The Exchanges

Q So I guess around that time, you started your blog, you started putting things on Twitter, and really, you could say, took Twitter by storm. What was that pivot in your mind between the investing and the creative side?

A I started writing on Twitter in May of 2020. We were two months into COVID at that time. There was a whole lot of interesting stuff happening in the economic world at the time. Maybe, I don't know, I would put it up there in terms of one of the most interesting times in history, objectively. The market was ripping while the real economy was in the shitter. The Fed was pumping untold amounts of cash into the economy in all different ways, saying that there wasn't going to be inflation. Here we are. You know, a little while later, and clearly not the case. There was just so much that was happening, and there was unprecedented interest in learning about these things, was what I noticed. But the other side of it was that people were not delivering educational content in a way that made sense to me. And when I say that, what I saw was this bifurcation, where on one side you had experts, quote unquote, who pride themselves on talking over normal people's heads. On using jargon, on using acronyms, on sounding really smart, and a lot of that has been built up because it's a good business model. Let me talk over your head because then you'll pay me to do what you could do yourself. Then on the other end of the market, you had the TikTokers, people telling you to YOLO into GameStop call options, and what I saw was this market where no one was delivering the middle ground, the layman's te…

AI assessment note: “what I saw was this market where no one was delivering the middle ground”

Q You mentioned getting hurt, which I guess that resilience from freshman year kicked in. What did you think about from there coming out of college?

A That was the next big moment in my life where I felt like I got punched in the face, and that was probably the hardest one, because for a long time, I had defined myself in a very specific way. I had thought, okay, this is the moment that I'm training for is my junior year. After your junior year in baseball, you can get drafted and go play, and that junior season, I had sort of gotten hurt before the season. I had a very good year and pitched really well, but the velocity that I was throwing the baseball at steadily declined as my arm health Followed. And at the end of that year, I saw a bunch of my friends get drafted and go off to pursue their dreams, and I didn't. And I shouldn't have, to be totally fair, because by the end of that year, I was throwing, I don't know, like, 84 miles an hour. I wasn't a pro prospect at that point. But it was the first time I had realized, like, oh, wow, there's something actually else. This is not going to be the thing that I'm going to be able to do. And I thought, okay, I'll come back and play my senior year, and maybe I'll recover, and I'll try to get healthy. And I was still clinging to little hopes of that. But by my senior year, in the middle of that year, it became very clear to me that, It wasn't going to be in the cards. And I remember so distinctly the scariest thing of that decision was calling my dad and telling him that I was goi…

AI assessment note: “it was the first time I had realized, like, oh, wow, there's something actually else.”

Q And when did that get to the point where in your mind it shifted?

A Early 2021. I had rolled out a newsletter by then. My Twitter had surpassed a 100,000 followers, I think at the time. And basically I was making more money at the time on this side stuff that I was doing in my like 10 hours on the weekend than I was on my day job. And I started to think like, okay, it's been a nice side hustle and some income, but maybe there's actually something to this. Maybe there's a business to be built around it. Maybe I can parlay it into different things if I'm able to think commercially about it. And I've always been a little bit of a hustler. I just kind of have that mentality. I want to like try things out, test things, ideas, etc. And so I figured, okay, I really like investing. I really like all this writing and creative. What is an arena of investing where those two things come together? And what I saw was that the venture world did a lot of this. I was a big fan of Andreessen Horowitz, who was right in our, right in our backyard when I was out in Palo Alto. And They had prided themselves on that for years. All of their team had prioritized being on Twitter and having a presence. They had started right around that time, this kind of media arm called future. So they were doing a lot of writing. They were putting things out publicly. They were explaining things. They were building platforms. And so at that time I thought, okay, well maybe that's whe…

AI assessment note: “Early 2021. I had rolled out a newsletter by then.”

Q How do you manage your time? Because you can imagine as soon as you start investing in these companies, every single one of them will want you to help and leverage and amplify.

A Yeah, I mean, managing time is an interesting and challenging thing. I've gotten a lot better about saying no to things. That's, I would say, the number one unlock that I've had in my life over the last year. I, for a long time, was the person that said yes to everything. And I actually think in your twenties, you should say yes to everything. And I think your thirties or once you've started to have some sort of acceleration in your career is like the time to start saying no to most everything. Saying yes gets you into a bunch of rooms. You have a bunch of the lucky opportunities, the things that hit you. And then saying no allows you to get leverage on the things that you're starting to do well. And so for me, I've just learned to start saying no to things that aren't going to push forward against my daily actions. That has unlocked a whole lot of time. I used to, and in my prior job, that was more of my job. I spent all day emailing or on phone calls or in meetings. I don't have to do that anymore, really. And so if I don't want to take phone calls, if I want to spend a day writing, if I want to block out four hours to write in the mornings, I can do that. And it's actually core to exactly what I'm trying to do and build. And so I've had to build in systems to the point earlier that allow me to achieve my goals. Part of that system is I mainly only do calls on Fridays. Part o…

AI assessment note: “Part of that system is I mainly only do calls on Fridays.”

Q What did you come to learn about investing over the eight years you were there?

A Yeah, so many things. Well, first off, you can read every damn book in the world, but until you get your hands dirty, you don't know a thing. That whole summer before starting, I remember really just dedicating myself to, like, five to 10 hours a day of just reading, doing whatever I could to absorb everything. I wanted to know everything about private equity before I got in. I must have spent a thousand hours over the, something absurd. And I got to work, and I literally knew nothing. Everything was different than what I had read in the books, everything that was theoretical, putting into Practice was really different. So I remember realizing it was apprenticeship. You had to get in and get your hands dirty and learn from someone and be around someone. I was fortunate to be in an environment where they really prided themselves on mentorship and apprenticeship. From an investing standpoint, I would say one of the biggest realizations I had was that it is very, very difficult to fight a bad market. And what I mean by that is you can invest in the best business in a shitty declining market. And really have a tough time. And you can invest in an okay business in a great growing market and do much better with that, especially with the private equity model of like levering up cash flows. I just found that to be such an important point for investors to realize there of just like the …

AI assessment note: “one of the biggest realizations I had was that it is very, very difficult to fight a bad market.”

Q Well, I know there's a lot to your story, and why don't we just start at the beginning?

A Yeah, let's start at the beginning. So I was born on, no, no, I'm just kidding. I'll save you the time. So I, um, grew up in the Boston area. I was born in New York. My dad's a professor, so grew up in a household that really prioritized academics. My dad was a professor. My mom is Indian, and so I, like, had this kind of, like, mixed-race background, and also one that really prioritized school. And I had one older sister who was really, like, the The golden child of the family. I say that in a very loving way. My sister is the most amazing person I know, but she was the, like, academic all-star a few years older than me, always had the highest GPA in the school and performing extremely well, and I was kind of the, like, ne'er-do-well son who was going around throwing a ball, and especially for my Indian mother, it was, like, a little bit of a struggle to figure out how I was gonna fit in or make it, I just think the traditional construct in which a lot of immigrant families think is that you have to kind of prioritize really following the neatly trodden path, right? It's like, You come, and you work hard in school, and you do well, and then you go and get your college degree, and then you get a master's or a PhD, and my dad was an academic, so that was the track he had followed. My grandfather on my mom's side was similarly a professor, and so that was really what I think my m…

AI assessment note: “I grew up in the Boston area. I was born in New York.”

Q If you went back, how would you trace your trajectory from self-admittedly knowing nothing to where you were, felt like it was time for you to move on?

A I have always pursued Learning and pursued growth as my kind of end game. I wanted to be around really smart people. That was why I was so excited to accept that role when I first joined. And I was so excited to be drinking from a fire hose around something the way I felt like I was for so much of my life playing baseball. And for every year I was there, I constantly felt like I was learning new things. There was new experiences. There were new opportunities. The market was changing. We were doing bigger deals. The funds were growing. There was always something new that To learn something new to grow around. But for me personally, the change point was when COVID hit. I wasn't working 80 to a hundred hour weeks on a plane three to four days a week. And I had more time to sit and to think, okay, where am I? Take stock of my life, of my career, of my family, of all these different things. Because what I find is when you're in the heat of battle, it's very hard to like zoom out and Say like, why are we fighting this war? Right? Zoom out because you're just in it. And that career path, private equity, hedge funds, you're in the heat of battle constantly. Every single day, you're fighting for your life because there's always someone that's trying to take your lunch. And COVID uniquely provided an opportunity to take stock of the war. And for me personally, what I found was there was …

AI assessment note: “for me personally, the change point was when COVID hit.”

Q There's a tremendous amount that you talk about that are these sort of you setting goals, going after systems, course correcting. What about luck?

A I'm a big, big believer in luck, but I also think that a lot of luck is mischaracterized. I think that there are really two types of luck. There's like true luck, which is things you truly cannot control, where you're born, who you're born to, what side of the world you're born on, all of those things. Cannot control them. And then there's the other kind of luck, which I think you can engineer. And that is luck that is susceptible to situational enhancements, say. I call it engineered serendipity, but you can think of it as taking daily actions that increase your luck surface area. And the story I typically think about when I think on that is in the movie Interstellar, there's this scene where the main characters are talking about this planet that sits right next to a black hole. And they're commenting on why there isn't any life on that planet, because it seemed so ripe for life. And what they realize is that sitting so close to a black hole, there was no opportunity for those chance collisions of the universe to happen that sparked life. Like the asteroids got sucked into the black hole, the little things that would have otherwise hit the planet were getting sucked into the black hole, all of that. And it didn't allow life to be sparked. And so I think about that personally when I'm going through life. What are the black holes that are sitting there in your life that are prev…

AI assessment note: “I'm a big, big believer in luck, but I also think that a lot of luck is mischaracterized.”

Q How do you think about in that consistency and process lens that you like to use, touching base with, let's say, five, 10, 15 people that you view as your personal board of directors?

A So I don't think there's a standard framework for how often or how frequently you need to do it. I think of this as, like, depth of relationships. These people should be people that You truly count as a deep relationship in your life. I don't think you can reasonably go to someone that you just met and say like, hey, Ted, just met you to film this. Will you be my, on my board of advisors? Hey, how about it? Why not? Because you shouldn't want that person anyway. They're not going to be invested in your journey. They're not going to be invested in what you're building. You want to really have this be a natural outflow, and it's not actually something you need to ask someone either. I think that idea of like, will you be my mentor? It sounds like I'm asking someone to be my girlfriend when I'm in middle school. That's just not the way life works anymore. I don't think any of my mentors or people that would be on my personal board of advisors would say that I ever formally asked them to do anything. Tim Cook has been someone who I've talked about publicly as someone that I've learned a tremendous amount from over the years. I met Tim at the gym in 2014. He happened to be one of the eight people that was crazy enough to show up at Equinox at five in the morning every single day. And he remains to this day I think the hardest worker in the world, like it has to be crazy working for …

AI assessment note: “I don't think there's a standard framework for how often or how frequently”