Anthony Pompliano – Building Influence and Capital to Live an Extraordinary Life (EP.430)

Anthony Pompliano is an entrepreneur, media creator, and investor who has built one of the largest audiences of DIY investors. His following canvasses 1.6 million people on X, 560,000 on YouTube, and 260,000 on his daily The Pomp Letter. Anthony created Professional Capital Management, an investment company that builds and invests in early-stage companies by leveraging his audience. He's not alone in his family in creating a following. Pomp's wife Polina writes the popular blog, The Profile, and his brother Joe writes the sports business blog, Huddle Up. Pomp also recently published How to Live an Extraordinary Life, which shares life lessons through letters to his children. Our conversation covers Pomp's passion for competing, leading, and problem-solving, formative business experience at Facebook, translating lessons to build a social media audience, and monetizing that audience through investing. We close touching on his wonderful book with a few anecdotes and lessons to share. Learn More Follow Ted on Twitter at @tseides https://twitter.com/tseides?lang=en or LinkedIn https://www.linkedin.com/in/tedseides/ Subscribe to the mailing list https://capitalallocators.com/ Access Transcript with Premium Membership https://capitalallocators.com/signup Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com https://thepodcastconsultant.com/)

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Ted Seides?

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• 2:12Ted Seides?

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• 2:57Ted Seides?

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• 3:32Ted Seides?

  Hello, I'm Ted Seides, and this is Capital Allocators. This show is an open exploration of the people and process behind capital allocation. Through conversations with leaders in the money game, we learn how these holders of the keys to the kingdom allocate their time and their capital. You can join our mailing list and access premium content at capitalallocators.com.

• 3:59Speaker 01

  All opinions expressed by TED and podcast guests are solely their own opinions and do not reflect the opinion of capital allocators or their firms. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of capital allocators or podcast guests may maintain positions in securities discussed on this podcast.

• 4:18Ted Seides?

  My guest on today's show is Anthony Pompliano, an entrepreneur, media creator, and investor who's built one of the largest audiences of DIY investors. Pomp's following canvases 1.6 million people on X, 560,000 on YouTube, and 260,000 on his daily The Pomp Letter. Anthony created Professional Capital Management, an investment company that builds and invests in early-stage companies by leveraging his audience. He's not alone in his family in creating a following. Pomp's wife, Polina, writes the popular blog, The Profile, and his brother Joe writes the sports business blog, Huddle Up.

• 5:01Ted Seides?

  Pomp also recently published How to Live an Extraordinary Life, which shares life lessons through letters to his children. Our conversation covers Pomp's passion for competing, leading, and problem-solving, formative business experience at Facebook, translating lessons to build a social media audience, and monetizing that audience through investing. We close touching on his wonderful book with a few anecdotes and lessons to share. Before we get going, it's Super Bowl week. And if you detect a slight raspiness in my voice, that's because I spent the last week in nonstop conversations at our Super Bowl, Global Alts in Miami.

• 5:41Ted Seides?

  Our great friends at iConnections and MFA hosted what's become the industry's marquee event: 5,000 participants and 19,000 one-on-one meetings over two days, supplemented by a day of fireside chats with the likes of Stevie Cohen, Brad Gersner, Damon John, Roger Goodell, and many more. On stage, I hosted a reprise of my podcast with the former team at Carnegie Corp. and a discussion of talent with Michael Lovitz and Ali Hamed. Offstage, I recorded a fantastic podcast we'll release soon. The iConnections and MFA teams have led the way in bringing the industry together at scale. Their joining forces this year made Global Alts the best one yet. So this Sunday,

• 6:26Ted Seides?

  whether you're a fan of the Eagles or Taylor Swift, whether you like life in the fast lane or you need to calm down, and after a long night at Global Alts, you prefer a tequila sunrise or to shake it off, you can get everything you want efficiently at Global Alts. Speaking of which, you can even get it for less if you sign up for next year's event now. So after you tune into the Super Bowl, remember to tune in right here on Monday to help us spread the word about all things in the world of capital allocators, including the many pieces of software iConnections is building to add value and serve you all year long. Thanks so much for spreading the word. Please enjoy my conversation with Pomp, Anthony Pomp Liano.

• 7:11Speaker 02

  Anthony, thanks so much for joining me.

• 7:14Speaker 03

  Thanks for having me.

• 7:15Speaker 02

  Why don't you take me back to those most important influences that led to your interest in business entrepreneurship investing?

• 7:22Speaker 03

  I think of business really as three components. One is competition, two is leadership, and the third thing is solving problems. From a business perspective, competition is probably one of the areas that people don't really like to talk about that much because it feels like it's a zero sum, I win, you lose. But I think playing sports growing up, I played football, basketball, and baseball in high school. I was very competitive and felt like that was where I excelled more than maybe in the classroom. And so I don't know if you're born a competitive person or it can be created, but I think that that was probably the biggest thing of just, okay, my body probably won't support me being a professional athlete, but what's the next sport to play? And so I always said that

• 8:03Speaker 03

  investing is the sport for thinkers. And so the competitive nature comes through. On the leadership side, some people gravitate towards being the leader of a team, a school, but also I think the military and the experience I had there cemented a lot of the lessons learned and the impact of leadership. And I think that solving problems really was more of a family influence. So I I grew up in a house where my father had two different careers. For the first half of his career, he worked inside of a corporation like many people, I think of that generation, who picked a company and stayed there for 20, 30 years. And then he started to become more entrepreneurial later in his career. And so you got to see the ups and downs and the stress and the excitement, all of those things. And so naturally you say like, what is business?

• 8:48Speaker 03

  And it's just like solving a problem and okay, what problems are out there that I could go try to solve? And so I think it's those three things coming together really stoked the interest.

• 8:56Speaker 02

  You hear a lot about leadership skills in the military. What was it that you took away?

• 9:01Speaker 03

  I think that there is experiential leadership and then there is more academic leadership. So academic leadership, the military and the army in particular is probably one of the best institutions in the world to teach that stuff. They've really studied it. They've got a lot of real world experimentation of what works and what doesn't. They've had years and years of getting feedback in different environments, in different geographies, with different languages, with different types of people. And so they've really perfected, here is how you manage these teams. How do you motivate these people? All of that academic leadership makes you feel good and gives you some confidence. Like, I think I'm a good leader. You don't actually know until you get the experiential component. And for me, I think that there was maybe two different elements that cemented it. The first was, I was very young.

• 9:45Speaker 03

  I joined the military when I was 17 years old. I signed up with a contract where I was going to go do reserve duty first and then I'd do active duty afterwards. In that contract, it allowed me to go to school and play football. And so I did not do ROTC and so I get deployed when I'm a junior in college. I'm 20 years old. Well, the people around me are not 20. These guys are in their mid to late twenties. They have families, they have mortgages, they have children, they kind of have like life going on. And so if you're in a leadership position at 21 years old, how are you supposed to manage not just people who are older than you, but people who have very different life experiences than you? Having the academic component meet the real world really helped me figure out, what did they teach me that actually is applicable here? And then what are the things that maybe I can ignore for this specific situation?

• 10:30Speaker 03

  You then almost get like a feedback loop because in the military, there is some hierarchical leadership. Terms of I have a certain rank on my chest. You have a different one. Either you're in charge of me or I'm in charge of you. We kind of know what the hierarchy is. When you go back into the business world, the private sector, that doesn't exist as much. And so now you're much more influential leadership. When I went to work at Facebook, I was a product manager and a product manager is a very interesting role at a company like Facebook because technically the engineers don't report to you. The designers don't report to you. The data analytics people don't report to you, but they're all on your team. So they have their own data analytics manager. They have their own engineering manager. They have their own design manager. But you as a product manager was bringing together all these different functions and have the team work together.

• 11:14Speaker 03

  But you don't have any hierarchical leadership capabilities over these people. And so it's all influence. It's all motivation. It's all these softer skill things. And so for me, in a very short period of time, about four or five years, I got a crash course in the academics, the real world, physical hierarchical leadership, and then this more soft skill corporate type leadership. And I'm really thankful for just going through that crash course because it gave me the tools that now when I go into a situation, what is the tool to pull out for this specific environment?

• 11:43Speaker 02

  What are your favorite tools of influential leadership?

• 11:47Speaker 03

  I would say one of them is doing really small things. I'll give you a concrete example, which is here in our office, one day we hired somebody that was new. And two or three days after they started working here, they said to me, hey, can I talk to you for a second? Okay. And they pulled me into my office and I thought I was like at the principal's office. They said, I saw you yesterday loading the dishwasher. And I said, yeah. And they said, why were you doing that? I'm like, because there was dishes in the sink. And they said, oh, don't you think that somebody else should do that? That's not a good use of your time. I said, well, I never really thought about it before, but the fact that you noticed means that other people are talking about it. And maybe it will inspire somebody else to go and take the dishes in the sink and put them in the dishwasher. And so I think there's little things like that that you can do.

• 12:30Speaker 03

  What time you show up, how you dress, you take the trash, especially people who are more senior in an organization, showing that the work's got to get done. And it doesn't matter what role you are, we're all in this together, is a way to implicitly teach the leadership. I show people the right thing to do so they can emulate it. And then I think that There's an element of holding yourself and others to a high standard of excellence. And what I've found in my career is there's a bifurcation with people. When there's a high standard of excellence, some people run away from that. They actually do not want that. They want to just go home at a certain time. They want to have a certain type of lifestyle. They're not ambitious. They don't work hard. But the people you want to be around, they actually aspire. The higher you put the standard of excellence, the harder that they're going to push towards it.

• 13:14Speaker 03

  And so in a weird way, it's kind of like an anti-cell is I was talking to someone that we're recruiting. And I said to her, I don't try to recruit people anymore. I'm not going to try to convince you for this. I've told you how we operate here. You know, deep down, either this is for you or it's not. I don't know you well enough to tell you whether it is or not. I know you can do the job, though. Go think about it for a couple of days and just trust your gut. You'll come back to me and say yes or no. And so that person now has to make a decision. They know where the bar is. They know what the tempo is. They know what the expectations are. Are they scared of it? They probably won't do it. Or are they like, hell, yeah, let's go charge the hill. Those are the people we want. So take me through to your time at Facebook. What happened during your time there?

• 13:55Speaker 03

  Before I went to Facebook, I had built and sold, I put sold in air quotes, two software companies. We raised no outside funding. They basically were as successful of a failure as you could create. Right? They were great in terms of learning everything that you probably shouldn't do, very unscalable. But I think I've always just figured out how to get things across the finish line. And so made a little bit more money than friends who went and got real jobs. But it was very clear to me, hey, I don't know how to do this on a bigger scale with more success. I thought that I had two options. One was to go to business school and pay to get the education. Or I could go and I could get a job somewhere where I could learn through osmosis and get paid to do that. Getting paid versus paying sounded a lot better.

• 14:39Speaker 03

  And the way I got the job is probably pretty important to understanding my journey at Facebook, which is I was talking to a recruiter and he said, would you be a product manager? And I was like, yeah, of course. Sure. And I really didn't know what a product manager was. And so they flew me out there to do the final interviews. And on the way to the airport, I bought Unkindled, The Art of Product Management, which I had Googled around and found that was the best product management book. And I read the full thing on the flight. And the next day I went into the interviews and I basically regurgitated everything I could remember from that book in the interview. And it worked. And so I was showing up as like, hey, I'm probably above average intelligence. I'm really willing to work hard, but I'm not coming here with any prior knowledge. I'm not coming here with bad habits. Mold me, teach me how to do this.

• 15:24Speaker 03

  And so I first started working with a team that was focused on Facebook pages, which is kind of their business product. And I was 25 years old. No one had really worked on this before and they were like, go grow the number of active pages on our platform. Okay. I did not know this about myself at the time, but if you put a metric in front of me and tell me to move it, I become obsessed. Very quickly, we started to move that metric substantially and it was simple things. It's like, why don't we change the color of the button that says create a page from blue to green? I bet you more people click on it. Did they? Yes. What about a darker green or a lighter green? And so you just play this game and you learn that it's a very data driven optimization culture. You could see the real world impact. We were able to create tens of millions of these pages. Those people became advertisers. There was a lot of money that dropped to the bottom line of Facebook and it's very rewarding.

• 16:09Speaker 03

  After that, the most formative thing that I did was I went and I worked directly with Mark Zuckerberg and Sheryl Sandberg. There was a three person team that was assembled. It was a 90 day special project and the whole goal was to help those two individuals grow their following on Facebook. Which, when I tell people that, they always think it sounds a little almost vain, but really in hindsight, they were ahead of this trend of going direct. So some of the comments at the time were, hey, there's a billion and a half people on our platform. I only have nine million followers as Mark Zuckerberg. How do I talk to the audience? And to their credit, they said, we don't want to change the product. We don't want to boost ourselves in the algorithm. We don't want to take over the website. We don't want to friend everyone like MySpace Tom. We want to learn how to do this.

• 16:53Speaker 03

  And for 90 days, we basically just ran a bunch of tests. Put their faces in the photo, take their faces out, say a certain comment, take a different language, put their dog. And you just learn what are the things that work. The reason why that was so formative was one, I got an up close look at two of the best operators in Silicon Valley over the last 20 years. You have these moments where something gets seared in your brain and you're sitting in a room. There's maybe 15 people or so that are meeting with Mark and about halfway through the present. All of a sudden, Mark says, stop, go back a slide. And he starts talking about why one of the screenshots or mockups doesn't have the exact color of Facebook blue. And I remember just being like, did this guy just go from the 10,000 foot?

• 17:36Speaker 03

  What are the strategic elements of the business to what's the pixel? I was just blown away at the level of detail orientation while still having this very important, larger conversation. So I walked out of the meeting and I remember asking my boss saying, hey, that was crazy. Everyone else seemed like that wasn't a big deal. That's the craziest thing I've seen in business. What's up with that? And he said, you have to remember that Mark has more context than everybody else. He remembers when we picked the Facebook color blue. So when he sees something that's off, he's been staring at it for a decade. He knows exactly what it is. And so he cares. It's very important. And the last thing that I learned while being there is the last team I worked on was something called the social good and goodwill team.

• 18:16Speaker 03

  And that team was tasked with a pretty interesting mandate, which was go do good things in the world using the size, scale and advantage that Facebook has. But don't worry about making money. Now, the don't worry about making money part was very antithetical to what Facebook was doing up until that point. But what we were able to launch are things like Amber Alerts on Facebook, voter registration. And so these things that you could see real world impact where you're saying, wait a second, these things are not just having an influence in society, but they're actually platforms where you can communicate certain things. You can have calls to action and you could see even in 2014, 2015, hey, they're important already. But these things are going to become significantly more important moving forward in the future.

• 18:57Speaker 03

  And I think that probably they've blown us away by just how integrated into our lives they've been over the last decade or so.

• 19:03Speaker 02

  How'd you take the lessons of building up Mark and Cheryl's Facebook following to doing it for yourself?

• 19:11Speaker 03

  What you realize is there is a science to this. There is an ability to unpack what you say, how you say it, what the wrapper, the content type, like all these things can definitely move the needle. And if you have the time and the energy and I think curiosity, you can figure out how to grow. When I left that team and was still working at Facebook, there was a lot of other people that were really on Instagram and they were trying to figure out, hey, how do we come over to Facebook? And I became one of the people that they would get funneled to. After doing this for a couple of years, I realized this, I've helped all these other people. I've never done it for myself. And so I went back and I looked one day and in 2016, I think I was slowly almost red pilling myself because I was tweeting things like audience is the new currency, all these different things. I was talking about things I wasn't doing.

• 19:56Speaker 03

  And so in 2017, I said, hey, why don't I take what I've learned and go and figure out how to do this for myself? But if you think about what did I do? I basically just did a lot of scientific investigating of try things, see what works, iterate, try things, just do this over and over again, until you eventually, really you're training your own algorithm. So to the point where today, if you show me three tweets, I could probably tell you which one's going to go viral. But it's just you've been doing it for a decade. You've been tens of thousands of tweets and you're like, okay, maybe we were just doing some of the machine learning stuff before it became cool.

• 20:29Speaker 02

  Where did you take all that in terms of turning it into some form of a business?

• 20:33Speaker 03

  I did it out of necessity, which was when I started investing in 2016, I wasn't living in Silicon Valley anymore. I didn't necessarily have a reputation as an investor. I remember that there was a couple of deals that I tried to get into and I didn't get into them. And I was trying to think about what can I do so that every time I want to invest in a company, it's an automatic yes? And I frankly didn't know what that answer was. But one of the things that was the hypothesis was, well, maybe if I have a big audience and I can go to a founder and I can say, hey, if you take this money, I will be able to help you get the word out about what you're doing. And so that proved to be true over time, but I think that was the driving point.

• 21:13Speaker 03

  And so as I started to create the content and build the audience, I was very focused on it. As the audience... And started to grow, the first implementation of leveraging it was just to get access to private venture capital deals. And in the very first fund that ever managed was about a three and a half million dollar micro VC fund. Maybe the biggest LP externally was like a hundred K. You're me and a buddy and we're like, are we good at this? Do we like doing this? Can we do just enough money to prove that we know what we're doing? But also if we lose the money, people aren't going to be like super pissed at us. You're almost scared to commit to it. By the end of us deploying that fund, it was very clear having the audience is going to be a significant advantage going forward.

• 21:59Speaker 03

  I think we are seed investors in four different unicorns in that fund. Just everything went right. Then from there, I think I started to ask myself, hey, what else can you do when you've got an audience? Where else should you be? And that's where I think we started to put a lot more effort into it.

• 22:13Speaker 02

  When you started thinking through that, what is it that you decided you wanted to do?

• 22:18Speaker 03

  Just focused on Twitter. And so around that time, I probably was like 150,000 followers, give or take. And I started to talk a lot more about Bitcoin. And I always wonder, was it because I thought Bitcoin was something? Or was it because every time I talked about it, it went super viral? And so then I got pulled by the audience. It's probably a little bit of both, frankly. But as I was talking more about Bitcoin in 2018, there were a number of large accounts that got deplatformed. And so my thought process was, I don't really talk about anything that was controversial. I don't talk about politics. But this Bitcoin thing is at an interesting crossroads. I don't know if the government's going to like this or not. It's not the furthest thing in your mind to think one day they just say, hey, let's just take all these accounts off the platform. I was like, I put 18 months of effort into this.

• 23:02Speaker 03

  I've got this big audience now. What if it gets taken away? I've got platform risk. And so I started writing a daily email. And then I started a podcast in August of 2018. And I think 2018 was the year where I really went from the hypothesis of audiences important to, okay, this is going to be very valuable. How do you now start to think about what you're doing as maybe not a business from a monetization standpoint? But think about it from a product standpoint. You would never take platform risk with a product that you want to grow into something big. You would never just focus on all of your effort in one type of content. You would start to do audio, video, text, all these different things that were really business approach, but looking at it from a content perspective.

• 23:45Speaker 02

  So once you've built that following. How did you then use it to lean into the investing side of what you're doing?

• 23:51Speaker 03

  Venture capital, I think that we really went through three eras, if you will. There was the pre 2010 era where friendly venture capital was not cool. It was like Wall Street and hedge funds. And I always joke, you can tell where society is based on movies. And so Wall Street movies dominated the 90s and early 2000s. But the 2010s were dominated by the social network. And so I think that the pre this isn't cool was really where it was almost like a craft. It was like you really had to love the game. You really had to be thoughtful about this. Capital was hard to come by, et cetera. 2010 to call it 2022 was this epic run where the world discovered venture capital as an asset class. A lot of young, smart people started to really spend their time there.

• 24:36Speaker 03

  A lot of founders realized that you could raise a lot of capital. And so it led to this explosion of innovation and technology and all of that. And you had to be in the right asset class at the right time. And so I know a lot of people who they're smart, they work hard. But if you go and you ask them, they're like, hey, man, just like I invested in my friends. I just happen to live in San Francisco in 2012 and all my friends were starting companies. And one of them was named Uber, right? And that worked. And so that 2010 to 2022 timeframe, I think, was very much about access. It was clear we are in this secular bull trend. It is very clear what a good company in terms of like the founder makeup and the early signs, et cetera, looks like versus maybe elsewhere in the country is not necessarily have all the network effects and capital.

• 25:18Speaker 03

  And so the audience was used specifically to get access. I don't think that we had any other advantage than we could show up. And if we wanted to do a deal, we got to do it because we had the audience. There was probably some deal flow advantage where people would send us deals knowing we had the audience, but really it's just again, access. In 2022 is when I realized that, one, I became much less excited about Series A and beyond venture capital as an asset class. A big belief there was QQQ has been compounding at call it 13, 13 and a half, maybe 14% depending on what their starting point over the last decade or so. The average venture fund, if you give them all the credit for their paper marks, 17% a year or something, maybe 18%.

• 26:00Speaker 03

  So if you just average out the numbers, it's about a 400 basis point of outperformance looking over the last decade. And what you gave up is about 12 years of liquidity. Probably a pretty fair trade. If you could stomach the illiquidity, get 400 basis points of outperformance, great. Now, what we've seen over the last decade or so, so much capital come into the market. Maybe there's been an incremental increase in the number of good companies created every year, but it's not kept pace with demand of capital. And so my thought process is those returns will get compressed down. We'll go from 17, maybe we go down to 15, which doesn't sound like a big change, but now what you're going to ask LPs in that Series A or later is, hey, stay illiquid for 12 years for 200 basis points of outperformance. Still, some, that's great and we should do that and others, that's not going to sound as exciting.

• 26:44Speaker 03

  And so, moving forward, I basically said to myself, okay, well, what is the area of venture capital that will always be insulated from market cycles? And I came to the conclusion that the act of creating creates value. So if you go from zero to one, there's nothing here, now we have something. You're creating some value. How much value depends on the company, the sector, all that kind of stuff. But that early stage, pre-seed and seed, will still have opportunities to invest. And now I think there's beginning to get a separation of the best early-stage investors and everybody else. And so you want to continue to play in that area. The other thing that a audience gives you is an advantage, not just in investing, but in building.

• 27:28Speaker 03

  And so in 2022, I started to think a lot about, well, hold on a second. I have this massive audience. Right now, we are giving capital to entrepreneurs and then we are basically helping them grow their business. But it seems like a raw deal if I give you 100K and I own 0.1% of your company and then I go and I create all this value, I'm happy to help you. That's awesome. That's part of my job. But what if maybe we own more of the company? What if we start some of the businesses? And so, over the last three years or so, that's what we've been doing. We've created an investment firm where we've created nine businesses. And the goal really is, how do we create businesses in certain sectors where we have a competitive advantage purely through distribution? And it's not my original idea.

• 28:09Speaker 03

  I stole this from people who are much smarter than me and Logan Paul has done this with drinks and CPG. We've seen Mr. Beast do this over and over again in the food sector. We've seen Ryan Serhant do this in real estate. This is a known model at this point. And just the size of these audiences and the scale at which they're able to do this. But none of those people really are business people. Most of them are focused on what I would consider mass market consumer type products because they have mass market consumer based businesses and audiences. And so we said, well, what if we have a more sophisticated, higher net worth, more corporate and investing crowd? What are some of the businesses that you can create there? And so that's really what we've been focused on is we want to continue to invest in the earliest stages.

• 28:52Speaker 03

  But then also we want to create these businesses and we want to build profitable businesses and continue to do that over and over again. And so far, at least there's early signs of success in doing it.

• 29:01Speaker 02

  What are some of the examples of those businesses that are a good fit? That you can help grow and build with the audience?

• 29:07Speaker 03

  I'll give you a full life cycle of one of these businesses. So we started a business about two years ago now called Reflexivity Research. And in that business, we basically said, okay, there's tons of research that exists in the traditional world. They all have different shiny traps to them. Some of them are really, really smart on certain subjects. Some of them are really good on distribution. Some of them are really good in terms of a high price point and low volumes. Some are high volume, low price point. Go and study all these different businesses. I had helped start a couple of businesses in the crypto space specifically around research, but it was always more as an investor. And so when I looked at those businesses, I said, hey, each one of these has a niche to it.

• 29:47Speaker 03

  But the one niche that no one has gone after yet is providing free research for massive distribution. We're perfectly positioned to pull that off. We don't have to pay to go build all that distribution because we already have it. So why don't we take the right product and put it through that distribution? So that's what we did. We partnered up with a guy, Will Clemente. It was somebody I'd known for a long time. He had all the right values. He worked hard. He was curious and was into a lot of the data and research. And the way that that business basically worked is we put $500,000 down on the balance sheet. And we said, hey, we're going to be partners on this. Let's go build a business. The thesis was right and that was pretty clear early on. But we actually struggled to figure out what is the right monetization method?

• 30:30Speaker 03

  Because if you're going to give away the research for free, who's going to pay you? And so what we began to realize was that the different organizations that were getting covered. They would basically turn the research on and they were willing to pay us for it. And so it became the unique element where you say, okay, hold on a second here. We're doing research, but now you've got to do research on your customers. So again, there's challenges there. There's journalistic things you've got to think through and worry about. There's how do you price it? So long story short, we built it up and about 18 months into the business, business was profitable. But I also, putting my investor hat back on, knew that we were in the start of a Bitcoin crypto bull market.

• 31:12Speaker 03

  And so having been around for a while and seen these cycles play out, I knew I'm holding illiquid equity. Well, if I'm holding a liquid equity, that's not that good in a bull market because I can't sell it when we get to the top. And so I said to myself, I said, well, what if instead we thought of the equity of this business not as equity? We thought of it as economic value that we could invest somewhere. We did a lot of work, figured out a lot of different potential opportunities. And we ended up settling on an opportunity where we sold that research business to a publicly traded company in Canada called DeFi Technologies. They were an asset management firm. They had crypto ETPs in Europe. If you have asset management, you need research, you put those together.

• 31:56Speaker 03

  Not a new original idea, people have been doing that for a long time. But what was unique is that we took 100% of that deal in stock. And so you can imagine people saying to themselves, you're profitable. This sounds like a bad deal. We had made the analysis that we thought that the business we were selling to was significantly undervalued. So now you're playing a game where, hey, I'm an operator, but I'm also an investor. And I'm going to try to walk this line of using things from both sides of my brain to be able to make this decision. We sell a business. The stock went from 51 cents worth a couple hundred million dollar market cap at the time. Today, the stock trades somewhere between $3.30 and $3.50. So what I learned from that whole exercise was we created something from scratch. We solved the problem. We were able to drive revenue.

• 32:41Speaker 03

  We were able to get to profitability, but then we had an economic asset and it wasn't cash. But then we could almost flip from the operator's seat to the investor's seat and say, where do we place this economic value so that it will grow even faster than we could do by ourselves? And so that really, I think, showing that we could start, scale, and sell a business, put me onto this path of, well, why don't we start to do this more? Why don't we try to figure this out more? And can we actually work in reverse? Can we go and say, hey, there's certain types of public companies, they all need X. X doesn't exist yet. We should build it. When we get to a certain point of, you know, whether it's revenue, profitability, whatever, we can then go to these five different companies and we can create an opportunity for one of them to go ahead and buy it. But we want to take 100% stock, so we're actually willing to take a lower price on

• 33:25Speaker 03

  the sale because we're really just making an investment decision. And so my takeaway from this journey over the last three years or so is if you do what everyone else is doing, you get the same return as everybody else. And so you have to do something that is unique, different, weird, frankly. And so my greatest pain in the world now is describing to people when we talk about what we do, because it doesn't sound normal. But so far, it seems to at least be showing signs of getting some traction.

• 33:52Ted Seides?

  We're going to take a quick break in the action to tell you about Brookfield. Brookfield invests in the thing behind the thing behind the next big thing. Their focus across infrastructure, energy, real estate, private equity, and credit is helping to build the backbone of the global economy. Brookfield combines deep operational expertise with disciplined, long-term investing, uncovering value, and partnering alongside clients to shape tomorrow's economy today. Invest in the businesses that shape tomorrow. Learn how you can own what's next at Brookfield.com/own.

• 34:30Speaker 02

  This is not an offer to sell or investment advice. Investing involves risk, including the loss of capital.

• 34:36Ted Seides?

  And now, back to the show.

• 34:39Speaker 02

  So when you bring together this ability to build a company, some venture investing, selling to public markets, what's the structure of, let's say, your liability base?

• 34:50Speaker 03

  Yeah, that's a great question. The way that we're structured today, we have a C corporation we raised from a great group of investors, many that people would know. It's a combination of a couple of funds, but also a number of very successful corporate executives. There's pros and cons to having it in a corporate structure versus maybe a fund or something like that. But I do think that one of the things that we have benefited from and are seeing firsthand is this idea of raising once and then never having to raise again. And so I think people are talking a lot about artificial intelligence and that being a thing. By optimizing these businesses for cash flow, in a way, you're getting non-dilutive fundraising on a quarterly basis. It also allows us to play offensive game of you have a balance sheet.

• 35:34Speaker 03

  That balance sheet can be used to start companies. We could acquire companies. We can invest the capital. I started doing this, I was like, oh my God, this is like something no one's ever known. Like, how am I ever going to learn from anyone? And then very quickly, you're like, wait a minute, Virgin Group, Icon, Koch Industries, Berkshire Hathaway. Actually, there's a ton of these. And I think what people really start to think about is rather than think of it as being an operator and an investor, maybe you just end up being a resource allocator. So you're allocating people, you're allocating money, you're allocating time, but at the end of the day, you're just playing an allocation game. And so it is just a company, which doesn't sound that way when you describe what you do. When you think about the comparisons, I think it's much more of a company than anything else.

• 36:19Speaker 02

  How do you think about the allocation of your time between the investing activities and the brand building, the audience building activities?

• 36:27Speaker 03

  You're asking the hard questions. Whatever we do, we're wrong, is the conclusion I've come to.

• 36:34Speaker 03

  If I spend all my time on building the audience, the businesses will suffer, the investing will suffer. If I spend all my time on the business and investing, then the audience and content suffers and like that's the engine. They give it like a basketball team. The point guard can't play center and the center can't play shooting guard. You need a specific person to do this. You need someone in this role who has a very high capacity for work because you basically have to do both. You have to do all the content and then you also have to be able to run the businesses and invest. And so my day probably looks like a nightmare to most people. I thankfully, I'm having a blast. This is awesome. I can't believe I get to do all this stuff every single day, but you just fit it in. So it's not uncommon for me to record two or three podcasts in a day.

• 37:19Speaker 03

  I write every morning. I'm doing all of the tweeting myself. Then I'm meeting with our teams. I'm evaluating new businesses. I'm managing the investment portfolio, trying to hire people, putting out fires throughout the day. And you look at it and you just say, maybe actually the chaos is why I'm so happy. There's a guy that I met recently who was on SEAL Team Six for 10 years. And he had been at a job and he basically goes into these companies. He has no responsibility to start, but by the time he leaves, everyone reports to him. Finance, operations, everything reports to him. And then he leaves, he goes to the next one. Starts out, nobody even really knows he's there probably. And then by the time he leaves, everyone's reporting to him. And he had done this three times fairly quickly. And I said to him, I said, what's up with that?

• 38:04Speaker 03

  And he said, dude, I'm a SEAL. He's like, no two days were ever the same. I thrive in the uncertainty and the chaos. I need that. I wasn't a Navy SEAL. I was just a little nobody in the infantry. But I think it's very similar is that the uncertainty is actually where I'm most comfortable. If you said to me, design the worst job in the world, it would be a traditional nine to five where I go and I just do the same thing every day. It would drive me crazy. And so when you begin to learn about yourself and what makes you excited and energized, that gives you the confidence to say, I know most people will say, what you're doing is too much or focus on one thing. But you say to yourself, if I only do one thing, I won't be happy.

• 38:49Speaker 03

  And so the challenge in life is like, do what I want to do and be happy. So far it's working. No guarantee it will continue to work, but definitely a different path.

• 38:58Speaker 02

  So on top of all of this, you decided to write a book.

• 39:03Speaker 03

  I need more chaos.

• 39:04Speaker 02

  Talk to me about the impetus of why you put this book together.

• 39:08Speaker 03

  My wife wrote a book and I want to sell one more copy than her.

• 39:14Speaker 03

  No, I think I never thought I would ever write a book. I'm not somebody who thinks in that manner. For all the content I create, it was something that being married to an author, a writer, a journalist, definitely helps. But when my first child was born, my wife really pushed me. She said, hey, you should write a letter to her. And I remember being like, eh, what am I going to say in this? I'm not actually even doing it for the kid. I'm doing it for you at first. And I remember the first one, I went back and I read it. And it's pretty bad. It's like, thank you so much for making me a dad. I'm so excited to hang out with you. And very fluffy and just, I'm almost going through the motions. And frankly, I don't even know if I knew what to say. I was a brand new dad and I was just excited, but I don't know if I'm going to be good at this.

• 39:59Speaker 03

  And so when we had our second kid, I'd written another letter, I think at maybe the one year birthday or something, and we had the second kid. And that's when I said to myself, if I'm going to take the time to write this, impart whatever little knowledge I have to this person so that one day they're going to read this. And so I started writing and for whatever reason, the format of writing letters is very easy to me. And I think there's something about, I was writing to a specific person, especially to my kids, was like very clarifying. And so, I don't know, four or five letters, I was like, hey, you know what? Enjoy this. And I think I started to realize I was getting value out of it for myself. Like it was forcing me to think about things I had learned. It was forcing me to articulate these things. And somewhere between five and 10, I remember saying to myself, I know the hard path is to make this into a book.

• 40:45Speaker 03

  I know I should do that. I know that that is the thing that probably my kids would enjoy. It would be good for other people. I really don't want to do that. And my wife pushed me. I said to myself, if I tell myself I'm going to do it, I may procrastinate, but I will do it. And so I decided to go ahead and write the book. And it's a great forcing function, frankly. I think the biggest thing I took away was, how many times in my life did I ever stop to clarify my thoughts? I just really didn't. That was really the impetus for it was I think that I started to realize, although I'm writing this to my kids, I'm getting a ton of value out of it. And maybe it's a selfish act that I'm pursuing.

• 41:20Speaker 02

  What were some of your favorite letters?

• 41:23Speaker 03

  Well, the one that is definitely most controversial, which I don't think I was surprised, is luck is not real. I don't know when I started to think about this, but I noticed that everyone always says, "I got lucky. Oh, that happened to me. That's bad luck. Oh, that happened to me. That was good luck." And I just remember thinking, what is luck? And so I came to the conclusion, this is fake. Luck is not actually a thing. Probability is something that is repeatable and can be proven and you can measure and a mathematical concept. Luck is actually a psychology concept. And so the best way to describe it is if you and I are walking across the street, we get hit by a bus and we both lose our

• 42:07Speaker 03

  leg. Go to the hospital, somebody shows up and they walk over to your bed and they say, "Hey Ted, what happened?" "I was so unlucky. I was walking across the street. This bus hit me. I lost my leg. Oh my God, my life's ruined." They walk over to my bed and they say, "What happened?" You say, "Oh my God, I was so lucky. I was walking across the street. I got hit by this bus. It only took off my leg. I'm still alive. How lucky am I?" So same exact situation, same outcome, two completely different perspectives determine what is luck. And then I came across some studies that showed you can actually become more lucky by simply telling yourself you are lucky. And so it was like, okay, this is definitely a psychology thing. And so what I realized was luck is actually poison

• 42:46Speaker 03

  because it strips people of agency. So if you constantly rely on luck, if you constantly fall back on good luck, bad luck, what you're saying is that you have no agency. What people normally do is if something doesn't go their way, they don't say, "I should have worked harder. Oh, I could have done this. I could have done this." They say, "Oh, I was unlucky. I'm an unlucky person." If things go their way, they don't want to come off as arrogant. They don't want to say, "I worked hard for that. I earned that." They want to say, oh, I got lucky. So you hear very successful people always do that. And so it's this weird thing where actually the extremes, the people who end up not being successful and the people being very successful, they both want to strip themselves of agency

• 43:29Speaker 03

  in conversation. And so this idea of luck is not real. The funny thing is it's a very real conversation because it then says back to you, you have agency, what you want in life is just on the other side of your actions. And so if you don't want to be fat, don't eat bad food. If you want to have a lot of money, do the things that create a lot of money. So definitely controversial, but probably my favorite one because it required a lot of exploration to come to the conclusion.

• 43:54Speaker 02

  There are a bunch of them that touch on investing. What about bad news? Certainly a case of venture investing. Love to hear your thoughts.

• 44:01Speaker 03

  I learned this at Facebook. Bad news does not get better with time. At Facebook, one of the things that I knew going in was that I was not good at interviewing, identifying, and hiring talent. So I said, I want to get better at this. And at Facebook, the interview process, you go and you talk to three product managers and each one has a specific thing that they are trying to evaluate. So are you a culture fit? Can you do the job? And I forget what the third one is. So when I was at Facebook, I think over a 12-month period, I did something like 120 interviews. My favorite track to be focused on was can you do the job? And so they taught me the way to conduct the interview is basically give a hypothetical situation, a war game through a scenario. And so the scenario I

• 44:46Speaker 03

  would always propose to people is, hey, you're responsible for a product. You go home on Friday afternoon. Everything is working great. You come in on Monday morning and 50% of the traffic to your feature has dropped. What do you do? And I asked this question to probably 100 people, but only once ever did somebody say to me immediately, the first thing I would do is I would alert the team we had a problem. Everyone else would jump to, I would call and look at this dashboard. I would do this. They would get into the war game. But this one person who was very senior, it was so clear. They understood how to work in a team. They understood this idea of bad news doesn't get better with time. And so it is something where bad news, people don't want to share naturally. But if you

• 45:30Speaker 03

  have a mentality of I want to solve problems. Well, people can only solve the problem if you share the news. You tell people there's a problem.

• 45:38Speaker 02

  So you have these two chapters next to each other. Rich people sell too early and buy great assets and hold them forever. How do you hold that cognitive dissonance in your head?

• 45:47Speaker 03

  It's a great paradox of investing is there's many ways up the mountain. And so Jim Simons, very rich man, so is Warren Buffett. Could not have different investing styles. If you think about for the individual, both are true in your portfolio. So there are times where you bought something, you started something and there's a natural life cycle to it. It created a lot of value, but at some point it gets overvalued or market dynamics change or competition changes or whatever. What a lot of people I think will say are their regrets in investing is not actually the opportunities they missed. It's that they give back returns that they had. So I bought something at a hundred dollars. It went to a thousand dollars. I'm a genius. There's a ten bagger. Oh my God, it's back to $200.

• 46:32Speaker 03

  Now I'm only going to make a hundred dollars on this investment. How stupid am I? Well, maybe it was going to go to a thousand, maybe it was going to 1,200, maybe it was going to go to 800. But if you had sold it 600 and taken your 6X, done okay. And so it's very hard to do. It's painful watching it continue to go up after you sold it. But I do think that there is this idea of all the rich people I know at some point sold too early and they were okay with that. They were satisfied. At the same time, all the rich people I know have at least one asset that they bought at some point in their career. And they just said, I'm never selling this. Real estate people, it's usually like commercial real estate. Now Bitcoin investors, I'm going to take the Bitcoin, I'm going to give it to my grandkids. Warren Buffett, buy things and hold them forever. So this is a timeless investing principle.

• 47:17Speaker 03

  But what makes it so difficult is as an investor, you know, both of these things are true. When you bought that thing at a hundred dollars, which bucket does it go in? You may actually, at the same time, in the same portfolio, be pursuing two different strategies. And your job or your challenge is to figure out what's in my bucket of, no matter what happens, what changes, I'm holding forever. And what's in my bucket of when it hits a certain price target or something happens, this is my off-ramp to this investment. To pull this full circle, I used to think that the hardest part of investing was buying the right assets. And I'm now fully convinced that the hardest part of investing is selling correctly. And I'll ask every investor I meet, how do you think about selling?

• 48:02Speaker 03

  And to this day, the only good answers I've ever heard are people who throw their hands up and say, I sell knowing I'm wrong. So maybe I sell half and I hold half. Or I talked to a very well-known early-stage investor and he said, when a company goes public, I break it up into three tranches. First day is liquid, I sell day one. The next third, I sell over the next 18 months. And the last third, I hold forever. And he goes, and if it's a good company, that last third makes me wish that I held the first two. If it's a bad company, I'm glad I sold the first two. And the last third, that's my tax for not knowing. And I thought that was a very good, take the decision-making out of your hands, figure out your system that makes you comfortable, and then just go and make sure you're always disciplined with it. What's interesting is when you're building and investing,

• 48:47Speaker 03

  this doesn't just exist in the investment portfolio. It also exists in the building portfolio. So I always laugh that Google, they just got a little bit more money offered to them early, they would have sold. But man, was it a blessing in disguise that they ended up not selling. And so I do think that there is something about, as long as you are able to take some money off the table and then think structurally, like, most assets over a long period of time should go up, especially in the public markets and liquid assets. Maybe that's what you should do. Maybe just take your principal plus a single turn on the capital or something and then let it go.

• 49:22Speaker 02

  So what's been the impact of the book?

• 49:25Speaker 03

  The single most rewarding part is how many dads have reached out to me and said, I wrote my kid a letter. A couple have even sent me the letters. And you read it. And there was a type of thing where I like show my wife. And I'm like, this guy wrote a four-page letter to his kids because he read the book that I wrote. I think that's been the coolest part. And then the other part that has been rewarding to a degree, but if I ever write a second one, I will be more cognizant of, is every person that works for us weaponizes the book against me.

• 49:57Speaker 03

  They got 65 different life lessons that they selectively choose when to remind me. I put them in the book. There's one that says, take work off your boss's desk. So I have somebody who came to me and they said, I don't want to do my work. I'll take work off your desk. And I said, why don't you do your work first and then you can come over here. So that type of stuff is always fun, but I do think that just knowing that people are reading it and internalizing it is pretty rewarding as well.

• 50:19Speaker 02

  I want to ask you a couple of closing questions, but I have one to ask you before that, which is you mentioned your wife's an author. You write a lot. Your brother writes this great sports blog. What is it in the DNA or the water or both that's perpetuated all this writing in your family?

• 50:34Speaker 03

  Maybe we're just competitive. I don't know. I do think that there's an element of healthy competition in the most loving way of if I figure something out, I want to tell them. If they figure something out, they'll tell me, but also to an element of my brother, he's growing pretty fast on Instagram right now. He won't say it, but I know he's just like, when I pass you, you never kind of hear the end of this. I'm like, maybe we should post a little bit more on Instagram this week, right? I can't let this guy catch me. Go back to sports teams, the best teams, Michael Jordan, Scottie Pippen, Steve Kerr, they're all competing, but it's for a common cause. I think that there's an element of that makes everyone better. In terms of writing in particular, I think that there is something very clarifying.

• 51:19Speaker 03

  You can't be a clear writer if you're not a clear thinker. And so writing is the most selfish thing I do. I think that it's somewhat therapeutic, frankly, but also it really forces me to take all these disparate data points and information, et cetera, and clearly articulate it in a single 750,000 words each morning. When you think of that, everything I do throughout the rest of the day is informed off of that. I can pull ridiculously minute data points and details off the top of my head because I sat down and I wrote them. I did the research and I figured it out. I had to craft this whole thing and then I read it after I wrote it. If you think about my brother, my wife, et cetera, I think that there's an element of that as well. They're learning and the writing is the output.

• 52:04Speaker 03

  And so when you're around people that like to learn, I think you guys all gravitate towards each other. And so there's no one thing. I wish there was a magic water. We'll probably be handing it out to people, but I just think it becomes cultural. And then also there's the competitive aspect. That's probably the more fun part.

• 52:20Speaker 02

  All right, Pomp, got a couple of last questions for you. What's your favorite hobby or activity outside of work and family?

• 52:26Speaker 03

  Reading. I really enjoy sitting and reading physical books. Although I read all week, Twitter and emails and news and all that kind of stuff. The time spent per insight gleaned from a book is still off the charts compared to the noise of the internet. And so it's very enjoyable.

• 52:48Speaker 02

  What's your biggest pet peeve?

• 52:49Speaker 03

  It's probably the intersection of laziness from a work ethic standpoint, a lack of ambition, and a disregard for quality. One of the things that I think I've learned over time is if you think about a professional sports team, the product they put on the field tells you everything you need to know about the ownership and the management team. If you look, usually the teams that are not good are not good for a long time. And they tend to be the owners that are less involved or less enthusiastic. They usually are the owners who've owned the teams for a long time. And so I think about the same thing in professional life of what is the product that an individual is putting on the field?

• 53:33Speaker 03

  Is it something that they're actually proud of? And one of the aspects maybe that I'm most proud of over the last three years or so is when I was thinking about, okay, we have to name the company. There's a lot of names. You could name it after yourself. You could name it after some random thing. You could name it after a place or there's all these heuristics people use. And I remember saying to myself, I just want to think of one word that summarizes everything that I want this company to stand for. And so we named it professional capital management. That is the bar. What time should you come to work? When would a professional come? What should you wear? What would a professional wear? How should you conduct yourself in the meeting? What would a professional do?

• 54:15Speaker 03

  It just became this very clarifying framework. And everyone doesn't have the same idea of what a professional is. But it really focused people on there is a standard of excellence. There is this professionalism. There is this desire to do something different.

• 54:33Speaker 02

  Which two people have had the biggest impact on your professional life?

• 54:36Speaker 03

  On my professional life? Mark Usco and Jason Williams. I met Jason in 2015 or beginning of 2016. Jason was probably the first person I'd ever met that had been very successful from a business perspective, but he was still incredibly down to earth to the point where you could go and get a beer with him for four hours and feel like you were talking to your best friend from high school. And I think that he probably took a bigger bet on me than he was realizing. There was definitely times where I was probably a pain in the ass. But I think he was probably just mature enough to realize sometimes you gotta let young guys run and like, let's see what happens. And so that was really effective.

• 55:21Speaker 03

  And then I think the second one is Mark Usco. And Mark taught me that you get old if you don't hang out with young people. And so he constantly was looking for who are the young people? Who are the people I can hang out with? How do I continue to learn? How do I stay interested in this stuff? The guy takes more notes in meetings than I've ever seen. I used to joke, dude, your hand's gonna fall off. But just, he wants to learn.

• 55:41Speaker 02

  Pump last one. What life lesson of all these you've written about in your book perhaps? Have you learned that you wish you knew a lot earlier in life?

• 55:49Speaker 03

  I learned at 20 years old that we all die. It's very morbid, but there was a specific incident in Iraq. There was somebody who died. It was a very horrific situation. And I remember leaving that day, you're a mess of emotions. You're mad, you're sad, you're confused. You frankly frustrated, probably feel guilty to a degree as well. There's just this whole thing. And I remember I got back to the base and when something like that happens, it's just chaos. And so I remember thinking to myself, What is the lesson I can take away from this? And I came to the conclusion it's that we all die. Today was his day, could have been mine, it's not. But one day it will be.

• 56:31Speaker 03

  And so what can I do tomorrow, the day after, et cetera, to squeeze as much out of life as possible? The greatest blessing of my life, outside of probably being born to the family I was born and the environment I was born, is I learned that at 20. There's a lot of people that don't learn that until literally they're on their deathbed. And so at 20 years old, I think there was this inflection point in my life where I said to myself, there's a different life that I want to lead. Not that I was on some bad path or something, but just I want to get as much out of this as possible and really enjoy it. And so I probably became more optimistic. I became more enthusiastic. I became more excited. I don't know how else people can learn that other than maybe you can read about it, but you probably got to experience something. And it was incredibly valuable.

• 57:16Speaker 02

  Well, Pump, you start every day with a tweet or an X tweet. Today's going to be a great day. Let's get after it relentlessly. And I just want to thank you for sharing just a little ounce of that relentlessness with us.

• 57:27Speaker 03

  Thanks so much for doing this.

• 57:29Ted Seides?

  Thanks for listening to the show. To learn more, hop on our website at capitalallocators.com, where you can join our mailing list, access past shows, learn about our gatherings, and sign up for premium content, including podcast transcripts, my investment portfolio, and a lot more. Have a good one and see you next time.