Sam Parr, Founder of The Hustle: How He Built The Hustle to $10s of Millions in Revenue

Sam Parr is the Founder and CEO of The Hustle, a new age media company that uses email to deliver information to young people. In this conversation, Sam and and Anthony discuss launching The Hustle, gaining over 1 million subscribers so quickly, what makes a great email newsletter, getting fired from Airbnb the day before he was suppose to start, and why great entrepreneurs usually bet on themselves. BLOCKFI-----BlockFi allows you to keep your crypto, put it up as collateral, and receive a USD loan funded directly to your bank account. They do loans ranging from $2,000 to $10,000,000, and they're perfect for helping you reach your financial goals of all sizes. Visit BlockFi.com/Pomp to learn more about putting your crypto to work without having to sell it. UNSTOPPABLE DOMAINS-----Make your crypto currency payments simple and build censorship resistant websites. Visit unstoppabledomains.com and purchase your blockchain domains today! -----If you enjoyed this episode and want to stay updated on everything Bitcoin, blockchain, and crypto. Check out Off the Chain newsletter by visiting offthechain.substack.com and join 35,000+ other investors currently subscribed to my daily investor letter.

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

• 0:00Anthony Pompliano?

  What's up everyone, this is Anthony Pompliano. Most of you know me as Pomp. You're listening to Off the Chain, simply the best podcast in crypto. Let's kick this thing off.

• 0:10Anthony Pompliano?

  Sam Parr is the founder and CEO of The Hustle, a new age media company that uses email to deliver information to young people. In this conversation, we discuss how The Hustle was launched, what makes a great email newsletter, how Sam and his team grew to 1 million subscribers so quickly, how Sam got fired from Airbnb the day before he started, and why great entrepreneurs usually bet on themselves. This episode was a lot of fun to record, and I hope you enjoy it. But before we get into the episode, I want to talk about the two sponsors that made this possible as well. The first, BlockFi. You know I love these guys. If Bitcoin and cryptocurrencies have any chance of ever becoming the next global reserve currency, we're gonna need a lot of infrastructure and wealth management services built. It's exactly what BlockFi is doing. As many of you already know, I'm a huge fan, I even invested, and

• 0:55Anthony Pompliano?

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• 1:40Anthony Pompliano?

  rather than cash back or loyalty points. A Bitcoin rewards credit card not only sounds dope, but should help more people earn Bitcoin for their everyday purchases, too. So BlockFi has been a longtime supporter of Off the Chain Podcast, and I'm a huge fan. Go to blockfi.com/pomp. Again, blockfi.com/pomp. One more time, blockfi.com/pomp, and check them out. There may even be some discounts and surprises when you head on over to blockfi.com/pomp. Now, the second sponsor for this episode is Unstoppable. Unstoppable Domains, that's right, unstoppable domains. Many of you probably have heard about YouTube taking down crypto-related content, or Metamask getting removed from the Google Play Store. Well, the decentralized web is going to clear up all of that.

• 2:23Anthony Pompliano?

  It's going to make censorship impossible. That's right, there's lots of companies working on it, but you can go to unstoppabledomains.com and get a .crypto domain today to build a decentralized website. You can also use that .crypto domain to get paid. I've got pomp.crypto and I use it to get paid. This is a huge improvement for sending Bitcoin and everyone and every wallet should use it. You can already go to Trust Wallet, Atomic Wallet, and Coinomi right now, type a .crypto domain into the send field and pay someone. In order to onboard the next billion people, we can't be talking about hex addresses anymore. Bitcoin's just too hard that way. Everyone uses domain names. It's a system that everyone who's been on the internet already understands.

• 3:05Anthony Pompliano?

  Additionally, Unstoppable Domains just launched a brand-new browser, unstoppabledomains.com/browser. Go to unstoppabledomains.com/browser. They've built this browser to help everyday people with no technical insight like me access the decentralized web. Head on over to unstoppabledomains.com/browser and give it a try. Takes seconds to get onboarded and next thing you know, you'll be down the rabbit hole in the decentralized web. Unstoppabledomains.com/browser. Don't forget, Off the Chain's not only a podcast, I also write an email every single morning. I wake my ass up, I work really hard, I say smart things. So go subscribe. Offthechain.substack.com.

• 3:49Anthony Pompliano?

  Again, Offthechain.substack.com. Now, let's get into this episode with Sam and I hope you enjoy it.

• 3:55Speaker 01

  Anthony Pompliano is a partner at Morgan Creek Digital. All opinions expressed by Pomp or his guests on this podcast are solely their opinions and do not reflect the opinions of Morgan Creek Digital or Morgan Creek Capital Management. You should not treat any opinion expressed by Pomp as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his opinion. This podcast is for informational purposes only.

• 4:21Anthony Pompliano?

  Alright guys, bang bang. I've got Sam here. We got a whole bunch of shit to talk about. You guys are absolutely killing the game. Thanks for coming to do this.

• 4:29Speaker 02

  Thank you, I'm excited.

• 4:30Anthony Pompliano?

  This all came together because you tweeted, "I'm in New York and I have nothing to do. Who wants to meet?" And I was quick with the Twitter fingers.

• 4:36Speaker 02

  Yeah, and in that like same Twitter thing, tweet storm, I said I was gonna be here and someone was like, "Host a meetup." And I was like, "Okay, we'll do it for our trend subscribers." And we got like a couple hundred people who are RSVP'd, and so we had to trim it down to 20, yeah.

• 4:54Speaker 02

  Yeah, and so we'll see what happens tonight.

• 4:58Anthony Pompliano?

  Let's talk about your life before the hustle. What did you do? Where did you come from?

• 5:04Speaker 02

  Well, you said you're from the south, right?

• 5:05Anthony Pompliano?

  Yep, North Carolina.

• 5:06Speaker 02

  I grew up in St. Louis, Missouri, and then when I was 18, I moved to Nashville, Tennessee for college.

• 5:11Anthony Pompliano?

  Okay, where'd you go?

• 5:12Speaker 02

  Vanderbilt. No, I wasn't good enough. I went to the worst version, overpriced, below-average school called Belmont University.

• 5:22Anthony Pompliano?

  Aren't they all below-average and overpriced?

• 5:24Speaker 02

  No, I think that a top 10 or top 20 university, I think it's worth it actually. Like, I'll tell my kids, like, "Go to state school or go to Ivy League."

• 5:31Anthony Pompliano?

  Okay.

• 5:31Speaker 02

  It's one or the other.

• 5:32Anthony Pompliano?

  Yeah, yeah, yeah. Kind of a bell curve type approach to life, alright.

• 5:35Speaker 02

  And my wife went to an Ivy League school and I see the benefits.

• 5:39Anthony Pompliano?

  So she's smarter?

• 5:41Speaker 02

  She's very smart. And I got a track and field scholarship, so that's why I went there.

• 5:46Anthony Pompliano?

  What sport?

• 5:46Speaker 02

  400 meter.

• 5:48Anthony Pompliano?

  Okay.

• 5:49Speaker 02

  One lap.

• 5:50Anthony Pompliano?

  Tyrone Ross claims to be the fastest guy in all of tech and finance. You might have to give him a little raise.

• 5:55Speaker 02

  What's he run? What's his race?

• 5:57Anthony Pompliano?

  I don't, 400 is what he's run.

• 6:00Speaker 02

  Fast anymore, but I bet I would beat him.

• 6:04Anthony Pompliano?

  So this is the part where I sandbagged a little bit. He was training for the Olympics, and I think he got hurt or something, but I think I'm gonna have to set this up. People would pay to come see him.

• 6:13Speaker 02

  How old is he?

• 6:15Anthony Pompliano?

  I'm gonna guess he's late twenties to early thirties.

• 6:19Speaker 02

  Ah, okay. Tyrone Ross, I don't think I know that name. I mean, I ran like 47, 48 in the 400, which is better than most.

• 6:26Anthony Pompliano?

  That's pretty fast.

• 6:26Speaker 02

  I was a spectacular high school runner, an average college runner.

• 6:30Anthony Pompliano?

  Yep.

• 6:30Speaker 02

  But if you're an average D1 athlete, you likely can beat a normal person, but I don't, this guy might sound legit.

• 6:36Anthony Pompliano?

  We're gonna set this up now.

• 6:37Speaker 02

  I'm not fit though now. I'm trying to get fit, but it depends how fit he is.

• 6:41Anthony Pompliano?

  Alright, so you go to school, track and field.

• 6:43Speaker 02

  Yeah, then I met this guy named Mike Wolf. Remember that? Maybe you do. Oh, you're from the south, you'll know. American Pickers? So the main guy, Mike, I met him on the street and I was a fan and I just walked up to him.

• 6:52Anthony Pompliano?

  No way.

• 6:53Speaker 02

  Yeah, I started shooting the shit and he was like, "I'm opening up the store here and we're gonna record here." I go, "Mike, let me work there. Let me run it."

• 6:58Anthony Pompliano?

  Yep.

• 6:59Speaker 02

  And he was like, "Well, not run it, but come work." Okay, so I worked there.

• 7:02Anthony Pompliano?

  And American Pickers, for those that don't know, is a show on television where they basically went to like, random people's backyards, garages, whatever.

• 7:09Speaker 02

  And buy old motorcycles, old cars, gas pumps, anything old and cool.

• 7:13Anthony Pompliano?

  Whatever cool shit they could find.

• 7:14Speaker 02

  Yeah, like things that you would see in like an Americana style home.

• 7:17Anthony Pompliano?

  Yep.

• 7:17Speaker 02

  We would rent stuff, the music videos, country music videos, just cool stuff. And it was the second most popular show on cable at the time.

• 7:22Anthony Pompliano?

  Wow.

• 7:23Speaker 02

  Yeah, it was, it went like Pawn Stars, American Pickers, and then like David Letterman.

• 7:27Anthony Pompliano?

  What does that say about our society?

• 7:28Speaker 02

  Dude.

• 7:29Anthony Pompliano?

  That Pawn Stars was number one.

• 7:31Speaker 02

  I mean, those guys are rednecks and I'm a redneck, so I could say it, but it's really educational.

• 7:35Anthony Pompliano?

  Yeah.

• 7:35Speaker 02

  We had children from all over the world that would come. People loved it.

• 7:39Anthony Pompliano?

  Well, so my favorite part about Pawn Stars actually was, it has very similar elements like a shark tank. Cause there's the negotiation factor and I think people are really, really drawn to the negotiating.

• 7:47Speaker 02

  Yeah, I mean, look, it's a, it was like, appears like this, like one thing, but in reality, it's an educational, family-friendly. It was great programming and people loved it. And we would have, it was a small store, maybe 4,000 square feet, pretty, maybe 3,000, pretty small. But we would get thousands of people who would wait in line, who'd come from all over the world.

• 8:07Anthony Pompliano?

  Line around the block.

• 8:07Speaker 02

  Yeah, and, and it was in an area without a lot of stuff. And so I was like, "I should do something about this." So I opened, opened up a hot dog stand that expanded to multiple locations. It was called Southern Sam's, the wiener's as big as a baby's arm. And, uh, yeah, um, that's where I learned how to do marketing and...

• 8:25Anthony Pompliano?

  Where, where did that name come from and the slogan? Who thought of that? You?

• 8:28Speaker 02

  Yeah, I don't know. I just get, and then we would like give people discounts if they put their baby's arm in a bun with mustard on it. And it was like, that's funny. Um, and so...

• 8:37Anthony Pompliano?

  What years? Is this pre or post social media being popular?

• 8:40Speaker 02

  Uh, right around, 2010.

• 8:42Anthony Pompliano?

  Okay, alright, so people could be sharing it on Facebook or whatever.

• 8:45Speaker 02

  Yeah, I don't even think Instagram was around, or maybe it just started, but yeah, that was the point. Um, and so I opened that up and then I started playing around the internet and I learned how to make money on the internet. Like I would open up like little ecommerce stores that would do okay. And I was like, "The internet's where it's at." And so I was a junior, senior in college and...

• 9:04Speaker 02

  I was like, I need to move to wherever the internet people live, which I had never been to California. I didn't know anything. And I

• 9:10Anthony Pompliano?

  Internet people, where are they?

• 9:12Speaker 02

  And I, there was this runner named Chris Lukasek. I don't know if I ever even said this, his runner named Chris Lukasek. And he was a professional runner and he quit running at his peak to join this thing called Airbed and Breakfast. And I was like, what's this thing about? And so I emailed the founder and got a job interview. And he was like, yeah, you could work here, come work here. And so I dropped everything and moved out to San Francisco and

• 9:32Anthony Pompliano?

  And Brian Chesky was who you emailed?

• 9:33Speaker 02

  Joe, Joe. And it turns out the day, so I left school, sold everything. I hadn't graduated yet. I got out there and the Sunday before I was supposed to start, they go, your job was rescinded, your job offer, we took it away. And it was because I lied on my resume. I had a criminal record, I had a misdemeanor and I didn't tell the truth. And so I did not tell the truth, but like I somehow like vaguely, I was like, yeah, technically I'm telling the truth, but they caught it.

• 10:00Anthony Pompliano?

  Yep.

• 10:02Anthony Pompliano?

  Are you like, oh shit? Or are you just like, what are you thinking?

• 10:05Speaker 02

  I was, it was about three hours where I was just so depressed and No, it actually happened on a Saturday and I was flying out that day and my mom had come down to help me move out.

• 10:15Anthony Pompliano?

  Okay.

• 10:15Speaker 02

  And we, and I was with her when we found out and she was like, let's get on the plane anyway, you'll figure it out. So I flew out there.

• 10:20Anthony Pompliano?

  What a great mom.

• 10:20Speaker 02

  It was very supportive and she, and, and she goes, just start, start something when you get out there, you'll figure it out. So I went out there, I started, I met a guy just randomly and he had, was a few months into starting a project. I joined him as a co-founder and it was a roommate matching company.

• 10:35Anthony Pompliano?

  Okay.

• 10:36Speaker 02

  Not sophisticated, made okay money, but we sold it for a little bit of money, not a lot, like tens of thousands, hundreds of thousands. And then after that is when I met Eric Bond, who you and I were talking about, and he had a conference called HustleCon.

• 10:48Anthony Pompliano?

  And I knew, I knew Eric, sorry to interrupt, but I knew Eric from when I worked at Facebook, had no clue that he had the conference. I just knew him as, you know, a colleague at Facebook.

• 10:56Speaker 02

  It was small, maybe like 50 or 100 people, I don't even remember how many people, but it was a pretty small thing. And I was like, Eric, I like, what do I do? What should I do? And he was like, well, I got this thing you could kind of play with. And so I kind of, I took the original idea that he had and the domain name and I kind of changed. It a little bit and I launched this thing called HustleCon, which is like a TED Talk-ish for entrepreneurs. That's how I explained it to my parents who didn't understand uh this game. But it was like a conference for non-technical founders.

• 11:26Anthony Pompliano?

  And it was called HustleCon.

• 11:27Speaker 02

  HustleCon.

• 11:28Anthony Pompliano?

  Which the whole idea of like hustle in uh some people listening to this won't remember when the days when the word hustle was not a bad word.

• 11:35Speaker 02

  It was like hustler or thief.

• 11:37Anthony Pompliano?

  Yeah, well, there it was again bell curve, right? Like there was days where hustler was a bad thing and they were gonna steal your wallet. Then it was like if you're a hustler, that means that you're just super ambitious self-starter. Like you're gonna go knock down doors and be successful.

• 11:49Speaker 02

  Yeah.

• 11:49Anthony Pompliano?

  And then it kinda went into like the hustle porn world of like everyone's a hustler. And you know, if you use that word, then all of a sudden now you're a bad person.

• 11:56Speaker 02

  Yeah.

• 11:56Anthony Pompliano?

  Right? So this was in like the twilight days of the word hustle.

• 11:59Speaker 02

  Yeah, and I think that we've done good with the word, but it it it was good. And so like I I quit my job and on the on the first day of investing where it ended and I started this thing. And the idea was I'm just gonna do it to kill time.

• 12:13Anthony Pompliano?

  Yep.

• 12:14Speaker 02

  And until I find my next business. And I launched it on June 1st and the event was on July 15th or something like that. I only had six weeks and I use an email newsletter. I'm a self-taught copywriter. I got really good at copywriting through a lot of self-practice and everything. And it made like 60 grand and I was like, that's kinda cool. Let's do it again.

• 12:34Anthony Pompliano?

  That's more than like half of America makes.

• 12:36Speaker 02

  Yeah, it was great. It was really great and I didn't know that it was gonna make money. I didn't mean to, I mean, I did not mean to, but it just was better than expected. And I did it again, this next time it made like a quarter of a million. And so.

• 12:45Anthony Pompliano?

  And how how long are you waiting in between iterations?

• 12:48Speaker 02

  I did the first one and I started working on it in June. I did it, I took the money and put most of it in the bank. I gave myself five grand and I went and traveled the country on my motorcycle for like five months.

• 12:59Anthony Pompliano?

  Cause like. American picker style.

• 13:00Speaker 02

  Yeah, that's what I did. I just and I camped and I just did nothing. I just, I just explored and read books and well.

• 13:06Anthony Pompliano?

  And at the time, are you like, I fucking made it? Like, are you like, I came all the way here and.

• 13:12Speaker 02

  A little.

• 13:13Anthony Pompliano?

  I made 60K, I'm on my motorcycle.

• 13:15Speaker 02

  And I had already made a little bit of money from my other thing. And so like I was like, cause I was like a little bit of a weirdo in high school and grade school. Cause I was always making money on YouTube or selling shit. And I was like, fuck those guys, like I did it.

• 13:28Speaker 02

  Am I allowed to curse here, sorry? I was like, fuck those guys.

• 13:30Anthony Pompliano?

  You can say whatever you want.

• 13:31Speaker 02

  And then like my high school wrote a article about it and I was like, gotcha. Cause they were, I was not a great student, so they were right, but I was an asshole.

• 13:39Anthony Pompliano?

  Every bad student who ends up doing anything successful has that moment where something that their high school does to like recognize them because they want to promote their alumni, whatever. You're like, man, if the people reading this right now only knew that the teachers thought I was going to be nothing, blah blah, whatever.

• 13:54Speaker 02

  Well, look, they were, I mean, I was not innocent. I was just, I was a punk because I was an angry teenager, but I was very happy when it started working out. So yeah, that's when I started getting a little bit of, a little bit of fame amongst my like hundred friends or something like, you know, they like knew like, oh, maybe this guy's not like.

• 14:14Anthony Pompliano?

  Maybe he actually knows what he's doing.

• 14:15Speaker 02

  Maybe like he's doing okay. And so on that trip, I read the biography of Ted Turner.

• 14:19Anthony Pompliano?

  Yep. Oh, it's a great one.

• 14:20Speaker 02

  Yeah, he's from the south. I was from the south, kind of Missouri, Tennessee.

• 14:24Anthony Pompliano?

  Hold on a second. Can we count Missouri as the south?

• 14:27Speaker 02

  Up here, they'll call it that.

• 14:28Anthony Pompliano?

  Oh, in New York, or yeah, well, anything south of like Pennsylvania is the south.

• 14:32Speaker 02

  Yeah, that's why I said kinda. I identified as a Tennessean because I lived there for a long time.

• 14:36Anthony Pompliano?

  Yep, that's fair. Okay.

• 14:37Speaker 02

  I, Missouri folks are, not to you, but to like Californians, they're kind of rednecky and I embrace that.

• 14:44Anthony Pompliano?

  Yeah. The only other person in tech that I know from St. Louis is Jack Dorsey, right?

• 14:49Speaker 02

  Yeah, and Sam Altman.

• 14:51Anthony Pompliano?

  Ah, okay. You got, that's good crew to be around.

• 14:54Speaker 02

  Yeah, Jack grew up in my neighborhood or went to high school in my neighborhood. So yeah, not really the south, but to some people it is. Maybe technically it's south of the Mason Dixon line, but I don't know. It was a, it wasn't a slave state, so.

• 15:08Anthony Pompliano?

  Okay.

• 15:09Speaker 02

  Who knows?

• 15:10Anthony Pompliano?

  Yeah, yeah, yeah. All right. So, okay, so you ride around on your motorcycle.

• 15:14Speaker 02

  Oh, and I read his book and I was like, this guy's from the south and he's kind of like shoots from the hip and he created CNN and I don't care if you're a Fox News guy or a CNN guy, what you can't deny is that CNN has impacted culture.

• 15:24Anthony Pompliano?

  Absolutely.

• 15:25Speaker 02

  And that was really fascinating to me because when I was on my trip, I would go to really poor parts of Nevada, poor parts of Alabama, poor parts of California, all over the world. And I'm like, well, I've been living in California with all these sophisticated people, yet like we're all the same, we're all just people.

• 15:40Anthony Pompliano?

  The, the difference in cultures couldn't be more contrasting.

• 15:46Speaker 02

  Yeah, well.

• 15:47Anthony Pompliano?

  The part that's so crazy to me is, did you read, was it a hillbilly?

• 15:50Speaker 02

  Eulogy.

• 15:51Anthony Pompliano?

  Yeah.

• 15:52Speaker 02

  Right, elegy.

• 15:52Anthony Pompliano?

  Elegy, I don't know. People always make fun of me because I can't say that word.

• 15:55Speaker 02

  They're in the Appalachian Mountains.

• 15:57Anthony Pompliano?

  And like you read this thing.

• 15:58Speaker 02

  So I knew people like that.

• 15:58Anthony Pompliano?

  Yeah, and you read this thing and you're like, you know what? Like, actually, a big portion of the population lives in a similar type of situation. It's very different than a San Francisco, New York, LA, whatever. But at the end of the day, we're all humans and we all actually share a lot of the same interests. We share a lot of the same desires, bias, emotions, etc.

• 16:14Speaker 02

  And the fact is, it's the same amount of, same people in every place. So like, for example, people always say in the South, it's all redneck. Go to Birmingham, Alabama, it's all hipsters. Go to Austin, Texas, it's all hipster. Go to Portland, it's all hipsters. Go to the suburbs of Birmingham or the suburbs of Portland. It's just families who are just trying to pay the bills and raise good kids. Go to the rural part of Oregon, the rural part of Northern California, the rural part of Texas, and it's just rednecks. It's all the same shit.

• 16:39Anthony Pompliano?

  Yep.

• 16:39Speaker 02

  Right? And when I did-

• 16:40Anthony Pompliano?

  They just talk a little different in each area.

• 16:42Speaker 02

  They just, not even. You talk, go to, go up north in California and they've got Southern accents. Go to Bakersfield and they all talk the same.

• 16:49Anthony Pompliano?

  Yeah.

• 16:50Speaker 02

  It's kind of weird. Like, and so during this trip, I was like, I want to create something big that can impact all these people or get really rich where like, I can like, have my, I just want to have a, a big impact, to impact people out here and not just in San Francisco and not just New York, but everywhere. And so-

• 17:06Anthony Pompliano?

  There's, there's two ways to do the media thing. Either you build it from scratch and you make it successful or you're the richest man in the world, like Bezos, you just buy the Washington Post.

• 17:13Speaker 02

  There, yeah. And so I was like, one of those things is really interesting. And so I decided to, I did HustleCon again and that was in April, so I waited nine months about, did again and that made money. And I was like, I'm using all this money, I'm gonna start a-

• 17:24Anthony Pompliano?

  What year is this?

• 17:25Speaker 02

  Information company.

• 17:26Anthony Pompliano?

  Like 2016, 17?

• 17:28Speaker 02

  Yeah.

• 17:28Anthony Pompliano?

  Okay, got it.

• 17:29Speaker 02

  Yeah.

• 17:30Anthony Pompliano?

  So you're gonna create the information company?

• 17:32Speaker 02

  Yeah, and then, so we launched The Hustle. We originally launched it in, um, uh, fall of 2015 and, but in earnest, we really went at it in, uh, April of 2000, whatever it is, we're gonna be four years old this April.

• 17:49Anthony Pompliano?

  Okay, 16. Yeah, okay.

• 17:51Speaker 02

  So in earnest.

• 17:52Anthony Pompliano?

  I'm not a mathematician, but 20 minus 4 is definitely 16.

• 17:55Speaker 02

  April 19th of 2016. That's when we really went hard. So I can, so, so as a project off and on, I've been working on this for a while.

• 18:03Anthony Pompliano?

  Yep.

• 18:03Speaker 02

  As the company that we're known for now, April of 2016.

• 18:09Anthony Pompliano?

  Okay, and the original idea is what? When you say I'm gonna go after this information company?

• 18:13Speaker 02

  Well, the original idea was I'm gonna build up this huge audience of entrepreneurial type folks, people who want to put their debt in the world through business, and then I want to create more products for them.

• 18:21Anthony Pompliano?

  Okay.

• 18:22Speaker 02

  And I didn't want to raise money, and so I did a ton of research, and I realized that, two things. One, email was the best platform to build a business on, because it wasn't owned by one person. You know, if you build a business, if you build a business on Facebook, it's like you are building your store where the real estate, or the landlord ups the rent every month. I was like, okay, not gonna do that. So email seemed the best.

• 18:43Anthony Pompliano?

  Or in Facebook's case, they take away real estate as you continue trying to grow.

• 18:47Speaker 02

  Yeah, they decrease the reach.

• 18:48Anthony Pompliano?

  Yep.

• 18:49Speaker 02

  And make you pay. And so, and...

• 18:51Anthony Pompliano?

  I'm the only person who's allowed to say that, because I ran, along with a number of other people, the growth team for Facebook pages, and I saw it in real time.

• 18:57Speaker 02

  Oh, you ran that?

• 18:58Anthony Pompliano?

  As people were complaining. Yeah, I was the product manager, we had an engineering manager, etc. There's a cohort of people leading this team. And Facebook had said to people, hey, come on, like, put your business, you know, create all this content. And then over time, it, not intentionally, not to hurt the businesses, but it's just more and more businesses join, there's only so much news feed.

• 19:15Speaker 02

  Yeah, it's just supply and demand.

• 19:15Anthony Pompliano?

  Yeah, exactly. But what do the small business say? Small business persons out there with their pitch fork, like, you took away my reach.

• 19:21Speaker 02

  Yeah, I'm not anti-Facebook. I own a lot of Facebook stock. I love Facebook. I pay them a lot of money, I love Facebook. Um, I, but, like...

• 19:28Anthony Pompliano?

  But it happens, you have the platformers.

• 19:30Speaker 02

  I ain't gonna hate the player, right?

• 19:31Anthony Pompliano?

  Yeah, you have the platformers, whether it's Facebook, Twitter, Google, wherever.

• 19:33Speaker 02

  Yeah, they're just winning the game. Um, and so, uh, oh, so I looked at the reach on Facebook and all that, and rented real estate. But then I also saw another thing, which is, if you talk to a lot of econ folks, they'll tell you that email's the most powerful channel. So I was like, I'm gonna build up this huge audience of a like-minded group of people, and I'm gonna monetize with email advertising, because the email ad rates are super high, because it has the highest click-through rates and the most engagement. And then I'm gonna create more products and services for that one group of people, and then I'm gonna use all the profit from my advertising business to launch those to that audience, and... Hopefully, reach world domination, starting with email.

• 20:07Anthony Pompliano?

  So, you saw this much earlier than most people saw, but basically what this whole idea, and this is coming, there's a million examples we can talk through, is the idea of if you build a really rabid, engaged, like, highly, kind of, powerful audience, once those people subscribe to what you stand for, what you're doing, etc., there's all kinds of different ways to monetize that audience.

• 20:28Speaker 02

  Yeah, the easiest example is, look at the Kardashians, you know, the, I always forget their names, but the Jenner woman who is a billionaire because-

• 20:36Anthony Pompliano?

  Kris Jenner, yep.

• 20:37Speaker 02

  Well, the mom, I'm talking about the daughter, the one who had the makeup that sold her-

• 20:42Anthony Pompliano?

  Kylie.

• 20:43Speaker 02

  Yeah, okay.

• 20:43Anthony Pompliano?

  I feel like I'm taking a quiz right now. All right, go ahead. So Kylie Jenner-

• 20:47Speaker 02

  She had one with Instagram, and she sold makeup on it, and it became a multi-hundred-million-dollar-a-year business that was valued at multiple billion dollars.

• 20:54Anthony Pompliano?

  Yep.

• 20:54Speaker 02

  That's the game. It's very simple. That's what we were gonna do. And so-

• 21:00Anthony Pompliano?

  How do you, so you start this email, how do you grow the email? Because most people say, "Hey, that's a great idea, I'm gonna go do that," but they don't get to a million subscribers.

• 21:07Speaker 02

  So, when I started this industry, this business, and kinda still, I knew nothing about media.

• 21:12Anthony Pompliano?

  Okay.

• 21:13Speaker 02

  Nothing.

• 21:13Anthony Pompliano?

  That's actually probably an advantage.

• 21:14Speaker 02

  It was totally an advantage, because people would be like, "Wow, you're breaking the rules." I'm like, "I don't fucking know what the rules are." I'm not, I'm not trying to be a badass, I just don't know anything, I'm an idiot.

• 21:23Anthony Pompliano?

  Yeah.

• 21:23Speaker 02

  And, but, what I knew how to do, from years of studying, and years of selling hot dogs, and years of just salesmanship, is I knew how to get people to believe what I wanted them to believe. I knew how to capture-

• 21:35Anthony Pompliano?

  It's a fantastic skill.

• 21:36Speaker 02

  Look, that sounds negative, but I'm using it in a good way.

• 21:40Speaker 02

  But, I knew how to get people to, I knew how to capture their attention and their emotions.

• 21:45Anthony Pompliano?

  So, Scott Adams has done a fantastic job over the last couple of years dissecting this idea of like, weapons-grade persuasion, right?

• 21:52Speaker 02

  Yeah, he did it with Trump, where he's like, "Here's why Trump is..." And so, I knew how to do that just by talking to someone. I knew like, what to do. And so, I was a self-taught copywriter. I locked myself in the bedroom for six months, and I would just take the bestselling books, bestselling sales pages of all time, and I would copy them out by hand. And that's why I learned how to become a really good copywriter.

• 22:10Anthony Pompliano?

  And so, like, when you're doing that, what are you learning exactly?

• 22:13Speaker 02

  So, you, think about this, you play an instrument?

• 22:15Anthony Pompliano?

  Uh, I can drum on the table, but that's about it.

• 22:18Speaker 02

  Okay. Well, if you learn how to play guitar, usually what you do is you don't like start writing songs. You start learning other people's music, whether it's sheet music or you like turn Green Day on. You're like Billy Joe, where's he putting his fingers? Okay, I'll learn that song.

• 22:30Anthony Pompliano?

  Yep.

• 22:31Speaker 02

  And then I'm gonna learn Jimi Hendrix and then Nirvana. And you start seeing the patterns that make a successful song. And then eventually you say, alright, I understand what I like and I understand best practices for this type of genre and this type of genre. I can combine here, here, here and make my own song. That's what copyrighting, that's my methodology for like copyrighting. So I'm like, alright.

• 22:47Anthony Pompliano?

  Any books that you remember being like, wow, I learned a ton from that one?

• 22:50Speaker 02

  Yeah, so Stephen King on writing is a great book. And then Catcher in the Rye, I just wrote that out. And then a ton of sales pages. So like sale, like sales letters from the 50s, 60s and 70s when they used to mail people stuff to get them to buy like an encyclopedia. I found all the bestselling ones and I copied them all up by hand.

• 23:07Anthony Pompliano?

  Oh, interesting. Okay. And so really it was just a repetition of actually handwriting. And I think.

• 23:11Speaker 02

  I have a notebook stacked here.

• 23:13Anthony Pompliano?

  If I remember the science correctly, uh, there's a lot of studies that show if you sit and you write something down, you actually remember it much higher than if you type it or anything.

• 23:21Speaker 02

  It's called copy work. It's a learning technique that we actually used to use in public schools. But for some reason we went away with it because it's really boring and not fun, but it's very effective. Benjamin Franklin used to write about this. He was like, yeah, here's how you learn.

• 23:33Anthony Pompliano?

  Really?

• 23:34Speaker 02

  Um, it's really effective.

• 23:35Anthony Pompliano?

  Okay.

• 23:35Speaker 02

  It's not like I'm smart. I stole that.

• 23:39Anthony Pompliano?

  So you're doing this, you begin learning the copyrighting skill. Where do you go from there?

• 23:44Speaker 02

  Yeah, so I knew how to like write content. I mean, I think that I was born with that talent and I harnessed the skill. I learned the skill.

• 23:51Anthony Pompliano?

  And you enjoyed it probably?

• 23:53Speaker 02

  A little bit. I enjoyed the result unfortunately more than the journey.

• 23:56Anthony Pompliano?

  Okay.

• 23:56Speaker 02

  But I was willing to do it and it was, it was kind of fun. It was like a love hate thing.

• 24:01Anthony Pompliano?

  Okay.

• 24:01Speaker 02

  Um, and so, I mean, it was always fun being good at something and I was pretty good at it. So I learned how to get traffic to a website in doing that. I knew what emotions would get people to share things and I studied it like crazy. I just like would, I would look at upward, what's it called, Upworthy? Remember that clickbait?

• 24:16Anthony Pompliano?

  Oh, yeah. That thing was massive for a while.

• 24:18Speaker 02

  What are they doing? How do they do that? Okay, so I learned all these best practices.

• 24:20Anthony Pompliano?

  And so Upworthy, for those that don't know, was basically a site where they would find viral videos online. They would put it in their like very specific wrapper.

• 24:27Speaker 02

  Yeah, like you're not gonna believe number seven. Like the top 10 scariest photos from the 9/11 tragedy, number four will make you cry.

• 24:34Anthony Pompliano?

  Yep.

• 24:35Speaker 02

  So that's a famous tagline called, it's from a sales page that the Wall Street Journal did an ad. And then the ad said, they laughed at me when I told them. I could play the piano well, and then I sat down and started playing. And the point is like, the story of how, when he started playing, they all started loving him and that's why you should learn how to play piano. That's what it comes from, it comes from that famous headline. Um, and so, I learned copywriting, and so I started writing a ton of blog posts. And the first month or two, we got almost a million people to the website.

• 25:05Anthony Pompliano?

  Okay, these aren't normal blog posts.

• 25:06Speaker 02

  Yeah.

• 25:06Anthony Pompliano?

  Right, it's not like, hey, here's how you send a cold email.

• 25:08Speaker 02

  No, although I did do something like that, but the most, the first blog post we ever wrote was, I knew a guy who was making 50 or 60 grand a month, gaming the Kindle system, and what he would do is he would plagiarize bestselling books on how to sleep with women, and then, he would either just put a sexier cover and then buy reviews, or he would send it to the Philippines, they would rewrite it, and then he would put it back up, and he was making a lot of money, and I was like, that's pretty scammy.

• 25:31Anthony Pompliano?

  But basically what he was doing was, he one, discovered a system, he learned how to hack it.

• 25:36Speaker 02

  And he exploited it.

• 25:37Anthony Pompliano?

  And then he basically, but not himself usually, he actually had a whole team that he was using to authorize, so he didn't even have to do any work.

• 25:43Speaker 02

  Yeah, and I was like, that's really, I don't like that, but it's like, I love it and I don't like it, you know what I mean? I'm like, this is like a juicy story.

• 25:49Anthony Pompliano?

  Yeah, it's one of these things where it's almost like, I love the initiative, I love the mentality, I hate the execution.

• 25:55Speaker 02

  Yep, yeah, yeah, yeah.

• 25:56Anthony Pompliano?

  Could you take that same skillset and apply it to something else, you'd be so much better off in life.

• 26:00Speaker 02

  Exactly, and so, we wrote about that the first week, and the second week, we, um, me and my co-founder John.

• 26:05Anthony Pompliano?

  Did he know you wrote it, by the way?

• 26:06Speaker 02

  Yeah, um, we hit him.

• 26:08Anthony Pompliano?

  Was he happy?

• 26:08Speaker 02

  We, he, no one could track it to him.

• 26:10Anthony Pompliano?

  Oh, okay, got it.

• 26:11Speaker 02

  We used fake names, and then the next week, we, um, Romance Novels has the most liquidity in the marketplace, and so, more people buy it. And so, it was weird, it was like, the top categories were like, women who wanted to have sex with werewolves, women who wanted to have sex with black guys, and women who wanted to have sex with, um, military men. And so, we just like plagiarized some book and put a cover that kind of combined like werewolf, black werewolves, army, sex.

• 26:37Anthony Pompliano?

  Okay, so basically, but you were using data to figure out what do people want?

• 26:41Speaker 02

  I mean, data and like, we just scanned it every day and like, what's going on here? And so, we wrote a book, uh, we became a bestseller book. We gave this a sum and we became a bestseller.

• 26:50Anthony Pompliano?

  Incredible.

• 26:51Speaker 02

  And then the joke was, we put in our LinkedIn best selling author.

• 26:53Anthony Pompliano?

  Yep.

• 26:54Speaker 02

  Of Captivating Claire, that was the name of the book.

• 26:56Anthony Pompliano?

  There's a lot of people who have done that.

• 26:57Speaker 02

  Yeah, and so I was like, that's scammy, but let's do it. And so, we got a ton of traffic from that.

• 27:01Anthony Pompliano?

  Cause you wrote like a how to, how did we do this?

• 27:03Speaker 02

  Yep.

• 27:04Anthony Pompliano?

  Right, and I'm sure a bunch of people are like, oh shit, like, that's very cool.

• 27:06Speaker 02

  Yeah, we got a lot of hate for it, but the people who we wanted to love it, loved it. And that's how we got our first 5,000 or 10,000 subscribers in a week.

• 27:11Anthony Pompliano?

  Okay, and so, when you're doing this, uh, it's one thing to write a blog post, you get a bunch of traffic. How do you actually, inside of that blog post, get them to sign up for the newsletter?

• 27:18Speaker 02

  So that's another copywriting thing. You have to understand, it's called, uh, you probably, you may or may not know this, AIDA, Attention, Interest, Desire, Action.

• 27:24Anthony Pompliano?

  Wait, say it again?

• 27:25Speaker 02

  AIDA, A-I-D-A, Attention, Interest, Desire, Action.

• 27:31Anthony Pompliano?

  Okay.

• 27:31Speaker 02

  Attention, grab their attention and, and, and do something that can be shocking, or anything grabs their attention. Get them interested by getting them to go down the slippery slope and tell them interesting facts about, uh, whatever it is. Make them desire it by telling them benefits and features of this product. And then, get them to act by specifically and clearly explaining what to do.

• 27:51Anthony Pompliano?

  Got it, okay.

• 27:52Speaker 02

  And so, I would have pop-ups that followed that formula, or the whole website would follow that formula. Where it would be like a pop-up that said, "Oh shit!", that got your attention. And then, the interest was, okay, look, you get a ton of pop-ups in your life, but this one will be, will be meaningful. Or like, if you, and if you don't like it, email me and I'll Venmo you a dollar. Okay, so you're interested now, like, you're like curious, so desire. This website, I don't even remember, so I'm making this up. This website is actually, like, you should enter your email for these reasons. Just enter your email right here and check your email box in one minute, and you're gonna get the best damn confirmation email you've ever read. Like, something like that.

• 28:27Anthony Pompliano?

  Yep, and then people, basically, it's almost like they can't resist seeing what the confirmation email is.

• 28:32Speaker 02

  Exactly, yeah.

• 28:33Anthony Pompliano?

  Super, super smart.

• 28:34Speaker 02

  So that's all, that's, and then the, and then the confirmation email was really, really clever. And if you actually Google the Hustle Welcome Email, loads of people write about it. So that's how, but, but, but then, when we were starting, we weren't even a daily email. Like, I was still trying to figure out what the business is and how.

• 28:48Anthony Pompliano?

  What were you doing?

• 28:49Speaker 02

  We were, I was just blogging a ton, and then, every week, two times a week, I would email out the new blog posts.

• 28:55Anthony Pompliano?

  Pretty smart, okay.

• 28:56Speaker 02

  Yeah, and then I was like, wait a minute. Let's just only make it an email because the math works out to where 50% of people are opening up their emails and only 10% of those people click through. Like, let's just give them all the information.

• 29:09Anthony Pompliano?

  In the email.

• 29:09Speaker 02

  Yeah, like, who cares? Like, your phone's a phone. Like, the phone is the same size, no matter what. Who cares if they're on Safari or in the mail app?

• 29:17Anthony Pompliano?

  Yep.

• 29:17Speaker 02

  Like, if I have their attention, let's...

• 29:18Anthony Pompliano?

  So, here's my question, is when you make that switch, there's a lot of people who say, "I don't want to move all of my content to the email because now, all of a sudden, people can't discover it on the web." Were you still posting it on the web as well as in the email?

• 29:29Speaker 02

  Yeah, but not a lot of people would use it, and so that just made... And then they had to subscribe.

• 29:32Anthony Pompliano?

  Yep.

• 29:33Speaker 02

  To get it.

• 29:33Anthony Pompliano?

  And it basically just forced people into that. And now, and what it also does, I guess, is it takes you from a pull-to-a-push type relationship with the user because now you're actually sending it to them when you want, rather than have to go to your website and pull the content to them.

• 29:46Speaker 02

  Yep, exactly.

• 29:47Anthony Pompliano?

  Got it. Okay, so you get to 5, 10, 20,000 subscribers, kind of early, you're blogging.

• 29:51Speaker 02

  The first year was some number between 100 and 200.

• 29:55Anthony Pompliano?

  That's pretty good.

• 29:56Speaker 02

  It was good.

• 29:56Anthony Pompliano?

  Yeah, and it's all through blogging?

• 29:58Speaker 02

  Yeah, I don't think we spent a dime.

• 30:00Anthony Pompliano?

  Okay.

• 30:00Speaker 02

  On marketing.

• 30:01Anthony Pompliano?

  At what point do you decide, one, to do paid marketing, and then, two, do you do any referral stuff at any point?

• 30:05Speaker 02

  Oh, when I launched HustleCon, I hacked together this referral program where people would refer someone, and if they bought a ticket, they would get 50 bucks.

• 30:13Anthony Pompliano?

  So, if I get you to buy a ticket to HustleCon...

• 30:16Speaker 02

  We did a bunch of different schemes.

• 30:17Anthony Pompliano?

  I get 50 dollars.

• 30:18Speaker 02

  There were some schemes, like, if you get 100 friends to enter their email, you get a free ticket. If you get someone to buy a ticket, you get 200 dollars.

• 30:24Anthony Pompliano?

  How did you track it?

• 30:26Speaker 02

  It was really ghetto. I mean, our conferences, the second... The first one I did had 350, the second one had 600, so it wasn't that hard to track it just in the spreadsheet.

• 30:34Anthony Pompliano?

  Yeah, that's not bad.

• 30:35Speaker 02

  It wasn't very hard to track.

• 30:37Anthony Pompliano?

  But it goes back to the idea that I think a lot of people, when they see some of this stuff, they're like, "Oh, my god, the Hustle is so smart. Like, they used all this technology, but whatever." And you're like, "No, we use the spreadsheet."

• 30:45Speaker 02

  I'm not technical, by the way. I'm super not technical.

• 30:46Anthony Pompliano?

  Yeah.

• 30:47Speaker 02

  No, it's those spreadsheets. Like, I built this thing, I paid my friend 500 dollars to build it, and he built it in such a way that I could just go on Heroku, click "Export," then "Sort," and "Match." Like, it was like this, like, really, like, hacked-together way. It wasn't sophisticated, or I don't... Kind of sophisticated, but not really.

• 31:06Anthony Pompliano?

  Okay, so you're doing that, you've got the referral program, and then at some point, you say, "Hey, let's do paid ads." What was the decision process there to start doing paid ads?

• 31:13Speaker 02

  Because I knew early on what an email could be worth. I knew early on that, like, I did the math, I'm like, "All right, if they stay for this long," which I think they will, and we charge just so much for advertising, and our fill rate is 90%, and email could be worth X. Can I go out and acquire an email for cheaper than that? And so I would spend a few dollars and I would get that and then I would spend more and more and more. And that's kind of how it worked.

• 31:34Anthony Pompliano?

  And at the same time that you're spending more and more on an aggregate kind of investment, were you also driving down the CAC of each email?

• 31:41Speaker 02

  Oh, yeah.

• 31:42Anthony Pompliano?

  Right? So you're getting much better at it as well. So your dollar becomes more efficient on the spend side? Got it.

• 31:46Speaker 02

  But once you start spending a lot of money, then it goes up.

• 31:48Anthony Pompliano?

  Of course. And this is all through like Facebook and Google? Or were you finding really niche platforms as well?

• 31:54Speaker 02

  At first I was, it was a one man show or two man show. It was me and John and Kara and like two or three other people. So I didn't have a lot of bandwidth.

• 32:03Anthony Pompliano?

  Yep.

• 32:03Speaker 02

  And I didn't know anything. Like I had to learn Facebook like

• 32:07Anthony Pompliano?

  Yep.

• 32:07Speaker 02

  On the fly. So, um, no, we sponsor mostly one or two channels.

• 32:13Anthony Pompliano?

  Got it.

• 32:14Speaker 02

  Twitter, just the big programmatic ones.

• 32:16Anthony Pompliano?

  Yep. And then as you're doing this.

• 32:18Speaker 02

  And now we spend all over the place, other emails. We've even tried billboards, everything.

• 32:24Anthony Pompliano?

  And as you're doing this, how are you measuring whether it's working or not? Like, I think one of the big things is like, it's very authentic for you to be like, oh, I didn't know what I was doing. Like, we were just kind of like throwing a bunch of stuff at the wall. And were you just looking at like, oh, there's more people signing up for the email list? So like, things are going well?

• 32:39Speaker 02

  Well, so I knew the math behind it. I always, because we are bootstrapped, I like, every dollar had to turn into more dollars. Every dollar spent had to turn into more dollars. And I knew the math behind it. I modeled out what the business could be. And I was like, I think this could, like, this business could work. I mean, it made sense. And then, so half that answer is, well, the math just works out that this will work. And then the other half is emotional. And like, some days it was like, no way, this can't work. And then other days it was like, I think it's working. So the math always showed that it could work. But, and then emotionally I was like, oh yeah, we got a lot of traffic. It's going to work. And then other days like, oh, it's not going to work. And around this time, Business Insider sold for $600 million. So I was like.

• 33:21Anthony Pompliano?

  Henry Blodgett, yeah.

• 33:22Speaker 02

  Yeah, I was like.

• 33:22Anthony Pompliano?

  Wild story about Henry that a lot of people don't know. He was barred from the financial.

• 33:25Speaker 02

  Yeah, I know all about him.

• 33:27Anthony Pompliano?

  Yeah.

• 33:27Speaker 02

  I can tell you all about him. And he started that company with Kevin Ryan. You know who that is?

• 33:30Anthony Pompliano?

  I do not. Who's that?

• 33:31Speaker 02

  Kevin, it was Kevin Ryan's idea. Kevin Ryan founded Gilt. He founded MongoDB, which is publicly traded. He founded AdWords, or he's the CEO of AdWords before it sold to Google. It was called DoubleClick and then changed to AdWords. He sold, you know, Zola. He started that.

• 33:46Anthony Pompliano?

  Wow.

• 33:47Speaker 02

  Yeah, so.

• 33:47Anthony Pompliano?

  He's been around.

• 33:48Speaker 02

  Yeah, so I, like I said, I did research. I know, like, I know all these guys because I would just cold email them like crazy.

• 33:54Anthony Pompliano?

  Well, the part that with Blot that was so interesting was, I think he was a financial analyst. He basically got barred.

• 33:59Speaker 02

  He was kind of a scapegoat a little bit.

• 34:01Anthony Pompliano?

  Yeah, and he got barred for basically what I think a lot of people were doing at the time was they would write publicly to like clients and say like, you know, hey, we have a buy rating on this stock. And then internal emails would show them be like, this is a dogshit stock, right? So it was kind of like, they were saying one thing publicly, one thing negatively, which according to the rules is wrong. But it was more of like a, everyone's doing it, it's wrong, it's not enforced. And then all of a sudden, like, we need two or three people to like clamp down on.

• 34:23Speaker 02

  Yeah, and look, he didn't trade again, but he still crushed it, so good for him.

• 34:26Anthony Pompliano?

  Well, so when he started, I think it was Silicon.

• 34:29Speaker 02

  Alley.

• 34:29Anthony Pompliano?

  Alley first, right? There was a big debate, like, is he allowed to do this? Because he's technically talking about stocks and finance and whatever.

• 34:36Speaker 02

  As long as he didn't own it.

• 34:37Anthony Pompliano?

  As long as he didn't own it, as long as he didn't manage money. And so it was a way for him to basically put that knowledge that he had to work, right? And obviously.

• 34:43Speaker 02

  And he's badass.

• 34:43Anthony Pompliano?

  600 million dollar company.

• 34:45Speaker 02

  He's great. He's real smart and very, he's a great writer. So those guys sold and I was like, something's here. I think I could, I just, usually when I start stuff, and now I like own a couple of other businesses or a part owner in some and invest in a little bit, like, I usually like, so I think of like, all right, step one, step two is this. Step 10 is like, maybe it'll be bigger than Business Insider. Maybe I could turn this into Fox and own like all these things. Maybe this could be.

• 35:12Speaker 02

  Gartner, or something huge. But, and to get close to that, I'm gonna do this email thing and then I'll just make money off of it. And then steps three, four, five and six, I'm like, I don't know what those steps are.

• 35:24Anthony Pompliano?

  But I figured it out.

• 35:25Speaker 02

  I'm super confident I'll figure it out. You know what I mean?

• 35:27Anthony Pompliano?

  Yeah, but I think it's the perfect balance between like, I kind of know like what my North Star is, like where I'm going, right? It's like, I want this to be really big, but if I try to jump to step five or six, then like I'm screwed because I'll never start one and two. But if I literally just start like, let's start walking, right? And let's do step one, step. Two, all of a sudden, like it becomes clear what step three is.

• 35:48Speaker 02

  Yeah.

• 35:49Anthony Pompliano?

  And then three becomes clear for four, five, six.

• 35:50Speaker 02

  That's what holds a lot of people back. So it's like, I'm gonna drive, like, there's a huge mountain 20 miles away. I'm gonna drive towards it and I know that I just have to, I can only make a left right here. So I'll make a left and then when I get there, I'll figure out, you know.

• 36:03Anthony Pompliano?

  Yeah, it's one of these things where a lot of times founders will come to me like, have this idea, but whatever. And one of the things I always say to them is, what is the one thing that you think that you could accomplish in the next three weeks? Right, or the next four weeks? And usually it's like dumb stuff, like, oh, I could get the website builder, I could do that, you know, like whatever it is. It's not something that's like actually material to what their end goal would be. But I'm like, if you can get that done, I bet that you're then personally interested enough to then go to the next step.

• 36:30Speaker 02

  Yeah, and I've done, I've started enough businesses that were successful on a small scale to know, to learn, like, you figure it out. You know, it's like when I travel now, I'll just like show up and I'm like, we'll get a hotel, we'll figure it out. I'm perfectly fine winging most everything.

• 36:44Anthony Pompliano?

  So, but this also brings, I think Silicon Valley is the best in the world at doing this, where it's kind of like this experimentation, iteration type mentality, where people will start things and there's not a lot of pressure on it either, right? Like it, for most businesses around the world, if you go and you talk to entrepreneurs who want to start these businesses, they literally now will be like, I want to build a $10 billion business and here's like my grand plan to get there. And whether it's a business, a plan, or some sort of deck, like they've got this very specific, this is what I'm gonna go do. I think more the Silicon Valley mindset is like, hey, I'm kind of like tinkering with this thing. It seems to kind of be working. Uh, I think we can make a little bit of money on it. And like, I think that it could be bigger, but like, we're gonna figure it out.

• 37:21Speaker 02

  Well, cool shit, a lot of cool shit starts small. Airbnb, when they had their pitch deck, they're like, we think this could become a $100 million company. That's what Jeff Bezos said. He goes, I think, I think if we're lucky, we might be able to become a $100 million company.

• 37:35Anthony Pompliano?

  Yeah.

• 37:35Speaker 02

  Like it's, and that's like.

• 37:37Anthony Pompliano?

  He'd just spend more than that on a house.

• 37:38Speaker 02

  Totally. And I listened to an interview with their first investor, Madonna, what's the fun, I forget.

• 37:44Anthony Pompliano?

  Madrona.

• 37:44Speaker 02

  Madrona. And that's what he said. He goes, Jeff said, you know, we might be able to sell $100 million worth of stuff.

• 37:51Anthony Pompliano?

  Crazy.

• 37:51Speaker 02

  So, and that's like a big number.

• 37:53Anthony Pompliano?

  Yeah.

• 37:53Speaker 02

  So, yeah, and I think both. Work like Peter Thiel, he's like, fuck, don't iterate, have this grand vision. And so both, both work, but what regardless, you have to be flexible and, and that's hard for a lot of people.

• 38:06Anthony Pompliano?

  And I think part of the, like the Peter Thiel, Keith Royboys, like those guys who, uh, what they believe is almost like, you, you know what you want to build and you bend the world to you, right? Versus other people who say, hey, I'm going to start doing this. And, uh, then I'll kind of figure it out as I go. I actually don't think those two things are that dissimilar, right? I think that they're actually very, very similar, uh, because one is more of like a vision type. I know what I want to build and then the iteration stuff I'll figure out along the way. Versus somebody's more focused on the iteration and they don't know yet what it'll become, but when you put those two together.

• 38:37Speaker 02

  It's similar, but you gotta be bold for both of them and you learn along the way for both of them. It's, uh, it is a little similar. I mean, like, because I didn't have a lot, I wanted to do this one so I could get like a hit. Now that I've had a hit, maybe my next one, I'll raise a ton of money or I'll bet a lot of my money and just be like, fuck it, let's bet it all.

• 38:53Anthony Pompliano?

  Yep.

• 38:53Speaker 02

  And that will be exciting, but regardless, I'll learn along the way and kind of deviate slightly.

• 38:59Anthony Pompliano?

  Did you think that starting the media side was really risky?

• 39:03Speaker 02

  No, not at all.

• 39:04Anthony Pompliano?

  Why not?

• 39:06Speaker 02

  Cause I felt like.

• 39:07Anthony Pompliano?

  Like most people would have said, I have something that works. I'm making some money on the conferences. Why would I ever start doing something else and spend money to do that?

• 39:14Speaker 02

  So I did it the other way around. I have this conference. I know it works. If the media side fails, I can always do that. It was the other way around. It was like, or I could always sell hot dogs or I actually saved $500. I was like, I'll fly home and live in my mom's house.

• 39:27Anthony Pompliano?

  So you are very similar to, uh, kind of the classic founder who looks at risk very differently than most people, right? Cause most people who have like a corporate job would look at that risk and say, there's no way I can take this risk. Instead you're like, look, if I take this risk and XYZ goes wrong, I have all these other options.

• 39:44Speaker 02

  Well, I, I look at, there's two different ways that I convince myself all the time to do it. Cause I have to, you know, you get scared sometimes. The first is if I fail and everyone sees it, they're going to want to hire me.

• 39:57Speaker 02

  And I'm starting a media company. By definition, I gotta get a lot of eyeballs. Everyone will know me and if I fail, I'm gonna get a job.

• 40:03Anthony Pompliano?

  Yep. Every corporation loves to hire the failed entrepreneur because they know that they're super ambitious, they're resourceful, etc.

• 40:09Speaker 02

  Yeah, I was like, I'll be able to get a job probably. And I've like, never really had like a normal job. I was like, that'd be, that'd be like putting a noose on my neck, but like, whatever. And the second thing was, I always wanna protect the downside. And so what I mean by that is, in my head, so I've like, slept outside before when I had some issues and I was like, so worst case scenario, I'll sleep outside. I was like, did I like that? I didn't love it, but I would do it. So what's like a step up from that? Well, would I be willing to like, tell my parents I totally failed and, and they would accept me? I guess. Okay, okay.

• 40:42Anthony Pompliano?

  I wouldn't love it, but I'd do it.

• 40:43Speaker 02

  Like, I'll, I'll accept that. I'm, that's a fine downside. Therefore, I found the lowest I could go. And so I set aside $500. And I was like, there, the downside's protected.

• 40:53Anthony Pompliano?

  This is the emergency fund to get home.

• 40:55Speaker 02

  Yeah, I was like, there's nothing to worry about. Like, I have just accepted that the worst case might, I've accepted already, the worst is going to happen. I've planned for it. I have no downside. That's how I look at it.

• 41:06Anthony Pompliano?

  So, you've now grown this to over a million subscribers?

• 41:09Speaker 02

  Yeah, so well over.

• 41:11Anthony Pompliano?

  Close in on 2 million soon?

• 41:12Speaker 02

  Yeah, and, yeah, it's up there. And we add, like, on a good day, like, tens of thousands of new people a day.

• 41:20Anthony Pompliano?

  That's awesome.

• 41:21Speaker 02

  And it's a good company. It's eight figures in revenue.

• 41:26Anthony Pompliano?

  All advertising until recently, when you added subscription?

• 41:29Speaker 02

  Yeah, so I do, the, the plan was the beginning, from the beginning was build up this massive audience and start selling stuff for them. And when I started my company, I did loads of research. Like, I just wanted to understand best practices and I would read biographies and I would reach out to experts and I would just interview them and ask everything I could, just so I could copy what worked and not copy what didn't work. And I could just save myself years of heartache. And so. I realized when we were getting ready to launch this new product, I did the same process. And I started showing advisors and investors like the reports I was putting together and they're like, "Oh, just sell that." And so I read the book of by Gartner, the guy who started Gartner, Gideon Gartner. You know who Gartner is?

• 42:09Anthony Pompliano?

  I know the company, I don't know the person.

• 42:11Speaker 02

  Okay, Gartner, it's a big $10 billion a year research thing. And they're like, "That's a big thing, just do that." And I was like, "Oh yeah, you're right." And I love doing this research. And so we launched Trends, so trends.co.

• 42:22Anthony Pompliano?

  Go sign up at trends.co.

• 42:24Speaker 02

  And then if you enter in the code POMP, you'll get a 50% discount.

• 42:29Anthony Pompliano?

  Oh, look at that, POMP's got your back, always.

• 42:32Speaker 02

  Can you remind me to make that code? Remind me to make that code.

• 42:36Anthony Pompliano?

  It's already made now, by the time you're listening.

• 42:39Speaker 02

  Where was it?

• 42:40Anthony Pompliano?

  So you launched Trends?

• 42:41Speaker 02

  Yeah, so we launched that a little while ago. And that's already a seven-figure subscription business. And so with this business, I think what we can do is then create a higher-end one for specific to certain industries. And I think that we can build a $100 million a year business that's very profitable with 30% advertising, 30% $300 to $400 a year subscription business, and then a $30 or $50 million a year high-end subscription business.

• 43:05Anthony Pompliano?

  So right now, how much are you charging for Trends?

• 43:07Speaker 02

  It's cheap, it's $300 a year. And what you get is, we have a team of analysts. And with Trends, all we do is uncover different opportunities in the entrepreneurial world. And so we do two things. The first thing is we do case studies in cool and interesting companies or interesting companies or industries. So for example, I went to Vegas and stayed at the MGM Grand. And I was like, "How the fuck is this hotel so big? This is crazy." And so we went and did a report on the top 10 biggest publicly traded hotel businesses and explained like, okay, so like the secret sauce is basically, not the secret sauce, but the metrics that matter most is occupancy rate and average revenue per room. And if you nail those, it'll work.

• 43:46Anthony Pompliano?

  It's game over.

• 43:47Speaker 02

  And then we went further and said, "Here are the top growing sectors that all the experts, as well as our data, has shown." And so it's like different lifestyle hotels, things like that. And then the second thing we do is we've created a technology that crawls the web and finds really fast-growing things. So for example, we got an alert that sleep. So people are searching for products that make you sleep better, far more than meditation things. Meditation's a huge business. And so we flagged that and we told our readers about it. And then we wrote where are the opportunities within the sleep sector and who is capitalizing on it? Who has interesting opportunities and interesting businesses and what do we think will win? And then we have a private community of thousands of people where you can discuss those. And so I fly around the country and I meet with, do meetups for those groups and all types of things like that.

• 44:31Anthony Pompliano?

  And so who is on the receiving end of this? Like who's the ideal trend subscriber? Is this somebody who's an entrepreneur, an investor, both?

• 44:39Speaker 02

  It's really wide. So it's guys like you and me who are just schemers. Like I have my business, but I'm always like tinkering like.

• 44:46Anthony Pompliano?

  People come in here and they pitch me wild ideas and I literally, the more wild and like schemey that it is, right? Meaning like I'm going to hack this together and this together and this together. And then like I'm going to have this like business and like, oh yeah, I have no employees and blah, blah, whatever. And I'm like, all right, let's go try to figure that out. Like that's actually way more fun than the like, I'm going to go raise $20 million and I'm going to go build this hardware startup.

• 45:06Speaker 02

  Yeah, well, I use scheming positively, which is I'm always like, like if you go to a restaurant, if you're the type of person that goes to a restaurant and be like, man, if they move that counter over here. So then the barista didn't have to turn her back all the way and only turned her back a little bit and then put that thing here. That would actually, they could probably serve 100 more customers.

• 45:22Anthony Pompliano?

  Yes, it's actually resourcefulness is like what the real word is, but scheming is a way more memorable word to use.

• 45:27Speaker 02

  I use schemers. I always say ABS, always be scheming. And so the subscribers are like people like you and me who are investing in new things or who, I have my own business and so I'm not going to start another business now, but I'll apply like what I, what did the hotel industry do that's cool? Is they franchise their stuff? Maybe I should franchise my conferences, kind of like the hotel industry, you know what I mean?

• 45:48Anthony Pompliano?

  Yep, yep, yep, yep.

• 45:49Speaker 02

  So a lot of freelancers, a lot of people who own small businesses, a lot of executives at big companies, people who are just thinking all the time about optimizing the business.

• 45:57Anthony Pompliano?

  People ask me all the time, like what content I consume, right? And one of the things I tell them is like, my favorite thing to do is read profiles or biographies on people and businesses. And the reason is because. You don't have them like writing like, here's the lesson plan for today.

• 46:11Speaker 02

  You just see what they do.

• 46:12Anthony Pompliano?

  But I could literally, you could rattle off Ted Turner, Sam Walton, Ken Langone. Like you just go down the line of all of these people.

• 46:19Speaker 02

  I've read all of those.

• 46:20Anthony Pompliano?

  Yeah.

• 46:20Speaker 02

  And you learn.

• 46:21Anthony Pompliano?

  You learn so much, right?

• 46:23Speaker 02

  That's why I love your wife's work.

• 46:24Anthony Pompliano?

  Yeah, she, she, uh, she one day says to me, she goes, um, uh, so she's got the profile, right? And, uh, she's curating all of these and, uh, she's like, I really enjoy this work. And I was like, why? And she never used the word learned, but that's basically what she was saying. And what was so fascinating to me was she had never thought about starting a business before. She never thought about any of this stuff. And she's like, I feel like I just understand more about how people build things by reading their stories. More so than I would get out of reading like a, here's how to start a business book or like, you know, here's how to be a CEO.

• 46:55Speaker 02

  And so that's what trends is, is we just look at case studies.

• 47:00Anthony Pompliano?

  Yep.

• 47:00Speaker 02

  And take, and we make recommendations, but take from it what you will.

• 47:04Anthony Pompliano?

  Got it. All right. I want to talk about like new media models and I'm going to throw a couple of, uh, companies out there that I think you've looked at or have opinions about and we can kind of talk through them. So, uh, the first is Substack, which is obviously in the email, uh, world that you're in. Um, and so this business.

• 47:18Speaker 02

  Are you an investor?

• 47:19Anthony Pompliano?

  Uh, no, I'm an advisor. Um, but the, the business that they are building is, uh, essentially empowering a whole new generation of people to build a business that previously they couldn't. Right? So it removes all the technical, uh, friction to starting these email subscription businesses. Now, you probably had to build out a lot of this stuff initially. And now if you were starting again, you could start on a Substack to some degree.

• 47:45Speaker 02

  Yeah, I, uh, sorry, my shoes cutting off my blood circulation here. Um.

• 47:50Anthony Pompliano?

  We might have an amputee in the building.

• 47:52Speaker 02

  Yeah. Oh, can they see my feet on camera?

• 47:55Anthony Pompliano?

  Nah, you're good.

• 47:56Speaker 02

  Good. I'm going to go shoeless. Um.

• 47:59Anthony Pompliano?

  Shoeless Sam has arrived.

• 48:01Speaker 02

  I got a hole in my boot.

• 48:03Anthony Pompliano?

  Alright, Substack.

• 48:04Speaker 02

  Yeah, um, okay, so...

• 48:07Anthony Pompliano?

  By the way, the grabbing of the attention, we just got everyone's attention when he went shoeless. Go ahead.

• 48:11Speaker 02

  Uh, Substack, um, okay, so I went to their office and met with the founders. They're like the type, I say this in a good way because I'm part of this, they're like nerds.

• 48:21Anthony Pompliano?

  Yep.

• 48:22Speaker 02

  And those types of people will win.

• 48:24Anthony Pompliano?

  A lot of people don't know, Chris Bess, who's one of the founders and the CEO, previously was the founder of Kik, which is a billion dollar company.

• 48:31Speaker 02

  I do know that. So I would bet on them to win. The current iteration will not win, my prediction is.

• 48:36Anthony Pompliano?

  Why?

• 48:37Speaker 02

  I think this because I don't think there are that many people who will have paid newsletters.

• 48:41Anthony Pompliano?

  Okay.

• 48:42Speaker 02

  And there definitely won't be a lot of people who have it at $5 a month.

• 48:46Anthony Pompliano?

  Okay.

• 48:47Speaker 02

  Um, what I, where I think they could win is by having that as well as an enterprise version. Which I talked to them the other day, I go, guys, I'll give you $10,000 a month, make this.

• 48:56Anthony Pompliano?

  And the enterprise version would include what that they currently don't have?

• 49:00Speaker 02

  So, right now...

• 49:00Anthony Pompliano?

  And the reason why I want to tease this out is this is the exact type of conversation that I think a lot of people aren't privy to. Like this happens behind closed doors, but you're somebody who says...

• 49:08Speaker 02

  I'll tell you what I told them, I'll tell everyone what I told them, I tweet about this all the time. The, okay, so the whole media world, a lot of people are trying to do paywalls. The way most people do it is fucking horrible. They don't know what, they're doing it in such a bad way. And the software that exists for paywall, there's very few, and the ones that do exist are horrible. They are so bad.

• 49:28Anthony Pompliano?

  It's so bad that a lot of people try to build it in-house.

• 49:30Speaker 02

  Yes. New York Times builds in-house. And like meanwhile, every free blogger uses WordPress, a lot of newsletters use Mailchimp. Why is there not a good thing that combines all, like does like a good, uh, paywall software? And it's awful, you, someone could, like, I'm not convinced it would be massive, massive. I mean, it's all relative, but I do think it could be a billion dollar company if it hits 100 million. Like, I think it could hit 100 million in revenue, and if you're an enterprise SaaS and do that, you're considered a unicorn. So if they iterate to build that, I think it could be a lot bigger.

• 50:03Anthony Pompliano?

  Okay, and it's all about the enterprise you think unlocks a whole bunch of revenue that they, that they otherwise couldn't get?

• 50:09Speaker 02

  Yeah, or... Or maybe they could do it the way they're doing it, but they have to change it a little bit. Like they have to have proper sales pages. They like, I want them to be the Shopify of paywall of Shopify of content.

• 50:22Anthony Pompliano?

  So the one thing, and I've told them this a bunch of times, uh, that I knew very early on, like, whoa, these guys are on the right track, right? At least in kind of heading in the right direction. Uh, I kept pinging them early on and being like, hey, can you guys could do this? Can you guys do this? And they'd always come back with like a, yeah, we'll put it down on the list, but, uh, not right now.

• 50:38Speaker 02

  So they focused.

• 50:39Anthony Pompliano?

  And it was just super, super focused. And it was like stupid stuff that I wanted like, hey, can you add so that somebody could put their first name in? So when I email them, I can use their first name rather than like email.

• 50:48Speaker 02

  Much higher engagement rate.

• 50:49Anthony Pompliano?

  Well, they were like, no.

• 50:51Speaker 02

  Good.

• 50:52Anthony Pompliano?

  Right? Cause they were just like, look, this is what we wanted to build, right? And like, we don't care about all the other kind of things that are nice to have, not need to have.

• 50:58Speaker 02

  Well, and I think that they're going to win, even though I think that their product right now is, I think their product, I think it's an amazing early version.

• 51:04Anthony Pompliano?

  Yes, I agree with that.

• 51:05Speaker 02

  And I think that, um,

• 51:06Anthony Pompliano?

  I think they would agree with that.

• 51:07Speaker 02

  Yeah. And I'm, but I would bet on that because you have to look at what something can be. I mean, they're so, it was like two years old, a year old.

• 51:15Anthony Pompliano?

  I don't even think, yeah, maybe.

• 51:16Speaker 02

  And they only have four, four or eight employees.

• 51:18Anthony Pompliano?

  Yeah, they just hired a couple more. They have, go to substack.com. They have tons of roles that they're hiring for.

• 51:23Speaker 02

  I went to their office the other day. It was completely empty. And I was like, what's going on guys? And they go, well, we're just getting ready to hire, but we're making sure we get the right people. I love that. So those founders, I think will win. If they iterate, I think they're for sure going to win. I would totally bet on them.

• 51:36Anthony Pompliano?

  I love it. Um, The Athletic, for those that don't know, is a subscription, uh, sports content site, think kind of like ESPN, but you pay 10 bucks a month, 60 bucks a year. They went around the country. They found, uh, the best local sports writers at all these local papers and said, hey, we'll bump your salary. Why don't you come write for our site rather than your local paper? They got a bunch of people to do this, like 300 plus of them. Uh, and they've built a really, really big business, uh, pretty quickly.

• 52:00Speaker 02

  I think it could be great. Um,

• 52:02Anthony Pompliano?

  What do you not like?

• 52:02Speaker 02

  I don't like their cap table. Uh, if I was the founder, which I've talked to a bunch of times, he was like always having a fundraise. They've raised maybe a hundred million dollars.

• 52:12Anthony Pompliano?

  Oh, really?

• 52:13Speaker 02

  I think, um,

• 52:14Anthony Pompliano?

  Yeah, I know nothing about the cap table.

• 52:16Speaker 02

  You can look it up. Uh, many, many tens of millions. It's, it's,

• 52:19Anthony Pompliano?

  I mean, they just took $30 million from Bedrock. So,

• 52:21Speaker 02

  It's probably in the hundred million range, 70 million. Um, I bet you the founders own less than 10% each. If they don't care about that, great. I wouldn't want to be in that position, but, um, the business. If they say, if what they say publicly is true, it's a $60 million a year company. So that's pretty valuable and it's recurring revenue.

• 52:41Anthony Pompliano?

  Yeah, yeah, yeah.

• 52:41Speaker 02

  Yeah, I think they said they have a million subscribers.

• 52:44Anthony Pompliano?

  60 bucks a year, yeah?

• 52:45Speaker 02

  Yeah, so it's really interesting. Bullish, I don't know if it's, I'm bullish yet at a $500 million valuation, but I would fall on the more optimistic side. Had you asked me a year ago, or no, two years ago, I'd have been like, that's crazy, that's ridiculous.

• 52:59Anthony Pompliano?

  Why? Why'd you change your mind? Just because they executed?

• 53:01Speaker 02

  I thought subscription revenue was a horrible idea and most people could never pull it off. And now I think it's the future.

• 53:06Anthony Pompliano?

  Whoa, okay, so unpack that a little bit more. Why did you change so radically?

• 53:10Speaker 02

  Because I saw the results that we have. I saw that consumers, this whole fake news thing that Donald Trump started. I don't care what you think about him, he's right.

• 53:18Anthony Pompliano?

  Like, oh yeah, oh, we can go way down that rabbit hole. The reason why half the country hates that he says it is because they know it's right.

• 53:25Speaker 02

  He's right.

• 53:25Anthony Pompliano?

  And the reason why the other half of the country likes that he says it is because they know he's right.

• 53:29Speaker 02

  He's right. I have owned clickbait websites. I was able to get millions of uniques to different.

• 53:37Anthony Pompliano?

  Of course.

• 53:38Speaker 02

  It's very easy.

• 53:39Anthony Pompliano?

  It's not an online thing, it's not a one publication thing. It's literally if you go to the grocery store and you pick up one of those like Inquirer bullshit things, they literally take a photo, they put some fake headline on it.

• 53:49Speaker 02

  That's a $200 million a year business, I believe.

• 53:50Anthony Pompliano?

  Of course. So this stuff's been around for a very, very long period of time.

• 53:53Speaker 02

  Yeah, it's called yellow journalism. I mean, Hearst built his whole empire on that. Robert, Rupert Murdoch was accused of doing that. This works. And it's not bad always. Sometimes it's funny, like TMZ, I think is the best.

• 54:04Anthony Pompliano?

  You want to hear what I think is crazy about TMZ? Everyone gives them a bunch of shit.

• 54:08Speaker 02

  They're always right.

• 54:08Anthony Pompliano?

  They were the very first person to report the Kobe Bryant helicopter crash.

• 54:11Speaker 02

  I was on TMZ.com right when it happened. They're always right.

• 54:14Anthony Pompliano?

  Yeah. And so I think what it gets to though is this idea that now with the internet, like people always thought this stuff was kind of like salacious or exaggerated or whatever, or all the way to just actually fake. Now they actually have the ability to verify that it's fake.

• 54:28Speaker 02

  Yeah, it's, yeah. And so I think that the reason why I, subscription I'm bullish on, we're doing like B2B subscriptions, so I think that's why we're going to kill it. But consumers and people, consumers and businesses are willing to pay for quality information.

• 54:42Anthony Pompliano?

  Do you think that there's, the subscription model changes the content?

• 54:48Anthony Pompliano?

  Like the type of content you create if it's behind the paywall versus not?

• 54:50Speaker 02

  Yeah, and I'll explain why. So, some businesses, like, I know how to run a media business now, and I know how they operate. What I would do if I started my business in 2000-

• 55:01Anthony Pompliano?

  20.

• 55:01Speaker 02

  No, let's say 2009, when Facebook started. 2010, whenever pages came out. What I would do is I would say, "Each writer, you guys have a 1 million page view quota. You have to hit it every month." And then I would go out and hire a thousand writers, and I would teach them how to write headlines, and I would be able to get that and make a lot of money.

• 55:20Anthony Pompliano?

  That's basically what BuzzFeed, I mean, literally built their entire business.

• 55:23Speaker 02

  And it was a great business when it lasted.

• 55:23Anthony Pompliano?

  Yep.

• 55:24Speaker 02

  It's still a good business, to be honest, but it's just that it's maybe not a multi-billion dollar company.

• 55:28Anthony Pompliano?

  I mean, Business Insider for the longest time took other people's articles, rewrote a couple of words, put a headline on it that was better, and then shot it out to the world.

• 55:34Speaker 02

  And it worked.

• 55:34Anthony Pompliano?

  Yep.

• 55:35Speaker 02

  And-

• 55:36Anthony Pompliano?

  Want to read the full story? Click here.

• 55:37Speaker 02

  Yeah, and you know what? I love Business Insider. It was pretty, it was wonderful. Or I think it is.

• 55:42Anthony Pompliano?

  It served the purpose that it set out to serve, and I think people appreciate when something fulfills the brand promise that it has.

• 55:49Speaker 02

  Yeah, and I really dug it. And so, that is one type of content. I would say, "Write, get this many pages." The best way to get it is to average 10,000 pages per article, write three articles a day. And boom, that's it. Now, with subscription, what you can do is you can say, you can write any amount of articles you want. You can write one a year, or you can write one a day. I'm gonna see which of your articles brings in the most new subscribers. And the way that you're gonna bring in new subscribers is someone's gonna read your article, and so they're gonna see it's paywalled, and they're gonna say, or they're gonna have friends, and they're gonna say, "This is, looks really interesting. I'm gonna pull out my wallet and give you $300 and buy it." And that is the test of quality, is if it's so good, they'll buy it, and I can measure all my writers that way.

• 56:34Anthony Pompliano?

  How, how much of that content do you think has to be behind the paywall versus giving it away for free and then getting people to subscribe? Like, what do you think about that balance?

• 56:42Speaker 02

  My current opinion, and it will change, maybe, is 100% should be paywalled.

• 56:47Anthony Pompliano?

  100%. How do people find it slash know that it's high quality?

• 56:51Speaker 02

  So what I mean by 100% is maybe like, what I mean is 100% of the articles, not 100% of the article. So for example, the headline, the picture, and maybe a description can be visible.

• 57:03Anthony Pompliano?

  Got it. So it's kind of like you're teasing them with a little bit of what is this article about? But if you actually want to read the article, you gotta actually convert.

• 57:11Speaker 02

  And then I think the, the concept of the publication, the concept of the content, the concept of the, all the other programming, the concept of what the value you're going to provide them, that needs to be done in the sales copy.

• 57:22Anthony Pompliano?

  And so what do you think about the model that some of the mainstream press has taken in terms of like, hey, I'll give you 10 articles, you can read 10 for free, and then you have to convert versus just hard paywall everyone?

• 57:31Speaker 02

  I don't know the results, so I can't actually, the data wins, but I don't think that that's a good idea.

• 57:37Anthony Pompliano?

  The only reason why I think they think it's a good idea is to keep doing it.

• 57:41Speaker 02

  Yeah, but they also do a lot of dumb stuff.

• 57:42Anthony Pompliano?

  That's true.

• 57:43Speaker 02

  You know what I mean? Like.

• 57:46Anthony Pompliano?

  But even like the New York Times, who I think at this point is very sophisticated.

• 57:48Speaker 02

  But the New York Times is different. The New York Times is different because they're not an upstart. They're not like, you know what I mean? Like what, if I was the New York Times, they're doing a lot of really good ad campaigns. I would say, I would do an ad campaign that says like, or maybe if I was the Wall Street Journal, I'd be like, like, I would turn your campaign like 16, get your license, like 18, go to college. 21, get, have your first drink. 25, get your first job, subscribe to Wall Street Journal. Like, you know what I mean? Like I would do ad campaigns like that where it's like, oh yeah, of course you have to subscribe. When you're a company like me and no one knows who you are yet.

• 58:22Anthony Pompliano?

  Whole different game.

• 58:23Speaker 02

  Yeah.

• 58:24Anthony Pompliano?

  Got it. You guys should start a podcast.

• 58:26Speaker 02

  Yeah, it's called My First Million. It's awesome. It's cool.

• 58:30Anthony Pompliano?

  That's the best pitch for a product we've had on the podcast ever.

• 58:33Speaker 02

  It's so fun though.

• 58:34Anthony Pompliano?

  It's awesome.

• 58:35Speaker 02

  It's so fun. So the way it started was Sean, a friend of mine who sold his company, started it where he would just interview people about the early days. And that was going fine, but then one day a guest didn't show up and Sean was like, hey, come in. Just riff with me, like we're doing now. And I was like, alright, let's riff. And I got a bunch of trends reports and then I did my own research. I like did research on the executive recruiting industry. I did research on cruise ships. I did research on Boy Scouts. I was like, these three business models are really interesting to me. And let me explain to you why. And we started riffing on them about like, I was like, what could work is, look, this Boy Scouts is declining. The reason it's declining is this thing. I think there's opportunity here and that's all we do in the podcast and people love it.

• 59:14Anthony Pompliano?

  Boy Scouts just went bankrupt.

• 59:16Speaker 02

  Yeah, and I think a big business can be built there.

• 59:19Anthony Pompliano?

  Oh, for sure.

• 59:20Speaker 02

  Like young, young, turning boys into men. I think it's actually going to become more popular because with digital, everyone's like, you gotta get out. You gotta do this. And then I wouldn't have the religion concept of Boy Scouts because religion is less popular. And I'm like, yeah, look at the numbers. And I like break out the financials. I'm like, here's this, this, and that's what we do on trends. I just do it in the podcast.

• 59:37Anthony Pompliano?

  Got it. And so as you've grown this, both on the email side and on the podcast, talk to me about ad sales. Like, how did you guys initially attack that? And then how have you gotten smarter about that over time?

• 59:47Speaker 02

  So we've had, our events were kind of retooling how we're doing them, but they were quite big. Like maybe we'd get 10 or 15,000 attendees a year.

• 59:57Anthony Pompliano?

  People would pay to come or was free?

• 59:58Speaker 02

  Pay.

• 59:59Anthony Pompliano?

  Pay, okay.

• 1:00:00Speaker 02

  And so I had hundreds of speakers, the founders of massive companies. WeWork, which doesn't hold as much clout as it used to, but WeWork, Casper.

• 1:00:09Anthony Pompliano?

  Did Adam come?

• 1:00:10Speaker 02

  Miguel.

• 1:00:11Anthony Pompliano?

  Or Miguel, okay.

• 1:00:12Speaker 02

  So all these like big.

• 1:00:12Anthony Pompliano?

  Miguel's still there, he's cool.

• 1:00:13Speaker 02

  Yes.

• 1:00:14Anthony Pompliano?

  Go read, go read Plena's profile on Miguel. She wrote a pretty good, pretty fair, I think, profile.

• 1:00:19Speaker 02

  He's just a hippie.

• 1:00:20Anthony Pompliano?

  Yeah, he's cool dude. He's like, what, 6'8", 6'7", something like that?

• 1:00:23Speaker 02

  He's massive, yeah.

• 1:00:23Anthony Pompliano?

  And so when I first met Plena, she, I think either right before I met her or right after, she wrote a article on, there's four friends from high school that all play basketball together, that all were running either as the founder or a lead executive of a billion dollar startup. Miguel, AppDynamics was another one. And then there was two other guys, I forget who the other two guys were. But there are four guys who all played on the same high school basketball team. And I remember reading the article and being like, what the hell are they putting in the water over there?

• 1:00:53Speaker 02

  They're all, well, he's a hippie. He lived in the commune. But we had.

• 1:00:58Anthony Pompliano?

  So you had a bunch of executives coming?

• 1:00:59Speaker 02

  Yeah, yeah, yeah, yeah. And so when we first started, so the conference, the first year made like three or four or $500,000. And our burn rate each month for like five employees in an office was something like $25,000 a month or something like that. And.

• 1:01:14Speaker 02

  I said, all right, let's build this email and then the email is going to become bigger than the conference. So I said, we got to get to 30 grand a month in ad sales to be profitable. So I called up or emailed all the founders who spoke at the conference and I go, guys, you know, I know how to execute. You know that like this is a real community. Put me in touch with your ad salespeople. And originally it was like deals like just give me your link and I'll put it in there and give me $500 for every mattress I sell. And then I hired Adam, who's now the president of my company and runs a lot of the day-to-day operations. I went to high school with him and he built the sales team from scratch. That's just a bunch of killers.

• 1:01:44Anthony Pompliano?

  And so when you guys think about how to create the products that you sell, like the actual ad product itself, is it still this like more D to C, hey, here's a link, go convert? Or do you do

• 1:01:54Speaker 02

  Both.

• 1:01:55Anthony Pompliano?

  brand and

• 1:01:56Speaker 02

  Both.

• 1:01:56Anthony Pompliano?

  actual response?

• 1:01:57Speaker 02

  Yeah, I mean, the ad that we've made tens of millions of dollars on, I just wrote it out one day and I was like, all right, there's the ad, you need to go sell it. And it worked. Now it's more sophisticated, like our technology for sending. So we have this thing called our CMS. That's not an appropriate name, but we still call it that. But our writers writing it, our ad salesman sees all the inventory. We know how many subscribers we have that day and we have a projected six-month plan based off of our previous six months. And then we, we can see the profiles of all the subscribers, like the demographics. Then we send a link to our advertisers. We've worked with thousands of advertisers advertisers at this point. So sales, like we close, let's say, Smartwater. We close Smartwater. That

• 1:02:40Speaker 02

  goes into our Salesforce. Our Salesforce tells our CMS. The CMS automatically sends them a link. They fill a brief that sends back to us. We create the ad. They approve. It goes out to people. Then check this out. The advertiser pays through that thing and a bank who we have a line of credit with sees like our accounts receivable and can loan us money against that. And so that's how we bootstrap the whole company.

• 1:03:03Anthony Pompliano?

  It's pretty good.

• 1:03:03Speaker 02

  It's pretty cool. It's really cool.

• 1:03:05Anthony Pompliano?

  And it's crazy that one of the things that you said in there that I think a lot of companies wouldn't do, because again, it's taking risk, is you said, hey, give me the link and you just pay me on what I sell. Like betting on yourself, right? Because I think a lot of people, especially when it comes to newsletters and content, etc., they're so used to the display model of just, hey, pay me two grand and I'll put your

• 1:03:24Speaker 02

  Well, some people like who sell like certain things, like Goldman has advertised with us, like they can't They don't, that's not how they work.

• 1:03:31Anthony Pompliano?

  Yeah, how do they measure?

• 1:03:33Speaker 02

  How many people opened the email?

• 1:03:34Anthony Pompliano?

  Did you call Goldman or did they call you?

• 1:03:36Speaker 02

  I didn't close that deal. I don't, I don't do deals anymore, but uh, I don't know, but I'll tell you something funny. Uh, I could talk about, I probably will get yelled at. I don't give a fuck. Uh, we had Goldman, but we said, we wrote a story about fuck Jerry.

• 1:03:49Anthony Pompliano?

  Yeah. Oh, yeah, yeah, yeah.

• 1:03:50Speaker 02

  And.

• 1:03:51Anthony Pompliano?

  Eli, Ben Kaplan.

• 1:03:52Speaker 02

  Yeah. And so we thought it'd be funny just to use the word fuck like for everything. Like they really fucked up. Fuck Jerry fucked up by fucking the customers.

• 1:03:59Anthony Pompliano?

  Yep.

• 1:03:59Speaker 02

  Out of, and so Goldman got mad at us and pulled out.

• 1:04:02Anthony Pompliano?

  Because you had the ad.

• 1:04:03Speaker 02

  We said, yeah, we said fuck too many times.

• 1:04:05Anthony Pompliano?

  Yeah. Oh, that's fine.

• 1:04:07Speaker 02

  Yeah.

• 1:04:07Anthony Pompliano?

  At least you didn't put the F word in front of Goldman, right?

• 1:04:10Speaker 02

  Yeah. And so we got in trouble with them, but yeah, we have like a team, a sales team and, and some people, we, we sell on opens. But we definitely have to make money for them.

• 1:04:20Anthony Pompliano?

  For sure. And so as you think about this now, uh, what's next, right? So you got trends, you'll go eventually and add a higher tier subscription. You've got the podcast. Will you go do more podcasts?

• 1:04:31Speaker 02

  Yeah, we'll do more podcasts. Basically, I look at our business like a funnel. We have top of funnel, which is ad-supported content. So podcasts, free newsletters, social and things like that. And then we have a little bit lower down the funnel, which is trends. That's two ninety nine, three hundred dollars a year. I think in the next handful of months, we're going to raise it to six hundred dollars a year. So sign up now.

• 1:04:50Anthony Pompliano?

  With the code POP so you get 50% off.

• 1:04:51Speaker 02

  Yes. Um, and then, um, and then we have one below that, and that's our events. Events costs hundred dollars, sometimes, no, as cheap as twenty dollars, all the way up to two thousand dollars. And then one below that, we'll have something that's 10 or 20 grand a year. And I want to do in-depth research for different industries and companies. And then one below that is I eventually want to invest or start businesses based off of interesting insights that we discover.

• 1:05:14Anthony Pompliano?

  So like what you said with the hotels, basically, could you take an insight you learned at, after analyzing the hotel industry and then go?

• 1:05:19Speaker 02

  Yeah, I've already personally invested in things that we discovered.

• 1:05:21Anthony Pompliano?

  Yep.

• 1:05:23Speaker 02

  But I want to do it at scale.

• 1:05:24Anthony Pompliano?

  Can you talk about one of them? Like, is there an example that you can talk about that doesn't screw you up?

• 1:05:28Speaker 02

  I'll talk about one. Yeah, it was keto ramen.

• 1:05:31Anthony Pompliano?

  What is that? Oh, like keto, like the diet?

• 1:05:34Speaker 02

  Yeah, like low carb ramen.

• 1:05:36Anthony Pompliano?

  Okay.

• 1:05:36Speaker 02

  And, because we were talking about keto cereal. People are searching for keto cereal like crazy.

• 1:05:40Anthony Pompliano?

  Yeah, but I think there's somebody who's started to build this now, right?

• 1:05:42Speaker 02

  Yeah, Magic Spoon. And then we talked about this months ago, in cereal school.

• 1:05:46Anthony Pompliano?

  Cereal school.

• 1:05:47Speaker 02

  And we started like, looking at like, different ways that that could be big. And it was ramen, and so I've invested in one of them.

• 1:05:54Anthony Pompliano?

  So you saw, hey, lots of people are buying keto cereal. They're searching for keto cereal, etc.

• 1:05:59Speaker 02

  What are people searching for? Where's other opportunity?

• 1:06:01Anthony Pompliano?

  Yep.

• 1:06:01Speaker 02

  And...

• 1:06:02Anthony Pompliano?

  And keto ramen was a huge one? And then basically you went and you found the keto ramen business?

• 1:06:06Speaker 02

  Yeah.

• 1:06:07Anthony Pompliano?

  So you had to go hunt. Like, I'm always fascinated by...

• 1:06:09Speaker 02

  This one was easy. I had a friend that was already kind of tinkering. So it worked out well.

• 1:06:14Anthony Pompliano?

  And they started the business based on your insight, or they were already...

• 1:06:18Speaker 02

  It was a collaboration. They were tinkering with it.

• 1:06:20Anthony Pompliano?

  Got it.

• 1:06:21Speaker 02

  And I'm like, yeah, you should go for this.

• 1:06:23Anthony Pompliano?

  Plana just walked in the room, so we're gonna talk a bunch of...

• 1:06:25Speaker 02

  That's my bag. You could throw it all down.

• 1:06:26Anthony Pompliano?

  We can't say anything bad about her anymore.

• 1:06:29Speaker 02

  Another thing was, do you remember the, these apps? They're called, it was called Hooked?

• 1:06:35Anthony Pompliano?

  Oh, wait. This is where they were like, sending push notifications, and it was like, part of the story?

• 1:06:39Speaker 02

  Yeah, like teens were reading like, thrillers?

• 1:06:40Anthony Pompliano?

  Yeah, yeah, yeah.

• 1:06:40Speaker 02

  Well, we analyzed that.

• 1:06:41Anthony Pompliano?

  Like, text message bites.

• 1:06:43Speaker 02

  Yeah, we're like, that's really interesting. But you know what the category that grows fastest and has the most liquidity is? Romance novels.

• 1:06:50Anthony Pompliano?

  Going back to the black werewolves that are...

• 1:06:52Speaker 02

  Yeah.

• 1:06:53Anthony Pompliano?

  Yeah, yeah, yeah.

• 1:06:53Speaker 02

  And so, I invested in a company that was doing serialized app content that was paid for, but it was meant for middle America moms, as opposed to like, teens, like, Hooked is.

• 1:07:04Anthony Pompliano?

  Yep. And so you basically, you can just use those insights, which obviously, if somebody wants to get those insights, they can go subscribe, and then use it to do the same thing you're doing.

• 1:07:11Speaker 02

  Yeah.

• 1:07:12Anthony Pompliano?

  Makes sense. What do you think about Barstool Sports? You know anything about them? I'm fascinated by taking the media model and plugging it into a massive business like Penny Gaming.

• 1:07:22Speaker 02

  It worked. I mean, what's the stock today? Did you see?

• 1:07:25Anthony Pompliano?

  I did not see. I'll look it up right now.

• 1:07:26Speaker 02

  If it's above 30, the other day it was 32.

• 1:07:30Anthony Pompliano?

  Uh, it's been going up, that's for sure.

• 1:07:32Speaker 02

  I bought a bunch when they, uh, announced it.

• 1:07:34Anthony Pompliano?

  Thirty-six.

• 1:07:35Speaker 02

  It's thirty-six?

• 1:07:36Anthony Pompliano?

  Yeah.

• 1:07:36Speaker 02

  Okay, it, when they bought it, it was twenty-four or twenty-two?

• 1:07:40Anthony Pompliano?

  Uh, twenty-five ninety-six one month ago, but I think they probably announced it a little bit after that. Oh, well, on the chart, it was twenty-five forty-two, and then there's a massive rocket ship up into the right of the stock.

• 1:07:50Speaker 02

  So, what's the difference between twenty-five and thirty-six? What's that, uh, forty percent?

• 1:07:54Anthony Pompliano?

  Yeah, something like that.

• 1:07:55Speaker 02

  Okay, so that means that...

• 1:07:56Anthony Pompliano?

  I'm not good at math.

• 1:07:57Speaker 02

  So that means it, it sold, that values it at around six-hundred and something million.

• 1:08:02Anthony Pompliano?

  Uh, what, Penn or Barstool?

• 1:08:04Speaker 02

  Barstool. I mean, what I mean is...

• 1:08:06Anthony Pompliano?

  Okay, so, so we can definitely talk about this, ready? Uh, Penn just did this, and, uh, Tesla just did this, where in both cases, they did something that was a catalyst that drove the stock price up, but the appreciation of the stock more than covered what they did. So, Penn bought Barstool, no-brainer, because they actually made money on that acquisition.

• 1:08:24Speaker 02

  Well, so they only paid a hundred...

• 1:08:26Anthony Pompliano?

  Hundred-and-fifty-three million, or a hundred-and-thirty-six million, I think.

• 1:08:29Speaker 02

  And then they have an option to buy the rest.

• 1:08:30Anthony Pompliano?

  Buy the rest, yeah.

• 1:08:31Speaker 02

  But their market cap, no, their market cap went up way more than...

• 1:08:34Anthony Pompliano?

  Yeah, they, they had a four-hundred-and-fifty-million-dollar price target on it, and...

• 1:08:38Speaker 02

  And they have a three-billion-dollar cap.

• 1:08:39Anthony Pompliano?

  Current market cap is four-point-two billion dollars.

• 1:08:41Speaker 02

  Yeah, so their, their market cap went up by more than a billion dollars.

• 1:08:44Anthony Pompliano?

  Yes, no-brainer deal for them, and then...

• 1:08:46Speaker 02

  And then, and then, uh, they also, uh, Portnoy, Dave Portnoy, and the company got a ton of Penn stock.

• 1:08:52Anthony Pompliano?

  Of course.

• 1:08:53Speaker 02

  So, they're crushing it.

• 1:08:54Anthony Pompliano?

  So, two things about Portnoy, I, I love the guy, uh, he's worth a hundred-plus-million dollars.

• 1:09:00Speaker 02

  Yeah.

• 1:09:00Anthony Pompliano?

  Right? Without the appreciation in the stock, and when, uh...

• 1:09:04Speaker 02

  He might get sued, though.

• 1:09:05Anthony Pompliano?

  When they, well, when they announced the deal, he, I heard him on a podcast, and he's like, "I have unlimited money." He's like, "For a guy like me, literally unlimited money." And you're just looking at him, and you're like, "Yeah, actually, like, given the life he lived for thirteen years before he ever raised money, before he did anything with Churnin, etc."

• 1:09:20Speaker 02

  And they sold that two years prior for a fifteen-million-dollar valuation, or maybe four years.

• 1:09:24Anthony Pompliano?

  No, no, four. So, yeah, so Churnin came in, I think they bought fifty percent of the business for like seven, seven-and-a-half million bucks, about fifteen-million-dollar valuation, uh, but to Erika Nardini and, uh, Mike Kearns and Churnin and all their credit, uh, Dave and, uh, Dan and all... They had no clue what they were doing from a business standpoint.

• 1:09:41Speaker 02

  They're idiots. They owned like horses and stuff.

• 1:09:44Anthony Pompliano?

  Well, Erica said she walked into their quote-unquote office and there was like uncashed checks lying around. And she was like, guys, what are you doing? They're like, oh, yeah, we should probably bring that to the bank. And she was like, alright, like, the bar of where we're starting is so low, like, I could definitely help here. And then, look what they did, turned a $450 million company in four years.

• 1:10:02Speaker 02

  Yeah, so you asked what I think about it. It doesn't really matter what I think about it. It worked. I think it's successful. Obviously, it's successful. It's great.

• 1:10:09Anthony Pompliano?

  Well, what would you do if you're Erica and Dave with that business now?

• 1:10:12Speaker 02

  It's so not, I mean, it's so obvious. You have a Barstool Casino. You have Disney World, but for grown men who want to get drunk and gamble, I mean.

• 1:10:20Anthony Pompliano?

  So, I also think they're gonna open their own pizza chain.

• 1:10:24Speaker 02

  Yeah, I heard that.

• 1:10:25Anthony Pompliano?

  Right? If they, if they make that move, if you go physical casinos, you keep up with the digital content, and you go pizza chain?

• 1:10:34Speaker 02

  I would just go and read the biography of Walt Disney and just do all of that. So like.

• 1:10:39Anthony Pompliano?

  Just re, oh, so you think like even go like all in on the physical locations?

• 1:10:42Speaker 02

  Yeah, but instead of a theme park, you have a casino.

• 1:10:45Anthony Pompliano?

  Yeah, which is basically a pen.

• 1:10:46Speaker 02

  I just do exactly what Walt Disney did, except for like 35 and 40-year-old dudes.

• 1:10:51Anthony Pompliano?

  Yeah.

• 1:10:52Speaker 02

  That's what I would do.

• 1:10:52Anthony Pompliano?

  Which they have.

• 1:10:53Speaker 02

  Yep. So it's not like, I'm not like smart for saying that.

• 1:10:56Anthony Pompliano?

  Yeah, yeah, yeah. Hey, look, that's obviously what they're gonna go do. And then Elon did this as well, but he said, hey, I'm gonna raise $2 billion, I'm gonna sell a bunch of the stock, and the stock went up $8 billion.

• 1:11:06Speaker 02

  Yeah, and then he got fined $20 million.

• 1:11:08Anthony Pompliano?

  No, no, no, this, this is last week.

• 1:11:10Speaker 02

  Oh.

• 1:11:11Anthony Pompliano?

  Last week, he comes out and, I guess like a month ago, he was like, I'm not gonna, I don't need to raise any more money, I'm not gonna do that. And then this week, or last week, he's like, yeah, I need to raise $2 billion, so I'm gonna sell some stock from the company, or issue new stock and sell it, but the stock went up $8 billion on that announcement. And so he basically created, right, $6 billion of delta in that transaction, plus he's got $2 billion.

• 1:11:32Speaker 02

  Well, both him and Portnoy, I think, are loose cannons and they could get in trouble.

• 1:11:38Anthony Pompliano?

  You think, why do you think Portnoy's gonna be in trouble? For tweeting about the stocks?

• 1:11:41Speaker 02

  Yeah.

• 1:11:42Anthony Pompliano?

  Do you see the tweets where he like puts the asterisk and then he's like, I know nothing about stocks, I own a fuck-ton of Penn stocks?

• 1:11:47Speaker 02

  I mean, look, I get like, I think it's funny and I love it. I don't know if the SEC will find it. I mean, we'll see what happens.

• 1:11:52Anthony Pompliano?

  Yeah, yeah, yeah.

• 1:11:54Speaker 02

  He has to have a lawyer like really close.

• 1:11:56Anthony Pompliano?

  There's somebody's gotta be looking.

• 1:11:57Speaker 02

  But, uh. I don't know. We'll see what the SEC thinks is funny.

• 1:12:01Anthony Pompliano?

  What other businesses in the media world are you fascinated by right now? Or you think are doing really interesting things?

• 1:12:05Speaker 02

  B2B business publishers.

• 1:12:08Anthony Pompliano?

  Like who?

• 1:12:09Speaker 02

  Um, there's this company called Informa.

• 1:12:11Anthony Pompliano?

  Okay, never heard of them.

• 1:12:12Speaker 02

  Yeah, most, never have. Um, have you heard of them?

• 1:12:15Anthony Pompliano?

  Yeah, most people. Planet just gave us the no.

• 1:12:16Speaker 02

  No, most people have never heard of them.

• 1:12:17Anthony Pompliano?

  If Planet hasn't heard of it, it doesn't exist. Go ahead.

• 1:12:19Speaker 02

  Google Informa market cap. It's traded on, uh, the English, or England, uh, it traded in England. It might be 13 billion.

• 1:12:26Anthony Pompliano?

  Uh, market cap, it says nothing.

• 1:12:30Speaker 02

  It's because they're not on the American Stock Exchange.

• 1:12:33Anthony Pompliano?

  Okay.

• 1:12:33Speaker 02

  I think it's, their revenue is three or four or five billion dollars.

• 1:12:37Anthony Pompliano?

  2.37 billion GBP.

• 1:12:39Speaker 02

  In revenue?

• 1:12:40Anthony Pompliano?

  In 2018.

• 1:12:41Speaker 02

  In revenue?

• 1:12:41Anthony Pompliano?

  Yes.

• 1:12:42Speaker 02

  Yeah, so I think it's a 13 billion dollar company.

• 1:12:45Anthony Pompliano?

  To USD, what is that in USD? So three, yeah, three, basically 3 billion dollars US in 2018.

• 1:12:52Speaker 02

  In revenue, yeah.

• 1:12:53Anthony Pompliano?

  So that's a 3.5, 4 billion.

• 1:12:54Speaker 02

  And their market cap is some number between 10 and 15.

• 1:12:57Anthony Pompliano?

  Okay.

• 1:12:58Speaker 02

  Well, what they do is they make money in a few different ways, primarily two different ways. They own 100 brands or so, maybe more, maybe less. Um, and they own, they're mostly B2B things. So for example, I think they own this, but let's just, it might be made up. They own like an agricultural brand that a lot of farmers, no, it's probably more specific. People who buy equipment for farming.

• 1:13:23Anthony Pompliano?

  Okay.

• 1:13:23Speaker 02

  Whether they're, they work at John Deere or something like that. And then they monetize that through subscriptions. Then they have a data side where if you want to figure out, um,

• 1:13:34Speaker 02

  I'm just making this up as I go, if you want to figure out, um, um, um, um, um, um, um, the best, the data on buying different parts and who's selling the best parts or what the projection is.

• 1:13:46Anthony Pompliano?

  What the most popular engine component is.

• 1:13:47Speaker 02

  Yeah, just like things, like information you need to run your business a little bit more effectively. Then they have a trade show where if you are John Deere, you'll have a booth there. And then the guy who makes the leather seats will have a booth there.

• 1:13:59Anthony Pompliano?

  Mm-hmm.

• 1:14:00Speaker 02

  And so, so you can, uh, sell to each other.

• 1:14:02Anthony Pompliano?

  Yep.

• 1:14:03Speaker 02

  Um, so that's how they make money in three different ways.

• 1:14:05Anthony Pompliano?

  So events, the actual data itself, and then the content.

• 1:14:08Speaker 02

  Yeah, so a lot of people don't know about it.

• 1:14:10Anthony Pompliano?

  3 billion dollars, a lot of money.

• 1:14:12Speaker 02

  It's stupidly profitable. Their trade shows, I did a big report on this. Their trade shows will do 40% income.

• 1:14:19Speaker 02

  Yeah, I mean, the trade show business brings in hundreds of millions of dollars in profit.

• 1:14:23Anthony Pompliano?

  Crazy.

• 1:14:23Speaker 02

  Um, and so I think they're really interesting, obviously. And so with our company, they're kind of like what I see us becoming.

• 1:14:32Speaker 02

  So I think that's really interesting.

• 1:14:33Anthony Pompliano?

  What else?

• 1:14:36Speaker 02

  I don't know. Um.

• 1:14:40Anthony Pompliano?

  I just want your free knowledge. You just taught me about Informa. What else you got?

• 1:14:43Speaker 02

  There's, well, there's loads of companies just like Informa that are a little bit smaller. Ascential. A S C E N T A L.

• 1:14:51Anthony Pompliano?

  A S C E N. Nope, I got it.

• 1:14:53Speaker 02

  It's another British company. A S.

• 1:14:55Anthony Pompliano?

  Why are they all in, uh?

• 1:14:56Speaker 02

  I don't know. They're all in Britain. All the trade show companies.

• 1:14:58Anthony Pompliano?

  Normally, E M A P is a British business to business media business specialized. That's a lot of businesses.

• 1:15:03Speaker 02

  It's a $400 million a year top line, 150 million in income.

• 1:15:07Anthony Pompliano?

  Yep.

• 1:15:07Speaker 02

  That's cool. And they do something similar. They own CANS. You know, CANS, the, uh?

• 1:15:11Anthony Pompliano?

  Yeah, the Advertising Festival.

• 1:15:12Speaker 02

  Yep, they own that. Have you heard of, um?

• 1:15:14Anthony Pompliano?

  That, that actually always just struck me as a way for the people who owned it to go on vacation on some of this time. Okay.

• 1:15:19Speaker 02

  Have you heard of, um, Money 2020?

• 1:15:21Anthony Pompliano?

  Yep.

• 1:15:21Speaker 02

  They own that. Um.

• 1:15:23Anthony Pompliano?

  Those conference businesses are really big and, and there's some guy, uh, in California who created a couple of these and sold them all just recently.

• 1:15:30Speaker 02

  Yeah, that's him. The guy who started Money 2020.

• 1:15:32Anthony Pompliano?

  Yeah. Who is that guy?

• 1:15:34Speaker 02

  He owns Shop Talk. It's a, a, a white British guy and an Indian guy, I think.

• 1:15:39Anthony Pompliano?

  All right, hold on. The guys behind the Money 2020 conference, what is this?

• 1:15:45Anthony Pompliano?

  Want to do the same thing in commerce, which is the shop talk.

• 1:15:47Speaker 02

  No, it's an Israeli guy, an Israeli guy and an Indian guy.

• 1:15:50Anthony Pompliano?

  Uh, Anil Agarwal, Simran Agarwal and Jonathan Weiner.

• 1:15:55Speaker 02

  Yeah, they, uh.

• 1:15:56Anthony Pompliano?

  Two of those seem to be relatives and one not so much.

• 1:15:58Speaker 02

  Yeah, they're cool. They're, um, they just sold. They just sold, they sold Money 2020 for 100 million and they sold Shop Talk for 150.

• 1:16:10Anthony Pompliano?

  It's crazy.

• 1:16:11Speaker 02

  Yeah, they're huge.

• 1:16:12Anthony Pompliano?

  Big businesses.

• 1:16:12Speaker 02

  Yeah. So I'm really interested in trade shows and things like that because I think with the digital age.

• 1:16:18Anthony Pompliano?

  People still want to get together.

• 1:16:19Speaker 02

  Yeah. So I think that's going to be quite big. Um, so that fascinates me. Um.

• 1:16:23Anthony Pompliano?

  What's the one thing you learned building the hustle that you wish you knew at the beginning?

• 1:16:27Speaker 02

  Well, just about building businesses, how to control your emotions and like the ups. I try and the ups to me are never that high and the lows aren't low at all now.

• 1:16:37Anthony Pompliano?

  Can we talk for a second? Let's not use names unless you want to say the names about how you ended up taking investment?

• 1:16:45Speaker 02

  Yeah, so we've raised money from Tim Ferriss.

• 1:16:48Anthony Pompliano?

  Oh, okay, he's gonna say the names.

• 1:16:49Speaker 02

  From Scott Belsky, the founders of NerdWallet, which, and with that Credit Karma news, they could be, maybe they're.

• 1:16:57Anthony Pompliano?

  Maybe they want to double down?

• 1:16:58Speaker 02

  Yeah, who knows what will happen there? I mean, that's a huge company. I say Scott Belsky, these guys are Behance, the founders of Bleacher Report, founders of The Chive, the founders of a couple of these old B2B media companies.

• 1:17:11Anthony Pompliano?

  So a bunch of like media.

• 1:17:12Speaker 02

  All media.

• 1:17:13Anthony Pompliano?

  Yep.

• 1:17:14Speaker 02

  Well, and so I didn't mean to raise money. Basically, I would ask for advice. There's this phrase, ask for advice, invest twice. So you, I would ask for advice and they'd be like, let me invest. And I'd be like, well, okay. And in my head, I was like, yo, I was 24, so I didn't know I was doing, but I was like, you're gonna give me money and I get to message you all the time and ask you questions?

• 1:17:34Anthony Pompliano?

  You're gonna pay me to be my friend, basically?

• 1:17:36Speaker 02

  Awesome. But listen to how I met Tim Ferriss was, he lived down the street from me and we would walk our dogs.

• 1:17:42Anthony Pompliano?

  In San Francisco?

• 1:17:43Speaker 02

  Yeah, we would walk our dogs in the park. And I knew who he was. I was a fan. And he just knew me as Sidney, as my dog, as Sid's owner. Maybe he knew my name, but I don't think he did. And we would just shoot the shit. I didn't want to like fanboy out too much, but I'd be like, hey, just listening to your podcast, it was good. You know, how's Molly? How's your, how's everything? Like, beautiful weather, just shooting the shit. And one day I get an email from Tim and he goes, hey, I love the hustle. Can we meet and talk about email? And I go, yeah, sure. And he goes, all right, let's do this restaurant in the neighborhood. And I show up and he goes, oh, wait, you're the dog's owner.

• 1:18:12Anthony Pompliano?

  Wow.

• 1:18:13Speaker 02

  Totally coincidental, yeah.

• 1:18:14Anthony Pompliano?

  And he didn't know when he emailed?

• 1:18:15Speaker 02

  No, no idea.

• 1:18:16Anthony Pompliano?

  Yeah.

• 1:18:16Speaker 02

  So that's how I met.

• 1:18:17Anthony Pompliano?

  Did you think that he knew?

• 1:18:19Speaker 02

  No, I never mentioned it. I never said a word.

• 1:18:21Anthony Pompliano?

  Yeah, I love it.

• 1:18:22Speaker 02

  Uh, and so that's why I met Tim.

• 1:18:26Speaker 02

  And so, yeah, I just would, like I said, I researched like crazy, so I use Webinar.

• 1:18:29Anthony Pompliano?

  And he wanted you to teach him about email.

• 1:18:31Speaker 02

  Yeah, he went, he went hard on email. And I was like, yeah, here's what we learned. And so he just kind of.

• 1:18:35Anthony Pompliano?

  Cause he's got, what is it, the five bullet Friday or whatever? I think it's become a pretty big list that he's.

• 1:18:39Speaker 02

  Huge.

• 1:18:39Anthony Pompliano?

  Yeah, he's going.

• 1:18:40Speaker 02

  It's quite big. And so now him and I will trade best practices on nerdy, the technical aspect like.

• 1:18:46Anthony Pompliano?

  You, you guys should create a subscription service where just people can subscribe to you and Tim texting.

• 1:18:51Speaker 02

  That would be awesome. We should.

• 1:18:53Anthony Pompliano?

  Like, I'm dead serious, right? If you think about, like, put you and like 20 other media folks in a text thread, and it's like, make, somehow make it so that people can only read. They can't, they can't actually.

• 1:19:05Speaker 02

  That's a great idea.

• 1:19:06Anthony Pompliano?

  And then all you do is you guys just have your normal conversations. Like, hey, man, what are you seeing with this? But whatever. People would pay, you know, 10 bucks a month and just see like, what are these 20 people all talking about to build their businesses? And they were just trying to steal your ideas.

• 1:19:17Speaker 02

  That's a great idea. But that, you know.

• 1:19:18Anthony Pompliano?

  I want 50% of the revenue.

• 1:19:19Speaker 02

  Too much, but that's what our podcast is, which is.

• 1:19:23Speaker 02

  We're, we're just like shooting the shit.

• 1:19:24Anthony Pompliano?

  If he created the text message thing, I was, I wanted 50% of the revenue, but he's already got the podcast.

• 1:19:29Speaker 02

  It's similar, but, uh, that's, that's a funny idea.

• 1:19:32Anthony Pompliano?

  Yeah, just, I, I've always been fascinated by, uh, previously, if you and I sat down in a private room, like, no one would like buy tickets, like, listen to us talk, right? But actually.

• 1:19:41Speaker 02

  Maybe.

• 1:19:42Anthony Pompliano?

  Yeah, but like, it would be hard to like actually execute on, what do they pay?

• 1:19:46Speaker 02

  And they only have a certain amount of people could show up.

• 1:19:47Anthony Pompliano?

  Yeah, like all kinds of stuff. But now that like a lot of communication is digital, uh, I actually think that that's going to become more popular over time. So it's like, how many companies are you a fan of that you think is really good at X, Y, or Z? And you'd actually pay to see their internal communications?

• 1:20:02Speaker 02

  So, uh, let me tell you this. I love that idea. And here's why. I read a ton of biographies. My favorite biography, two of my favorites are the biography of Joe Kennedy called The Patriarch. The second one is, um, Titan by John Rockefeller. I was obsessed with them for different reasons, but I really admired those guys, different aspects. Joe, Joe Kennedy was a, an asshole of a husband. So, but I like little parts of them.

• 1:20:21Anthony Pompliano?

  We can pick and choose here as to what parts we like about people.

• 1:20:24Speaker 02

  Right. And so I, I obsess over things. So I read those biographies and then. They would write letters to their families and there's other books that are not well-known. You gotta dig for them on Amazon and you could see their correspondence and I love doing that. And so what I love about the digital age with like this Elon Musk book, I'm like, show me those emails. I want to see all those emails back and forth. And so it's really fun when investors like tweet, when some company sells, they're like, here's the first pitch that they gave me an email. I'm like, yeah, that's awesome.

• 1:20:49Anthony Pompliano?

  You should take all of your emails, like from the beginning, the first five years or something, batch them all up and sell them to one person. There's somebody out there who would buy it.

• 1:20:59Speaker 02

  We'll call it Hillary.

• 1:21:03Speaker 02

  That, I don't care what side you're on. That was just a stupid joke.

• 1:21:08Speaker 02

  Just a dumb joke.

• 1:21:09Anthony Pompliano?

  There's a lot of people who pay a lot of money for those 33,000 emails.

• 1:21:12Speaker 02

  That's a stupid joke, but uh, that's a good idea.

• 1:21:15Anthony Pompliano?

  Yeah. Um, all right. Where, uh, people can go to thehustle.co.

• 1:21:20Speaker 02

  Thehustle.co if they want our free email, trends.co if they want our subscription. And I'm on Twitter. We all talked, all three of us in this room talked to each other on Twitter, the Sam Parr.

• 1:21:29Anthony Pompliano?

  Okay.

• 1:21:30Speaker 02

  Twitter's been my, it's awesome right now and you're huge on it. That's how I heard about you.

• 1:21:34Anthony Pompliano?

  Honestly, uh, I have no clue how Twitter does not make more money. How much would you pay to use Twitter a month?

• 1:21:42Speaker 02

  Dozens of dollars.

• 1:21:44Anthony Pompliano?

  Yeah, like.

• 1:21:44Speaker 02

  20 or 30, I mean, a lot.

• 1:21:46Anthony Pompliano?

  I legitimately think I would pay more than I would pay for Netflix for sure. I would, like, if you just go down the line of all the things that you pay subscriptions for, Twitter would probably be at the top of the list for me.

• 1:21:55Speaker 02

  All three of us met in this room on Twitter. I met you two on Twitter.

• 1:21:58Anthony Pompliano?

  Yeah.

• 1:21:59Speaker 02

  You guys met on Twitter?

• 1:21:59Anthony Pompliano?

  Yeah, she stalked me on the internet.

• 1:22:01Speaker 02

  That's awesome.

• 1:22:01Anthony Pompliano?

  It's a long story. We've never told the story on the podcast, but one day we're gonna make her tell it.

• 1:22:05Speaker 02

  I, uh, I posted on Twitter last night that I'm gonna be, I purposely rented a huge Airbnb and I says, I'm gonna have a dinner with 20 people. All, I had 100 people sign up to come, but I like limited it to only 20. All of them came from Twitter. Twitter's awesome. It succeeds despite itself.

• 1:22:20Anthony Pompliano?

  Yes.

• 1:22:20Speaker 02

  Dorsey.

• 1:22:20Anthony Pompliano?

  Which actually makes it super valuable.

• 1:22:22Speaker 02

  I love that.

• 1:22:23Anthony Pompliano?

  Yeah.

• 1:22:23Speaker 02

  I, uh, I, I buy Twitter stock. I think that Jack Dorsey needs to, uh, I like him as a person because he's weird. He should be fired and, um.

• 1:22:33Anthony Pompliano?

  So I'm, I'm actually, uh, in the opposite camp. I don't think Twitter would be as good as it is without Jack because I think that Jack. Either intentionally or accidentally protects it from what it is.

• 1:22:46Speaker 02

  So both can be true.

• 1:22:47Anthony Pompliano?

  Yeah.

• 1:22:47Speaker 02

  So, look, if you want to look at it as like a platform that does good for the world, then he should stay. If you want to look at it as purely just a like zuck and just get all money you can out of it,

• 1:22:56Anthony Pompliano?

  Yeah.

• 1:22:57Speaker 02

  he will not do it.

• 1:22:58Anthony Pompliano?

  Agreed.

• 1:22:58Speaker 02

  So it depends what you want. I, as someone who just wants to use it and I would sell all my stock, yeah, great. Stay there, Jack. Make it a public service and that just happens to make a profit.

• 1:23:09Anthony Pompliano?

  All right.

• 1:23:10Speaker 02

  I think Wikipedia Reddit and Twitter and Quora should all be like that.

• 1:23:14Anthony Pompliano?

  Yeah, that's fair.

• 1:23:16Speaker 02

  Like, just don't milk us dry. Just keep it like, okay.

• 1:23:18Anthony Pompliano?

  Yeah. Well, there are two or at least two, if not three of those are already doing that. So that's good. Last two things to talk about Bitcoin.

• 1:23:26Speaker 02

  Yeah, you guys want to hear a cool story? Okay, so.

• 1:23:28Anthony Pompliano?

  Yeah. By the way, this whole podcast originally started about Bitcoin. I never talk about Bitcoin anymore.

• 1:23:32Speaker 02

  Okay, this is a good one.

• 1:23:33Anthony Pompliano?

  All right.

• 1:23:33Speaker 02

  So.

• 1:23:35Anthony Pompliano?

  I know what you're about to say and it's so wild.

• 1:23:37Speaker 02

  Oh, 2013. No, 12, 2012.

• 1:23:40Anthony Pompliano?

  Okay.

• 1:23:41Speaker 02

  So 2012, I went to this party. It was called an animal print party. So we all wore animal clothing.

• 1:23:48Anthony Pompliano?

  Where'd you go as?

• 1:23:51Speaker 02

  I don't know. Oh, I wore like a onesie, a onesie like adult pajama that had like zebra on it.

• 1:23:57Anthony Pompliano?

  Okay.

• 1:23:58Speaker 02

  And.

• 1:23:58Anthony Pompliano?

  That's a shitty costume, but go ahead.

• 1:24:00Speaker 02

  I was 20 something, 22. It's all.

• 1:24:03Anthony Pompliano?

  At least you got dressed up.

• 1:24:04Speaker 02

  I got it from like dollar stores, some of the dollar store. Okay, so I met this girl, I started talking to this girl and we were hitting it off. I was single at the time and we were doing great and, you know, this big charming guy walks in and I like stare at him because he was wearing like a, he was wearing like a Speedo, an animal print Speedo. And he was like fit and tall and a good smile. And he steals the girl from me and starts chatting her up. And I end up start talking to the guy and I made friends with him, yada, yada, yada. And I friended him on Facebook afterwards and. We took pictures together.

• 1:24:36Anthony Pompliano?

  Okay.

• 1:24:37Speaker 02

  And I start following him on Facebook. His name was Ross. And I see on-

• 1:24:41Anthony Pompliano?

  Ross what?

• 1:24:42Speaker 02

  I'll tell you. I see on Facebook that he's like selling his truck for $2,000 because he posted the Craigslist link. I see that he's like an equities trader on LinkedIn. Just whatever. I wasn't like close with him, but I had hung out with him that day.

• 1:24:54Anthony Pompliano?

  He stole your girl. Yeah, we get it.

• 1:24:56Speaker 02

  And so a few weeks later, maybe a few months later, I come home from my house. I come to my house in Glen Park. And there's police at the library. And I'm like, what is going on? And I, and someone, Terry, my friend, she goes, Sam, Ross got arrested. I was like, for what? He goes, you know Silk Road? I was like, yeah, I know Silk Road. She goes, he started Silk Road.

• 1:25:16Anthony Pompliano?

  Holy shit.

• 1:25:17Speaker 02

  And I knew what Silk Road was. Like, I knew what, I knew a lot of, I mean, it was like this like scary, cool thing. That was Ross, Ross Albright. Albright, Albright?

• 1:25:27Anthony Pompliano?

  Yep.

• 1:25:27Speaker 02

  Um, that was him. And the next day-

• 1:25:30Anthony Pompliano?

  The dude in the speedo who stole your girl started Silk Road.

• 1:25:32Speaker 02

  It gets better. The next day, I go to lunch at my office and I, my coworker, his name was Billy. I go, Billy, did you see about this Silk Road thing? It was powered by like this whole Bitcoin thing? And Billy goes, yeah, my dad like loves it and he thinks it's gonna be huge. Well, Billy's last name, Billy Draper was his name.

• 1:25:50Anthony Pompliano?

  Yep.

• 1:25:50Speaker 02

  And his dad was Tim Draper. And I-

• 1:25:53Anthony Pompliano?

  And his dad kinda had a couple of Bitcoin.

• 1:25:55Speaker 02

  Yeah. And Billy, like, I wasn't that close to Billy and I try not to talk too much about his father because, you know, he's a big deal and you don't wanna fanboy out. But Billy was like, yeah, my dad thinks it's gonna be cool. And I was like, cool. I don't know anything about this, but if your dad says it's gonna be good.

• 1:26:09Anthony Pompliano?

  If Ross thought it was important?

• 1:26:10Speaker 02

  I was like, I'm in. And so I bought a bunch of it. And then for Christmas, I bought each of my family members $200 worth. And I think that turned into 10 grand. And they all laughed at me at the time. And then when it hit 20 Gs like a year and a half ago, I go, hey, mom, log into that thing called Coinbase that I sent you a login to and go take a vacation. And so they all sold it and took vacations.

• 1:26:28Anthony Pompliano?

  Oh, they sold it?

• 1:26:29Speaker 02

  I think they all sold half.

• 1:26:30Anthony Pompliano?

  Yeah.

• 1:26:30Speaker 02

  I go, just sell half and have fun.

• 1:26:32Anthony Pompliano?

  That's awesome.

• 1:26:33Speaker 02

  And that's how I heard about Bitcoin.

• 1:26:36Anthony Pompliano?

  That may be the best story I've ever heard.

• 1:26:37Speaker 02

  It's crazy, right?

• 1:26:38Anthony Pompliano?

  Yeah.

• 1:26:39Speaker 02

  Um, and then I read the book, American Kingpin, and they described my neighborhood. I live in the small neighborhood in San Francisco that very few people know about. And I was, it was right, like I hang, like I sit at the, at the seat where he sits all the time. That I used to hang out at that library.

• 1:26:51Anthony Pompliano?

  The story of how they got his computer is crazy.

• 1:26:54Speaker 02

  They just rushed him when he like, like a lady like, with like a, like a, I think a guy in the, it acted like a guy was hitting this woman or something.

• 1:27:01Anthony Pompliano?

  Yeah.

• 1:27:01Speaker 02

  And he goes, turned around and then they just swarmed him and they get him.

• 1:27:04Anthony Pompliano?

  They swarmed him and the part that I, that is this thing is they're like, yeah, they like shoved it across the, across the table. So he couldn't lock the computer.

• 1:27:10Speaker 02

  Yeah, then they run it to their van and they plug it into power.

• 1:27:13Anthony Pompliano?

  Which is fucking crazy.

• 1:27:15Speaker 02

  It was badass and that's my library. I literally live next door to that. It was crazy. This was crazy. I still, I took the photos down off Facebook, but I saved them on my Dropbox.

• 1:27:27Speaker 02

  It's, it's pretty wild. To me, it's like having pictures with Al Capone. You know what I mean?

• 1:27:31Anthony Pompliano?

  Yeah.

• 1:27:31Speaker 02

  Like, regardless if you think he did it or not, it's like a famous like figurehead for.

• 1:27:35Anthony Pompliano?

  Yeah, person, yeah. Do you ever think it'll get out?

• 1:27:39Anthony Pompliano?

  I don't know enough.

• 1:27:40Speaker 02

  I don't know where you fall on this and you're more passionate about Bitcoin. I think that if you try to kill someone, you should go to prison for a really long time. And here's, and, and I also, I used to have these kids that would sell drugs. I lived in Soma for a little while and these, these guys would sell drugs and I hated them for, for it. They would sell heroin and I was like, you fucking guys get off my block. You're ruining the neighborhood. And then I see him get arrested and I'm like, oh, he's this nice, like suburban white kid. And I'm like, wait a minute, no, no, no, no, no. If I'm mad at those guys, I need to also be mad at this guy.

• 1:28:07Anthony Pompliano?

  So I think there's a whole thing too about, uh, what drug it is, right? And I think this is changing in America in general. Like, one of the most fascinating trends right now in culture to me is this idea that, uh, like police departments are choosing what to decriminalize and what not to. They're not going to go decriminalize heroin, right? Like, like the hardcore stuff that is very easy to draw a line to, like this is killing people. I think will be illegal forever, if not for a very, very long period of time. But like marijuana, right? Especially like small possession of, or possession of small amounts, etc. You have some states like California, Colorado, etc. Who just like, look, we're from a legislative standpoint, gonna say that this is legal in some cases, or just for anyone.

• 1:28:48Anthony Pompliano?

  But then you have like the Baltimore police, who the DA just is like, hey guys, if you keep arresting people for this, I'm not gonna prosecute them.

• 1:28:53Speaker 02

  That's what they did in San Francisco.

• 1:28:54Anthony Pompliano?

  Yeah, you're just wasting, you're just fucking wasting your time.

• 1:28:56Speaker 02

  And that pisses me off, cuz I lived in the, I lived, I, I, I lived in Glen Park for most of the time I've been there. For one stint, I went to Soma, and then I came right back. And Soma, you know anything about San Francisco?

• 1:29:05Anthony Pompliano?

  Yep, I lived there for two years.

• 1:29:07Speaker 02

  It's trashy. I mean, it's bad. Like, there's trash everywhere.

• 1:29:09Anthony Pompliano?

  I was one of the smart ones. I lived up in the north part, in like the Russian hill.

• 1:29:13Speaker 02

  Okay, I lived in Soma, and every day I see these same kids, they keep bindles of heroin in their cheek. They keep it like that.

• 1:29:20Anthony Pompliano?

  I told this story before. I one time, recently was walking in San Francisco about to go into Starbucks, and I saw a guy who, again, I don't know for sure, but it looked like he was pretty homeless, just kind of really dirty, you know, clothes kind of jangled up, etc. And he knelt down, and he put a coffee cup down. He took out an iPhone, put it on top of the coffee cup, like he was holding it there. And as I was coming around the corner to walk into Starbucks, I just kind of looked down.

• 1:29:43Speaker 02

  Was like snorting it?

• 1:29:44Anthony Pompliano?

  Well, I was like, what is this guy doing, right? Like, he's like kneeled down outside the store, uh, store door, and he, he had a needle.

• 1:29:52Speaker 02

  Yeah.

• 1:29:52Anthony Pompliano?

  Again, I don't know if he was actually shooting up right there, or he was just putting like change in his pocket, or what he was doing, but I was just like, in what fucking planet do we live with? The guy's got an iPhone and a syringe.

• 1:30:00Speaker 02

  So, look, get this. I lived outside, it was the same, it, it was a group of kids from Guat- um, um, Guatemala, I think, or I forget. I got to, I started talking to them. I kind of understood how they worked. And I was so angry at them, because I would see these, I would, I, I lived there for a few years, a couple of years, and I would see the same, these same people buying drugs. I'd see them get worse and worse. And one day, one of them died on my office doorstep. And I went to like, I was like, hey, can you please move? My employees are coming. And she was dead. Okay? So I got to know these people, and I fucking hated those drug dealers. I hated, I was, I don't know who I hated. I was just angry.

• 1:30:34Anthony Pompliano?

  Yeah.

• 1:30:35Speaker 02

  I was pissed off, and I don't know what the right decision is, but I know that if I was, if I wanted those drug dealers arrested, which I did, I also, you have to... Yeah, I need to have that towards Ross, even though he was this like romantic, good looking, like free the people type of guy like you have to have a

• 1:30:52Anthony Pompliano?

  It's really hard to separate the actions from the impact, right? And I think that there's also, uh, there's this community of like, everything should be legalized, like you shouldn't be mad at people who like create software and marketplaces and all this stuff. But at the same time, then there's this thing of like, well, if you know people are selling drugs and people are getting hurt, then like, are you responsible or not? Which actually is very similar to like, should Facebook be responsible for the content that's on there? Like every marketplace owner.

• 1:31:19Speaker 02

  It's a challenging problem.

• 1:31:21Anthony Pompliano?

  And, and I kinda, to be honest, I'm, I'm kind of a, a little bit of a I don't take as much time to think about it as I probably should. So I have like a kind of stupid answer to this, but it's like, that's a super complex issue that's above my pay grade. And I actually don't know what the answer is, which is kind of a cop out, right? But like,

• 1:31:38Speaker 02

  Well, there is no answer. There's, there's, let's try this and see what there.

• 1:31:42Anthony Pompliano?

  And there's, and there's a spectrum of like, there's the hardcore believers on one end. There's a hardcore believers on another end. And there's everyone that's in the middle. And like, they all disagree. And that's where you get all of the chaos.

• 1:31:50Speaker 02

  But don't forget, he tried to kill three people and they thought he killed one, he thought he killed a couple of them and then kept going, right?

• 1:31:55Anthony Pompliano?

  Yeah.

• 1:31:55Speaker 02

  So like, that's a whole separate issue.

• 1:31:57Anthony Pompliano?

  Of course.

• 1:31:57Speaker 02

  So, um, as much as I

• 1:31:59Anthony Pompliano?

  And he stole your girl. Like that, that might be the most important part is like,

• 1:32:03Speaker 02

  Her name was Sasha. I remember it specifically. Um, I don't think she's listening to this, but, um, Yeah. So my thing is like, I, I loved reading about his book and I, it was such good writing that I was like, yeah, go Ross. Like, but then you gotta like, take your emotions out of it. Be like, I mean,

• 1:32:20Anthony Pompliano?

  Yeah.

• 1:32:21Speaker 02

  A lot of bad stuff. So it's really challenging.

• 1:32:23Anthony Pompliano?

  All right. Uh, last question for you, and then you get to ask me a question to end. Uh, aliens believer, non believer?

• 1:32:30Speaker 02

  Believer.

• 1:32:31Anthony Pompliano?

  Why?

• 1:32:32Speaker 02

  It just doesn't make, the math doesn't work out that like, we're this floating rock in this massive existence and we're the only things that are like us. I think that aliens don't probably maybe don't exist in the like, we think of as like two legs, two arms, like, but in terms of, uh, living, maybe they don't even live, like maybe the word living doesn't even apply, but like, there's some smart thing out there. Yeah.

• 1:32:56Anthony Pompliano?

  Are you more fearful of what's in space or what's in the ocean?

• 1:33:00Speaker 02

  Great question. Um, so both. If you-

• 1:33:05Anthony Pompliano?

  You're like, "I'm not fucking with anything."

• 1:33:06Speaker 02

  If you said you'd give me a hundred thousand dollars to go to space for a day, I would not do it.

• 1:33:11Anthony Pompliano?

  For one day, you wouldn't do it?

• 1:33:12Speaker 02

  Nope, not a chance.

• 1:33:13Anthony Pompliano?

  Why?

• 1:33:13Speaker 02

  It's scared. I hate flying. I don't do any drugs and I don't drink, but when I fly, I take Xanax. I hate, I hate elevators. I don't like flying. Like coming up to the 53rd floor in here, I did not like.

• 1:33:24Anthony Pompliano?

  What about going down into the earth?

• 1:33:26Speaker 02

  If you offered me, not a chance. If you offered me 10 grand for a one day cruise, I wouldn't do it.

• 1:33:31Anthony Pompliano?

  Oh, just for a cruise out in the ocean, not even to go down in the ocean?

• 1:33:35Speaker 02

  Not even a chance. So I hate both of them.

• 1:33:37Anthony Pompliano?

  Most people pay to go on the cruise.

• 1:33:39Speaker 02

  I think about this a lot. I'm like, what is my threshold for a three day cruise? Might be, oh, fuck. It could be as high as 60 grand.

• 1:33:47Anthony Pompliano?

  $60,000, somebody could pay you to go on the boat for three days.

• 1:33:50Speaker 02

  I don't even know if I would do it then.

• 1:33:52Anthony Pompliano?

  So I, I forget, and maybe Joe remembers, uh, who this is, but there's this guy on YouTube. He, uh, he does like, not pranks, but like kinda stunts, right? And one of them, uh, he put a million dollars in single, single, single dollar bills into a box and took four people and put their hand on the box and said, "Last one to take your hand off, wins the million dollars." And they went for like 72 hours or something, you know, like really peeing in bottles and like the whole, the whole nine yards. Uh, and he films the whole thing, right? And it's like this crazy viral video. Uh, and so I always think about like, what are other things other than like, keep your hand on the box? And like, for you would be like, you and five other people who are scared of a cruise ship, put them out, literally just far enough where you could see land, but you can't come back until you tap out?

• 1:34:33Speaker 02

  Unless I could be heavily medicated, I wouldn't do it.

• 1:34:35Anthony Pompliano?

  You wouldn't even go out there?

• 1:34:36Speaker 02

  No, I've like, it's really bad. It like holds me back. Like I don't, I don't travel a lot because of it. I hate it.

• 1:34:41Anthony Pompliano?

  When the aliens come, I know who not to go hang out with, because you're not hiding anywhere good. Uh, what question do you have for me to finish this up?

• 1:34:49Speaker 02

  Um, you're in the military, right?

• 1:34:51Anthony Pompliano?

  I was.

• 1:34:52Speaker 02

  What is the single biggest takeaway? Convince me to join the military. What can I learn?

• 1:34:58Anthony Pompliano?

  You can't convince somebody.

• 1:34:59Speaker 02

  Okay, um, I guess make me, tell me-

• 1:35:02Anthony Pompliano?

  Well, let me, hold on, let me take that back. Uh, there's a specific type of person- Yeah, there's a specific type of person that you can convince, but it's not for the reasons that most people think. So you can convince-

• 1:35:15Anthony Pompliano?

  22 and younger men to join based on danger, fun and the like adrenaline of it all.

• 1:35:25Speaker 02

  Just excitement.

• 1:35:25Anthony Pompliano?

  So, yeah, so it's just like, the way I thought about it, I signed up when I was 17. I knew I was gonna go to college, uh, already knew I was gonna go play football, but I signed up for a contract that basically like, let me go do that and then I was gonna owe time. But the way that I did it, uh, I got deployed when I was a junior in college, right? So they pulled me out of school to go, came back, finished school. When I was 17 years old, I had to go to my parents to get them to sign off. My dad literally said to me, "I'm not fucking getting involved in this. Go talk to your mother. She's the one who's gonna like, kill me if I ever sign that paper." So my mom was like, "No, no, no, no, no." Finally she agrees. And, uh, in hindsight, why did I join? Cause it was basically like, summer camp, but they gave us guns. Right? Like, the concept of war, completely not in my head. Like, the concept of danger, not in my head, whatever. It was like,

• 1:36:07Anthony Pompliano?

  "Dude, you're gonna go, you're gonna like, do a bunch of physical activity. They're gonna yell at you." I was like, "That's pretty much my life anyways, at like, football or family, whatever." And then they're gonna like, teach you how to like, do things in the water, or like, jump out of this, or, you know, whatever. They're gonna teach you to shoot. Like, I was like, "This sounds fucking awesome. Like, no, I would pay people to go do this, but instead they're gonna pay me? Like, sign me up." So that, like, very specific age group, you can convince, after that, it becomes very politicized, very like, ethos-driven. Like, it's almost like you become too smart to be convinced by the like, "Hey, there's adrenaline here."

• 1:36:39Speaker 02

  So do you regret it?

• 1:36:40Anthony Pompliano?

  No, not at all. Like, it was the best thing that I did, especially cause I did it when I did it.

• 1:36:44Speaker 02

  Was it good for discipline?

• 1:36:45Anthony Pompliano?

  Uh, it was really good with dis- I, I was pretty disciplined already, but I think what it did was it taught me, like, the importance of self-discipline. Right? Discipline being like, I played football, I went to school. Like, there was a lot of discipline and structure in my life already, probably because my father knew that I needed that, or I'd be a shithead. But what this taught me, I think, was more of like, here's the reasons why you should impose the discipline on yourself. And if you, uh, what is the guy's name? Uh, Jaco Willnig?

• 1:37:09Speaker 02

  Yeah.

• 1:37:09Anthony Pompliano?

  Like, uh, one of his big things is like, discipline equals freedom. And I think like, that's so true, uh, but people don't realize that the discipline component there is less about like, move your right foot, move your left foot, and it's more about having like, Okay, I want to build a company, right? I'm gonna actually spend the time necessary to do this and I'm not gonna give up, right? Or I have to go learn certain things, etc. And so, the military isn't as rigid or like top-down as people think it is. It's much more like, the sergeant shows up to his team and says, "Hey guys, we gotta go like, solve this problem, like, how are we gonna do it?" And so, there's a lot of creativity that goes on, but it's within a structure.

• 1:37:46Speaker 02

  Were you depressed when you left?

• 1:37:48Anthony Pompliano?

  No, not at all. I was too dumb to be. Like, I was...

• 1:37:51Speaker 02

  Well, I think my hypothesis was a lot of people would get depressed when they leave, because a lot of men don't have the... Like, when you're in the military, you have a mission and you have camaraderie.

• 1:37:58Anthony Pompliano?

  Yeah, so, one of the things that I credit a lot to, like, a lot of guys that I went to Iraq with and also served in the military, a lot of suicides, a ton of guys got arrested after we got back. I mean, literally, a guy pistol-whipped somebody in a parking lot, you know, DUIs, all kinds of crazy shit that went on. And a lot of it was like, either PTSD specifically, or like, similar types of reactions to all this. But for me, I went from being a normal kid to playing football, right? Which is all-male camaraderie, semi-violent sport, you know, all of the kind of us-versus-them, etc. To the military, which is still all-male camaraderie, etc. for my unit, us-versus-them, etc. When I came back, I went back to playing football.

• 1:38:42Anthony Pompliano?

  So, it was kind of like an escalation of violence and camaraderie, etc. And then a de-escalation on the way out, which, at the time, you don't understand, right? But in hindsight, like, super, super helpful for me. It's really sad that other people literally went from, "We're at war", two weeks later, they're like, back at their job as a prison guard, working in a hardware store, etc. I have no clue how those guys dealt with it. And two, I was a single 21-year-old kid, like, "Let's go drink beers and enjoy college-type stuff", these guys are going back and like, they have a wife and two kids.

• 1:39:12Speaker 02

  Yeah.

• 1:39:13Anthony Pompliano?

  I was like, "How do you go back into that environment?", I have no fucking clue. So, it makes a lot of sense why guys have the reactions they have, especially when you kind of like the combat units. But I was just super lucky in that I kind of had a de-escalation out of it.

• 1:39:25Speaker 02

  Good answer.

• 1:39:26Anthony Pompliano?

  You want to join?

• 1:39:27Speaker 02

  No.

• 1:39:28Anthony Pompliano?

  I think I would still get a bonus for signing somebody up.

• 1:39:30Speaker 02

  I think I'm too old.

• 1:39:32Anthony Pompliano?

  How old are you?

• 1:39:32Speaker 02

  I'm 30.

• 1:39:33Anthony Pompliano?

  30? Oh, I'm older than you. I'm 31.

• 1:39:35Speaker 02

  But you can't be, you can't enlist if you're...

• 1:39:37Anthony Pompliano?

  No, you can't. Yeah, yeah.

• 1:39:37Speaker 02

  Oh, you can?

• 1:39:38Anthony Pompliano?

  There's people who are 36.

• 1:39:40Speaker 02

  I would want to spend a week or two, maybe even like three or four months, um, getting all of the benefits, but none of the downside, like having risked my life.

• 1:39:47Anthony Pompliano?

  So there, I, I forget the program. God, I need to come up with, uh, I need to come up with the name of what this is. But there's a program that basically will put you through like very, very similar to SEAL training. But it's not in the military. It's like a private, uh, thing and it's, uh, all run by ex-Seals and they, they basically know there's a bunch of people who want to discipline.

• 1:40:05Speaker 02

  A lot, a young men in America don't exactly have like a rite of passage from like, you're a boy to you're a man.

• 1:40:09Anthony Pompliano?

  Yep.

• 1:40:10Speaker 02

  And what that creates is a lot of 25, 35-year-old boys. And I'm like, man, if, I wish there was a thing.

• 1:40:17Anthony Pompliano?

  Yep.

• 1:40:17Speaker 02

  It's like you've accomplished, you are now a man. Like there's no task, there's no journey.

• 1:40:21Anthony Pompliano?

  So back in, uh, oh man, I'm going to get this wrong. I think it's Sparta. Uh, I read this. I do not know if this is true.

• 1:40:26Speaker 02

  But they made you go out and like kill?

• 1:40:28Anthony Pompliano?

  Uh, so there's a whole bunch of stuff, like some of it was like when you're a kid, they put you out in the winter and whoever survived, oh, you know, who, who knows what's true, who's not. But I heard that there was, uh, I think it's Sparta, and I think that the person who did this is, uh, Dr. Sepa, uh, on Twitter. He's always, uh, tweeting, um. But they basically made you run 10 miles with water in your mouth and you couldn't drink the water?

• 1:40:48Anthony Pompliano?

  So when you got to the end, you had to spit it out?

• 1:40:50Speaker 02

  That's crazy. That's cool. I think.

• 1:40:52Anthony Pompliano?

  And like, and like, you know what I mean? Like we couldn't today ever imagine somebody doing that. That would be like the most viral video of all time, right?

• 1:40:58Speaker 02

  That's awesome.

• 1:40:59Anthony Pompliano?

  And then everyone on the internet would be like, he cheated somehow, right? But like those types of things around discipline, physical fitness, et cetera, are very similar to, I think, what like the military provides. And I've told plenty of a million times, like, I was 17 when I went to basic training. I was 20 when I went to war, right? You're literally too dumb and too naive to understand danger, one, but also two, like when the drill sergeant, when you're 17 years old, you're like, do more pushups, like run, whatever. You're literally like, oh, my football practice. Like you just are like, ah, whatever. Like everyone in my entire life has yelled at me, like this guy versus my parents. Like what's the difference? I don't, this guy could actually beat me up. Like my parents couldn't actually do anything, right? When you're 25 or 30, you're like, hey, man, you're not gonna talk to me that way.

• 1:41:41Anthony Pompliano?

  Right? Like, you almost have this, like, false sense of, like, self-importance or ego. And so I was there with guys who were 30, and I'm like, how are you getting yelled at? Like, right? Very, very different life.

• 1:41:52Speaker 02

  That's a cool answer.

• 1:41:54Anthony Pompliano?

  All right. Thehustle.co.

• 1:41:56Speaker 02

  Thehustle.co for free email. Trends.co, if you want to sign up, use P-O-M-P for 50% off. And thesampar.

• 1:42:04Anthony Pompliano?

  At thesampar.

• 1:42:05Speaker 02

  On Twitter, yeah.

• 1:42:06Anthony Pompliano?

  And he'll DM you and get you to sign up anyways.

• 1:42:08Speaker 02

  I will try.

• 1:42:09Anthony Pompliano?

  All right. Thanks so much for doing this.

• 1:42:11Speaker 02

  Thank you.

• 1:42:12Anthony Pompliano?

  Hey, everyone. Pop here. If you liked this episode of Off the Chain and want to help us take crypto to the top of the Apple, Spotify, and other podcast charts, please do us a favor and rate, review, and subscribe. To review, simply go to the Off the Chain homepage, scroll down until you see the five blank stars. Taking 15 seconds to fill those stars in and leave a quick review goes a long way in helping us take the entire crypto ecosystem to the top of the charts. I appreciate you listening and see you next time on Off the Chain.