's not. It does a decent explainer s- and then, and they range. Some Wikipedia articles are amazing and they're really good and some are actually not good. They're way too technical and long or they're just not updated enough and you, you can see they're kinda short. But I'll give something like that a try. Just, I'm just starting to just, I wanna, what, I wanna understand the shape of the topic that I need to, to even know where the holes are in my knowledge. And so then, I, I'll, um, I'll often, you know, um, I'll read some articles, right? I'll watch y- YouTube videos are great. Just again, just to start, like, it's like, I, I'll watch a YouTube video on one part of the topic and it's like, okay, here's like a hi- it paints one of the facets of this shape. And then a different YouTube ... You know, and so I do this for a while, just to understand, like, the general thing. Then I'll start going deeper usually, like, I'll pick up a bunch of books. So like, for origin of life, um, I'll read a couple Richard Dawkins books and I'll read, there's a book called, um, The Early, uh, or Life, uh, what's it called? It's by Knu, uh, Life on an Early Planet, maybe. Um, and, uh, you know, that, c- and, and partially as e- as you read, you see the sources that you, you see people get brought up again and again, you're kind of, you're, I need to go read that person's book. Uh, maybe I'll actually read The Origin of Species, or, you know, skim through it or, you know. Uh, you can use ChatGPT to summarize some of these books. So, but the big point here is I'm just, I'm not worrying too much about each source. I'm just, um-... like, in- in- in bringing information in. And then I'll usually try to do it in Kindle app so I can on my computer or iPad so I can highlight, 'cause then that's r- nice to go back and just look through the highlights. Um-

   5. HSHarry Stebbings24:29

      Okay, so j- just so I get it right on the note-taking side, so you use Kindle app there, and for others, for YouTube videos, for articles, do you just do Word docs, Google Docs? I'm just trying to get a framework for how you do-

   6. TUTim Urban24:40

      Yeah, I'll have like a text edit doc that's just very basic, where I'm just starting to like, um, if there's something, eh, I'm like, "Ooh, okay, I just learned about like metabolism versus replication as the two theories, okay, and this YouTube video actually like explained it pretty well," so I just wanna be able to come back here and reference this, you know, and just make sure I... So I'll like, um, save the, you know, you can, you can get the hyperlink that's at- at a certain time, so I'll just kinda like write, um, you know, "Metabolism versus blah blah blah," you know, YouTube, and then I'll highlight YouTube, I'll- I'll hyperlink the YouTube to that place, so I can just go. And I just have a lot of that. Uh, I'll- I'll- I'm not gonna bring out full paragraphs, 'cause I have highlights for that but I'll say like, "Dawkins, w- 254," and I know that that's like the highlight at 254. And- and as this happens, what happens, you know, you, it's- it's like early on it feels like daunting and you f- you can feel the fog, you know, you can see it's like, "This, I don't really get what they're talking about," you know, "What is metabolism exactly?" It's like the- the- the- is it- is it- is it- is it- is it energy, you know, is it- is it when you- when you process energy or is it when you construct something or deconstruct something or is that what enzymes do and what's the difference between like, you know, um, a- as an enzyme and a catalyst, are they synonyms or they d-" You know, you can feel foggy, you feel like you just, y- and- and- and you, I know if I wrote at that point, someone who really knows the topic would wince at like the terminology that's not quite right and the way I'm talking about it is like, shows some ignorance. So, th- I'm definitely not ready to write then. But what happens is as you read more and more, you start to just get it better, like it starts to make sense, and what's really gratifying is then I'll often go back and read the same source that I did earlier. I'll g- I'll read the really good sources again now when I'm closer to the writing time, and it's so satisfying reading them again and being like, "Oh, this makes so much more sense now." And, eh, that's this really fun process, or I'll go rewatch a YouTube video that was a little confusing to make sure, 'cause that's like tests, like I should now be able to understand this YouTube video perfectly. Is there any fog still?

   7. HSHarry Stebbings26:32

      Do you ever- do you ever worry that a cop- that a topic is too complex or intellectually challenging, intense, for a broad audience? When you talk about metabolism there versus whatever it was (laughs) 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?

   8. TUTim Urban27:01

      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, you know, I'll read five or six books, maybe- maybe more, I'll skim through chapters of other books and bunch of papers and YouTube video, 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 gonna use that metaphor and credit the person or I- I- I have- I have m- my different version of- of- of- I have- it- it- it stoked a metaphor in my- that, you know, that made me realize I- I have a better metaphor for this that I'm gonna use, but I will note all these like dopamine hit moments where I'm like, "Oh, that, like, that clicked," right, that's important. And at the end, basically my job is to... There is something, eh, the origin of life is o- officially interesting, right, and now the question is how deep do you go? So if you d- 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 today. Okay, that's not like deep enough, like people kn- know I didn't really teach most people anything new there and I'm not, it's not interesting 'cause it's so broad. So then you can go deeper, right, and it gets mor- to me it gets more and more interesting and I know this because I use myself as the, as the focus groups 'cause I know what I just got dopamine hits from and I was like, "Oh, that is so cool," right, okay, perfect, 'cause my readers are gonna think that's so cool too. And then other things I'm like in the, you know, I'm deep in this chapter and I'm like, "This is so boring." It's like so specific now, you know, I'm getting to like the really, really de- so e- I- I'm using the origin of life, but AI is like this. You can go, you know, I can explain ChatGPT, uh, again if you explain it the- the really broad way you'd say something like, "This is, you know, um, a, uh, a large language model which allows you to ask questions and it uses the whole internet, you know, uh, as data to answer them." Okay, not saying anything new there. I can go deeper and try to explain, you know, how large language models work and how like, um, it's- it's, you know, this, it's- it's this complex process of choosing the next word, you know, using m- brute force of computation, whatever, and okay maybe that's more interesting. You can go really deep and start to explain how transformers actually work and all these j- all this jargon and, um, and now you get to really boring again, right? And so any topic you mention, there is, you- you can- you- you can keep going, keep going, keep going until it gets really technical and boring and so my job is to basically have good taste for what is actually interesting to people like me. You know, reasonably smart, educated people who are very curious but don't know that much about this topic but they'd like to know more. What is that, what's that sweet spot of, you know, what are the things and- and the ways of explaining it that are gonna make them, you know, have, if I had dopamine hit every hour while researching,

6. 29:55 – 36:26

   Analyzing Content Performance

   1. TUTim Urban29:55

      I want them to have one every minute while reading my post.

   2. HSHarry Stebbings29:57

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

   3. TUTim Urban30:06

      Yeah, 'cause some topics are, you know, I- it's like I thought they were... Ah, 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, eh, I'm trying to think of th- uh, 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 sub-topics. 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 happen. And then I realized it's like it's so... I mean, I'm still researching this, but I was like, "This is so complicated." It's actually not. I thought it was 'cause like the sun is just angled, you know, th- 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." I'm like, "Ugh." Uh, I'm, I, if I feel bored and I feel like I'm like, that I'm back in like a boring high school class, out. I'm not gonna write that. I'm not gonna write about it.

   4. HSHarry Stebbings31:21

      Have you... I, I have this sometimes with shows. Have you ever had it where you think it's interesting, you do it, but post-release it doesn't resonate with audience in the same way that your interest resonated with it?

   5. TUTim Urban31:34

      Yeah, definitely. Sometimes it's hard to know what specifically, you know, within the post resonated. I think if I had more granular information on, like, "This paragraph bored 90% of people," I'd be like, "Oh, shit, it didn't... That's surprising to me. I thought it was..." So I don't really know. You know, it's like I know how well the post in general did. Um, I think what would surprise me is which parts were most interesting. Um, but-

   6. HSHarry Stebbings31:55

      Which post has done the worst that you thought would do well?

   7. TUTim Urban31:58

      Um... I mean, early on, in the first, you know, year of Wait But Why, my goal was, like, to go viral most of the posts, right? Then I started just doing stuff I was, you know, just purely that, that grabbed me and that I thought would be fun to write about. But early on, it was like, you know, "Let's get some readers here." And so the first, like, 10 posts, it was like maybe this one, v- mega viral. I'm like, "No." This one, mega viral. Like, "Oh, this one's hilarious." I'm like, "Nah, it wasn't hilarious." And I'm like, "This one's gonna, like, be super controversial." I'm like, "No one cared." So, you know, there were definitely posts early on, like, that I was, um, you know, I thought this one... Like, I, I wrote a post on something called like the Apple game that my friends and I love, and it's like you rate everyone by, um, their, uh... Like, so, is, Apple has skin, flesh, and then a core. So every person is kinda like that, where the skin is, like, the vibe they give off when you first meet them, and then the flesh is, like, who you, their friends know they really are, and the core is who they really are deep, deep, deep down. You know, that maybe only their spouse or their best friends know. Maybe no one besides them know. And so for each one of these, you give a good or a bad. So someone can be, like, a good/bad/good. It means they have like a... They come off really, like, well, they're friendly, but then you get to know them better and they're a huge asshole actually, and they, like, will talk shit about those people that think they're friendly. And then, but deep down in their soul, they're, like, quite good. So it's like they're a good/bad/good. So anyway, this game is so fun with my friends, and I was like, "This is gonna b- be, like, an internet sensation. I wanna publish it. It's gonna go everywhere. It's gonna be, like, the only thing people are talking about." No. Uh, some people have told me, uh, that it is their favorite post, a, a few here and there, but, like, it's, it just, it didn't catch. Meanwhile, then a couple weeks later, I write a post called Why Generation Y Yuppies are Unhappy, which was the word, that was be- before we're called the Millennials. It was, like, right before Millennials became the topic, the, the, the term. But it was basically why Millennials are unhappy, and I, and I, again, it was the same exact feeling. I was like, "This is gonna, like, this is gonna catch fire when I post it. This is, like, everyone's gonna, you know, this is gonna be..." And it did, and it totally did. Like, that one got, you know, it was, it, uh, it, it, it got... 14 million people read that in a week. It was, like, a huge... So I thought that was gonna happen seven times before it actually happened. Um, so some, if, uh, I think those are the hardest ones, when you're, like, trying to go viral and write something that's gonna, like... That's, like, very hard to predict, and you kinda get, kinda get some luck. Um, as far-

   8. HSHarry Stebbings34:06

      But-

   9. TUTim Urban34:06

      ... as like a topic that I'm like, "This, I think this is interesting," I, I think I've gotten a... I think if I find it really interesting, there's at least a certain critical mass of my own readers that will usually agree with that.

   10. HSHarry Stebbings34:16

       I constantly struggle with the element of something does well and so I do more of it versus doing it for myself and my own interest. I almost don't want to be swayed by the data, and I just want to focus on high-quality output. I find sometimes the best shows performing-wise are 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?

   11. TUTim Urban34:52

       I think, um, it's not that I don't chase viral anymore. Um, but I'll do it in, in... It has to also go along. So like, 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 c- crypto explainer. But I just didn't want to (laughs) . Um, and I think early on, if I knew that I'd had almost a guaranteed, you know, mil- you know, million people in the first few days viral post, um, I would've done it, right? It was just then it was like, "Take that. Oh, amazing. Uh, people are gonna..." But I think, um, you know, I- 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 w- my, my motive, um, ex- 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, if I think, like, um, that my actual readers will, like, love this, um, then that's very exciting versus like, "This is gonna, like, this is gonna go viral, and a ton of new people are gonna, like, learn about..." I'm like, that doesn't, that doesn't do it as much for me.

   12. HSHarry Stebbings36:25

       If we think about kind of making

7. 36:26 – 41:54

   Tim Urban’s Writing Process

   1. HSHarry Stebbings36:26

      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?

   2. TUTim Urban36:46

      Yeah. Uh, 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, or I, 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 s- 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 write. Um, and that, you know, I don't know, I'll write ... I can, I can usually pound out, I can have some pa- 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 gonna be up Friday," then I can, like, probably write two or three thousand words a day, Thursday and Friday, and get it up, you know. Um, 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 s- 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 calls it, like, dead on the inside mode that, like, she was in during law school finals when it's just, like, you're in a certain zone where it's like, someone like, you know, you haven't eaten anything and, and you just, like, fi- you just kind of absentmindedly grab, like, a granola bar and you're eating it while still typing and, like, there's no inclination to procrastinate or do anything fun 'cause you're just like, f- you're just on a mission. And you're in probably usually, for me, because I'm, I'm panicked, 'cause I'm like, "I need to finish this thing," and like, it's like a ... So that's a n- not a pleasant zone to be in, but that's when a lot of Waipahuai posts have been written, in that zone. A book, you can't b- be in that zone for four months straight, or however long it takes, six months to actually type the words. So, f- for this book I'm working on now, I'm on a pretty strict regimen of I have to do 800 words, new words, a weekday. And if I get behind one day, 'cause I'm doing extra research, then I have to catch up later that week. Um, and, uh, so that, that, that compiles, you know?

   3. HSHarry Stebbings38:53

      Do you guys ever have writer's block?

   4. TUTim Urban38:56

      Yeah. I mean, I call it, like, a snag. Um, I think, you know, I think fiction writers must really have, like, a certain kind of writer's block when they just don't feel like ... They'll, they feel very, like, untalented, you know? And it's like, you feel like, I'm like, I, you know, you just, "I don't know how I used to do this, I don't know how anyone does this, I'm not good at this." So I feel that sometimes, for sure. But, but mine's a version of it, like, maybe a more non-fiction version where I'll just hit a s- I'll hit a snag where I don't know, um, I don't like what's b- coming out. Like, I'm like, "This is not, I, I, I don't like the structure here," or something. Or, "I don't know how to do this next, the structure of this next section." Or, "I don't really understand the topic in this next part well enough and I have to go read, but I don't even know where to start and I just, I'll, y- you'll wanna do anything other than this pro-" Just push, it's just hugely procrastinating, um, uh, you know, inclination in that moment. So, I, yeah. I ca- I, I have huge moments of despair. And in those moments, and this is, I think, a lot of just anyone doing creative projects. You just feel like, you just feel very, like, untalented at what you're doing. You feel like, you're like, "I don't know why anyone thinks I'm good at this. Like, I don't know how to do this." And that's, like, a very common feeling. And I, I definitely, definitely get there. Um, and you just have to have faith that things-

   5. HSHarry Stebbings40:09

      What do you, what do you, what do you do when you hit the snag?

   6. TUTim Urban40:12

      Well, I think if I don't have the right external pressure on me, I procrastinate, eh, by, I will, it'll, it'll, it'll just destroy my productivity for weeks on end, um, while I just each day avoid getting into it, and then I get into it, and I'll research instead of trying to write because I, and then I'll try to re-outline the whole thing, and then I'll think that's a good thing, and the next day I wake up and I hate the new outline, and it's just, it's, it's unpleasant. Um, uh, but yeah.

   7. HSHarry Stebbings40:43

      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, what, take me to-

   8. TUTim Urban40:52

      The, honestly, that can be-

   9. HSHarry Stebbings40:54

      ... take me to Andrew Grynswert, where does the magic happen?

   10. TUTim Urban40:55

       For me, I like the computer, whether it's on my, uh, monitor, external monitor, which is, uh, you know, the, the 32-inch monitor in my apartment, or it's on my laptop, uh, fine. Uh, the monitor's a little nicer, and like a nice chair, it's like, great. But laptop is fine. I can h- my workflow, I'm good with the keyboard shortcuts, I can al- I can, 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 I, if I can't r- easily just while writ- you know, r- 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, h- it's, I don't know. But 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 Mac OS, like, could do it better. But I, I don't like ... And then phone, like disaster. I could never, like, could 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.

   11. HSHarry Stebbings41:53

       H- so I,

8. 41:54 – 47:15

   How to Grow Your Social Media Following

   1. HSHarry Stebbings41:54

      I say two things on content and winning at content. One, consistency is everything. Your reader has to know, or your consumer has to know when the next thing is coming. It needs to be a habit in their consumption. Do you agree with the importance of consistency?

   2. TUTim Urban42:09

      Uh, I think it's very important when you're getting started, um, because people wanna know what's happening, they're not gonna just check and check and check your site, right? And you don't have a huge email list yet or anything. So, um, it's critical, I think, early on, to be like, I, I started with a new post every Monday and Thursday, and then I changed it to every Tuesday. And for the first year, while I built up my readership, sometimes it was Wednesday, even Thursday, but it was a new post every week. Um, and that was, I think, very important for that first year. And then, at that point, um, I had a big email list. And a big email list s- d- makes it less important to have consistency. I th- I still think it's better than not. I think that, uh, you know, and it's not ideal, the way I do things, but I'm very inconsistent now. I'll disappear for a while and then I'll come out with something big, and then I'll disappear for a while.... um, but I, but the, the big email list and social, you know, s- social platforms, they are, they make it less important because I can, I can ping the email list as, when it is done. So it's like then they all come, who, to read it then. As opposed to if the only way people are seeing your stuff is if they think to come to your site to check if there's something new, you've gotta be consistent if that's, if that's the main thing going on.

   3. HSHarry Stebbings43:15

      A- agreed. The next thing I say is actually volume is everything today. It is purely a game of output. You need Instagram Shorts, you need, sorry, you need YouTube Shorts, you need Instagram Reels, you need TikToks, you need podcast episodes, you need blog posts, you need Twitter threads. You need to be everywhere because attention is currency, and it is a game of volume and quantity today more than anything actually. I think you'll disagree, but I'm intrigued to hear your thoughts.

   4. TUTim Urban43:43

      Well, I mean, I, I, I think, um, the way I view it is if I make something, you know, a blog post, okay, where can this just, without any work, also create, uh, um, stuff on other platforms? So if I did drawings, okay, which, which of those drawings are good standalone Instagram posts, um, or, or tweets? Um, what, which ideas as I did it from the research or from my, from, you know, you know, from the, the post itself like are good tweets or whatever? Um, i- i- if and when I have a video podcast, okay, let's make clips for Instagram Reels and for TikTok and for YouTube Shorts, you know? Um, sh- so I think like, yeah, it's, it's, it's a very good bang for your buck to basically photocopy parts of what you've already done onto these other platforms. I don't think that, uh, that, that a new creator needs to be worrying about, "Oh, I only doing like writing and drawing right now, I need to also be doing TikToks. We need to start doing video to make sure we have stuff on TikTok." I, I don't think... I think they should focus on doing an A+++ at one thing, uh, uh, and then that one thing, spreading it on as many social places that, you know, makes sense for that particular thing and just focusing on that. That's what I think. Um, I, I, I think someone who's crushing it on TikTok doesn't also need to have, um, a, a big Twitter. I don't think they need that, you know? Like, it's again, I, I think the one, the one argument to have something going on in every platform is platforms change. Uh, and you don't wanna have... It's like diversifying your attention portfolio. You know, you wanna have... Um, you don't wanna have, you wanna de-risk it and not say, "Oh, well, you know, if everything's in Facebook and Facebook becomes unpopular, you just, you know, l- lost everything." So you wanna diversify.

   5. HSHarry Stebbings45:30

      I think that, that and ease of transportability across platform. Like, if it is super easy to move to TikTok-

   6. TUTim Urban45:35

      If it's super easy, why not? Right? It's just an-

   7. HSHarry Stebbings45:37

      ... um-

   8. TUTim Urban45:37

      ... automatic, you know, easy-

   9. HSHarry Stebbings45:38

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

   10. TUTim Urban45:52

       So if it's a blog post, honestly, we're not like... W- we could be doing better at this. Like, I think, you know, right now if it's a blog post, I'll pu- 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... The, th- this is a bunch of in- good Instagram posts that can come out of this post, here's a bunch of tweets, and, you know, Alisha might pos- publish them over the next couple weeks. Uh, for the book, um, that I published, like we, we pulled out a bunch of potent- a bunch of social content that can be, you know, done on, for the book. Um, but, but bi- uh, 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 patr- we usually let patrons know the night before, right, right when it comes out, 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 s- some we c- ex- extract some social media posts from this post for the next couple 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. And, you know, so we'll do that and promote it on the normal places. But like I do a very basic kind of, I don't know, like 2015, you know, technology

9. 47:15 – 50:31

   How to Build Your Brand

   1. TUTim Urban47:15

      job at this. I'm sure some people are way more sophisticated than I am.

   2. HSHarry Stebbings47:18

      Can, can I ask you, do you enjoy being a brand yourself?

   3. TUTim Urban47:24

      Um, I'm not sure I'm a brand. Uh, but, um, I, I, I, like as far as, um, like having people know me for like the stuff I'm doing, um, I, is totally great and gratifying because, specifically because the stuff I'm doing feels very true to me. It feels high quality and it feels like the, the re- that's like the, the real thing I should be doing. I think if I were, you know, um, I think, I think that I've, and I've experienced this, when I'm, I'm, you know, whether you're known publicly or just amongst, you know, people in the industry or whatever for something that feels like this is what I'm doing now but I really wanna do this and I should be doing this and I'm just doing this now because, that's a bad feeling I think. I think, um, it feels, you know, you're always like a little bit... s- it's like a little soul-crushing doing your stuff. And, um, and, and so I think, uh, that's why I think it's really important if you are gonna especially do like kind of create- creative stuff, do, do the stuff that like, uh, is the i- ideal thing for you to be known for, not just the thing that can get attention, you know, quickest, because you're gonna end up in a bad place.

   4. HSHarry Stebbings48:36

      How staccato has your growth in subscribers been? And 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.

   5. TUTim Urban48:49

      Mm-hmm.

   6. HSHarry Stebbings48:49

      There was no like bang moment. It just gradually compounded over time. Was yours quite sta- kind of staccato up, flat, up, flat, or was it much more linear?

   7. TUTim Urban49:01

      Um, okay. 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, di- a steeper diagonal after something, after a big post, or sometimes it's a, 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 (clears throat) most of those people will come and then forget about you, 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 they'll ... It's like, so it's like, it's like a spike, and then when the dust settles, like, the, the base number's a little higher. So, there'll be those steeper moments, but then (clears throat) it's never totally flat because, specifically because of the nature of Wait But Why is the po- ... Like you mentioned, like, certain posts that are, um, (clears throat) um, evergreen, that are (clears throat) ... Um, they're kind of out there being salesmen all the time. So, like, there's always, uh, 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, or, you know, someone retweets your tweet, you know, even though you'd-

   8. HSHarry Stebbings50:24

      Ah.

   9. TUTim Urban50:24

      ... wrote it a bunch a long time ago. That, that tweet now just got you s- a few new followers. So, I think it's more like steeper diagonal, like, shallow

10. 50:31 – 53:54

    How to Motivate Yourself

    1. TUTim Urban50:31

       diagonal, steeper diagonal, um, or shallow diagonal.

    2. HSHarry Stebbings50:34

       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. (laughs) What do you know now that you wish you'd known?

    3. TUTim Urban50:44

       Um, I, I guess I just wish I had known, um, my, uh ... Like, I've gotten much better at managing my own issues. (laughs) 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, 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 lotta 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, 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-

    4. HSHarry Stebbings51:42

       What-

    5. TUTim Urban51:42

       ... this process, 'cause, like, it's ... Yeah.

    6. HSHarry Stebbings51:44

       What other mechanisms work for you? I love the pay. I, I do one myself. If I have a protein bar which I became addicted to, I will give $10,000 to a cause which I really dislike. (laughs)

    7. TUTim Urban51:55

       Yeah, cars.

    8. HSHarry Stebbings51:56

       (laughs) What other things work?

    9. TUTim Urban51:57

       Yeah. So, so, so, I mean, so there's two things baked into the 800 words a day thing I have going right now for this book. One is that it is, um, that, yes, there's external pressure, so you have to do it and th- you can't hide. Like, you have to do it and, um, and that feels like a school deadline. It doesn't feel good in those moments, but it's, it's specifically that negative feeling, and it's negative because you can't escape. You have to do it, so it's just, like, misery, 'cause I have to do this. And then you do it and then you feel so much better that you did it, as opposed to that, n- not as miserable but you're in a light simmering misery that lasts for weeks, because there's this dread of this thing you have to do, versus it's, it, it gets much higher 'cause you have to do it now, but then you do it. So, there's that aspect, like the external pressure, but the fact that I'm saying 800 words a day and not, like, 1,500 words, which I think old me would've said, "1,500 words a day." 'Cause I've done 1,500 words a lot of times on a day, but that's a good day, and you can't expect a good day. So, it's, like, what's, like, a 4 out of 10 day? Just do, make sure you have at least a 4 out of 10 day every day. And that compiles, you know? That compiles to-

    10. HSHarry Stebbings52:58

        Wha- why a 4 out of 10 day? Do you not ... Like, I'm always terrified of mediocrity. It's probably my biggest thing in life.

    11. TUTim Urban53:03

        Well, when I say 4 out of 10, I don't mean, like, the writing is a 4 out of 10 or, you know, my happiness-

    12. HSHarry Stebbings53:08

        Yeah.

    13. TUTim Urban53:08

        ... is a 4 out of 10. I'm saying that I just get a, a good hour, hour and a half of writing in. 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 2,000 or 3,000 words. Um, that's an 8 or 9 out of 10 day as far as pure productivity. But there's a ton of zeros in there, 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 a m- you know, a mediocre productivity day every day, 'cause that compiles, um, in, you know, eight months. You've finished a book.

    14. HSHarry Stebbings53:49

        How do you deal with and handle the critics, the shit feedback, the ones that say you're an idiot

11. 53:54 – 58:16

    How to Handle the Critics

    1. HSHarry Stebbings53:54

       and you're a moron and we hate you?

    2. TUTim Urban53:55

       (inhales) Um, so, uh, you as a blogger, I think it's ver- ... I think first of all, some people just shouldn't do this. If you, if you're gonna be really upset by that, it's gonna ruin your day. You know, there are some people who, they can read 100 positive comments and then one negative one and their day is ruined, right?

    3. HSHarry Stebbings54:11

       Yeah.

    4. TUTim Urban54:12

       And that's ... You know, I d- I think a lot of cr- creative people are like that and they persist anyway, but it can be really discouraging if that's how you feel. And so, um, the way I handle it mostly is I just remind myself of the big picture. So, sometimes there will be, I don't know, let's say, 500,000 people read a blog post. And, um, you know, you can look at, like, how many shares and likes there are, and there are, like, 80,000 or something like that. And then there are 300 comments, and 40 of those comments are really nasty and negative 'cause maybe this was a post ... You know, on my science posts or procrastination posts, there's almost no negativity. Um, there's some people that are thoughtfully correcting me, and that, I think, that doesn't even put me in a bad mood. I think that's interesting and I'm, like, so happy that I have, like, smart people here who are, like-... engaging in, you know, e- constructive disagreements. So, I'm talking about, like, if I write about politics or something, um, I'm gonna have, you know, a handful of nasty, you know, comments, you know, personal, whatever. Um, (clears throat) and so I'm like, "You can look at those and get upset, or you can say, '500,000 people read this. 80,000 people liked or shared it. 300..." So this is a very small, non-representative sample of the big group. It's the kind of people who comment, 300, and most of those, 85% of those were positive or neutral. And so we're talking about 40, and so then I would think, like, um, (clears throat) if there are a stadium full of 80,000 people who shared it and liked it, picture 40 people in, you know, in that stadium that, that are like, "This sucks." It, suddenly, it melts, rolls off your back, 'cause you're like, "This is not a b-" You know, it's like, it's, it's, A, it's inevitable. Like if you write something that, that has that about politics, that has a lot of attention, and it's not that... By the way, it's not that I think that only 40 people didn't like it. A lot of the 500,000 people, uh, who didn't like it aren't gonna comment. So it's not that I'm like, "Everyone loved this." No, it's like, yeah, some people didn't like it, but it's, if- it's inevitable. Um, if you're doing something that has a strong point of view, especially on something controversial, it's gonna piss people off. And, um, and so, I- I think you can do these kind of thought experiments. This is, A, inevitable. B, if you look at the whole big number, it's a small minority. Uh, C, that person who were saying something, you know, nasty, there's a good chance they: they barely f- follow you. A lot of times, these people aren't even fans of yours, they just came across it, and maybe that's their twelfth negative comment of the day on a blog, 'cause they're, um, just the kind of person, they're just going from blog to b- So, these kind of rational thoughts can just make the emotions simmer to being like, "Eh," and almost like you kinda laugh and just move on, and it truly doesn't bother you if you can get there.

    5. HSHarry Stebbings56:44

       Final one before we discuss one piece in particular, and then we'll do a quick fire. What piece are you most proud of, and which piece do you get most pushback on?

    6. TUTim Urban56:52

       I'm probably, I don't know, like, I'm proud of some of those, um, those long explainers, like the SpaceX post, I think was like, there was a big story to tell there, and I think I, after a lot of, like, thinking and toiling, like, came up with a very good way to tell that story, and I think I told it well, so I'm very proud of, like, that. Um, and I think that, that, uh, that, I know people that post, like, inspired some young people to go work at SpaceX and work in that industry, and so I'm, I'm very happy about that. Um, and what was the other question?

    7. HSHarry Stebbings57:22

       What, which p- piece do you receive the most pushback on, the most critic?

    8. TUTim Urban57:26

       Oh, without question, um, my stuff on, 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, f- without question, you know, just wading into the world of politics and political tribalism, um, you know, again, and 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 is 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.

    9. HSHarry Stebbings58:10

       And my mother always taught me, "You never talk about politics or religion at dinner parties." Uh, I always remember-

    10. TUTim Urban58:15

        Yeah, which is

12. 58:16 – 1:06:14

    AI Will Shake Our Civilization

    1. TUTim Urban58:16

       basically what I just did at a very public dinner party, so...

    2. HSHarry Stebbings58:18

       Very, very interesting choice. I do 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 in 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.

    3. TUTim Urban58:39

       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, eh, and artificial superintelligence, and that, and that the implications of the danger of these things is, are intense, and that they, uh, AI is probably gonna be dangerous not because it's gonna be evil terminator robots, but because it's gonna be super powerful with unintended consequences. Um, I think all of that holds up pretty well. And g- and, and, and to be clear, very little of that was my own research or principles. I, I, I was, I, I had a few major sources there. I had Nick Bostrom, Ray Kurzweil, and James Barrat, and, you know, uh, Eliezer Yudkowsky, a handful of the, you know, of, of people who basically I synthesized what they were saying and I tried to tell, you know, dis- distinguish which camps were, were which, and, um, what w- 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, a bird's eye view of what they're all saying, you know, and what, where is their, where is there 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 eight years later, so in a world that's of a, of a, technology that's changing so quickly, um, it's, it's, it's a snapshot of what we knew and thought in 2015. Um, and-

    4. HSHarry Stebbings1:00:10

       Is there anything you think you got wrong in the piece? Knowing what you know now, is there anything you would do differently?

    5. TUTim Urban1:00:16

       Um, (sighs) it's hard to remember the details, so I'm sure I, I could have probably run it by a f- a few real pros. I, I, I think I've heard some quibbles with some of, like, the technical specs I put in. Um, I, I think, um, I, I think that, I mean, I, know, knowing what I know now, I could also just explain a lot more stuff, you know, I understand it better, but I think, uh, I, I'll give myself a pass on most of that. I think 2015, it was a pretty, it was, it was about the best I could have done then, um, with the information that I had then. Um, with a-

    6. HSHarry Stebbings1:00:48

       I, I-

    7. TUTim Urban1:00:48

       ... time, with a time crunch.

    8. HSHarry Stebbings1:00:49

       I was running the other day, listening to you on This Week in Startups with Jason, uh, who we both, uh, 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 coming to fruition more than ever, how do you think about the most dominant ways AI can shape civilization to its core?

    9. TUTim Urban1:01:14

       I mean, civilization is just a bunch of people with a cert- a shared set of understanding of the world and certain set of norms and, and, and processes and systems, institutions that we all sh- share trust in. Um, and that is the s- 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 e- 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, it might be real people. No one knows, you know, you're listening to, you're seeing a tweet, you're listening to (clears throat) 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 sh- uh, 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 th- yeah.

    10. HSHarry Stebbings1:02:19

        I think about this a lot actually, and I think actually, like, so number one, verification as a layer becomes one of the most valuable. But I think value accrues to existing media brands because verification becomes more and more challenging. And so the authentic followership that we have becomes more valuable because it becomes more and more difficult to gain new authentic followership. Does that make sense?

    11. TUTim Urban1:02:42

        Yeah. Yeah. But I think that's also, you know, um, yeah, I think, you know, trusted, that's what's, you know, part of what concerns me about, like, so much of the media getting swallowed up by partisanship, is like, we really need, you know, well-known media brands or personalities or science institutions that we all can say, "Well, if they're saying it, it's probably true." Um, that creates, you know, once we have a sh- you know, that creates a shared reality. And I think that, um, we already see, of course, the fracture of the shared reality 'cause of tribal, you know, um, narrow cast media, you know, each telling their own story and social media, uh, creating bubbles of reality. Uh, and I think AI can just accelerate these trends. Um, (clears throat) the-

    12. HSHarry Stebbings1:03:28

        Got it.

    13. TUTim Urban1:03:28

        Yeah. Just, just the ability to spread misinformation, uh, and to have multiple different sources, you know, of misinformation being, um, just, you know, can cr- you know, uh, AI can create mass panic (laughs) with a certain kind of fictional news story, and that itself can then cause actual disastrous problems. Or, you know, someone with their AI can figure out how to shut down the power grid. I mean, there's just a lot of, you don't realize how much, you know, the, if the power grid goes down, we lose the internet, we lose, of course, like, all of our major, you know, h- home functions and everything, um, and just total chaos. You know, it's like, it's, civilization seems like it's all robust and works fine because, like, the power is always on reliably. The water is always coming out of the faucets. Like, if you just disrupt certain little key nodes here and there, you can shake these things that we all just think are automatic. Um, (clears throat) so we should always, like, appreciate that it is, even though it's robust, what, the civilization we live in, it's also fragile and, um, something, you know, really is a, some new s- major new source of power and intelligence just appearing on the scene, um, can absolutely, like, shake some of those fragile aspects.

    14. HSHarry Stebbings1:04:39

        I've been prepping for a show with Vinod Khosla, um, and he's spoken before about his concern around strong AI moving into the hands of the Chinese and de-globalization becoming more and more prevalent with these very segmented, really kind of silos of the world. Do you share his concern around the kind of segmentation of the world, de-globalization, and the ability for the Chinese to have such a stronghold on strong AI?

    15. TUTim Urban1:05:11

        Um, yeah, I mean, as an American who's used to feeling like, um, America is the most powerful country in most ways, so you get really spoiled by that where you just kinda think, um, "We're safe because we have more better technology and we have, um, bigger economy and a bigger military." You know, and that's, you know, and no one has the right to feel that way. Americans are very fortunate to have gr- uh, to have grown up, like, in a place where you just feel like, um, you know, no other country could, like, come in here and really do damage here 'cause we, we're America, you know. So yeah, as I'm, I think all Americans (laughs) should, if they're used to that, they should stop getting used to that and think like, "You know, it's, it's maybe not gonna be so stable and, um, simple as it has been." Um, but as far as, like, the bigger picture on like, um, (clears throat) on, um, like, the, the effect of technology on geopolitics, I'm just, uh, I'm not, I haven't done enough deep dive to really have a strong opinion in there that I'm not basically just regurgitating from some smart friend of mine. (laughs)

    16. HSHarry Stebbings1:06:12

        (laughs) Well, you'd be a, you'd be a true VC if

13. 1:06:14 – 1:09:00

    Are you optimistic about the future?

    1. HSHarry Stebbings1:06:14

       you were able to do that.

    2. TUTim Urban1:06:15

       Yeah. (laughs) Yeah.

    3. HSHarry Stebbings1:06:16

       Uh, then, then I would tell you your funds should be raised today.

    4. TUTim Urban1:06:18

       (laughs)

    5. HSHarry Stebbings1:06:19

       I, I just have one final one for a quick fire, and it's just, given the breadth of your research and work, and looking ahead, are you optimistic about the future for human civilization? Or does climate change, levels of debt, dangers of AI overcome that optimism?

    6. TUTim Urban1:06:37

       Yeah, it's interesting. When it comes to stuff like climate change, um, those problems I feel optimistic about because I'm like, I think that AI, if things go well, I think we're gonna have so many answers i- in the near future. I think we're gonna solve so many problems that seem really hard to us right now. I think 20, you know, these problems won't be a match for 2050s humanity. I'm incredibly optimistic about what could happen with health and human lifespan and, you know, just biotech and, and things like that. So, um, things that, that ha- had stressed me out, like the pro- the problems we currently have, I feel very, like, optimistic about. The problem is that the same thing that makes me feel optimistic about those, which is AI...... um, also makes me wonder whether the ne- the negatives of that thing are going to completely overwhelm the positives. Um, if we don't have a stable society, like, none of this matters. And, um, and so I do think there's like, um, you know, it's like, it's, think of it this way, it's like there is a spaceship coming towards us with super intelligent aliens on it, and we're pretty sure that they will know how to solve all of our problems. We also don't know what their deal is gonna be, whether they're going to want to hurt us or whether they're going to not care about us either way and they're going to, um, they're going to just start building stuff and take, you know, destroying our cities in, you know, without any concern for us either way. So would I feel optimistic? It's like on one hand, yeah, I, the problems we have, I'm like, "The aliens are gonna have answers, that's incredible. We've never had answers to any of these things." On the other hand, I'm like, "But the aliens are coming and that's pretty, like, terrifying." Um, so, um, so yeah, I think, I think it's like, I, I, I think, uh, the rational person in me would be like, no, I feel more pessimistic than optimistic. But I also am just kind of an optimistic person. I think a lot of times what comes, what these answers come down to is what's your, what, what, do you tend to be optimistic or pessimistic? And if you do, w- one, you tend to be that here. So deep down I still kind of feel like if I went in a time machine and got out in 2080, I'd be entering an amazing world, not a horrible dystopia. But I don't, now that I couldn't really defend that argument.

Episode duration: 1:15:14