Jake Paul: Traditional VC is Toast & Attention is More Valuable than Cash

Attention is more valuable than capital.

Can VCs become influencers faster than native influencers like Jake and Logan can become VCs?

I just hang out with Trump, and I go on stage and give a speech off the top. The first thing he says to me on stage when I turn around is, “Oh, you’re going to run for office someday.” Then we go backstage, and he’s like, “You should be the president.” Then he endorses me.

I think he is arguably one of the best presidents the United States has had in this term. Money buys freedom, and I think freedom makes people happy.

Boys, it is so good to have you in the studio. I’m so excited that we got to do this in person, so thank you for joining me.

100%, man. Thank you for having us.

Now, I want to start with the fund. This is a VC show first and foremost. I spoke to John at Wander, who is a portfolio company of yours, and he said that you’ve got to start by mapping out the Jake Paul business empire ecosystem to fully understand what it’s like.

Can you give us an overview of what the Jake Paul business empire looks like today?

1. The Jake Paul Empire

Yeah, so it goes anywhere from being a peanut farmer to fighting Anthony Joshua to venture, working with OpenAI and advising them. I have a ranch where I literally sell peanuts.

It’s entertainment mixed, obviously, with the entrepreneurial vibes. It’s Better, which is sports gaming. It’s—

I spoke to the founder beforehand.

Okay. Joey?

Yeah.

He’s great. He’s great.

Yeah, I spoke to Joey. Dude, I did. I was like, “Listen, are you—Jake is obviously investing with you guys?” He’s like, “No, he didn’t. He co-founded it with me.”

Yeah.

And so we had a lovely chat. Dude, I do my work.

Wow, you really talked to everyone.

Yeah.

You’re locked in.

Yeah.

But yeah.

2. Attention Beats Capital

This is why I like the show. Maybe the way—because it’s easier for me to brag about Jake, but I think the highest-order bit is that Jake represents the next generation of Americans and what they want to be like.

I think we have a unique opportunity to not just have Jake be an inspirational model, but also be a capital force and an attention force to drive a future and a culture that we want to see. If you look at it from just a demographic perspective, the number-one job that young people want to have is to be an influencer.

I think one of Jake’s personal missions is to inspire the next generation of young men.

Jake, are you proud when you hear that the number-one job aspiration is to be an influencer?

Yeah, and it’s funny. It’s been that way since I was 18. A company did a study when Vine and YouTube were popping, and I’ve known that statistic for the longest time.

But do you think that’s healthy? I didn’t think you wanted to be an influencer.

No, exactly. That’s what I tell people. They’re like, “Well, how do I be like you?” I say, “Don’t. Be yourself.”

Also, are you entertaining? You have to really ask yourself that question. Can you actually do this? Are you smart? Are you creative? Do you have the work ethic?

You know how much work you just put in for this one podcast. People don’t really see the behind-the-scenes work that goes into these videos. It’s become second nature to me, and I have a team and all that stuff, but it’s still a full-time job.

What do people not see, work-wise, that you wish they saw most?

They don’t see the—there’s so much genius in every 0.1 second of content that I make. Every little millisecond is calculated, dialed, and thought through.

I think that meticulous nature stems from being a creator on Vine, where you had 6.9 seconds. People thought it was 6, but it’s actually 6.9. Every second and millisecond had to be measured out, calculated, changed, and edited around.

I think that meticulous nature of what I do and create has obviously helped me since the beginning. It’s almost like politics with my team, where we’re arguing about every little second or the song in the video, or things like that that actually matter.

Do you lose the art in the science?

I don’t think so. I think the art happens when we’re filming. The science is in post and in the edit.

It goes back to the question of people wanting to be influencers, but are you naturally good at it? Are you naturally able to talk on camera and tell the story? At the end of the day, I’m a storyteller in a sense, and that’s the art.

It’s interesting. So are the best founders, and so are the best fundraisers. What makes a great story?

Conflict, struggle, and love would be the top 3 answers for that. I purposely invoke emotions in people as an entertainer. I want people to feel fear, joy, hate, or something.

I don’t care what they feel, but I know in certain videos what I’m going to make them feel. I posted an edit where I acted like I was depressed and couldn’t find meaning in my life. It went super viral because people were like, “Yo, are you okay?”

People were texting me, “Yo, are you okay? I saw your video.” I’m just like, “No, I’m just an entertainer. I’m just making people think I’m depressed.”

I think the boldness of character, too. Jake is very authentic and passionate about what he believes in, so it would add that layer, I think.

Does that ever make your life harder on the institutional side? Is it difficult for you when you have to project confidence to institutions, and, with respect, Jake is doing content that might seem a bit down or distracted or whatever that might be?

Yeah.

It’s clearly polarizing, but it’s very obvious, right? It’s a double-edged sword, right? Jake has such a big persona and character that one can’t just be dismissive on first glance. But I’m okay with that because, at the end of the day, we’re in the money-making business, and our track record makes money.

If it’s like, “Hey, LPs don’t understand the marketing and the attention gathering,” it’s like, “Okay, we’ll make ourselves and other people who are a little bit smarter than you guys more money.” So I think it’s like, you either lean into the brashness or the aggressiveness, or you try to hide it. Every great story, every great founder, every great business is like, you lean into strength. You want to be the best in the world, and I think we have a chance to be the best in the world in our exact style of investing and company formation.

Is all publicity good publicity? It’s the age-old saying. I’m never sure.

Yeah, it’s a very interesting question. There are a couple of things.

Don’t mention the island.

Yeah. No, that’s what I was going to say. It’s like, yo—

I should.

I was like, “Is Epstein’s publicity good?” No. Not all of it is good. It’s a bad saying.

Do you regret saying that you were uncancellable?

No. No, not at all, because I’ve never done anything that is bad, actually. I’ve been a dumb, arrogant kid. I’ve filmed videos or things around fire. Like, okay, cool. If everyone’s life was on camera from the time they were 14 years old, if we put a camera on you 24/7 through your college years, what were you doing at that frat party? That’s probably much worse than me lighting a pool on fire in Los Angeles.

So that’s the thing: I’m uncancellable because no one will ever find or see anything about me that is actually bad. It’s all just fake hate.

3. The New VC Advantage

We were talking about the business empire at the start. If we filter that down into being the best investor you can be, the immediate thought I had was, why does venture make sense? Reports around the latest fight say you make $70 to $100 million, OpenAI says. Why does it make sense to do a $30 million fund?

Yeah, I think if the $30 million fund was the end goal, it would be like, no. But we want to run $10 billion, $20 billion at some point and look up to people like Josh Kushner at Thrive, who started with, I think it was $5 million. So you have to start somewhere.

Obviously, I made a shit ton of money from the past fights as my career went on, but my first fight against Deji, a local here, I guess—

Ah.

—in London, I think we made about $1 million. So you have to start somewhere to be able to make it big.

When you think about the pillars of venture—how it’s done—there’s finding, there’s picking, there’s winning, and there’s helping. Now, I may be being assumptive here and rude, but I would assume that Jake is the master of winning and helping on distribution, and then you are the finder and the picker. Is that correct?

Yeah, and I think people underestimate Jake’s reps and what he sees, right? Even just describing the nuances of 6.9 seconds on a product feature, in some sense, he was an early adopter of all the social platforms as a creator. So I think that same skill set in terms of knowing what is coming around the corner and understanding consumer sentiment is essentially the same instinct as us VCs being like, “Hey, this guy’s a winner,” or, “This girl’s a winner, and their product and their vision, their roadmap makes a lot of sense.”

So I think the picking side—I don’t think we should underestimate Jake’s taste there. And I would argue that with AI making traditional smart-people stuff like coding and financial analysis just metered intelligence, having taste and having that cultural vibe is more important. I think that’s one of your big edges as an investor. I think you’re just cooler, more with it, and vibe with the next generation of founders much better than a boomer VC.

And I think you deserve success on the platform and in your funds. I think that’s the challenge, or the gauntlet, that we’re excited to fight with. I just saw that Bill Gurley was tweeting that paid marketing is the worst form of marketing, and I’m just like, hey, Uber—he’s most well known for kicking Travis out of Uber—and Uber burned tens of billions of dollars on straight-up marketing and just got to profitability, showing a quarter of net income positive 14 or 15 years in.

So my sense is that the software and the classic smart-people stuff gets commoditized, and the attention, the taste, and the culture side gets more and more important. So I think the world goes in our favor versus away.

Keith Rabois from Khosla and previously Founders Fund said that it’s really important to know what we sell as investors—what our product is—and I quite like that framing. When you think of the product that you sell founders, do you sell founders distribution? And how do you think about keeping the brand and the profile pure and not being, like, Better partnership and Sips Mugs and all the other companies—Oats Overnight, I did my work—that you partner with?

I think to each their own. We’re not plugging, saying, “Yo, we are going to give you distribution,” in companies where we don’t think we’re going to do that.

So you’re super upfront, like, “Hey, we’re not going to be distributing you on our platforms, but we’d love to partner with you.”

Yeah, and I think there are tons of other things to provide in terms of knowing culture and marketing, and just information in general. “Hey, you should do this. You should link with this person. This would be a good access point.”

There’s a religion app that we’re investors in. It’s like, “Okay, do you want to link with Trump’s pastor? I have his phone number.” Things like that.

That is the most random network intro I’ve ever had.

It is, but it’s like—

Trump’s pastor.

It’s like—

Yeah, sure. Nice to meet you.

It’s like, yo, we can provide value in tons of different ways, and I think each company is a different conversation.

What do the so-called “best VCs” even do? A lot of it is those introductions to revenue sources. We are a phone call away from literally any executive, any billionaire in the world. 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 super high.

We can compete with the guys who’ve been doing this for 30 or 40 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.”

I’d have a sniper-shot late-stage strategy if I was you. Have 10 of the best companies that we all agree on at late stage and just aggressively go after them. I know you’re invested in Ramp, for one of them. I think you’re in Anduril. And I’d just leverage the shit out of the personal brands and put $10 million, $20 million, $30 million to work.

I think that’s actually the correct way to think about it.

Yeah.

I think, at late stage, we have an unfair access advantage, and I think our actual value add is very valuable, too. Because at that growth stage, they’re looking at IPOs, and they’re looking at mass-media branding. And if you again look at track record, you can spend millions of dollars on some marketing VP or some CMO or some agency. Literally, Jake has driven probably billions of dollars of enterprise value and impressions in terms of new media.

And in some sense, I see what Mark and Ben are doing with their podcast media company—

True.

—their media company is essentially—one thought I had was: Can VCs become influencers faster than native influencers like Jake and Logan can become VCs? That’s kind of the battle. Benchmark acquired Jack Altman’s podcast. A16Z has a great media platform.

That again goes back to one of our founding principles, which is attention is more valuable than capital.

Okay, so when we think about that, we have early, then late stage. And then we have incubations as well, because you do Better as well.

Yeah.

Okay, so we want to start companies as part of it.

Yeah. Not too many, obviously; it takes a ton of work. But we incubated Better and W., and then my brother’s working on something now. Obviously, he built Prime as well.

Yeah.

So that’s a part of the strategy, coming in with ownership, but also just seeing a gap in the market. With Betr, it was all these sports gaming companies paying hundreds and hundreds and billions of dollars in marketing, and seeing that their ads were terrible and their app was clunky—it didn’t make sense.

I was like, “Yo, I could build a better app and promote it better and have better content,” and that’s why we created Better. So Better, Better, Better.

What deal are you not in that you would most like to be in?

I want to do more—I think we want to do a little bit more in Europe.

So I think Helsing is cool. With geopolitics, I think there needs to be a European Neo Prime for defense.

I agree.

We're chatting with Maddy over at Eleven Labs. I think they're doing great stuff.

Maddy's amazing.

But going to your point, I think with the power law—the winners are just super big—it makes sense to try to pick the number ones and maybe the number twos in every single category.

How much time can you realistically spend on venture?

I spend a lot of time on it. I think people don't realize 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, et cetera. I'm very, very involved, flying to San Francisco multiple times a year, meeting people on the ground, advising the companies that we're a part of, meeting with our different companies, et cetera.

I'm very passionate about it because I like it. Some of the other things that I do, I don't spend as much time in the weeds, but this is something I've always loved since I was 17 or 18 years old. Seeing the Ubers, the Twitters of the world, and Postmates when I was that young made an impression on me, and I've always loved it since then.

One thing I find hard is when we sell brand and we sell media, which is in some ways what we sell as our differentiator. One challenging element is that I feel relevance is this constant fight. You constantly are on a treadmill. Jack Altman's going to Betr. And Jack's got a fucking podcast, and so does Sequoia. I mean, every fund has a podcast. Then you have net-new people. I sometimes feel like Madonna, and there's fucking Dua Lipa at the party. Okay?

Yeah. No.

I bet you kindly said I look 36. Thanks, Jake.

No, no.

As a proud 28-year-old, I sit here. That treadmill for relevance is hard. Do you find that treadmill for relevance hard?

I don't, because I've broken through escape velocity. Just me being me now keeps me there.

Yeah.

I have a counterpart, my brother. We're the testosterone Kardashians, right? If I'm not doing something in the media, he's literally at NFL flag football, beefing with Tom Brady—the most talked-about thing in sports for the whole week.

We go back and forth, and we've built this ecosystem. We're differentiated and in the right markets—in sports, in content, on YouTube, Instagram, and TikTok—and we've been at the forefront of it since the foundation. I'm in a different league, but I think for other creators and influencers, it's a dying market for sure. It's very hard for people to stay in the know.

We're seeing more and more creators and influencers move into investing. What would you say to them, knowing what you know now?

It's a very tough game, and if you actually aren't good at it or know how to do it, then maybe don't just try to do it.

Mm-hmm.

It's almost second nature to me because I have vision and can see where things are heading. I'm ahead of culture and these things. We can see where things are going, and I think it is an actual talent and skill set to be in the right rooms, know who to talk to, know where to spend time, and know how to get what you want. I would say a lot of people can't do that necessarily.

What do you see now that other people don't see about culture, about taste?

That's like asking a karate master to show you all of his moves.

Welcome to the show.

It's almost instinctual.

Around the founder or the market?

Both, and culture, content. I think it's just a feeling, right? How do I know what video to make? It's just—

What's your hit rate on videos?

Pretty good. Me and my number-one content guy, before we post a video, predict how many views it's going to get. It's pretty much accurate 85% of the time.

Really?

Yeah.

Wow.

We'll say, “This is going to get 8.5 million,” or, “This is going to get 30. This one's going to get 40.” I don't know. It's just second nature in a sense.

An example is boxing, where I saw myself becoming the greatest celebrity influencer boxer, to the point where I wanted to become world champion, because I knew that boxing was going to have a revival, in part because of me. I saw the attention, the views, how much people liked it, the drama, and the money that was in it. I made the point to become the best one in it.

Then I excelled out of the group of just being an influencer boxer and went into, “Actually, this kid can become world champion.” I saw where everything was going and that it was going to have a revival and be at the forefront of things like Netflix, with the ability to make hundreds of millions of dollars from it before everyone else. There was a reason why all the other influencers fell behind.

Do you ever do or say shit and then go, “Oh, shit. I met Anthony Joshua. He's a big fucking guy”? I do my push-ups. He's a big guy.

Yeah.

When you stand next to him, you're not actually like, “I shouldn't have done this one”?

Oh, no. I don't think so.

You're so cool. He's just like, “Nah, it was fine.”

No. Even someone literally came up to me this morning in the freaking spa area at the hotel and was like, “Mate, that was amazing. It was crazy that you did that, but you left with your stock higher.”

For me, it was a win-win-win across the board fighting him, and I knew that going into it. I knew that I could actually hang in there with him, and the world would be shocked by my heart and skill set. Even if he were to knock me out or knock me down, I would just keep getting back up. I think the fight actually humanized me a bit, and people got to see a different side of me.

It's funny, Rahul said, “He's really dialed in that it doesn't matter if I win or lose. Attention makes me money. Boxing business.”

Yeah.

You stand by that?

Yeah, 100%. It's all math, right? I was more nervous to fight Gervonta Davis. If you lose to a tiny person, people would be like, “Oh, you suck.” So it's actually better to lose to a giant.

4. AI Changes Entertainment

When we think about culture, and you mentioned AI there in terms of the tooling, people describe sport as the most exciting asset class because it is defensible to AI. You're not going to see robots fighting in the same way that you'd expect to see humans fighting. Do you agree with that in terms of the rising stock price of sport in a world of AI?

Yeah. We've been on that side of the thinking, but I think things are going to get weird. I can't say for sure. That's an open question for me still.

What do you mean, things are going to get weird?

If I can put in a prompt to Cognition or any of these things and develop my own game that's personally tailored for me with a couple of clicks of a button, why would I watch the NBA when this game I made for myself has all my favorite things in it, friends and storytelling, and I made my own World of Warcraft or Minecraft in a day?

Will that suck away the entertainment? Or if I made my own whole Netflix movie exactly the way I wanted it, with certain shit in it, will that personalization take away from other forms of entertainment, which is sport? That's where things might get weird.

Are you excited for the future?

Yeah.

The answer has to be yes. I think you have to be.

Yeah.

I don't know. In all honesty, I'm quite scared. I'm quite scared because I think the majority of society will become unemployed. Most low-level work, I think, will be replaced. I think a lot of white-collar work will be replaced. I think we're facing this massive, depressed society of young people looking for meaning. We've got terrible, terrible eating disorders that are worse than ever. I'm nervous. And then, on top of that, we have world conflict like never before.

Yeah.

I always say this: 100 years ago, when they were coming up with the atom bomb and the nuke, people were like, “Oh, we're so scared. What's going to happen?” There's always fear in the development of human society and new technologies, and I'm sure people were scared of cars at some point. “What's this going to mean? It's going to take my job,” or, “I can go get another job.”

You can either look at it positively, but I believe—and obviously, it's going faster now and developing faster—I think humans will figure this shit out.

I think you have to look at the optimism and how you can be a beneficiary of this change. I think we each need to make a decision. Do you accelerate and drive faster into it and have a chance to take the steering wheel, or do you sit back, be scared, and crash into the wall?

Well, we're in Europe, so we'll sit back and be scared.

You guys are gonna crash into the wall?

Yeah, we’ll sit back.

Oh, yeah.

If that’s an option, we’ll take that one.

No, I want to take a harder stance. I feel like Europe is the sick man of the world right now. I feel like Europe could have some of the foundational civilization of Western culture that came out of here—London, England, right? And it feels like they’re not seizing the opportunity to lead, to create the future.

Humanity is driven by people that seize the opportunity, and I think you can decide: are we going to be passive onlookers of change, or are we going to be driving that change?

Take a harder stance. Come on.

5. The Drive Behind Money

What opportunity did you not seize that you wish you had seized?

Should I have just been in the Valley founding some company and being more involved in tech? I don’t know. I don’t have any regrets or anything like that.

I do like the Drake line where he’s like, “If we hadn’t made it here, we would be out in Silicon trying to get our billions on.” I always relate to that. I think it’s a good line.

Does money make you happy?

Does money make you happy? Money buys freedom, and I think freedom makes people happy. The famous saying, “More money, more problems,” is way too true. I think it’s a double-edged sword, for sure.

There’s a lot more to manage and a lot more stress, but then there’s also a lot more freedom. If you want to survive, it’s no different from food. Mom was a nurse and Dad was a roofer. We were fine, but we weren’t around anything like that.

Where’d you get your animalistic drive from?

I remember a specific moment when my parents were getting divorced, and my dad had to pay a lot of alimony. He was crying. It was one of the only times I’ve ever seen him cry, because he had to sell everything he loved to be able to afford to live.

I thought to myself, “I never want to be this crying father who isn’t able to afford much and is telling his kids, ‘We have to move to a different house,’” and selling everything that he loved. I remember he had to fucking sell his snowboard, his little shitty snowboard, just for $150 and stuff like that.

Now I’m blessed to be able to snowboard. I think of small things like that, and that moment definitely stuck out to me as a reminder: “I don’t want to be in that position, so I need to figure out money.”

We were chatting before, and I told my girlfriend about having you on the show. I think there’s a lot that the world doesn’t know about Jake, but they think they know from the public persona. You obviously work with him on a daily basis. What does the world not know that you know from the unique perspective that you have?

Jake, I think, is fundamentally a very kind, generous human. A lot of the philanthropy, supporting young up-and-comers, and anecdotes of friends who are suicidal coming to Jake for help—Jake just spending his time and money to take care of people—I think that’s undertold.

Maybe that’s a fine way to be about it. I don’t think Jake is doing it for PR. I think he’s genuinely a very kind, generous human being, which may be an alternative to the “I’m a boxer beating and talking shit to Mike Tyson” type of character that he projects.

Are you ever just sitting there like, “Oh, no, no. Be nice. Don’t say that to Mike”?

No. I think—well, one, I’m fucking in it.

We’re selling fights, dog.

I’m fucking in it. Oh, yeah. We’re just in it, so I’m on the fucking roller coaster.

Geoff’s like, “Yeah.”

“Fuck you, Mike.”

Yeah, I’m laughing.

No, no, no, but I think part of why we relate is that I have a troll tendency myself. I kind of like seeing the absurdity or the chaos of just seeing funny things happen in the world. There’s an amusing part of just seeing, “This is interesting. I get to perceive an interesting experience. I want to see more interesting stuff.”

If Jake is out there making interesting things happen in the world, that’s really funny to me on a personal level. Then, maybe the second point in terms of working closely with him is that I’m very impressed with the endurance and the context-switching ability.

We got to spend about 3 hours with the president a couple of weeks ago. Maybe not to make a direct comparison, but I was just very impressed with the president being on and context-switching really hard. He was remembering people’s faces, having good conversations, going to a rally, dancing, going on a podcast, doing a TikTok dance—just boom, boom, boom, boom, boom, switching and being in flow constantly.

I think that’s one thing where I see some parallel. I think Jake’s raw energy output is very, very high. I can speak to that as someone who was top of my class at Stanford, graduated in computer science with honors and distinction, and had a perfect SAT score. I’ve seen the caliber of “smart people,” and I think Jake’s endurance and energy are very, very high.

Then I think the other interesting nuance is that you can switch from being a celebrity, getting paparazzi when we’re out in L.A., to talking shit as a professional athlete—but actually having to train twice a day, 8 hours a day, and do the recovery. Then he jumps on business calls with literally the most famous CEOs that have been on your show, right?

Mm.

Advising them on their marketing strategies.

Sitting down with Sam.

Yes. I would say Sam is great. We love Sam. But I think that context-switching is impressive, because people just see snapshots of Jake. You see the full 360, and it’s like, “Man, cool.” I’m inspired by the level of context-switching and the flow to be able to move with all these different circles.

Yeah, no, thank you for the nice words. A lot of people don’t know shit about me. Even if they’ve watched everything or know everything, they still haven’t met me or spent time with me.

I think the number one thing that people say to me after meeting me for the first time is, “You’re a lot different than I expected.” I’m like, “Oh, so you thought I was a dickhead and a fucking retard? I don’t know. My bad, bro.” Cool.

6. Jake Paul For President

You mentioned getting to spend a couple of hours with the president. This was from friends of yours, not from me, so I’m not stoking any flames here. They are. Would you like to run for office or be involved in politics a lot more?

I wouldn’t like to, but I feel like it could be needed at some point. I’ve always said it. Geoffrey was actually the first one that mentioned it, about 6 years ago. He was like, “You’re gonna be the president, and you should run for president.” I was like—

Then it slowly became less of a joke, and other people actually started saying it to me. Then I just hang out with Trump, and I go on stage and give a speech off the top of my head. The first thing he says to me on stage when I turn around is, “Oh, you’re gonna run for office someday.”

Then we go backstage, and he’s like, “You should be the president,” and he endorses me. But to answer the question, I would only want to do it if I was, A, the best person for the job, and, B, if there were someone like Kamala Harris running who could potentially ruin the United States, and I would have to go and oppose them and save the country.

I don’t really want to sign up for that workload if I don’t have to, or if there’s someone better to do it. That’s how I feel about it.

I’m in the U.K., and I’m in London. Do you think Trump’s doing a good job? Iran is a challenging situation he’s got himself into. Deglobalization is a thing. Do you think he’s doing a good job?

Yes, I do. I think he is arguably one of the best presidents the United States has had in this term. There’s so much propaganda and so many things, but at the end of the day, he’s doing an incredible job.

There are always going to be criticisms. That’s why, again, I wouldn’t maybe want to sign up for the job, because no matter what you do, people are going to think they have a better answer, but we’re not in the rooms.

I believe in him as a person and as a human being. I’m not going to agree with everything he says or does. I think he just said, “I’m glad someone died on the internet.” I don’t agree with that, but overall, that’s my fucking president. I’m going to back him and support him and say that he’s doing a good job, 100%.

To me, I think he’s a very founder president. He actually makes bold decisions and tries to mold the future. But I think a lot of politicians are dictated by the flows of polling.

There’s a boldness and a leadership quality there that, in a very globally challenging, interesting time, makes you ask: do you want your leaders to have the boldness to take some risks, or do you want someone who’s more passive? From a venture side, you want to back founders and leaders who are able to take risks, right? Venture capital is a risk-taking business.

And I think there’s a very unique time in history: Are we going to have a multipolar world? Are we going to have U.S. hegemony continue for another, you know, century? I think it’s an open question, right? So then it’s like, which founder, which CEO do you want to be in that seat?

And I think you’d—again, from a venture capital hat on—you’d want to bet and put your money or your support to a bold, fearless leader.

Yeah, and you don’t want a career politician running a business. The first startup in America was America. It’s a fucking business, and so you don’t want a career politician running things. And I think it’s a very difficult position to be in, and I think no matter what you do as president, in any of the terms of any of the U.S. presidents, there’s always going to be the 50% to 60% of people that are like, “No, they suck. You suck. Da-da. Wait, they shouldn’t have done that. I have a better solution.”

Like, okay, buddy—then go fucking do it. Then become president and fucking fix it. So that’s my thing on it.

We released a show today with Matt Steckman, who’s the president and CBO of Anduril, and I asked him, “Do you feel any moral responsibility for how your products are used in conflict zones like Iran?” And he said, “No, we support democratically elected governments only. They are voted for by the people. What they choose, we support because they are democratically elected.” Do you agree with that as a stance? And if you think about Anthropic disagreeing with the Department of War and the Pentagon, do you think that’s wrong?

I think generally, where does that nexus of decision-making go, right? Do you want an unelected tech executive making that call or your democratically elected representative making that call? So I think from a fundamental culture and governance perspective, I would like to have the ego to be like, “Hey, I’m smarter than the president to make a game-time nuclear decision.” I feel like it’s 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, the democratically elected leader gets that call. To me, if you want to talk about taking those war-making decisions away from our government, okay, we could have some weird techno-fascist thing too. It’s a competition of ideas. Maybe that does happen in other countries and other regimes.

I think there’s a breed of arrogance around, “Hey, I think I’m just smarter than everybody else, so I get to make the call,” versus we’re in a society with a lot of constituents, and we vote for someone to make that call.

Yes, and I think human evolution is inevitable, so we’re going to these systems anyway. So if Anduril wasn’t going to build it, then okay, is someone who is evil, in the wrong hands in another country, going to build it, and then we don’t have it? So it’s needed, but I think also their mission is to make things safer for humans. That’s the autonomous side of it. And so if something needs to be done, then yeah, maybe fewer people will actually die because of their technology.

We mentioned Sam. We mentioned OpenAI. They—I don’t know how to say it—maybe opportunistically took advantage of it and swept in and provided a solution. You’re the master of content. You’re the master of storytelling. He then got heat for it. What would your advice be to him in terms of the messaging, the comms around the heat that he gets for jumping in?

Who gives a fuck? Seriously.

Seriously.

Yeah, who gives a fuck? Someone has to do it. I’d rather be in the rooms and a part of that thing than out of it. At the end of the day, I don’t have advice for him. He’s doing what he thinks is best in his decision-making. There are going to be repercussions, and I think we live in a society where no matter what someone does, they’re going to be hated or loved or hated or loved or hated or loved. So at the end of the day, you just have to make decisions and march on.

My sense is that tech leaders are becoming more and more like politicians because they have a bigger impact on culture, on society. Sam is in that position. He has a lot of information. He’s trying to make his best decision. My only secondary comment on it would be: show the human side of himself more, right? Because I think President Trump does a very good job of showing the raw human, and I think President Obama also had that similar quality on the other side of just showing a humanity to his decision-making.

7. The Price Of Relentless Drive

You said about showing your humanity. You got me in trouble this weekend because I said, again, to my girlfriend, “Jake Paul.” And honestly, I was expecting, I don’t know, a mixed response. And she’s like, “Oh my God. Did you see the video of him supporting his girlfriend at the Olympics? Oh my God. Would you do that for me? Would you have done that?” I was like, “No fucking way. I would be in the office. Are you kidding?” She’s like, “I knew it. I knew it. I knew it. See, why can’t you be more like him?” And I’m like, “For fuck’s sake, I’m joking.” I had to backtrack.

You know when you joke and it’s kind of not funny and you’re like, “Oh, fuck.” It is something I wanted to touch on, which is, I think relationships are really an art. What is your biggest advice on how to have an amazing relationship, but also crush it in—fuck, where do we start?—content, boxing, investing. What’s your advice?

I think in a relationship, it’s communication. You should always, in the relationship, try to be the 60%. If it’s 60/40, you and your partner should both be fighting to be the 60% and be there for each other and do more and love more and support more.

We should always be in a competition of who massaged who today. Who wrote the love letter? If my fiancée writes me a love letter, I’m like, “I’m going to write a better one back to you.” And then she’ll write another. Friendly competition in a relationship is good, and communication. Letting them see every side of you and fully who you are, I think that’s very important from early on. Tell them everything from day 1. I think that builds the trust and the foundation.

Is there a side of you that you’re most scared to share?

I’m not really afraid. I think I’ve talked a lot about my struggles more so in the past because I was struggling more when I was younger: childhood fame, living in Los Angeles, being surrounded by the wrong people.

But I do think dealing with mental health—my mind can become a crowded, dirty, and stressful place—and it’s a practice every day to manage it. And I think that’s where I’ve fallen in love with breathwork and meditation and spiritual journeys with ayahuasca, toad, mushrooms, all of these things, to learn more about myself and my mind. I would say mental health is always something that can fluctuate for me, and it’s something that personally I have to actively manage.

Do you know when it’s going down?

Yeah. I don’t know. It’s always different. That’s the weird part about it, I think. It’s not something you can fully grasp, and sometimes you don’t know until you’re in the thick of it and you’re like, “Oh, shit, I haven’t been taking care of myself.”

I’m an addict in every way. I don’t drink anymore because I did that. I’m very grateful because it makes me good at what I do. I’m so addicted to what I do. Are you happy or sad to be an addict?

Am I happy or sad to be an addict? I think being addicted to working and constantly doing something is part of who I am, but I do wish sometimes—I think about what it would be like to feel normal, where I don’t have to constantly be progressing and doing things.

But I don’t know. This is my body. This is my brain. This is my destiny. This is who I am. I’m very happy about that, but it is a double-edged sword sometimes. You think I’m addicted to work, is what you’re saying?

With the greatest of respect, I think it takes one to know one, and I think to compete—

No, yeah, yeah.

And I think to compete at the level that you do, as quickly as you do, in sport, and to fight Anthony Joshua and Mike Tyson with the little ramp time you have, you have to be, bluntly, psychopathic to get there that fast, in a brilliant way. I’m saying this in a good way.

To do the multitude of things that you do at the quality that you do, you have to be an addict. Again, I think we mischaracterize addiction as bad, and it’s not always bad.

Yeah.

I think every top athlete is an addict. You have to be to be the best.

I would agree 1,000%.

You have to be crazy.

I just think it’s interesting the way you describe it as an addiction. But you’re right, yeah, 100%.

8. The Fight For Greatness

When you think about your training, what was nuts about your training?

It’s just so intense and demanding.

What’s the most demanding?

I would say the track work. Sprints at the track are just brutal, and my coach just makes me run and run and run and run. My heart feels like it’s going to pound out of my chest, and your body has a central nervous system reaction because of how hard you’re pushing yourself. It’s very uncomfortable.

And then, just the day in and day out, you get lost in counting down the days until the fight.

The monotony of it, I think, can be very demanding and difficult and dry and boring and lonely. I mean, they say boxing is the loneliest sport for a reason. It's very true. You're in there by yourself.

Are you thinking when you're in it?

Yeah, but I guess it becomes a sort of flow state. It's like a super-high, fast-paced thinking match, and I think that's where I told people why I got good at boxing so fast: pattern recognition. I just think of it like recognizing patterns in the person that I'm fighting, then being able to expose it and do it at the right time. It's very calculated.

I see you dropped your hand in the first round after you threw this punch. I'm going to wait for you to do that again in 2 minutes and hit you with the right punch to counter that. Adding those things up, round by round, and remembering everything that they're doing and their habits and all of that is just a pattern-recognition game. That's why I think I got good at it, because my mind is better than probably every boxer's. If I had been doing it my whole life, I'd be the best boxer in the world, for sure.

Who have you not fought that you'd like to fight?

I think the only one that would ever come close to the Tyson numbers is me versus McGregor, which would be fun.

What number would you do it for?

McGregor? Good question.

150?

Yeah, I mean, it's at least worth that.

Yeah.

That's probably the minimum, but that's a good number.

When you get 150, how much do you actually take home after all the middle layer, mid-layer, mid-layer? It's like an Andrew SPV, you know, with a 30% carry and this and this and this. I take, you know—

Geoffrey Woo

Oh, Jake's a good businessman.

I'm talking about taking 10 shekels home with me on a camel.

I take home the most out of any boxer. I have the best setup in boxing because I'm my own promoter and I'm the one negotiating with the platforms. I don't have a lot of people involved. It's just me and Nakisa Bidarian on the boxing side of things.

And so you'll take home, like, 80%, versus Eddie Hearn, who will take home 50% normally.

No, I take home nearly 100%.

Well, that's pretty fucking great, isn't it?

Geoffrey Woo

That's smart business.

The percentage I give is to my own company.

I think you're missing a content thread. I think you should do something for the partnership: when you train for your next fight, you should bring Geoffrey to every session with you, and everything you do, Geoffrey's got to do.

Geoffrey Woo

I'm down, but I'll puke out pretty early.

No, it's not fun.

Geoffrey Woo

I've done some workouts with Jake.

Bro, yeah, it's not fun, and it just keeps on getting harder. That's what's also nice about boxing, but also not nice: it's a never-ending challenge, and it only gets harder as you continue to fight the best of the best.

Final one before we do a quick-fire: why does the money matter anymore? I didn't mean that badly, but, like, you said 150, but after 90 and all the other stuff, you're kind of flying private anyway. You've probably got a Gulfstream anyway. Why does it matter?

It doesn't in a lot of ways, but on the boxing side specifically, there are still things that I want to do in terms of goals, and they don't have to do with money. I want to become world champion—

You really do?

Yeah. But just for the story, just to inspire kids that I was the most hated, the most doubted, the biggest underdog, the YouTuber, the Disney kid.

And if I can become world champion, I think it would be the most inspiring sports story, or one of the most inspiring sports stories, in modern-day history. I could inspire kids that even if all the odds are stacked against you, look what I did, and you can do something.

Did you ever doubt the next transition? I've seen everyone always say, “Oh, the YouTuber. Oh, the Disney star.” Did you ever doubt internally in your head? I know we always tell the world, “No, no, no, it'll be great.”

No, for sure I did. YouTube—I was done with it. I didn't like it anymore and was running into a lot of issues with demonetization. It became a nightmare, and it was causing so many problems. I was in Los Angeles, and I didn't like what I was doing. I was like, “I need to do something else.”

First, I had to stop doing YouTube. I literally stopped filming. I noticed that a lot of times in life, you have to create space for something else to come in, and that's just the way life works. So I had to literally stop, and there was a space where I was trying to do things, maybe a little business over here or music. I was making songs.

Then I fell in love with boxing out of nowhere. But there was a time when I was like, “I don't know what the fuck's going on,” and that was when I was 21.

This really is the final one. Pretty quick-fire. Geoffrey, I know which way you want him to answer this one. You can be number 1 in the world at boxing, content creation, or investing.

Investing, actually, yeah.

Genuinely?

Yeah, 100%.

Why?

It's something that I can do forever, and it's really enjoyable. I really love being a part of the cutting-edge things in technology, advancing society and human evolution, and being able to meet with, talk to, and be friends with the smartest people in the world. I think it scratches an itch in my brain. I think I'm sapiosexual in that sense.

Geoffrey Woo

I actually had no idea what he would say, but I think even content, right? I think all of these things feed into each other.

Oh, they genuinely do. When he's crushing it at boxing, when he makes better content, the investing will be easier and easier.

Geoffrey Woo

100%, 100%. And I think it's okay to—just like founders are okay to say no to bad customers or not tackle certain markets, I think it's okay to be like, “Hey, LP, you get to allocate your money where you think you can maximize returns. If you think other people will do it better, great. Let's just see the numbers in a couple of years. Let's compete.”

I know you tweeted to one of my friends, Jason Lemkin. He's got—

Geoffrey Woo

Yeah, no, we said we're going to have more AUM, buddy.

We're coming for you, buddy.

You're fighting. We're going to do a quick-fire. Jake, you said something about making room for things in life. Would you like kids?

Yeah, but that's my number-one goal, honestly. That's what I think life's all about. I can't wait to be a father. They'll be my little best friends that I get to hang out with every day.

Geoffrey, what's the best-performing investment so far by multiple?

Geoffrey Woo

I think a couple from our fund. You mentioned Rahul and Aerodrome. That was a 10X in 18 months. Rahul had that stock in Flock Safety, which is crushing. Rahul's now the chief strategy officer there.

Polymarket is a good early one. But just our incubations, right? We're at the ground floor. Betr is definitely crushing it.

If you can crush Betr with high ownership, that's where you really make a lot of fucking money.

Yeah.

Geoffrey Woo

Yeah, no, it's exciting because I think with the expansion of the prediction markets and all of this stuff, we're excited about the opportunity ahead. But even on the personal side, I was an angel investor in Ramp. That's at a $50 million entry value, so that's, like, whatever, a 300X on the personal side.

Now, Jake, dinner's on him.

Yeah. Dude, that's so good. That's fucking A. Do you want to hear something funny? I met Eric Gleiman when he was doing Paribus, and then the night before he came out with Ramp, he was like, “Do you want to invest in my next thing?” And I was like, “Yeah, no. Paribus wasn't that big, but good luck.”

Yeah.

Geoffrey Woo

No, so Paribus—

Fuck.

Geoffrey Woo

—was my first angel investment ever.

No way.

Geoffrey Woo

I went to a high school summer camp at MIT. It was a selective summer camp called RSI with Kareem and Zach Frankel. They went to Harvard, I went to Stanford, so I was their Silicon Valley plug. I gave them the recommendation for Paribus to Y Combinator.

Oh, wow.

Geoffrey Woo

And I was like, “I don't really know what…” I think it was probably 24 at the time.

You could have basically been a co-founder of Ramp with that as the entry funnel into it.

Geoffrey Woo

I mean, I should've.

Geoffrey, you wouldn't be sitting here with me today. Fuck Jake Paul.

Jake, what's the most expensive item you've bought that you've never used?

The first thing that comes to mind is my Ferrari. It has 100 miles on it, and I think it came with 60.

How much was it?

$800,000.

You just don't like it?

No, I just have too many cars and other ones as well.

Yeah. So I'm building a racetrack so I can use these cars.

I've heard about this at the ranch.

Yeah.

Yeah.

That's—I'm like, “Bro, why do I have these cars if I can't drive them?” But I can't. It's not fun for me to drive them on the roads because I can't really rip it, so that's probably the thing that comes to mind.

Well, maybe we can cross 100 miles soon in that Ferrari.

Let's fucking go, bro. Let's race.

I need to get my—

Let's race.

You very kindly suggested driving on the track before, Geoffrey. I don't have my license.

Actually?

Geoffrey Woo

Well, it's a private track, so Jake can maybe bless you.

Oh, that's great.

Why don't you have your license?

Well, in London, dude, we don't need to drive, do we? We have Uber, and it's a city. You just never need to drive.

Geoffrey Woo

Autonomous cars soon, so no one needs to drive.

Geoffrey, what fund product do you not have today that you would most like to have? It could be a growth fund, a fund of funds, or a secondary fund. You name it.

Geoffrey Woo

No, I think, as you said before the show, we've just been scaling up AUM, so we're well within 9 digits now. I think Jake and I are very interested in the public markets.

How does that look in a product? Would you guys do a public fund?

Geoffrey Woo

I guess the way to think about it is that one of the edges Jake brings to the table is mass distribution, right? The public markets are just trillions of dollars of assets out there that we could prosecute against. So, again, it goes back to the start. If we don't set limiters in terms of our ambition and our skill set, you play the largest markets. Let's keep playing.

AX Capital, watch out. When I say high performance, Jake, who's the first person that comes to mind, and why?

I thought of Michael Phelps, I guess. I don't know.

I love Michael Phelps because he dispels the bullshit that you need to have a break, that you need to have a rest day.

Yeah, I just think of greatness at the highest level. It's measurable, and so I think that's why he comes to mind. You can't necessarily measure, “Okay, this is the greatest investor.” But in that time, who is the best right now? That's not super measurable, but that's, I think, why Michael Phelps came to mind.

Final one for both of you, and you have to give a different answer. If we sit down in 10 years' time, how would you define that it has been very successful as a venture fund, as an investing house?

Geoffrey Woo

You want to start, or I—

Yeah, I mean, we're making our LPs very wealthy, as well as ourselves, and being a part of shaping history and shaping the greatest companies in the world, making billions of dollars doing it for everyone and for ourselves.

Geoffrey Woo

Yeah, I think it's well said. My take on it would be focused on the fact that there are probably 100 humans over the next 10 years who will change history, and we want to be supporters, comrades in arms, in the trenches, building the civilization-changing companies and supporting the people who are at the ground floor doing it. So if we can be associated and friends with a large portion of those 100 people, that would be a huge honor.

Guys, listen, this was such a joy to do. Jake, I'm so glad that you'd sit down with a 36-year-old. I really appreciate it. Geoffrey went to university, and I'm 36, so it's a tough one.

Yeah, I'm going to regret that one for a long time.

Which means that we did pretty well. I mean, this guy went to Stanford? He's smart.

Yeah, no.

Jake.

He's great.

Jake, I'm going to regret the 36.

I'm going to regret saying that to you, but someone told me that once. They were like, “Oh, I think...” And this was when I was 24. They were like, “Oh, I think you're like 35.” And I was like, “That's fucked up.”