The Exchanges

Q Can I ask the question then of like, you know, ah, the sale, like acquisition, that are reported two hundred and fifty million dollars?

A So that was an investment, um, but yes, so we were, Basically, I don't know, a year and a half ago, I came to the conclusion the best outcome was we find someone who can come in, who can be the source of capital and control, and would also be able to get board control. And so we mutually agreed, listen, let's find someone who can come in, give them both of those things. I'll give up control of the team and, you know, no longer be the source of capital. They'll give up control of the board and finally align these two things that should have never been out of alignment in the first place. And it was great. Uh, we couldn't be happier than having, you know, Bob Iger and Willow Bay and, and making this investment they did at this stage in this valuation is, you know, it's exciting.

AI assessment note: “So that was an investment, um, but yes, so we were”

Q told me a story about you coming all the way on the train from UVA, I think it was, and how you went to this cafe in Harvard Square with him, and he wanted to know, specifically, a couple of questions, but he wanted to know, how do you remember that experience, and what were you thinking and feeling after that meeting with him in the cafe in Harvard Square?

A Oh yes, that was Cafe Algiers. I hope it's still there. I was elated. And I still have, I kept a journal from back then, so I, I, I know this pretty vividly because I wrote it all down after. And I was elated because this was the first person other than my parents who had given just total excitement in, in response to the pitch. I had a professor, Mark White at UVA, who was awesome, and he was very supportive, but he was a bit more measured because, you know, he's a, he's a professor. He's like, he's like, look, there, there's a lot to weigh here. My parents, to their credit, actually, my mom especially, all day long, you can do this. We believe in you. But PG was then This independent third party who was an expert, right? Having founded a successful startup before who said, actually, this is really exciting. I actually did not know who Paul Graham was, uh, before we heard him speak. I just knew that Steve was really a big fan of his. And, uh, I was just elated because, you know, I did a little research after and I was like, Oh, this guy clearly knows what he's talking about. And, and so I was, I was thrilled that someone who had no reason, you know, who is not My parent, uh, had no reason to just blindly support us. Not, I wouldn't say blindly supported us, but at least believed in what we were building. So it was, it was quite validating, quite exhilarating, and, uh, yeah, it…

AI assessment note: “I was elated because this was the first person other than my parents”

Q But I'd love to start today with how you made the move from incredibly successful founder to VC with Initialize. So what was that transition?

A Well, it all started with a suggestion from Paul Graham, which incidentally is also how I made the transition from clueless college student to founder. And he obviously suggested that Steve and I change our initial startup idea when we were applying to Y Combinator. What came out of that ended up being Reddit. And similarly, he had seen that Gary, Gary Tan, Harge Taggart, and I were independently good angel investors. And we were obviously very close to the YC network and we were participating a lot. I think at the time, Gary was a full-time partner. I might've been a part-time partner at the time, but we were very much in the YC ecosystem. And as angel investors, we were investing in companies and Paul had seen and heard that companies, founders really liked us. And he said, you know, you should do more of that. You should invest more money. And I told Paul, yeah, that'd be great. I just don't have the liquidity that you or some of the other senior, more senior partners at this firm have, right? A lot of the other partners were in their late forties and had had very, very successful careers and basically just had a lot more cash money. And he said, well, there's a workaround. You could just raise I thought, huh? I hadn't really thought of that. And so Gary and Harge and I sat down and said, okay, let's start a fund. Let's raise a little bit of money. We raised about seven. And…

AI assessment note: “he said, well, there's a workaround. You could just raise a fund.”

Q But I'd love to start today with how you made the move from incredibly successful founder to VC with Initialize. So what was that transition?

A Well, it all started with a suggestion from Paul Graham, which incidentally is also how I made the transition from clueless college student to founder. And he obviously suggested that Steve and I change our initial startup idea when we were applying to Y Combinator. What came out of that ended up being Reddit. And similarly, he had seen that Gary, Gary Tan, Harge Taggart, and I were independently good angel investors. And we were obviously very close to the YC network and we were participating a lot. I think at the time, Gary was a full-time partner. I might've been a part-time partner at the time, but we were very much in the YC ecosystem. And as angel investors, we were investing in companies and Paul had seen and heard that companies, founders really liked us. And he said, you know, you should do more of that. You should invest more money. And I told Paul, yeah, that'd be great. I just don't have the liquidity that you or some of the other senior, more senior partners at this firm have, right? A lot of the other partners were in their late forties and had had very, very successful careers and basically just had a lot more cash money. And he said, well, there's a workaround. You could just raise I thought, huh? I hadn't really thought of that. And so Gary and Harge and I sat down and said, okay, let's start a fund. Let's raise a little bit of money. We raised about seven. And…

AI assessment note: “Well, it all started with a suggestion from Paul Graham”

Q All right, let's do it. Okay, your favorite book, and why?

A You know, I read mostly nonfiction now, but one of my favorite books was Slaughterhouse-Five by Kurt Vonnegut. It is fascinating to me how insightful that man was about Life and how amazing he was at telling stories through some of the weirdest narratives imaginable. And I also, I did my senior thesis in history on the bombing of Dresden, which is one of the settings for that book. And actually Kurt was a POW in Dresden during the bombing. So he has a pretty unique perspective on it all, but I just really, I love his storytelling. He is, or was rather a A really, really talented writer, and very, very insightful. And, and one of my favorite Vonnegut quotes, which is, he's talking to a bunch of children, and it's, goddammit, you've got to be kind. It is, it was the lessons from life. It was like, hello babies, welcome to earth. It's hot in the summer and cold in the winter. It's round and wet and crowded. On the outside, babies, you've got a hundred years here. There's only one rule that I know of, babies. Goddammit, you've got to be kind. And, I feel like there are plenty of faiths, there are plenty of adages all about kindness, this is not a new thing, but he just does, he conveys it in such a delightful, delightful way. That's not, it's not from Slaughterhouse-Five, but it's still a Vonnegut quote, so I, I get credit.

AI assessment note: “one of my favorite books was Slaughterhouse-Five by Kurt Vonnegut.”

Q What age do you most want to capture fans?

A Ah, yes. The youth. The youth. Like, seven, eight, nine, 10, like, as kids are really starting to form opinions about their favorite players and their favorite sports, that's when we want them To, to start dreaming of our players, and either idolizing them, putting their poster on the wall, and it's starting now, even Natalie has this great thing, she said her son has a poster of Messi, and a poster of Alex Morgan on her wall. Now Alex is not on our team, so that's fine, he's, he's allowed to like who he really likes, but I think we're entering an era now where young boys will, it'll be just as easy for them to idolize male athletes as female athletes, and I think that, I mean, That's a great thing. Uh, and it's, it's just starting to turn the corner here, and it'll be a wild new generation.

AI assessment note: “Like, seven, eight, nine, 10, like, as kids are really starting to form opinions”

Q I love that. I'm super passionate about kind of bringing these people to the fore. And then final one, Alexis, talk to me. What's the most recent publicly announced investment? And why did you say yes and get so excited?

A Well, the first one out of seven, seven, six was Dispo. And I mean, I said yes, because this was a company that already had a A few million installs had ridiculously high engagement numbers, which are all good signs for an early stage, uh, consumer social app. But more importantly, was building something that felt like a much healthier photo sharing application. And it's simple, right? The idea is you take the photo, you can't look at it till the next morning, but what this is doing for a whole generation, and, and believe me, like we have a Very happy to hear we made this investment because they and all their friends were already users in Dispo. It means a generation is, is spending time together, obviously safely. They're in their pod, and they're taking photos, you know, rightly so, to remember those good memories, but they're not trapped in their phones all night, editing, photoshopping, coming up with the perfect caption. They're actually going back to living in the moment, and it's such a simple bit of functionality, but just like the first version of Instagram was really simple functionality, Dispo has cracked what A generation is looking for as a kind of anti Instagram or anti photo sharing device, because, uh, there's nothing wrong with saving those memories. But like I said, they've watched what it's created in the toxicity and the bullying, and even just the fact tha…

AI assessment note: “the first one out of seven, seven, six was Dispo. And I mean, I said yes”

Q to move to seven, seven, six, because when on your side, it says about kind of making great advancements, and then also not repeating great mistakes. And so when we put on like the builder hat, you were seven, seven, six, and with the element of you said there being reflective, I'm really interested. What worked for you with initialized that you've taken with you in forming seven, seven, six?

A One of the reasons why Gary and I did, did such great work together is that we both really believed that doing this job well is about service. I think most VCs don't realize that they're in the net Promoter score business. And that is really what matters most. And we're seeing it start to manifest now more and more, you know, individuals are starting to supersede the brands of firms in a way that we're seeing across industries, right? Substack. I've got a friend of mine who, who left her job at fortune, you know, a great publication to start a newsletter and she's already making more money. She's already got more, I mean, she's got more control over what she writes. Like we're seeing this happen across every industry and venture is not going to be immune to And so what that means is one's reputation really, really matters. And, and one of the things we got right early with initialized was that supporting our founders really was the best thing to do for the business. It goes without saying you've got to pick well, like for sure, but that's just table stakes. And in this new world, it's so, so, so important to actually be building an organization that can really support founders because at the end of the day, they're the ones who are going to keep the brand alive. They're the ones who are going to keep the deal flow coming. And they're the ones who also will have even more succes…

AI assessment note: “one of the things we got right early with initialized was that supporting our founders”

Q What would you most like to change about the world of venture, Alexis?

A I would like to see more people doing this job who don't look like you and me, Harry, because I want to make more money because that's actually how we're going to have better things. Like, and this isn't like a social justice argument. This is a, we have 24 hours in the day, Harry. That's all we have. And we have our end years of life and life experiences. And that always is going to put a ceiling on the companies that we can back and the founders, specifically the founders we can back. And so every time we do that as world-class best investors, you and I are missing out on potential, not just in our portfolio, we're missing out on potential like apps that we could be using businesses that we could be patronizing. There is, that is the thing that frustrates me the most because it's It's not a social justice issue. It's a capitalism issue. Like, there is a cost to the free market if we aren't actually getting the best ideas surfaced and funded and built. And that, that necessarily involves a greater number of founders and a greater range of markets, et cetera.

AI assessment note: “I would like to see more people doing this job who don't look like you and me”

Q How would you summarize your brand today? People often call me the Charlie and the chocolate factory adventure. I'm not quite sure that's the brand I'm going for, but, uh, would you summarize yours?

A I don't know. I would love to know. I mean, when I see, okay, the buckets of things that I hear, I should survey people. I mean, the buckets of things that I hear are, uh, Serena Williams, husband, Which is great. I'm very happy to take that. I would much rather be known as Serena Williams' husband than, like, co-founder of Reddit. I'd also love to be known as Olympia's dad, but she's still three, so there's not a lot. She's still, she's got a lot of work to do. But I hope my reputation is one where I've not always made the right decisions, but I'm trying really hard to be on the right side of history across a lot of issues. And, you know, it's funny. It's almost Quaint talking about things like open internet, net neutrality, which were big causes that I championed five, six, seven, eight, nine years ago. But I hope the brand is about doing the right thing and, and hopefully one that sets a higher standard in an industry that has pretty low expectations. I mean, there are memes built around venture being an industry of just sort of lean back, lazy, soulless finance people. And there is some truth to that. I do think that is rapidly changing. And, uh, and I hope the reputation that I have with the founders is one that they know two in the morning, they can text that they know whether it's a small problem or a huge one that we can be the first call and that we can actually do som…

AI assessment note: “I hope the brand is about doing the right thing and, and hopefully”

Q proceeds from Reddit, and it's something that I think about a lot kind of correlated to happiness, and it's like, you know, I always told myself that with a certain amount of money, I would be happy, and then, you know, as time, that kind of amount has scaled, But I'm never happy with each incremental milestone. I'm really interested. How do you think about your relationship to money today?

A Well, look, there's been plenty of great studies that show the drop off of like marginal wealth over a certain point, like additional wealth over a certain point doesn't bring the same kind of happiness that it does earlier. And I think you're right. I mean, I felt, look, I felt the exact same way. That's why I was so excited when we got that offer. Like I could barely control myself when they said we'd like to spend ten million dollars to buy Reddit. I just, I had never even conceived of that. Kind of money before. And then it's, it's funny that keeping up with the Joneses mentality, especially in an industry like tech and seeing how much it's grown in the last decade or two. I've, I've watched people who have acquired tremendous wealth, certainly beyond what I have and, um, and still be among some of the most dissatisfied, unhappy people. I think all the cliches are true. The difference is about money, not buying happiness. And I think the biggest challenge is, I think there's absolutely truth to a kind of, um, There's sort of a floor. There's some level where once you no longer have to think about things in an existential way, like you're not worried about making that, that rent payment at the end of the month type of way, that is absolutely difference making. There's no doubt a huge difference there when it comes to happiness and whatnot. And I think that's one of the parts…

AI assessment note: “I felt the exact same way. That's why I was so excited when we got that offer.”

Q have to ask, there's been another big change in your life since we last spoke, and it's you becoming a father to Olympia, and it's such a monumental transition for anyone to make in terms of becoming a parent. How did becoming a father change your kind of operating, investing, and also you as a person, obviously, Alexis? I don't normally ask about you, but how did it change you?

A It has already made me a much, much more efficient manager and investor because when you have a child, you have to, like, I thought I was good at time management and organization. You have to be a ninja. You really, there's, there's no excuse. It forces you to up your game because you know how valuable that family time is and you know how bad you're going to feel if you squander it. And so when I'm with Olympia, I truly try hard to give her all of my attention. I put the phone away. I really, really try to lock in. And when I'm not, I really, really focus. I really, really lock in. I mean, I optimize to the point where I just reflect back every week and see where I spent my time because I keep track of it in software to know if I'm like misallocating, like I'm spending more time than I thought working with portfolio companies versus taking pitches versus working with my team. Like I, it has made me a thousand times better, um, around sort of self-improvement, whether it's my health or whether it's time management, it's made me much more effective in that way. And, uh, and yeah, I can't help but look through investments now through the lens of, does this get me excited when I have the dinner table convo? She's only three, so she doesn't care right now. But when I have the dinner table convo about what I did at work and what's going on and what things am I excited about us doing?…

AI assessment note: “It has already made me a much, much more efficient manager and investor”

Q Speaking of those types of deals, they're often sometimes quite out there on the kind of spectrum of kind of crazy and risky. When we were chatting before, you said there were kind of two types of deals in venture. Can you explain to me the two types of deals and how you've seen them play out in the past?

A Yeah. There's the like intelligence test type deals where, you know, it's a, it's a repeat founder, really strong, obvious market. Maybe they're just taking a second swing at At the thing they had done before. So you know, they're capable. You've worked with them before. Like it's, those are the kind of canonical, like hot type deal where you win because you get the call. Like you win because you won the deal, not because you necessarily identified something before other people did. And then there are other deals, which are the ones that really stir my cocoa, which are the ones where it's a super contentious type deal because the market they're going after the, you know, fill in the blank is just so nascent. Or so crazy that it may not work out at all, but if it does, the upside is massive. So Roe was an example of a company that like, and actually Z's talked about this, I think publicly there, there are a number of firms where like, that was a super contentious deal. And when it started, it was a pitch deck and some founders, and you had to believe in these founders and their ability to do more than just make like a shallow marketing company for ED meds. And if you spent any time with this team, Sort of like game recognized game. Like if you're a founder, I think it also just becomes a little easier because you can relate to another CEO who has this big vision who, you know, c…

AI assessment note: “There's the like intelligence test type deals... And then there are other deals”

Q How did you get into the sports ownership game?

A You know, it was one of the most contentious deals ever at Initialized, and this was, so, okay, well, it originally started with a tweet storm in 2019, March. I saw that Megan Rapinoe's team, she's an American footballer or soccer player, had just sold for like four million dollars, and I saw it in my feed, and I just thought, wait, that makes no sense. Like, a whole team is worth four million dollars. Like, If you're marketing Megan Rapinoe well alone, she should be worth that much a year in brand revenue. So something doesn't make sense. And I literally tweeted this all out stream of consciousness, and somewhere in the third or fourth tweet, I just said, you know what? I'm gonna buy a team in this league. I'd never heard of it before. It was called the NWSL. I was like, alright, fine. You know, the World Cup's coming up. This is 2019, right? American soccer is defined by women. And for non-American listeners, you have to understand, our men are terrible. All right. They've never won anything on a global stage. I love, I mean, USA all day, but.

AI assessment note: “it originally started with a tweet storm in 2019, March.”

Q How did you get into the sports ownership game?

A You know, it was one of the most contentious deals ever at Initialized, and this was, so, okay, well, it originally started with a tweet storm in 2019, March. I saw that Megan Rapinoe's team, she's an American footballer or soccer player, had just sold for like four million dollars, and I saw it in my feed, and I just thought, wait, that makes no sense. Like, a whole team is worth four million dollars. Like, If you're marketing Megan Rapinoe well alone, she should be worth that much a year in brand revenue. So something doesn't make sense. And I literally tweeted this all out stream of consciousness, and somewhere in the third or fourth tweet, I just said, you know what? I'm gonna buy a team in this league. I'd never heard of it before. It was called the NWSL. I was like, alright, fine. You know, the World Cup's coming up. This is 2019, right? American soccer is defined by women. And for non-American listeners, you have to understand, our men are terrible. All right. They've never won anything on a global stage. I love, I mean, USA all day, but.

AI assessment note: “it originally started with a tweet storm in 2019, March.”

Q What age do you most want to capture fans?

A Ah, yes. The youth. The youth. Like, seven, eight, nine, 10, like, as kids are really starting to form opinions about their favorite players and their favorite sports, that's when we want them To, to start dreaming of our players, and either idolizing them, putting their poster on the wall, and it's starting now, even Natalie has this great thing, she said her son has a poster of Messi, and a poster of Alex Morgan on her wall. Now Alex is not on our team, so that's fine, he's, he's allowed to like who he really likes, but I think we're entering an era now where young boys will, it'll be just as easy for them to idolize male athletes as female athletes, and I think that, I mean, That's a great thing. Uh, and it's, it's just starting to turn the corner here, and it'll be a wild new generation.

AI assessment note: “seven, eight, nine, 10, like, as kids are really starting to form opinions”

Q Where does that thirty-one million come from? I'm just so blown away by that number.

A The bulk of it's in brand deals, so sponsorships. Remember now, these things get renegotiated every few years, um, and so sometimes they're, it might be a four-year deal, two-year deal, three, et cetera, um, but there are lots of spots, uh, around the facility. I think this is another thing, this is actually a good lesson from esports, Where I was always enamored with, like, Hundred Thieves did such a good job building a brand around their players. FaZe Clan also did too. Where people would watch them playing Uno. Like, it, you, you, you have to always work backwards. So why, why? Best question ever. Why do people care? People care because they fall in love with these players. They want to see them all the time. Not just on the pitch, but also just in their lives and what they're doing. And so part of the job of a club is to then Tell the story of our players every minute they're not on the pitch. Because, one, that's, some of those are brandable opportunities, right? I can go to a sponsor, and believe me, the, the, the difference going to Canlion now, this is where every brand in the world comes to basically get drunk and, and then convince themselves where they're going to spend their money for the next year. And so I'd go, you know, in my capacity with Reddit for years and years and years trying to convince these brands, hey, please spend money on Reddit. This is the year, l…

AI assessment note: “The bulk of it's in brand deals, so sponsorships.”

Q Um, I, one more question before we do a quick fire, and it's just, You invested in MrBeat, kind of aligned in terms of media, next generation of entertainment. You first outside investor in MrBeat's Feastables?

A Yes. Pre-launch, and, and I just needed- So just talk to me, how did that come about? You know, I'd been chasing Jimmy for a while, so I seeded Patreon in 14, and over the years as Patreon started growing and defining this idea of membership and the creator economy, I'd, I'd introduce them to folks, Creators all the time, and they always said the one that they really want to get is Jimmy, and the thing that I learned was for Mr. Beast, it was never even on the table simply because one, he was so relentlessly focused on just creating these great videos, and two, he was already tracking so well that he didn't want any outsider to own the thing. He wanted to just have it all be under this empire, and he didn't quite know how he was going to do it, But then as soon as this idea popped up, I was like, literally, I don't need to know anything about what this business is. As long as you're making something and you believe in it, it's going to do well. And, and there were definitely some false starts, um, and learned a lot making, uh, candy bars, but seeing the growth has been phenomenal. I don't know if I'm a, some of this stuff's probably public. He's probably talked a little bit, but it has, you know, prime and feastables are the two examples. That's Jake, uh, no, Logan Paul, uh, his drink. Um, those are the two examples of what I think is, it's unprecedented in terms of, we're now …

AI assessment note: “Yes. Pre-launch, and, and I just needed-”

Q then I've got another question from Judith here, and she says, what are the biggest surprises about the move into VC? Obviously you moved from kind of a less institutionalized, almost angel fund to, to now with the larger funds and the most recent fund, which obviously is very much an institutional angel fund, not an angel fund, institutional fund. So what are the biggest surprises about making that move?

A The biggest surprises is actually, there is a really Really important value in process. Part of raising a fund of this size is that there are just different requirements placed upon you just, just in terms of just the rigor of managing the business. And the thing that's been really, really interesting, and I think really, really fruitful and helpful has been this new set of lenses through which we look when we talk about growing business, The business of it, the, the products behind it. You know, we are, we're all makers ourselves. Gary, in fact, wrote just about all of the modern code that powers Y Combinator. And that software does a lot for making our lives a lot easier. And so, you know, after we left Y Combinator and put attention to initialized, the thinking was, all right, well, what's the software we need to scale this business? And what we found is by putting a focus on that, We're discovering just actually how much of a difference, like how much of a beneficial, it seems sort of obvious because a lot of, you know, the companies, so many of the companies we invest in are disrupting businesses with file cabinets, as we like to say. So it seems obvious that we should want to do this for VC as well. But the first two funds were a lot smaller and, and we did them sort of in concert with being partners at Y Combinator. And so it wasn't necessary to have all this infrastruct…

AI assessment note: “The biggest surprises is actually, there is a really Really important value in process.”

Q but no, no, you're not an idiot because at the time it was like the unbundling of audio and the future Facebook. Dude, I remember when there was like a genuine playful, are we going to see the unbundling of Clubhouse? Into like sports radio. Yeah. Yeah, totally. I remember that completely. What is your biggest lational observation from seeing Serena in terms of the training, the dedication, the consistency?

A The weirdest dynamic that we have is I genuinely love every bit of what I do. My worst days, I really, I like, like we were saying before, like, I, I, I know how lucky I am to do something I love this much all the time. I could do it all the time. I literally could, and I love my family, but I could do this all the time. She did not love the process all the time, and she'd be the first to admit, like, I am doing this thing because I want to win. I do it for the trophy. I do it for the outcome, and obviously, look, being a professional athlete at that level is much harder than the work that we do, so I get that, like, it's just harder work as well, but the fact that she Put in that commitment so consistently since she was a kid is awe-inspiring, and, and I, and so then it just makes me even more motivated, even more incentivized, uh, but it is a weird dynamic because I, like, it's not like, and I, I think she's been pretty outspoken about this, like, this is, this was not something that she, I don't know, it was, it was a labor of love, but not in the way that we think about it. It was, it was a love for the outcome, And you just knew the process was the thing you just had to do. And it was the only way to get to that outcome, but you didn't like whistle on your way to work type of thing. And there are some days where I'm, I'm not whistling, but I'm like rocking out, uh, on the …

AI assessment note: “She did not love the process all the time... I do it for the trophy.”

Q Where does that thirty-one million come from? I'm just so blown away by that number.

A The bulk of it's in brand deals, so sponsorships. Remember now, these things get renegotiated every few years, um, and so sometimes they're, it might be a four-year deal, two-year deal, three, et cetera, um, but there are lots of spots, uh, around the facility. I think this is another thing, this is actually a good lesson from esports, Where I was always enamored with, like, Hundred Thieves did such a good job building a brand around their players. FaZe Clan also did too. Where people would watch them playing Uno. Like, it, you, you, you have to always work backwards. So why, why? Best question ever. Why do people care? People care because they fall in love with these players. They want to see them all the time. Not just on the pitch, but also just in their lives and what they're doing. And so part of the job of a club is to then Tell the story of our players every minute they're not on the pitch. Because, one, that's, some of those are brandable opportunities, right? I can go to a sponsor, and believe me, the, the, the difference going to Canlion now, this is where every brand in the world comes to basically get drunk and, and then convince themselves where they're going to spend their money for the next year. And so I'd go, you know, in my capacity with Reddit for years and years and years trying to convince these brands, hey, please spend money on Reddit. This is the year, l…

AI assessment note: “The bulk of it's in brand deals, so sponsorships.”

Q And how much did he sell it for?

A Six billion. Let me, let me double check that. But I, yeah, and again, one of the worst owners of all time. And what's crazy about that is I still want to watch. I stopped watching when my daughter was born because I didn't want to indoctrinate her with that. I was like, she's, she's, it's a blank slate. Like, I don't want to give her that burden. Like, I, if, if I, if there was a coffee company that had a CEO that was that bad, I would switch coffees, right? I can't, I can't bring myself to switch teams because that feels blasphemous, but I'll stop supporting them. So anyway, I got back. I'm a supporter now, but I've also resigned myself to the fact that I, I don't know, I could never see them. In a Superbowl, but I still want to watch because there's always a chance.

AI assessment note: “Six billion. Let me, let me double check that.”

Q but no, no, you're not an idiot because at the time it was like the unbundling of audio and the future Facebook. Dude, I remember when there was like a genuine playful, are we going to see the unbundling of Clubhouse? Into like sports radio. Yeah. Yeah, totally. I remember that completely. What is your biggest lational observation from seeing Serena in terms of the training, the dedication, the consistency?

A The weirdest dynamic that we have is I genuinely love every bit of what I do. My worst days, I really, I like, like we were saying before, like, I, I, I know how lucky I am to do something I love this much all the time. I could do it all the time. I literally could, and I love my family, but I could do this all the time. She did not love the process all the time, and she'd be the first to admit, like, I am doing this thing because I want to win. I do it for the trophy. I do it for the outcome, and obviously, look, being a professional athlete at that level is much harder than the work that we do, so I get that, like, it's just harder work as well, but the fact that she Put in that commitment so consistently since she was a kid is awe-inspiring, and, and I, and so then it just makes me even more motivated, even more incentivized, uh, but it is a weird dynamic because I, like, it's not like, and I, I think she's been pretty outspoken about this, like, this is, this was not something that she, I don't know, it was, it was a labor of love, but not in the way that we think about it. It was, it was a love for the outcome, And you just knew the process was the thing you just had to do. And it was the only way to get to that outcome, but you didn't like whistle on your way to work type of thing. And there are some days where I'm, I'm not whistling, but I'm like rocking out, uh, on the …

AI assessment note: “She did not love the process all the time... I do it for the trophy.”

Q And how much did he sell it for?

A Six billion. Let me, let me double check that. But I, yeah, and again, one of the worst owners of all time. And what's crazy about that is I still want to watch. I stopped watching when my daughter was born because I didn't want to indoctrinate her with that. I was like, she's, she's, it's a blank slate. Like, I don't want to give her that burden. Like, I, if, if I, if there was a coffee company that had a CEO that was that bad, I would switch coffees, right? I can't, I can't bring myself to switch teams because that feels blasphemous, but I'll stop supporting them. So anyway, I got back. I'm a supporter now, but I've also resigned myself to the fact that I, I don't know, I could never see them. In a Superbowl, but I still want to watch because there's always a chance.

AI assessment note: “Six billion.”

Q That's why you build media empire. Okay, so you, you invest then. It's crazy. The thing that we don't have investing in tech that you have here is ongoing cost though. You have to pay players. You have, how did, how did that work? And what was that ongoing cost there?

A So, so there is and there isn't. Like, if you abstract away There is a dynamic where there are some contract nuances to this, because obviously players, there's collective bargaining agreements, you know, there's salary caps there. It's not, it's not a one for one match to say that like, oh yeah, our star striker is the equivalent as like a 10 X engineer, but it's, it's similar. And so when it came to, uh, when it came to funding, it was two things. One, you know, funding off of good old fashioned revenue. Which is a nice thing, right? Just focusing on having revenues coming in the door that you can then invest more in the team. Um, and so it doesn't look as, let's say, high growth at all costs as a traditional startup. Um, and then there's also future rounds of financing. And so it was, it, from our vantage point, my thinking was, okay, this has been a slog to get done at Initialize. Now, not surprisingly, I don't know, six months later, I split the firm up. And so Caitlin, Lizzie, and I left, went and started seven, seven, six, basically took, took the, the squad and And we spun this up, and then I invested out of seven, seven, six as well. So now here's the net sort of next round of financing. Now, the, the, the bigger question and the bigger unlock that we can't control is when those media deals get renegotiated. Because when those get renegotiated, now you have a new sourc…

AI assessment note: “when it came to funding, it was two things. One... good old fashioned revenue.”

Q How would you summarize your brand today? People often call me the Charlie and the chocolate factory adventure. I'm not quite sure that's the brand I'm going for, but, uh, would you summarize yours?

A I don't know. I would love to know. I mean, when I see, okay, the buckets of things that I hear, I should survey people. I mean, the buckets of things that I hear are, uh, Serena Williams, husband, Which is great. I'm very happy to take that. I would much rather be known as Serena Williams' husband than, like, co-founder of Reddit. I'd also love to be known as Olympia's dad, but she's still three, so there's not a lot. She's still, she's got a lot of work to do. But I hope my reputation is one where I've not always made the right decisions, but I'm trying really hard to be on the right side of history across a lot of issues. And, you know, it's funny. It's almost Quaint talking about things like open internet, net neutrality, which were big causes that I championed five, six, seven, eight, nine years ago. But I hope the brand is about doing the right thing and, and hopefully one that sets a higher standard in an industry that has pretty low expectations. I mean, there are memes built around venture being an industry of just sort of lean back, lazy, soulless finance people. And there is some truth to that. I do think that is rapidly changing. And, uh, and I hope the reputation that I have with the founders is one that they know two in the morning, they can text that they know whether it's a small problem or a huge one that we can be the first call and that we can actually do som…

AI assessment note: “I hope the brand is about doing the right thing”

Q That would be a brilliant thing to happen. I do want to ask you that because I want to take it off the table just to start. In terms of initialized, what happened with initialized and why did you decide now is the time to leave and start the new firm?

A Well, twenty-twenty has been a very reflective year for me. You know, after the murder of George Floyd and, and really thinking about sort of the role that I want to play in the world, I, I realized I needed to, to step down from the board of Reddit. I did that in June and, and, uh, you know, was, was very relieved to see that they honored my request to replace me with a black director and, and also very relieved and excited to see that they were, were finally moving forward on some real policies to, to fight hate and harassment on the platform. But I realized I wanted to spend the next You know, 15, 20, I don't know how many good working years I have left, hopefully a lot longer, really intentionally building and making sure that when I have that future conversation with my daughter about what I do for a living and why I do it, that she's really, really proud of me. And this gave me a chance to really reflect on all the things that I was working on. And as proud as I am and as grateful as I am for what Gary and I have built together with initialized, you know, it came to a head this year because I realized that You know, I had been back at Reddit full time as executive chairman back. I left, I went, or I came back in 2014, which is right around the time that initialized started building out the team and, and the org and the culture and all that. And Gary was doing that solo as…

AI assessment note: “it came to a head this year because I realized that”

Q a content House. But what I worry about is two things here. Culture. It could cause rifts in the team with superstar cultures being created, and not everyone rises at the same time or speed. And performance on the pitch. What a lot would say is the only thing that matters. How do you think about those two, and is it detrimental doing all the media activity for those two?

A And then when it comes to teams specifically, look, there's always going to be that gap between the star player and the You know, the role player at the end of the bench, but teams find a way to navigate it. Um, I do think in this new era, you're actually gonna find more opportunities for those role players Because you're gonna see, you're gonna see folks who have fans that don't just have fans for their work on the court or on the pitch or on the track. They have fans because they're just beloved. And, you know, I, I'm not an F-one expert, but I feel like Danny Ricardo punches way above his weight because he has such a strong fan base now, thanks to that show.

AI assessment note: “teams find a way to navigate it. Um, I do think in this new era”

Q a content House. But what I worry about is two things here. Culture. It could cause rifts in the team with superstar cultures being created, and not everyone rises at the same time or speed. And performance on the pitch. What a lot would say is the only thing that matters. How do you think about those two, and is it detrimental doing all the media activity for those two?

A And then when it comes to teams specifically, look, there's always going to be that gap between the star player and the You know, the role player at the end of the bench, but teams find a way to navigate it. Um, I do think in this new era, you're actually gonna find more opportunities for those role players Because you're gonna see, you're gonna see folks who have fans that don't just have fans for their work on the court or on the pitch or on the track. They have fans because they're just beloved. And, you know, I, I'm not an F-one expert, but I feel like Danny Ricardo punches way above his weight because he has such a strong fan base now, thanks to that show.

AI assessment note: “you're actually gonna find more opportunities for those role players”

Q What is the number, you know, we do premortems for investment mammos. What's the number one reason why this would not be a billion dollar company from here?

A Oh, that's funny. So we, we call it a steel man. So like, what's the, what's the reason why this company won't be successful? Assuming everyone kind of does the right thing. I don't know. I mean, with, with Bob and Willow, uh, in control of the board, I, the sky's the limit. I really, I don't know what would stop it. I mean, the sports is so funny. It's like I said, it's not, Probably, okay, maybe the biggest threat would be a meta threat about the NWSL and other leagues. Like, could Europe get its act together and have a competitive league with the NWSL? There's some great teams here, obviously, in England, um, but that league's catching up, but it's still not, not at the level of the NWSL.

AI assessment note: “maybe the biggest threat would be a meta threat about the NWSL and other leagues”