The Exchanges

Q uh, you know, market first, and there's that great quote, like, uh, when a great entrepreneur meets a bad market, only one of them keeps their reputation, um, the bad market. And so how, uh, what's another example from your portfolio that you can think of that drives home this kind of, like, market first, where the market first approach led you to do something that, um, that worked out?

A Uh, you know, I did a lot of crypto investing in, like, twenty-seventeen-ish, twenty-sixteen through twenty-eighteen. And that was because there was such an obvious sea change from an adoption and sort of technology basis there. You know, the AI stuff is another one. You know, all the AI companies I invested in was a little bit like, hey, the market's shifting, the technology's shifting. The flip side of it is, there's lots of things that I invested in that only in hindsight could I come up with a theme, right? I invested in Notion, Airtable, and Retool within, I don't know, two years of each other, whatever the time frame was. But at the time, there was no low code, no code. Kind of thesis. It was just, these are really interesting founders working in interesting areas. And so in hindsight, there was a market, or at least there was a trend, but at the time it was just like, these are smart people working on good stuff. And so it's a little bit of that. Um, how do you balance both of those perspectives? And sometimes you're thesis driven and sometimes you're just like, you know what? The thousands of great founders out there working on ideas are going to come up with better ones than I am. And so, you know, let's, let's have an open mind on everything.

AI assessment note: “I did a lot of crypto investing in, like, twenty-seventeen-ish”

Q If somebody today had the freedom to do that, what, what would be your, what's Gil's guide to, uh, to that intensive travel? What would you tell, what, what, what was really transformative for you or like, what was your approach to that?

A Yeah, I think it's basically, um, spend at least a month in one city and adopt, decide to learn something there. And so, you know, maybe you want to go learn how to draw, or maybe you want to go to France and learn to To make pastries, or maybe you want to, you know, in my case, it was go to India and do this very intensive yoga experience, or maybe, you know, and, um, especially if it's part of a community that you join, you get really immersed in interesting ways and not just the topic, but also the people around it and the local people, right? Because then you're really forced to be part of something. There's actually a, a, a person I know who's about to start a company And I convinced him to go do this because he had an extra month or two, and he said it was like the best month he'd spent. He went down to Brazil and, um, Uh, enrolled in some classes down there, and you just spent a month doing it, and so I, I personally think it's super interesting, and how often in your life can you actually get a chance to do things like that, but also it is a different form of travel than, hey, I'm going to, um, you know, I went on a Chinese tour group of Italy once, and on these Chinese tour groups, they try to see as many cities as possible in as short a time as possible. That's check the box, right? Okay, there's the Leaning Tower Pisa check. We saw it. It's like you stop for 10 minut…

AI assessment note: “spend at least a month in one city and adopt, decide to learn something there.”

Q I remember when I lived in SF from 12 to 20, and I think there was a handful of schools that were started for elementary kids. Was Alt School one of them? And was there a Wonder School? Is that, does that ring a bell?

A Yeah, those were more kind of like, hey, we're going to use technology, etc. I don't think there's any need for technology. I think you just need a couple good teachers and like a reasonable curriculum. And so again, I, I think it's not that, that I'm not trying to reinvent the school system. I just think you could go back to certain types of basics. It's interesting. There's a school in San Francisco called proof school, which I think is fascinating. Um, I think their, their line or motto is like for kids who love math and have a very strong emphasis on mathematics and their curriculum. And, you know, kids are doing machine learning and like 10th or 11th grade. And, um, You know, I, I find things like that kind of inspiring where they're like, okay, we're going to take a different lens on it, and our lens is just kids who love math, and let's find out what's the right curriculum for those kids, and maybe some of the early literature classes emphasize sci-fi, because those are the types of books they like, and maybe the, the history we focus on is XYZ versus something else, and so I just think, um, that's a good example of like a really smart approach to schooling. Um, there's a variety of people who've done these Differentiated approaches.

AI assessment note: “Yeah, those were more kind of like, hey, we're going to use technology”

Q I remember that. It was up, was that up by Stockton?

A Uh, no, it was in the Bay. It was actually in the, in the, in the water. It was like a little island. And, um, you know, you, you, um, it was on the market for a while. I actually looked at it a couple of times in terms of thinking, huh, maybe this is the thing. Maybe this is the anchor thing, but I just think it's going to be so hard to do anything in the Bay area. Right. I mean, it's, it's hard enough to construct a public toilet. Like, are they really going to let you build a beautiful monument? Uh, right. Um, on any reasonable timeframe. Uh, but there, there's lots of other metro areas that are much more amenable to this, and there's a global version of this, and there's a US version, but often in, in major metros, it's the land, and then the construction actually isn't that bad because really what you're building is a big statue, and in some cases you're building out a base or foundation under it that may be part of a building. Maybe you want to build an elevator up if you have a big view or vista, but you're not building a large commercial property with all the plumbing and electrical and You know, all that extra stuff that goes into it, right? Often these things are kind of like hollow shells.

AI assessment note: “Uh, no, it was in the Bay. It was actually in the, in the, in the water.”

Q How many other, are there any other partners at your, like, shop, basically, or are you the guy?

A You know, I've, I've recently hired a few people to kind of help me in different ways. I think fundamentally what I want to do is, um, continue to build things, work on things, think about technology, like just take, I would call it almost like the anti-BC approach and be builder first. And so there's a lot of side projects that I, or me and my team are now working on. You know, we're working, for example, um, Shrein's helping me with, um, We're trying to take the, the, the thousand, um, most important books that are off of copyright and translate them into dozens of languages using AI and then create audio books off of any, off of all of them so people can download the great works. Of, um, history from anywhere in the world in any language. You know, we're doing stuff like that, and so that also forces us to really use different AI tools, and let's look at 11 versus Cartesia versus, you know, OpenAI, and let's, let's, how do you actually translate a long-form book with high consistency, and how do you QA that?

AI assessment note: “I've recently hired a few people to kind of help me in different ways.”

Q And why would that be the case? Like, why would we have an off button?

A You know, there's all these theories, and who knows? I mean, I don't, I'm, you know, I don't know. Uh, there's theories, but I don't know which theories, right? Um, and, uh, the, the other piece of information that we have is that we know that there's certain drugs that will extend lifespan in multiple organisms. You take a drug and, or you give a drug to something and it lives longer. Rapamycin would be an example where in mice, um, mice will live 10 to 30% longer based on actually their sex, right? So female mice, I think, will live longer than male mice on rapamycin. And then there's knockouts that you can do in genes. And if you knock out a gene or certain organisms will live a lot longer. And that means that you can develop a drug for it, right? That's how the drug industry works. You can do a drug that mimics a gene knockout or a gene up regulation, and you end up with the same effect. And so we know that you can make things live much longer. And there's very little being done in people around that. And so the question is why, right? And imagine if you had another 30 or 40 or 50 healthy years.

AI assessment note: “You know, there's all these theories, and who knows? I mean, I don't know.”