The Exchanges

Q should do the same thing. Um, uh, and then I realized I can't be arsed. Um, uh, but, uh, I, I do want to ask, you know, it takes me to something that you said before, which is the traditional VC model is dead slash dying, just to put the caveat of slash dying. Um, why are the traditional middle tier VCs going to get their lunch eaten, my friend?

A Yeah, I think what you're seeing is a barbell that is form, formed or forming within the VC landscape, and on one end, you have the Sequoias, Benchmarks, Andreessen's, you know, they're like, And even Tiger, I think now, KOTU, who have developed this name brand, and this cachet, and this real winning edge that I think exists around that, and continues to be self, you know, self-fulfilling, and self-perpetuating, where when they come into a round, everyone's like, oh shit, I'm not going to invest in the competitor, uh, the competitors all get scared, there's a ton of money behind one player, etc. That will continue to exist, I believe. Um, and then on the other end of this barbell, I think you have people like us, um, people like Josh Buckley, people like us, people like Paki, um, like Shrug, people who have some very clear value lever that they can deliver to companies with, and in your case now you're big, but with smaller checks. Now you're kind of pushing towards this other end of the spectrum. That's a whole different story. Um, where you're going to become one of those guys on the other end of the barbell. So kudos to you. I'm going to stay over on the other end where you can get into any deal and you can drive material value with some specific lever, whether it's like a fund that gets raised because they're amazing performance marketing guy, like Nick Sharma with Sharma b…

AI assessment note: “Those are the two ends of the spectrum that I think work.”

Q Do you ever get down from the responses? When someone responds negatively to mine, even though I don't know them, I've never met them before, it does impact me, actually. I get a little bit hurt.

A Yeah. Negativity bias is a real thing. I don't know if that's the right term for it. It's what I call it, which is, you know, I can post a thread and And I'll be looking through the responses and there'll be a hundred positive responses. And then one guy says something negative. Some anonymous account says something really mean or negative. And that's the only thing you can think about. And suddenly you're like down and you're feeling it. Um, so yeah, absolutely. I mean, all the time I've posted things that I thought were really thoughtful. I, you know, I posted this thing. This is a good example of it. When, when I found out I was going to be a dad, um, I was feeling very introspective as a result of that. And, you know, my whole life changed in an instant knowing that. And, um, I wrote this thread about, like, principles that I wanted to kind of teach my child to live by, and it was really just my process of being introspective around the type of father I want to be, the type of child I want to raise, and, um, I got, like, an amazing response. Tons of people shared it. It was incredible, but there was, like, a, you know, maybe two, three percent of people that really took offense to me, um, thinking I could, like, mold my child, and I don't know why, honestly. It was just, it was in good Nate, it was good natured, but they were really angry about it, and I got a bunch of angr…

AI assessment note: “so yeah, absolutely. I mean, all the time”

Q I mean, God, I love the transition of this conversation. Final one for the quick fire. Yeah, obviously so exciting with the newborn. Um, in terms of like three traits that you'd most like your child to adopt, what three traits would they be?

A I want them to be interested. That's probably my number one trait that I look for in people in general. Someone that is interested, um, that is kind of curious, that is going down, you know, rabbit holes, wanting to learn about the world around them. Um, I want them to be Um, a, I call it a darkest hour friend. The type of friend who is there for you when shit is really bad. We all have friends who are there for us to celebrate. Like, oh, you launched a fund, everyone wants to be there, and cheers, and it's great, and it's fun, a birthday party, whatever. Um, but what friends are there when that fund collapses? Like, what friends are there when you lose all your money? Um, when things really hit the fan? Those are the friends that really count. I want my, my son to be that type of friend to people. Um, And then I think the third one is just to be kind. Be a kind person. Um, I, there's so many people out there that are just kind of assholes, and it's so short-sighted, and it's just not a fun way to live. It's just not a fun energy to give out to the world, and so I really want my son to be a kind human being. I don't think I was a kind human being all my life, and I really regret it. Um, what do you think made you change? I think that that really matters.

AI assessment note: “I want them to be interested... darkest hour friend... third one is just to be kind.”

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: “Individual tweets now and then I'll delete if I just don't think it's like hitting”

Q Man, I'm so thrilled that you're doing it here. Really, honestly, it means a lot to me. Can I ask, how did you come up with the fund size? Why did you choose tan? And how are you thinking through portfolio construction, check size, deployment? What are the thoughts there?

A Yeah, so I originally thought I would raise five. Um, part of that was my own, you know how this works, like my own imposter syndrome, self-limiting, um, mindset around these things where I was like, shit, no one's going to give me more than, you know, a few million bucks. And if I'm going to go out, try to raise five, but if I can only raise two, that's okay. And I'll just do that. And, um, I think it was like in two days, it was over five, and, um, basically then what happened was I realized that if I had over 99 LPs, I had to keep it under 10 legally, um, and I offered it to a bunch of my friends and family, because I, I'm a huge believer in, like, bringing people along for the ride, and a lot of my friends wanted to learn more about the things I was doing so quickly, the LP base grew past 99, and I had to keep it under 10, so then that was, like, the actual limiting cap on, uh, on going out and doing it. In terms of fund construction, um, it's going to be largely stage agnostic, um, but it'll probably concentrate around pre-seed, seed stuff. In this environment, you know, if there are slam dunk, you and I have talked about this, if there are slam dunk risk-adjusted opportunities that are Series B, I'm not going to pass up an opportunity to go and participate in something like that. It'll just have to be, you know, a bigger allocation, bigger check size into things like that…

AI assessment note: “the LP base grew past 99, and I had to keep it under 10”

Q How do you think the biggest challenge, which often is the case for, you know, a lot of the micro funds, which is kind of bucketed into kind of the angel world, and actually not really angels, and the 25 K checks are hard to make work, how are you thinking on the discipline you'll have around check size, and like, will you do 25 and 50 K checks?

A 50 will be the smallest I would do. Um, I, you know, I think everything will probably fall into the 50 to two 50 range, um, with, you know, two 50 coming at probably like series B type rounds and smaller checks into earlier higher risk things. Um, but I think 50 will end up being the smallest that I will do. The benefit of being small, which you and I have also talked about, is that it's not hard to get into a deal with a small check. If you can show some amount of value, then the trade for the founder is for this tiny amount of dilution. Is this person going to deliver that value for me? And with what we have with a platform and the ability to go use this megaphone for these companies, that's a very easy trade to make at a 100,000 or at a 200,000 allocation. It might be a very different trade at a million dollar allocation or a 500,000 dollar allocation, which is part of the reason that I think being small for me with an initial fund is actually an advantage to getting into the best things.

AI assessment note: “50 will be the smallest I would do.”

Q should do the same thing. Um, uh, and then I realized I can't be arsed. Um, uh, but, uh, I, I do want to ask, you know, it takes me to something that you said before, which is the traditional VC model is dead slash dying, just to put the caveat of slash dying. Um, why are the traditional middle tier VCs going to get their lunch eaten, my friend?

A Yeah, I think what you're seeing is a barbell that is form, formed or forming within the VC landscape, and on one end, you have the Sequoias, Benchmarks, Andreessen's, you know, they're like, And even Tiger, I think now, KOTU, who have developed this name brand, and this cachet, and this real winning edge that I think exists around that, and continues to be self, you know, self-fulfilling, and self-perpetuating, where when they come into a round, everyone's like, oh shit, I'm not going to invest in the competitor, uh, the competitors all get scared, there's a ton of money behind one player, etc. That will continue to exist, I believe. Um, and then on the other end of this barbell, I think you have people like us, um, people like Josh Buckley, people like us, people like Paki, um, like Shrug, people who have some very clear value lever that they can deliver to companies with, and in your case now you're big, but with smaller checks. Now you're kind of pushing towards this other end of the spectrum. That's a whole different story. Um, where you're going to become one of those guys on the other end of the barbell. So kudos to you. I'm going to stay over on the other end where you can get into any deal and you can drive material value with some specific lever, whether it's like a fund that gets raised because they're amazing performance marketing guy, like Nick Sharma with Sharma b…

AI assessment note: “I think what you're seeing is a barbell that is form, formed or forming”

Q is a lot of firms suddenly having this awakening to the power of content, and hiring their heads of content, and really kind of digging in on what we do, and I, I always kind of shake my head, I think, what are you doing? Um, how do you feel when you see this kind of awakening of venture firms to the power of content, and their resources behind it?

A Well, I think it's interesting because we didn't build, we didn't build this audience. Like I never built an audience as a venture investor, right? My audience is not a bunch of other venture capital firms or venture associates. My audience is a bunch of real people that are looking to learn, grow, explore things, et cetera. Um, and in my opinion, that's much more powerful because that audience is real customers of whatever it is that these companies that I'm investing in are selling versus venture firms who, you know, their associates are told, Hey, go out and build an audience. And their audience ends up being a bunch of other venture associates who are all liking each other's things and sharing it. And that's, that's tough, right? Cause then they're, you're tweeting something out and you're sharing about a company and the only people that are seeing it are a bunch of other people within your little ecosystem. Um, Um, so I think they are going to run into challenges around that, and it's going to, it's going to require real defining for them to figure out what is our, you know, core value proposition of this content. Is it just so that we can tell our founders that we have, you know, a content arm and we're sharing, or is there a real reason for being, um, you know, real insights that are being driven through it? I think Andreessen is probably the best example of a firm who h…

AI assessment note: “it's going to be hard for a lot of these guys to do it”

Q in the mouth. Happy Monday! Uh, uh, listen, I, I want to ask, you know, I think, you know, um, luck plays an important role in a lot of journeys, but then also not as important as some people suggest. Can I ask, you said before that luck is misunderstood and can be engineered of sorts. How do you think about this? And I guess, can you provide some examples?

A Yeah. I always had this concept. I think I first read it from Tim Brown, who was the CEO of IDEO at the time, um, of like engineered serendipity that you can kind of engineer your own luck. Um, and I've thought about it a lot and I'm actually working on a piece I'm going to write about kind of how to get lucky, but. I think in general, luck is misunderstood in that a lot of what we perceive as luck is just the macro result of thousands of micro actions. And what I mean by that is you're doing something consistently that led to you getting lucky. And then you say, oh, I got lucky. This thing happened. This break went my way, but really it was that you were doing something that led to that situation. An example of that in my own life, um, Is I used to get up super early to go to the gym. When I first started my career, uh, I wanted to be in the office by 6:30 a.m., be at my desk first, because for some reason in my mind that mattered. I think it's kind of stupid in hindsight, but that mattered to me, and so I'd get up at three 45, I'd do some work, I'd get to the gym at five a.m. on the dot, and I'd work out every single morning, five days a week, and At that time, this is at Equinox in Palo Alto, um, where I was, where I was working out, um, there was maybe five or six people that would show up, like, that were crazy enough to show up at the gym every morning at that time. At th…

AI assessment note: “what we perceive as luck is just the macro result of thousands of micro actions.”

Q Do you ever get down from the responses? When someone responds negatively to mine, even though I don't know them, I've never met them before, it does impact me, actually. I get a little bit hurt.

A Yeah. Negativity bias is a real thing. I don't know if that's the right term for it. It's what I call it, which is, you know, I can post a thread and And I'll be looking through the responses and there'll be a hundred positive responses. And then one guy says something negative. Some anonymous account says something really mean or negative. And that's the only thing you can think about. And suddenly you're like down and you're feeling it. Um, so yeah, absolutely. I mean, all the time I've posted things that I thought were really thoughtful. I, you know, I posted this thing. This is a good example of it. When, when I found out I was going to be a dad, um, I was feeling very introspective as a result of that. And, you know, my whole life changed in an instant knowing that. And, um, I wrote this thread about, like, principles that I wanted to kind of teach my child to live by, and it was really just my process of being introspective around the type of father I want to be, the type of child I want to raise, and, um, I got, like, an amazing response. Tons of people shared it. It was incredible, but there was, like, a, you know, maybe two, three percent of people that really took offense to me, um, thinking I could, like, mold my child, and I don't know why, honestly. It was just, it was in good Nate, it was good natured, but they were really angry about it, and I got a bunch of angr…

AI assessment note: “so yeah, absolutely. I mean, all the time”

Q Oh man, I love it. Normally it's such a formal intro. That was a very casual one. But I want to start with, really, like, in 2018, you didn't have Twitter. You only started in 2019. So, you know, respectfully, who the hell are you, and where did you come from?

A Ask myself that a lot, actually, by the way, and it's actually twenty-twenty. I didn't start sharing things on Twitter until May of twenty-twenty. I had like a few hundred followers at the time, and it was basically just COVID had happened. I mean, I, I grew up on the East Coast, ended up out in California, played baseball. You can, like, see that on my Twitter profile now. I gave up a grand slam on national television. Um, I went into finance. I took a job at a private equity fund. I was, like, doing the very traditional path Um, in mainstream finance where I was doing like LBOs and doing the whole dance around that. But I always knew that I really wanted to work on early stage growth stuff. I wanted to think about the future rather than thinking about the past. And so I, um, I just didn't know what that transition was going to be, right? Like you're kind of on this momentum building path within finance and I didn't know what it was going to be. COVID hit. All of a sudden I wasn't working 9000 hours a week. I wasn't traveling four days a week like I was before. And that was kind of my jumping off point to go try something new. And what it ended up being was building, right? I was writing around all of these topics.

AI assessment note: “grew up on the East Coast, ended up out in California... went into finance”

Q How do you think the biggest challenge, which often is the case for, you know, a lot of the micro funds, which is kind of bucketed into kind of the angel world, and actually not really angels, and the 25 K checks are hard to make work, how are you thinking on the discipline you'll have around check size, and like, will you do 25 and 50 K checks?

A 50 will be the smallest I would do. Um, I, you know, I think everything will probably fall into the 50 to two 50 range, um, with, you know, two 50 coming at probably like series B type rounds and smaller checks into earlier higher risk things. Um, but I think 50 will end up being the smallest that I will do. The benefit of being small, which you and I have also talked about, is that it's not hard to get into a deal with a small check. If you can show some amount of value, then the trade for the founder is for this tiny amount of dilution. Is this person going to deliver that value for me? And with what we have with a platform and the ability to go use this megaphone for these companies, that's a very easy trade to make at a 100,000 or at a 200,000 allocation. It might be a very different trade at a million dollar allocation or a 500,000 dollar allocation, which is part of the reason that I think being small for me with an initial fund is actually an advantage to getting into the best things.

AI assessment note: “50 will be the smallest I would do.”

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 in the mouth. Happy Monday! Uh, uh, listen, I, I want to ask, you know, I think, you know, um, luck plays an important role in a lot of journeys, but then also not as important as some people suggest. Can I ask, you said before that luck is misunderstood and can be engineered of sorts. How do you think about this? And I guess, can you provide some examples?

A Yeah. I always had this concept. I think I first read it from Tim Brown, who was the CEO of IDEO at the time, um, of like engineered serendipity that you can kind of engineer your own luck. Um, and I've thought about it a lot and I'm actually working on a piece I'm going to write about kind of how to get lucky, but. I think in general, luck is misunderstood in that a lot of what we perceive as luck is just the macro result of thousands of micro actions. And what I mean by that is you're doing something consistently that led to you getting lucky. And then you say, oh, I got lucky. This thing happened. This break went my way, but really it was that you were doing something that led to that situation. An example of that in my own life, um, Is I used to get up super early to go to the gym. When I first started my career, uh, I wanted to be in the office by 6:30 a.m., be at my desk first, because for some reason in my mind that mattered. I think it's kind of stupid in hindsight, but that mattered to me, and so I'd get up at three 45, I'd do some work, I'd get to the gym at five a.m. on the dot, and I'd work out every single morning, five days a week, and At that time, this is at Equinox in Palo Alto, um, where I was, where I was working out, um, there was maybe five or six people that would show up, like, that were crazy enough to show up at the gym every morning at that time. At th…

AI assessment note: “luck is misunderstood in that a lot of what we perceive as luck is just the macro result”

Q How did you deal with that, fuck, you're not the best, and you're not actually number one anymore?

A I remember having a conversation with my dad. I called him and I was really upset thinking about academically, athletically. Um, and he just said, um, he said something to the effect of like, remember who you are and remember what you are great at, which is being consistent. Um, and I had never really thought of consistency as something that was my, a trait or something that I kind of held deeply. Um, But I guess it was. And so I realized that that was how I was going to win and outperform at anything I did was just by continuing to show up and just being relentless. Um, And that, that was when it kind of flipped for me. I was like, I'm never going to be the most talented. I'm never going to be the smartest. I'm never going to be the hottest. I'm never going to be the most, um, talented on the baseball field, whatever it was, but I'm just going to keep showing up. And it's really hard to keep someone down if they keep showing up. Really, really, really hard. Um, and so that was when it clipped, clipped for me personally.

AI assessment note: “that was how I was going to win and outperform at anything I did”

Q Man, I'm so thrilled that you're doing it here. Really, honestly, it means a lot to me. Can I ask, how did you come up with the fund size? Why did you choose tan? And how are you thinking through portfolio construction, check size, deployment? What are the thoughts there?

A Yeah, so I originally thought I would raise five. Um, part of that was my own, you know how this works, like my own imposter syndrome, self-limiting, um, mindset around these things where I was like, shit, no one's going to give me more than, you know, a few million bucks. And if I'm going to go out, try to raise five, but if I can only raise two, that's okay. And I'll just do that. And, um, I think it was like in two days, it was over five, and, um, basically then what happened was I realized that if I had over 99 LPs, I had to keep it under 10 legally, um, and I offered it to a bunch of my friends and family, because I, I'm a huge believer in, like, bringing people along for the ride, and a lot of my friends wanted to learn more about the things I was doing so quickly, the LP base grew past 99, and I had to keep it under 10, so then that was, like, the actual limiting cap on, uh, on going out and doing it. In terms of fund construction, um, it's going to be largely stage agnostic, um, but it'll probably concentrate around pre-seed, seed stuff. In this environment, you know, if there are slam dunk, you and I have talked about this, if there are slam dunk risk-adjusted opportunities that are Series B, I'm not going to pass up an opportunity to go and participate in something like that. It'll just have to be, you know, a bigger allocation, bigger check size into things like that…

AI assessment note: “if I had over 99 LPs, I had to keep it under 10 legally”

Q Did you see inflection points in, in your content and in audience growth?

A Yeah. I mean, scale is undefeated, right? So as you get bigger, it gets easier to grow. Um, point blank. I mean, full stop, right? The first 100,000 took, I don't know, eight, nine months. And then I think I've grown a 100,000 in the last. 45 days or 50 days. Um, so it definitely accelerates as you go, just cause you're on a bigger base. Um, the inflection points from an actual content perspective were more just around reps. You just are getting much better. I always think that if you look six months in the past at anything you're doing, like for you, if you go listen to episodes you've done six months ago, you should almost cringe at how shitty you were at this, uh, when you go look at that, because that's how you know that you're improving and that you're getting better at your craft. And that's how I always feel. I felt about my writing personally was like, I want to cringe when I go look at something that I did six months ago.

AI assessment note: “The first 100,000 took, I don't know, eight, nine months.”

Q Uh, but, uh, on them, like, what is the writing process for you look like on each thread? How do you decide which topic to focus on? Talk me through it.

A So I, I have what I call a Content engine. Like that's what I think is the, at the heart of a creator's process has to be a content engine, which is what allows you to produce high quality content consistently. So for me, I think of my content engine as all of the things I'm regularly consuming, the different newsletters, the podcasts I listened to, the things I watch, whatever it is, that's where I'm getting ideas, topics where I'm pulling out insights from them, novel insights, things that I, you know, made me go, Hmm, or Oh shit or whatever it was. Um, And then I log those, like I use notion, but I basically just log them into a board, um, where I have all of these ideas and different things that have popped up from, from that content engine. I'd log them all. Um, then when I get inspired around something to actually sit down and write, I'll look at that board and figure out what it was that I was inspired to write about. And I'll sit down and write in kind of an unstructured form prior to then distilling it down into something that actually works for Twitter.

AI assessment note: “when I get inspired around something to actually sit down and write, I'll look at that board”

Q I find you, I mean, I consider us both founders of media businesses, you know, the highs for me are very high, the lows are very low, and I think the thing that people forget is the speed between moving from one to the other is very fast. Mornings could be super high, and evenings could be super low. Do you find the same, or are you relatively even keel?

A I'm pretty even keel, and the reason I'm even keel is from lessons learned on the baseball field, um, because what I learned playing baseball was every time I got high, I'd get punched in the mouth. I was about to curse. Um, I'd get punched in the mouth, and every time I'd get too low, I would hold myself back from performing, and so what I learned was Um, I had to be even keel in order to perform at a high level consistently. Uh, and I think it plays out in everything in life, and it's a great lesson that's learned on the sports field that, like, Never get too low, because you're literally always one pitch away from getting out of any situation. Never get too high, because you're also always one pitch away from being just kicked in the nuts. Um, and that has allowed me, I think, to play out this, like, much more even keel. If something's going well, great, it's going well. Feel happy. Pat yourself on the back, sure, but just, like, know that you're one moment away from just getting punched in the mouth.

AI assessment note: “I'm pretty even keel, and the reason I'm even keel is from lessons learned”

Q he said something very simply. He said to me, you're never wrong to do the right thing, and it really just framed how I thought about this decision and a lot of decisions, and probably it's one of the most meaningful things that he's said to me. Um, when you think about your relationship with Tim, what are the biggest lessons or takeaways you think you have from that relationship?

A I think he is one of the most principled and value-driven people I've ever met, um, and I admire that deeply, because I think there are very few people in the world that are that way, who are So deeply connected with what their principles and values are, um, that they're able to let them guide every decision. And, and sometimes it looks like, uh, you aren't in a short-term decision you were making, but really the long-term view that you're taking around it is connected to what your principles and values are. And I've always really admired that about him, um, you know, both publicly and privately, the things that he does, the actions he takes, um, the friendships that he cultivates, um, the loyalty he has for friends and people who have been there with him. Um, I think that that is probably what I've taken away, and that's not necessarily something he has said explicitly to me. It's from watching and observing someone, you know, over a period of time, um, that I just truly, truly admire about him.

AI assessment note: “I think that that is probably what I've taken away”

Q Can I ask, I spoke to Greg Eisenberg, your podcast co-host and Kat, um, at Athletic Greens before the show. Um, and they both mentioned your insane work ethic. They said it was unparalleled. Um, again, why I think we get on. Um, but, like, what actually drives you? Like, why, why do you work so hard?

A I've never really been able to figure out what my internal engine is around things. I, you know, I grew up, Um, my mom is a first-generation immigrant. She grew up in India. Uh, my dad is white Jewish from the Bronx, and, um, his family, uh, didn't accept when he wanted to marry my mom. I never really met anyone on my dad's side of the family, which was just kind of a crazy set of circumstances. Um, but I grew up in a, in a household that was, like, very hard-working. My dad's a professor and I've never seen anyone work like my dad. I mean, to this day, I've never seen anyone put his head down and grind on things like my dad, and it wasn't blue collar work. He's a, he's a professor, um, but just so driven to learn and grow, and I always kind of just developed this, like, chip on my shoulder, um, thinking I wasn't the smartest. Like, I found ways to motivate myself, um, that I was like a fraud or an imposter all the time, and that, you know, you ask a question about insecurities. Like, my biggest insecurity is that I don't know what the fuck I'm doing. Excuse my language. Like that is my biggest insecurity in life is I'm constantly, um, fighting this urge of like, who am I? What am I doing? And I need to work really hard to continue to prove myself at every stage of what I'm doing along the way. Um, I think it's Josh Wolf that always says chips on shoulders, create chips and put…

AI assessment note: “I need to work really hard to continue to prove myself at every stage”

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 is a lot of firms suddenly having this awakening to the power of content, and hiring their heads of content, and really kind of digging in on what we do, and I, I always kind of shake my head, I think, what are you doing? Um, how do you feel when you see this kind of awakening of venture firms to the power of content, and their resources behind it?

A Well, I think it's interesting because we didn't build, we didn't build this audience. Like I never built an audience as a venture investor, right? My audience is not a bunch of other venture capital firms or venture associates. My audience is a bunch of real people that are looking to learn, grow, explore things, et cetera. Um, and in my opinion, that's much more powerful because that audience is real customers of whatever it is that these companies that I'm investing in are selling versus venture firms who, you know, their associates are told, Hey, go out and build an audience. And their audience ends up being a bunch of other venture associates who are all liking each other's things and sharing it. And that's, that's tough, right? Cause then they're, you're tweeting something out and you're sharing about a company and the only people that are seeing it are a bunch of other people within your little ecosystem. Um, Um, so I think they are going to run into challenges around that, and it's going to, it's going to require real defining for them to figure out what is our, you know, core value proposition of this content. Is it just so that we can tell our founders that we have, you know, a content arm and we're sharing, or is there a real reason for being, um, you know, real insights that are being driven through it? I think Andreessen is probably the best example of a firm who h…

AI assessment note: “it's going to be hard for a lot of these guys to do it”

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 take care of your full self in order to optimize creative work”

Q Did you see inflection points in, in your content and in audience growth?

A Yeah. I mean, scale is undefeated, right? So as you get bigger, it gets easier to grow. Um, point blank. I mean, full stop, right? The first 100,000 took, I don't know, eight, nine months. And then I think I've grown a 100,000 in the last. 45 days or 50 days. Um, so it definitely accelerates as you go, just cause you're on a bigger base. Um, the inflection points from an actual content perspective were more just around reps. You just are getting much better. I always think that if you look six months in the past at anything you're doing, like for you, if you go listen to episodes you've done six months ago, you should almost cringe at how shitty you were at this, uh, when you go look at that, because that's how you know that you're improving and that you're getting better at your craft. And that's how I always feel. I felt about my writing personally was like, I want to cringe when I go look at something that I did six months ago.

AI assessment note: “The first 100,000 took, I don't know, eight, nine months.”

Q he said something very simply. He said to me, you're never wrong to do the right thing, and it really just framed how I thought about this decision and a lot of decisions, and probably it's one of the most meaningful things that he's said to me. Um, when you think about your relationship with Tim, what are the biggest lessons or takeaways you think you have from that relationship?

A I think he is one of the most principled and value-driven people I've ever met, um, and I admire that deeply, because I think there are very few people in the world that are that way, who are So deeply connected with what their principles and values are, um, that they're able to let them guide every decision. And, and sometimes it looks like, uh, you aren't in a short-term decision you were making, but really the long-term view that you're taking around it is connected to what your principles and values are. And I've always really admired that about him, um, you know, both publicly and privately, the things that he does, the actions he takes, um, the friendships that he cultivates, um, the loyalty he has for friends and people who have been there with him. Um, I think that that is probably what I've taken away, and that's not necessarily something he has said explicitly to me. It's from watching and observing someone, you know, over a period of time, um, that I just truly, truly admire about him.

AI assessment note: “I think that that is probably what I've taken away”

Q How did you deal with that, fuck, you're not the best, and you're not actually number one anymore?

A I remember having a conversation with my dad. I called him and I was really upset thinking about academically, athletically. Um, and he just said, um, he said something to the effect of like, remember who you are and remember what you are great at, which is being consistent. Um, and I had never really thought of consistency as something that was my, a trait or something that I kind of held deeply. Um, But I guess it was. And so I realized that that was how I was going to win and outperform at anything I did was just by continuing to show up and just being relentless. Um, And that, that was when it kind of flipped for me. I was like, I'm never going to be the most talented. I'm never going to be the smartest. I'm never going to be the hottest. I'm never going to be the most, um, talented on the baseball field, whatever it was, but I'm just going to keep showing up. And it's really hard to keep someone down if they keep showing up. Really, really, really hard. Um, and so that was when it clipped, clipped for me personally.

AI assessment note: “I realized that that was how I was going to win and outperform”

Q Can I ask, I spoke to Greg Eisenberg, your podcast co-host and Kat, um, at Athletic Greens before the show. Um, and they both mentioned your insane work ethic. They said it was unparalleled. Um, again, why I think we get on. Um, but, like, what actually drives you? Like, why, why do you work so hard?

A I've never really been able to figure out what my internal engine is around things. I, you know, I grew up, Um, my mom is a first-generation immigrant. She grew up in India. Uh, my dad is white Jewish from the Bronx, and, um, his family, uh, didn't accept when he wanted to marry my mom. I never really met anyone on my dad's side of the family, which was just kind of a crazy set of circumstances. Um, but I grew up in a, in a household that was, like, very hard-working. My dad's a professor and I've never seen anyone work like my dad. I mean, to this day, I've never seen anyone put his head down and grind on things like my dad, and it wasn't blue collar work. He's a, he's a professor, um, but just so driven to learn and grow, and I always kind of just developed this, like, chip on my shoulder, um, thinking I wasn't the smartest. Like, I found ways to motivate myself, um, that I was like a fraud or an imposter all the time, and that, you know, you ask a question about insecurities. Like, my biggest insecurity is that I don't know what the fuck I'm doing. Excuse my language. Like that is my biggest insecurity in life is I'm constantly, um, fighting this urge of like, who am I? What am I doing? And I need to work really hard to continue to prove myself at every stage of what I'm doing along the way. Um, I think it's Josh Wolf that always says chips on shoulders, create chips and put…

AI assessment note: “I need to work really hard to continue to prove myself”

Q I find you, I mean, I consider us both founders of media businesses, you know, the highs for me are very high, the lows are very low, and I think the thing that people forget is the speed between moving from one to the other is very fast. Mornings could be super high, and evenings could be super low. Do you find the same, or are you relatively even keel?

A I'm pretty even keel, and the reason I'm even keel is from lessons learned on the baseball field, um, because what I learned playing baseball was every time I got high, I'd get punched in the mouth. I was about to curse. Um, I'd get punched in the mouth, and every time I'd get too low, I would hold myself back from performing, and so what I learned was Um, I had to be even keel in order to perform at a high level consistently. Uh, and I think it plays out in everything in life, and it's a great lesson that's learned on the sports field that, like, Never get too low, because you're literally always one pitch away from getting out of any situation. Never get too high, because you're also always one pitch away from being just kicked in the nuts. Um, and that has allowed me, I think, to play out this, like, much more even keel. If something's going well, great, it's going well. Feel happy. Pat yourself on the back, sure, but just, like, know that you're one moment away from just getting punched in the mouth.

AI assessment note: “I'm pretty even keel, and the reason I'm even keel is”

Q Uh, but, uh, on them, like, what is the writing process for you look like on each thread? How do you decide which topic to focus on? Talk me through it.

A So I, I have what I call a Content engine. Like that's what I think is the, at the heart of a creator's process has to be a content engine, which is what allows you to produce high quality content consistently. So for me, I think of my content engine as all of the things I'm regularly consuming, the different newsletters, the podcasts I listened to, the things I watch, whatever it is, that's where I'm getting ideas, topics where I'm pulling out insights from them, novel insights, things that I, you know, made me go, Hmm, or Oh shit or whatever it was. Um, And then I log those, like I use notion, but I basically just log them into a board, um, where I have all of these ideas and different things that have popped up from, from that content engine. I'd log them all. Um, then when I get inspired around something to actually sit down and write, I'll look at that board and figure out what it was that I was inspired to write about. And I'll sit down and write in kind of an unstructured form prior to then distilling it down into something that actually works for Twitter.

AI assessment note: “I'll look at that board and figure out what it was that I was inspired”