The Exchanges

Q Why have you never done a venture? I'm totally going off schedule, but I'm loving this. Why have you never done a venture fund? It's perfectly placed. I would put a place, like, I could go on about this, why you should do it. Why have you not done it?

A 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 going to take a lot of time, you know, and it's going to take a lot of brain space. Um, and, and I just, uh, 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 want to call a blog post or a book. Um, and so I just, um, I kind of want to 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, this year probably, and it's like, that will be a different thing, but it's still the same. It's still, you know, it's, it's, it's about like expressing things that I'm learning or going out of 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 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. 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 kn…

AI assessment note: “That's going to take a lot of time, you know, and it's going to take a lot of brain space.”

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

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

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

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

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

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

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

A 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 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, megaviral. I'm like, no, this one, megaviral. 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 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 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 you first meet them, and then the flesh is, like, who 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. Means they have, like, a, they come off really, like, well, they're friendly, but…

AI assessment note: “I wrote a post on something called, like, the Apple game”

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

A Um, I'm not sure I'm a brand, uh, but, um, I, I, like, as far as, um, Like, having people know me for, like, the stuff I'm doing, um, it 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, 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, Um, for something that feels like this is what I'm doing now, but I really want to 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, 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 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.

AI assessment note: “having people know me for, like, the stuff I'm doing, um, it is totally great”

Q 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 deglobalization 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, deglobalization, and the ability for the Chinese to have such a stronghold on strong AI?

A 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 kind of 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, 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 because we, we're America, you know. So yeah, 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, 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, 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.

AI assessment note: “I haven't done enough deep dive to really have a strong opinion”

Q In terms of recapturing that structure, the realization of the freedom of 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 time. When did Wait But Why really come to be as a very viable pathway for you to pursue as a very meaningful career?

A So I, since I was, you know, I said like 1716, 17, I was like, I need to do something creative in the arts, you know, music or Writing, and I moved to LA after college to write music, and that was my first thing, and 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 going to 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 I was walking down the Manhattan Beach border walk 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 running this business with part of my time with you, and I need to let go. And so 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 where I held down the business. And now he was like, okay, why don't, you know, he's going to keep growing this and I'm going to go and take one of these creative pursuits and it'll be part of the kind of joint business World that we were in. And so I was like, okay,…

AI assessment note: “I'm going to go and take one of these creative pursuits”

Q Okay. So just try to 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 it.

A 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, 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 want to 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 a certain time, so I'll just kind of like write Um, you know, metabolism, blah, 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. I'll, I'll, I'm not going to bring out full paragraphs, because I have highlights for that, but I'll say, like, Dawkins, two 54, and I know that that's, like, the highlight at two 54. And, and as this happens, what happens is, you know, it's, it's like, early on, it feels, like, daunting, and you, 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, 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, yo…

AI assessment note: “I'll have like a text edit doc that's just very basic”

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

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

AI assessment note: “I was gonna put a section in my book about ice ages... if I feel bored... Out.”

Q 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?

A Yeah. So, um, this part is a fun process. I mean, it's because 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, it's, it's kind of exhilarating going from, I always use the, you know, the scale of like a, a, a, a 10 out of 10 knowledge is like the world's leading expert in 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 or something around there where I'm like, You know, I know something about, I know a decent amount about this, but, 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 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 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 bit many written, you know, written dissertation, you know, toiled through something like that and then had to defend it. No interest. No, there's to…

AI assessment note: “I always use the, you know, the scale of like a, a, a, a 10”

Q 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 deglobalization 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, deglobalization, and the ability for the Chinese to have such a stronghold on strong AI?

A 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 kind of 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, 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 because we, we're America, you know. So yeah, 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, 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, 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.

AI assessment note: “I haven't done enough deep dive to really have a strong opinion”

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

A Um, I'm not sure I'm a brand, uh, but, um, I, I, like, as far as, um, Like, having people know me for, like, the stuff I'm doing, um, it 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, 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, Um, for something that feels like this is what I'm doing now, but I really want to 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, 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 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.

AI assessment note: “it is totally great and gratifying because, specifically because, the stuff I'm doing”