Apr 18, 2026 · 1h 3m · 20vc
Jake Paul: Traditional VC is Toast & Attention is More Valuable than Cash · 20VC with Harry Stebbings
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In this episode of the 20VC podcast, Harry Stebbings interviews media sensation Jake Paul and his Anti Fund co-founder Geoffrey Woo, exploring how they leverage cultural taste, attention, and distribution to disrupt traditional venture capital. The discussion covers Jake’s multi-faceted career, the strategic business of boxing, and their forward-looking views on technology, AI, and national defense.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 22.3% of the talking time here. How this is scored →
Harry as informed peer 4.0 Guest teaching 3.1 Guest disagreement 2.1 Harry pushing back 2.1
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 39:20 Jake Shuts Down Political Critics
Jake aggressively rejects political critics complaining about presidential leadership, telling them to go run for president and fix it themselves if they think they know better.
Hardest push from Harry ▶ 8:24 Harry Challenges 'Uncancellable' ClaimHarry directly refuses to let Jake off easily on public brand missteps, pressing him on whether he regrets asserting that he is completely uncancellable.
Biggest teaching moment ▶ 10:39 Jeffrey Corrects VC Division of Labor AssumptionJeffrey dismantled Harry's assumption that Jake only handles distribution while Jeffrey picks deals, explaining how Jake's product taste is their core picking edge over boomer VCs.
Harry holds his own ▶ 58:02 Harry Cites Early Ramp Dealflow HistoryHarry demonstrates his deep venture track record and industry access by sharing his personal story of meeting Ramp founder Eric Glyman during his pre-Ramp startup days.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Mapping the Jake Paul Business Empire | 5 | 2 | 1 | 2 | Harry shows solid preparation by citing specific conversations with portfolio founders like Wanda and W. He gently challenges Jake on whether the aspiration to become an influencer is healthy. | |
| Managing Institutional LPs with a Polarizing Brand | 4 | 2 | 3 | 4 | Harry presses Jake on whether his polarizing public brand hinders institutional LP fundraising and asks if he regrets calling himself uncancellable. Jake dismisses past controversies by comparing his actions to normal college frat behavior. | |
| Why Venture Capital Makes Sense: The Power of Taste | 5 | 6 | 4 | 3 | Harry uses a four-pillar VC framework to assume Jeffrey handles picking while Jake handles distribution. Jeffrey firmly corrects this assumption, arguing that Jake's cultural taste is their primary edge and dismantling traditional VC metrics. | |
| Selling Founders Distribution, Network, and Access | 6 | 3 | 2 | 3 | Harry cites Keith Raboy's framing regarding what product investors sell to founders and questions how they avoid brand dilution. Jake and Jeffrey explain their unique access value-add, including direct lines to global figures. | |
| Sniper Late-Stage Strategies & Incubating New Companies | 6 | 2 | 1 | 2 | Harry proposes a specific late-stage sniper investment thesis, suggesting they leverage personal brand to deploy large capital blocks into mature tech category leaders. The guests eagerly validate his thesis. | |
| Time Commitment to Venture & the Relevance Treadmill | 4 | 4 | 3 | 3 | Harry brings up the difficulty of staying relevant on media treadmills. Jake rejects the premise that he is on a treadmill, asserting that he and his brother have achieved escape velocity. | |
| Instinctual Cultural Taste and the Business of Boxing | 3 | 5 | 3 | 2 | Harry asks Jake to explain his secret to anticipating cultural taste. Jake compares giving away his strategy to a karate master revealing secret moves, but schools Harry on his 85% accuracy in predicting video metrics. | |
| Public Persona, Humanity, and Selling Fights | 3 | 4 | 2 | 3 | Harry asks if Jake ever regrets public trash talk before fighting massive opponents like Anthony Joshua. Jake explains the strategic financial math behind selecting opponents where losing still increases brand value. | |
| Technological Progress: Fear vs. Optimism | 4 | 5 | 5 | 3 | Harry voices deep concern over AI-driven job displacement and societal anxiety. Jake and Jeffrey forcefully dismiss Harry's fear framing, mocking European passivity and calling Europe the sick man of the world. | |
| Freedom, Family, and Jake's Childhood Drive | 3 | 3 | 1 | 1 | Harry asks about personal motivation and childhood drive. Jake reflects candidly on seeing his father cry during a divorce over selling a $150 snowboard, which instilled his relentless financial drive. | |
| Political Ambitions, Trump, and Running America as a Business | 4 | 4 | 4 | 3 | Harry presses Jake on whether Trump is doing a good job amidst global tensions. Jake passionately defends Trump as a founder president, shutting down armchair critics with forceful pushback. | |
| Tech Governance and Democratic Decision Making | 6 | 4 | 2 | 2 | Harry cites recent interviews with Anduril leadership regarding moral accountability in defense tech. Jeffrey offers an articulate breakdown of democratic legitimacy versus Silicon Valley tech hubris. | |
| Relationships and the Olympics Backstory | 2 | 1 | 1 | 1 | Harry shares a humorous personal story about his girlfriend praising Jake's support at the Olympics. Jake offers sincere relationship advice and discusses managing mental health through plant medicine. | |
| The Psychology of High-Level Work Addiction | 4 | 2 | 1 | 2 | Harry diagnoses high performers as work addicts and characterizes Jake's rapid sports escalation as psychopathic. Jake agrees completely, sharing details of his physically brutal track workouts. | |
| Pattern Recognition and Mental Edge in Boxing | 4 | 5 | 2 | 2 | Harry inquires about mental processing during fights. Jake attributes his boxing success to superior cognitive pattern recognition and reveals he takes home nearly 100% of fight revenues by controlling promotion. | |
| Training Camaraderie and Boxing Challenges | 3 | 2 | 1 | 2 | Harry questions why money still motivates Jake after earning tens of millions per fight. Jake clarifies that his goal is becoming world champion to complete an unmatched story of resilience for kids. | |
| Quick Fire: Boxing, Content, or Investing? | 3 | 1 | 3 | 1 | In a quick-fire round, Harry asks Jake to pick between being number one in boxing, content, or investing. Jake picks investing and jokingly calls out competitor VC Jason Lemkin on AUM. | |
| Jeffrey's Angel Investment Success and Ramp Story | 5 | 4 | 1 | 1 | Harry asks Jeffrey about top angel investments and recounts his own early encounter with Ramp founder Eric Glyman. Jeffrey details his high school summer camp roots with the Ramp founding team. | |
| Ambitions for the Public Markets | 4 | 2 | 1 | 1 | Harry asks what fund products Antifund lacks today. Jeffrey reveals plans to move into public market funds to leverage mass distribution across larger liquid capital bases. | |
| Outro, Friendly Banter, and Age Jokes | 1 | 1 | 1 | 1 | The episode wraps up with relaxed banter as Harry jokes about Jake previously guessing his age to be 36. |
Statements from this episode (35)
Jake Paul: Attention Is More Valuable Than Capital in Venture Investing
“It goes back to like one of our founding principles, which is attention is more valuable than capital.”
Geoffrey Woo: Jake Paul Represents the Aspirations of the Next Generation
“I mean, maybe the way, like, cause I, it's easier for me to brag about Jake, but I think the highest order bit is that I think Jake represents the next generation of Americans and what they want to be like.”
Jake Paul: Successful Video Content Requires Calculating Every Millisecond
“There's like so much genius in every .12 of content that I make. Like every little millisecond is calculated and dialed and thought through.”
Jake Paul Claims He Is Uncancellable Because He Has Done Nothing Bad
“That's the thing is I'm uncancellable because like no one will ever find or see anything about me that is actually bad. And it's all just like fake hate.”
Jake Paul: Anti Fund Aims to Manage $10B to $20B Eventually
“Yeah, I think if the 30 mil fund was, like, the end goal, it would be like, no, but, like, we want to run 10, twenty billion dollars at some point, and look up to people like, you know, Josh Kushner at Thrive, who started with, you know, I think it was four, f…”
Geoffrey Woo: Uber Burned Tens of Billions on Paid Marketing
“I just saw that Bill Gurley was tweeting that you know, paid marketing is, like, the worst form of marketing, and I'm just like, hey, Uber, like, he's most well known for kicking out Travis from Uber, and Uber burnt, like, tens of billions of dollars on straig…”
Geoffrey Woo: AI Commoditizes Technical VC Skills, Making Taste Dominant
“So, my sense is that The software and like the classic smart people stuff gets commoditized, and the attention, the taste, the culture side gets more and more important. So I think the world goes into our favor versus away.”
Geoffrey Woo: Jake Paul Intros Outperform Traditional 'Boomer Suited' VC Intros
“It's like, would you rather have a Jake Paul introduction or some random boomer suited VC make that intro? The response rate and the integration rate is like super high.”
Geoffrey Woo: Legacy VCs Are Vulnerable Because Original Founders Are Gone
“We can compete with the guys who've been doing this for 3040 years because, one, the founders of those funds have been dead or gone. It's just other guys who got hired into doing this, and I think we have a fresh take on saying, hey, Let's compete.”
Geoffrey Woo: European Defense Needs a Dedicated Neo-Prime Contractor
“I think with geopolitics, I think there needs to be like a European neoprime for defense.”
Jake Paul Is Involved Day-to-Day in Anti Fund's Venture Operations
“I think people don't realize, like, how involved I am, and we're constantly on a day-to-day basis talking, catching up, texting, in a constant flow, weekly calls, et cetera. So very, very involved, and flying to SF multiple times a year, meeting on the ground …”
Jake Paul: Remaining Relevant Is a Dying Market for Most Influencers
“So like I'm in a different league, but I think for other creators and influencers, it's like a dying market for sure, and it's very hard for people to stay in the know.”
Jake Paul: Most Creators Lack the Skill Set for Venture Investing
“It's a very tough game, and if you like actually aren't good at it or know how to do it, Then, like, maybe don't just, like, try to do it, because it's almost second nature to me, because I have vision and can see, like, where things are heading. I'm ahead of …”
Jake Paul's Team Predicts Video View Counts With 85% Accuracy
“Like me and my number one content guy before we post the video, we'll Predict how many views it's gonna get, and, like, pretty much accurate, like, 85% of the time.”
Jake Paul: Boxing Revenue Is Driven by Attention, Not Fight Outcomes
“Yeah, a hundred percent. Yeah, and, you know, like, it just, it's all math, right?”
Jake Paul: Losing to a Larger Fighter Is Better for Public Perception
“I was more nervous to fight Gervonta Davis because if you lose to, like, a tiny person people would be like, oh, you suck. So it's actually better to lose to a giant.”
Jake Paul: AI-Personalized Content Could Divert Viewers Away From Traditional Sports
“If I can put into Cognition, or any of these things, and develop my own game that's personally tailored for me with a couple clicks of a button. Why would I watch, you know, the NBA when, like, this game I made for myself has all my favorite things in it, and …”
Geoffrey Woo: Europe Is the 'Sick Man of the World' in Tech
“I feel like Europe is like the sick man of the world right now. I feel like Europe could have some of the foundational, civilizational, like of Western culture that came out of here, London, England, right? And it feels that like they're not seizing the opport…”
Geoffrey Woo and Jake Paul Spent Three Hours With the U.S. President
“I think we're, we got to spend, like, three hours with the president a couple weeks ago”
Jake Paul States Conditions Under Which He Would Run for U.S. President
“I would only want to do it if I was, A, the best person for the job, and if, B, there was, like, someone like Kamala Harris, like, running that, like, could have the potential to, like, ruin the United States, and I would have to, like, go and oppose them and,…”
Jake Paul: Donald Trump Is One of the Best U.S. Presidents
“I think he Is arguably one of the best presidents the United States has had in, in this term. There's so much propaganda and things, but at the end of the day he's doing an incredible job, and there's always gonna be criticisms.”
Geoffrey Woo: Donald Trump Operates Like a Bold Startup Founder
“Like, to me, I think he's like a very founder president, right? Like, I think he's, He actually makes bold decisions and tries to like mold the future. But I think a lot of politicians are just very much dictated by the flows of polling.”
Geoffrey Woo: Elected Leaders, Not Tech Founders, Should Decide Military Policy
“Like, I feel like it's a very egocentric to say that, hey, I built the tech. I get to make the decision for the rest of the world. If we believe in democracy, which we do, then it's like, okay, then the democratically elected leader Gets that call.”
Jake Paul: Anduril's Autonomous Technology Will Reduce Human Casualties
“Yeah, maybe less people will actually die because of their technology.”
Geoffrey Woo: Tech Leaders Are Becoming Politicians as Cultural Influence Grows
“The tech leaders are becoming more and more politicians because they have a bigger, bigger impact on culture, on society.”
Jake Paul Uses Psychedelics and Breathwork to Manage His Mental Health
“Dealing with mental health, like, my mind can become a, like, crowded and dirty and stressful place, and it's a practice every day to manage it, and I think that's where I've, like, fallen in love with breath work and meditation and spiritual journeys with aya…”
Jake Paul Claims His Mind Is Sharper Than Every Other Boxer
“That's why I think I got good at is because it's just my mind is better than other, probably every boxer.”
Jake Paul Claims He Would Be the Best Boxer With Lifelong Training
“If I had been doing it my whole life, I'd be the best boxer in the world for sure.”
Jake Paul: Only a Conor McGregor Fight Could Rival Mike Tyson Numbers
“I think that the one that, like, would just be the only one that would ever come close to the Tyson numbers is, is me versus McGregor, which would be fun.”
Jake Paul Retains Higher Payout Percentages Than Any Other Boxer
“I take the most home out of any boxer. Like, I have the best setup in, in boxing, because I'm my own promoter, and I'm the one negotiating with the platforms.”
Jake Paul Would Choose to Be Number One in Investing Over Boxing
“Investing. Actually, yeah. Yeah, a hundred percent. It's, I think, the, something that I can do forever, like, and it's really enjoyable, and I really love, like, Being a part of the cutting edge things in technology, and like, advancing society, and human evo…”
Geoffrey Woo: Anti Fund Achieved 10x Return on Aerodome in 18 Months
“Rahul Aerodome, that was a ton X in 18 months, rolled a lot of that stock in the flock safety”
Geoffrey Woo: Personal Angel Investment in Ramp Yielded a 300x Return
“But even on, just on the personal side, was Angel invested in Ramp, so that's like a, at a 50 mil entry value, so that's like a, whatever, 300 X on a personal side.”