He Built An 8-Figure Business Off Tweeting | Sahil Bloom

I constantly get asked, like, oh, what was the hack? What was the growth hack? There was no hack. Twitter was like the most surface level. Expanded to newsletter, grew that, signed the book deal. When I get into something, I'm gonna do this for 10 years. That's the minimum amount of time that I'm committing to doing this. There's like a lot of, I haven't done the thing, but I'm gonna write about it. If you're talking about it like you've done it and you haven't done shit, that's just inauthentic, right? It's not real. Go do the thing in the real world and talk about it along the way.

That's interesting content. I think you focused on Twitter first and then you really started to compound. And so I want to dive into how that happened initially.

I was working in private equity, so I had no plans. Like, I wasn't— I don't know what— I didn't know what the creator economy was. I didn't know what an influencer was other than like Kim Kardashian or whatever. COVID hit and I had more time on my hands. I was kind of trying to like figure out what to do with my spare time. I was stuck at home. I had no social life and I'd always loved writing. And what I figured was like, I'll just— this will be like an interesting hobby. And so I started doing it on the weekends. I had 500 followers at the time. This is like May of 2020. And it was very clear to me early on that there was like some pull for the stuff I was talking about. Originally, it was like finance explainers. Like I was kind of explaining finance topics in simple terms. It started like taking off a little bit and the like positive reinforcement I was getting encouraged me to do more of it. So on the weekends, I was spending a little more time on it and it was continuing to But I never, there was never like, oh hey, I'm gonna go become an influencer, or hey, I'm gonna go become a creator and this is gonna be a job, right? Like I had a lucrative job, I was doing well, I was on a good track. I didn't love it, but it was good and you're getting patted on the back for being successful. For me at least, one of the big takeaways was like, I never set out to become a creator. I was writing about things I knew and things I understood. And then as I expanded it, I was writing about things I was struggling with, like my own life, life experiences, problems I was wrestling with. And things like I was really learning by actually doing them in the real world. So I was never like, hey, I read this, you know, in some book and I've never thought about it and let me just like share it with you. Or like, here are 10 TED Talks that'll change your life. Like, my whole thing was always if a 22-year-old kid with no life experience can do this same piece of content, I probably shouldn't share it. It should really be things that like I am uniquely qualified to share. And that made a big difference. So yeah, I mean, Twitter was the first place. I wrote a ton there. My general perspective was like, let me just figure out layers of depth. So if Twitter was like the most surface level, the next layer of depth would be newsletter. So I expanded to newsletter, grew that. Next layer of depth would be book. So I signed the book deal, working on that, and then expanding mediums and like expanding the surface area. So that's, you know, with all the video stuff I do now and kind of growing from there.

You're spending at least 5,000 hours In the first year on this.

Yeah, it was, I mean, countless, countless hours. Like, this is no— there was no hack. I mean, people constantly— I constantly get asked, like, oh, what was the hack? What was the growth hack? What was the, you know, engagement groups? Like, everyone wants to point to the thing that was, like, the hack. The hack was that I wrote 300,000 words on Twitter. Like, I literally just wrote an unbelievable amount. And, like, some of it worked, some of it was duds, some of it was great, like, some of it was medium. And That was the real thing, was like I showed up every single week for a long, long period of time. That was it.

You just gotta do the work, straight up. Yeah. Here's the thing, like I'll experiment with things 'cause that's kinda my job as a marketer, right? So like on my Twitter, this guy reaches out to me. He's like, hey, we do these threads for people. It's all these other like creators. And it's like, yes, clearly like these are people writing these stories that are super long. And so he does a couple for me. And you know, yes, they get 2 million views or whatever. I'm like, great. It totally doesn't sound like me, and also, who cares?

Yeah. I think I know this person. So, if it's the kid that I think, uh, I actually, like, uh, had an issue with him, because he told people— so, I've always, 100% of the time, I've never had a ghostwriter. I write all my own stuff, 'cause I love writing. That's my thing. And this kid wrote a message to one of my close friends, Sean Puri, uh, saying that he did ghostwriting for me. And Sean is one of my close friends, so Sean texted me and was like, hey, does this guy write for you? I'm thinking, you know, I'm like thinking of engaging, him on one of my companies or something. And I was like, what? Like, no, absolutely not. And he was like insinuating that he had written for me. And so I reached out to him and I sent him like kind of a joking message and said like, hey, my attorneys will be in touch.

Yeah.

And he freaked out. And I was joking, but I just wanted to scare him.

Yeah.

And he, like, you know, and then I basically told him like, look, you're a 20-year-old kid. This is a learning lesson for you. Never do that. Like, don't use people's names that you actually haven't worked with because the world is so small. I mean, Sean literally like within minutes had texted me and I knew, and then I was messaging this kid. So you have to be really careful. Like, if you're trying to build your reputation as a service provider, the other thing is like, you have to ask people before you use their name in any marketing. I mean, this happened with Sean, like with Milk Road. He had that big, you know, like public spat with a guy that did his newsletter growth.

Yeah, yeah, yeah.

Because like, you have to be careful about whose name, you have to ask. Like, if you're an agency operator, you have to ask and get consent from someone that you can use their name in your marketing. And like, for any agency operators out there, that's just like, you have to do that, full stop. But yeah, I mean, I agree. Back to your point on the ghostwriting, like, it goes to my point of when you're creating a piece of content, if you are someone that is actually doing real things in the real world, you should want any piece of content you put out to be something that only you could write.

Right.

It shouldn't be something that a 22-year-old kid using ChatGPT can write, because then, like, who cares?

Yeah.

Yeah, could I— I mean, I could go around and basically go find interesting things someone else had written that like, oh, they only have 1,000 followers, but they wrote something good and I could just repurpose it, write it my own way. And I have a million followers. It'll get a whole lot more views than their version did. But like, if anyone can write, then like, what value is that actually creating for me in the long run? It's just like, it's stupid, right? It's like fairy dust.

Yep. It's, it's also not authentic either. I mean, with all the AI stuff coming out, it's like, yeah, you have to either have original stories or experiences or you have to have original data.

Yeah. I mean, it's kind of my lamentation with the, like, creator world as it stands today, which, like, basically when I was getting started, creator or influencer, it wasn't really a thing. It wasn't like a career path, right? You could go make some money doing it short-term, but it wasn't like, oh, Mom, I'm gonna go become a creator. This is what I'm gonna do. And so when I thought about it, it was all about, like, real experiences and authentic things that you were doing. You had to go do things in the real world, and then you could talk about them.

Yeah.

Now there's a lot of, I haven't done the thing, but I'm going to write about it. A business guru talking about business principles when they live in a 500-square-foot studio and they haven't made any money or had business success is weird. That's weird to me, right?

Mm-hmm.

Because then you're just like, wait, you're writing about someone else's book basically if you haven't actually experienced or built the thing. And similarly, if you're a fitness influencer and trying to build a fitness creator ecosystem, but you're not fit, Like, why would I listen to you on that?

Right.

You know, it's like a running influencer that doesn't have stats to back up the fact that they're a good runner. It's like, it's a weird thing that is— that now exists. And so, like, if I give advice to anyone that wants to be a creator, it's like, go do the thing in the real world and talk about it along the way. Like, you can talk about the journey of doing it and the experience and the struggle and the, like, successes and the failures. That's interesting content because that's like the path that a lot of people are on. If you're talking about it like you've done it and you haven't done shit, That's, like, that's just inauthentic, right? It's not real.

That's just grifter level.

Yeah. It's not real.

Yeah. Well, here's the thing, too. So, it's definitely creating, right? And it's plus being consistent, because I don't think you've stopped tweeting since 2020, right?

Yeah. I mean, consistency is the foundation of everything. Like, this is a common trope. It's true, though. Like, you just have to keep showing up. And you have to not... be so short-term that you get discouraged when things don't work, because there are going to be just valleys where for a long period of time, and I'm not talking 1 or 2 posts, you might go 3 months where your open rates are really low on a newsletter and you don't know why, or your engagement's really far down. And the people that you know aren't going to make it are the people that you then see posting, the algorithm's changed and it's so bad and they need to change it back. Elon Musk ruining Twitter. And The really great people, like I just, I had lunch with Mark Manson, The Subtle Art of Not Giving a Fuck. Amazing guy. He's been around for 20 years, right? Like he's writing Facebook blogs back in the day. He's created all these things. And his whole thing is like, yeah, the algorithms change. Like that's part of the game. That's why it's hard to be here for 20 years. You just have to figure it out. Like sitting around complaining about it and like getting down during those valleys versus like figuring out, okay, what works? Like how do I, operate at the, you know, at the intersection of what I like and what's working in the algorithm today, rather than just sitting around being like, oh, the thing's changed. This is crap. Elon Musk, change it back.

Got it. And then just to get a little more granular here, the threads. So you're doing 3 per week initially. You're working a full-time job. These have to be taking you a couple of hours per thread.

Yeah. Early on, I mean, each one was taking me at least 4 hours because I was doing a lot of research to make sure they were really good. I was like refining them a lot. I hadn't built the muscle yet, so it wasn't easy. It wasn't coming quickly.

And I think you were like— you didn't have any followers, right? And I think you tweeted something, and then I think it was Chamath or something that shared it. So, how did the growth look in the first year?

I started at about 500 followers. I posted my first thread. Nothing happened for the first few hours. Uh, I commented underneath something that Chamath posted, and this is before Chamath was, like, Chamath. He wasn't super famous yet. He had a decent following, but he wasn't enormous. It was before all the SPAC boom and stuff. I commented underneath something that was related that he had said. He then shared my thing and said, this is good. That sort of spiked me to like 2,000 followers, maybe. Um, and that was kind of the start. I think by the end— that was May of 2020. By the end of 2020, I was probably at about 70,000, 75,000 followers on Twitter. That was my only platform, though. I didn't have anything else. Um, and then by the time I quit my job, which was May of 2021, I was probably at about, uh...

100,000.

175,000.

What was your initial cadence on Twitter? 'Cause I think my understanding is you are usually writing off the cuff. I think you're like, screw the content calendar.

Yeah, I can't do the content calendar. I, um, yeah, I just— I'm terrible at doing things in advance. I just can't do it. I won't be able to motivate myself. And I have to work from inspiration. It's something I'm actually excited to write about. Uh, so I— originally, I was probably writing about 2 threads a week. And I was working a full-time job, so it was sort of like that was all I could do.

Mm-hmm.

I don't think I ever really went more than that, and I just stuck to it. I think I never missed a week. Even still, I launched my newsletter May of 2021. I've sent 2 newsletters every single week since then. No Christmas off, no holidays off, no birthday off, just have done it the entire way through. And that's kind of how I'm wired. When I get into something, I'm going to do this for 10 years. Like, I'm just going to do it. And that's the minimum amount of time that I'm committing to doing this. And it's either going to work after 10 years or it's not. But I'm not doing it for like 3 months and figure it out, you know, and then just being like, ah, you know, it didn't work. I want to learn and I want to get better at it and improve. So taking that long-term view was very important to me from the outset.

Got it. Now, in the morning when you're— because again, I don't think you have a content calendar right now. So one, where are you drawing the inspiration from and how What's like your content block in the morning, if you even have one?

Yeah, every morning from 5 to 7:30 is when I create. It's the only time of day that I'm creative. It's before my son and wife wake up. Get out of the cold plunge, which I do every morning religiously when I'm at home at least, and basically go sit down at my desk. And that's when I feel creative and that's when I can create. That's been a lot of book writing, some newsletter writing, and then it's, you know, for the for the social platforms. What do I draw inspiration from? It's my own life. It's literally things I'm reading, things I'm interested in, problems I'm struggling with, questions I'm asking myself, those kind of things. And that makes it authentic for me where I feel like I can do it for a long period of time. And it means that it's unique. It's not, again, it's not something that anyone can do, because I might read a concept, think it's really interesting. But for me to write about it, then I need to place my own perspective and lens and, like, how I wrestled with it personally to be able to go share it. And that's the part that, like, you can't replicate. That's 'cause that's me. That's my own, you know, unique view on it.

OK, so I know, like, with Alex Hormozi, the way he does it on Twitter, he's really giving advice to his younger self. And it's— I can see how tough he's being on his younger self, right? For you, is it just like you're drawing from experiences, but there's also like, hey, like, you should do this?

I try to avoid you should do this type stuff. The main reason I— so I do some of that where I feel like it's advice to my younger self. And I explicitly say like, this is the things I wish I knew when I was 22, that I feel like I've kind of learned at this point in my life about these different areas. Usually I try to avoid it. And the reason is my answers to these questions are gonna be different than yours, are gonna be different than our friends, are gonna be different than our parents. At any stage of your life, the problems and the questions I'm asking are universal, but the answers are entirely driven by your circumstances, your perspectives, the things you want, like what season of your life you're in. And so my goal with all of it is to help you ask slightly better questions, to help you wrestle with them slightly better, but not to give you the answer to it, because I actually don't know the answer for you.

Pre-show, you mentioned that you're bearish on the creator economy, so let's start there.

I think it's what I said, which is, like, there's a lot of people that have gotten into this because they think it's a lucrative career track, but they haven't actually done anything yet in the real world, like creating real experiences. And that I am really bearish on. I don't think you can do that for a long period of time. Yeah. I think you can probably do that for a short period of time. You can hack your way to a decent-sized audience. Like, if I were to start from zero on Twitter, LinkedIn, wherever, and you told me, like, hey, you have to make... If it was today, so like October, and you told me, hey, you have to make $1 million in 2024, so next year. So I have sort of 3 months to build it, and then I have to make $1 million next year. I think I could probably do that. But then I think it would fall off a cliff in 2025. Like, I think I could for maybe like maybe a year, 2 years, 3 years, like hack your way where you could like convince people you're legit for a short period of time, do some like course or something, you know, at brand deals on Instagram, whatever. Like, I think I could hack my way to doing that, but that's not a lasting viable career. Like, if you want to have a career doing this, you're talking 30-plus years, right? Like 20, 30, 40 years. There's no precedent for that in the creator economy. The best precedent that exists is people like Tim Ferriss or Mark Manson who have like been doing this for 20 years. And that's really freaking hard to do. Like you ask them, they've probably seen so many people come and go during the different phases of their life in these spaces.

Totally.

And so my firm perspective is that if you are going to do this, you need to like really approach it differently and there needs to be a longer-term view and vision. And a lot of that has to be grounded in things you're actually doing or building in the real world. Like the accounts on Twitter, that I think are most interesting are the ones that are in some niche space and then just talking about it publicly, like Car Dealership Guy. He's a friend of mine in real life, but he's doing those things in the real world and then he's talking about them. He's built a big audience talking about this weird niche thing of auto dealerships and used car financing and all these things. That is super cool and he's gonna build an enormous empire around these different things because now he has a huge audience of people interested in car dealerships. The potential to launch businesses around that is enormous. And businesses that have real enterprise value, that have durable cash flow streams, totally different from like hand-to-mouth brand deals of like so-and-so is going to pay you $5,000 to do an Instagram reel. And that's just a very, very different thing.

I keep going back to the Warren Buffett quote here where it's like, if you're not going to hold this stock for 10 years, don't even hold it for 10 seconds. And it applies for everything.

That's a great quote. I've never heard that one. Yeah, that's fantastic.

I'm pretty sure it was him. Yeah, this is okay. So this is where it's like You have this creator-led agency where you guys will cut up clips, right? I think it was called Viral Cuts, correct? I tried it for a little bit. I think my take on this one is I think most of them are gonna go out of business. And my reason—

I think so too, by the way.

Yeah.

I just don't think ours is gonna go out of business.

Well, I think, okay, so for you, for example, like, you know, you've been in PE, like you jumping around, like I think there's a good strategic brain and like you don't wanna tarnish your name, right? So I think yours is gonna be fine. I think the other ones, Because they're going to have like an influx of customers and there's going to be a big operational issue and they can't— the churn is going to go through the roof.

I mean, when you think about— so, so what you're referring to is like a broader holding company called Assembly, partnered with a good friend of mine who's built and sold 2 8-figure agencies in the past. He's a laser-focused operator, right? I'm not. I have the network and the connections and the partnerships and the strategy. So we have a lot of complementarity in our skill sets, which is great. But The view from us was you can basically leverage creators as distribution when there's product-audience fit. So the best example, you referenced ViralCuts, which is with Cody Sanchez and Sam Parr.

Mmhmm.

They do a lot of clips. Cody in particular has built an enormous audience off of doing clips. What we've learned, by the way, is like, you're actually not a good customer. The best customer is a business that is looking to do tons of video clips and ads versus creators who tend to be like, just like shorter-term customers in general, because if it's like working or not working and, you know, the price point not for you because you have businesses, but like the price point is significant, it's $5,000 to $10,000 a month. A business can easily invest that in doing more direct response ads and doing more brand ads and all those things. And so the vast majority of that business, which is now, you know, multi-seven-figure run rate business, is, is going to be B2B. You know, it's real. It's businesses on the other end. The best example of this is like Hey Friends with, with Ali Abdaal, our shared friend. where Ali had this amazing course, the Part-Time YouTuber Academy that he had built, incredible audience around, you know, helping YouTubers build their YouTube presence. Well, like, for me, I could take that course, but I don't wanna go edit YouTube videos. Yeah, I don't wanna do this. I don't have time for that. I'm not good at that. It's not my skill set. I want someone to just do it for me, and I'm happy to pay. And there's tons of people and businesses that are like that, where they want the Ali editing, you know, quality and style and all of the, like, strategy and thumbnails and all of those things, but they don't wanna actually do it. And so for Ali to launch this premium offering that actually does it for you makes a ton of sense and there's a ton of leads to your point. Now the real devil is in the details of how you actually service with quality those leads. That is gonna be the thing that makes most of these businesses go belly up. I tweeted this today that services businesses sound great because you make cash from day one. The reality is building a tiny little services business is quite easy. 5 clients for a YouTube business like that, charging $10,000 a month. If it's just you that runs that, you're making $50,000 a month, you feel rich. That's a great little business.

Yeah.

Taking that business to where it's doing $500K a month is miserable and extraordinarily difficult and requires like a very specific set of skills. I mean, now with these video-based businesses, we have like 100 employees and you're having to manage all of these different editors and you need PMs and you need a GM at different business units. That's like all of a sudden you're talking about like you need a culture and you need, you know, HR policies and you need company offsites. Like that's a real business at that point. And so that's why I agree with you that I think most of these like, you know, sort of fly-by-night creator-led agencies that are getting started or creator-led services businesses that are getting started are gonna have a really tough time because they don't have the actual business background or the business partner that is actually gonna understand how to like navigate the inevitable enormous challenges that come with these businesses.

Got it. That's a good point. And so I guess the question would be, with the— are you the holdco here? Are you involved with all these agencies?

Yeah.

Okay.

Yeah. So the holdco basically is like the shared services layer that builds and launches all of these different services businesses. It's not always going to be just services businesses. The idea is like, I think— I mean, this is my finance background, but I call it a bond with a call option. So like the services businesses are a cash-flowing bond. They are cash flow from day one. They're generating a ton of cash today, like 50% net margins across the whole thing. And you can then take and invest the cash flow from that bond into call option upside bets. And when I say upside, I mean real enterprise value, because we know this, services businesses don't typically trade at a great premium. They don't have a ton of enterprise value. They don't trade at a great multiple. But a CPG business or an app business or a software business will trade at a great multiple. And so those are your call option upside bets, that require some upfront investment of capital. And you can do the whole thing in a really nice way if you're like taking the cash flow from the services stuff and funding the bigger upside bets.

I'll give you the flip side.

Yeah, please.

So, so my podcast co-host Neil, so he bootstrapped the agency to 9 figures. Yeah, it took about 4 or 5 years to do it off his, off his audience. And so my mindset was always like the same. It's like, you know, there's more scalable, you know, Things with higher upside, you know, better multiples and everything. And what I didn't realize until maybe a couple of years ago or so was that if the agency has, let's say, over $5 million in EBITDA, you're getting like— this is like pre-2022, but you're getting 15 to 20x multiples, right? And it's like, it's pretty significant. I just think most people don't know about that. And so I got myself, I got trapped in doing too many different things. And now for me, I'm just laser-focused on—

That's interesting.

Yeah.

I mean, it's a good counterpoint. I think that, I mean, even if it's come down a ton and it's 10x EBITDA or 8x EBITDA, at $5 million, you're talking about you just created $40 million of enterprise value without having to invest a whole ton of capital upfront. I think it's really, really interesting and I think it's an interesting space, but now you see everyone is— there's been a ton of people that have tried to launch these things, but there's no business background to it, right? So I really think— I don't have any business background running an agency. My partner does. If I were to just go try to do this on my own, we either would've died while trying to scale and take on these leads, or we would've had to stop at $50K a month. And as an individual, again, if you just want to stop at $50K a month, that's a great business. And I know a ton of ghostwriters that have a little ghostwriting agency that makes $50K to $75K a month and That's an amazing business as an individual. You just, you bought yourself a job, but it's a high-paying job and it's like a high cash flow job. And that's a great life. If you're young and you're doing that, you can make good money doing it. It's just like if you want to go build the thing that is then, you know, on the accelerator path to being a real big business, $100 million of enterprise value, whatever it is, you have to think differently. There has to be another, another layer to it.

So is your playbook, I guess, on the holdco, are you going to just keep cash flowing or are you looking to sell them? Like, what's the play?

I mean, as of now, keep cash flowing and own 100% of it, across me and my partner. Today, there's a handful of video businesses, there's a handful of design businesses. I own a newsletter growth business that has scaled a bunch, own a premium content agency business. So there's a bunch under there. They all have real operators running them. I would guess at this point, I think most of them will survive and do well. I think a couple of them will just be small and nichey, and then a couple will be really successful. And so the question then will be, what do you do with the ones that are really successful? Do you just keep it as part of the whole and cash flow it? And look, if the thing is cash flowing $10 million a year, is there a reason to sell it? Or do you just say, why would I sell that? In our private equity days, my fund owned A really large— the largest franchisee of Taco Bells in the world. And it cash flowed $50+ million a year. And you're sort of just like, why would we ever sell this? Again, it's like a bond that's just paying you an enormous dividend every single year. And sometimes there's just not a reason. Unless someone is willing to pay you so much that it takes off so many years of that future dividend that you're going to take, Why? Why sell it?

Makes sense. Do you think— I mean, look, you're getting a lot of leads right now and then you're getting clients through the holding company, too. Have you taken any equity in these other businesses or these other creators yet?

Have I? So what do you mean by that?

So it's like, you know, let's say I invest in you as a creator, right? Like, I invest in Sahil, the brand.

I haven't done that. I get asked about that a lot. I think it's tricky because you sort of like— have you seen The Last Dance? The Michael Jordan— so, like, Scottie Pippen, uh, he signs that preemptive deal with the Bulls, and then he's outperforming it and he's pissed. And he's like, I wanna renegotiate. I'm pissed. Like, it's, it's a— it's like an adverse thing that, that, uh, it's like he's now, um, upset because he signed that preemptive deal. I think you'd be opening yourself up to a lot of similar things where, like, say you invest in a creator, you take 20% of their future earnings, you're gonna provide them services. If they, like, become MrBeast and you somehow own 20%, you don't think they're gonna be pissed?

Oh, yeah.

When you're no longer really providing them value, And you're taking 20%, it creates this weird environment where the success stories are actually going to be the ones that are really angry about it versus venture where, yeah, if I give you the money upfront, you grow. Are you annoyed that I might own 20% of your business when I didn't contribute? Maybe, but you can't do anything about it. It's very stock and trade. These income share agreements haven't fully been litigated or played out, and they are a little sketchy sometimes in how people perceive them. It happens a lot in athletics. I think there's an interesting— I was thinking about this at breakfast before coming over, actually. I think there's maybe something interesting to do with athletes, given the NIL stuff in college. If you could basically sign on athletes and say, hey, we're going to help you blow up your brand, which is going to make you way more valuable as an athlete, whether or not you have a successful sports career, I'm providing you value via like, hey, we're going to do all of your clip editing, we're going to launch tons of stuff for you. We can get you all of this stuff that helps expand your brand, which is going to make you more valuable and make you money. And we'll take the cash on the back end and be providing you these services for free. That's kind of an interesting model potentially. I was literally like on the way over here, was thinking about it and I was thinking about texting my business partner like, I wonder if we should think about helping athletes grow their brands. It's kind of an interesting idea.

I love it. Yeah. Your business partner is Hunter, correct?

Yeah.

So how do you— I mean, He seems like a really smart guy and he seems credible. How— I mean, for people looking to do this, they're like, oh, okay, I want to— I don't want to operate. I want to become a creator like Sahil, right? But I need to find a good operator. How did you find Hunter?

Through my, like, friend groups and network. If I have one thing about me that is actually truly unique, it's my network of friends and people and the people I have access to. And it compounds and it's really hard to compete with at some point because of the way it compounds. the people that I feel like I can reach out to, text, talk to. And so Hunter, yeah, I met through several common friends. We became friends over a period of a couple years, spent a bunch of time together talking business stuff when we weren't working together. And then, because he was working on his other thing that he had scaled up and was deciding how to sell it or what to do with it, I was working on all my stuff and growing my platform. And then basically we both had the idea at the same time and we were just on one of our, we would do regular jam sessions where we would just chat about business stuff. And I was like, hey, I have an an idea for you. He was like, I have an idea for you. And we both pitched each other the exact same idea. So we were like, oh, we should go do this. We should just do it together. But it was like, again, you know, just like the network and people around there. There's not really— I mean, I've— we've thought about that as a business angle with our holdco of launching like a, like an On Deck for, for this type of thing where you kind of like are— yeah, where you're like matching, you know, On Deck was like matching founder co-founders, but like, can you do that where you're matching creators with operators?

Interesting. It could be like an On Deck/YC type of thing.

Yeah. You're incubating— I mean, we would love to do that, right? It's sort of like, um, CAA or Knight Media has done it on the product side with creators. Um, I think that's really interesting. Can you incubate creators? It goes to my point on the athletes. Like, you're incubating an athlete, um, to build their brand, because they're great at their sport, but they're not probably great yet at building their brand and knowing how to do all these different things. So, can you incubate people Um, and, uh, and create a world where you're then partnering them with an operator to go launch something. And you're kind of incubating the operator, too, and helping them, providing services, helping them come up with the idea, whatever it might be.

And how is your content team structured right now, and how much are you spending roughly, you think, per month?

So, I have— I mean, my actual team is me. Um, and then most of, like, team, if you think about it, is around video stuff. Um, so I have, like, anytime I go on a podcast, I get the raw footage. Um, There's an agency that I own that also does all the chopping up of clips and creates all the stuff for me, posts. I actually do all the posting myself because I like to try to like figure out the platforms and how they work and what works and what doesn't. But that's where I get all my clips from. Prior to owning these businesses, I was probably spending about like $20K a month across video editing stuff, newsletter growth, like backend operations on the newsletter, trying to think what else would have fallen into that, like, you know, kind of chief of staff type services that were outsourced. I now have like one chief of staff who's sort of like my main point person that kind of like runs, like keeps the trains running on time with everything so that it allows me to kind of like sit in the clouds and just focus on the creative stuff.

The chief of staff thing is one thing I've been championing all my founder friends. It's like, dude, this is the best thing ever. And I read this book, The Great CEO Within. So, you know, this is a couple of years ago, but Matt Moschari, the guy that coaches Naval and like, you know, Sam Altman, or whatever. He's like, you know, I'm not gonna coach you unless you have a chief of staff. And then he has this whole write-up and I'm like, oh, you know what? We'll just give it a shot. And so, it's been the most liberating thing for me to have one. And it's just like, it's like a duplicate version of me because she sits in all my meetings. She sees all my patterns, right? And so, can you talk about like how it's structured for you?

Yeah. I mean, it's very similar. It's been an enormous unlock for my life. And Yeah, he has a very different skillset than me, which is he is unbelievably operationally focused and very organized. I am scattered and like to be creative, and I like to be able to float around things and focus on the strategy more and the vision and less on the Notion database and less on making sure we're delivering the things we need to for our different companies. And now that the ecosystem has grown, I've got this holding company that has 10 or so businesses in it. I've got my I've got the venture fund, I've got all the content stuff, and all of those things have different needs and different stuff going on. And if it was me having to like have my brain context switching, it would be really hard for me to do the creative stuff well.

Yeah.

And so his role is like, make it so that I don't have to context switch. Like he manages it, we kind of centralize it all into like one little like, you know, sort of to-do list where it's like things that I actually have to do that I know I can process during a, you know, fixed period of time. And then I get to focus and float in the clouds on the things that I'm really good at.

And what's like your communication cadence with your chief of staff?

It's pretty constant. I mean, it's like text. I, I suck at like Slack and all those things. So it's text is like best for me on all those things. I hate emailing. I got like PTSD from the emailing days in my private equity time. So I'm like a terrible— I mean, I'm probably like my average response time is probably like a week on emails.

Because you have so much PTSD.

Yeah. I mean, it's just like I just get too many emails now too. You probably know this, but like as you increase in your reach, prominence, perceived level of success, whatever it is, the amount of people that want things from you increases. And it's really hard to triage that and manage all of that. And so I'm just bad now with email just because my email inbox is a bit of a mess. I have an EA that helps a lot with that, but it's still overwhelming.

And how did you get Tim Cook, Apple CEO, as your mentor?

So I mean, this is a pretty funny story just because it's a perfect example of some of the stuff I talk about with engineered serendipity or expanding your luck surface area. I got started working in 2014. So I had just graduated from Stanford and I was starting at this private equity fund. And I knew that I was going to work long hours. I knew that my days were going to start and I was basically going to just be there into the late hours of the evening. It was like 80 to 100-hour weeks was going to be the standard. And I really wanted to keep up my fitness habit because I had played baseball in college. That was a big part of my life. I didn't want to just lose that. And so what I knew was that that meant I had to go to the gym really, really early in the morning because I wasn't going to be able to reliably go after work. So I started showing up at the Equinox in Palo Alto at 4:45 in the morning where they would open the doors just before 5. And basically there was this crew of 5 to 8 people that would show up every single morning at that time. And you didn't really like know who— you didn't like ask and like network with these people, but you'd see them every single morning and talk to them in the gym and talk to them in the locker room, whatever. So 6 months goes by, it's the same people. So you're kind of like, they're friends. And then one morning someone comes up to me and I was just talking to this gentleman and I walk away and then someone comes up to me and he's like, hey, do you know who that is? I was like, no, who is that? It's the guy that I work out with. He's like, that's Tim Cook, the CEO of Apple. And I was just like, oh. I was like, oh shit, because I'd been talking to this guy for 6 months and probably been saying dumb things, not thinking about it. I had no idea that he was like—

Oh, you never— wow.

'Cause I wasn't in tech. I wasn't in tech and he wasn't— now he's one of the most famous people in the business world. At the time, he was like the new— this is 2014, so he was the new-ish CEO of Apple and you don't look the same in the gym as you do when you're on stage doing the keynotes for Apple, so I didn't know who he was and so then after that, But I reached out to him and just asked whether he'd be willing to get together for coffee or breakfast. I was like starting to figure out my career and I made it very clear that I wasn't looking for a job. Like, I wasn't looking for anything from him other than just—

No handouts.

Yeah, it wasn't like I wasn't trying to go work for him at Apple. I wasn't like trying to get him to invest in my startup. I was on a great track and I just wanted to learn from him. We also both shared a real interest in policy and politics. And so I figured that was kind of an interesting entry point. And so he said, yes. We ended up getting together and really just sparked what has become an amazing relationship over the last— I mean, now it's been 10-ish years since we originally met. And he's been a huge player in shaping the trajectory of my life and giving me a lot of confidence to go and jump into new things. When I left private equity, he was a big part of giving me the confidence to go and do that and jumping into new things. So I'm very grateful for it, but a truly, truly lucky encounter.

Did you start talking to Tim? 'Cause it sounds like you talked to a bunch of people in that 5:00 a.m. squad.

Yeah. I mean, it's hard when you're in a small setting with not that many people for a long period of time to not have had some level of interaction with them. It's different if you go to the gym at 9:00 a.m., 8:00 a.m., and there's hundreds of people. It's probably gonna be hard to build any level of depth of connection with them. So that's part of when I say engineering luck or engineering serendipity, It was because it was 4:45 in the morning. There was only 6 people there every single morning at that time.

Yeah.

And so, it's much easier then to build a true relationship, plus signal to them that you're not just some guy, right? They know, oh, this person has been showing up, waking up clearly at 3:45 in the morning every day for the last 6 months. I was no longer just some guy looking to get you to fund my startup or whatever it was. I had signaled over a long period of time certain things about myself and about my character. And so, So as I think about the takeaways for people, it's putting yourself in positions where you can win in that way. It's truly expanding your luck surface area.

I'm just trying to figure out how the conversation might go because I usually go to the gym around 5:00, 5:30. So same players, it is around 8 to 10 people. But I'm like, that's a nice pull-up you're doing over there.

Well, you don't have to be weird about it. If you do that, I guarantee it won't work. I mean, yesterday, I'm here in LA. LA, and I went over to the Equinox and someone stopped me, like had seen some content I'd put out, and we ended up getting into a conversation. And it turns out that he's like building this media company, like sort of like what the Rain Group has done, like media investing, sports, etc., which I'm really interested in. He has a partner in New York, like he's going to fly out, like we'll probably get together. And so, you know, there's just interesting things that happen when you kind of like open yourself up to a little bit of discomfort.

Mmhmm.

And again, it's not to say that like Like for every interaction that I've had that has turned into a great thing, like with Tim or, you know, like potentially with this guy that I just connected with, there's been plenty of awkward ones where you like do have an awkward encounter or the person doesn't like take the doorknob that you offer them to walk through in a conversation. So you have to kind of be exposing yourself to that risk and like the discomfort of getting rejected or having it be weird in order to have the gold on the other side sometimes.

So my takeaway from this one is there's a shared interest thing, right? You know, them talking about, hey, we're doing this and you're interested in that. Or, you know, with Tim, it's like you guys are showing up early. He's like, you have like shared interests and there's like the shared hustle, right? I think that is the thing because sometimes people just don't know what to say.

Yeah, totally. And look, like there's no such thing as a loser who wakes up at 4 a.m. and works out. Just like the reality. Like if you go to the gym at 5 a.m., like there's not really going to be anyone that's losing in life there because it's really freaking hard to do. It's just like You have to set up your entire life around that really in order to do it. It takes a ton of discipline. So that's just a great signaling mechanism in and of itself.

Piggybacking on the Tim Cook story, so he becomes like your mentor-ish figure. I know you don't like to use that word. And so then you go to the Berkshire conference, you go to Omaha, and what happens there?

Yeah. So over the course of the last 10 years, I mean, I've gotten to do some really very interesting and cool experiences and things as a result of my relationship with Tim and friendship. One of them was going to the Berkshire Hathaway conference now twice. So Warren Buffett's annual shareholder meeting. By the way, Warren Buffett is the OG creator. We talk a lot about the creator economy. Warren Buffett's annual shareholder letters, which he's been putting out for the last 40 years, are a perfect example of the leverage that gets created by content. You don't think of Warren Buffett as as a creator, but those letters have created unbelievable value for Berkshire Hathaway above and beyond what it would otherwise be worth as an amalgamation of weird business assets.

Right.

So he, I mean, as a content creator and as creating leverage via putting your ideas out into the world, he's a perfect example. So when I went the first time, I think it was in 2019, and had a chance to meet Warren, which was amazing. And there's a bunch of interesting people in the circle of Warren, right? Bill Gates is on the board there. Had a chance to meet him. And just a lot of interesting people flock to a weird location of Omaha for a weekend.

It's ridiculous.

Yeah, exactly. And he brings so many people together that are smart and winning in whatever their field is. I went back this past year in 2023 and also had an amazing experience. And it's just an incredible weekend. If you haven't been, and you're interested in investing, interested in businesses, it really is like the next couple of years before, you know, Warren or Charlie pass away. It's really worth thinking about going.

The Tim Cook relationship parlayed into a situation where you met some interesting people at the conference and you— so I'm not going to give away the story. The story's for you to tell. But you knew where to sit and something happened.

I mean, this is, again, 2019. We're at the Berkshire Hathaway event and I got there really early because I'm scared of showing up late to this thing that I'm clearly an imposter. I'm not meant to be sitting in this down-low area. The year before, I had actually gone by myself and sat up in the nosebleeds of the bleachers. And so this year I'm down on the floor in the shareholder area, basically the board member area. And I'm sitting there, it's like 45 minutes before the show starts and I see that there's this backstage area. And I walk back there basically because I'm like, this is where the stuff happens. Like, this back car park area, like, where cars are gonna pull in, that's where, like, the real conversations are happening. It's not gonna be out on the stage. Like, the stage is the dog and pony show, but the real stuff, you know, in any situation, like any business meeting, everything, like, there's a place where the, like, the public-facing thing happens, and then there's where the real conversations happen. And so I sort of just figured, like, this back area is where stuff's gonna happen. So I just kinda went and, like, milled around by myself there. and probably looked weird, like, you know, like some kid basically just like walking around. And the like garage, big like bay doors open close to the time when the show starts and like these like SUVs, black, big black SUVs come in, you know, like Warren walks out of like his like side area, you know, there's like Bill Gates coming out of his car, like, like clearly like all of these powerful people, this is like where they're going to congregate and have a conversation. And so I had the opportunity to be in like a hilarious talking circle with Warren Buffett, Bill Gates, Tim. Yeah. And like the most imposter syndrome moment that you can possibly have in your life in one, in one second. Like, still surreal to me to think about it. And yeah, truly like an example of just putting yourself like in the spot where stuff is going to happen, even if you don't belong. You're just like, this is where it's going to be going on.

So I heard based on your story, Tim was really gracious in the way he introduced you. And then you had a key takeaway from this conversation with some of the richest people in the world.

Yeah. I mean, Tim introduced me, which is amazing, and like sort of invited me to come over and meet these folks, which is, again, just like the type of person he is and how amazing he's been as a, as a friend to me. I mean, my takeaway from meeting these folks or anyone else is like everyone's sort of just a normal person. at the end of the day. Warren Buffett, you see on TV and you're so nervous to meet him, and he's sort of like a jolly grandpa. He's got this sort of folksy air to him. He's like, oh, what's your— I asked, what's your favorite steakhouse in Omaha? And he's like, got that. And he's just a normal person when you have a conversation with him. And I think that applies to any incredible person I've ever met. It's just people that have accomplished something incredible at their one craft, but they're still just a normal person. In most cases. And are there jerks out there? Sure, absolutely. But for the most part, it's like genuine people that are just exceptional and have mastered a craft in a single area.

Yeah. There— I remember there's a tweet thread. So you had an interaction with Bill Ackman, and Bill Ackman is another well-known investor. So I never followed up there. It's like, oh, it seems like they're going to meet for lunch, right? And it was because he— I think he retweeted something that you put out. So what happened with that? Because this is another example of you increasing your surface area of luck.

Yeah. I mean, this goes back to November of 2021. I wrote a Twitter thread on paradoxes, sharing a list of some of these interesting paradoxes of life. And 18 or I guess 14 months later, I'm in India and I wake up in the morning and I have a bunch of texts that just say, hey, Bill Ackman shared one of your posts. And I assume, it's like something recent because Twitter, usually things just kind of disappear like after 24 hours with Twitter, it's kind of gone. But he had shared this thing from November 2021 and he said, you know, like a friend shared this with me last week. I think it's great. Everyone should read it. And so I like— I'm big on closed mouths don't get fed, like shoot your shot because nothing, nothing bad comes from that. And so I replied to his tweet and just said, thanks for sharing my thing. We should get lunch in New York sometime on me.

This is an open reply, not a DM.

Open reply.

Yeah.

Um, and I followed him. He follows me back. I send him a DM, follow up on it, and we do end up getting lunch, and he hosts me at his office. We have lunch together. He's amazing, by the way. I don't know how many, like, uh, people have kind of, like, talked about him in a, in a personal setting. I found him to be unbelievably kind, genuine, present. Like, he sat there— normally, like, I would assume someone as powerful and as, um, uh, diverse in the things that he's working on would have to be running in different directions, checking his phone constantly. But everything was kind of off, and he was present in the room and there. And then when it ends, he's on to the next thing, and I imagine he's just as focused and present into that. Um, and then the other thing is just, like, unbelievable capacity to aggregate data, uh, disparate sources of data, aggregate it, take it in, and turn it into a very simple, concise story. Like, that capacity of data in, story out, is such an incredible skill that you see in high performers that Bill has in spades. And the other thing about him, which people know, is he is not afraid to put himself in the arena. And he's had some very public Ls, very, very public Ls in certain cases, but still just puts himself out there with the next thing. And he's willing to continue to do that. And in the aggregate, he's had unbelievable performance and he's a multi-billionaire and incredible investor. But a lot of people would be afraid after taking that one big L. A lot of people would've stepped away. So that's just like, it's a really interesting trait about him. And just like a good— I really experienced him to just have a good heart.

So I want to go into your— going back to your baseball story real quick. This is going back to your childhood.

Okay. Yeah. I mean, I grew up playing baseball. That was my thing. And that was It was what got me into college. I got a scholarship to play at Stanford. And it was really how I tied my whole identity around. And so now, I write a lot about the importance of identity and the importance of identity diversification, because it's really, really challenging when you have an identity taken away from you that you've centered your whole life around. And I've seen tons of athletes, entrepreneurs go through this, that it's a deep, dark place when you have that taken away from you when you haven't diversified your identity. I got hurt my last year at Stanford, hurt my shoulder. I thought I would go play professionally. I was never good enough to make a true career out of it, but it's hard to tell a kid that. In your mind, you sort of need this false confidence almost in order to do well that I definitely had. In hindsight, I obviously can admit this and know this, but I got hurt. And I remember the hardest part about it was calling my dad to tell him that I was not going to be able to play anymore because so much of our relationship growing up had been centered around this one thing. Like we had— he'd gone to all my games, he had supported me, taken me to all my lessons. And I remember calling him and being like really emotional and him saying to me, like, I don't care. I, you know, I'm so— I'm so proud to have supported you and whatever you do next, I'm going to be there to cheer you on, whatever it is. And that was such a powerful unlock for me in life that just like It made me realize the type of father that I wanted to be too, that I just wanted to be that unquestioning cheerleader for my children, for my son, to just be there. And it's true. It has played out in the way my dad has actually operated. I went and ran a marathon a month ago, and my dad surprised me, flew out for it, was there at the finish line. And that's a stupid thing, right?

Yeah.

I'm not getting awards for winning marathons, but he's showing up and he's there. Because he really meant that. That was a core value that was so important to him. And that's how I want to be with my son as he gets older. You know, that unquestioning cheerleader.

What are some other— so, A, that's amazing. B, what are some patterns that you're for sure just going to model from your mom and dad?

Ooh, so many, man. I'm really close with my parents. Let's see. I mean, my dad was one of the most disciplined people that I knew. I would say the thing that I really took away from him was that I always felt like I was included in the why of what he was doing. And what I mean by that is he had to travel a lot. Like, he worked a lot, he traveled a lot, he was gone sometimes. But I always knew why he was doing those things, like why they were important to him, why they were helping him provide for the family, why they were meaningful to him, why they were tied to his purpose. And so that made me feel like I was included in the journey. And I write a lot about the importance of being present and kind of giving your energy to your children during this 10-year stretch where you are the most important thing in their world until they go off and kind of have their own life. And that doesn't always mean you have to be there, right? I'm in LA right now. My son is at home in New York. I've been gone all week.

Yeah.

But as he gets older, when I travel, I want him to know why I'm doing those things, why it's important to me, why I care about it. Because if you don't tell them the why, kids tend to fill it with whatever the worst thing is. Like, oh, my dad just doesn't want to be at my sports game, or my dad doesn't want to be at this recital, or my dad doesn't want to be at these dinners, versus it's because he's working on this thing that he really cares about, because he's providing for the family, whatever it is. And so there's a lot of moms and dads out there that are working 2 jobs. And not, not able to be around as much as they would want to be. But if you include your kid in the why of why you're doing that, to provide for the family, to be there, to give them the life that you want, that's such a powerful thing because then your kid knows that. They don't fill it with the worst thing. They fill it with the great thing that is the truth.

So would he like always sit you down when he's with you in person and tell you the why? Like, how did that look?

Yeah, it was like over dinners when we were all together. He's like, here's what I was working on this week. I was in Jakarta and, you know, I was giving this talk at this the World Bank or whatever it was. And here was what the talk was about. And it was stuff that I didn't necessarily understand. But seeing him get so excited about things he was working on, like that rubs off on you too, that you want to work on meaningful things where you get excited about it the same way he did. So that was really, really powerful for me.

Got it. So that was the rebirth led you to PE. And then I might even argue the real rebirth is in the last 3 or 4 years.

Yeah, this is definitely the real rebirth. I mean, the PE stuff was like I took that job because I wanted to sound successful. There was no character change that led to me taking that job. That job was, I want externally to appear successful. So what do I do? I have to go into either investment banking or go join McKinsey in consulting or go join a hedge fund or a private equity fund. And it works. People do think you're successful and it sounds great. And you're like, oh, I'm a vice president at this firm. and you feel important and you're flying first class and there's all this stuff that like people pat you on the back. But if you're miserable, if you don't enjoy it, if you're not getting energy from it, you're gonna wake up in 50 years and be like, what the hell did I just do with my life? This is the one, you get one, literally you get one chance where you're between 20 and 50 years old to like really work on things you care about or to really feel like it's connected to your purpose, whatever that might be. Your purpose doesn't have to be your job either. Like I often get caught in this trap. It's easy to say like, oh, you should feel so much purpose in the thing you're doing. everyone has that luxury, right? Like, I feel like I have that luxury now where I feel a real purpose with my work. Not everyone has that or can ever hope to have that, but you need to connect your purpose to your work. And if your purpose is providing for your family, as an example, if your purpose is to provide for your children, then have that purpose on your mind when you're going to work and when you're going to do the thing. Because even if you hate the thing you're doing, whatever it is, if you have that connected purpose with it, you're going to have a whole lot more energy showing up to whatever it is on a daily basis. When the purpose is connected, when you're realizing like, okay, I'm going to this job right now because my purpose is providing for my family and that's what I'm doing with this. It allows you to get through, I think, those harder times and those like valleys that life inevitably has when you are connecting to whatever your higher order purpose is.

What do you think your purpose was 4 years ago versus now?

Selfish. I don't know. I mean, I think my purpose prior to having children was like entirely selfish. I've written about this, that, like... I think having a kid is the first time in your entire life that you are not innately selfish. Uh, and my wife might, uh, be angry at me for saying that. Uh, but I think it's true. Like, until you have something that is really a part of you in that way, everything is about yourself, and it's about... Status and prestige and money and all these things that are so just like textureless, right? Like come and go and you chase them your whole life and not find any fulfillment. And I have found just so much meaning since he's been born of feeling like, okay, this is the reason I'm here.

And like the real reason.

Yeah, the real reason. And for both of us, my wife feels the same way. But that, like, that to me is It's really the first time that you have to give up your innate selfishness and feel like, without question, you would dive in front of a car for this thing.

You started angel investing, I believe, off your own balance sheet in 2020 to kinda build your track record?

Yeah, it was like 2017, 2018 I probably made my first angel investment. Um, and, uh, probably had done— I'd probably invested like maybe $300,000 of my own money in early-stage stuff between 2017 in 2021.

Yeah.

Um, yeah.

And what kind of success did you need to have to then say, OK, I'm gonna go raise a $10 million fund?

Fake success. You know, like, on-paper success. Uh, anyone that was a— that was a, uh— and I'm perfectly comfortable saying that.

Yeah.

Anyone that was, like, investing in venture, uh, from, like, 2017 to 2020, if your paper markups didn't look good, you were, like, terribly bad at investing. You were bad, yeah. Basically, if you were getting into anything that was a good founder, they were then going and raising big markups from all the big funds who were just like— there was so much money flooding into it. So I had a good paper track record during that period. It will remain to be seen if it will be a great actual track record during that period. I raised my fund, which I'm really excited about, the things that I've invested in because of the timing of it. I raised the fund in 2022. Oh, you did. So the fund is getting deployed into a much better market where prices Prices have come down. That was just luck. I wasn't like, hey, this is the time to raise the fund. I just happened to raise the fund in 2022. If I had raised it a year earlier, it would be in a lot of trouble.

On the back end of 2021?

It was like early, mid-2022.

So you knew it was—

Yeah, I mean, it was like—

Shit was getting bad.

Yeah, when I closed it was when the market started to pull back. So the second half of that fund will be deployed into probably at least 20%, 30% lower valuations. But like, you know, if you were a 2020 or 2021 fund vintage in venture, it's going to be really, really hard to have a good return because you deployed a lot of your fund into like the highest, most bubbly peak market in history at, you know, where interest rates were zero.

I'm curious. I mean, so this, this is going into the PE stuff a little bit and I want to come back to this, but I could never— like, I would imagine this is my, my guess working in PE, you got to be super detail-oriented. You got to be willing to grind it out, which you are willing to grind it out. But also you're like a creator too. So for me, I don't know if I could work in PE because it requires— I don't know, it's like the detail-oriented piece gets to me.

Yeah, I mean, you'd be— this was how I was, by the way. So I was like, I was a good analyst. I would say I was a good analyst. I like— I'll send this clip to some of my old colleagues and they'll tell me if I was a good analyst or not. I was a good analyst. I was not a great analyst. I always sort of knew I would be a better partner than analyst. And that was because as you accelerate in that track and in any track, the job becomes less about detail orientation, modeling, presentations, etc., and more about relationships. And that was what I was actually good at. And so, you know, I was like, I sort of felt like I was getting better at the job as I was getting promoted. Like I was a much better vice president than I was an analyst. And that was my bet on like why I was staying in it was like, I'm going to keep getting better at this and enjoying it more over time. as the job becomes more about things that I actually am good at.

And you're— I think you've thought about this. When I listened to a podcast with someone asking you about your superpower, it seems like you've thought through that. So do you think that's your superpower, really? Relationships?

Yeah, I think relationships and like the ability to connect with different types of people, I would say, is the actual superpower there. I'm not transactional. Like, I just— I don't care enough about money to be transactional, frankly. I sort of figure like I'll make money, I'll figure out ways to make money. I don't care about making like a billion dollars. Like, that just doesn't matter to me. I love people. I love relationships. I love learning from different types of people and different backgrounds, different experiences, whether they're like, quote unquote, successful or not. I don't care. And so I come— it's because I come from like a mixed race. You know, my mom is Indian. I come from a mixed race background. My dad's white. I spent most of my life like figuring out whether I was a jock or a nerd. in baseball locker rooms where you're surrounded by deep South Republicans, but then I was from the Northeast and came from this multicultural household and having to be able to get along with, learn from, experience different types of people with different types of intelligence, with different perspectives on the world, and not try to jam your values down other people's throats. That was formative part of my experience and who I was becoming and who I was. And And that's unique. Like when you meet most people now, like they're trying to jam their values down your throat and it's super annoying. I never wanna be that way. Every politician, that's what they're trying to do. And so like my grounding was in the complete opposite. Like I wanted to learn from different types of people. I believe in true intelligence. There's a quote like, true intelligence is the ability to hold 2 conflicting ideas in your head at once. Like that's what I want. That's what I want to be. So yeah, I would say that is my superpower.

And going back to the fund then, what are you, what are you focused on right now? Because again, this goes back to your superpower, right? You're really good with relationships. And I think you, you aren't focused on any specific vertical, right?

Yeah, it's a generalist fund, technically stage agnostic, although it's going to be mostly pre-seed and seed. You know, with the fund, I'm really focused on companies I can actually help via my platform. So like companies where there's a storytelling element, that they either need to figure out or they need to amplify. And so that will lend itself to certain areas at certain points in time. I think there's really interesting things in environmental technology and biotechnology where you need to create a story before the product really launches into the market. Similar to how you think about Uber, you had to convince the world that they could go get into a stranger's car. And that's a story, right? That's storytelling that needs to be done that convinces people of that prior to the business being able to be a success. And I think there's a lot of businesses out there that are like that, that haven't quite figured out that they do need to do that. And I have developed over a long period of time a lot of systems of how to do that well and how to, you know, how to do that effectively, both as an individual and as a business.

And your deal flow. So I'm just trying to like some of the deals I've gotten into, I'm just like, oh, it looks like a really interesting company. I'm going to either reach out to them or if they seem like they're a little cold, I might try to get them on the podcast and then ask them afterwards if I can invest. How are you sourcing your deals?

Mostly through super smart investors. So my model with the fund was, it's just going to be me. I don't have a big team going out and doing deal sourcing for me. And so I'm going to tie in some of the smartest people in the world into my fund. So I basically went out when I raised the fund and went to the smartest venture investors in the world that I could possibly reach, a lot of whom you'd know, like big big, well-known GPs at these enormous funds and had them personally or through their fund invest in my fund, small checks. And what that did was it tied in sources of deal flow where they know exactly what I can be useful for. And when there's situations where those things come up, I'm getting them, they're reaching out to me. And usually what that means for me is it's pre-vetted deal flow. That doesn't mean that I do every deal. That doesn't mean that every deal they do is good, but it's pre-vetted. Founders Fund is not doing, you know, just any deal, right? Like they do a few deals a year right now. So if I'm seeing something through them, that is— there's some level of like signaling that comes with that that is different than just like someone DMing me out of the blue. So I'm relying on some of that as like the, the kind of like upfront vetting of a deal before I spend time and look at it.

Got it. I mean, you play baseball, so like what's Sahil's like strike zone for, for swinging on a deal?

I mean, it needs to be like someone that is, I would say, like has exhibited resilience in their career from a founder perspective. I have a tough time with the like truly green founder that hasn't had the like big failure yet. I think that that's like a tough model. You don't see a whole ton of founder success stories where that was the archetype of like the founder that had never failed. Every now and then, you know, I guess Mark Zuckerberg with Facebook is probably like a big, big example.

Mmhmm.

But most of them had had the like public failure, then they launched the thing. They'd had to get up back off the mat. So I think about that a lot with founders. And then I really just want to find people who are focused on the 30-plus-year vision of what they're building. In 2020, 2021, you found a lot of people that were focused on the, oh, we can go raise the markup and we'll do this and Tiger's going to invest in the next round or whatever. That was what it was and they were getting excited about that. And unfortunately, I did invest in a few things like that because I fell into the FOMO and the trap. But that never works out. Like, if you're focused on the next year or 2 years and you're not thinking about what the 10-year vision is of what you're building, it's a long road to a venture-scale outcome no matter what, right? Like, even the best outcomes, it's a long, long, long road and you're gonna have big failures along the way. So like, getting people that are in for that and that want, that really care about the mission of what they're driving is probably the most important thing.

I mean, there's a Charlie Munger quote, right? Show me the incentive and I'll show you the outcome. And you just, I mean, with venture, it's just like, oh, I'm sure you had all these conversations like, yeah, you know, we're just looking to raise the next round. It's like, how about you look like— how about you look to make money?

Yeah. And that was, that was, that was rare in 2021, right? Like no one had a plan to make money and now everyone has to. You can't even raise a round if you don't have a plan to get to profitability. And that changed on a dime. I mean, that changed in like 6 months. All of a sudden every deck had to have unit economics, had to have like contribution margin, had to have path to profitability. And if you didn't have one, I mean, Paul Graham has been writing about this for the last 20 years. Paul Graham has this piece, I think it's called Default Alive, Default Dead or something, about a business that is default alive. It has a clear path as it grows to actually making money so that it doesn't have to rely on funding markets. And the businesses that have that path are going to succeed and going to do well, and the ones that don't are not, unless they have some crazy thing that's a piece— like an Elon Musk-backed company where he can go raise infinite amounts of money in perpetuity because people just want to be a part of it, which no one really has, right? Like that's N of 1.

Yep. By the way, what do you mean by N of 1 when you say that?

N of 1, like, you know, sample size of 1. He's the only person in the world that can do that.

Got it. So, I'm gonna rattle off— we're gonna— the way we're gonna wrap this, I'm gonna rattle off a couple of philosophies over here. First, I think one of the— I'm paraphrasing here but, you know, the imposter syndrome piece is a good thing.

Mm-hmm.

What's your thought? What are your thoughts on it?

Yeah, I think imposter syndrome, at least for me, is a signal that you're pushing yourself to grow. Like, it's a signal when you feel imposter syndrome, you're inherently like pushing yourself beyond the boundaries of what you believe your current capability stack is. And I view that as a good thing. That's like, okay, now I'm pushing myself beyond that boundary where I feel uncomfortable and I need to figure out the, like, what the thing that I need to get better at, the thing I need to learn so that I don't feel like an imposter doing this anymore. So, I've always reframed that as a positive and it's been a helpful reframe for me.

Love it. Now, there are 2 types of luck. What are they?

4 types of luck.

4 types of luck now. The last time I heard you on a pod, it was 2.

Okay, I love it. Yeah. So, there's this guy, Dr. James Austin is his name. He was a neurologist. And basically, he hypothesized there are 4 types of luck. So, the first type is blind luck. That's like, you know, random chance events of the universe, acts of God, winning the lottery, etc. Second type of luck is luck from motion. That's like you're creating, you know, that's like what happened to me at the gym at 4:45. Like you're hustling, you're grinding, creating luck that way. Third type is luck from awareness. That's like you develop a level of expertise around something so that you're good at spotting luck. You're good at seeing it as it kind of comes around a corner. You can identify the lucky opportunities. And then the fourth type of luck is luck from uniqueness, which is like the idea that your weird hobbies, eccentricities, et cetera, actually attract luck to you. Like people come to you with the lucky things.

Sounds like you can develop the 2 through 4.

Yeah, the idea is that like the beginning of your life is governed by the first one, like where you're born, who you're born to, etc. Entirely blind luck, you can't control it. And then as you progress in your life, the other 3 come into play. So like number 2, you know, luck from motion, is sort of like the early hustle years of your career, like working really hard, Neil, like all of that stuff. Type 3 is like as you develop expertise, and then Type 4 is like you're truly unique and you like own an individual area or craft.

I'll give you a clip right here. How do you get luckier?

I mean, there's so many ways to get luckier. You have to, you have to expand your luck surface area. That is the key to all of this stuff, is like choose the path that has the wider and larger luck surface area. And that's by putting yourself out there into the world. You can't get lucky sitting at home watching TV.

Doing this podcast, doing your newsletter, all those things.

Meeting people, talking to people, experiencing things, sending more cold emails and cold DMs thoughtfully, not just like blanket copy and paste. All of those things are great for expanding your luck surface area.

You've said that friction creates growth. Yeah.

I think that we are generally in a world where, like, friction has been taken out of everything. Like, technology has removed friction from our daily life. Um, and at some point along the way, I think you realize that friction also creates meaning, and friction creates the experiences that you remember. Um, and so you need to figure out ways to actually embrace inserting friction back into your life.

You have a life dinner with your wife?

Yeah. That's a funny topic that it gets like— people get really riled up about that on the internet. This was like an idea that came originally from, I think, an investor named Brad Feld had written about it in like an essay maybe many years ago that I picked it up from. Basically, the idea is that like after you have kids in particular, life gets pretty chaotic and it gets increasingly difficult to find the time to sit down with your partner And actually spend time thinking about, talking about your goals, dreams, aspirations, what's working, what's not working, all of those things. Because you have chaos in your daily life, your kids screaming, crying, all this different stuff is happening. You're running around to different events, whatever it is. And so taking the time, the life dinner is the idea that once a month you have a date on the calendar when you sit down and you talk about these things. There's an And you're having a dinner, but there's an agenda. You're talking about your goals, you're talking about what has worked the last month, what are your challenges, what are the opportunities, how is your relationship growing, how are your businesses, professional aspirations growing? It's taking the time and making sure there's an actual forcing function to have those conversations once a month. People take this in a negative direction on the internet when you talk about it because they say, oh, if you need a schedule on your dinner to do that, your relationship's bound to fail. And I think that's ridiculous. that's actually not the point. The point is to make sure that you do it once a month. If you get to do it every day, I'm happy for you, great. But with one newborn in the house, that's a little bit crazy. We do not get to do that every day. We go on a lot of walks and we talk about things here and there, but really having a substantive hour-long conversation every day, yeah, right, good luck. And so having that forcing function on the calendar, and honestly, before you have kids, I think it's a great thing that people should do with their partners, with girlfriends, boyfriends, partners, whatever. We have found a lot of value in it.

I mean, to your point, I find it kind of crazy because like people are like, oh, like business and people are different. But it's like, no, business is about people and a relationship is about people too. So, it's what's wrong with like systematizing it a little bit, right?

Yeah, it's also just growth. You can't just like assume that a relationship is going to just be strong over long periods of time if you don't work at it. And anyone that thinks that it's going to just happen by itself, Relationships are work, and unless you're willing to do the work along the way, you're gonna have massive issues that have just like boiled up under the surface without you thinking about it, without you doing it, or, you know, like working towards it. And so, you know, there's like the idea of like complementarity is much more important than compatibility in relationships, and we always focus on compatibility.

Yeah.

Like, am I compatible with this person? The reality is you need to be complementary with the person over long periods of time. And so making sure you're talking about those weaknesses and strengths and where you feel like you're growing or developing and where you feel like you need the other person to fill your gap. I mean, relationships are not 50/50 and they can't be at all times. If my wife— if I get home after this trip and my wife is going to be drained from having taken care of our son for a few days, she can't possibly be expected to give 50% to meet me halfway when I get home. I need to be ready to do 90 and she's going to go 10. And then later it might be that I'm exhausted and I can only give 10 and she needs to go 90. But unless we have the conversations and the communication skills to know that and to be able to communicate that to one another, we're gonna be completely lost.

Is it like, uh, it's like Batman and Robin and sometimes you guys have to switch roles?

Yeah, exactly, exactly. Like someone has to be the superhero and someone has to be the sidekick at different points in time.

Love it. There's another post. Yeah, but, uh, so, so, okay. Okay. I do want to talk about— I have a bunch of lines to rattle off in a little bit, but let's talk about your health stack because you're still pretty fit. You take it pretty seriously. So, what's in the health and fitness stack?

Oh, let's see. So, I'm kind of crazy about this stuff. So, on a daily basis, I do my cold plunge in the morning first thing, 39 degrees for 3 to 5 minutes every single morning right when I get out of bed. So, that's It's like, yeah, it's on my deck. So we have a deck off of our master bedroom that has my sauna and my cold plunge next to it. So I get in there first thing in the morning. That's like at 4:30-ish in the morning. It's miserable, it sucks, I hate it, but then it's amazing as soon as I get out. In the evening, I do my sauna every evening. That's when I do like a bunch of reading and stuff in there, which is great 'cause you can't bring your phone in 'cause it overheats. So like just sort of you and your thoughts. And then during the days, basically now I do like running training. I just went and ran a marathon. I had never run before in my life until, like, March of this year. Picked it up, uh, and decided I was gonna run a sub-3-hour marathon. Like, trained like nuts. Ran 1,200 miles over 6 months. Ran the marathon September 10th. Did it. Ran it in 2:57:31, which was great. Um, and I do that plus, uh, like a 4- to 5-day-a-week lifting thing. Um, have built out a home gym, have the whole thing.

You doing the whole zone 2, 3 hours a week as well?

The Huberman stuff?

Yeah.

Uh, I do— yeah, I probably do. do several hours of zone 2 a week just in my running because of a bunch of easy runs. But look, I think that there's levels to fitness stuff. And most people, what they need to do is just move their body for 30 minutes a day. And going and listening to Huberman Lab and thinking that there's a million complicated things that you need to do if you haven't just started moving around for 30 minutes a day is probably not super beneficial. I think it's great to be educated, But just go move around a little bit and that'll be a good start. And so I try to share that. I mean, when I talk about my own regimens and my own routines, I try to share what is the easiest version of this that you can do, that anyone can do.

The cold plunge you have, it's literally called the Cold Plunge, right?

Yeah, I think it's now called the Plunge, but yeah, it's the Cold Plunge.

How about the sauna?

It's from that same company actually.

Oh, really?

Yeah, they're releasing a sauna. I think it's in beta now. They sent me one. It's fantastic.

That's one of the perks of being a creator.

Yeah, exactly. I mean, like, you know, I've probably sold a bunch of cold plungers. I do like a video in it every single morning on Instagram. And they're awesome. And the product is great. Like, it's just lasted. They have a great warranty. They take care of you.

You probably get a lot of engagement, both positive and negative, too.

Yeah. Yeah. I mean, there's always like anytime you're doing anything that, you know, involves being shirtless, like there's always going to be haters on it. Yeah, absolutely. It drives the rage click for sure.

All right, cool. What is your definition of wealth? What's the real definition of wealth?

Of wealth? Look, I'm writing a book on this, so people will have to buy my book to get my full definition. But no, I mean, look, I think that wealth goes well beyond money and that living a truly wealthy life is about a whole lot more than making money along the way. And so, yeah, that's— I will reserve the full definition for the book release.

Go buy the book. And then... meditation comes in different forms. What do you mean by that?

Um, you know, look, I always thought that in order to be a meditator or find mindfulness, I had to sit squatted down and put my hands on and do the whole hour-long meditation. And the reality is I've never been able to do that, but I do feel like I meditate daily while I go on walks. And so finding your... garden. I say that because— so John D. Rockefeller was famous for like milling about his garden doing nothing on a daily basis. One of the most powerful, richest men in the world at the time. He would just like aimlessly walk around his garden on a daily basis, not taking notes, not reading things. There was no podcasts back in the day.

Yep.

He was just thinking and just like meditating on whatever it was during the day. We all need to like find our version of the garden. where we can just kind of escape on a daily basis. And that can be for like 2 minutes. It doesn't have to be hours long, 15 minutes, whatever. But just like finding those little escapes in your daily life are extremely powerful.

Yeah, I tend to think that everything is on a sliding scale. It's like some people over-index on being too productive, some people over-index on maximum meditation, right? But usually it's like a balance.

Yeah, yeah. I mean, if you— and also if you put pressure on yourself that it needs to be the maximum level, you'll never get the beneficial level.

Yep. I think you said you have— I mean, you're mainly talking about balance now. That's like the pillar, right, of your content creation. But then you also have 3 pillars that it sits on. Is that still a thing or no?

Uh, what do you mean?

So, it could be balance, but you could, like— for me, for example, I might talk about, like, you know, buying agencies or running an agency. You know what I mean?

Yeah, I don't really think much about, like, my content pillars anymore. I would say I used to do a lot more of that when I was trying to make sure that I hit on kind of the different pillars on a weekly basis. Now things have just changed for me as things have hit scale, where I'm not as regimented about what I write about and when I write about it. It's much more driven by just what I'm getting excited about on a daily basis.

Got it. I love that.

I do think that having that, if you're starting out, is helpful. Knowing, OK, I'm going to write about markets, I'm going to write about investing, and I'm going to write about my family and personal experiences. And knowing your kind of 3 so that you can look at, I don't want to be over-indexed into one of the 3. I'm going to try to balance across the 3 of them. It's just a helpful exercise to go through.

I think this is super helpful because I think people should go back and re-listen if they're starting from scratch, they want to create Like this is the playbook to do it. But Sahil, this has been great. What's the best way for people to find you online and to learn about your new book?

Yeah, everything's at sahibloom.com. The fortunate thing about having a weird name is that it's easy to find me. So I think I'm like @sahibloom on every, on every single platform as well.

All right. Thanks so much.

Yeah, thank you.