The Exchanges

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

A 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 volume. 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. 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. He 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 dollars down on the balance she…

AI assessment note: “we started a business about two years ago now called Reflexivity Research.”

Q 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?

A 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 10 bagger. Oh my God, it's back to 200 dollars. 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 go to 1200, maybe it was going to go to 800. But if you had sold at 600 and taken your six X, done okay. And so it's very hard to do. It's painful watching it continue to go up after you've 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…

AI assessment note: “If you think about for the individual, both are true in your portfolio.”

Q What are your favorite tools of influential leadership?

A 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? 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'll 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, 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 found in my career is there's a bifu…

AI assessment note: “I would say one of them is doing really small things.”

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

A 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. And so as I started to create the content and build the audience, I was very focused on it. As the audience started to grow, the first implementation of leveraging it was just to get access to private venture capital deals. And the very first fund that I 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 …

AI assessment note: “the very first fund that I ever managed was about a three and a half million dollar”

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

A 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 would say that 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 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 2030 years. And then he sta…

AI assessment note: “playing sports growing up... the military... family influence. So I grew up in a house”

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

A 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. 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 would 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…

AI assessment note: “Having the academic component meet the real world really helped me figure out what”

Q 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?

A 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 Crow, they're all competing, but it's for a common cause. I think that there's an element of that. It makes everyone better. In terms of writing in particular, I think that there is something very clarifying 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. I figured it out. I had to craft this whol…

AI assessment note: “Maybe we're just competitive. I don't know. I do think that there's an element”

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

A 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 I said, 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. 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 can probably tell you which one's going to go viral, but it's just, you'…

AI assessment note: “why don't I take what I've learned and go and figure out how to do this”

Q and wealth management firms moving to Ridgeline gain a decided advantage. That's why customers call it miraculous, game-changing, and an awakening. If that's not how you would describe your investment management tech, request a demo at ridgeline.ai. And now, back to the show. 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?

A 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 the 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 cashflow 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. 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, Coke 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 allo…

AI assessment note: “The way that we're structured today, we have a C corporation.”

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

A You're asking the hard questions. Whatever we do, we're wrong is the conclusion I've come to. So, 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. Think of 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. 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 companie…

AI assessment note: “you basically have to do both. You have to do all the content”

Q So take me through to your time at Facebook. What happened during your time there?

A 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. 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 on Kindle 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 bas…

AI assessment note: “the way I got the job is probably pretty important to understanding my journey”

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

A 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 nineties and early 2000. But the 2010 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 20, 22 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. 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 happened 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 time frame, I think, was very much about access. It was clear we are in the secular bull trend.…

AI assessment note: “And so the audience was used specifically to”