Framework
The platform-jump play: YouTuber to pay-per-view millions
Shaan breaks down why the Paul brothers' move into boxing is a genius business model: selling pay-per-views is one of the best things a single person can do, and each event simultaneously grows their brand for free via media coverage.
“I think that this move they did to go from YouTuber, Viner to YouTuber, and then YouTuber to basically one of the best business models you can do as a as a single person is basically sell pay-per-views. And why is that right? So like this fight, I wouldn't be surprised if they sold 1 million pay-per-views. And so you sell 1 million pay-per-views at, you know, roughly $60 a pay-per-view, you know, per pay-per-view, you know, that's $60 million.”
Steal thisBuild an audience on a cheap platform, then graduate to a monetization model where a single event can net millions while compounding your brand.
Take
The best marketers don't spend a dime
Shaan's thesis: Elon Musk sells cars and launches rockets without running commercials, and Jake Paul sells millions in pay-per-views by hijacking attention. Some operators win by commandeering free attention in the news rather than buying ads.
“And, you know, Tesla never runs a commercial. Jake Paul is like, does the same. He's going to sell millions of dollars of pay-per-views for this boxing match that he has coming up without a commercial. And I said the best marketers don't spend a dime, right?”
Steal thisEngineer attention-grabbing moments that the press and social media spread for free instead of paying for ads.
Story
Jake Paul's 'Gotcha Hat' triple-pump PR stunt
Jake Paul stole Floyd Mayweather's hat at a press conference; when it went viral he rushed 'Gotcha Hat' merch onto his store and sold out, then tattooed 'Gotcha Hat' on his leg for a third wave of press — milking one stunt for repeated free attention.
“He has his merch guy create gotcha hat hats, puts it up on his store, sells out of gotcha hats, gotcha hat hats. And then he gets a tattoo on his leg that says gotcha hat and posts that. That goes viral that Jake Paul got a tattoo of the thing that just happened. So he got a double pump. A second pump of news PR out of it.”
Story
Shaan's 'Jake Paul of journalism' Twitter kill shot
After a NYT writer attacked Shaan for calling the Paul brothers great marketers, he replied 'You are the Jake Paul of journalism' — arguing her own self-promotion playbook (pick fights with big tech names, turn the blowback into a story) mirrors Jake Paul's. He got blocked instantly.
“And so I just go, "You are the Jake Paul of journalism." Oh my gosh. Got blocked instantly. And a bunch of people were— that got a big reaction out of people. Now, I thought this was the perfect kill shot. Why? Because that's not an insult to me. So first of all, it's true. Her brand of self-promoting herself as a journalist is confrontation.”
Take
A niche following beats a giant one if you can move them
Jake Paul argues a small, loyal audience is more powerful than a huge passive one — the test is whether you can actually move them across segments. His example: a yoga instructor with 10,000 followers who gets 1,000-2,000 of them to pay for a course.
“I look at people who have niche followings almost as more powerful because it's what audience are you influencing over? And, you know, are they listening to what you're saying? You know, can you move them into different segments? Like there's people who have maybe 10,000 followers. Like I know this yoga instructor, she has 10,000 followers, but she has like a course where 1,000 people or 2,000 people are paying her to teach them yoga.”
Story
Jake Paul tripled IRR on his first fund, TGZ Capital
Jake Paul says he started angel investing at 18 and launched a fund called TGZ Capital in 2019 that invested in over 20 consumer startups. He claims the fund is seeing exits and has roughly tripled its invested capital.
“And then I also had a fund when I was 2019 called TGZ Capital. We raised a pretty decent amount of money but was just getting my feet wet into the tech business, but invested into over 20 consumer startups. And the fund is performing well. We're seeing exits and we're basically tripling— we basically tripled our IRR capital.”
Story
Jake Paul wants to be his generation's Jay-Z or Dr. Dre
Asked why he invests, Jake Paul says it's partly about having his finger on the pulse and partly legacy — he wants to be the bridge between the business world and the influencer world, like Jay-Z or Dr. Dre were for music, building billion-dollar companies rather than just being a rapper.
“I think part of it's just legacy for me. Wanting to be this generation's Jay-Z or Dr. Dre, where, you know, they're a part of these massive billion-dollar companies and do more for the celebrities around them than just be a rapper or just be a producer. You know, I want to be that bridge between the business world and the influencer world and be sort of the one that— the influencer or celebrity who's known for that in this generation.”
Take
Never invest off a 3-minute pitch from someone who isn't the founder
After Sam asks whether Jake and Jeff would cut Zed Run a check, Jake deadpans that he wouldn't decide to invest or not based on a 3-minute spiel from people who aren't the founders. Shaan concedes it was a trick question.
“Invest or not invest into a company based off of a 3-minute spiel from not the founders.”
Steal thisDon't form an investment decision from a secondhand pitch — get in the room with the actual founders.
Fact
Creator-platform economics are an unstable equilibrium
Jake Paul argues YouTube creators capture a tiny, lopsided share of the value they generate, which is why top creators are fleeing to OnlyFans, BitClout, and their own subscription platforms. Woo frames it via Netflix: YouTube gets billions in content for free and kicks back an ad-rev split.
“It's very one-sided. And I think that's why you see, you know, YouTube and creators not as, you know, in sync as before, because they're finding ways to go off platform and make money like OnlyFans, Bitcloud, their own subscription platforms. So it's not the same ecosystem that it was before, but even before it was still very, very lopsided.”
Idea
A trusted marketplace to find great social-media operators
Jake Paul names his biggest hiring pain: there's no place to find people who can run social end-to-end — edit, caption, tweet, make TikToks, generate ideas. Every company and influencer needs that person and can't find them; he says a marketplace for the best social-media people would blow up instantly.
“Everyone I meet ever is like, I need a social media person. I need someone who can edit film. Understand, post, do the captions, tweet, make the TikToks, come up with the videos. I need ideas. Like every single company, every single influencer needs that person. And there's— where are they? I don't know. I've had to— it took me a long, long, long time. My John right here, he's my guy. He's like, I'm right here. But But it's so hard to find them. It's so hard to find them. And so I wish there was a place where I could just go and be like, who's the best social media people? I think that would blow up instantly.”
Steal thisBuild a vetted marketplace (a 'Dribbble for social media operators') where top editors and content creators showcase work and get hired.
Idea
A $10K corporate bootcamp teaching companies to run social like Jake Paul
Sam pitches a B2B social-media school: charge companies $10,000-$15,000 to send employees through a 6-week, twice-weekly bootcamp with recorded talks from Jake and Logan plus live sessions with their editors. He thinks it could be at least a $10M/year business, modeled on the Miami Ad School.
“what you do is charge $10,000 to $15,000 and your employees would go to it and you would have recorded talks by Jake Paul, by Logan, but then you'd also be like, all right, now we're going to talk to these editors. They're going to show you how they do it. And it's a 3-week— no, you do a 6-week thing. You meet twice weekly for 3 hours apiece and you just have a curriculum and it's just like a boot camp. I'm pretty sure you could build at least a $10 million a year company doing just that.”
Steal thisSell social-media training to enterprises (not kids) at $10K-$15K per seat with celebrity-led curriculum.
Prediction
Hit
Shaan predicts Jake Paul beats Ben Askren because he cares more
On the record before the April 2021 fight, Shaan predicts Jake Paul will beat Ben Askren — reasoning that Jake cares more and will try harder, while Askren is at peace with a decision loss and will drop rounds.
“Jake, good luck at the fight. I think you're gonna win. Uh, sorry Ben if you're listening. I, I just think that, uh, Jake cares more and is going to try harder to win. I think Ben is, is okay with the decision, and because of that, I think he's going to lose rounds. That's my prediction. It's on the record.”
Number
Shaan estimates Jake Paul's media side at ~$10M/year
In the debrief, Shaan back-of-the-envelopes Jake Paul's media business: YouTube ad rev-share at a ~$5 CPM plus 7-figure sponsor deals, landing around $10M/year. Sam guesses higher, at $15-20M.
$10M
Estimated annual revenue, Jake Paul media business · USD/year
“How many monthly views does this video get? Okay, then you assume a $5 CPM for his YouTube ad, you know, rev share. And then you say, okay, he has these sponsors. I think they're going to be 7-figure, you know, I would say his media side of things should be bringing in about $10 million a year. That'd be my guess.”
Number
Sam guesses the Paul brothers sell $20-30M/year in merch
In the debrief, Sam estimates Jake and Logan Paul collectively sell $20-30M a year in merchandise, with Shaan adding that Logan's enterprise (Impaulsive podcast, Maverick brand) is likely the bigger of the two.
$30M
Estimated combined annual merch sales, Jake and Logan Paul · USD/year
“I bet you him and his brother sell collectively $20 to $30 million a year in merch.”
Take
Billy of the Week is whoever reinvents themselves 3-4 times
Shaan defines what makes a great 'Billy of the Week' character: someone who has reinvented themselves across 3-4 chapters of life. He maps Jake Paul's arc — Vine, YouTube, celebrity boxing, then rolling fund — as exactly that, all before age 25.
“I think if you, if you listen to like whenever we do Billy of the Week, it's usually somebody who's reinvented themselves and 3 or 4 different chapters of their life. That is interesting. And this guy's— I thought that was kind of cool how he's done that. He didn't say any of those things, but just when I was doing the research, I was kind of taken aback by, oh yeah, that's cool. He's already had like 3, 3 to 4 pretty interesting chapters before the age of 25.”
Take
Celebrity boxing beats Sugar Bear Hair ads for influencers
Shaan argues the Paul brothers' pivot to hosting celebrity boxing events is a far better business model than influencer sponsorships, potentially banking $5-10M per event. He estimates Jake Paul drove 30-40% of the Tyson card's pay-per-view buys, elevating the influencers to a different fame-and-fortune stratosphere.
“I would not be surprised if these guys are banking $10 million, $5 million every time they do one of these events. And they've done like one or two a year now for the last couple years. I think this is way better than doing, you know, Sugar Bear Hair ads, uh, you know, on your Instagram or whatever. It's a way better business model for these influencers.”
Steal thisConvert influencer fame into ownable, high-margin live events instead of one-off sponsorship reads; the events compound your fame and pay far more.
Idea
Rebrand Warheads with rotating celebrity-flavor packs
Shaan pitches buying a nostalgic extreme-sour brand like Warheads and licensing a rotating roster of athletes and influencers, each becoming a limited-edition flavor whose head is the packaging. Season one is NBA stars via Klutch Sports; season two is Jake Paul and the Team 10 crew.
“I would go to Klutch Sports and I'd be like, hey LeBron, uh, we need like 15 NBA athletes. You're each going to get your own Warhead flavor. LeBron, you're the, you're the black Warhead, you're the craziest, most sour one. And then we're going to go get, you know, Anthony Davis and Giannis and the other guys to be the other flavors. And then I would go to Jake Paul for the next season.”
Steal thisLicense a rotating cast of athletes/influencers as limited-edition product variants, using each face as the packaging to drive collectibility and built-in reach.