#1198 Anthony Pompliano Reveals His Investing Secrets

This episode is a special one. I went on a podcast called 'Under The Timfluence' hosted by Tim Luong. We talked about the financial economy, my life, creating content, building business, investing strategies, & much more. Anthony Pompliano shares his journey from army veteran to successful entrepreneur and investor. He emphasizes the importance of surrounding oneself with knowledgeable people and constantly learning new skills. He also discusses the impact of easy money on society and the need to constantly reinvent oneself and make connections across industries. ======================= Pomp writes a daily letter to over 235,000+ investors about business, technology, and finance. He breaks down complex topics into easy-to-understand language while sharing opinions on various aspects of each industry. You can subscribe at https://pomp.substack.com/

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

• 0:02Anthony Pompliano?

  What's up everyone? This is Anthony Pompliano. Many of you know me as Pomp. You're listening to the Pomp Podcast, which is my effort to find the most interesting people in the world and sit with them for hours while I ask questions in an effort to learn. We have no advertisers on this podcast, so it would mean the world to me if you would subscribe to the show on your favorite audio platform, watch episodes on YouTube, and tell your friends and family about the podcast. My goal is to help millions learn from the world's most interesting people. So let's get into today's episode. What's up guys? This episode is a special one. I went on a podcast called Under the Tim Fluence with Tim Wong. And in that conversation, Tim asked me all sorts of interesting questions and I thought that you all would appreciate it. We talked about things in the financial economy.

• 0:47Anthony Pompliano?

  We talked about my life. We talked about how I create so much content, how I think about the internet, building products, building businesses, and much, much more. Here is my appearance on Under the Tim Fluence.

• 1:01Speaker 01

  The action's on the court. And as the official beer sponsor of the NBA, Michelob Ultra is getting fans closer to the game with a chance to win courtside seats, merch, and more. Visit michelobultra.com/courtside to enter. Michelob Ultra Courtside, 26 to 27. No purchase necessary. Open to U.S. residents 21+. Begins on October 1st, 2026 and ends on June 30th, 2027. Multiple entry periods. See official rules at michelobultra.com/courtside for free entry, entry deadlines, prizes, and details.

• 1:28Speaker 02

  Anthony Pompliano runs Pomp Investments. All views of him and the guests on his podcast are solely their opinions and do not reflect the opinions of Pomp Investments. You should not treat any opinion expressed by Pomp or his guests as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his personal opinion. This podcast is for informational purposes only.

• 1:52Anthony Pompliano?

  Awesome. Well, welcome Pomp. So nice to have you. You're super close here in Miami with us in Coconut Grove. So appreciate you coming on the show today.

• 1:59Speaker 02

  Absolutely. Thanks so much.

• 2:00Anthony Pompliano?

  For having me.

• 2:01Speaker 03

  So I want to kind of jump right into it. So I didn't even know you were in the army for how many seven years?

• 2:07Anthony Pompliano?

  Six and a half years.

• 2:08Speaker 03

  Six and a half years. Yeah. Like, how did, what was kind of that, that, you know, your, your story in terms of like, how'd you get into the army and then the, the big pivot into crypto?

• 2:17Anthony Pompliano?

  So I, um, I was in high school, uh, graduated semester early from college, uh, from high school, was going to go to college in kind of the spring of my senior year. Um, ended up not doing that. Instead enrolled in the army, um, signed a contract that would let me go to school and have, uh, kind of army reserve duty until I graduated and then I would go active. Um, and in hindsight, joining the army was probably one of the best things I ever did, right? Uh, I was already pretty disciplined. I was pretty ambitious, you know, all the things that kind of would make you either want to sign up for the army or be successful in the business world, whatever. Uh, but it really kind of hammered home, I think, two things for me. Uh, one is like, there's like this, um, uh, understanding of mortality that comes especially if you get deployed and things like that. And so,

• 2:58Anthony Pompliano?

  uh, at a very young age, it was like, oh shit, I like, I see the end, right? And so, okay, between now and the end, uh, I just want to enjoy my life and, and kind of do all this, you know, really fun, cool stuff. That's fulfilling for me, but like, I'm not confusing that I have forever. And so it really set me on a path to like, just do a lot of things, um, which I'm grateful for. And then the second thing was, uh, it basically showed me just like how much stress you can endure, how hard you can work, um, and kind of how to, in my mind, like operate. And so when you get pushed to the extreme, uh, in these situations, like everything else seems pretty easy. So one of the things that's always funny is like, if you talk to, uh, you know, combat veterans who went to Iraq or Afghanistan over the last, you know, 20 years or so,

• 3:38Anthony Pompliano?

  uh, in the business world, people are like, how, why aren't you stressed? And like, a joke is almost like, well, no one's shooting at me. Right? And so like, it's kind of this weird thing where, uh, once you get to the extreme, anything that doesn't actually put you in that extreme situation seems easier. Now, it doesn't mean that you make all the right decisions, doesn't mean that, you know, you never stressed. It's just like, you have this baseline of, you know, real stress is something else. And so I think that's been a great thing for my career as well.

• 4:03Speaker 03

  That's amazing. So you, you basically had a, a different. You had a different understanding of what stress is for most people. And so what what happened after college? Like, how did you get into where you are today?

• 4:14Anthony Pompliano?

  I went back to school. I tried not to go back actually back to school. My dad was like, hey, get your ass back here. Like, do not try to go and sign a contractor, you know, contract and go back to Iraq or any of that type of stuff. And so I started two businesses. I started one when I was in school. I didn't know what I was doing, you know, made a million mistakes. We basically kind of barely got that across the finish line and ultimately sold it. Second one was a little bit more successful and we're able to kind of really put ourselves in a position where I was started. Okay, like I'm picking this up, right? I'm understanding how do I recruit people? How do I build products? How do I do market research? How do I actually convince people to give me money for, you know, as a customer, things like that?

• 4:52Anthony Pompliano?

  But it was still clear to me that I didn't know how to scale, right? And so it was like, okay, now like I'm not an expert, but at least I can go kind of zero to one and I can kind of get these things off the ground. But how do you scale? How do you build a big business? And so I had this choice to make. I could either go and get an MBA and kind of like pay to get an education. Or I could go and have someone pay me. And so I ended up joining Facebook 2014. I was there for two years and it was like a crash course. It was, you know, again, probably one of the better decisions I made in my career because it just put me in the room with people who are world class at what they did. And nobody like sat me down and was like, here's the curriculum, right? They're basically like, hey, man, you got to provide value around here, right? And so at a, I think I was 25 when I joined at Facebook and they gave me way more responsibility than they probably should have.

• 5:36Anthony Pompliano?

  And so it was kind of like sink or swim, but because you're around these world-class people, you can kind of ask around, you know, the edges for advice on certain things. Or hey, I'm dealing with the situation. How do you think I should handle it? And what you do is you pick up through osmosis. And so like, that was a lesson for me of like, okay, the rest of my career, I always want to be around people who have either done something I want to do. Or I want to be around people who have knowledge that I want. And if I can just pick it up through osmosis by being around them, that is like, you know, learning on steroids. And so I've really been conscious over the years about how do I surround myself with those types of people? Because if you can continue to learn, it's compounding, right? Just like you can compound capital, you can compound knowledge and you just pull away from everyone else because you just have more information.

• 6:16Speaker 03

  Yeah, yeah. So would you say a lot of the skills in terms of in the army, I'm sure you had to build strong discipline, like what you said? And just be a sponge, essentially. That's, that's what you did once you entered the workforce. And then what was the decision for you in terms of like leaving Facebook to start, you know, your own thing?

• 6:33Anthony Pompliano?

  Yeah, so when I left Facebook, I mean, basically, I'd gotten advice early on in my career that was like, you can stay somewhere for 10 years, or you can stay somewhere and get two years of experience five times. Right? And I was like, oh, that's interesting, right? So like, even if you're somewhere 10 years, you may actually only get like 80, 90% of the knowledge in the first two years. They just repeat that over and over again, and you don't actually keep learning.

• 6:54Speaker 03

  Yeah.

• 6:55Anthony Pompliano?

  And so if you look at many of these kind of corporate jobs, usually that is about kind of the tipping point, right? Is if you stay past two years, you're probably staying for, you know, five, seven, 10 years.

• 7:04Speaker 03

  Yeah.

• 7:04Anthony Pompliano?

  If you stay for two years or less, obviously you've moved on to something else. And so I just got to the point where I was kind of antsy. And like, there's a fine balance between being a young person and constantly like grass is greener, you know, and having that antsy feeling just make you want to do something versus sticking with it. But again, in hindsight, I think that was probably the right decision because I'd learned probably, you know, 70, 80% of what I was going to learn from Facebook. I went and I spent a little bit of time at Snapchat as the head of growth, and then eventually started investing full-time. And the investing was really like, I didn't have an idea of another company to start. And so I was like, well, maybe I could just like help other people with their companies, and then I'll get an idea over time and I'll start another business. And then, you know, here we are almost a decade later, and now I'm like, oh, okay, yeah, sure, we have businesses and we kind of do all the operating stuff.

• 7:46Anthony Pompliano?

  But like, I really love investing, and so we keep doing that, you know, kind of in parallel to operating the businesses.

• 7:52Speaker 03

  Got it, got it. And so you started investing, and did you, you didn't start off with your own fund, you worked at a fund?

• 8:02Anthony Pompliano?

  We started a micro VC fund, so myself and my buddy Jason Williams. You know, I mean, like, match made in heaven. We met up one day for a beer. Somebody introduced us. I think it was supposed to be like a 45-minute, you know, 60-minute thing. We were there for like three or four hours. Next thing you know, like, people are calling, where are you guys? You know, the whole thing.

• 8:20Speaker 03

  Yeah.

• 8:21Anthony Pompliano?

  And we just hit it off because I think we both were very ambitious. We both were, worked really hard. We both had some pretty good common sense when it came to business, but we weren't subscribed to like all the bureaucracy and all kind of the bullshit, right? And so, you know, at the time, Jason had this like massive beard. And all this stuff. And so we were like, all right, we can work together, right?

• 8:40Speaker 03

  Yeah.

• 8:40Anthony Pompliano?

  And when we got started, really, it was about a three and a half million dollar fund, maybe 3.3, 3.5 million dollars. And we were going around in the mid Atlantic region, which is basically like Raleigh, North Carolina.

• 8:53Speaker 03

  Yeah.

• 8:53Anthony Pompliano?

  Right. They call like DC to Atlanta, but it's like basically everyone that we could find in middle of North Carolina. And nobody invested more than like 50 or a hundred thousand dollar check. Like, these are all like super small LP checks. They're like doctor, lawyers, like whatever. And you just don't know what you don't know, right? So I was going back and forth between Raleigh and New York City at the time. And there's not a lot of entrepreneurs that are building big companies in Raleigh, North Carolina.

• 9:18Speaker 03

  Yeah.

• 9:18Anthony Pompliano?

  So what I would do is because I had the network from Silicon Valley, everything was remote. So like now this big rise of like all the remote work, I didn't do it because I thought it was cool or because I thought I was the head of the curve. It was just like, if I want to invest in the best companies, I got to find them, right? And so rather than go and try to find the founders, what I did was I knew some of the investors. And so I started calling investors and being like, hey, here's the deals I'm seeing. What are you seeing? And so naturally you call the right people, they have good deal flow, right? You start to get the deal flow yourself.

• 9:44Speaker 03

  Yeah.

• 9:44Anthony Pompliano?

  And so in that first fund, we invested in a number of businesses that absolutely exploded in value. And so that was kind of an initial start to building a track record. The critique of that fund was it's a three and a half million dollar fund. You two have no infrastructure, you, you know, you basically are investors, you're not actually asset managers, which is kind of a nuance. And so that's when we then did a partnership with Morgan Creek Capital and Mark Yusko. And they had real infrastructure, right? They had a big team, they had kind of, we used to joke all the time, they have a compliance team, they have a finance team, right? Like all these things that go into actually building a business versus just managing kind of a single fund.

• 10:19Speaker 03

  Yeah.

• 10:19Anthony Pompliano?

  And, you know, got a crash course of education there as well.

• 10:22Speaker 03

  That's amazing. And so when did you pivot from basically, obviously you run your own family office now? But from that to like, you know, putting content online, writing on Twitter,

• 10:32Anthony Pompliano?

  Yeah.

• 10:32Speaker 03

  Your YouTube.

• 10:33Anthony Pompliano?

  So, um, you know, when I was at Facebook, uh, I was into this very kind of unique position where, uh, I started out, I was the product manager running the growth team for Facebook pages, which way to think about that is like the page, uh, product is the top of the funnel for advertisers. So you have to have a page to become an advertiser. Facebook wants advertisers, right? So naturally they want you to have a page because that's one step towards becoming an advertiser. Who gets a page? Small businesses, uh, influencers, celebrities, uh, you know, corporations and brands, right? And so what would happen is I kept getting introduced because of being in that position to all these people who had audiences elsewhere. So one of the first people that I actually got introduced to was the Instagram account Fuck Jerry.

• 11:15Anthony Pompliano?

  And so, uh, Elliot, Ellie, um, they were building out Fuck Jerry on Instagram and they were like, what should we be doing on Facebook? And so as I got to meet some of these people, it was like, oh, you have to figure out how to use Facebook to build an audience.

• 11:27Speaker 03

  Yeah.

• 11:27Anthony Pompliano?

  And so just seeing it over and over and over again, having access to the data, understanding how the algorithm works, et cetera. Like you just build a base of knowledge. When I left that team, it was to go join, uh, kind of a very small team that worked directly with Mark Zuckerberg and Sheryl Sandberg, tell them to do the same exact thing. I didn't go to Facebook and be like, oh, I'm going to figure out how to help people build audiences on Facebook or any of that stuff. It's just kind of, you know, you, you find your way there. And so with, uh, Mark and Sheryl, what they wanted to do was basically they were very, very early. They don't, people don't give them enough credit, but they were early to going direct. They realized, hey, we have a billion people on Facebook. Mark had like nine million followers. He's like, they're, they're like, how do I reach my own users, right? And he didn't want to do like Tom from MySpace where he like forced everyone to, uh, become his friend.

• 12:10Speaker 03

  Yeah.

• 12:11Anthony Pompliano?

  Like, I mean, Tom's cool, right? But like, but Mark, I think it was like, hey, I don't want to do that.

• 12:14Speaker 03

  Yeah.

• 12:15Anthony Pompliano?

  Um, he also didn't want to really like change the product too much. Like, you know, we now see kind of all these controversies around these platforms that are like boosting somebody's content or down, uh, ranking somebody's content. He didn't want to change the product. So he's like, I want to learn how as a user to reach more people, right? Now he's Mark Zuckerberg, so people see his content, they, they know who he is.

• 12:32Speaker 03

  Yeah.

• 12:32Anthony Pompliano?

  Um, and so it was a lot of testing, right? It was like, hey, if you post a photo, uh, what's In the photo versus what's not and how popular is that? So, you know, I don't think I'm sharing anything that that would be controversial. But like if he has his dog in his photo, people like that photo, right? And so like, okay, like, how do we incorporate that into the content? Just like any other brand or content team would do.

• 12:53Speaker 03

  Yeah.

• 12:53Anthony Pompliano?

  This back to 2014, though, right? So he's really doing it. So when I got to investing, what I realized was two things. One, if you want deal flow, people got to know who you are. If you want to win deals, people got to know who you are, right? Like, what do you stand for? Who are you? Like, all that brand building type stuff. And two was I had no audience. I helped all these other people build an audience, but I'd never done it for myself. And so the easiest platform for me was Twitter, because I could basically just, you know, type something on my phone and go. And so in 2017, I literally just worked my ass off, right? And it sounds weird to say like, oh, on Twitter, you worked your ass off? But I literally was tweeting like 20, 30 times a day. I was doing everything I possibly could to build that audience. And I went from about 2,000 followers to 100,000. And that's when I was like, all right, there's something here. And I kept, and I tweeted it multiple times throughout the year.

• 13:38Anthony Pompliano?

  Like, I was very clear with people. Audience is the new currency. If you have an audience, you have massive leverage in this kind of new world we're moving into. And so over a five-year period, I went, you know, Twitter, email, podcast, YouTube, etc. And what I learned was not only is audience the new currency, but also it's the fastest path to learning. Because you can put an idea out there, and Twitter specifically, like, it don't take a lot for some, you know, troll or critic or whatever to immediately say like, hey, that's wrong. Great, why? Right, explain. And so you get to test ideas very, very quickly, and the feedback loop is kind of tight. And so what you can do is you can iterate closer and closer to the truth. So if you can do something that isn't really that big of a time investment, you get the leverage from the audience and you get the learning. It's like a grand slam.

• 14:23Anthony Pompliano?

  And so I just started to do that, kind of coinciding with the investing. And, you know, I never thought it would turn into what it is now, but happy that it did.

• 14:31Speaker 03

  That's amazing. And so you started off with Twitter, you moved on to email. So you write a daily email, right? And then on top of that, what made you want to start the podcast and YouTube? Was it just to expand your audience or?

• 14:43Anthony Pompliano?

  No, there's no master plan. Like, the podcast is a great story. There's two guys. Jason Yanowitz and Mike Ippolito, they run a company now called Blockworks. They came to me and they were like, hey, you should have a podcast. And this was after they had like literally harassed me to come speak at one of their events in New York City. And it was one of those things where like, do you ever have somebody who like reaches out to you so many times? Like you don't even know how you met them or why or what. But I finally was like, if you got, if I come to one of your events, will you guys stop texting me?

• 15:10Speaker 03

  Yeah.

• 15:10Anthony Pompliano?

  Right?

• 15:11Speaker 03

  I know, I know Jason, by the way.

• 15:12Anthony Pompliano?

  Okay. All right. So like you already know, right? And so they were like, yes, of course. Like, yeah, that's what we want. It's come to the event.

• 15:17Speaker 03

  Yeah.

• 15:17Anthony Pompliano?

  So I went and then they like kept emailing me and all stuff and they actually sent it to me recently. My first email back to them was, what is this? What do you guys do? Like, like they were putting on the events, but I didn't understand the business, whatever.

• 15:30Speaker 03

  Yeah.

• 15:30Anthony Pompliano?

  And so long story short, they were like, you should have a podcast. I was like, I don't even know what a podcast is. They're like, don't worry. We know how to do a podcast. And so like, you know, great lesson for young people was, I didn't know this. They had no clue about a podcast, right? They just knew that if they could work with me somehow, that would be great for them and for me to be a win-win.

• 15:46Speaker 03

  Yep.

• 15:46Anthony Pompliano?

  And so when I was like, all right, fine. I'll do a podcast, but like, I don't want to do anything. I don't want to deal with equipment. I don't want to deal with setup, take down, like anything. I'll find a guest. I just want to show up in the room, talk, leave. That's it. They had gone, I think to Gary Vaynerchuk's guy who was running all the podcasting stuff. And they'd basically DM'd him and been like, hey, we're gonna start a podcast. What equipment do we need?

• 16:08Speaker 03

  Figure it out on the go.

• 16:09Anthony Pompliano?

  Yeah. So one, figure it out on the go, but also two, like, that's a pretty good person to ask, right? And that person probably wants to help other people figure it out and kind of help young people, et cetera. So like that story, I think is really kind of a great lesson of just, you know, one, find people that you can kind of work together with and it's a win-win situation. Two is like, you just got to kind of figure it out, right? And then if you go back and you watch the first podcast episodes, it is cringe worthy, right? Like we had a microphone and there was basically like a spit cover or whatever, like whatever it is. And it's so big that the way that the camera's shooting, you can't see my face. Like it's like, I might as well just have like a curtain in front of me, right? And so you watch it and you're like, man, how dumb were we, right? And it's like funny to laugh at now because you learn over time, all this stuff.

• 16:51Anthony Pompliano?

  But it was the willingness to basically do it and just put it out there. Like, who cares? Let's see what happens, right? And so very quickly, you start to learn, hey, how do you get better at this? You talk to people and stuff and then, you know, it kind of takes a life of its own. But I actually don't think this would have been successful if I had approached it from like a top down. I am going to build this media business and here's, we're gonna have a podcast, we're gonna have that like, that's just not how I work. And so I think the organic kind of bottoms up approach was much better and ended up actually building something that was valuable.

• 17:20Speaker 03

  Gotcha, gotcha. So you're, you're very like, I'm just gonna do a bunch of things, test it, see what works and, and keep, keep throwing stuff at the wall and then when something works, you know, double down.

• 17:30Anthony Pompliano?

  Most people who work very closely with me, uh, it is, uh, if you ask them, they probably would say it's my gift and my curse, right? Um, over the weekend, uh, somebody was DMing me, uh, about Twitter subscriptions. And so like my reaction is on Saturday, right? Was like literally within 20 minutes I had set up and then I was just like, hey, I'm, I'm starting a subscription thing. I'm gonna do a 30 day test. Let's see what happens. Right? And so like the violence of action of like idea execute, uh, can be very, very powerful. It also sometimes can get you in situations where you're like, should I, maybe I should have thought through that more, right? And so you gotta understand that it's like a positive and a negative. But for me, it is, uh, uh, I have learned to do it as experiments rather than like fully commit.

• 18:13Anthony Pompliano?

  So in maybe 10 years ago, I would have been like, oh, Twitter subscriptions. Uh, I am going to launch Twitter subscriptions. Here's exactly what I'm gonna do every single week. Here's exactly, you know, uh, what the value is to you, like very rigid kind of approach. And guess what would end up happening is it probably wouldn't end up being sustainable because I would sign up to do too much or, or whatever.

• 18:31Speaker 03

  Yeah.

• 18:31Anthony Pompliano?

  Instead I said, I'm turning on subscriptions. I'm gonna do it for 30 days. I'm not promising anything. I'm just gonna test and see kind of what works. Couple of people subscribe. I start talking to them. Hey, what would be valuable? How does this work? Where, uh, what are you missing in, you know, content that you would rather, uh, have, like all this stuff? And like already in four or five days, we've iterated away to like, oh, people are like, oh, this is not only valuable, but it's so valuable. I'm gonna go tell my friends.

• 18:54Speaker 03

  Yeah.

• 18:54Anthony Pompliano?

  Something here, right? Now, how big can it get? Is it worth doing past the 30 days? We'll see. But I think that's like a great example of, you know, there's the top down approach. I call that like the boardroom approach is next year, we are gonna go do international expansion. I'm very much take what I call like the street approach, which is no, it's like, we gotta go get this product out into people's hands. And so I'm a big fan of kind of nineties and two thousands hip hop. And if you go back and you look at, you know, whether it's the Jay-Z's of the world, the 50 cents, whatever, like they literally just flooded the streets with mixtapes. Like that was the beginning, right? And so like, what, like, what is the mixtape strategy in the digital world today? You have to flood the streets with content or product to be able to build hype and grab attention.

• 19:39Anthony Pompliano?

  Then you take that attention and you capture the value. Like that is what people have been doing for decades, if not centuries. It's just that in the digital world, you can't use all of the old analog playbooks, but you can take the essence of what they did and apply it to the digital world. And so no different than like burning your CD, putting it in a, you know, a plastic wrapper and then going out into the streets and handing it out to try to build hype. Well, what's the version on the internet is probably iterating quickly to try to find things at work and then try to scale those, right?

• 20:06Speaker 03

  Yeah, yeah. So how big is your team right now?

• 20:09Anthony Pompliano?

  Yeah, um, the team is kind of split across a bunch of different things. So we have like the operating businesses. I would say there, uh, there's more than 50 employees across all the different businesses. On the investing side, uh, it's just me and my brothers, uh, which, you know, for better or worse, uh, has been highly effective in terms of small team and able to kind of deploy, uh, capital as we see fit.

• 20:30Speaker 03

  Two brothers or how?

• 20:31Anthony Pompliano?

  I have four brothers.

• 20:32Speaker 03

  Oh, wow.

• 20:32Anthony Pompliano?

  Yeah. So not all of them are involved day to day, but, um, there's me and one brother specifically that like every single day are doing stuff. The other ones, uh, if you were to ask them, they'd tell you they invest only in the good deals.

• 20:46Anthony Pompliano?

  So we do the work and they, they invest in the good deals. But when, when you think about, uh, on the content specifically, we basically have three people, right? We have, uh, two people who do audio and video, and then we have one person who helps with like partnerships, marketing, uh, sponsorship events, things like that. So those three people plus me is like not a very big team, right? Now they are supplemented with, uh, you know, we have a, a director of finance. We have somebody on the team who handles all the operational stuff. Like we have all these other kind of roles that really are kind of my family office and they go across all of our companies. But on content specifically, it's two, you know, audio, video, and then that kind of partnerships person. In today's day and age, you could probably do this without anybody. For me, though, just given how much, you know, I've got other things going on. I need people who are fully dedicated and focused on it. And so having a team makes sense.

• 21:31Speaker 03

  Got it. So you have your content team, operating businesses, and then investing side.

• 21:35Anthony Pompliano?

  Yeah, when I was younger, I would do everything myself. Like, again, blessing and a curse, I got a lot of shit done. But how long can you do that?

• 21:42Speaker 03

  Exactly.

• 21:42Anthony Pompliano?

  We burn out, right? Yes. And so I think over time, I've gotten much better about how do I go find people who are great at what they do? And delegate, right, which is like a classic problem for a lot of entrepreneurs. But also, how do I go find people that I'm able to work with? Where they actually may be better at it than I am, right? So, for example, with video editing, a lot of people would be surprised. I don't actually see most of the videos, the final edit, before they go out. Now, if you were to talk to, you know, a Mr. Beast or somebody like that, like, they obsess over every single little detail.

• 22:14Speaker 03

  Yeah.

• 22:14Anthony Pompliano?

  Right? But that is the core of their business. For me, the content is something we do, but it's not, you know, we're not hanging our hat on it. If content was the biggest opportunity, then I would just shut everything else down.

• 22:24Speaker 03

  Yeah.

• 22:24Anthony Pompliano?

  Right? It's one thing that we do, and so I trust the people who edit the videos, and they do that. Every once in a while, they do something, I'm like, hey, let's not do that anymore, whatever. But I think that understanding where to invest your time and energy is really important. But also understanding, like, what's the ROI on that investment? And so if I were to spend three hours interviewing, or reviewing every single, you know, kind of, cut of every single video, what are we going to do? Get an extra 10,000 views?

• 22:53Speaker 03

  Yep.

• 22:53Anthony Pompliano?

  Like, what does that mean in terms of, you know, impact on the businesses, impact on the investments, in terms of revenue? Like, it's immaterial compared to everything else.

• 23:00Speaker 03

  Yeah.

• 23:01Anthony Pompliano?

  And so when I look at it that way, it's like, all right, the team, put them in a position to be successful. Give them, you know, kind of the green light, and then just go and focus on the areas where maybe you don't have somebody that you can kind of trust to do that stuff and go do that stuff.

• 23:13Speaker 03

  Yeah. Do you have an operator running your operating business on a day-to-day basis, or is that you right now?

• 23:19Anthony Pompliano?

  Uh, each business is different. So if you were to think through some of these, I also think that not only is the structure different. So there's some businesses, like we have a recruiting business that we own, that recruiting business we purchased. There's two guys, they run it. They're the original kind of founder and his first hire, who's now going to come into, you know, his right hand man role. They're fantastic. Like, we do a call once a week for 30 minutes. They ask when they need help, right? I give them ideas if I've got ideas, but for the most part, like, they run that business, they do a great job doing it. I don't really need to be involved. And like, I always joke with them, I say, hey, if I was running the recruiting business, the recruiting business is going to zero, right? Like, I'm not the guy to be able to go and do that. And so, understanding that they're better at it than I am, I can just

• 24:04Anthony Pompliano?

  kind of give them. We have a business in the research space, a business called Reflexivity Research, where we basically create research, and then we sell it to hedge funds, family offices, etc. That business is fairly new, it's less than a year old. I've been very, very involved in helping get it off the ground. I'm not doing the research, right? The research analysts know how to do the research. Well, actually, what we need is to go to market. How do we actually get this into people's hands? I have the connections, people know who I am, you know, I understand how to structure the deals, like, I'll be very involved. If I'm still that involved a year from now, something went wrong, right? And so, like, where we are in the sequence of a business is really important. And then on the media side, like, for better or worse, this podcast doesn't get recorded if you don't do it, right? Same for me, is if I don't do the content, it doesn't get recorded. And so, it's actually a bad business

• 24:47Anthony Pompliano?

  from like a day-to-day, you know, kind of operational standpoint, because like being a doctor or a lawyer, you gotta touch the patient, you gotta touch the customer. If you don't do it, you don't. So if you go and, Robert Kiyosaki has this, like, something he calls a cash flow quadrant, I think, which is like a really old book. But he basically talks about like, you're, you can be an employee, you can basically be like a small business owner, you, or I'm sorry, you can be an employee, you can be self-employed, you can be a business owner, you can be an investor. And he's like, most people operate on the left side of that quadrant, but they think, oh, I went from employee to a business owner, right? Like, like, I'm killing it. He's like, no, you don't own a business, you were self-employed, you just got yourself a job, right? You have to touch every client, you have to do the work yourself. Really, what you want to do is you want to move into either the business

• 25:31Anthony Pompliano?

  owner role, where you're not running the business day-to-day, or into the investor role, right? And so, that's where kind of true wealth ends up getting built. It's just hard for people to do that, because the easy things to do are the self-employed opportunities, where they're like, oh, I'll just do it. It's great to get off the ground, zero to one. How do you scale? You got to get into those other areas.

• 25:49Speaker 03

  Yeah, got it. So what other operating businesses do you have aside from the recruiting firm and then the research firm?

• 25:57Anthony Pompliano?

  Yeah, so we have all kinds of different businesses. I think minority positions, like over 200 businesses, right? Now, those businesses are everything from what I would consider like kind of small business stuff to venture capital investments where we own like 1% of the business, right?

• 26:13Speaker 03

  So it's like- That's from your fund that you invest in, okay.

• 26:16Anthony Pompliano?

  I had the original fund, then did the bigger funds. Now, out of the family office, made a bunch of investments, right? And so those are, you know, yes, we own part of the business, but like we're not involved day to day in operating or anything like that. In terms of the core operating businesses, I would say that there's really kind of three different things that we have. We've got the media business. We've got a holding company of various products and services in the crypto industry. There's a job marketplace. There's training programs for corporations. There's research. There's the recruiting firm, etc. So like all the things that are not necessarily tech products, but are needed for an industry to thrive. We've been able to put them together in a really interesting way where we can go to a company and say, hey, we can help you find people. We can train those people. We can form those people, right?

• 27:00Anthony Pompliano?

  We can kind of do all these things that you're going to need, but you want to outsource rather than build internally. So that holding company kind of houses all of that. And then we've got another one that we've recently just started where we're trying to go and actually acquire all sorts of different businesses outside of the tech industry. We'll see how it goes, but I'm pretty excited about it because when you go and you look at a lot of these businesses, like take the industrial sector as an example, you are absolutely selling painkillers, not vitamins. People need these products, right? And they're going to buy the products whether you exist or you don't. And so really it comes down to how do you execute? It's all about execution risk. And why I like that is because most of the competitors, you know, there's one business that we've been looking at that involves a call center. And now that call center is in the brokerage business.

• 27:44Anthony Pompliano?

  So when I see that business, I'm like, man, how antiquated is it that people are calling into a call center? People are looking things up on their computer and then they're calling the people back with pricing. Why don't you automate it, right? And so that's a perfect example where like that execution has already built a pretty big business. But if you can upgrade with technology, can you execute even better? And then you can actually beat the competitors because you offer lower pricing, et cetera. So can you go into these sectors where most of the people I talk to about this in the tech industry? They're like, dude, what are you doing, right? Like, why would you ever want to go play in a space where there's physical items, right? Or dealing with, you know, people who don't understand technology or whatever. It's like, yes, that is a challenge, but part of it is like, there's very little competition.

• 28:26Anthony Pompliano?

  You know, if you kind of subscribe to the teal view of the world of like, you know, competitions for losers. Like maybe actually going to compete in these markets where nobody else is really looking or no one's excited is actually the opportunity that is kind of largest. And so we're kind of putting that together now and trying to figure out how to do it in a sustainable, scalable way. But that's the one I'm probably the most excited about because if we get it right, we can just run wild throughout, you know, that whole industry.

• 28:50Speaker 03

  Got it, got it. And so for your crypto, holding firm, I know you said that there's a lot of different pieces in that. You know, you have your crypto, you know, training program as well, the job placement program. Who, who runs and manages that, that day to day? And like, how, how do you guys get clients?

• 29:06Anthony Pompliano?

  Yeah, so I run the kind of holding company, if you will. And that entails a couple of different products. And we have people who are like the person responsible for something, right? We've, we've got somebody who's the director of education on the training program, does a fantastic job. He's involved day to day, talking to potential customers. He's actually helping to deliver the content, et cetera. Then some of the other businesses have, you know, like a GM or CEO or whatever. When you look at that product specifically, or that kind of holding company, what's interesting about it is it's all actually really focused on people. So when you think about people in the non crypto world, there's tons of products out there, right? But actually, if you look at what we did is we basically just took the market and said, well, what if we just all specialize this stuff for this crypto industry?

• 29:51Anthony Pompliano?

  And so we've helped over 2,000 people get a job, right? And so when I think about like, what gets me up in the morning? It's like, do you know how impactful it is to get one person a job?

• 30:00Speaker 03

  Yep.

• 30:00Anthony Pompliano?

  Right? They go from, maybe they had a job. But they don't like it, or maybe they had a job and they weren't getting paid enough, right? Or for whatever reason, to get them a new job that they like and that they feel like they're getting paid, you know, uh, kind of the value that they deserve is incredibly impactful for one person's life. We've done that 2,000 times in about two and a half years.

• 30:18Speaker 03

  Wow.

• 30:18Anthony Pompliano?

  Right? And so that's like two to three people a day that were helping get these jobs. And so when you look at that, you start looking at the average salary and also like, it's meaningful.

• 30:26Speaker 03

  Yeah.

• 30:26Anthony Pompliano?

  Right? And so when you, when you kind of take that approach, it's like, man, what else would be more fun to work on? Then having this impact on people's lives. Now I tend to always look at this stuff from the perspective of like, I actually don't care that much about what are the financial results on a day to day basis? Like if we help people get these jobs, keep them informed, keep them trained, do all these things, the money will come. Right? And so it's really, really focusing on just like, how do we help the companies and the people find each other? And kind of make that match. And if we do that correctly, everything takes care of itself.

• 30:56Speaker 03

  So in terms of like your, your week to week, how do you, how do you find time to, you know, balance health, your relationship, work, business? I figure that's, that's a, that's quite a lot of, of just stuff you're, you're involved in.

• 31:10Anthony Pompliano?

  I have no hobbies. Like this is what I fucking love doing, right?

• 31:13Speaker 03

  Business, yeah.

• 31:14Anthony Pompliano?

  And so, um, if you think about, uh, a single day, um, one of, one of the things I take great pride in is if you were to talk to most people who have ever worked with me, they'll be like, dude, I thought I worked hard. Like that motherfucker is unstoppable, right? And it's just because over time I've built up this capacity, uh, for immense amount of work in a single day. And so to give you a, a kind of a, a glimpse at it, I pretty much will go from eight to four, back to back, no breaks, right? And it's 30 minute meetings, just back, back, back, back, whatever. Now, I don't necessarily want to do that, but we have so much stuff going on and I'm needed in certain things until I can get them kind of delegated to other people that I'll do that multiple days a week, right? Then I'll basically, I'll go home, I'll take like a little break, right? Maybe an hour or so.

• 31:57Anthony Pompliano?

  And then I'm just right back at it until about eight o'clock at night. And so when you look at that, like, man, that's a lot. But it's like, yeah, but what else would I do? Like this is so much fun.

• 32:05Speaker 03

  Yeah.

• 32:05Anthony Pompliano?

  Right? And it's like, a lot of people are sitting in their corporate job and they're like, man, I can't wait to get out of here and go to the golf course. I'm like, dude, I don't give a fuck about that. Like, I can't wait to get on this next call, right? I did a call yesterday with somebody for an hour. It's a friend of mine and I literally told him when I got on the call, I was like, dude, I woke up this morning and I was like, I get to fucking talk to him today. Right? And it's just like, like that to me was going to the golf course, that was going to whatever. And so if you just know that about yourself, like double down on it. And then the other thing that I do every single day is I make sure that I read. And so at eight o'clock, I pretty much shut whatever I'm doing down. The team will laugh because every once in a while I'll sneak in a Slack message here or there, right? But I, I, I just fundamentally believe that like I am happiest when I get to read every day.

• 32:49Anthony Pompliano?

  And so if I work out in the morning, do the work and then I read at night, it's the perfect day. So I just do that over and over and over again. And what you do is like, it's, it's like building a muscle, right? I always joke that like, everyone's like, oh, I want to work hard, like cool practice. Yeah. Right? Like get started, actually do it. And so when you do that, it does two things. One, you do build the muscle memory and you're able to just have a higher capacity for work than most people. But two is like, there's a lot of people that I work with that I think, uh, whether they work at our businesses or they work, you know, in the business we've invested in or whatever. They're just like, damn, like I can't complain, right? How do you complain when the person who is leading an organization is willing to do so much work? Or willing to do things that, uh, they're asking you to do. And so it goes back to like the military, right?

• 33:32Anthony Pompliano?

  Is, uh, if you're a, uh, NCO or an officer, you eat last, right? Everyone else is, is kind of taken care of first. You're willing to always do the hard work, right? You're willing to always do the things that you're asking these other people to do. And you probably have done it. And so like one of the things in, in the military that, you know, kind of gets, uh, dramatized by the movies and stuff is like, you know, go clean the bathrooms in these war zones where there's everything that needs to be burnt. People are like, why would I ever do that? It's like, well, guess what? Like when other people were younger, that's what they did, right? So they've been there, they've done that stuff, like they understand how it works. And so I think it's just like, um, we, we have a couple of crises in America. One is a financial education crisis, one's a hard work crisis and one's a leadership crisis, right?

• 34:17Anthony Pompliano?

  And you can actually solve two of the three of those by simply just working hard and, and actually leading by example. And so what ends up being interesting about that is there's lots and lots of people who love to complain, like we have absolutely become a nation of complainers, right? People just get on the internet and they're just bitching about anything that possibly goes wrong in their life. I tend to think that actually we need to shift back to being a nation of competitors. And if you think about, you know, think of like the people that came before us. All right, I was reading a book recently about the McMillan family, which is the McMillan and Cargill's created Cargill Inc. Cargill is, you know, one of the largest privately held companies in America today. They came from Ireland in like the early 1800s, McMillan family, and they literally showed

• 35:01Anthony Pompliano?

  up in Canada and somebody was like, you have 200 acres. Here is a map. Go out into the wilderness and go build your house. Like dude, that's fucking hard. Yeah. By the way, don't get into any conflict and die. Don't get eaten by wild animals, right? Like, like all this shit. Like dude, we wake up and we fucking have a supercomputer in our hands within 10 seconds and we could press buttons and like breakfast could show up, right? Like, I mean, it's like the most cake life of all time. And so if you think about that, like the positive view is we live in the most prosperous, safest time in human history. The downside of that is damn is it easy to be lazy, right? So easy. And so if we just bring back this idea of like, if you keep in context what the

• 35:45Anthony Pompliano?

  people before us had to do and you realize how fortunate we are, like it is your responsibility to work hard. It is your responsibility to do these things. And if you do that, not only will you be a good, uh, kind of, I think, example for the people you work with or, or, uh, people who look up to you, but also you'll pass those traits on to your kids, to your grandkids, et cetera. And we can kind of keep staying in the right path in life rather than, you know, once you become a nation of complainers, complainers get fed. Like that's the other thing. And if you go back in history and you study it, the, uh, kind of early warning sign of socialism is complaining. Cause people complain, they complain, they complain, they complain. And then what ends up happening is the people in charge are like, dude, we're tired of hearing these people complain, just give them shit.

• 36:27Anthony Pompliano?

  Right? And when you give them shit, it turns into socialism. Take away the incentive, you can completely screw up entire economies and nations by doing that. And so it's like, hey, we're at a fork in the road. Stop complaining, start competing, and let's get on with it.

• 36:40Speaker 03

  Yeah. And I feel like it's, it's tough to shift that, right? Because social media, like what you said, has made it so easy to complain that now you would have to rewire the whole.

• 36:50Anthony Pompliano?

  You culturally, it has to become unpopular to complain.

• 36:55Speaker 01

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• 37:23Anthony Pompliano?

  Right? And, you know, I have this saying I say in private that probably not politically correct, but whatever. But it's like, if you think about cancel culture, cancel culture was a zero interest rate phenomenon. I don't see a lot of people getting canceled right now, right? All of a sudden, economy gets a little rocky. People go, oh shit, I didn't make sure I got a job. I gotta like, take care of my family. What's on my balance sheet? Right? Like, people get, like, it's back to, like, serious time.

• 37:45Speaker 03

  Yes.

• 37:46Anthony Pompliano?

  And so when you have easy money flowing around, like, people are bored. Like, it's literally a product of boredom, right? People are on the internet, they're arguing with each other, they're acting like idiots, all across the economy. They're literally just, like, throwing money out the window, right? Because it's easy money. And so when you return back to tighter financial conditions, all that nonsense goes away. And so I do think that the pendulum is kind of swinging back. I don't know if we'll fully swing from complaining to competing, but if we can even get to equilibrium and reduce some of the complaining, great, right? And so then we can kind of get back into it. And like, nothing will refocus someone more than a threat to their economic status.

• 38:22Speaker 03

  Yep.

• 38:22Anthony Pompliano?

  So if you own a business and easy money's happening, what do you do? You get distracted. You start doing all kinds of crazy stuff, right? The second you think a recession's coming, people are like, oh shit, take that golf session off my calendar. I gotta make sure I got customers, right? And so I think that's kind of, as a society... Society, we're getting back into that a little bit. And you see politicians kind of changing their language a little bit. You see the large banks and asset managers, but you also see individuals. All of a sudden, now it's a lot about, you know, hey, let's focus. Let's get more serious again because the tighter financial conditions, you know, kind of forced them to do that.

• 38:53Speaker 03

  Yeah, people just get too comfortable when it's when money is easy, right?

• 38:56Anthony Pompliano?

  So, yeah, and this is not a new thing, right? I mean, it's been a lesson throughout history that we've seen over and over and over again. But it's also a thing where you confuse being smart for being, you know, fortunate with good timing. And it's like, you know, in 2021, if you got rich, and I put that in air quotes, because like whatever that is means for you. Was it because you did anything or was it literally just because you happened to just live through 2021? Right? And so if it is the latter, then you just got to very quickly become comfortable with the fact that like, oh, maybe I'm not actually some genius. And I should just stick to the fundamental principles, right? There's a lot of people running around, they thought they had all kinds of, you know, really unique investing strategies only to lose a bunch of money in 2022.

• 39:40Anthony Pompliano?

  And so it's like, yeah, you can press out on the risk curve, you can, you know, become distracted, you can do all this stuff. But at the end of the day, it's not about how much money can you make in a short period of time? It's how much money can you make and keep over decades, right? And I think that there's a whole generation of people who are just relearning that lesson.

• 39:56Speaker 03

  So what are your thoughts right now on the economy in terms of 2023 and what's going to happen in 2024?

• 40:02Anthony Pompliano?

  I think long term, like the writing's on the wall, right? Regardless of what anyone does in the short term, like we have too much debt. We're going to continue to debase the currency. It will financially ruin the bottom 50% of the population. Taxes will continue to increase to try to feed the beast of the national kind of government. And I think that America unfortunately has continued over this, you know, 250, 275 year run. Built this amazing thing, but we now have become a nation of complainers, right? Like TikTok is the best example, in my opinion, right? I subscribe to the view that TikTok is a massive threat and is being used in a way that has the potential to program kids and do all this kind of stuff, right?

• 40:48Anthony Pompliano?

  How we got there, though, is very heavily debated, and I think there's a part of that conversation that's missing. TikTok was successful because they built a better product. Nobody held a gun to the 14-year-old kid's head and said, "You have to use TikTok."

• 41:02Speaker 03

  Correct.

• 41:02Anthony Pompliano?

  No, they downloaded an app because their friend told them, and they were like, "This is fucking awesome." Right? Look at these dumb videos.

• 41:11Anthony Pompliano?

  I'm addicted, and I'm gonna keep opening this app, right? Now, why did TikTok do that and Facebook or Google or Twitter or whoever not do it? We got outcompeted in the market. And so, from my view of the world, the way to correct that problem in the future is we have to win from an innovation standpoint. We cannot let other countries or other companies from other countries outcompete us. We need to be a nation of competitors. And so, if you take that view, you then can kind of go all throughout society and realize competition is a huge, huge part of this. And so, another example that's kind of more tangible for most people is the Bright Line here in South Florida. So, for those that don't know, Bright Line, it's not exactly a high-speed rail, but it's probably the closest thing we have to high-speed rail

• 41:56Anthony Pompliano?

  in the United States. It was bought by a bunch of investors in like 2007, 2008, maybe, I think. And in March of 2023, it was the first month in the history of the Bright Line that they basically turned a profit, right? Now, if you think of a train, there's not a goddamn train in America that's profitable, right? Without subsidies from the government and, you know, all the things that have to happen. At one point during 2020, the MTA thought they were gonna go bankrupt in New York City with the subway because they had bonds that they had to pay out, and there was no fares because everyone's locked at home, right? Like, these are not great businesses historically, and they've really struggled financially because they're just big projects, they're expensive, they use a lot of debt, all this stuff. Now, why is the Bright Line profitable?

• 42:40Anthony Pompliano?

  In March of 2022, they had 70,000 rides. In March of 2023, they had 170,000 rides. Now, some of that is just demographic tailwinds, right? In terms of more people are comfortable using a train than they used to be. Some of that is a migration to South Florida, so you get more people. Just coming here. Some of that actually has to do with the Miami Heat are good, right? So people from these other places are coming down, they're coming to whether it's Marlins games, whether it is Miami Heat games, whatever, right? Some of it is because it's freaking nice. So I wrote it the other day for the first time and I literally text my wife and I was like, oh, this is like a subway above ground that's nice and on time. Wow. Like it's every New Yorker's dream, right? It's like the train's on time and it's nice. There's not like crazy people screaming at you,

• 43:25Anthony Pompliano?

  right? And like, whatever. And you can sit down and like, you know, it's like a nice experience. They have like a little food cart.

• 43:31Speaker 03

  Wifi, right?

• 43:31Anthony Pompliano?

  Wifi free. Like, I mean, it's like amazing. You walk into the train station, you could eat off the floor, right? I mean, it's like so clean, like all this stuff. And so you're like, okay, this is a better product, right? That ends up actually being put out there, has all these tailwinds along it and it's working. That is competition, right? And so when you look at something like that, it's like, man, why can't I bring this to the rest of the United States? Right? We can. And so what is it going to take? It's going to take people to do it. And I think that, I forget who tweeted this one time, but they were like, look around you. Somebody had a dream for every single one of those things, right? The building we're in right now, somebody was like, I think I should build that building. And then when they did it, and it's like weird to think about whenever that happened, that could have been two years ago or 200 years ago, right?

• 44:14Anthony Pompliano?

  Or 20 years ago. And somebody went and they got the plans. They went and they got the approvals. They then went and they literally poured the foundation and they built the actual building and like all this stuff. And you look around you, the whole entire world, that's true. And so like, Miami is probably one of the best examples. If you look at pictures of Brickell 10 years ago to now, it's like a different city.

• 44:33Speaker 03

  I saw a video on TikTok, actually, funny enough. And it was.

• 44:35Anthony Pompliano?

  Education content.

• 44:36Speaker 03

  Transformation is crazy.

• 44:38Anthony Pompliano?

  There was no high-rise buildings for the most part. Now, all of a sudden, 10 years later, it looks like a mini New York City, right? Now, again, I'm not going to say that Brickell is Manhattan, right? But like, it's definitely headed in the direction of more high-rises, more dense urban area, more restaurants, walkable, like all these things. And so that's in 10 years. Extrapolate that out over 30, 40, 50 years. If that continues, it probably only compounds faster, right? Because now more people are paying attention, more capital pours in, all this stuff. And so like, that area will look completely different. In one person's lifetime, right? And so I just always go back to this idea of whether we're talking about TikTok or we're talking about the bright line. Competition is the ultimate kind of game and it's this free market and the more we get back to that and people realize.

• 45:21Anthony Pompliano?

  If I want the world to look a certain way, I can do it. I can go compete and create that world. I think that's really one of the great advantages that we have in America because a lot of countries you can't do that.

• 45:30Speaker 03

  Yeah.

• 45:30Anthony Pompliano?

  Right? And so if you can do that here and you want something to change, go do it. It's your responsibility to go do that. And it'll make everything around your life and other people's life better.

• 45:39Speaker 03

  Hundred percent. And I think I even saw something the other day in terms of downtown Miami. Where it's like the second largest development in the United States and the first one was Hudson Yards recently. For that and now it's.

• 45:52Anthony Pompliano?

  Miami World Center.

• 45:53Speaker 03

  Yeah.

• 45:53Anthony Pompliano?

  I think that's like, uh, what is it? Art Falcone and Mark Roberts, a couple of those guys.

• 45:56Speaker 03

  Yeah. Yeah. So that's a, that's going to be huge as well.

• 46:00Anthony Pompliano?

  They'll be happy I mentioned them.

• 46:01Speaker 03

  Yeah.

• 46:03Speaker 03

  Exactly. So I, I think Miami for sure is on the come up and I think as long as. The policies here are good and it's, you know, it's the taxes, right? The weather. I think it's, uh, there is a huge migration right now, even, even still coming to, to Florida.

• 46:17Anthony Pompliano?

  When you are a nation of complainers, that is the first step towards socialism, right?

• 46:21Speaker 03

  Yeah.

• 46:21Anthony Pompliano?

  And one of the things that I continuously go back to over and over and over again is the reason why Miami, I think is so attractive to so many people in South Florida in general. Is, uh, the joke is that Miami is the capital of, uh, South and Central America, right? Or Latin America. And if you think about what do all of those people have in common? For the most part, most of those countries have experimented with some form of socialism. And those people wanted out and they moved, right? And so what ends up happening is if you've seen the experiment before. You vehemently reject those ideas when you see them again. And so I tell all my friends, I'm like, the last place in the United States of America that socialism will take hold is in Miami, Florida. Why? Because all of these people already saw the experiment and they ain't down for it.

• 47:07Anthony Pompliano?

  They're the people who moved with their feet and went somewhere else because they realized this is not the world I want to live in. And so like, that's one key piece to it. I think taxes is a big one. The weather's obviously nice. But also, there's this like magnetism that happens with density, right? And so like, all of a sudden, you start getting a couple of people to move. And then people are like, well, if they're all moving and I want to be around those people, then maybe I should move. And then you start to kind of compound that over time. I have a friend who actually moved from New York to Miami, and he said Miami is the Monaco of America. And I was like, why? And he was like, well, it's a lot of wealth, tax situation, it's near water. And there's this element of kind of as people want to move there and continue to move there, it becomes a thing, right?

• 47:49Anthony Pompliano?

  And so like, I think that's actually a great way to look at it is if you look in California, New York, etc. Some people move into Texas or Colorado or some of these places. But Miami has been a big winner in terms of flow of capital and a flow of people. And I don't think that it's going to reverse. But also, I'm actually of the belief that it's going to accelerate. So if you look at like Ken Griffin moving Citadel to Miami. Like, people don't realize that's hundreds, if not thousands of people that are high income earners that are going to move to a single city. He's going to build a high-rise tower, like all this stuff. Where are those people going to live? They're going to go into the community. Where are they going to spend their money? In the community, right? Like, like that one decision by that one person has this massive tailwind effect. And so when you think about it from that perspective, you're like, okay.

• 48:34Anthony Pompliano?

  How many more of those do you need to completely revitalize an area that wasn't necessarily destitute? Right? It was already pretty good. But you inject some capital, inject some people, game on. And, you know, I think that Miami could easily become the city of the 2020 decade. I saw somebody tweet and they said, every single decade has a city. So if you go back and you look at like the 90s and 2000s, it was New York. If you look at kind of like 2005 to like 2020, it was San Francisco. Like, are we going to be, you know, 2021 to 2030 or 2035 Miami? Unclear, but it's got a damn good shot to do that.

• 49:13Speaker 03

  Yeah, definitely. So when did, when did you move to Miami?

• 49:16Anthony Pompliano?

  At the end of 2020.

• 49:17Speaker 03

  Gotcha, gotcha.

• 49:18Anthony Pompliano?

  I rode out the whole thing in New York and then decided to leave.

• 49:23Speaker 03

  And you're like, I can't take it anymore.

• 49:25Anthony Pompliano?

  No, to be completely honest, like, I think my wife and I both, like, we heavily identify with New York.

• 49:31Speaker 03

  Yeah.

• 49:32Anthony Pompliano?

  And like our mentality, the way we work, a lot of our friends are still there, like, like. Yeah, I don't think it was like a, we're running from New York.

• 49:38Speaker 03

  Yeah.

• 49:38Anthony Pompliano?

  I think it was very much like, we love New York, we go back quite often. And if there was only, the only other place I think we would live other than Miami is in New York, right? And so I think Miami was more of just like, at first, let's go just for a weekend and like, see what's up. Then we realized a lot of our friends had moved, all this stuff. And so we were like, well, let's just try it for a couple of months. And that turned into now, you know, whatever, two and a half years. And I think that we look at it as like, basically it is as close to New York as you can get without it being New York, with better weather, better taxes and kind of density of people.

• 50:11Speaker 03

  Exactly.

• 50:12Anthony Pompliano?

  And so if you're fortunate enough to live in Miami and then maybe you just go back, you know, four to six times a year for, you know, a week or two, kind of get best of both worlds.

• 50:23Speaker 03

  Yeah.

• 50:23Anthony Pompliano?

  Like, to me, that is, you know, ultimate freedom, like the ultimate wealth is like that stuff, not some number in a bank account or anything. So it's like, we know that that's something that's important to us. And it's like, let's just go build that life.

• 50:34Speaker 03

  Yeah. So how's your travel schedule right now? Do you travel a good amount?

• 50:38Anthony Pompliano?

  I've been traveling drastically less. So in 2019, I took 120 flights. I was running around the world, I was fundraising, I was doing all this kind of crazy stuff.

• 50:50Anthony Pompliano?

  2020, obviously, took very few flights. In 21, I basically made the decision, I want to try to keep the 2020 schedule, but go back to kind of the work velocity and kind of capacity as the world opens up that I had in 2019. It was much more successful than I thought. And so I've pretty much said to myself, look, I will travel for certain things if I need to. But now I'm much more intentional about it. Like when I was single for sure, and then even when Plin and I were just dating, I didn't like really know responsibilities. I could, you know, get a phone call tonight and be on a plane. Literally, I would drive to the airport right now, right? And like, go fly somewhere if I needed to. It's different now, right? And so I think that by being more intentional, like we will go, there's a couple of trips that we have

• 51:35Anthony Pompliano?

  to make over the summer for work stuff, but we're going to go for like a week, right? And try to enjoy it and do all this stuff. And so like, yeah, I think it's less about like, are you traveling or not traveling? And now it's more like we travel in a different way. And by being more intentional about it actually is more enjoyable. Like, you know, I don't know how many planes I slept on, you know, red eyes and airports and canceled flights and like, this is a chaotic life, right?

• 51:57Speaker 03

  Yeah, it's chaotic.

• 51:57Anthony Pompliano?

  Fine, when, you know, you don't really have a lot of responsibility and you're kind of really focused on, you know, achieving something in the professional world, but how long can you really do that? Some people do it their whole career.

• 52:07Speaker 03

  I don't know how some people do it like, because I know some people, like what you said, they'll, they'll fly out on, on like Sunday night or super early Monday morning and then come back, you know, by like Friday morning or, you know, late Thursday night. And that's just, that's the schedule.

• 52:22Anthony Pompliano?

  Dude, I'll tell you two stories of things I used to do. So I used to drive to the airport on, in a morning, fly to Chicago, go do like two or three meetings and then fly back that night.

• 52:33Speaker 03

  Wow.

• 52:33Anthony Pompliano?

  Right? Then there was another time I flew to Chicago, I don't know why Chicago is both of these, but I flew to Chicago, we did a meeting, we got a rental car. Then we drove to, I think it was like Detroit or somewhere in Michigan, maybe? I forget. And then we like took a flight back, right? And it was like, what are we doing?

• 52:56Anthony Pompliano?

  But like it was important, right? There was things that we were doing, whatever. Part of it also was like, I always wanted to try to get home. Like I know a lot of people who, you know, they'll like plan these business trips and like, oh, I have a meeting on Tuesday at noon and then I'm going to meet a friend at 5:00 PM. And I could, you know, rush to the airport and try to catch the last flight, but I just stay overnight and I'll come back the next day. I always try to get back. And so when you try to get back, what you do is you kind of try to be more efficient, try to cram things in, but now you got two flights in a single day.

• 53:25Speaker 03

  Yeah, it's real.

• 53:26Anthony Pompliano?

  Right? And so, yeah, I mean, it's tough, but if, again, if you can just be more intentional about what you're going to do, it's a more enjoyable life.

• 53:32Speaker 03

  So how did you, how'd you meet your wife?

• 53:35Anthony Pompliano?

  Um, we met uh through work. Uh, she was a reporter at Fortune magazine. Um, she used to write uh articles about, you know, tech industry and venture investing. Eventually she became uh the writer behind term sheet, which is like Fortune's big uh daily email about the tech industry. Um, and it was kind of this weird thing where, you know, we met and um, I don't think that I had ever like dated or even got on a date or anything with anyone from work. I was very much like, hey, this is different, you know, the kind of different part of my life. Um, and in in the first meeting, it was kind of like, all right, we're gonna have to like, is this a professional relationship? Or like, are we interested in each other personally? Um, and I don't know, it's kind of like this weird thing. I never believed the like, oh,

• 54:17Anthony Pompliano?

  you know, as soon as you meet someone type. I was like, that's bullshit, right? Like, whatever. Um, but yeah, it was just like very obvious right out of the gate, uh, where it was like, I want to spend more time with that person, but you don't know what they think, right? So you're kind of like, uh, all right. And so we're just talking and like, it became obvious, I think, pretty quickly. Like, all right, we want to spend more time together. Um, and uh, I joke with it all the time. Like, that was it. Like, it was like, literally, I went from absolute maniac, you know, partying all the time, like, you know, had what most people would consider like the life in terms of like being a single guy, um, running around the world, doing all kinds of crazy shit.

• 54:53Speaker 03

  This was when? What year?

• 54:54Anthony Pompliano?

  Twenty... This is in 2016, at the end of 2016. And then like literally overnight, I was like, that's my girlfriend. And she was like, wait, hold on. I was like, that's my girlfriend.

• 55:07Speaker 03

  And this is back when you were, you know, you said you're you're single, going out, you were working a ton on business as well.

• 55:14Anthony Pompliano?

  It's like fucking, I used to have a saying, anything worth doing, uh, anything worth doing is worth overdoing.

• 55:19Speaker 03

  Yeah.

• 55:21Anthony Pompliano?

  Right? Like that pretty much, like that one sentence summarizes my life before I met my wife, right? It was just like, oh, we want to work? Cool. Let's work 12 hours, right? Oh, want to go out? Let's go out till four o'clock in the morning, right? Like, oh, want to drink? How about we drink 10 beers? Right? Like, just anything worth doing was worth overdoing. And like, to be honest, I like squeezed every ounce of juice out of my life, uh, I possibly could. And so I always joke, and she hates when I say this, but I'm like, if I literally die tomorrow... I won, right? Like, like I've had an amazing life. I literally have accomplished so many things that I wanted to accomplish and I had fun, right? Like I'm happy. And so, uh, I hope that doesn't happen, right? You know, not going, right? But like, uh, when you get to that point, I look back, I'm like, why did that happen?

• 56:03Anthony Pompliano?

  And it's because when I was 20 years old, right? And I was sitting in the desert in Iraq and you see a bunch of shit. All of a sudden you're like, you know what? Actually, I know what the end of this story is. And so let me go and do this. Now, when you're really young, that's like reckless stuff, right? You have a motorcycle, you're going fucking 120 miles an hour down the highway, like all, all the crazy stuff that people, uh, uh, kind of know. And it's well documented of young guys who, you know, feel like they're invincible, right? But now all of a sudden it's like, all right, what am I optimizing for? And when I ask a lot of people that I work with or, uh, companies I invest in or whatever, almost always the answer with a professional answer, right? And I always ask them, I say, is that what you are optimizing for in your life or in your work?

• 56:47Anthony Pompliano?

  And a lot of people, they never thought about what am I actually optimizing for in my life? And so for me, like it is this really stupid thing, but like my goal is to be happy. And that's also fluffy and all this stuff, but like, all that means is I took, okay, what makes me happy? How do I structure my days to do that as much as possible? Just do that. Like that's fine. And so like, there's a lot of people who probably look at my life now and they're like, dude, this is boring as shit. Like what? You have no hobbies? You have no, I'm like, no, you don't understand. I get to do my hobby all day long, right? You know, on, on the ride over here, uh, there's nothing on my calendar. Two people called me and I'm sitting there talking to them. I have no interest in their business. I have no benefit, like any of this stuff. It's just fun, right? I'm like, oh, you could do this. What about this? Did you ask this person this? Have you structured it this way?

• 57:31Anthony Pompliano?

  What would be the ramifications? Like, whatever. Last night at eight 30 at night, a founder called me and it's like hairs on fire, right? He's got a problem that he's dealing with. Yeah. And, and my wife's like, come on.

• 57:43Anthony Pompliano?

  But I'm like, hey, you know, it's like a guy who sneaks out in the backyard and he built a little putting green, right? I'm like, hey, like, you know, like the addict is gonna get here.

• 57:51Speaker 03

  Thirty seconds, yeah.

• 57:52Anthony Pompliano?

  It's only five minutes, five minutes, twelve minutes later, she's like, let's go. And so like a lot of the founders that I've invested in, like, they kind of know now, right? They're like, all right, look, I can call him and he'll answer, but like, I ain't got an hour. And so, but it is kind of like that, right? Is, uh, some people, you know, they literally can't wait for the basketball game. And they're like, dude, my friends are gonna come over, I'm gonna drink some beer and watch basketball game. I played three sports in high school, I played football in college, like, I love sports, right? It's really hard for me to sit down and watch entire seasons of sports now. Like, if you asked me at the age of eighteen to name NBA players, I could name a very high percentage of people, at least the starting five on like half the teams, right? Like, I, I like knew a ton.

• 58:35Speaker 03

  Yeah.

• 58:36Anthony Pompliano?

  I wasn't an expert, but I was very interested. Now, I don't think I could name the starting five on a single team.

• 58:43Speaker 03

  Wow.

• 58:44Anthony Pompliano?

  And so it's like, is that because I got more mature? Is that because like my life interest changed? Is that just because like I realized, hey, this is fun to like watch one game, but like I really don't care about the season? I don't know. But it's like probably one of the biggest differences because I have a brother who has doubled and tripled and quadrupled down on sports, right? And he could actually sit here and he probably could name the starting five on every single NBA team, right? And so it's a kind of this weird thing where maybe through life, you kind of get really interested in some things. And then at other times, you're interested in other things. I'm not sure.

• 59:14Anthony Pompliano?

  But I'm happier today than I've ever been, which is like a very weird thing because it's doing things that previously I didn't like to do. Like, I used to hate to read.

• 59:23Speaker 03

  Yeah.

• 59:24Anthony Pompliano?

  Right? Like, teachers be like, will you read? I don't think I read a single book in high school.

• 59:28Anthony Pompliano?

  Right? Like, like a signed book.

• 59:29Speaker 03

  Yeah, yeah.

• 59:30Anthony Pompliano?

  I just, I, I got through high school, but I don't think I read a single one they told us to read. And so like I was, I was a power user of Cliff Notes and like, I probably spent more time trying to figure out what the, was in the book than just if I had sat down and read the book, right? But like now, I'm like, man, if I went through high school right now, I'd sit in the front of the class, I'd ask all the questions, I'd read, I, I would be like the model student. Back then, I was the exact opposite, I was a complete class clown.

• 59:53Speaker 03

  Yeah.

• 59:53Anthony Pompliano?

  And so it's just like, I don't know, maturity, life, you know, interest change, whatever, but like, it's interesting.

• 59:57Speaker 03

  Yeah. It's interesting to see just the progression and how your things, but like what you said, the biggest thing is just figuring out what you really enjoy doing, what makes you happy and only doing that.

• 1:00:08Anthony Pompliano?

  That's it. That's literally, again, it goes back, what are you optimizing for?

• 1:00:12Speaker 03

  Yeah.

• 1:00:12Anthony Pompliano?

  And some people are optimizing for a number in their bank account. Some people are optimizing for an accomplishment, right? They want to achieve something, whether it's in their personal or professional life or whatever. I've just chosen like, I want to be happy. And the way that I define happy with my wife is we want to live an extraordinary life, doing the things we want to do when we want to do them.

• 1:00:32Speaker 03

  Yep.

• 1:00:32Anthony Pompliano?

  Right? And if you can do that every day, like you win. And so it's the old joke of people saying, you know, hey, uh, once I get rich, then I'll like become a writer. Or, you know, once I get rich, I'll do this, or once I retire, I'll do this. And it's like, cool, are you really going to work till you're 65 years old and then try to do it?

• 1:00:51Speaker 03

  Yeah.

• 1:00:52Anthony Pompliano?

  Like just do shit now.

• 1:00:53Speaker 03

  Yeah.

• 1:00:53Anthony Pompliano?

  Right? And, and once you start to kind of think that way, it scared the people. Cause like, maybe that job you thought you wanted at work is actually just a further investment in a bad deal. Right? Are you, is this bad money chasing, uh, you know, even worse money? Maybe. And so if you get the promotion, does that just mean you're going to be here for another two or three years? But you already hate the job. So why are you trying to achieve something that you know you hate?

• 1:01:20Speaker 03

  Yep.

• 1:01:21Anthony Pompliano?

  It's hard, right? It's hard to be intellectually honest with yourself.

• 1:01:23Speaker 03

  Yeah. And I think especially when emotions get involved, especially when time gets involved, like people, it's very tough to, to cut ties for anything.

• 1:01:32Anthony Pompliano?

  All of that is true. And then you add in responsibility, right? Like I, I, I always, I talked to a lot of small business owners, uh, uh, over the last couple of months. And one of the things I always ask them is I say, what's your responsibility? And most of them will immediately, cause we're talking to business sense, they'll start talking about, you know, well, we have a rent payment, we have this, oh, no, no, no, no. What's your responsibilities? Right? Oh, I got a significant other, I got kids, uh, my neighbor's kid, uh, has a medical bill and I'm helping him out with that. I got a car payment, I got a mortgage, I got like all this stuff, right? And so you like total it up and you're like, dude, you can't do anything else. Like financially, you are not in a position to make a different decision because the second you make a different decision,

• 1:02:13Anthony Pompliano?

  this tsunami of responsibilities, debt, whatever, will consume you.

• 1:02:18Speaker 03

  Yeah.

• 1:02:18Anthony Pompliano?

  And so you're trapped. And so the only way to get in a position to kind of make a move on a chessboard. You gotta deal with the responsibility stuff. Now, you can't get rid of your kids.

• 1:02:29Anthony Pompliano?

  Please don't get rid of your significant other, right? So there's like some non-negotiables, but there's a lot of things that actually you can address, right? And some of it is like, uh, uh, financial stuff. Some of it's social stuff, right? You'd be shocked at how many people are like, oh, well, every Thursday night I, I go and I do this. Why? Well, I've been doing it for, you know, 10 years.

• 1:02:48Speaker 03

  Yeah.

• 1:02:49Anthony Pompliano?

  Do you enjoy doing it? No, I hate it. Stop going.

• 1:02:52Speaker 03

  Yeah.

• 1:02:52Anthony Pompliano?

  Well, I'm gonna, they're gonna judge me or this or my, you know, this in the community, whatever. It's like, do you really care?

• 1:02:58Speaker 03

  Yeah.

• 1:02:59Anthony Pompliano?

  Do people really pay that much attention? Don't go next Thursday and see if anyone calls you. If they call, okay, then you're gonna have to address it. If they don't call, just never show up again.

• 1:03:11Anthony Pompliano?

  Maybe six months and they're like, hey, where's, you know, where, where's Andy? Like, no, I haven't seen him in a while, right? Like you, you just don't know. And so I, I tend to think a lot about like, um, uh, the responsibilities you sign up for. Uh, are they reversible or irreversible? A kid's irreversible, right? But a lot of responsibilities are reversible. And so like, which ones do you, should you be reversing and which ones do you want to keep doubling, troubling down on? You're investing your time. It's your most valuable asset. Think about it as a capital allocator. You're a time allocator. Where do you, where you put your time is ultimately where your focus goes, your energy goes, your happiness goes, et cetera. So invest it wisely.

• 1:03:46Speaker 03

  Yeah. And it's, it's so tricky in today's day and age because of lifestyle creep, right? It's, you know, especially early on in your career, as you start to get momentum in your career, right? You start making money, you start making better money. You want nicer things. It's just a natural part of, of life, uh, for most people. And I think.

• 1:04:05Anthony Pompliano?

  When you were younger, do you, did you have a number in your head of how much money you needed to make?

• 1:04:10Speaker 03

  I did, yeah.

• 1:04:12Anthony Pompliano?

  Okay. Was it like a, a net worth number? Was it like cash in a bank or was it like monthly income?

• 1:04:18Speaker 03

  It was a network number.

• 1:04:19Anthony Pompliano?

  Okay.

• 1:04:19Speaker 03

  When I was a kid.

• 1:04:20Anthony Pompliano?

  What, what was the number?

• 1:04:21Speaker 03

  Uh, at least a hundred mil.

• 1:04:23Anthony Pompliano?

  Okay. So that's a really big number for a young kid to, to think about, right? For me, when I was in college, this is gonna sound absurd. I literally was trying to back into, how could I make $2,000 a month? Because then I could live forever.

• 1:04:39Anthony Pompliano?

  Right? Like right now, like that sounds absurd now, right? You're like, dude, what? Now, this is, you know, a decade ago, 15 years ago, whatever, right? But like, when you think about that for a second, that was the goal, was like, $500 a week, I'm good. Right? Now you get into the real world and you get like slapped in the face and you're like, okay, hold on, maybe I need to make $5,000 a month. Right? But like you, lifestyle creep happens. I actually think a lot of people don't realize that when they stop and kind of look back like, dude, I accomplished every goal I've ever had financially until the goals I have now. Right? That's not because I'm some genius or whatever, but it was like, the goals weren't really that big.

• 1:05:23Anthony Pompliano?

  Right? So like a hundred million dollar net worth, I don't think I would have had the confidence or like the courage to have that as a goal. Mine was like $2,000. I got $2,000, like how did I get $5,000? Right? Like you kind of just move up. And so it goes back to this idea of like, if you could choose any, any point in history to live, you would choose tomorrow.

• 1:05:42Speaker 03

  Yep.

• 1:05:43Anthony Pompliano?

  The next best time to live is today, right? Like, like the world is only getting better, safer, more prosperous, all this stuff. If you think about your financial life, for most people, if things are going well, the single greatest time to be alive in your financial life is tomorrow. The next best time is today, right? Now, some people get in bad situations. So it's all about the compounding and like the direction of change. But if you are in a, if you're making good decisions, you do go from, you know, hey, I want to make $500 for the summer. Right? Then it's, I want to make $2,000 a month, $5,000 a month, whatever. And you kind of slowly build up. And as you check off each goal, it's kind of like natural, right? Like, what's the next goal? Cause you already achieved the thing that came before. And so in some ways, like lifestyle creep can be negative, obviously.

• 1:06:27Anthony Pompliano?

  But maybe it's like, you don't want lifestyle creep, but you want goal creep.

• 1:06:30Speaker 03

  Yeah.

• 1:06:31Anthony Pompliano?

  Right? So your goals get bigger, but your responsibilities stay the same. And that delta is really like the true wealth that you're generating.

• 1:06:37Speaker 03

  Yeah, I agree. I agree. And I think especially when I, when I first started out in business, it's, obviously I had that big goal in mind, but it's like, okay, how can I make, you know, 10K a month from this business? How can I make 50K a month, then 100K a month, then, you know, X amount? So.

• 1:06:53Anthony Pompliano?

  When you look at those goals too, what I think is so funny is business people, they always come with a plan. And so many people outside of the business world, they have like the goal, but there's no plan. Right? And so, um, one of my favorite things to do with young people is like, what do you want to do? Right? And I was talking to a kid recently, he's in college, trying to figure out a summer internship or whatever. He was like, I want to break into investing. I was like, okay, what's the plan? And he was talking all about, uh, how he was trying to like, get introductions to people and do all this stuff and everything. And I said, that is a path, you could, you could do that. But what if you flip it? How do you get them to come seek you out? He's like, what do you mean? I was like, if you want to meet people who you deem of high

• 1:07:35Anthony Pompliano?

  value, the best way to do it is to be of high value yourself. Right? Like be interesting. Yep. And so he was like, well, what do you mean? And I started talking to him. I was like, well, what happens if you had a niche that you got on Twitter and all of a sudden you became known as the person who had the expertise on X? Right? A lot of people would want to talk to you. And so, you know, for a college kid, like maybe your thing is you run surveys at all these colleges and you get all the technology trends and then you package it up and you send it to all the, you know, billionaires and VCs and all these people you want to meet and everything. And then you say, hey, by the way, I'm happy to jump on a call for 20 minutes and explain this to you. Right? And you send it to 400 of them. Five of them say yes. We just met five of, you know, your heroes. Like, you know, like these games of just like, how do you provide value rather than try to extract it? Yeah.

• 1:08:17Anthony Pompliano?

  Um, I think ultimately comes back to this idea of, uh, a plan, not just some wishy washy, like, oh, I hope that I could meet, you know, whatever. And so to me, uh, you know the story of the guy who stood outside of Tesla or SpaceX, uh, to meet Elon?

• 1:08:35Speaker 01

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• 1:09:03Anthony Pompliano?

  He like, was like live streaming and like posting videos on the internet for like 40 days or something. I forget all the details, right? Yeah. But like, I mean, that's insane. Yeah. Right? He met Elon. Right, like, like, imagine telling your grandkids, like, I one time hung out with the world's richest man. Like, how'd you do it, grandpa? I was a psychopath. I slept in my car outside his office and I literally harassed the shit out of him until he met me. Right? Like, respect, right? Now, please, please do not go do this, right? But like, that's a perfect example of like, he had a plan that seems insane to everyone. But like, eventually, it's like, okay, dude, this guy's been here for 45 days. Like, how do we get him to go away? Right? Just tell him to come in here and I'll, I'll talk to him for five minutes, right? And then he'll leave.

• 1:09:47Anthony Pompliano?

  And so like, there is kind of this weird world of just like, what are you trying to accomplish? What's the plan? Then go execute.

• 1:09:53Speaker 03

  Yeah, and I almost say a lot of people do that. If there's, there used to be a big trend on TikTok where it's like, it's like someone's like, day one of slapping myself every single day until X person responds to this TikTok. And like, that, that used to be a thing on.

• 1:10:10Anthony Pompliano?

  That is literally the Chinese Communist Party trying to make America dumb.

• 1:10:16Anthony Pompliano?

  Hey, kids, how cool would it be if you slapped yourself?

• 1:10:21Anthony Pompliano?

  Right? But like, I mean, but yes, right? A perfect example of like, trying to use the leverage of a platform to do something to get somebody's attention. Like, at the end of the day, whether you send a cold email or you slap yourself on Twitter every single day until someone responds to your DM, you're trying to get their attention. And the question is, what is the best path, right? And how do you get them to respond and do it in the context that you want them to know you as? But those two things are much more similar than, than they are different.

• 1:10:48Speaker 03

  Exactly. I want to talk a bit about your podcast. Like, how often do you, do you film episodes? Kind of like, how, how have you systemized that? And how has that grown, you know, since, since the beginning?

• 1:10:57Anthony Pompliano?

  Started out, there was no system. I mean, it literally was just, I just did whatever I wanted, um, which was fun, but not sustainable. Then we became highly, highly systematized. We did all kinds of different shows, all this stuff. And now I've kind of found like a sweet middle ground, right? Where, uh, we did two to three episodes a week. They're usually just the people I want to talk to. They tend to lean much more towards business, finance, economics, Bitcoin, things like that. And I just sit down and I talk to them like I do almost no prep, right? And it's just me trying to learn and um. Some people build podcasts because they want to build a business. I built a podcast because I wanted to learn and the business just happened to come along with it.

• 1:11:38Anthony Pompliano?

  But you know, we've done many times, we've made decisions that are financially disastrous for the business. But I don't care, right? Like my goal is to just meet people, learn from them. Um, and then be able to share that information with other people. And so again, what are you optimizing for? I'm not optimizing for the money, right? I'm optimizing for the learning. And so as we've done that, what we've come to the conclusion of is like. We want to have kind of a very loose structure in terms of how many episodes a week. Who are the types of people, that type of stuff? But actually, we don't obsess over, you know, did we grow 3%? You know, uh, we uh, day over day, did we grow 10%? You know, week over week, like we just don't do that stuff. And it would be bigger if we did. But again, that's not my focus, right?

• 1:12:21Anthony Pompliano?

  My focus is the learning component of it and it it'll kind of organically grow over time just from uh, from high quality content.

• 1:12:26Speaker 03

  Gotcha, gotcha. And so are you interviewing people two, three times a week? Or is it just you have some episodes where we talk alone? How do you balance that?

• 1:12:33Anthony Pompliano?

  It's all interviews uh, on the podcast, uh, YouTube. Every once in a while, I'll do a video where I just kind of talk uh, to the camera. They're way easier to do, right? Frankly than than the two hour interview. And uh, usually the interviews, what's fascinating about it is. I try to pull out information that isn't just about what they do, right? So same way that we're talking about goals or you know, daily routines or whatever like. Anyone who you meet, you can learn something from. But it's not only about the thing that they're an expert in. Because actually, I would argue that you and I are more experts in our daily routine than we are in business or finance or whatever, right? Because it's the thing that we do every single day, like we could talk with, you know, immense detail.

• 1:13:17Anthony Pompliano?

  You know, do you put your left or right shoe on first? Like you've got a system, right? Like, we can say whatever we want, but like you got a system, even if it's one that you don't intentionally create, right? When you brush your teeth, like, do you start on the left side or right side of your mouth? Like, we're humans, we're, we're, uh, built with this nature. And so how do you take something that like, I don't give a shit how you brush your teeth, right? But then how do you look at, well, how do you read? And so like, one of the, the funny things about, as I've read so many books is I'll meet people and they're fascinated with quote, quote, "the system" that I use to read, right? And then I'll ask them, well, how do you read? And some people will say, oh, I do audiobooks, right? And I don't take any notes and I just kind of listen when I'm out on a run or driving or whatever. Other people are like, oh no.

• 1:13:58Anthony Pompliano?

  I read on my Kindle, I highlight, I pull it into, you know, Readwise, I do like all this stuff and everything. And then what you start to learn is not only what the system is, but who the person is based on the system they use, right? If you take tons and tons of notes, that says something about you. If you take no notes, that says something about you, right? And neither one's good or bad, but you start to build kind of this like profile of someone and kind of who they are and what makes them tick. And so I love to do that in the podcast where, uh, you can talk about their area of expertise, but then you start to really understand them. And one of the things that gets lost on social media is the context around the conversation, right? So all you see, you see a profile picture and somebody you think is yelling and screaming at you. But then if you knew, well, wait a second here, hold on, this person's having a bad day,

• 1:14:40Anthony Pompliano?

  or this person, you know, has a certain viewpoint because of A, B, and C experience they have or whatever, you become more understanding. And so I just try really, really hard on the podcast, like, how do I extract that information? So that it puts more emphasis on certain parts of what they're saying around their area of expertise. I don't know if anyone, everyone gets that out of it, but for me, like, that's super, super valuable.

• 1:14:58Speaker 03

  Yeah, I agree a hundred percent. And I think it's, it's seeing a lot of these core fundamental, like, it's almost like you have your business operating principles and you have your life operating principles, right? And I think if you, if you have a good idea on both, You'll understand how someone got his results that they got essentially. So it's um it's it's very interesting to see.

• 1:15:20Anthony Pompliano?

  If you go back and you look at many of the most successful people in the world today, it will blow your mind at shit they did in their twenties, thirties. Right? Um, I was just listening to um uh the acquired podcast, I don't know if you ever listened out. But they do kind of these breakdowns of companies and stuff and they did one on LVMH and uh it's like three, three and a half hours. Fantastic work, right? And I'm listening to it and all of a sudden, uh, I'm literally working out and they say, and then Bernard Arnault moved to Palm Beach to build like shitty 20 unit uh multifamily like apartment buildings. In like, you know, early twenties or twenties, thirties, whatever he was. You're like, wait a minute.

• 1:15:59Anthony Pompliano?

  You're telling me the guy who literally owns, you know, uh Louis Vuitton and Dior and like all these like super luxury brands was literally building like affordable housing in Palm Beach. Uh, at one point and it's like, well, yeah, his family was in the construction business. They got out of like kind of the construction they were doing to get into like vacation rental type stuff. Then he was like, let's go to America, right? And he did it there. Then he ended up going back like all this stuff and you and you're like, dude, that guy was just trying to figure it out, man. Right? And like, he figured it out. He's, you know, second richest guy in the world. Like, he really figured it out.

• 1:16:29Speaker 03

  Yeah.

• 1:16:30Anthony Pompliano?

  But like when you, when you start to understand that you're like, maybe it's okay that I'm trying A or B or C in my life. And you can go through all these people, right? And and it's fascinating. And so like, um, you know, Warren Buffett is a great example. Right? Where like Warren Buffett early on with some of like the partnerships and some of the things that he did. If if you go back and you look, it's like not exactly what Warren Buffett is known for today, right? But that's because he was trying to figure it out, right? If you go um and you read uh Jimmy um uh Sony, I think is his last name. Uh, he wrote a book called, uh, I think The Founders, which is all about the PayPal mafia. And one of the stats in there is like four of the five PayPal founders had created bombs in high school.

• 1:17:15Anthony Pompliano?

  Okay, well, like, they weren't terrorists, right? Like, they were doing science experiments and they were trying to figure it out. And they were tinkering and like, it was like an inquisitive, curious mind type thing, right? Is at least the way that's presented. And so when you see that, you're like, okay, I don't think people should go do that, right? But like, maybe it is okay to try a bunch of different things when you're younger. And as you kind of build up the muscle memory and the experience and the connections and all the stuff, then you can start to find success. And so I tweeted this morning, the average age of a successful founder is 42 years old.

• 1:17:49Speaker 03

  Wow.

• 1:17:51Anthony Pompliano?

  Forty-two. Why? Maybe the first 20 years of their career is just practice. They learn, they try to build a little base of financial security. They get experience, they build connections, they do all this stuff. Only 42. That's the average age of a successful founder. So if you think about that, everything that happened in my twenties and thirties now, my wife and I, we always talk about like, we're practicing. There's a lot of people who look at the shit that we do and they're like, that's not practice, right? But I'm like, no, there's some bigger opportunity that will come in my 40s or in my 50s, maybe my 60s or 70s. And this is all practice leading up to that. And so when you make a mistake, it's practice, right? Learn from it.

• 1:18:34Anthony Pompliano?

  When you make a good decision, it's practice, it doesn't count, right? And so by presenting it to yourself as practice, you never believe your own bullshit and you never get too down when you make a mistake. And you realize that this is a lesson that I'm learning, right? That I then will apply in the future. And so it's been like this great kind of framework to constantly be serious, right? If you want to be a professional athlete, you're serious in practice. But also understanding it's practice. And so, hey, when the real game comes, whenever it comes, be ready.

• 1:19:05Speaker 03

  Yeah. And I think especially that's so true in business too. Like every five years, could be less, it could be more. You're reinventing yourself, right? It's like, you have a new business opportunity, like this first business you start might be some, you know, cleaning company in your local neighborhood or something that gets To a million dollars a year, but you know, next thing you know, you automate that and it's your next business that takes you to 10 mil or 50 mil, right? And then it's the next business after that, that's a, that's the nine figure opportunity. So.

• 1:19:36Anthony Pompliano?

  Hundred percent. And it's also something where you start to make connections across industries, right? You know, I mentioned earlier, these like industrial brokerage businesses, the second I saw them, I was like, oh, that's Uber. What's Uber? It's a brokerage business, right? I'm brokering writers and drivers. The only reason why I knew that was because I had looked at Uber and studied it, right? And, and started to connect. So like, what is this super high tech, you know, fast flying kind of tech company got to do with an industrial company? Same business model, right? Then there's businesses that you'll look at and you'll say, hmm, the makeup of this team matches exactly this other industry. Why? They're actually in the same business, right?

• 1:20:16Anthony Pompliano?

  And so like, one of the things I always love to talk to people is, um, you know, if you run a restaurant, you're in the restaurant business. People think you're in the food business, but you're in the restaurant business, right? Why is that different? Well, what are all these D to C food companies? They're not in the restaurant business. They're in the e-commerce business, right? And so understanding what game you're playing is really important because that determines capital, structure, team, marketing, like all these different things. But then what you start to realize is that restaurant, what do they really care about? How do we efficiently at low cost make great food? That D to C food company cares about the same thing, right? So there's similarities, but there's also differences. And so being able to identify, hey, what can you learn from the other? But also what are the things that you shouldn't take away, right?

• 1:20:59Anthony Pompliano?

  And, and being able to do that, I think just again, it's like being informed, having that like, a lot of people call like a prepared mind. So when you see an opportunity, you're, you're ready to go and then you can pounce on it.

• 1:21:09Speaker 03

  So for your podcast, are you, I'm, I'm sure you have someone helping you reach out and get guests as well. So is it kind of like a mix of?

• 1:21:17Anthony Pompliano?

  Nobody.

• 1:21:17Speaker 03

  Wow, it's just you?

• 1:21:18Anthony Pompliano?

  Yeah. Because of the people I want to talk to.

• 1:21:21Speaker 03

  Yeah.

• 1:21:21Anthony Pompliano?

  Right?

• 1:21:21Speaker 03

  And you're reaching out yourself.

• 1:21:23Anthony Pompliano?

  Yeah, just DM them on Twitter, email them, whatever. Every once in a while, somebody introduces me to someone or something like that.

• 1:21:28Speaker 03

  Yeah.

• 1:21:29Anthony Pompliano?

  But I would say for the most part, it is just me reaching out to them, saying, hey, you know, I'd love to talk to you. And, you know, incredibly fortunate in that a lot of people say yes. Right? Every once in a while, somebody says no, or the timing doesn't work or whatever. But yeah, it's just me reaching out. And I think it's, it's more, that is in line with kind of how I like to operate is, you know, I don't want people to have to like go and talk to somebody else on our team or whatever. Now, for scheduling and that type of stuff, sure.

• 1:21:55Speaker 03

  Yeah.

• 1:21:56Anthony Pompliano?

  But if I want to talk to them.

• 1:21:59Speaker 03

  You'll reach out.

• 1:21:59Anthony Pompliano?

  I'll, I'll, I'll ask you.

• 1:22:01Speaker 03

  Yeah.

• 1:22:01Anthony Pompliano?

  Right? You'll, you'll talk to me. And then, you know, our team, their team, whatever, can kind of work together on all the details. But at least they know like, hey, he wants me to come on. This isn't just like a mass email blast to, you know, 20 different people to see who, who will say yes.

• 1:22:13Speaker 03

  Yeah. Got it. And so you, you talk to people in, in finance and, and business. What, what have you learned, I guess? Cause I know you've interviewed tons of guests at this point. Like what, what are some of the, your, your toppings you've learned?

• 1:22:26Anthony Pompliano?

  The biggest lesson is the best investors don't follow the average financial advice. Right? The average financial advice is basically buy index funds, dollar cost average, hold them for a really long time. And kind of like diversify. Name a big investor that's ever done that. Like literally like a world-class investor. They do the exact opposite. Right? Heavily concentrated, heavy big bets. There's very little dollar cost averaging. It's like, I'm going to execute now. There's almost no diversification, like all, you know, they're super specialized, like whatever. And so there's this barbell where actually, if you know nothing, the kind of like generic advice is probably pretty good.

• 1:23:06Speaker 03

  Yeah.

• 1:23:07Anthony Pompliano?

  Right? It's like just get invested, get into the market, have the index and you're good to go. If you know a lot, the specialization, the concentration, you know, all that stuff is pretty good. The people that get in trouble, I think, are actually the people in the middle. The people who think that they know a lot, but don't, right? Or the people who kind of are like, oh, I don't really know that much. I know I don't know that much, but like, I'm gonna try to do it myself. Yep. And so it's like this like weird barbell. And so, you know, a great example is like diversification is the anti thesis to what Warren Buffett does. It's all about concentration, right? If you look at George Soros, who, you know, now a lot of people like yelling screaming about all the political stuff, but like, still one of the best investors in

• 1:23:47Anthony Pompliano?

  the world, like immense leverage, super heavily concentrated investments, and when the odds were in his favor, would bet real big. Again, you're kind of playing, you know, high risk, high reward game there, right? And so another one is a high risk, high reward. If you look at Monish Pabri, who's kind of like, he'll just come out and say like, hey, I just copied Warren Buffett, right? His whole thing is like, no, I'm a value investor. I actually want low risk, high reward. People are like, how do you get that? That's like the definition of value investing, right? It's things that like basically for sure you're gonna make money. Yep. And there's a potential that goes up a lot. And so like, all this, you know, kind of generic financial advice ends up actually not being what the best people in the world

• 1:24:30Anthony Pompliano?

  follow. Now, what's interesting is, then if you go to the other side, well, what's the positive argument for the generic financial advice? It works. Right? If you just dollar cost average into the S and P 500 for 40 years, you're gonna have more money. Yeah. Right? I don't know how much, or, you know, how often you dollar cost average, like, there's a lot of details in there. But like, you will have more money at the end than you do today just holding cash. Yeah. And so it then goes back to like, well, what do you want to do? If you want to be an investor, you got to quote unquote, turn pro. Even if you have another job, when you turn pro is the idea that Steven Pressfield has. Steven Pressfield talks about turning pro as a writer. If you want to write books, you want to do this, you've got to turn pro. What does a professional athlete do? They show up every day, whether they're sick, injured, you know, tired, whatever, and they do the work. And they do it all day

• 1:25:13Anthony Pompliano?

  long. They're pro, right? They are a professional athlete of whatever. Okay, if he says that for writing, what about investing? How many people turn pro as an investor? Right? Now a lot of people think, oh, I'm gonna quit my job. And like, no, no, no. You have to approach it as a professional. Do the work, put in the time, study, talk to people, like do all the stuff. Once you do that, then you have a chance, not a guarantee, but a chance to be a good investor. But, you know, we all know, I mean, I have a young brother, my youngest brother, who in 2021, he told me one time. I was like, hey, man, what are all your friends doing? He was like 24, 25 years old at the time. What are all your friends doing investing wise? He's like, ah, man, you don't want to know. And I was like, why?

• 1:25:56Anthony Pompliano?

  And he's like, I mean, they just invest in all kinds of crazy stuff right now. And I was like, like what? He goes, they won't invest in anything unless they think it can go up 10x. And I remember being like, oh, shit.

• 1:26:08Anthony Pompliano?

  Right? Cause it's just like, like that is such an insane thought process. As a response to the economic environment. Now, if you're saying, no, I'm gonna make heavy bets, like, like it's more of like a calculated investment strategy. Okay, fine.

• 1:26:21Speaker 03

  Yeah.

• 1:26:22Anthony Pompliano?

  But this was just like, money is free and you know, it's flowing everywhere. And so like, I basically only want things that are super asymmetrical. And so I think that's like a perfect example where you had people who weren't that educated, but you know, wanted to be professional investors. That's not what I'm talking about.

• 1:26:35Speaker 03

  Yeah.

• 1:26:35Anthony Pompliano?

  Talking about actually turning pro. So that's one big lesson. A second big lesson is people are all trying to figure it out. I have some of the world's most successful people come onto the podcast and I talk to them after the podcast about different things. And they sound like they are fucking confused.

• 1:26:50Anthony Pompliano?

  Because they're just like, yeah, like everyone knows me for this thing. And I got this thing figured out in the eyes of the public. But like, dude, let me pull back this curtain, look at this fire that's going on over here, right? And everything's on fire and I'm trying to figure it out. And I just had an employee quit and I had this happen, I had this like, and you're like, oh shit, like my problems ain't that bad, right? So I think that's another one. One of the things that I think is really interesting is some of the best investment ideas don't come from traditional sources. So like you can read research, you can do all stuff, whatever. There are story after story after story of, you know, how Teal invested in Facebook, how some of the Lightspeed guys invested in Snapchat.

• 1:27:30Anthony Pompliano?

  How, you know, somebody invested in Google because the Google founders were working out of their garage, like, like all this like. Weird shit, right? It's like nobody was like sitting there reading a Wall Street, you know, research report being like, oh, the company Google has a 7% chance of disrupting the 20 search engines that come before it.

• 1:27:46Speaker 03

  Yeah.

• 1:27:47Anthony Pompliano?

  No, it's like somebody went to a party, right? Like a barbecue at someone's house. And they were like, oh, that guy Larry over there is starting a company. What are you starting? I'm a Stanford genius.

• 1:27:57Speaker 03

  Yeah.

• 1:27:57Anthony Pompliano?

  Here's 50K. Let's see what happens, kid. Bam, Google.

• 1:28:01Speaker 03

  Yeah, it's not like hundreds of pages of research where it's like super like linear, right? It's not, so.

• 1:28:07Anthony Pompliano?

  So like one is like people are in financial position where a 25 or 50K check didn't, it didn't warrant the research, right? So like they're fortunate to be in that position. But also it goes back to like, maybe if they had done a bunch of research, they would have talked themselves out of it. Right? So like you get into kind of that, that kind of weird, you know, analysis. But also the Google founders didn't even think they were going to build what they were going to build. Right?

• 1:28:30Speaker 03

  True as well.

• 1:28:30Anthony Pompliano?

  They were that they wanted to sell it for like a million bucks or something, 10 million, whatever it was, right?

• 1:28:34Speaker 03

  Yeah.

• 1:28:35Anthony Pompliano?

  Like imagine if they had sold for a million dollars.

• 1:28:40Anthony Pompliano?

  It's like comical.

• 1:28:41Speaker 03

  Yeah.

• 1:28:41Anthony Pompliano?

  And so now here's where you get, you put reading, learning all this stuff together. The story of Google trying to sell for a million dollars and no one wants the business. And so they are forced to go build it and they end up building Google is the exact same story as Jay-Z. Jay-Z tried to get a record contract. No one would give it to him. So what do you do? He said, shit, I gotta flood the streets with my mixtape. I gotta build my own record label. Right? I gotta bet on myself. And they say, no, bam, Jay-Z happens. Those two stories are the exact same thing where nobody wanted them. And they were forced, not by choice, they were forced to go do it themselves and ended up working out. For every one of those good stories, there's a thousand bad ones.

• 1:29:22Speaker 03

  Yep.

• 1:29:22Anthony Pompliano?

  But those two stories are the exact same story.

• 1:29:25Speaker 03

  Yeah. So how do you balance like, you know, the research linear logical side with this, you know, non-routine, like going to just some networking party, saying yes, doing these things where you can basically make that connection, right? Like, how do you balance the, the chaos and, and the routine to become a better investor?

• 1:29:49Anthony Pompliano?

  Do you decide with your gut or with your brain? You gotta decide who you are. I'm gut, right? And there's a lot of people who say, don't decide with your gut. I look at my gut, right? As it is the culmination of all the information I have in my head. Can't explain it. Sometimes I'm like, yep, I should do it. Sometimes I shouldn't. I'm wrong.

• 1:30:07Speaker 03

  Yeah.

• 1:30:07Anthony Pompliano?

  All the time. But given the type of investing that we do, it's all about power loss. You gotta be right one time, right? And so actually going with your gut where you're like, this could be big. It's all about how big could it get? Not how much could we lose?

• 1:30:19Speaker 03

  Yeah.

• 1:30:19Anthony Pompliano?

  In venture investing. And so going with my gut nine times out of 10 is a much better thing than if I sit down and start calculating shit. Right? I, I have this like standing rule. I don't look at financial models in terms of early stage startups. People are like, that's insane. Why would you do that? No, it's literally fiction. They're fucking making it up.

• 1:30:38Speaker 03

  Yeah.

• 1:30:38Anthony Pompliano?

  They're guessing, right? Like, it's like, okay, you guys made one, let me make one, right? I don't think you're gonna do 10 million, I think you're gonna do 2 million. Why? I don't know, I fucking made it up, right? Like, like there, it's just complete fiction. And so, yeah, maybe I'll do like a little like Googling, you know, like, oh, how big's the market? Right? Or like, like very loose type stuff. But at the end of the day, I'm investing in this person. And so I've invested in, I don't know how many, 10, 12, 13 different unicorns at this point where I was an early investor in them. And if I go back and I look at most of them, most of them are still doing something that is tangentially related to what they originally pitched. But very few of them are doing exactly what they originally pitched. And so if you go and you study like a Clayton Christensen and kind of the disruption, uh, theory and all this kind of stuff, or innovator's dilemma.

• 1:31:23Anthony Pompliano?

  Uh, what you find is that there are like, uh, kind of, uh, defined strategies. And then there's something he calls like an emergent strategy. And so defined strategy means like, I am going to build this table. And here's the exact specifications. Here's the material I'm gonna use and all this stuff, right? And I go and I build it. Like I followed the defined strategy and I did exactly what I said I was gonna do. That's great when you're building one single unit of a product, right? But if you wanna build a company, what you do is like, I'm gonna build 50 tables and then I'm gonna sell them to this person. I'm gonna do it for this price, whatever. And then you go talk to the customer and they're like, dude, I'm not buying it for that. Shit.

• 1:31:55Anthony Pompliano?

  Right? Okay. So like either I'm it's over or well, how much would you pay? What type of materials are interesting to you? What are you going to use it for? So learning? Oh, well, rather than sell them the 50 tables for that price, I thought, what if I actually built it with a different material? I could lower the price and then rather than them use it inside of their really fancy, you know, a commercial real estate building. Actually, what they're going to do is they're going to use it out back in the recreation area and the cheaper material will make it, you know, affordable, blah, blah, whatever. Great. You'll buy that? Awesome. Okay. I'm going to go follow that strategy now. Right? That's the emergent strategy. It's because the defined strategy ended up not working. And so when you go and you look through all these companies, most of them did not actually end up building what they thought they were going to build.

• 1:32:37Anthony Pompliano?

  Right? Amazon, Jeff Bezos never thought about AWS.

• 1:32:42Speaker 03

  Yeah.

• 1:32:42Anthony Pompliano?

  Right? He was going to sell books on the internet and maybe he could sell some things past that. AWS is pretty good business, right? Facebook was called Hot or Not.

• 1:32:53Anthony Pompliano?

  Right? And they were basically or FaceSmash, whatever the hell it was called, right? Like they were basically like, are you hot or are you not? And turned into Facebook, right? And so like you start to like see some of the stuff and you're like, man, you want to have a defined strategy, but you got to be open to the, the kind of emergent strategy and be willing to jump on that. Um, and then one other thing I would say that, uh, I think is pretty interesting. Is the more successful and older someone is, the more obsessive they are with surrounding themselves with young, intelligent, hardworking people. So, um, I've been fortunate to go to a bunch of, uh, these folks offices. And like, so this isn't like, you know, uh, social, right? This is work, right?

• 1:33:33Anthony Pompliano?

  They are in an office and literally the richer they are, the more young people there are. And it's because they're getting older and they know I have to disrupt myself, but I'm old, right?

• 1:33:48Speaker 03

  Interesting.

• 1:33:49Anthony Pompliano?

  And so, you know, we have a, we have somebody who works for us who he texts me sometimes. And it's like, uh, I'm, uh, deciphering like, you know, the Magna Carta, right? He'll be like, uh, uh, something, something F Rs, you know, words, words, words. I'm like, the fuck is F? Oh, for real? Like I gotta think, right?

• 1:34:05Speaker 03

  Yeah.

• 1:34:05Anthony Pompliano?

  And then the other day I asked him how something he did, he did like an event thing. And I was like, how'd it go? And he hit me with P good. Pretty good, right? Like, like I literally felt like I was like a detective, like uncovering what he was saying.

• 1:34:17Speaker 03

  Yeah.

• 1:34:18Anthony Pompliano?

  And so I thought for a second to be like, hey dude, can you write the words out?

• 1:34:21Speaker 03

  Yeah.

• 1:34:21Anthony Pompliano?

  And I was like, no, actually I want him to text like this because guess what? That's how he's texting his friends. Right? And so I didn't know P good meant or FR. But as I was realizing, I was like, one, shit, I'm getting old, right? But two is, man, how do I learn more things from him? He probably thinks he's learning a lot from me, but I'm learning just as much from him about how, you know, a 21 year old and kind of his friend group operate. That's gotta tell me a lot about how the world's gonna play out over the next, you know, 20 years.

• 1:34:49Speaker 03

  And I think that what you're saying, it goes back, right? Because I, the light speed venture partner who invested in Snapchat, it was his daughter who basically was like, look at this app that all my friends are using.

• 1:35:05Anthony Pompliano?

  Yes.

• 1:35:05Speaker 03

  Right? So.

• 1:35:07Anthony Pompliano?

  I mean, that's how a lot of these things end up getting discovered, right? If you have a product or a service that is targeted to a kid, right? How's an adult supposed to find it?

• 1:35:17Speaker 03

  They're not.

• 1:35:18Anthony Pompliano?

  Maybe they buy it for their kid or something, right? But like, no. And so, you know, my wife, we joke all the time, she's a better investor than me. She has told me about four different companies that ended up going on to be billion dollar businesses that she told me very early on. And I was like, I don't know, whatever. Right? Like, I don't know anything about that type of thing. And I asked her, I was like, okay, timeout. Like, how, where's the deal flow coming from basically, right? And she was like, no, you don't understand. She's like, I am the perfect demographic for these products and services, right? Because she was in her late twenties as a woman with a friend group where word of mouth goes viral, like all this stuff. She's like, and a lot of times I would just look and see who's spending a ton of money on Instagram, on Facebook and Instagram ads to target me.

• 1:36:01Anthony Pompliano?

  They have money. They're spending a lot. If I see my friends then posting about it like, like you just, you can very quickly figure out, oh shit, this is becoming big.

• 1:36:09Speaker 03

  Yep.

• 1:36:10Anthony Pompliano?

  Right? So like, is it better to read the Wall Street research report? Is it better to talk to other like, you know, uh, you know, old dude VCs? Or is it better to talk to my wife who literally is like getting bombarded with Instagram ads?

• 1:36:23Speaker 03

  Yep.

• 1:36:23Anthony Pompliano?

  Like actually she had the advantage on that specific market.

• 1:36:27Speaker 03

  Yep.

• 1:36:27Anthony Pompliano?

  Right? Now she's gonna have zero clue, uh, for a business that's targeting, you know, 30 year old dudes. Right? It's just, she's not in the demographic. And so a lot of times it's like, go and find the people who are organic to that community and they know. Right? And so like one of my favorite things to do when I talk about a lot is like the small businesses. We talk to like the number two or three in charge. Like, hey, if Joe wasn't here for a month, what would you do to grow the business?

• 1:36:54Anthony Pompliano?

  And the things they tell you are like completely different than the plan. Right?

• 1:36:57Speaker 03

  Yeah.

• 1:36:57Anthony Pompliano?

  And you're like, why this? And they have like very good, well, this and this and this. Why aren't you guys doing that? Eh, Joe's got his plan. You know, we're gonna do Joe's plan. And so you're like, okay, right? Like, hey, let's have a conversation about this.

• 1:37:09Speaker 03

  Yes.

• 1:37:09Anthony Pompliano?

  Why is these people who are usually younger, you know, kind of more involved in the day to day, have a different type of plan or a variation of the plan that the business has? Right? Then you go to like a tech company. And if you go and you talk to all the employees, like, hey, if, um, uh, if you wanted to grow the business, you know, you want to grow the user base by two X, what would you do? Sometimes there's overlap, right? They're providing the ideas to the company. Sometimes there's ideas and you're like, that's actually a good idea. Like, why aren't they doing that? Like, I haven't told them.

• 1:37:35Speaker 03

  Yep.

• 1:37:37Anthony Pompliano?

  Go tell them. Right? Go try it. Go experiment. And so I think that it's just, again, like, ideas can come from anywhere. Right? You just gotta kind of really pay attention. Um, just double down on the good ones.

• 1:37:47Speaker 03

  Final question I have for you is, how much weight do you put? You know, obviously I know you said you're more, you're more of a gut instinct type of person. How much weight is it for you in terms of like, hey? I'm placing my bet on the founder itself versus the idea in the market and how big it can potentially be.

• 1:38:08Anthony Pompliano?

  Every mistake I've ever made in investing, like big mistakes, I fell in love with the idea. Every great investment I've ever made, I invested in the person.

• 1:38:17Speaker 03

  Got it.

• 1:38:17Anthony Pompliano?

  So I still make mistakes, right, all the time. And I'm human, I get excited about, you know, oh, look at this massive market, whatever, right?

• 1:38:26Anthony Pompliano?

  But this person.

• 1:38:27Speaker 03

  Gotcha.

• 1:38:27Anthony Pompliano?

  It's really the person. And it's because everything is going to change, especially in the early stage, right? When somebody comes and says, hey, I got an idea, like that's really where I spend a lot of my time.

• 1:38:39Anthony Pompliano?

  The product that they're talking about is going to change, right? The emergent strategy stuff. The market is going to change, the competitors are going to change, the funding environment, the economy, the talent on market, all that stuff's going to change. The one thing that's not going to change in this business is who's running it. And really what you're trying to get at is how good of a decision maker are they? If they make good decisions, they got a shot. Right?

• 1:39:04Anthony Pompliano?

  Good decision doesn't mean a sane decision maker, though. Right? A sane decision maker doesn't build Tesla, doesn't build, you know, Facebook. Right? No, you need someone who is a good decision maker, but has a unique view of the world. And so you start trying to pull out some of these, you know, kind of insights or things from people and it goes back. It's not like I got like a scoreboard, right? Where I'm like, okay, decision making, that's a seven. Oh, unique perspective on the world, that's a three. Right? I need a 12 to be able to invest, that's only 10, so I'm out, right? Like, no, it's just, it's kind of gut. And, you know, it's easier for me to say gut because I've invested in so many companies now and I've seen enough of them kind of over time. End up, you know, which ones working, which ones don't.

• 1:39:48Anthony Pompliano?

  But also, it's a probability game. And so if you go into it trying to avoid mistakes, you'll be a horrible investor and venture. If you go into it and you're like, I'm just looking for the grand slams and like, I know I'm going to waste a bunch of money.

• 1:40:03Anthony Pompliano?

  That's okay, right? Because the way the portfolio is constructed, that's what you're supposed to be doing.

• 1:40:07Speaker 03

  Awesome. Well, that's basically all I have on my list. So I appreciate you taking the time to talk about.

• 1:40:14Anthony Pompliano?

  Can I ask you one question before we end?

• 1:40:15Speaker 03

  Of course.

• 1:40:16Anthony Pompliano?

  What's the one thing you've learned so far? I think I'm episode eight. What's one thing that you've learned so far in the first eight conversations?

• 1:40:23Speaker 03

  The thing I've learned the most so far? I love learning about people's decision-making skills or just thought process. And then I love correlating that to basically where they are. So like, you know, when I ask questions, like I'm genuinely interested in terms of like, you know, for you, when I was asking like, you know, what do you do outside of work and stuff? You said you had no hobbies. Funny enough, I don't have other hobbies as well. Right? And so like, I love learning about these little things in terms of how someone got to a decision. Because it gives me context in terms of, okay, that makes sense. I'm on board. Why am I not applying that? Or it's like, oh, that makes sense. I personally don't want that.

• 1:41:06Speaker 03

  But I love knowing the decisions in terms of how someone got there. And so every time I talk to someone, you know, I interviewed, you know, a couple of other people before you who had their own podcasts. And it's interesting because everyone has their own view of like, why they're starting the podcast, how they get guests and things like that.

• 1:41:27Speaker 03

  But it's less about like, who's right and who's wrong versus, you know, the why and the decision to get there.

• 1:41:35Anthony Pompliano?

  I think that's exactly right.

• 1:41:38Anthony Pompliano?

  Advice is only helpful if it's actually applies to your life.

• 1:41:41Speaker 03

  Correct.

• 1:41:42Anthony Pompliano?

  Right? And so if I told you, you know what you should do? You should go build out a whole TV studio and like all this stuff. You're like, that's not what we're trying to accomplish here.

• 1:41:48Speaker 03

  Exactly.

• 1:41:48Anthony Pompliano?

  And so I think that just knowing who you are and being comfortable with what you're trying to accomplish is a great advantage in life.

• 1:41:54Speaker 03

  Awesome. Well, thanks for coming on the show, Pom. We're happy to have you and I'm sure we'll stay in touch, so.

• 1:41:59Anthony Pompliano?

  Absolutely. Thanks so much for having me.