Anthony Pompliano (Pomp) breaks down how he built a multi-business media empire around his podcast and newsletter — including why he fired all his advertisers to own the products instead, how he structures Inflection Points as a holding company, and his thesis on distribution as the key competitive advantage in the 21st century. The conversation also covers hiring young internet-native talent, the D-Gods NFT story, and Shaan’s Milk Road adventures with Billy and the wife-beater offsite.
Speakers: Sam Parr (host), Shaan Puri (host), Anthony Pompliano / Pomp (guest, founder and media entrepreneur)
Episode Intro and Pomp’s Background [00:00:00]
Sam: Can we talk about value creation instead of — because Pomp owns like four companies I think that I wanted to ask him about, and my fight-or-flight mode is like too much right now. I need a rags-to-riches story. I need something interesting. Tell me how he makes the paper, because I need to calm down. I need to meditate. Stop telling me how he makes income. Is that all right, Shaan?
Shaan: Yeah, but what’s your question? How do you want to frame it?
Sam: So Pomp — he has, from what I understand, four or five different companies. He has this office in Miami. It feels like you have — at first I was going to call it a mini empire, but it doesn’t sound so mini. Actually, it sounds medium empire.
Shaan: Medium empire.
Sam: Yeah, maybe big empire. I don’t know. Can you explain what are the things you’ve got going on?
Pomp: Yeah. If you really think about my career, there are kind of three stages. At first it was like, how do I build companies? I had enough success where I was like, okay, maybe I’m not horrible at this, but I definitely don’t know how to build companies to scale.
That led to Facebook — that was kind of my equivalent of an MBA. I was with all these super-talented people in 2014 and 2015. I was put on a number of different projects where I got exposed to Mark Zuckerberg, Sheryl Sandberg, and a bunch of the leadership, and I just learned a lot. It was the best learning experience possible.
Shortly thereafter I started investing. I didn’t have an idea to start a company so I thought, let’s try this investing thing. I really enjoyed doing it. I ended up building two different asset management firms.
But I keep coming back to this: venture capital is such a slugging-percentage game that what you end up doing is playing an access game almost more than a business game. And what I mean is — outside of maybe the big five or six venture capital funds — once a company gets de-risked, it’s all access. It’s literally who do you know, how do you get into a deal, how do you get an allocation. That’s fun, but to me that’s more of a status thing: do these people think enough of me to invite me into the deal? That’s maybe the underbelly of the venture capital industry.
Why Pomp Chose Content Over VC [00:03:30]
Pomp: So simultaneously with building those asset management firms, I started creating content on the internet. In hindsight, it was optimized initially for learning. Then it kind of switched — oh, there’s a lot of deal flow that comes from this. So I took it a little more seriously. And then there was this final transition: oh, these are actually businesses.
The big aha I had was: historically you built a company by building the product and then going to find customers. Now you can find the customers and then build the product. That’s essentially what we’ve done. We’ve built a very large audience — the podcast is 25 million downloads last year, YouTube is half a million subscribers. One day I think you guys are going to pass me, so keep going.
Sam: Is the podcast bigger than us right now? Are you trying to flex on us or are we already bigger?
Pomp: Downloads range from about 100,000 to 150,000 per episode. So the RSS feed is in the 100,000 range, sometimes more sometimes less, and then YouTube videos are 20,000 to 50,000. So that’s why we say 100 to 150 thousand. You guys will do more than me on individual episodes, but I have this crazy power law — we just put up an interview on YouTube that got 100,000 views in the first 12 hours. So it’s very concentrated on the long tail.
Which is interesting, right? Would you rather have consistent 50 to 100,000 YouTube and podcast, or would you rather have the breakout million-views-plus every month or so?
Shaan: Yeah.
Pomp: Maybe you’ll catch up to us one day.
Building the Business Empire: Inflection Points [00:06:00]
Pomp: The general idea has just been: how do you build businesses once you know who the audience is? Then you can go build products. I very much look at it as a game. And it goes back to the whole idea — I don’t have hobbies. This is what I do in my free time, and I really enjoy doing it.
So we’ve built a number of different businesses. Some have been bigger than others. But really, if you have distribution, you can build companies in the 21st century. We see big creators doing this, and I tend to think anyone can do it.
Sam: What are the businesses? So number one: media company with advertising — is that a substantial-sized business?
Pomp: It used to have advertising, and it was a very substantial business. It was probably one of the best-monetized podcasts in the world relative to audience size. Both on the revenue side and on the downloads.
I turned all the ads off. There were really two things that fed into it. One: when you have an advertiser, you go find companies you like, say “hey, I use this product, you guys should check it out.” That’s fine if you’re doing like a bar of soap or liquid death or whatever the normal product is. The problem in finance is people put their money into a product that you’re recommending, and you’re essentially renting your reputation to someone else. You have no control over the business, you don’t know what they’re doing. It’s not like “oh, I bought this chair or this sweatshirt that Shaan and Sam said was great, I don’t like it” — the idiots, right, but I’m not that worried about it. When somebody puts their money into a product, it’s a whole different game. And a lot of them were crypto companies, and crypto companies kept blowing up.
Sam: Right.
Pomp: But the second thing I realized from a business opportunity standpoint: when I got rid of all the advertising, I knew we would take a massive hit. We’ve got a team, an office, all this stuff. So I had to commit to personally covering everything. I’ve been losing money every month, but I’m doing it because the bigger opportunity is to actually own the products and services you put through the distribution.
Think of it like this: you guys will get paid as a podcast host maybe one dollar to read an ad. But the advertiser is making three to five dollars on the back end as their return on advertising. If you can cut out the middleman and just own the product or service, that’s a way better deal.
The reason most people don’t do it is they don’t have the skill set or the interest in actually building the product. So I was like, look, we’ve figured out advertising-based content. I want a hard challenge. I want to do something that is, by most people’s account, stupid — give up all this revenue and go try this. Intellectually stimulating, and if we figure it out, it’ll be a way bigger and more sustainable business in the long run. You just have to weather the bumpy transition.
The Fund Story: Why He Gave Back the Money [00:11:00]
Sam: Hold on — the fund. Didn’t you give all the money back? Aren’t you no longer in the fund?
Pomp: There are two different asset management firms. One was a joint venture with Morgan Creek Capital, a hedge fund. We invested all the capital — in companies like Coinbase, bought some Bitcoin, those types of things. And we get a cut if it ever does well.
Then I had a second asset management firm. I was one of the first people to do a rolling fund on AngelList, which I found was an incredible product for someone who has a small team and wants to punch above their weight. We grew it into maybe the third-biggest rolling fund on the platform at the time, made a bunch of investments.
But I got to the point where I did the math. If I invest personally in pre-seed and seed deals — which is what I actually enjoy — versus out of a fund, a lot of times it’s actually better economically to invest personally because of how the carry and management fees work. And on top of that, now I don’t have to spend time on LP updates and all the things that go into managing a fund. I get time back and I could make more money. I’ll always pick that.
So I gave back all the uninvested capital out of that fund and now just do all my investing personally.
Sam: Do you do big checks or is it like the normal 15 to 30 thousand angel check?
Pomp: I’ll do bigger than that. But what I’ve over time started to realize is — it goes back to why I want to start some of these companies. Investing in other people’s companies is great, and obviously the power law takes over and that can be amazing. Angel investing can be really profitable. But actually, you’re much more likely to be able to take 50 to 100 thousand dollars, start a business, get to a million dollars in revenue, and throw off 500 to 700 thousand in profit year after year after year — and do it with a very high degree of probability of success.
In some ways, what’s better than angel investing in other people’s ideas? It may actually just be angel investing in your own ideas, your own companies. So that’s really where I’ve been focused. Yes, I’ll still on occasion invest in other companies, but now I want to start these businesses.
I look at it as: what is the competitive advantage? We have capital, but we also have distribution. If you have capital and distribution, you basically just need a decent idea and an absolute killer operator. If you can find those two things and combine them with capital and distribution, you’ve got a good chance of making some money.
Biggest Angel Investments [00:15:30]
Sam: What’s your biggest angel investment, or what do you think will end up being the most successful one?
Pomp: Bitcoin is probably the one that will end up making the most money, both in terms of the amount I invested and the aggregate dollar value it’ll be worth. I tend to be in Shaan’s camp — the dollars won’t matter, it’s going to be the Bitcoin.
Some that people might find interesting: I invested in Varda — Delian and those guys — they’re doing space manufacturing, which I find really fascinating. A friend and I invested in something called Everlywell out of Austin; they do at-home diagnostic testing. I invested in Howard Lerman’s new company Rome — they’re building a workspace for remote teams, kind of a Zoom and Slack killer, which seems to be doing very well. And a whole host of others.
The Four Businesses: Jobs, Recruiting, Training, Research [00:17:30]
Sam: All right, so we’ve got the fund and investing, the media company. You also have Crypto Academy, Crypto Jobs, which has parlayed into a proper recruiting service.
Pomp: Yeah, those three. You can basically think of the Inflection Points business — that’s become a holding company for all these different products and services within a specific vertical.
I’m fascinated with Mark Leonard. I don’t know if you guys know Constellation Software — he basically buys vertically-specific software companies. Well, what if you don’t have a holding company that buys across different verticals, but instead just have a holding company within one specific vertical? That’s basically what we’ve built.
We have a job marketplace where companies can list their open roles, they pay for it, we use the distribution to drive traffic, people can go get a job. That’s Crypto Jobs — cryptojobs.com.
Sam: And that’s a pretty basic business. It’s just a job board.
Pomp: Exactly. That’s how we got started. We launched it, it got to about $50,000 in monthly revenue pretty much in the first four weeks. So we’re like, okay, we have a business, let’s scale this.
We then bought a recruiting company — traditional headhunters — called Proof of Talent. So you can either do self-serve and list jobs yourself, or you can work with the recruiters who just take a percentage of the first-year fee.
Then we started doing corporate training. A very large company came to us and said, can you train our people? We got into that business and grew it to seven figures in revenue.
And then we just started a research business. Think of it as buy-side research — you pay a subscription fee and they deliver research a couple of times a week. It’s called Reflexivity Research.
Sam: Let’s talk about that one, because that’s a perfect example of what you’re describing.
Pomp: It really is. Will Clemente is a young guy in the Bitcoin and crypto world who has done really great analysis. I worked with him for about a year. I knew he was hardworking.
Sam: How did you find him? Wasn’t he in college or something when you found him?
Pomp: He was working at Target.
Sam: He was working at Target.
Pomp: Literally working at Target. He would go into the bathroom on his lunch break and tweet Bitcoin charts. So I found him because of what he was tweeting. I reached out — what’s your background, what do you do? He’s like, I’m literally in the bathroom at Target tweeting on my lunch break. And I was like, all right, that’s pretty cool.
Will Clemente and Reflexivity Research [00:22:00]
Sam: All right, this is either a great underdog story or it’s going to be “how could you guys trust this guy?”
Pomp: We just started interacting online, then I started bringing him on the podcast, and I got to know him. He was young, he didn’t have a ton of experience, but his compounding rate of learning was off the charts. He would read a book in two or three days and send me “here’s everything I learned,” then read another one and do it again. The trajectory was not linear — it was exponential.
Sam: Why is a guy who’s this smart and this into learning working at Target in the first place?
Pomp: He was in college — Target was just his college job. He ended up dropping out and betting on himself. Eventually we were like, hey, maybe we should start a company together. We figured out the structure, put some money into it, and in the first six months got to 100K ARR. I think we’ll be at maybe 300 to 400K ARR after the first nine months, and hopefully a million dollars in the first year.
Sam: By the way, I’m looking at the site. I used to own this thing called Trends — trends.co — and we got that to be a good business. But you’re doing something very similar, except you’re not making the mistake I made of being too broad. You’re doing just crypto. And it’s $2,500 a year?
Pomp: And it’s not just a weekly newsletter. You get anywhere from four to six research reports per week, plus a weekly analyst call. We’ve got a bunch of these young crypto-native kids — most of them are under 25 — and they’re super smart. They’re in all the Discord channels, they really understand what’s happening in the community. Then you take someone like me who can help them package that into something consumable by large family offices, hedge funds, individual investors.
And not only do you get the research reports, you also get that weekly call where you can just ask questions. We literally have public company CEOs who are subscribers, and they get on the call trying to learn.
Building with Young Talent [00:27:00]
Pomp: When you have these internet-native businesses, there are pros and cons to working with young people. The good thing: they’re too naive to know all the things that would stop someone else from doing it. They have time, and they’re willing to make mistakes. They don’t get embarrassed. You say “don’t do that” and they go “okay, thanks,” and then just do something else.
The downside: at one point we literally had to have an internal session — here’s how you write, here’s how to use punctuation and spacing and all these things.
But you go into these businesses understanding that it’s all about momentum and the compounding rate of learning. If you set it up correctly, these businesses can grow to be pretty substantial and profitable. And the thing I enjoy most is — if I could go back and be 22 again, I don’t want to get a job. I want to bet on myself and use this internet thing to make more money than I could at a regular job doing the same skill.
In every business, I try to create upside. We take a portion of revenue or profit depending on the business, put it into a pool, and split it among the team. When you win, I win. When I win, you win. People will do incredible quality and velocity of work because the capitalistic incentive takes over — they want to make money, and they want to do good work to make that money. It aligns interests and these businesses can absolutely explode.
Sam: But why do five things instead of just one thing that could maybe grow faster with more of your focus?
Pomp: I am doing one thing. I provide capital and distribution. That’s the only thing I do. When I start the research business, Will and his team are doing the research. I’m really good at putting together the deals and the capital, and then pushing a high-quality product through my distribution — and hopefully growing that to not just my distribution but other people’s distribution.
I couldn’t run the recruiting business. I couldn’t run the research business. I have to stay within my circle of competence: provide capital, have a huge megaphone, pick correctly the people you’re going to do it with, and then get out of the way and let them be great.
Fear of Losing Relevance [00:33:00]
Sam: Shaan and I are in a similar spot to you. The thing I keep asking myself is: this is awesome, but when are people going to stop listening to me? When am I not going to be cool anymore? Do you get that fear — that your clout won’t matter?
Pomp: I’ve been on the internet long enough to go through peaks and valleys. In 2021 I could have literally tweeted “sup” and it was going mega viral during the Bitcoin bull market. Everything went viral. But that’s not me — you have to be grounded enough to understand that was the Bitcoin bull market. That’s not because I’m some genius.
And I have this saying: if you get the praise on the way up, you got to eat the stuff on the chin on the way down. So when FTX blew up and all this stuff happened, I went on national television and got grilled by a reporter for 20 minutes in a completely unscripted thing. He wasn’t friendly. But that’s where my skill set shines — I will debate anyone at any time on topics I understand, and it’s even better if it’s on live TV. Because what did we do? I went on television, did it, got off. Twitter was on fire — people were like “that was the greatest segment of all time.” I emailed them, said send me the video, immediately uploaded it to YouTube, titled it “Pomp Destroys TV Host on Bitcoin,” and published it.
Why go on television? To get the clips, to get the content, to then post on your own stuff.
Shaan: Right.
Pomp: And the hate — you have to realize the haters are actually on your marketing team. A guy yesterday created an entire thread of hate. He had videos, tweets. He literally filmed himself screen-recording unfollowing me. I almost DM’d him to say “thank you.” The more you attack people, the bigger the audience gets. I’m not seeking controversy or attacks, but if you have that lens, the haters are on your team. They just haven’t realized it yet.
Distribution Channels: Which One Matters Most [00:38:30]
Sam: What distribution channel is going to be the most effective for you? If you only had one — Twitter, email list, podcast, YouTube — which one would you say is the most powerful?
Pomp: The one I wouldn’t give up is email. But I don’t necessarily think it’s the one I’m most focused on growing.
I think audio is a really interesting medium because you’re basically whispering in someone’s ear for an hour. It’s super intimate and people really come to trust you. Someone out there is probably doing reps at the gym right now and listening to us.
Sam: We get that a lot.
Shaan: Someone’s literally at the bottom of a deep squat thinking “damn, these guys are calling me out.”
Pomp: You’re in people’s ears. Or with email, you have direct communication and you can write. If you understand what your best quality is — some people is writing, some people is video, some people is audio — you have to match that. I know people who have podcasts who script out every single word. I don’t think you guys do that.
Shaan: No.
Pomp: And if you guys did, one, it would take forever, and two, it wouldn’t be as entertaining. Because what makes this magical is the serendipity and the iterative nature you guys have back and forth. So if you guys were sending an email and you two wrote it — sorry, but it probably sucks. There’s no magic there. Because the magic here is the back-and-forth.
As people start to build audiences, you have to really question: where is my advantage and where do I have something that can cut through the noise? There’s so much noise now. If you don’t cut through, you might as well not start.
Shaan’s Milk Road Stories [00:45:00]
Shaan: I gotta tell you guys a hilarious story before we go. Pomp was talking about his analyst team — the high-quality analysts, two years out of undergrad. At Milk Road, we had a super lean team. It was me, Ben — I wasn’t active day-to-day, really just guiding — Ben was running it, and then Diego was our lead writer. He’s awesome.
We decided to try social media and put out a post: “I don’t know how to use TikTok, but if you do, come work for us.” So this guy Billy uploaded this incredible video — it’s on the internet, you can go look on Twitter. He basically found someone and said “can you hold this phone, I’m trying to get a job” and then chugged a full jug of milk shirtless. Just a ridiculous video.
Anyway, we hired Billy. We tried the TikTok thing, didn’t fully work out, but it was okay. Billy ended up helping write the newsletter too.
Two hilarious things just happened. First: they did a Milk Road team offsite — something we never did, because my whole ethos building Milk Road was I’m not trying to be a CEO anymore. I don’t want to stand up in front of the company in a branded t-shirt and tell everybody how great everything is. But the new guys who bought it want to do the company-building thing, so they invited everybody out.
I asked Ben: “How was the offsite?” He had one insight from the whole thing. He goes: “Billy showed up in a wife-beater. Not as a joke. That’s just what he wore to the event. And no one said anything.”
Sam: No one said anything?
Shaan: No one said anything. And then — fast forward three weeks — they offered Billy a raise and he quit instead.
Sam: Wait. He got a raise and quit?
Shaan: He got a raise and quit. Ben texts him: “Billy, you got a raise — what’s the plan?” He replied in a text message: “Do I look like a guy with a plan?”
Sam: That’s the most badass thing.
Shaan: That became the most badass thing I heard all week.
The Value of Hiring Young, Internet-Native People [00:49:00]
Pomp: I tend to think we over-index a lot on wanting to hang out with our heroes — the older people who’ve done the thing we’re trying to do. There’s a lot of value in that. But we dramatically under-index on: go find the young, energetic person who you’re like “you are literally an idiot, but damn you’re going to be an awesome idiot who runs through 20 walls and eventually finds something on the other side.”
And what it does is it forces you to up your game. Have you ever talked to a 21-year-old and you say “let’s get this done by Wednesday,” and they send it back to you two hours later? And you’re like, damn, why did we wait until Wednesday? This kid is actually correct — we should just get it done now.
Internet-native companies have a big advantage in that. I don’t know — it wouldn’t surprise me if we bankrupt main street businesses because they all move online as people realize: why do I have a physical store when I can do this? It’s a big concern for local communities, but there’s way more economic opportunity online for people who want to pursue it.
The Shaan Story: Almost Hired Frank DeGods [00:52:00]
Shaan: One of the other guys we tried to hire at Milk Road — a young guy, 20 or 21 — was working at a Main Street job. I loved his tweets. He would post these little random websites he was making on the weekend that were just super simple. Like, it’s either going to go viral or it’s the dumbest thing ever. No in-between.
I told Ben: “We should hire this guy.” Ben goes, “What’s he going to do?” I go, “I don’t know. Just have him do what he’s doing now but without the full-time job. What if we gave him more time to do the stupid stuff he does on the weekends?”
So I talked to him. It was super early — we were like four weeks into Milk Road. I said, “I think this thing’s going to work, you should join.” He said, “What am I going to do?” I said, “Just do Rohan stuff. Go do that.”
He said, “All right, when do you want to start?” I said, “No, I’m traveling, I’ll be back Wednesday. Let’s talk Wednesday.” Which was four or five days away.
Fatal mistake. Classic 34-year-old mistake thinking the world’s not going to change in four days.
In those four days, this guy launches an NFT project that goes super viral. He makes so much money that he becomes an anonymous account — Frank DeGods — and he created the D-Gods project.
Pomp: I can talk about it now because he’s come out publicly. But for a while I was like, what the hell is going on? I kept trying to hit him up: “Dude, what happened?” I didn’t know he was the guy behind D-Gods. I was like, “Dude, you ghosting me? We had such a good idea.” He resurfaced like three weeks later: “Sorry bro,” like no time had passed. “Oh yeah, about that — I’m doing this other stuff now.”
I was like, tell me about it. He screen-shared and showed me how he was growing it. One thing I’ll never forget — the classic “this guy’s an idiot, this makes no sense, but I’m down and I want to be in this car.”
He shows me the site and I go, “How do you stop people from just selling it right away?” Because nothing holds value unless the people who buy it hold. For Bitcoin, the genius meme is the HODL meme — it became culturally normal to just hold the thing.
He goes, “Oh yeah, I had the same thought, so I created something called the paper hands tax.” If you sell for less than the mid price, not only do you take the loss on the principal, but we also apply a 25% tax because you had paper hands. People loved it. It totally worked. He created a meme and it was a monetized meme. I thought it was awesome.
Shaan’s DMs: The Frank DeGods Instagram Story [00:59:00]
Shaan: While all that was happening, I just looked at my DMs, and I have another perspective on the exact same situation. One of the hacks people have figured out: if they post something on their Instagram story, bigger accounts sometimes just share it, but in the DMs it looks like they messaged you. So now it looks like they posted something and you responded.
He did that — he posted something, I reposted it. Then he followed up. He’s going to kill me for reading this out loud. He goes: “If you have any ideas for some more fun tools for us to make that you think would be helpful, would love to chat, man.”
And I replied. That’s how we had our first conversation. He was just doing his thing, getting into people’s DMs, trying to hustle, and it worked.
Pomp: That’s the thing about these young internet-native people. They find ways.
Shaan: And I missed him. He got away. Four days — I waited four days.
Sam: You let that fish get away.
Naps, Sleep, and Energy [01:03:00]
Sam: Do you nap? Are you a napper?
Pomp: No. Hell no.
Sam: Why would you nap?
Pomp: Stuff to do. Why would you nap?
Sam: Oh, do you guys both take naps?
Shaan: Yeah. I’d nap every other day at 99. Once I get to every day, I know I’ve made it.
Pomp: How many hours do you guys sleep at night?
Sam: Seven normally.
Shaan: Same.
Pomp: I don’t think I could nap during the day, but I also drink coffee in the morning, so I might be screwing it up.
Shaan: That’s probably it.
The Facebook / Flavor Flav Story [01:05:00]
Shaan: I’m just going to share a quick story. When I was at Facebook, we had just opened up the new headquarters. We did this big event, kind of an opening-party type thing. As a thank you to employees and also to show off the new campus, they brought in a bunch of celebrity performers.
I had a different role that day — I was basically doing like PR and helping move celebrities around. One of them I ended up with was Flavor Flav. So I’m like walking around with him, kind of nervous because he’s a celebrity. Is he cool? Is he not? Whatever.
We do the event. At the end, he goes: “Yo, before I leave — where’s that Instagram doodad?”
And I was like, ”…What?”
He goes: “The Instagram dude. Where is he? I know he works here.”
And I was like, “Do you mean like the founders?”
He goes: “Yeah, the tall one. I met him. I know him.”
And I was like, “Oh boy.” I was like, “Uh… Kevin?”
He goes: “Yeah, that one.”
So I genuinely know where the Instagram team sits. I walk through the whole campus. We get there and I’m like, please don’t be at your desk, please don’t be at your desk, please don’t be at your desk. I’ve never talked to the guy before. And sure enough, he’s there — taller than everyone, you could see him the second you walk in.
I’ve got Flavor Flav with me. I walk over and go: “Uh, excuse me, Kevin…” He looks up, super nice, and Flavor Flav just goes: “What’s up. Yo, you need to turn my volume up on Instagram.”
And I’m like, I am definitely getting fired. Holy — this is so bad.
Kevin was a consummate professional. He goes, “Let me introduce you to our partnerships team,” or whatever. And I remember on my way out I was like, “Hey man, sorry about that. Did you know him?” He was like, “I think we met one time like five years ago at a party. But sure.”
Sam: So good.
Shaan: If you ever get to talk to the leaders of any of these products, that’s the question you gotta ask. Shoot your shot. “Yo, turn my volume up.”
Sam: That’s my new phrase. That — and “do I look like a guy with a plan?” Those are just epic.
Sam: All right, fellas — appreciate it. Thank you.