Alexis Ohanian – From Reddit to 776, a Technology Company that Deploys Venture Capital (EP.388)

25:04bonus points if you are able to offer even suggestions or insights. But that is an exercise that Caitlin put me through seven years ago. And I cannot tell you how many times I come back to it when trying to deliver feedback, even to my kids. I don't know if that's healthy, but they bring a lot of these management principles home. So we'll see how it turns out, the little ones. When you took this thing from 8 million revenue to 150 in just a couple of years, what did you see differently in terms of your ability to scale and grow than when you were around the company the first time? Well, I have to give a lot of credit to the folks who did the real work building that.

25:44And the good news is I work with some of them today. Our team president at the LA Golf Club, Neil Hubman, was our head of sales there at Reddit during that entire time. In fact, he came on right around the time I did and was at the company up until a year ago when joined us at LA Golf Club. And so you've got folks who were in the right role, executing the right way. And frankly, as bad as Reddit looked with that 8 million revenue and this revenge porn branding in 2014, folks who could see past that saw tremendous potential. I mean, we did have 8 million in revenue, but it was so notoriously underperforming for so long that it's not like we were just starting there.

26:29We had an audience that already should have been generating way more revenue. We had engagement. We had cultural influence that should have been way more valuable. It was just being under managed, let's say. And so what I saw there that most impressed me though, was if we could attract folks who saw the potential, who were willing to run into the burning building and basically say, no, no, no, there's something really special here. We can save this and this can be a career defining opportunity for me. In a way, because it was so unattractive, I think we also just automatically separated out a lot of folks who wouldn't have been the right fit.

27:05So I'm not saying make your business look as unappealing as possible. And what was so compelling was just by creating a modern philosophy around how to treat employees, how to reward employees, how to build culture internally, in many ways, frankly, reset a culture was really exciting because then I started to see how something I never took seriously, like values. I always thought company values were just bullshit people put on a wall. And in plenty of places they are. At the best performing companies, they really are an extension of the founder. At some point you grow so big, or even it doesn't take that long, you cannot be a part of every decision.

27:47You should not be a part of every decision. And so these values, when well articulated, are a way to scale as if you're in that room. And then what was also so interesting is I watched as they also evolved. We would do these audits every year where we'd look back and say, okay, these values that got us to where we are now, look at where we were a year ago. Do we still need all of these? Should we evolve some of these? Because now we've actually accomplished that thing. We wanted folks to take pride in the work they shipped. I stepped into to an organization where we were frankly just shipping product that wasn't great.

28:18It was really, really important that we shipped not just often, but also well. And we took pride in our work. And that needed to be a value, this idea that folks would almost figuratively have to sign their name on the things they were putting out in the world. And if you didn't want to work in a place where you had to stand by your work, that's fine. You should just do that somewhere else. And after a year or two of doing that, I remember Caitlin saying during one of these off sites, look, we've reached a place now where I feel like we don't need this value anymore. What do we all think and how do we evolve that as an executive team.

28:46To see those things evolve, to see it when it's done well is so powerful because I think to do really hard, big things, you need to find ways to scale that limitless well of founder energy that's unfortunately limited to 24 hours a day and usually just a few humans. Once you get that internal flywheel going the right way with the right people on a platform like Reddit, you also have the challenges of the external environment. And it's not just Reddit, the social media. You mentioned revenge porn. You've got harassment and hate stuff. How did you think about all of those issues? And it's obviously broader than just a Reddit issue.

29:25The internet, frankly, that I spent my childhood growing up on always had its weird, dark, awful places. But the community platforms that existed that by and large defined the internet in those 90s and early aughts, the number of people online, especially online a lot, was far, far, far, far fewer. It was a smaller sampling of the world. And I think all of us, and I'd say all of my peers in the social media world, all those other founders and CEOs, we had rose-tinted glasses on because, yes, we all were white dudes. That's worth stating. We just didn't encounter much awful content in general. The forums were smaller.

30:06The topics were web design forums. This stuff existed, but it didn't metastasize like it does now because the internet is so ubiquitous because social media is so ubiquitous. What happened on the internet did not become news globally that same day. So it wasn't something we thought about from the jump. And frankly, in the early days of Reddit, if there was something really awful, hate speech, whatever, we would just ban it outright because we were the mods effectively of the handful of communities we had. But as the platform grew, we had to build more of these tools to help our moderators do that job.

30:40And then part of the challenge also, frankly, was leaving in 10, coming back in 14. That was a four-year gap where we were now going to play catch up on a lot of things that I could say maybe I would have done earlier. And then we all saw more and more people moving online, spending more of their time online in the teens. Now here we are in the early 20s where truly culture happens online. That is the first place where this stuff happens. I don't say everyone, but it's a whole hell of a lot of us spending a heck of a lot of time. And we're seeing now more and more of the negative consequences of that prolonged exposure.

31:15And look, there's philosophical disagreements, of course. I mean, I left Reddit pretty publicly in protest back in 2020 in the wake of George Floyd because it did not align with my views that the company would take such a stance in support of communities of color and black communities in particular, and also still have thousands of hate communities. And when I brought this up similar to protests I had about some of these extreme violence communities like watch people die, I was in the minority on that board. And so it was important to me to just get aligned with myself and challenge the company to ban those communities once and for all, which they did after I resigned, and replaced me on the board.

31:57And I think private companies, I think of it like Javits Center. We're here in New York. If you've been to a Comic-Con there, you've been to an event there, Javits is a convention hall, pretty big, that is effectively privately run. It still exists in the United States of America, which is a country that honors free speech, and it's an awesome right. But if you're in the Javits Center. It's a private enterprise. And so Javits has every right to say, yeah, sure, you want to host Comic-Con here, great. But if you want to host your KKK community here, we're not going to allow that. If you just take it out of the online world, there is something insidious about this idea of seeing a Pokemon next to a KKK booth.

32:40It almost normalizes very, very heinous behavior. And look, the World Wide Web still adheres to these principles of free speech. You can still find those communities online. I think I actually, although I find them vile and disgusting, I understand why they need to exist on an open internet. The difference is pre-social media, they all existed in their weird little vacuum. And the only way it really metastasized was if some person you knew sent you some email that was like, hey, check out this website. And you'd very quickly be able to be like, you're weird. No, thank you. But social media unfortunately gamifies this outrage that actually helps the most outrageous content metastasize and spread a lot faster.

33:18And so here we are in a place where I feel, yeah, if you are the owner of the Digital Javits Center, you actually can absolutely decide what communities belong and don't belong. That's your right in America to do that. I think things get a little convoluted when we muddy the discussion with the public square, because if we're using the public square metaphor, that implies that these websites are cities. If there's a public square, some kind of digital towns, who decides who the leader is in the digital town? The board? So it's not a democratically elected leader. It is a digital town square in a city that is run by a dictator that its citizens have no lever to battle with.

33:58And what's nice about a democracy is, yeah, we can have that literal town square where we have the ability to access free speech. But we also have this amazing set of levers from the founding fathers that allow us to vote and make decisions if we don't agree with something to make change. And so that's for me where the digital city metaphor falls apart. So all this is to say, the most encouraging trend I've seen of late, and I think AI is actually going to help usher this in, AI and the glut of AI generated content is now going to make proof of humanity much, much more important for UGC websites because it will be really, really important, not just to keep down spam, but because users presumably want to see what humans have to think.

34:41And I actually think this wave of proof of humanity that consumers are going to ultimately demand is going to lead to a better quality of conversation on the internet. I don't want to get rid of pseudonymity, let's call it. It's not pure anonymity. I think Reddit works because you can choose a username and Fluffy Bunny 12 is still an identity. So it doesn't descend into total chaos because you actually have accountability. You get the freedom to be, let's say, more honest than you would be on your Instagram, but you still have the accountability where you have an identity you actually care about.

35:13And Fluffy Bunny 12 still matters in a way that if you were purely anonymous, it wouldn't. We're gonna see a shift. And Gen Z seems to be leading the way in terms of not wanting all of their lives digital. I just saw this uptick in dumb phones now in the United States. So the United States is one of the few countries in the world where we're actually seeing a rise in the sale of dumb phones, which I can't help but feel is a part of this culture of, okay, the pendulum swung so far on user-generated content and living on our phones that perhaps there's some energy now swinging back. So I'd love to shift a little bit.

35:45You've had your operating experience, a little bit of early venture experience, and now the platform and some views about a bunch of different things into a venture capital firm. Would love to hear how you thought of bringing all this together in what you've tried to do at 776? For sure. I saw firsthand the power of designing community software, Reddit. And I saw the opportunity in early stage venture, building initialized. And in 2020, I realized that if I was going to do my life's work, it would be building software, which I've called Cerebro, which is a deliberate X-Men reference, to be a full-fledged operating system to run a venture capital firm just better, cheaper, faster than anyone's really done before.

36:33I love building software. I love building community. My partner, Caitlin, who founded the firm with me, like I said, she obviously deeply understands both community online and offline from our days at Reddit. And so we're taking a unique approach. We've built Cerebro to be, and this is where we do all of our work as a firm. We do a tremendous amount of our founder support through it. A lot of it is self-serve. I don't want a founder to have to ask me, hey, who do you know at insert company name? Because that's a bad query for my brain to figure out. I talked to all my billion-dollar CEOs, these seed investments that had grown up, and I said, what was the most valuable thing that I did for you?

37:10And one of the top results was, oh, intros, your network's strong, people take the intro. It was tremendously helpful. And I realized I sorted that list of things. And at the top of the list was what was most productizable. And what I realized was here was the perfect thing. My brain, not a very good database. A database is a very good database. And so that simple query of, hey, who do you know at company X is trivial if it's all living in software and it's searchable by founders. It's a pain in the ass if you're asking me. It's also a waste of everyone's time. So that was the very first tool we built in the Cerebro, which I took about 40 ,000 contacts that I'd amassed in a personal CRM over my career, made it searchable, and then let founders click a button to draft an email for me to basically edit and approve and send that would come from my inbox.

38:00And that was V1. And we've since built a whole full-fledged products. It's tremendous. And then the other benefit of doing all of our work in software and scaling, now there's four investing partners, is the exhaust of that engine is data. And so over the holidays, I got a little frustrated because I was browsing other firms' websites. And I realized every single VC firm, all these early stage VCs, all the same promises on their website. And I thought, well, that's not differentiated. And I thought worse, the very best founders don't want to hear promises. They want to see receipts. So we just built the 776 six websites.

38:36Now it has real-time data. In the last 365 days, you can see our median response time to founders. I think it's like one hour, 24 minutes. The number of intros we've made, workshops we've hosted, sales meetings we've had, even the user engagement of Cerebro, the app that we've built, not just of our team, but also how often our founders are using it. By putting a scoreboard, which we've always had internally, but now putting it externally, I just wanted to make it very clear to the world that we are built very differently. We are more like a technology company that deploys venture capital than anything else.

39:10And God helps someone who's going to compete head to head with us on a deal, who's going to say, oh, oh, you should take our term sheet. We'll help you a ton. We'll be super responsive. We'll help you with press. We'll make lots of intros because that founder is just going to pull up the website and say, well, show me the receipts because these guys actually have data for all the things that you're promising me. I don't know what your answer is to that. Do you tell your poor admin to go harvest your calendar for the next 24 hours? But it's exciting. This is the kind of accountability the best founders expect.

39:43This is what they expect to provide their investors. And I think it is a great time when investors are now looking to have a similar kind of accountability to their founders. We're going to take a quick break in the action to tell you about SRS Aquium. Want to make sure your M &A processes aren't stuck in the past? partner with a company that's been defining the future of dealmaking for nearly two decades instead. When it comes to M &A innovation, SRS Aquium has reshaped the way that deals get done, streamlining processes for maximum efficiency and minimum headaches. Professional shareholder representation, online M &A payments, digital stockholder solicitation, SRS Aquium pioneered each and continues to set the bar for game-changing innovation.

40:35So leave the days of disjointed deal management behind and define your future with SRS Aquium, the smartest way to run a deal. Learn more at srsaquium.com. That's S-R-S-A-C-Q-U-I-O-M.com. And now back to the show. So that aspect of operationalizing how you work with your portfolio companies has to come after you found the portfolio company. So if you circle back to the top of the funnel, what is it that you're looking for? We are generalists. And so I think I've benefited through my entire investing career and probably frankly, in building Reddit from being pretty intellectually curious and promiscuous.

41:25And so as a result, I have a really broad network. You got to imagine being a first check in companies ranging from Coinbase and Instacart to Patreon and Rowe and Flock Safety, a variety of different industries, very different backgrounds. So much of what is at the heart of Cerebro is network. The first product was just those 40 ,000 contacts I had in my own CRM. And so we're very cognizant of the relationships we're building, wherever the most signal is in our network. A lot of VCs, so much of our deal flow still comes through recommendations of folks in our network. There's a lot that just comes in through the front door in the inbox, but there's a very, very significant number that come through some warm recommendation from someone that we've worked with or invested in before, what have you.

42:13And that still ends up being a really dominant force. And that starts to guide a lot of how we think about the world when we just want to get smart about a sector. We made our first ever space tech investment in our first fund, a company called Stoke. And they are a couple of ex-Blue Origin folks building reusable rockets that will, the second stage, the little, the top will land itself. Amazing team on paper. I have never built a rocket before. I can evaluate most of these technologies pretty quickly if they're software, but this is very hard hardware. But we got to conviction. We did the investment.

42:47That company has been tracking well. And so now that opens the door to a whole nother network of space tech founders through a really credible CEO. And that's opened the door to companies like Astroforge. And so we're going to see more of this. And what gets exciting is we get to spend time with actual builders on the cutting edge of tech. They teach us what's happening. We get to conviction about spaces or sectors. And then we've got some of the biggest reach in venture on social. I'll literally tweet out something I'm excited about or confused by and start to get a trickle and then a stream of pitches around that.

43:24And that's also tremendously helpful. We haven't announced yet, but we just invested in a company based on a tweet that I made a year ago about fixing the American food system because we saw vertical farming boom and then crash. And there were parts of that business model that made a ton of sense, a lot of other parts that didn't, at least for venture. And I was desperate to figure out what the next version of it was going to look like. And I think we found it. We ended up investing in it and it all tracked back to a tweet. So it's a mix of things, but Paramount is surrounding ourselves with high output, high horsepower founders.

43:58There's three aspects of what you do that have come up in that thread. So one is the tweet, your social media presence. Another is is sort of conviction and ideas. And then the last is founders. Maybe start with this question of the idea and the founder, and how do you think about the intersection of the two? We have a deal tracker in Cerebro. And when a company goes to the pitch stage, anyone who is in that meeting gets a notification that they need to go grade the founder. They're grading the founder on a number of different criteria. The most, most, most important One is around the founders themselves.

44:34So some personality traits that we look for. Then there's the more standard stuff around product, market, timing. Those are all important. Oftentimes, they're usually just reflecting back on the founder. If the product is poorly built or has no taste, it's a reflection on the founder. If the market opportunity as presented to us feels off or we're going to get 90 % of the whole market audacious, again, it's a reflection of the founder. The timing one is an interesting one because, gosh, I mean, I guess I was a victim to it with my mobile menu. Obviously, smartphones have solved the problem of ordering, whether it's to skip the line or just get delivery.

45:12But the timing was off. And I'd like to think I was a good founder. I just got the timing wrong. And that's the one that can stymie a company. We'll likely still invest because it's something very hard to time, especially when we're the literal first check in a company. So it won't seem obvious to the rest of the world for maybe three to five years. That's part of the fun, frankly. I'll tweet about investments I've made. March of 2019, I am probably one of the few people in the world, certainly in venture, tweeting that women's sports was the most undervalued opportunity in the world, and I was going to buy an NWSL team.

45:47I had so many people tell me how wrong I was and how much money I was going to lose, and Angel City has done pretty well since that initial check. And this is part of the intuition I want to build for the rest of the investment team who has not as much experience as me, but a whole lot of it, is what we're looking for in founders who are capable of building these multi-billion dollar companies. There are these traits that I keep circling back on that seem to just be more and more important as I reflect on them. I assume you want to know what they are. Sure. So at least one of the founders has to be a good communicator.

46:21and that's not necessarily charismatic or can get up on a stage and give a TED talk. They need to be able to one, understand their idea, communicate it in a simple, effective way and then also just be able to synthesize what is going on in the broader world and then specifically who they're talking to and be compelling. And so that might be pitching us as investors. That might be getting someone to quit their job to come work for them, to be one of the first 10 employees of a startup, very risky. It might be convincing someone to buy their software. Maybe it's a B2B sales business. And at least one of the founders needs to be a very compelling communicator.

47:05There's this je ne sais quoi around it. There are traits you look for. They're probably not using a lot of jargon. They can speak plainly and confidently about what they know. And it's such a nuanced thing, but that one seems to be over and over again, one of the clear differentiators. There's another one around resilience that we look for. And again, that's a hard one. You can't ask someone, hey, tell me your most resilient time or are you resilient? Yes or no. But you look for things that they've built or done in the past. This is going to get hard. Starting a startup, the moment you're meeting me, this is literally your first check.

47:39There are much better ways to spend the next decade of your life if you want to make money. I try to talk people out of starting a startup all the time. As much as I try to broadly encourage people to consider starting a startup, I also want to just say, gut check, do not do this for wealth. Do not do this if you're just trying to make some money because there are smarter ways to do it. Do this because you lose sleep at night because this thing doesn't exist. And you want to bring it into the world, kicking and screaming, knowing that it will suck for extended periods of time. And you're going to have to be the one to pick yourself up.

48:14Don't even count on your co-founders. Don't even count on your investors. Don't even count on your friends and family. It will be on you. And if that is a road you want to go down, if you want to chew the glass and stare into the abyss, then okay, great. We need people like you, but try to talk folks out of it. So these are the elements that we look for. And what's so fun about this gig is whether it is a crypto company or Mr. Beast's company or whether it's a space tech company or a climate tech company, no matter the sectors, those attributes carry over from CEO to CEO to CEO. And it's fun because these are not folks who are inheriting someone else's company.

48:58I don't think I could do any other part of this job of investing well, certainly not nearly as well as I can the early, because it's a kind of alchemy that I'm just looking for something very different than, for instance, if I did public market investing, where it's either entirely data-driven or maybe there's some other magic to it. It's the alchemy of early stage where you can literally spend 30 minutes with a person who has only an idea and say, yes, actually, this can be a multi-billion dollar business. And thank God for the power law. You don't have to be right even half the time. You really just need to be right once or twice out of a fund and get some great returns.

49:37So a lot of people finding you with ideas can be tied to this massive social media following that you have on Twitter, on Instagram. How have you thought about putting your time into those platforms and what it takes to resonate and build an audience? I have done a terrible job building my audience and I know you're going to be like well but you've done a pretty good job of it I look at full-time content creators like Jimmy my friend Cleo Abrams she's got a few million on YouTube she does these amazing explainers about hard tech it's called huge if true and so I see the work that they do it is a literal full-time job making content you know this dad it's a lot and if you want to do it well you got to do the work you got to get the reps him.

50:20And so we're getting better now in part because I've got a team and they're not just scaling me for content. They're also scaling my partners because this isn't just the Alexis show. And then you know me, I love software. So I've built more and more software to help us do this better, cheaper, faster. We've built our own version of it into Cerebro. And so this lets our content team, but also our founders ghostwrite entire tweets, LinkedIn posts for us. So again, we're finding these efficiencies where now I can just get a push notification and be like, oh, here's a post. It's already scheduled to go.

50:54Let me hit edit. Yeah, it looks good. Let me add this emoji. Boom, send. And again, creating all these efficiencies that also lets us report back number of impressions, number of engagements, click-through rates if there's a link. We also then just shipped an app called Muse. Well, really, it's a feature within Cerebro inspired by Cameo or Fourth Wall where our social team, even our founders can basically ask us for a selfie video or audio with a prompt. It's just like you might pay some C-list celebrity to make a birthday video for you. Our founders can do that or our social team can. And so I'll get a video that's like, hey, let's talk about Caitlin Clark's record Nike deal and how it affects the future of women's sports.

51:34And I get that prompt. I see it on the screen. I record that video in under a minute. I hit send. I don't think about it again. And whether it's the founder who requested it or our content team, we requested it. They get it. They've already got the transcription. They've already got it closed captioned. They can now just do a few edits and boom, it goes live on social media. And so these are all tools that we build because we reach this pain point. We're doing the thing so much and there's so much friction in it that could be solved with software that I just put it on the product roadmap. And this is fun because I think content creation is only going to get more important.

52:07We talked earlier about the AI wave. I think of the world in barbells a lot. And so as it gets easier and easier to create AI-generated content, there's going to be a ton of it, tons. And it'll be really good. But because of that, you can just imagine the glut of this content. Culturally, we'll get used to it. If you told me five years ago that we would have a spidey sense for, oh, that looks AI-generated, now you find it everywhere on social media. There's definitely a Facebook demo that is getting duped on the daily, which is hilarious. but if you're a sophisticated internet user, you're like, something's a little off.

52:45So it's already entering the culture and I think that other side of the barbell where again, proof of humanity will really matter. I think in a world that's gonna be awash in content, standing out as human, almost intentionally so, is actually gonna have more value. I think in a world where there's just so much of that stuff, it actually matters more to be an original content creator. Build that following, which will let you break through the algorithm them and give people a reason to pay attention to what you're saying. I'd love to ask you about one of your investments on that other side of the barbell.

53:18Brent Montgomery introduced us. I know you partnered up with him in this mantle collectibles business. How does that fit into your view of the world? Well, a couple areas, obviously inspired a lot by Reddit. Six years ago when I got back into the hobby with trading cards at first and then game one collectibles, video games, all these things. A buddy of mine was like, it's back. And if you want to know the latest and greatest, you have to check out this forum. And it was like I was time traveling because here was a PHP BB forum, just like I had built in 2004, except now in the late teens. And I was shocked.

53:54I was like, surely there's got to be better communities for this, like more modern. And he was like, no, this is it. And I thought, okay, that's an opportunity. I get introduced to Mr. Montgomery. He's got his deep background on the content side, Pawn Stars, and we're doing the Golden Show. So he knew what I would call top-down, high-quality media and content creation. And he already had a passion for collectibles. And then I knew the bottom-up UGC. And we said, look, let's partner on this thing. We'll start with the UGC side because I know how to build products. We can get that going. And then from that community, we'll start to see things that bubble up that we'll be able to then take a top-down approach to make even better.

54:34And frankly, this is something I wanted to do at Reddit for a very long time. We just had other priorities where user-generated content can do an amazing job servicing a novel idea. But a crowd cannot easily create that next step of content. So a story everyone knows from the hobby is all those mantle cards. I think they were tops mantle cards that got dumped in the ocean. Let's use that example. Let's assume some users like, hey, it's the anniversary of those cards being dumped in the ocean. And there's a thread and a bunch of the people in the thread upvote something about, I really want to know from that executive what they were thinking.

55:10And maybe this isn't that interesting story, but imagine that. That is where top-down content can actually go and sit down with this guy and interview this guy and actually make the piece of high-quality content that a bunch of random people on the internet cannot easily make. And so we asked that question, why a lot? And that for me is the lever where you can have scale with UGC, and then you can have the top down really amplify and tell some of the best stories and then create this great flywheel. And we got really lucked out with amazing CEO, Evan, and off to the races. And so I'm excited. One, proof of humanity, these vertical communities that can show this is where actual humans are coming to talk about their actual passions combined with this renaissance of alternative assets.

55:55Trading cards boomed during COVID. They obviously took a big tank along with crypto and all these other speculative things after, but already have started marching back and we're seeing record high auctions for a lot of the high-end stuff. And I think as an asset class, it's here to stay. Mentally, I keep it in the same part of my brain as art would have historically been, except art is not nearly as culturally relevant as these are because the power of nostalgia and the power of sports in particular, again, keep an eye towards one of my favorite Jeff Bezos quotes is people don't ask often enough what's going to stay the same in 10 years.

56:29They're always asking what's going to change in 10 years. And so keep an eye towards 10 years from now, AI generated everything is ubiquitous. What are the things in the pillars of entertainment that are going to matter more than ever in a world where every screen we look at will be perfectly programmed for exactly what we want to see, when we want to see it, the way we want to see it. There are genres of entertainment, if you think about traditional television, cinema, they're going to have a hard time adapting to this because it's a lot of really good competition. But sports, sports will be the one last place for traditional entertainment where you are guaranteed to feel the humanity.

57:07No one will want to watch robots play basketball. Music sits in the middle. My daughter is still going to want to go to Taylor Swift because that's like a religious experience, but there's plenty of artists that are going to be displaced in different ways because it's just not that special. The one hit wonders, they're going to have a hard time, but sports, sports is going to thrive. And you're still going to want to go to see the next game, even though you know you're going to get your heart broken because every screen in your life is giving you this perfect digital dopamine hit. And it's going to be a surreal, definitely a dystopian version of this.

57:41And I'm a tech optimist that's looking on the bright side of where this goes. I do think that will actually as a species, we will crave a break from that digital dopamine drip because we didn't make it this far to just be sedated with exactly what we want when we want it. Sometimes when we were hunting the gazelle, we didn't get the gazelle and it sucked. And then when we finally got the gazelle, it was great. It tasted better than ever. And so there's a version of that that still needs to be fed in us. And that's where I think sports just continues to thrive. When you're talking about sports, I just have to ask you, what have you learned from your wife?

58:19What have I learned? Well, it goes without saying, I wouldn't have tweeted that prophetic tweet in 2019 about women's sports, nor would I think I have started Angel City if I hadn't seen firsthand that women's tennis in America was the dominant sport. So look, I didn't follow tennis. I knew who my wife was when we started talking, but I literally had never watched a tennis match. I grew up in a household where American football, NFL specifically was the only sport that mattered. Tennis was a bullshit country club sport. Sorry, dad. And that's what I played. That's what we watched. That was it.

59:02But I was obviously very aware of the Williams sisters culturally, but I just had never watched tennis. I watched my first match and I thought, oh, this is amazing. I got this sport way wrong. Just watching this thing courtside, this sport is way harder than I thought it was and way more exciting. I didn't even watch a men's match for a year. When I saw my first men's match, I turned to my buddy and I was like, dude, why are they playing to five? That's dumb. I was a total neophyte coming into this. Here's an NFL sports fan. I'm already pissed because the sport won't let me cheer whenever I want to cheer.

59:40Statistically, if you're only playing the three max, each point matters more. The stakes are higher. So that was my first impression of tennis. I was like, this is great. Every point matters. As soon as I'm sitting in a match where it's the five, I'm looking at my watch and I'm like, but this first one doesn't even really count. This is a less compelling product than the women. But then I started to see the numbers of viewers here in the United States. And you look year after year after year, more Americans watch the US Open women's final, which is the big American tennis match, than the men. And it doesn't matter.

1:00:18There doesn't need to be a Williams sister in it. There doesn't need to be an American in it. You could watch two non-Americans. This happened a couple of years ago, one head-to-head with Djokovic, who was chasing history, more Americans watch the women. And so that showed me, oh my God, it took a lot. It took Billie Jean fighting for pay equity. It took generational talent in Serena and Venus. And with that true, true, true American excellence, but all those things happened. And as a result, because again, the cash money started showing up for the players as well, you now had an opportunity where for the United States of America, women's tennis was the top sport.

1:01:03Even just being competitive with the men in pro sports was unheard of. You couldn't find that anywhere else. But it was enough of a proof point that I said, okay, so if the women of US soccer are excellent, and even an average sports fan, again, I'd never watched women's soccer before, never watched men either. But if I close my eyes and I was asked, think of American soccer her greatness. I would think of Chastain hitting that penalty kick. I would think of Mia Hamm. I was aware of Alex Morgan and Rapinoe, but I was like, yeah, the women, because the American men have never been great at soccer.

1:01:37And I thought, okay, I can market greatness all day long. And then I started looking at the stars of the league and I see Alex Morgan with all of her followers. And I'm like, that's the free market of attention. And there's millions and millions, tens of millions of people paying attention to Alex Morgan. So she's got to be worth more than And at the time, our team had just sold for$3 million. The math doesn't math. And yes, I had that confidence full stop because of Serena. And what she was able to do, set a bar and opened a door for women athletes. Obviously, I've got two daughters. I do care about the gender equity issue.

1:02:12But I actually care much more about the fact that the free market spoke loud and clear. And if you look at the list of top earning athletes every year, the only women are almost all tennis players. That's the global impact that Serena Venus had, that Billie Jean had to level the playing field, get equal investment. And the excellence followed and voila, people want to watch that. And so you're seeing it now. Caitlin Clark is having that moment. I think it's going to level up the W in a huge way. And what have you seen about how that transcendent excellence in sports translates to day-to-day life?

1:02:49That's funny. I see Serena as my wife first, and that's not to say she's not excellent. I hope it's actually heartening to hear that it's not literally every single thing is excellence embodied, whether it's Serena or Tiger or MJ. No, actually, they're kind of normal. I mean, they're not. They're exceptional humans. And what is it? They put on their pants one leg at a time like the rest of us. There's actually something really remarkable about the normalcy. I think one of the best parts of Serena's evolution, and she would say this, she has said this, is that right now she gets to spend so much time as a mom.

1:03:35She was just volunteering at the book fair at Olympia School. My childhood was obviously very different from hers. At a very early age, she had to take on tremendous responsibility and do incredible things. So this is the first time she's really been able to now have a normalcy that again, growing up, I think most of us, that's just what we consider life. But for her is something that now she wants to be great at and is great at. And it's awesome seeing her do that. One thing I can say for sure though, regardless of whether it's on the court or off, she is the hardest critic on herself. And so that same instinct that drove her to want to be better, she always says there'd be no Serena without Venus.

1:04:18She always had to be a little better in order to keep up with her big sis. And she applies that whether or not she's making cinnamon rolls for the family or just watching over our kids. She really goes to 11 always. She wants to be the best and she's so incredibly hard on herself. And I guess that's the other side of it too. No one should assume to be that great comes without tremendous work, tremendous sacrifice, tremendous cost. And that's probably the other thing that I think I see firsthand. And I think one of the reasons why early on it worked as well as it did for us, because I spent most of my life in relationships where folks didn't fully understand why I was the way I was and why I worked the way I worked.

1:05:12And I found myself in a relationship with someone who obviously didn't have any trouble understanding and obviously was doing things on just another level. And so it motivated me and it helped, I think, tremendously to just be around someone who just was operating on that frequency. A couple of quick closing questions. We'll get you out here. What is your favorite hobby or activity outside of work and family? Those are only two things I do. No, I have pancake art, but that's technically family. I do crepes on Saturday. I do pancake art on Sunday, all on my socials. I play Helldivers too with my buddies every now and then.

1:05:47My best friends are my guys since I was five years old. So they're still in the group chat and we'll fire up Discord and we'll play Helldivers once a week, try to get in a couple hours. I started playing golf, but again, I do it just to play with my daughter. So I'm her caddy on Sundays and I'm trying to learn as well. And I just got into making brisket. So I started smoking, got a Traeger a few months ago, and I do it every Friday night now. I gotta say I got it pretty good. Olympia randomly loved brisket. We were in Austin once. She tried it. She loved it. And I was like, great. My daughter loves a thing.

1:06:17Here's an excuse to get a smoker. Now I'm gonna go down the YouTube rabbit hole to master Austin or Texas style brisket. And now I'm doing briskets and I've got my own cow guy now. I'm in a total smoking meats phase. What's one fact that most people don't know about you? I was getting my coffee this morning and the woman hands me the coffee and she's like, are you Alexis? And I was like, yeah. And she was like, wow. She was like, say hi to Serena for me. Of course. And she's like, you're a lot taller than I thought you were. And I was like, really? I get this so often. So I guess the surprising thing that I keep hearing about is that people are surprised that I'm 6 '5".

1:07:00But now you know, there's a surprising fact. What's your biggest pet peeve on the investment side? Biggest pet peeve is, well, it's my alpha. It's the fact that very, very, very few people in this industry are building venture firms like technology companies. And yet we all talk all day long about how we invest in technology companies disrupting antiquated industries. Well, I've got an antiquated industry for you. It's called venture capital. And I know in the grand scheme of things, it's not the oldest, but it's still antiquated if the best technology people have is some rudimentary CRM and what, Airtable.

1:07:38So that's my pet peeve. Which two people have had the biggest impact on your professional life? I'll say Caitlin Holloway, who works with now almost a decade since the Reddit turnaround now is 776. And this is going to sound like a shameless plug, but I made a donation to Robin Hood Foundation here in New York. And Paul Tudor Jones has really been just awesome. And he's certainly opened my eyes to what a really high functioning foundation could look and operate like. And I have my little baby 776 Foundation, not on the Robin Hood scale yet, but it has really opened my eyes to it. I know you asked about professionally, but I'm going to include the philanthropy part because I really want that to be a big part of my legacy.

1:08:27And I do for-profit venture capital work. We're trying to maximize returns. And I want to do so in a way that my kids will be proud of me for. And I think we're tracking well there. And I also think that a lot of these same attributes of entrepreneurship can be applied to philanthropy and certainly in the way we've given out. So I've got 20 million in climate grants that I've been putting out every year. We take open locations all over the world. It's say, go build, go do something. If I can use these muscles that I've exercised around early stage investing and building companies to help a whole other generation of entrepreneurs do great things to help make the world suck a little less, that's a win.

1:09:08What's the best advice you've ever received? My mom told me that I should never live my life for what I think she or my dad want. and what she said was specifically she was like look you're gonna make me proud as long as you are living your life and as long as you are doing what you feel is right for you I'm gonna be proud of you I don't care about what the details are I just know that's what's gonna make me most proud and I can see you doing it and keep doing it and it's wild because I've come to meet so many people whose parents for whatever reasons were much more prescriptive like oh you gotta get a job here you got to do this, got to do that.

1:09:52And I feel like one of the most liberating things that she did, which maybe that was part of her master plan, even while I was going down the road of something very prescriptive, like go be a lawyer. She just kept reminding me, do you find whatever it is that you want to be great at and then go do it the best you can. I didn't realize at the time how special that was. And I feel like I've had that echoing in my ear ever since. And now as a father, I'm going to have a six-year-old. But Olympia comes to me and her mom with a new thing she wants to do when she grows up probably every week. Right now, it's a fashion designer.

1:10:25Last week, it was a model. One week, it was a diva. Then it was a veterinarian before that. Actually, no, tennis player. As of yesterday, now she wants to be a tennis player. But I try to carry my mom's message forward, even though she's not here, which is just, look, the only promise you have to make to us is that whatever you do, you've got to just do your best at it. Do something you truly want to do. Hopefully be useful in the world with something and we'll support you and we'll love you for it. All right, Alexis, last one. What life lesson have you learned that you wish you knew a lot earlier in life?

1:10:58I'll give you the one that I learned in my 20s. Actually, I don't wish I learned it earlier, but I'll still take it. The greatest gift that I got seeing my mom struggle and fight brain cancer was Here I was in my early 20s, feeling invincible, starting a company. Oh, look, I'm a CEO. And I saw firsthand what someone cares about when they've got a few years to live. So even as I came into early wealth, as I came into all this stuff, I never got it twisted because I can tell you, spoiler, the only thing you're going to care about if God willing, you get a long and healthy life to look back on is the people that you spent it with and that you love and the experiences you had with them.

1:11:37and those memories. And hopefully those people are still there with you and that's it. And what was the best part of a really hard time was seeing her live that out every single day. I made that money. I knew what I was going to get my dad. My dad, we had a couple of nosebleed season tickets for the Washington commanders now and upgraded him. I got us four tickets and we're front row. So my two friends would come. I didn't miss a game for 10 years. And so that was, I knew what my dad wanted. And I asked my mom, I was like, what do you want? She was like, I don't want anything. I was like, come on, you gotta want something.

1:12:08She's like, I don't want anything. Every week I'd call, be like, come on, mom, let me get you something. Every week, nothing, nothing, nothing. And finally she's like, okay, look, you're going to keep calling me. Just make a donation. This is a nonprofit that I love that works with dogs and shelter pets. And I was just like, really? I wasn't a billionaire, but I made a lot of money here at 22 years old. I'm like, mom, let me get you something. Didn't want a thing. And for all those years that she had left fighting, the only things that mattered to her were the time that we could spend together.

1:12:34And thankfully, she got to spend a ton of time with my dad, a ton of time with me. And yeah, so that's the cheat code. And so sitting here at 40, I still feel as ambitious as ever in my professional career. And I know that so much of what I'm doing now is hopefully part of some bigger picture that I get to paint for my two kids and the friends I have. And I still have to remind myself to put the phone away. Trust me, I'm not perfect at this, but I've really tried to create some hard and fast rules, especially while my kids are still young, to make sure that they know I'm there, I'm engaged, creating those core memories.

1:13:10And I just know none of this is for anything else other than the legacy I'm leaving them with. Hopefully time well spent and a dad who's got a job that he cares about and a job with purpose. I want them to see me working. I don't want them to see me not. And I frankly, I don't think I'd last too long just sitting around. Like I said, it's all thanks to her. And as I've gotten to know other folks who have gone through similar things, it's been eye-opening too, to see this is a recurring pattern. And so every bit that I can do to try to make that time count with my close friends, my loved ones is hopefully honoring that.

1:13:43Alexis, thanks so much for sharing your story and this exciting path around with 776. I'm listening to a few of your pods. They're not normally this heavy and philosophical, man, but I'm glad I can do it. Thanks, bud. Thanks for listening to the show. To learn more, hop on our website at capitalallocators.com, where you can join our mailing list, access past shows, learn about our gatherings, and sign up for premium content, including podcast transcripts, my investment portfolio, and a lot more. Have a good one, and see you next time.

1:14:25Thank you.