20VC: Scaling Wait But Why to 600,000 Subs; Behind the Scenes on The Research Process, How to Learn Entirely New Topics Fast, The Writing Process and Building Good Habits & The Distribution Process and the Business Behind the Blog with Tim Urban

14 Aug 2023 · 59 min

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In short

Podcast Episode Summary: The Twenty Minute VC (20VC) with Tim Urban

Overview In this episode of *The Twenty Minute VC*, host Harry Stebbings interviews Tim Urban, the co-founder of Wait But Why, a website renowned for its deep dives into complex topics illustrated with stick figures. The conversation covers Tim's creative journey, the evolution of *Wait But Why*, and his insights on writing, scaling, and the implications of artificial intelligence.

Key Discussion Points

  1. The Founding of Wait But Why
  2. A-Ha Moment: Tim shares the pivotal moment when he realized *Wait But Why* would be his life's work.
  3. Lessons Learned: Tim reflects on what he wishes he had known at the start, including the importance of focus and commitment.
  4. Fear of Constraints: Discusses his fear of being constrained by traditional work structures.
  1. Scaling Wait But Why to 600,000 Subscribers
  2. Viral Posts: Tim identifies the first piece of content that went viral and how it transformed the platform.
  3. Pride and Disappointment: He discusses the pieces he is most and least proud of, highlighting the emotional journey of content creation.
  4. Challenges of Scaling: Examines the hardest aspects of growing the audience and shares surprising elements of the scaling journey.
  1. Topic Selection and Writing Process
  2. Choosing Topics: Tim explains his process for selecting topics that resonate with his audience, balancing personal interest with audience demand.
  3. Writing Strategies: He shares his evolving writing process, tips for overcoming writer's block, and the significance of structuring his work efficiently.
  4. Research Process: Discusses how he researches complex subjects and prepares to write in an accessible manner.
  1. Distribution of Content
  2. Content Strategy: Tim reveals how he approaches the distribution of his content across various platforms, including newsletters and social media.
  3. Importance of Newsletters: Highlights the role of newsletters in audience engagement and growth.
  4. Content Extraction: Describes how he extracts social media posts from longer articles to maintain engagement.
  1. Views on AI and the Future
  2. AI Insights: Reflects on his past writings regarding AI and shares his updated views on its potential risks and benefits.
  3. Societal Impact of AI: Discusses concerns about the societal implications of AI, including misinformation and societal stability.
  1. Personal Reflection and Future Aspirations
  2. Criticism Management: Tim shares strategies he uses to manage negative feedback and maintain perspective.
  3. Personal Growth: Discusses his journey in managing his creative process and productivity.
  4. Future Goals: Envisions continuing to explore new media formats while retaining the core essence of his work.

Key Takeaways

  • Curiosity-Driven Content: Tim's unique ability to simplify complex topics stems from genuine curiosity and a commitment to deep understanding.
  • Embrace Challenges: Acknowledging personal fears and constraints can lead to greater creative freedom and productivity.
  • Value of Authenticity: Maintaining authenticity in content creation is crucial for long-term success and audience trust.
  • Adaptability: The ability to adapt to changing media landscapes and audience needs is vital for sustained growth.

Notable Quotes

  • "The same thing that makes me feel optimistic about future solutions also makes me wonder whether the negatives will overwhelm the positives."
  • "I always want to indulge my curiosity full time and work on stuff that genuinely excites me."

Conclusion This episode provides a rich insight into Tim Urban's creative processes, his journey with *Wait But Why*, and his thoughtful reflections on the future of AI and content creation. It emphasizes the importance of curiosity, authenticity, and adaptability in the ever-evolving landscape of media and technology.

For more information and resources, visit [The Twenty Minute VC](http://www.20vc.com).

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Transcript

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0:00I'm incredibly optimistic about what could happen with health and human lifespan. Things that had stressed me out, like the problems we currently have, I feel very optimistic about. The problem is that the same thing that makes me feel optimistic about those, which is AI, also makes me wonder whether the negatives of that thing are going to completely overwhelm the positives. If you don't have a stable society, none of this matters. So seven years ago, I remember sitting in a cafe in San Mateo and I got sent this incredible blog post by a friend on artificial intelligence. It was my first piece of weight -but -why content, and I've been one of Tim Urban's biggest fans ever since.

0:35He is the master of taking very complex things and making them immensely simple and understandable. Tim has scaled weight -but -why to 600 ,000 subscribers and a monthly average of half a million visitors. Tim's 2016 TED main stage talk is the third most watched TED talk in history with 66 million views. This was two content creators in Discussion State, there was no script just us shooting the shit. I hope you enjoy it, it was so much fun to do. But before we dive into the show's day, this episode is brought to you by Tegas, the go -to research destination for bold investing. Tegas curates, expert insights, analysis and financial data to give you powerful perspective for your investment decisions.

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3:22You are now arrived at your destination. 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. So I owe you for that, but thank you for joining me. Yes, thank you for having me and for being so well prepared. Oh, I mean, you're very kind. I stalk the shit out of you. So I'm ready for this, But I hate you, as with Shachy Stark conventionally, and so I wouldn't start with a bit of a weird one, but think back into when you were a child.

3:52What did you want to be when you grew up? Well, it depends on the age. Five, six, it would have been something to do with space or dinosaurs. Those were my two obsessions. So probably just, you know, yeah, astronaut, something like that. Then, by the time I was 13, 14, 15, it was like, I wanted Max attention, so like, president, ambition, like want max everything, you know, and precedent or something like that. 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. The pressure was too much. Too much? No. It was campaigning trying to get people's votes, and then for what?

4:33So that you can have, like, what's actually just kind of like a glorified bureaucratic administrative role? I was like, no, I don't want that. And then from then on, it was basically like, I probably wanted to be in something creative, music or writing. 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 arm -chest like all of this, but you know I'm a venture investor so we have a lot of time to think. My question to you is, what do you think you're running from and what do you think you're running towards Tim?

5:04Well, I'm probably running for me my whole first 22 years, some people a lot longer, 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. 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 a lot. And even then it can't, you know, so I loved can't, it's not like I hated school or can't, they were fine. But like, then you go to camp over the summer and still it was like, now we're going to soccer.

5:32Now we're going to basketball, now arts and crafts. And it was like running from that. I feel like a lot of my life has been and since then has been basically centered around not having, like total for, 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 p .m. that day I have something that's like the whole day is kind of like, I'm gonna bad with the whole day about it because I just want like total freedom. But why do you think that is? I'm the same as you. But why do you think there is that unwillingness to be constrained?

6:02You know, I always think of those two characters, there's this rational decision maker, this kind of a grown up. 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 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? 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 parts 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.

6:29We'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 structure and things, you can end up with the monkey kind of running your whole life suddenly. So now it's like they'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 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 am doing stuff that makes sense every hour, and I'm not just doing nothing.

6:59So I feel like there's so trying to now recapture some of that actual structure. In terms of recapturing that structure, the realization of the freedom of thought you have today with weight, but why? Came really with a couple of hit pieces, you know, one of them being the Fermi -powered or massive head at the time. When did weight, but why really come to be as a very viable pathway for you to pursue as a very meaningful career? So since I was, you know, I said like 17, 16, 17, I was like, I need to do something creative in the arts, you know, music, and I moved to LA after college to write music, like, and that was my first thing and it was blogging on the side.

7:33But then I started this business with my friend Andrew Finn. That was fun. We were ending this tutoring test prep company together and it was great. We were working with a friend, but I had this voice that was like, ah, this isn't the thing that you said you were gonna do. And so actually I talked to Ember. It was actually like summer of 2012. I was walking down the Manhattan Beach border rock 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 music right now on the side. I'm doing a blog on the side. I'm running this business with part of my time and I need to like go and so go on We do something you know where you know we've done this before where he went and worked on a project Why held down the business and now he was like okay?

8:07Why 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 were in amin and so I was like okay musical is fun But it's not a great business But writing can turn into like you know a media empire who knows like you know We hire a bunch of writers maybe it becomes a platform that can have influence not just interesting to me as a creative It can be interesting to you as well as a business person. So we were like, okay, that's a good choice. And the key was, I'm going full time. 60 hours a week on one project and that was wait for a while.

8:36And that was kind of the beginning. Then it took a year before I launched because of procrastination. And it was this thing I was going to do. But how do 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. Is every post like seven things I think about this, that, that, is it like that? Or is it longer things? Is it funny or is it? I don't know, I didn't know anything. Are we hiring other people? Is it just me? So for the sake of money, we were going to start with it being just me. And it was just kind of like, finally got it together in summer of 2013, got it started.

9:08When did you still make money from it? Pretty soon, it was about 10 posts in that one post really blew up. And suddenly there were decent amount of traffic after that. So we put Google ad words on. And that generated some money. But I hate it. It was like, this is so like not authentic. 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 that stopped and we turned to Patreon. Try that at the urging of a friend of my Philip Deppner from Kurtz Kassat.

9:38He was like, you got it. Just do it. So I tried it and it was great. And 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, start selling things, start doing some speaking. You know, there's a lot of ways to kind of cobble together revenue once you have a decent following. I'm actually never spoken about this, but I've never had the chance to as someone in this position. When you think about the revenue makeup of the business today, what does it look like in terms of Patreon to March to speaking? I'm happy to also share mine and Sherrod's, if interested.

10:07Yeah, sure. Patreon is bigger than merch, partially because we just haven't made that much new merch recently, but there's always new patrons. And speaking on a really good year can be bigger than both of them combined. I mean, you know, COVID, that goes away. So that goes on and off and then just put out a book for the first time. So that was a nice like one off, big chunk of revenue. Do you feel like you're selling your soul speaking? No, I don't actually because it's basically just me taking when I write in my blog and translating it to a different medium to speaking medium. I'm never gonna do what the conference wants me to do.

10:40If they say, you know, we want you to promote this company, I'm not gonna do anything like that. I'm gonna basically something like AI or the fairy paradox you mentioned. If there was a topic that I've written about that a conference wants me to speak about, I'll just go and do the talk version and there's slides and you know I did that with a TED talk with my procrastination post so that that's why I don't feel like I feel like it's just a way It's like taking content that if I draped 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 the way that the all the work I did for that AI post actually can turn into revenue is like it's it It comes later in form speaking.

11:09Do you worry that to scale your revenue and scale your media business? You lose the constraint -free life that you craved I've been pretty resistant to doing too much that's focused on revenue because of that. And the same reason that, you know, I, six years ago, we hired Alicia, who's the manager of lots of things, which is just like the second in command at WAPEY 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 could 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 work on stuff.

11:44Why have you never done a venture? I'm totally going on schedule, but I'm not even. Yeah, I've never done a venture fund. It's perfectly placed. I would put it placed. I could go on about this, why you should do it. Why have you not done it? 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. It's gonna take a lot of brain space. And I just feels like I got out of the business world so that I could just spend my time thinking about making cool pieces of creativity. I kind of want to just keep doing that. Until I'm bored, I don't want to 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.

12:19I'm like, well, you know, so I think like, look, there's a lot of, 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, 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 what we're doing. It's part of the thing I want to be doing and it also can make a lot of money.

12:47Then great, we should do that. But like, part of what's nice about having had that business before is that we have some other revenue sources that allows way, but why to kind of have pure motives and not have to do anything that I don't think it fits with the brand. I just think of venture investing like you have to have a brand that the best founders want to take. You have that with weight, 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.

13:26Across the venture landscape, you have those very synchronously with your business, plus with a 10 million dollar venture fund, which is quite small in venture funds, and actually you could raise it in an afternoon. Is it an hour or two a week? I do a lot of research, but it's not that often from start -ups. It's often in established companies or... Yeah, I think we're really being off -scrubs, yeah. Your benchmark of the world and the best funds will bring you in for your distribution reach intellect, thought. So you get incredibly high -quality flow. Your selection ability will be very high given the deep dives that you do.

14:03So I honestly think, yeah, you could constrain it. And then with a platform like Angelist, the back office and admin is minimal, minimal. Maybe it's not now or two, maybe it's half a day max four hours, but it's pretty light for a potential eight, 10 million windfall on a four or five X fund. And actually pretty good. Maybe we should talk more and continue talking me into it. Every time I hear anything like that, I'm always like, icky, icky, like other whole thing that I have to do. 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, oh so much like writing on E2D tomorrow and then I look and I'm like, oh second half of the day is blocked off for this VC I'm like, oh no, no, no, no, no, no, wait.

14:43That's always the fear of maybe that's two Maybe I go too far in that direction, but just like anything that's gonna start like having stuff on the schedule It feels very claustrophobic suddenly and it feels like it's like invading my space to just like think and learn and write But maybe again as I said, I'm also trying to run to trying to kind of get out of that mindset a little bit and like be more were okay with like having an efficient block for writing every day and it don't have to have the whole day open. That's a pretty big constraint if you have to have the whole day open you can't take on it.

15:09Tim, do you feel claustrophobic in relationships? Is light speaking to a mirror me? Actually, I don't. Well, I don't know because I wasn't in many relationships until I met my wife and so I'm not claustrophobic with her at all. We're very on the same page about, you know, we're both very independent. We also like coexisting in the same place, you know, but she's like very open to me just like really deep. If I need to focus on something like that's always okay and like I don't feel claustrophobic in this So I don't know if I would feel claustrophobic. Yes, I think if I were in a relationship where she was like, okay It's like 5 p .m.

15:39Works over for the day. Let's go do something here like, you know It's Saturday. We don't go on the computer's on Saturday I think I might want to like yes, I might want to run away. That's not my situation So by the way, I loved your piece on picking the right part And which gives it actually what I did want to talk about before I went drastically off piece there But it's actually 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 describe you as the most genuinely curious person they've ever met.

16:10My question from that was how do you determine between interest to pursue and write about versus those that you won't cover and won't write about an exam in deeper. It's like curiosity and kind of almost almost they just kind of excitement like first read about never link and I started to understand what they were doing. I was like jumping out of my seat to like write about it because it seems so cool. It seemed like a game to try to like take everything I was learning and like how would I if I had a bunch of friends sitting around like how would I explain this to them and like this like incredible story like how do I tell it okay but then there's also sometimes just like procrastination or life partner stuff like that that's not like necessarily curiosity as much as it is um I know I have a bunch of swirling thoughts in my head a lot of times those posts emerge from conversations with friends like we're always just talking about this I'm always thinking about my own work habits and procrastination of what's going on there in the head And I have this idea that this is characters in the head or I'm always talking about relationships with my friends And we were saying that these are the three things that actually matter, you know Or whatever they are and so then it becomes like the thing that would excite me there is like I'm gonna now take that kind of scatter thoughts and I'm gonna make an official framework Which is just the kind of thing I would just do when I'm procrastinating, you know Or like I would think we spend six million years since we diverged from chips 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, full monkey situation.

17:28And like, that's so interesting to me. So then I wanna like, okay, I'm gonna make a chart and like, I would just do that in my own, just to like be like, okay, so that's, you know, six million years and just say there's 30 years. So that's pre -generation, that's 200 ,000 generations. Okay, so if there's like a hundred, by the way, you know, that's 2000 in a row, and I try to picture, wow, that's how many, like, great, great, great, so 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. There's a lot of topics I'm not curious about, or that I think about writing about it, and I'm like, ah, sounds like you.

17:57There's a lot of stuff about philosophy. People talk about this self and consciousness. I'm kind of just like, it's just like, I don't know, it's abstract and crypto. People wanted me to write about crypto and I was kind of just 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. So it's just what kind of grabs me where it seems like a delicious topic potentially. When you find something who is a delicious topic, But you're not versed enough to write the incredible works that you do about it.

18:26But 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? This part is a fun process because it is the right topic. It's a fun process because it's just like fully indulging curiosity. I always use the scale of like a 10 out of 10 knowledge is like the world's eating expert in a 1. out of 10 is you haven't even heard of the topic. And so for most topics, on 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 and I could talk about it with smart people and not say anything stupid and I have a sense of how it works, but I don't actually really know what's going on here.

19:04You know, there's endless topics like this. So my goal is never to get to like the eight or nine or 10. That would take years. That takes, you know, years need to understand all the different schools of thought and how they interact with each other and you have to deeply understand the technical nitty gritty of it and have debated it and argued a bit, many written dissertation, toiled through something like that, and then had to defend it. No interest. No, I think that's a limit on how interesting, there's a diminishing return on excitement as you keep putting those years in. So for me, it's like, I wanna get from like a two or three, to a 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.

19:42So I don't know, I'm currently researching something on the origin of life. And before I was like, okay, there's like some kind of first cell. There's some kind of like early particle that has like the property of self -replicating and if it goes from there. So anyway, to answer your question, here's what I do at that point. Is I just, first I'm like, uh -oh, obviously, sometimes just start Wikipedia. Just read the Wikipedia article. Because Wikipedia is often a good overview of the schools of thought, of, you know, what's controversial, what's not. But I'll give something like that a try. I want to understand the shape of the topic that I need to, to even know where the holes are in my knowledge.

20:13And so then I'll read some articles, right? I'll watch YouTube videos are great just again. Just to start, I'll watch a YouTube video on one part of the topic and it's like, okay, it paints one of the facets of this shape. I'm in a different YouTube 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, I'll read a couple Richard Dawkins books and I'll read this a book called The Life in an Early Planet maybe. Partially as you read, you see the sources that you see people get brought up again and and you're ready to go read that person's book.

20:44Maybe I'll actually read the origin of species or skim through it or you know. But the big point here is I'm not worrying too much about each source. I'm just 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 because then that's nice to go back and just look through the highlights. Okay, so you just go ahead and 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 .scu .gul .com just trying to get it a framework back. Yeah, I'll have like a text at a duck.

21:13That's just very basic. If there's something, I'm like, oh, 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. So I'll like save the hyperlink that's at a certain time. So I'll just kinda like write metabolism, versus you know, YouTube. And then I'll hyperlink the YouTube to that place. So I can just go. And I just have a lot of that. I'm not gonna bring out full paragraphs because I have highlights for that, but I'll say like dockins, 254.

21:40or I know that that's like the highlight at 254. As this happens, what happens is it's like early on, it feels like daunting and you can feel the fog. You can see it's like, this I don't really get what they're talking about. What is metabolism exactly? Is it energy? When you process energy, you can feel foggy. And I know if I wrote at that point, someone who really knows the topic would win at the terminology that's not quite right in the way I'm talking about, it shows some ignorance. So 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.

22:13Like, it starts to make sense in what's really gratifying, is then I'll often go back and read the same source that I did earlier. I'll read the really good sources again now and 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 that's this really fun process, or I'll go rewatch a YouTube video that was a little confusing to make sure, because that's a test. Like, I should now be able to understand this YouTube video appropriately. Is there any fog still? Do you ever worry that a topic is too complex or intellectually challenging intense for a broad audience?

Read the full transcript

22:43When you talk about metabolism there versus whatever it was that you were talking about, I got no idea. It may be actually 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? No, because 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 read a book chapter or good blog post, I'll read, you know, five or six books, maybe more. I'll skin through chapters of other books and a bunch of papers and YouTube, or whatever.

23:15It'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 it stokes a metaphor that made me realize I have a better metaphor for this that I'm going to use. But I will note all these dopamine hit moments. I'm like, oh, that clicked, right? That's important. And at the end, basically my job is to, the origin of life is officially interesting, right? And now the question is, how deep do you go? So if you're like, you don't go deep enough. Now most educated people like, you're not teaching them something too new.

23:45You 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, I didn't really teach most people anything new there and it's not interesting because it's so broad So then you can go deeper right and it gets more to me gets more and more interesting And I know this because I use myself as the focus groups because I know what I just got dopamine hits from and I was like Oh, that is so cool, right?

24:15Okay, perfect because my readers are gonna think that's so cool too And then other things I'm like 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 deep so I'm using the origin of life But AI is like this. You can go, I can explain chat GPT. Again, if you explain it the really broad way, you'd say something like, this is a large language model, which allows you to ask questions and you use it the whole internet as data to answer them. Okay, not saying anything new there. I can go deeper and try to explain how large language models work and how this complex process of choosing the next word, using a brute force of computation, whatever.

24:51And okay, maybe that's more interesting. You can go really deep and start to explain how transformers actually work. and all these jargon and now you get to really boring again, right? And so at any topic you mention, you can keep going, keep going, keep going, till 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. Reasonably smart educated people who are very curious, but don't know that much about this topic, but they like to know more. What's that sweet spot of, you know, one of the things and the ways of explaining that they're gonna make them, you know, if I had dopamine hit every hour while researching, I want them to have one every minute while reading my post.

25:24Have 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 you'll interest resonate it with it Yeah, definitely some of this hard to know what specifically within the post resonated I think I had more granular information on like this paragraph board 90 % of people I'd be like oh shit, and 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 I think what would surprise me is which parts were most interesting Which post has done the worst that you thought would do while?

25:55It's a good question. In the first year of week, but why? My goal was to go viral most of the post. Then I started doing stuff that I thought would be fun to write about. But early on, it was like, let's get some readers here. And so, the first 10 posts, it was like, maybe this one, the mega viral. This one, mega viral. This one's hilarious. I'm like, nah, it wasn't hilarious. This one's going to be super controversial. I'm like no one cared. You know, there were definitely posts early on like that I thought this one like I wrote a post on something called like the Apple game that my friends and I love.

26:26So Apple has skin, flesh and then a core. So every person is kind of like that where the skin is like the vibe they give off when they 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. Maybe only their spouse or their best friends know maybe no one beside of them know. And so for each one of these you give a good or bad so someone can be like a good bad good means they have like a they come off really like well they're friendly but then you You get to know them better in their huge asshole, actually. And they like, we'll talk shit about those people that think they're friendly, but deep down, and they're sold, they're like, quite good.

26:54So it's like, they're a good, bad good. So anyway, this game is so fun, my friends, and I was like, this is gonna 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, it didn't catch. Meanwhile, then a couple weeks later, I write a post called Why Generation Why Yuppies Are Unhappy, which was the word that was before we called the millennials. It was like, right, before millennials became the topic, the term. But it was basically why millennials are unhappy. And again, it was the same exact feeling. I was like, this is gonna catch fire when I post it.

27:20This is like everyone's gonna, you know, this is gonna, and it totally did like that one God, 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. I think those are the hardest ones when you're like trying to go viral. That's like very hard to predict and you kind of get some luck. 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. 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.

27:48I 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, because they feature, I'm not saying Elon Musk haven't had them on the show, but 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? It's not that I don't chase viral anymore. For example, crypto would have been a perfect post. I know it would have been viral.

28:21It 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, write everything, talked to a bunch of people, written like the full of clip crypto explainer. But I just didn't want to. And I think early on, if I knew that I had almost a guarantee million people in the first few days viral post, I would have done it. It was just that it was like, take that. I was amazing. People are going to... But I built up a readership now where it's like, one viral post doesn't do that much for that readership.

28:53And I kind of already have what I wanted during those early days was a regular sizable readership. So now that I have that, my external motive now is more about the existing readership and putting out something that they love. Like that's, that's great. Like if I think like my actual reader is well like, love this, then that's very exciting versus like, this is gonna like go viral and a ton of new people are gonna like learn about what I'm like, that doesn't, that doesn't do it as much for me. We mentioned the incredible research that you do, how you bring it all together. Now we need to get to the writing phase.

29:25What 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? Yeah, well, man. I mean, so blog posts is one way, right? It's like, I would have done all my research. I learned this shit out of the topic, right? Built the framework in my head for how I want to explain this psychological thing, and I've toiled over the outline and I know what I need to know, and I have this plan and now I'll go right. I can usually pound out. I can have some pretty big days there. 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.

30:04My first real book that I just published in February, 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 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. So I think blog post is a small enough thing that I think I can just kind of like get into a multi -day flow when you're just 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 you just like abs and mind you like a granola bar and you're eating it while still typing and like there's no inclination to procrastinate or do anything fun because you're just like on a mission and you're probably usually for me because I'm I'm panic because I'm like I need to finish this thing.

30:46So that's a not a pleasant zone to be in but that's on a lot of weight but I've post have been written in that zone. A book you can't be in that zone for four months straight or however long it takes six months to actually type the words. So for this book I'm working on now I'm on on a pretty strict regimen of I have to do 800 words, new words a weekday. And if I get behind one day, because I'm doing extra research, then I have to catch up later that week. You have a high -five for Rites' blog. Yeah, I mean, I call it like a snag. I think fiction writers must really have like, a certain kind of writer's block when they just don't feel like they feel very like untalented, you know?

31:18And it's like, you feel like I used to do this. I don't know how anyone does this. I'm not going to do this. So I feel that sometimes for sure. But mine's a version of it like maybe a more nonfiction version where I'll just hit a snag where 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 you'll want to do anything other than this project, just hugely procrastinating inclination in that moment.

31:43So I have a huge moments of despair. And in those moments, and this is, I think, a lot of anyone doing creative projects, 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 definitely, definitely get there. What do you do when you hit the snag? Well, I think if I don't have the right external pressure on me, I procrastinate. It'll just destroy my productivity for weeks on end. While I just each day avoid getting into it and get into it and I'll research instead of trying to write, then I'll try to re -outline the whole thing and then I'll think that's a good thing in the next day I wake up and I hate the new outline and it's just unpleasant.

32:21I say two things on content and winning a content. One consistency is everything. You'll read a haste to know or you'll consume a haste to know when the next thing is coming. It needs to be a habit in the consumption. Do you agree with the importance of consistency? I think it's very important when you're getting started. It's critical. I think early on, I started with a new post every Monday and Thursday and then I changed it to every Tuesday. For the first year, while I built up my readership, sometimes it was Wednesday, even Thursday, but it was a new post every week. That was, I think, very important for the first year.

32:50And at that point I had a big email list and a big email list makes it less important to have consistency I still think it's better than not. It's not ideal the way I do things But I'm very inconsistent now. I'll disappear for a while and then I come out with something big and that'll disappear for a while The big email list and social platforms they make it less important because I can ping the email list is what it's done So it's like then they all come who to read it that as opposed to if the only way people are seeing yourself as if they think to come to your site to check if There's something new you've got to be consistent if that's the main thing going on Agreed.

33:19The nice thing I say is that she volume is everything to stay. It is purely a game of output. You need YouTube shorts, you need Instagram reels, you need TikToks, you need podcast apps, 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 to stay more than anything actually. I think you'll disagree but I'm intrigued to hear your thoughts. The way I view it is, where can this just without any work also create stuff on other platforms? So if I did drawings, which of those drawings are good standalone Instagram posts?

33:53Or tweets? Which ideas, as I did it, from the researcher from the post itself, like our good tweets or whatever? If and when I have a video podcast, okay, let's make clips for Instagram Reels and for TikTok. It's a very good bang for your buck too, basically photocopy parts of what you've already done onto these other platforms. I don't think 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 TikTok. So we need to start doing video to make sure we have stuff on TikTok. I think they should focus on doing an A -triple plus.

34:25And then that one thing, spreading it on as many social places that make sense for that particular thing. And just focusing on that, that's what I think. I think someone who's crushing it on TikTok doesn't also need to have a big Twitter. I don't think they need that. The one argument to have something going on in every platform is platforms change and you don't want to have it's like diversifying your attention portfolio. You want a de -risk and not say, oh well, you know, if everything's in Facebook and Facebook comes unpopular, you just lost everything. So you want to diversify. I always say also whatever time you spend creating content, you should spend the same time or more distributing.

34:58How do you approach content distribution today? You press publish? What then? Honestly, we're not, we could be doing better at this. Like, right now if it's a blog post, I'll publish something and then I'll probably like, I'll pull out into a folder a bunch of things for Did this is a bunch of good Instagram posts that can come out of this post? Here's a bunch of tweets and you at least you might post it published them over the next couple weeks For the book that I publish like we can pull out a bunch of social content that can be done for the book But basically our day one we have a very specific regiment which is publish 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, Patreon, be sure to let patrons know the night before, right when it comes out, be a little before everyone else.

35:39And that's about it, you know, and then after that, like 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. But like I do a very basic 2015 technology job at this. I'm sure some people are very more sophisticated than I am. We have seven full -time and dual form video. Yes, well, I should be asking you the questions of the other way around. It's great as so much opportunity. Look how big you are without S. Do you enjoy being a brand yourself? I'm not sure I'm a brand, but as far as having people know me for the stuff I'm doing is totally great and gratifying.

36:14Specifically because the stuff I'm doing feels very true to me. It feels high quality and it feels like the real thing I should be doing. I think that I've enough experience this. Whether you're known publicly or just amongst 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. It's like a little soul crushing doing your stuff. And that's why I think it's really important if you are gonna especially do like kind of create creative stuff. Do the stuff that like is the ideal thing for you to be known for, not just the thing that can get attention, quickest, because you can end up in a bad place.

36:49House to Carso has your growth in subscribe as being. 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 it was quite kind of staccato up flat up flat or was it much more linear 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 I would say I'm in the middle where it's like a steeper diagonal after a big post or or sometimes it's a tweet, you know, sometimes I'll put out a tweet that happens to go super viral.

37:27A bunch of new Twitter followers come in and then like the blog traffic spikes. And then most of those people will come and then forget about you, even if they like what they see. But the people that happen to love it, they'll stay. It's like a spike and then the dust settles like the base number's a little higher. So there'll be those steeper moments, but then it's never totally flat, specifically because of the nature of weep, but why is, like you meant it, certain posts that are evergreen, they're kind of out there being salesman all the time. So like there's always some traffic on the really popular posts even years after they're written.

38:00So when you put workout like that, it's always going to be building your audience. You're obviously going to be kind of building on its own, where people are, you know, someone retweets your tweet, you know, even though you wrote a bunch a long time ago, that tweet now just got you some few new followers. So I think it's more like steeper diagonal, like shallow diagonal, steeper diagonal, more shallow diagonal. Tim, what do you know now that you wish it known when you started? There's a lot in terms of all growth that I wish it known. What do you know now that you wish it known? I've gotten much better at managing my own issues.

38:31I wish I'd taken my own issues dead seriously from the beginning and been like, the first year or two. There was such excitement and such pressure to be consistent that that wasn't an external deadline. But when there's less of that, like I just described, I would go and hit a snag and and it's like three weeks. Now, I feel like I've gotten way better at managing my own situation. So if I have to do a certain amount per day, or else I have to pay my friends a whole lot of money, and they can see the Google Docs, so like it's no way to hide. The snack just doesn't last that long. You just push through it, you force through it.

39:03So I've learned a lot of mechanisms like that that are helping me be like a lot more productive and a lot less miserable during this process. What are the mechanisms worth for you? I love the pain. I do one more slide. like if I have a protein bar which I became addicted to, I will give $10 ,000 to a cools which I read this like. So there's two things baked into the 800 words a day. Thing I have going right now for this book. One is that yes, there's external pressure so you have to do it and then you can't hide and that feels like a school deadline. It doesn't feel good. It's specifically that negative feeling and it's negative because you can't escape.

39:36You have to do it so it's just like misery because 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 not as miserable, but you're in a light, simmering misery that lasts for weeks, because this is dread of this thing you have to do versus it gets much higher because you have to do it now, but then you do it. There's that aspect like the external pressure, but the fact that I'm saying 800 words a day, not like 1500 words, which I think old people would have said 1500 words a day, because I've done 1500 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 four out of 10 day?

40:07Just to make sure you have at least a four out of 10 day every day, and that compiles. Why are 4 out of 10 days? You know, like, I'm always terrified of mediocries. Probably my biggest thing. Well, when I say 4 out of 10, I don't mean like the writing is a 4 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 look at all the days I've written in the past, there are a lot of days better than that, where I've really gotten into a 3 or 4 hour flow and written 2 or 3 ,000 words. That's an 8 or 9 out of 10 days, as far as pure productivity. But there's a ton of zeros in there.

40:38A miserable zeroes, tons and tons of zeros, and so 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 mediocre productivity day every day because that compiles in, you know, eight months you finished a book. How do you deal with and handle the critics? The shit feed back, the ones that say you're an idiot and you're a moron and we hate you. As a blogger, I think first of all, some people just shouldn't do this. If you're going to be really upset by that, it's going to ruin your day. You know, there are some people who they can read 100 positive comments and then one negative one in their day is rude, right?

41:11And that's I think a lot of creative people are like that and they persist anyway, but it can be really discouraging if that's how you feel. And so the way I handle it mostly is I just remind myself of the big picture. So sometimes they will be, let's say, 500 ,000 people read a blog post and, 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. 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.

41:50300. 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 if there are a stadium, a full of 80 ,000 people who shared it and liked it, Picture 40 people, you know, in that stadium that are like, it is sucks. Suddenly, it melts the rolls off your back because you're like, Hey, it's inevitable. Like, if you write something that has that about politics, it 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 who didn't like it aren't going to comment.

42:17So it's not that I'm like, everyone loved this. No, it's like, yeah, some people didn't like it, but it's inevitable. If you're doing something that has a strong point of view, especially on something controversial, you're going to piss people off. I think you can do these kind of thoughtless spirits. This is A, inevitable, B, if you look at the whole big number, it's a small minority. See, that person who was saying something nasty, there's a good chance they barely follow you. A lot of times these people aren't even fans of yours. They just came across it. And maybe that's their 12th negative comment to the day on a blog.

42:43Because they're in just the kind of person they're just going from blog to blog. So these kind of rational thoughts can just make the emotion simmer to being like, and almost like you kind of laugh and just move on. And it truly doesn't bother you if you can get there. Final one before we discuss one piece in particular and then we'll do a quick fight. What PC most proud of? I'm proud of some of those long explainers like SpaceX posts. 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.

43:13I know people that post like inspired some young people to go work at SpaceX and work in that industry and so I'm very happy about that. Which piece do you receive the most pushback on the most critic? Oh without question the stuff on this this last book I wrote and the series before, just anything to do with American politics. There is not any single thing you could write about American politics that some people won't hate in America. Hate. So without question, just waiting into the world of politics and political tribalism, 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, I'm so disappointed, this coming from you, I used to respect you as a lot of that.

43:47And, and you know, that's okay. I'm sad, I'm like, I wish all the readers liked it, but like, it's inevitable, and you don't write about politics if you can't handle some of that. And my mother always told me you never talk about politics or religion at dinner parties. Yeah, which is basically what I just did at a very public dinner party, so. Very, very interesting choice. I do have to ask about the AI article before we do a quick fight. As I said, I studied a year ago to hopefully get a job in venture at word. Well, for me, when you look back on the piece, it was 2015, so much has changed eight years on.

44:15What do you think you got right with the piece? I'm sure you've reflected on it a lot, especially recently. I think that the general principles are pretty much correct. The concepts that there's narrow intelligence and general intelligence and artificial super intelligence and that the implications of the danger of these things are intense and that AI is probably going to be dangerous not because it's going to be evil terminator robots, but because it's going to be super powerful with unintended consequences. I think, oh, that holds up pretty well. And to be clear, very little of that was my own research or principles.

44:49I had a few major sources there. I had Nick Bostrom, Rick Kurzweil, and James Barat. Basically, I synthesized what they were saying, and I tried to distinguish which camps we were rich, which is, again, part of my job 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 try to give a bird's eye view of what they're all saying, you know, and where's their agreement and disagreement? What's the best case scenario or worse? So I think it did its job. I'm proud of that piece. I think it holds up pretty well.

45:16Obviously, it's eight years later. So in a world that's of a technology that's changing so quickly, it's a snapshot of what we knew and thought in 2015. Is there anything you think you got wrong in the piece knowing what you know now? Is there anything you would do differently? I could have probably run it by a few real pros. I've heard some quibbles with some of like the technical specs I put in knowing what I know now. I could also just explain a lot more stuff. Well, you know, I understand it better, but I think I'll give myself a pass on most of that. I think 2015 it was about the best I could have done then with the information that I had then with a time crunch.

45:49I was running the other day listening to you on this week in startups with Jason, 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 sort 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? I mean civilization is just a bunch of people with a certain shared instead of understanding of the world and certain set of norms and processes and systems and institutions that we all share. Trusted, those are the support beams of the house for it.

46:26And AI is a giant seismic asteroid landing in a fairly fragile set of equilibria, and it can very quickly, what if we don't 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 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 all take for granted that create a lot of stability. 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.

47:14Does that make sense? Yeah, I think, you know, trusted, that's what's, you know, part of what concerned me about, like so much of the media getting swallowed up by partisanship is like, we really need well -known media brands or personalities or science institutions that we all can say, well, they're saying it, it's probably true. That creates a shared reality. And I think that we already see, of course, the fractured of the shared reality, because 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, just the ability to spread misinformation, and to have multiple different sources of misinformation, AI can create mass panic with a certain kind of fictional news story, and that itself can then cause actual disastrous problems.

47:57Or 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, if the power grid goes down, we lose the internet, we lose all of our major pump functions, and every and just total chaos. You know, it's like, its 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 faucet. It's like, you just disrupt certain little keynotes here and there. You can shake these things that we all just think are automatic. So we should always like appreciate that it is, even though it's robust, what with the civilization we live in, it's also fragile.

48:29And something really is some major new source of power and intelligence just appearing on the scene. can absolutely like shake some of those fragile aspects. I've been prepping for a show with Vinnie Kostler, and he's spoken before about his concern around strong AI moving into the hands of the Chinese and de -globalisation becoming more and more prevalent with these very segmented silos of the world. Do you share his concern around segmentation of the world, de -globalisation and the ability for the Chinese to have such a strong hold on strong AI. Yeah, I mean, as an American who's used to feeling like America is the most powerful country in most ways.

49:10So you get really spoiled by that where you just kind of think we're safe because we have better technology and we have bigger economy and a bigger military and no one has the right to feel that way. No other country could like come in here and really do damage here because we were America. I think all Americans should, if they're used to that, they should stop getting used to that and think like, you know, it's maybe not going to be so stable and simple as it has been. But as far as like the bigger picture on like the effect of technology and geopolitics, 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.

49:42Well, you'd be a true VC if you were able to. Yeah. Yeah. And then I would tell you your funds should be raised today. I'd go on, on a one for a quick one. 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 of that, dangers of AI overcome that optimism. Yeah, it's interesting. When it comes to stuff like climate change, those problems, I feel optimistic about because I'm like, AI, if things go well, I think we're gonna have so many answers in the near future. I think we're gonna solve so many problems that seem really hard to us for right now.

50:18You 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, biotech and things like that. So things that had stressed me out, like the problems we currently have, I feel very optimistic about. The problem is that the same thing that makes me feel optimistic about those, which is AI, also makes me wonder whether the negatives of that thing are going to completely overwhelm the positives. If you don't have a stable society, none of this matters. 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.

50:54We also don't know what their deal is going to 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 just start building stuff and destroying our cities and without any concern for us either way. So what I feel optimistic, it's like on one hand, yeah, the problems we have on 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, the aliens are coming and that's pretty like terrifying. So yeah, the rational person to me would be like, no, I feel more pessimistic than optimistic, but I also am just kind of an optimistic person.

51:23I think a lot of times what comes with these answers come down to is, do you tend to be optimistic or pessimistic? And if you do, one you tend to be that here. So deep down, I still kind of feel like if I went into time machine and got out in 2080, I'd be entering an amazing world, not at a horrible dystopia. Listen, I want to move into a quick fire around my friend. So I say a short statement, you give me your immediate thoughts. Does that sound okay? Let's do it. Okay, so what piece of content has been most transformative to your thinking in general? Wow. Now I always like to cite like the fountain head as a book that crystallized a really important concept in my head.

51:54It's about reasoning from first principles versus is reasoning by analogy. I think it's a great book and people should read it. And then like, I've had my whole world view clarified and sharpened by listening to great history podcasts over the last few years. Dan Carlin's hardcore history, strides, history of English, fall of civilizations. You know, so there's, I love history podcasts. 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. What's your biggest regret?

52:23First thing they've helped to mind is like all of my recent stock decisions if you could combine those all into one giant regret Just like the last three years of like any kind of investment decisions I was like let's do a huge huge investment right at the peak in 2021 before everything crashed I sold Tesla at like when it was at 700 before split so it was like one eighth or tenth of what it is now I made a couple good ones along the way, but it's like just just soul crushing What have you changed your mind on in the last 12 months? But AI, I had 12 months ago, I had any inkling that AI might steal my job within like two years.

52:59I would have guessed like 20 and that's one of a hundred different things that I've been shocked about with AI in the last few months, like everyone else. Do you change how you do what you do with that realization? Not really. It just makes me want to diversify a little bit. I was already going to start a podcast, but it makes me want to do that sooner. Because it's like, let's not have articles be the only thing. I'm going to do my thing and when that comes and changes things, I'll adapt then and and I'll figure out ways to do things in a new way if I have to. Will Elon Musk be successful with Twitter?

53:28You put me in a time machine five years from now? My gut is I come out and it yes, the answer is yes. Just because this guy does things well, and something that takes so while, right? And it's gonna be a lot of experimentation. It's gonna be a lot of failure along this experimentation way because that's how a real experimenter does things. They're fast and dirty and they make a bunch of decisions that they're like, oh, that was. So I think it's gonna be a rocky road, but I think it ends up in a place where we're like, oh wow, this actually now, it's like suddenly we realize like this app is better than any of these others and you know and it'll happen eventually You can choose a dinner party guest anyone that are alive Who would it be if there's no translator like Richard Feynman and if there is a translator or someone weird like Genghis Khan Just because like what the hell is he going on in his head like if we if I could just talk to him and be like tell me How you think about the world that would be cool I got asked one of penultimate one on the whole day the other day by a friend and they said, what questions do you least want to be asked when being asked questions?

54:23Probably at this moment, like, what are your thoughts on, like, you just did one of these, but it was more about Twitter. What do you think I'm like Elon? And it's like, I don't wanna dive into a world of very annoying arguments. When I just, I zoom out and I'm like, this guy is doing awesome shit. And so I'm sick of that question. I get it all the time, because I wrote a lot about him. So what a shit question. I mean, he would ask that, right? You're supposed to be different, because it was about Twitter. I don't mind that question. I just tweeted that X will be the most successful rebranding for the last five years.

54:52My Twitter is now like, this guy is the epitome of a moron. Yeah, it's one of the stupidest worlds to wait into right now. I've seen so many of those. Like, this guy is my joke of the day. And I'm just like, yeah, give it five years. And I think those people will look stupid. Final one. Tim, next five years for you, we sit down in 2028. Why do you want to be then? I would like to be doing what I'm doing now and delging my curiosities and making cool things for readers Except I'd like to be doing it maybe on a bunch of different platforms videos, some audio, some TV maybe some more books So I don't know I want to keep experimenting I hope I'll discover a couple new mediums that really work for me because I don't want to just get lazy and just stick with the one kind of thing that I Be started with so yeah, I hope I'm doing the same thing but on a lot more a lot more ways Listen, I've been such a fan of your work for such a long time having the chance to do this with you's immensely special for me.

55:46So thank you so much for being so open and for joining me stay Tim. Of course, any time, thank you. I mean, I just absolutely loved doing that. If you want to see more from us behind the scenes, of course you can watch the full video on YouTube by searching for 20VC. We always love to see you there. But before we leave you today, this episode is brought to you by Tegas, the GoTo Research Destination for Bold Investing. Tegas curates expert insights analysis and financial data to give you powerful perspective for your investment decisions, with lining fast access to over 60 ,000 transcripts across 20 ,000 companies.

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58:21As always I so appreciate all your support and we bring you an incredible episode this coming Wednesday with Brian Balfour at ReForge.

From the publisher

Tim Urban is the writer/illustrator and co-founder of Wait But Why, a long-form, stick-figure-illustrated website with over 600,000 subscribers and a monthly average of half a million visitors. He has produced dozens of viral articles on a wide range of topics, from artificial intelligence to social anxiety to humans becoming a multi-planetary species. Tim’s 2016 TED main stage talk is the third most-watched TED talk in history with 66 million views. In 2023, Tim published his bestselling book What’s Our Problem? A Self Help Book for Societies.

In Today's Episode with Tim Urban We Discuss:

1. The Founding of Wait by Why:

  • What was the a-ha moment for Tim that Wait but Why should be his life's work and sole focus?
  • What does Tim know now that he wishes he had known when he started?
  • What does Tim believe he is running away from? Why is he so fearful of constraints?

2. Wait But Why: The Scaling Journey to 600,000 Subs:

  • What was the first piece to really go viral? How did that change the trajectory?
  • What single piece is Tim most proud of? What piece is he least proud of?
  • What has been the hardest element of scaling Wait But Why?
  • What was the most surprising and unexpected elements of Wait But Why's scaling?

3. Topic Selection: Choosing What To Write:

  • What does the process look like for Tim when deciding what topic to write about?
  • How does Tim know what his audience will want to hear about vs what they will not?
  • What topics has Tim thought would be interesting but post initial research, are not?

4. The Writing Process:

  • How does Tim approach the writing process? How has his changed over time?
  • What mechanisms does Tim put in place to avoid writers block?
  • What are some of Tim's biggest tips to aspiring writers and authors?

5. The Distribution Process:

  • How does Tim approach distributing the content once produced? What works? What does not?
  • Why did Tim choose newsletter, Twitter and Instagram as his channels of choice?
  • How important has the newsletter been to the growth of the business?

6. AI: Super-Intelligence and The Future:

  • On reviewing his pieces on AI back in 2015, what does he believe he got right? What would he change with the benefit of hindsight?
  • Is Tim more or less positive looking forward at AI proliferating through all of society?
  • What is Tim most concerned about in the world right now?

More from The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

All 520 episodes
20VC: Scaling Wait But Why to 600,000 Subs; Behind the Scenes on The Research Process, How to Learn Entirely New Topics Fast, The Writing Process and Building Good Habits & The Distribution Process and the Business Behind the Blog with Tim UrbanThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 59 min
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