The Exchanges

Q Is that a good question to ask? Should somebody ask somebody?

A Probably not. Like, I don't think you should use, it's a very heavy sounding ask, you know. I think, and, and so, um, I'll give you, I'll give, I'll give your listeners a cheek. I still hope they buy the book, but I'll give them, like, my first thing on mentors is, um, take the Take the, people overshoot. They try and go too high. Like, and so take all, I think it's awesome to identify the people in the field you're gonna go after that you hold in highest regard and respect the most. Call those your aspirational mentors. Create a file, you know, in whatever digital folder type thing you like to use, Notion or, or Google Docs or whatever. Create a file for each one of them. And study them relentlessly. Find every podcast they've been on, find every YouTube, any interview you can find, anything they've written, put it in the file. Like, keep, keep it like a, like a little journal of yours for each one of them. One day you may meet them, and the fact that you've done all that work will make you much more likely to be able to engage with them, but you're gonna learn so much along that way. So, so the ones you thought you were gonna cold call, don't do that. Do that, do what I just said. And then For the ones you're going to actually try and meet, just go down a few levels. Like, if you go down a few levels, you're going to be asking someone for advice that's never been asked for ad…

AI assessment note: “Probably not. Like, I don't think you should use, it's a very heavy sounding ask”

Q to lose that, sort of, when we started investing in venture, and I definitely had to lose that when I got on the internet, because it's a, like, I've realized collaboration works a lot more. But I'm curious, you're still a competitive guy. Like, you're a former, you know, basketball player. You're competing in deals. So like, Should you try to crush your competition or should you work with them?

A Well, the, the, the advice in the book, most of it that gets into this topic you're, you're hitting on is in a chapter called embrace your peers. And it's probably my favorite, um, principle in the book. Um, but mainly because I think it's the most unique of all the, of all the points that I, that I make. And, um, I, I've found, I found some amazing stories that, that I share in the book that you can go read, but Like I found that far too often humans, and I'm not talking about companies, like I'm talking about, I'm not saying companies need to have friends, but like they probably do, but, um, humans when they're out trying to climb up the ladder, um, would do themselves a massive advantage if they would embrace a group of peers. So finding five to 10 other people who are climbing the same ladder you are and, um, share, collaborate, Um, and support one another. And the number, you know, the, the, you, you learn faster. Your network is bigger because it's not just your network. It's the group's network. Um, If it's authentic, they will be there for you on the hard days. And that will really matter. Like that will really, really matter. Like in ways it's, it's, if you haven't been through it, it's really hard to say how big a deal that is. Um, and, um, and you'll have fun and you'll sit like one way to know if you're really doing it right. When they win, you're sincerely happy fo…

AI assessment note: “humans... would do themselves a massive advantage if they would embrace a group of peers.”

Q Do you have a way of sensing if somebody is just going to stay in it until they either do it or they break them?

A There's a couple things you can look for. Like, did they fall into it, um, opportunistically? Because then they might not It might not be there, you know. Um, and some people, I remember, I remember when we did the first Uber investment, um, Travis, his, his first couple of companies, one of them I think ended up in bankruptcy, the other one they like got money back, but, um, It was pretty obvious he hadn't touched the brass ring and really, really, really wanted to, and he could sense that this thing was gonna work, like, way bigger than the first two he was on, and I could, I could just tell he wasn't, he wasn't gonna, you know, he wasn't gonna not lean in as hard as he possibly could. You could feel it.

AI assessment note: “There's a couple things you can look for. Like, did they fall into it”

Q Fascinating. So what do we do about that?

A Well, I, here's what I fear we're going to do about it is, uh, this is really off the subject, but what I fear we're going to do is the two leading players will recognize the threat and weaponize regulation, which is what they're, they've, they started doing three years ago, but, um, no one's funding more lobbyists, um, begging for AI regulation than Anthropic themselves. And, um, And they'll use that to try and deal with the threat. What's really going to be interesting is the rest of the world. So in, for the past hundred years, I think the U.S. has considered rest of the world their, their market. Like, and that's true in industrial type products, but it's certainly true in technology. And if you look at the internet, um, you know, China kind of had a fence around it. And the rest of the world use the U S products. They use Google and Amazon and Uber and, you know, all these things. And if we pull up this huge regulatory, um, wall, you know, it may be the U S that has the fence around at this time. It's going to be really interesting. Copyright's a super fascinating thing. Like, like if the Chinese models don't, um, protect copyright and the U S ones are forced to, what is, The rest of the world do. You know, do we go to the EU and say, you can't use Chinese models. They don't respect copyright. And how will the EU respond? I don't know.

AI assessment note: “what I fear we're going to do is the two leading players will recognize the threat”

Q So, I'm, I'm just curious, how do you manage that? How do you manage being so, you know, trying to be founder friendly, and trying to tell these young people, go for the, the moon, You know, hit the stars while talking to you, Timco about the fact that you're going to fiduciary their capital.

A I think it's really hard. Like, um, I used to use this metaphor, which I don't think makes sense to anybody, but I'll use it anyway. When I was young and I'm almost 60, um, sometimes a friend of yours had a bicycle that, that was a little old and rickety and not all together. And the The handlebars weren't in perfect connection with the front wheel. There was slop in it, and so you, you would, you, you kind of thought you were steering, but you, you just had to oversteer a lot, and you kind of went down the road in a janky way, and it's a lot like that. You don't have the steering wheel, and your ability to influence is limited, um, and so, You do everything you can to earn the respect of the founder, and, and respect is a different word than affection, I think, and it's hard. Like, it's super hard, and the great ones have figured out how to do it. Um, and by the way, it's even harder with sycophants living in the later stage investment rounds, because they come in and say, Everything the founder wants to hear, and that makes it even harder, because here's somebody with a lot of money showing up who's not doing what you're doing, you know, and so it's a craft for sure.

AI assessment note: “You do everything you can to earn the respect of the founder”

Q is a questionable choice of what you are building and how and why, and that product is actually really terrible from a UI perspective, right? So I'd be curious for you, like, In this world, it does seem like you have to really have taste about what you build and why, too. Do you think that's true? And if so, how do you tell if somebody has it or not?

A Yeah, I mean, it may be that both relationships and taste become even more important because of the volume of, of, the volume of information that can be created could create more noise. One thing I would really tell people, and you've probably been down this path yourself, but Like the more you use AI, the more you understand and intuitively have a feel for what it's capable of. And then the more you push it and into places you might not have thought about before. And I'm, I'm surprised. I was surprised yesterday, you know, like, oh, wow. You know, it, it figured that out. And if you're not, once again, if you're not playing with it every day, not only do you not know what it's capable of, but you're not developing your skills. To get it to be as good as it can possibly be for you. Like there is an element, people use the phrase prompt engineering before, but I think it's more than that. I think it's having awareness of when it might help you. And, uh, and knowing you can go to it more often.

AI assessment note: “it may be that both relationships and taste become even more important”