The Exchanges

Q very worried now that, like, normal life, girlfriends, kids, just the wonderful things that happen in life will make me mediocre, because actually, I I'm grinding all weekend, and when I see other GPs on Instagram skiing, I'm like, ha, I'm working, and you're skiing. Do you worry that with normality and wife and child, which is wonderful, but you, you lose the work, and you become more mediocre, respectfully?

A You know, I think the one thing I really changed my mind on from my days in private equity to now is Has been how I define hard work. Um, like I used to think of hard work in a very absolute sense where it meant I had to be working a hundred hours a week. I had to be waking up at three 45, showing up to the office at six 30, the last one in the office, um, you know, sleeping four hours a night, like sleep when I'm dead type guy. That was me. Um, and I learned that from baseball and that was like how I got through and survived actually baseball wise. Um, but I've changed my mind on that because now I really do believe that As a creative, um, which is at the core, a lot of what you and I do, you have to, um, take care of your full self in order to optimize creative work. And if you're trying to do inspired creative work, which investing is creative work, by the way, you need to think creatively around things and around ideas and support people. Um, you have to be able to take care of your full self. And for me personally, part of taking care of my full self is being able to go for a walk with my wife in the morning and, you know, spend time with my child, you know, coach my child's little league team someday. Um, I think that is part of taking care of my full self in a way that I didn't agree that it was before.

AI assessment note: “you have to, um, take care of your full self in order to optimize creative work”

Q If it doesn't hit, and you see it doesn't hit, me and you are both smart and analytical when it comes to Twitter, like, if you see it doesn't hit, do you take it down? I do. I have my rule of, like, seven likes within the first minute, minimum.

A Seven likes within the first minute. Mine would be like seven likes within the first second. No, no, no. Uh, just kidding. Just kidding, Harry. Uh, no, I, um, I never delete threads. Uh, the, the one exception to that would be if like, if I thought I didn't think something through comprehensively, and somebody calls me out on it, and, and they're right. Then I would say like, okay, I actually don't think there's a benefit to having something out there that I didn't think through well enough, but normally I will make sure that I'm going to be really proud of posting something before I post it. Individual tweets now and then I'll delete if I just don't think it's like hitting or if it's particularly interesting to be out there. Um, but with threads, I don't know that I've ever, ever deleted a thread. Julian, our friend deletes threads all the time. Like I've seen him delete things that have 20,000 likes. Because he doesn't like, you know, two or three responses that he gets to it, which I think is, like, insane, but he's done that.

AI assessment note: “no, I, um, I never delete threads.”

Q What do you think makes a great one versus not a great one, and do you know when one's gonna hit before?

A Yeah, I think there are certain topics that it's clear that, you know, will resonate with large amounts of people. Um, there have been a couple that I would say have surprised me, but for the most part, I know whether a topic has like broad resonance or whether it's more of a niche. Um, in terms of what makes a great one, I think it's, it depends on what you define as great, right? Like I've put out things that I thought were exceptional that had a tiny, you know, potential audience and didn't go anywhere, but I thought they were really well written and well researched. And then I've put out things that I thought were like kind of fortune cookie and broad, but people like that. And, you know, maybe they, maybe it resonated with them because it connected with them on some emotional level, which I also think is great. Um, so it just depends. I, you know, it depends on, on, um, you know, on the situation, on how I'm feeling. Sometimes I like writing things about broad life principles because it helps me clarify my own thinking on those topics, or if I've been feeling down or up and I'm trying to kind of like change my own mood. Writing is my process for doing that. I just happen to share that writing publicly after doing it.

AI assessment note: “for the most part, I know whether a topic has like broad resonance”

Q Sahil, tell me, I, I know you a little bit. I don't buy that you want to stay small and play your collaborative game. You're going to want to go bigger, and you're going to want to write bigger checks and lead rounds. I know you. You're like me. That's why we get on. Um, like, what is the actual plans?

A I'm going to stay small, and I'm going to continue to write small checks. Um, closely held plans, man. I, um, I don't have some grand strategy right now, to be totally honest. I, um, I'm a, I like to push. I, I, that's my wiring. With everything that I do, I like to put my head down, I like to push, and that's how I'm always going to be. I don't necessarily think that that means going bigger. I, I personally think of what's, you know, what's kind of being built right now is like, I don't know, like a less quirky Tim Ferriss with an investment fund is like what I'm kind of going for as, as a vibe, and I think, um, you know, that doesn't necessarily require me raising bigger and bigger funds. Um, there's plenty of ways to make money that I think don't involve going out and raising fifty million dollars. Um, what I ultimately want to do is drive exceptional returns for my investors, and I want to invest in the best companies in the world, and I want to be a part of, uh, putting capital behind companies that change the world. And hopefully change the world for the better. And I think that as a capital allocator, that's an amazing goal and an amazing vision. Does that mean I'm going to go out and raise, you know, 50, a hundred million dollar funds? I don't know. I would, I'd be surprised if I did, but you never know.

AI assessment note: “I'm going to stay small, and I'm going to continue to write small checks.”

Q No, I, I, I totally agree. How do you think about managing founder, sorry, I'm kind of using this as an advice session. How do you think about managing founder expectations? Because both of us have these big microphones. How do you think about managing founder expectations when it comes to what you are and aren't willing to distribute and promote?

A Yeah, it's a great question. I got that, I got asked that by a lot of the, the thoughtful LPs, um, you know, that I had discussions with was like, You know, if you invest in 50 companies, are they all going to be hitting you up? Are you just going to be having to tweet about the companies all the time? I think it tends to be, um, 80, 20 in terms of, like, you know, very few of the companies will actually take you up on all of the different things you can do for them. And if you're able to deliver something comprehensive to a handful that is really valuable for them, and then for the rest, it's kind of fundraising announcements or like big feature announcements or big things that happen and you're amplifying those stories, it ends up working out where you're not spending all of your time just sitting around kind of tweeting or newslettering or podcasting about these, about these different companies. But I think the big inflection points tend to be around big announcements, right? Like The other day, there was an example. Um, one of the companies, one of the first investments out of the fund is this business wander. Um, QED and red point were leading the series a very cool short-term rental vertically integrated, um, platform. And I did this video to announce it. Paki and I were kind of both doing like an announcement for, for the investment in the, uh, in the company and Paki di…

AI assessment note: “very few of the companies will actually take you up on all of the different things”

Q No, I, I, I totally agree. How do you think about managing founder, sorry, I'm kind of using this as an advice session. How do you think about managing founder expectations? Because both of us have these big microphones. How do you think about managing founder expectations when it comes to what you are and aren't willing to distribute and promote?

A Yeah, it's a great question. I got that, I got asked that by a lot of the, the thoughtful LPs, um, you know, that I had discussions with was like, You know, if you invest in 50 companies, are they all going to be hitting you up? Are you just going to be having to tweet about the companies all the time? I think it tends to be, um, 80, 20 in terms of, like, you know, very few of the companies will actually take you up on all of the different things you can do for them. And if you're able to deliver something comprehensive to a handful that is really valuable for them, and then for the rest, it's kind of fundraising announcements or like big feature announcements or big things that happen and you're amplifying those stories, it ends up working out where you're not spending all of your time just sitting around kind of tweeting or newslettering or podcasting about these, about these different companies. But I think the big inflection points tend to be around big announcements, right? Like The other day, there was an example. Um, one of the companies, one of the first investments out of the fund is this business wander. Um, QED and red point were leading the series a very cool short-term rental vertically integrated, um, platform. And I did this video to announce it. Paki and I were kind of both doing like an announcement for, for the investment in the, uh, in the company and Paki di…

AI assessment note: “it tends to be, um, 80, 20 in terms of, like, you know”