The Exchanges

Q That's pretty good. That's pretty good. Um, well, I want to ask this question. So we went over like, You know, what you look for in investments and all that kind of stuff, but I want to know what informs you, and who is someone that you admire most, and what have you learned from them?

A I think somebody I admire the most is probably, like, Arvind that glean. I'll tell you the reasons I admire him. Number one, I, I think, like, I love, like, I love the Japanese philosophy of, you know, respect your craft. You do work because that's what people do. Um, you don't do work to win. You don't do work to be number one. You don't do work to have a high ego about what you do. Um, and I think in a weird way, amongst people I've worked with, Arvind absolutely embodies that. Um, he told me something which made no sense at the time, and I'm like, of course he would say that, um, to, uh, in the early days, and it stuck with me, and he said, Didi, don't complain about hard work. Hard work is a gift. And if you wake up where you are doing the job that you do, and you can work hard, you don't know how lucky you have it. Most people can't do that. Um, and at the time I'm like, you're the, you're the boss. Of course you would say that. Um, but he also works despite having, you know, a paper net worth of multi billions of dollars. He works more than almost anybody I know at that level. He has no joy in ego stuff, events, podcasts. He hates them. I know he hates them. Like he goes to them because he has to, because he's a CEO in the face of the company. He doesn't like that stuff. He doesn't buy flamboyant things. He drives shitty cars. He lives in a house that, you know, we joke t…

AI assessment note: “I think somebody I admire the most is probably, like, Arvind that glean.”

Q That's pretty good. That's pretty good. Um, well, I want to ask this question. So we went over like, You know, what you look for in investments and all that kind of stuff, but I want to know what informs you, and who is someone that you admire most, and what have you learned from them?

A I think somebody I admire the most is probably, like, Arvind that glean. I'll tell you the reasons I admire him. Number one, I, I think, like, I love, like, I love the Japanese philosophy of, you know, respect your craft. You do work because that's what people do. Um, you don't do work to win. You don't do work to be number one. You don't do work to have a high ego about what you do. Um, and I think in a weird way, amongst people I've worked with, Arvind absolutely embodies that. Um, he told me something which made no sense at the time, and I'm like, of course he would say that, um, to, uh, in the early days, and it stuck with me, and he said, Didi, don't complain about hard work. Hard work is a gift. And if you wake up where you are doing the job that you do, and you can work hard, you don't know how lucky you have it. Most people can't do that. Um, and at the time I'm like, you're the, you're the boss. Of course you would say that. Um, but he also works despite having, you know, a paper net worth of multi billions of dollars. He works more than almost anybody I know at that level. He has no joy in ego stuff, events, podcasts. He hates them. I know he hates them. Like he goes to them because he has to, because he's a CEO in the face of the company. He doesn't like that stuff. He doesn't buy flamboyant things. He drives shitty cars. He lives in a house that, you know, we joke t…

AI assessment note: “somebody I admire the most is probably, like, Arvind that glean.”

Q That's pretty good. That's pretty good. Um, well, I want to ask this question. So we went over like, You know, what you look for in investments and all that kind of stuff, but I want to know what informs you, and who is someone that you admire most, and what have you learned from them?

A I think somebody I admire the most is probably, like, Arvind that glean. I'll tell you the reasons I admire him. Number one, I, I think, like, I love, like, I love the Japanese philosophy of, you know, respect your craft. You do work because that's what people do. Um, you don't do work to win. You don't do work to be number one. You don't do work to have a high ego about what you do. Um, and I think in a weird way, amongst people I've worked with, Arvind absolutely embodies that. Um, he told me something which made no sense at the time, and I'm like, of course he would say that, um, to, uh, in the early days, and it stuck with me, and he said, Didi, don't complain about hard work. Hard work is a gift. And if you wake up where you are doing the job that you do, and you can work hard, you don't know how lucky you have it. Most people can't do that. Um, and at the time I'm like, you're the, you're the boss. Of course you would say that. Um, but he also works despite having, you know, a paper net worth of multi billions of dollars. He works more than almost anybody I know at that level. He has no joy in ego stuff, events, podcasts. He hates them. I know he hates them. Like he goes to them because he has to, because he's a CEO in the face of the company. He doesn't like that stuff. He doesn't buy flamboyant things. He drives shitty cars. He lives in a house that, you know, we joke t…

AI assessment note: “somebody I admire the most is probably, like, Arvind that glean.”

Q and use Brex. Start today at Brex.com slash sorcery. That's B-R-E-X dot com slash sorcery. Most of the ones I see in my feed, because I'm also, like, definitely, like, active on X, but I like a lot of data-driven content. Content is the data-driven content that you put out, whether it's charts or like macro analyses and that kind of thing. So like, what is your thinking behind those?

A I have a 10 Commandments type list of when I started writing on Twitter specifically, I told myself it's so easy to knee-jerk do stuff, right? Like you see, you scroll for a bit, you're like, oh man, this is the thing everyone's talking about. I need to have my opinion. I need to put a take out there. Um, I found that Paradigm to be not evergreen. This is just not a systematic way to do things. So I told myself, okay, what is my thing? And so I have four or five areas of competency. Two, I try to stick to facts and not opinions as often as possible. No political commentary. No, like, you know, try to minimize negativity in any way, um, and, and not offend people for no reason, even though sometimes I clearly missed that. Go. Um, and, and so, you know, things like that. I have a bunch of list of commandments. The reason the data thing always stands out to me is because I'm like, well, it is literally fact.

AI assessment note: “The reason the data thing always stands out to me is because I'm like, well, it is literally fact.”

Q and use Brex. Start today at Brex.com slash sorcery. That's B-R-E-X dot com slash sorcery. Most of the ones I see in my feed, because I'm also, like, definitely, like, active on X, but I like a lot of data-driven content. Content is the data-driven content that you put out, whether it's charts or like macro analyses and that kind of thing. So like, what is your thinking behind those?

A I have a 10 Commandments type list of when I started writing on Twitter specifically, I told myself it's so easy to knee-jerk do stuff, right? Like you see, you scroll for a bit, you're like, oh man, this is the thing everyone's talking about. I need to have my opinion. I need to put a take out there. Um, I found that Paradigm to be not evergreen. This is just not a systematic way to do things. So I told myself, okay, what is my thing? And so I have four or five areas of competency. Two, I try to stick to facts and not opinions as often as possible. No political commentary. No, like, you know, try to minimize negativity in any way, um, and, and not offend people for no reason, even though sometimes I clearly missed that. Go. Um, and, and so, you know, things like that. I have a bunch of list of commandments. The reason the data thing always stands out to me is because I'm like, well, it is literally fact.

AI assessment note: “The reason the data thing always stands out to me is because I'm like, well, it is literally fact.”

Q and use Brex. Start today at Brex.com slash sorcery. That's B-R-E-X dot com slash sorcery. Most of the ones I see in my feed, because I'm also, like, definitely, like, active on X, but I like a lot of data-driven content. Content is the data-driven content that you put out, whether it's charts or like macro analyses and that kind of thing. So like, what is your thinking behind those?

A I have a 10 Commandments type list of when I started writing on Twitter specifically, I told myself it's so easy to knee-jerk do stuff, right? Like you see, you scroll for a bit, you're like, oh man, this is the thing everyone's talking about. I need to have my opinion. I need to put a take out there. Um, I found that Paradigm to be not evergreen. This is just not a systematic way to do things. So I told myself, okay, what is my thing? And so I have four or five areas of competency. Two, I try to stick to facts and not opinions as often as possible. No political commentary. No, like, you know, try to minimize negativity in any way, um, and, and not offend people for no reason, even though sometimes I clearly missed that. Go. Um, and, and so, you know, things like that. I have a bunch of list of commandments. The reason the data thing always stands out to me is because I'm like, well, it is literally fact.

AI assessment note: “reason the data thing always stands out to me is because I'm like, well, it is literally fact”

Q I want to get into areas, but I want to, I want to understand that a little bit more. So what do you, how do you pressure test those types of founders? What are the traits you're looking for other than like really wants to build a company?

A One thing I can easily say that we're not looking for is It is very hard for us to get to conviction on a founder or a company when we haven't known them for a while. Um, I think, you know, personality, like, like with, you know, VCs love using the word shotgun wedding. But it kind of does matter. Like you just can't trust the nature of a founder when they're like pitching to you right before a raise. That's a really hard, like they're selling to you, right? Like it's really hard to, to, to get, to get through that. People can be great salespeople. What I really care, and I can't speak for the firm. I can say most of Menlo operates this way. Um, but for me especially is I'm looking to build that relationship way before you're, you're raising. And I want to understand, like, what makes you tick? And half the time I'm not talking about work. I mean, work we have to sometimes talk about because it's weird otherwise. Like, why is this VC, like, talking to me about my personal life? Um, but I kind of just want to understand, like, what makes you tick? What are your motivations? How did you grow up? Like, what drives you? And that gives me at least a lot of confidence on, like, whether or not you would be, you know, long-term successful.

AI assessment note: “I kind of just want to understand, like, what makes you tick? What are your motivations?”

Q I want to get into areas, but I want to, I want to understand that a little bit more. So what do you, how do you pressure test those types of founders? What are the traits you're looking for other than like really wants to build a company?

A One thing I can easily say that we're not looking for is It is very hard for us to get to conviction on a founder or a company when we haven't known them for a while. Um, I think, you know, personality, like, like with, you know, VCs love using the word shotgun wedding. But it kind of does matter. Like you just can't trust the nature of a founder when they're like pitching to you right before a raise. That's a really hard, like they're selling to you, right? Like it's really hard to, to, to get, to get through that. People can be great salespeople. What I really care, and I can't speak for the firm. I can say most of Menlo operates this way. Um, but for me especially is I'm looking to build that relationship way before you're, you're raising. And I want to understand, like, what makes you tick? And half the time I'm not talking about work. I mean, work we have to sometimes talk about because it's weird otherwise. Like, why is this VC, like, talking to me about my personal life? Um, but I kind of just want to understand, like, what makes you tick? What are your motivations? How did you grow up? Like, what drives you? And that gives me at least a lot of confidence on, like, whether or not you would be, you know, long-term successful.

AI assessment note: “I'm looking to build that relationship way before you're, you're raising.”

Q I want to get into areas, but I want to, I want to understand that a little bit more. So what do you, how do you pressure test those types of founders? What are the traits you're looking for other than like really wants to build a company?

A One thing I can easily say that we're not looking for is It is very hard for us to get to conviction on a founder or a company when we haven't known them for a while. Um, I think, you know, personality, like, like with, you know, VCs love using the word shotgun wedding. But it kind of does matter. Like you just can't trust the nature of a founder when they're like pitching to you right before a raise. That's a really hard, like they're selling to you, right? Like it's really hard to, to, to get, to get through that. People can be great salespeople. What I really care, and I can't speak for the firm. I can say most of Menlo operates this way. Um, but for me especially is I'm looking to build that relationship way before you're, you're raising. And I want to understand, like, what makes you tick? And half the time I'm not talking about work. I mean, work we have to sometimes talk about because it's weird otherwise. Like, why is this VC, like, talking to me about my personal life? Um, but I kind of just want to understand, like, what makes you tick? What are your motivations? How did you grow up? Like, what drives you? And that gives me at least a lot of confidence on, like, whether or not you would be, you know, long-term successful.

AI assessment note: “I want to understand, like, what makes you tick? What are your motivations?”

Q And then on areas, what are the areas you focus on?

A I'll say one last thing for area. So one last thing I think that is important is there are a bunch of founders that even meet that bucket. I think the biggest bottleneck today is ability to hire. Um, so I think number one reason is there are plenty of really smart people who also care about something very deeply. And then, I mean, the unfortunate truth is I look at them, I'm like, but man, who would work for you? Like, I just don't see you being able to tap into a network. Or even be, like, super convincing when it comes to candidates and get people to buy into this mission. You almost kind of need to be a little bit of a cult leader as a, as a founder. And not everyone is capable of being cult leader. Um, people who do it well can hire well and retain well. So that's the second thing on the founder side. On the area side, um, look, one of the things I mentioned before is how can we apply All of these novel technologies to, um, the industries that need it the most. Um, the industries that no one talks about. The industries that are super, super boring. The industries where, like, there is information asymmetry between what most people in AI know, like the Venn diagram of things people in AI know and care about, and read Twitter about, and things the world really, like, like matters in the world. And who is at the very edge of the little tiny intersection between that? Where the…

AI assessment note: “On the area side, um, look, one of the things I mentioned before”

Q What's your, like, what's your, um, investment range? Like, do you have parameters around check size, valuations? How do you think about that?

A I would say all parameters are guidance and they're rough. Um, at the same time, even despite those rough parameters, it's so hard to justify a billion. I just don't see how people can write a billion dollar seed. Unless, um, and here's another hot take. Unless like, you know, it's one of those situations where the money's not coming from the fund, right? It's one of those SPVs type structures where it's like, okay, I'm kind of going to put in one million of a hundred million round and raise ninety nine million from other people. Um, and, uh, I'll put my name on it, but I'm effectively taking none of the risk here. Um, I'm just getting all the marketing value of being, you know, the big, bold VC who's backing these egregiously long-term bets. So that happens. Um, but aside from that, I don't know how you could justify putting it out of your own fund. It doesn't make that much sense. I would, I don't want to put a hard number on the seed that we'd go up to because, you know, sometimes we break that. Sometimes we do exceptional stuff, but definitely not a billion, you know, like even a hundred million seed. Yeah, I can see that. I can see that in some cases. Um, so that's, that's how I would put it.

AI assessment note: “I don't want to put a hard number on the seed that we'd go up to”

Q And then on areas, what are the areas you focus on?

A I'll say one last thing for area. So one last thing I think that is important is there are a bunch of founders that even meet that bucket. I think the biggest bottleneck today is ability to hire. Um, so I think number one reason is there are plenty of really smart people who also care about something very deeply. And then, I mean, the unfortunate truth is I look at them, I'm like, but man, who would work for you? Like, I just don't see you being able to tap into a network. Or even be, like, super convincing when it comes to candidates and get people to buy into this mission. You almost kind of need to be a little bit of a cult leader as a, as a founder. And not everyone is capable of being cult leader. Um, people who do it well can hire well and retain well. So that's the second thing on the founder side. On the area side, um, look, one of the things I mentioned before is how can we apply All of these novel technologies to, um, the industries that need it the most. Um, the industries that no one talks about. The industries that are super, super boring. The industries where, like, there is information asymmetry between what most people in AI know, like the Venn diagram of things people in AI know and care about, and read Twitter about, and things the world really, like, like matters in the world. And who is at the very edge of the little tiny intersection between that? Where the…

AI assessment note: “On the area side, um, look, one of the things I mentioned before is”

Q good point. Like, so Carta put out a recent report that Series A's that are AI, um, enabled, or AI in their name, are getting a 30% premium. I can't wait until the next report comes out to see where that, like, the delta is, or, like, how much it's changed. But if everybody, if every company is AI, how, how are we measuring this? Every company's AI. Should be.

A Well, I think the stat that he said was what, 30% premium, right? You said 30% premium. I'll tell you that maybe I take 10 to 20 pitches every week, and in the last year, I have seen, like, the ups and downs of different buzzwords go in and out of flat fashion in a way which is hilarious. There was one time where every company was like, well, our differentiator is that we get data, and then data flywheel feeds back into fine-tuning, and that's why we're different. Same guys, one year later, yeah, yeah, that same thing, but instead of fine-tuning, it's RL. And I'm like, what do you know about RO? Tell me a little bit about it. And silence. You know, it's reinforcement learning. You know, reinforcement learning?

AI assessment note: “I have seen, like, the ups and downs of different buzzwords go in and out”

Q good point. Like, so Carta put out a recent report that Series A's that are AI, um, enabled, or AI in their name, are getting a 30% premium. I can't wait until the next report comes out to see where that, like, the delta is, or, like, how much it's changed. But if everybody, if every company is AI, how, how are we measuring this? Every company's AI. Should be.

A Well, I think the stat that he said was what, 30% premium, right? You said 30% premium. I'll tell you that maybe I take 10 to 20 pitches every week, and in the last year, I have seen, like, the ups and downs of different buzzwords go in and out of flat fashion in a way which is hilarious. There was one time where every company was like, well, our differentiator is that we get data, and then data flywheel feeds back into fine-tuning, and that's why we're different. Same guys, one year later, yeah, yeah, that same thing, but instead of fine-tuning, it's RL. And I'm like, what do you know about RO? Tell me a little bit about it. And silence. You know, it's reinforcement learning. You know, reinforcement learning?

AI assessment note: “I have seen, like, the ups and downs of different buzzwords go in and out”

Q And then on areas, what are the areas you focus on?

A I'll say one last thing for area. So one last thing I think that is important is there are a bunch of founders that even meet that bucket. I think the biggest bottleneck today is ability to hire. Um, so I think number one reason is there are plenty of really smart people who also care about something very deeply. And then, I mean, the unfortunate truth is I look at them, I'm like, but man, who would work for you? Like, I just don't see you being able to tap into a network. Or even be, like, super convincing when it comes to candidates and get people to buy into this mission. You almost kind of need to be a little bit of a cult leader as a, as a founder. And not everyone is capable of being cult leader. Um, people who do it well can hire well and retain well. So that's the second thing on the founder side. On the area side, um, look, one of the things I mentioned before is how can we apply All of these novel technologies to, um, the industries that need it the most. Um, the industries that no one talks about. The industries that are super, super boring. The industries where, like, there is information asymmetry between what most people in AI know, like the Venn diagram of things people in AI know and care about, and read Twitter about, and things the world really, like, like matters in the world. And who is at the very edge of the little tiny intersection between that? Where the…

AI assessment note: “apply All of these novel technologies to, um, the industries that need it the most.”

Q good point. Like, so Carta put out a recent report that Series A's that are AI, um, enabled, or AI in their name, are getting a 30% premium. I can't wait until the next report comes out to see where that, like, the delta is, or, like, how much it's changed. But if everybody, if every company is AI, how, how are we measuring this? Every company's AI. Should be.

A Well, I think the stat that he said was what, 30% premium, right? You said 30% premium. I'll tell you that maybe I take 10 to 20 pitches every week, and in the last year, I have seen, like, the ups and downs of different buzzwords go in and out of flat fashion in a way which is hilarious. There was one time where every company was like, well, our differentiator is that we get data, and then data flywheel feeds back into fine-tuning, and that's why we're different. Same guys, one year later, yeah, yeah, that same thing, but instead of fine-tuning, it's RL. And I'm like, what do you know about RO? Tell me a little bit about it. And silence. You know, it's reinforcement learning. You know, reinforcement learning?

AI assessment note: “I have seen, like, the ups and downs of different buzzwords go in and out”

Q What's your, like, what's your, um, investment range? Like, do you have parameters around check size, valuations? How do you think about that?

A I would say all parameters are guidance and they're rough. Um, at the same time, even despite those rough parameters, it's so hard to justify a billion. I just don't see how people can write a billion dollar seed. Unless, um, and here's another hot take. Unless like, you know, it's one of those situations where the money's not coming from the fund, right? It's one of those SPVs type structures where it's like, okay, I'm kind of going to put in one million of a hundred million round and raise ninety nine million from other people. Um, and, uh, I'll put my name on it, but I'm effectively taking none of the risk here. Um, I'm just getting all the marketing value of being, you know, the big, bold VC who's backing these egregiously long-term bets. So that happens. Um, but aside from that, I don't know how you could justify putting it out of your own fund. It doesn't make that much sense. I would, I don't want to put a hard number on the seed that we'd go up to because, you know, sometimes we break that. Sometimes we do exceptional stuff, but definitely not a billion, you know, like even a hundred million seed. Yeah, I can see that. I can see that in some cases. Um, so that's, that's how I would put it.

AI assessment note: “I don't want to put a hard number on the seed that we'd go up to”

Q What's your, like, what's your, um, investment range? Like, do you have parameters around check size, valuations? How do you think about that?

A I would say all parameters are guidance and they're rough. Um, at the same time, even despite those rough parameters, it's so hard to justify a billion. I just don't see how people can write a billion dollar seed. Unless, um, and here's another hot take. Unless like, you know, it's one of those situations where the money's not coming from the fund, right? It's one of those SPVs type structures where it's like, okay, I'm kind of going to put in one million of a hundred million round and raise ninety nine million from other people. Um, and, uh, I'll put my name on it, but I'm effectively taking none of the risk here. Um, I'm just getting all the marketing value of being, you know, the big, bold VC who's backing these egregiously long-term bets. So that happens. Um, but aside from that, I don't know how you could justify putting it out of your own fund. It doesn't make that much sense. I would, I don't want to put a hard number on the seed that we'd go up to because, you know, sometimes we break that. Sometimes we do exceptional stuff, but definitely not a billion, you know, like even a hundred million seed. Yeah, I can see that. I can see that in some cases. Um, so that's, that's how I would put it.

AI assessment note: “I don't want to put a hard number on the seed that we'd go up to”