The Exchanges

Q We were talking about kind of the business empire at the start. If we filter that down into like being the best investor you can be, the immediate thought I had was why does venture make sense? If we can, you know, reports around the latest fight is you make 70 to a hundred million dollars, OpenAI says. Why does it make sense to do a thirty million dollar fund?

A Yeah, I think, um, if, 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, um, with, you know, I think it was four, five million dollars, and so, um, yeah, you have to start somewhere, and, and the, you know, obviously made a shit ton of money for The past fights, and as my career went, but my first fight against, uh, Deji, a local here, I guess, um, in London, like, I think we made, like, a million dollars. So, like, you have to start somewhere to, to be able to make it big.

AI assessment note: “you have to start somewhere to, to be able to make it big.”

Q We were talking about kind of the business empire at the start. If we filter that down into like being the best investor you can be, the immediate thought I had was why does venture make sense? If we can, you know, reports around the latest fight is you make 70 to a hundred million dollars, OpenAI says. Why does it make sense to do a thirty million dollar fund?

A Yeah, I think, um, if, 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, um, with, you know, I think it was four, five million dollars, and so, um, yeah, you have to start somewhere, and, and the, you know, obviously made a shit ton of money for The past fights, and as my career went, but my first fight against, uh, Deji, a local here, I guess, um, in London, like, I think we made, like, a million dollars. So, like, you have to start somewhere to, to be able to make it big.

AI assessment note: “if the 30 mil fund was, like, the end goal, it would be like, no”

Q What do you mean things are gonna get weird?

A You know, if you, if I can put into You know, 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 friends, and storytelling, and I made my own World of Warcraft or Minecraft in a day. Will that suck away the entertainment? Or I made my own whole Netflix movie the exact way I wanted it with certain shit in it. Will that personalization take away from other forms of entertainment, which is sport? Like, that's where, I mean, things might get weird.

AI assessment note: “that's where, I mean, things might get weird.”

Q What do you mean things are gonna get weird?

A You know, if you, if I can put into You know, 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 friends, and storytelling, and I made my own World of Warcraft or Minecraft in a day. Will that suck away the entertainment? Or I made my own whole Netflix movie the exact way I wanted it with certain shit in it. Will that personalization take away from other forms of entertainment, which is sport? Like, that's where, I mean, things might get weird.

AI assessment note: “that's where, I mean, things might get weird.”

Q Did you ever doubt the next transition? I've seen everyone always said, oh, the YouTuber, oh, the Disney star. Did you ever Down, internally in your head. I know we always tell the world, no, no, no, I'll be great.

A No, for sure I did. Um, you, YouTube, like, I was done with it. I didn't like it anymore, and Was running into a lot of issues just with, like, demonetization. It just became a nightmare, and it was causing so many problems, and I was in Los Angeles, and I didn't like what I was doing. I was like, I need to do something else. Um, but first I had to stop doing YouTube. I literally stopped filming, and I noticed a lot of times in life, you have to, like, create space for something else to come in. Um, and that's just the way life works, and so I had to literally stop, and there was, like, a space where I was trying to do things, and maybe a little business over here, uh, music, I was making songs, and then I, I, like, fell in love with boxing out of, out of nowhere, but there was a time where I was like, I don't know what the fuck's going on, and that was when I was, like, 21.

AI assessment note: “No, for sure I did. Um, you, YouTube, like, I was done with it.”

Q Jack's got a fucking podcast, and so does Sequoia. I mean, everyone has a podcast, and then you have net new people. I sometimes feel like Madonna, and there's fucking Dua Lipa at the party, okay? I bet you kindly said I look 36. Thanks, Jake. As a proud twenty-eight-year-old, I sit here and go, ah, That treadmill for relevance is hard. Do you find that treadmill for relevance hard?

A I don't because I've, like, broken through, like, escape velocity, and just me being me now, like, keeps me there, and I have a counterpart brother, like, we're, like, uh, the, the testosterone Kardashians, right? So, like, If I'm not doing something in the media, he's literally at the flag football NFL beefing with Tom Brady, the most, like, talked about thing in sports for the whole week, right? So, like, we go back and forth, and we've built this ecosystem, and we're just differentiated and in the right markets in sports, in content, and, you know, YouTube, Instagram, TikTok, and we've been at the forefront of it since Foundations, 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, it's very hard for people to stay in the know.

AI assessment note: “I don't because I've, like, broken through, like, escape velocity”

Q Jack's got a fucking podcast, and so does Sequoia. I mean, everyone has a podcast, and then you have net new people. I sometimes feel like Madonna, and there's fucking Dua Lipa at the party, okay? I bet you kindly said I look 36. Thanks, Jake. As a proud twenty-eight-year-old, I sit here and go, ah, That treadmill for relevance is hard. Do you find that treadmill for relevance hard?

A I don't because I've, like, broken through, like, escape velocity, and just me being me now, like, keeps me there, and I have a counterpart brother, like, we're, like, uh, the, the testosterone Kardashians, right? So, like, If I'm not doing something in the media, he's literally at the flag football NFL beefing with Tom Brady, the most, like, talked about thing in sports for the whole week, right? So, like, we go back and forth, and we've built this ecosystem, and we're just differentiated and in the right markets in sports, in content, and, you know, YouTube, Instagram, TikTok, and we've been at the forefront of it since Foundations, 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, it's very hard for people to stay in the know.

AI assessment note: “I don't because I've, like, broken through, like, escape velocity”

Q What did people not see work-wise that you wish they saw most?

A I don't care for them to see, but, um, they don't see the, 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. I think that stems from being a creator from vine where you had 6.9 seconds. People thought it was six, but it's actually 6.9. Um, And every second had, uh, and millisecond had to be measured out and calculated and changed and edited around, and so I think that, like, meticulous nature of what I do and create has, you know, obviously helped me since, since the beginning, um, and constant, almost like, It's almost like politics with my team where we're like arguing about every little second or song of the video or things like that, that actually matter.

AI assessment note: “every little millisecond is calculated and dialed and thought through”

Q Did you ever doubt the next transition? I've seen everyone always said, oh, the YouTuber, oh, the Disney star. Did you ever Down, internally in your head. I know we always tell the world, no, no, no, I'll be great.

A No, for sure I did. Um, you, YouTube, like, I was done with it. I didn't like it anymore, and Was running into a lot of issues just with, like, demonetization. It just became a nightmare, and it was causing so many problems, and I was in Los Angeles, and I didn't like what I was doing. I was like, I need to do something else. Um, but first I had to stop doing YouTube. I literally stopped filming, and I noticed a lot of times in life, you have to, like, create space for something else to come in. Um, and that's just the way life works, and so I had to literally stop, and there was, like, a space where I was trying to do things, and maybe a little business over here, uh, music, I was making songs, and then I, I, like, fell in love with boxing out of, out of nowhere, but there was a time where I was like, I don't know what the fuck's going on, and that was when I was, like, 21.

AI assessment note: “No, for sure I did.”

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

A Conflict, and struggle, and Um, love would be the top three answers for that. And, and I purposely invoke emotions in people as an entertainer. I want people to feel, like, fear or joy or hate or something. I don't care what they feel, but I know in certain videos what I'm gonna make them feel. Like, I posted an edit where, like, I acted like I was depressed and, like, Like, couldn't find meaning, meaning in my life, and so, like, it went super viral, because, like, people were like, yo, are you okay? People were texting me, like, yo, are you okay? Like, I saw your video, and I'm just like, no, I'm just, I'm just an entertainer. Like, I'm just making people think I'm depressed, like.

AI assessment note: “Conflict, and struggle, and Um, love would be the top three answers”

Q With, I, I'm in the UK, and I'm in London, um, do you think Trump's doing a good job? Iran is, is a challenging situation he's got himself into. De-globalization is a thing. Do you think he's doing a good job?

A Yes, I do. I, I think he, um, Is arguably one of the best presidents the United States has had in, in this term. There's so much propaganda and, and things, but at the end of the day, um, he's, he's doing an incredible job, and there's always gonna be criticisms. I mean, that's why, again, like, I wouldn't maybe wanna sign up for the job, because no matter what you do, people are gonna think they have a better answer. But we're not in the room. I believe in him as a person, and as a human being. And so, I'm not gonna maybe agree with everything he says or does, and, you know, like, I think he just, like, said, I'm glad someone died on the internet. Like, I don't agree with that, but overall, that's my fucking president. I'm gonna back him and support him and say that he's doing a good job, a hundred percent.

AI assessment note: “Yes, I do. I, I think he, um, Is arguably one of the best presidents”

Q What did people not see work-wise that you wish they saw most?

A I don't care for them to see, but, um, they don't see the, 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. I think that stems from being a creator from vine where you had 6.9 seconds. People thought it was six, but it's actually 6.9. Um, And every second had, uh, and millisecond had to be measured out and calculated and changed and edited around, and so I think that, like, meticulous nature of what I do and create has, you know, obviously helped me since, since the beginning, um, and constant, almost like, It's almost like politics with my team where we're like arguing about every little second or song of the video or things like that, that actually matter.

AI assessment note: “they don't see the, there's like so much genius in every .12”

Q How much time can you realistically spend on Venture?

A I mean, I spend a lot of time on it. I think, uh, 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, et cetera. So, Um, very, very involved, and flying to SF multiple times a year, meeting on the ground floor with people, advising the companies that were a part of, meeting with our, you know, different companies, etc. So, very passionate about it, and I, and it's because I like it. I would say I, in, in a, some of the other things that I do, I don't, Um, spend as much time, like, in the weeds, but this is, like, something I've always loved since I was 1718 years old, and seeing, you know, in SF, the Ubers, and the Twitters of the world, and Postmates, and getting to see these companies when I was that young, like, made an impression on me, and I've always loved it since then.

AI assessment note: “I mean, I spend a lot of time on it.”

Q How much time can you realistically spend on Venture?

A I mean, I spend a lot of time on it. I think, uh, 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, et cetera. So, Um, very, very involved, and flying to SF multiple times a year, meeting on the ground floor with people, advising the companies that were a part of, meeting with our, you know, different companies, etc. So, very passionate about it, and I, and it's because I like it. I would say I, in, in a, some of the other things that I do, I don't, Um, spend as much time, like, in the weeds, but this is, like, something I've always loved since I was 1718 years old, and seeing, you know, in SF, the Ubers, and the Twitters of the world, and Postmates, and getting to see these companies when I was that young, like, made an impression on me, and I've always loved it since then.

AI assessment note: “I spend a lot of time on it. I think, uh, people don't realize”

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

A Conflict, and struggle, and Um, love would be the top three answers for that. And, and I purposely invoke emotions in people as an entertainer. I want people to feel, like, fear or joy or hate or something. I don't care what they feel, but I know in certain videos what I'm gonna make them feel. Like, I posted an edit where, like, I acted like I was depressed and, like, Like, couldn't find meaning, meaning in my life, and so, like, it went super viral, because, like, people were like, yo, are you okay? People were texting me, like, yo, are you okay? Like, I saw your video, and I'm just like, no, I'm just, I'm just an entertainer. Like, I'm just making people think I'm depressed, like.

AI assessment note: “Conflict, and struggle, and Um, love would be the top three answers for that.”

Q With, I, I'm in the UK, and I'm in London, um, do you think Trump's doing a good job? Iran is, is a challenging situation he's got himself into. De-globalization is a thing. Do you think he's doing a good job?

A Yes, I do. I, I think he, um, Is arguably one of the best presidents the United States has had in, in this term. There's so much propaganda and, and things, but at the end of the day, um, he's, he's doing an incredible job, and there's always gonna be criticisms. I mean, that's why, again, like, I wouldn't maybe wanna sign up for the job, because no matter what you do, people are gonna think they have a better answer. But we're not in the room. I believe in him as a person, and as a human being. And so, I'm not gonna maybe agree with everything he says or does, and, you know, like, I think he just, like, said, I'm glad someone died on the internet. Like, I don't agree with that, but overall, that's my fucking president. I'm gonna back him and support him and say that he's doing a good job, a hundred percent.

AI assessment note: “Yes, I do. I, I think he, um, Is arguably one of the best”

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

A 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 culture and these things, you know, since I was a kid, and so we can see where things are going, and I think it is an actual talent and, and skill set to be in the right room, to know who to talk to, to know where to spend time, um, and know how to get what you want, and so, I would say a lot of people, like, can't do that necessarily.

AI assessment note: “maybe don't just, like, try to do it”

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

A 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 culture and these things, you know, since I was a kid, and so we can see where things are going, and I think it is an actual talent and, and skill set to be in the right room, to know who to talk to, to know where to spend time, um, and know how to get what you want, and so, I would say a lot of people, like, can't do that necessarily.

AI assessment note: “It's a very tough game, and if you like actually aren't good at it”