The Exchanges

Q Why don't you take me all the way back to your first entrepreneurial instincts as a kid?

A Gosh. Well, my first would have been mowing lawns around the neighborhood. This was now in suburban Maryland. And as soon as I could push that mower, my dad would pay me an allowance, probably a few bucks to mow the lawn, and I realized my neighbors would pay me more. Sorry, dad. Shout out to the fields. They were across the street. The mooths, also across the street. We did some business, so I mowed a lot of lawns. That was really the start of it. Then I went and got a job at CompUSA when I was 14. And I had this Madonna mic, and I'd be pitching the latest computer peripherals and software to a crowd of people who did not want to hear a fourteen-year-old telling them about a computer mouse. So I went through the worst public experience hell every 30 minutes as people just ignored me, and I'd be like, it's my job to present this mouse to you from Logitech. And I got over so many of my inhibitions around public speaking. That was an amazing job. And I was making websites for strangers on the internet for money, so I was doing that while I was in high school, so I always had a lot of ambition, even at a young age, to just be my own boss and solve people's problems.

AI assessment note: “my first would have been mowing lawns around the neighborhood.”

Q How did you think about what to do as you went through college?

A I entered UVA, Wahoo Wah, as a pre-med, I think that's what it says in the first year lookbook, and I bopped out of that within a week, and I was looking for a replacement. And I found this ancient Greek history class, which is relevant now because seven, seven, six is named after the first Olympic games. I took this class. I love this ancient Greek history class so much. I declared my history major first semester, first year, and the dean of the history department was shocked that a freshman would come in there after one semester declaring, but I was convinced I was going to study history. I ultimately double majored and also got an undergrad degree in business from McIntyre. But I was going to be a lawyer, because that was what a history major does, and my grandfather was one, and I thought I could do this too, and then I walked out of an LSAT, because I was hungry on Saturday morning to go get a waffle from Waffle House, and then as a true story, 20 minutes in, I just got up and left, and after months of studying for this test, I was just too hungry, and realized sitting Eating my waffle that I probably should not be a lawyer if I wasn't going to take the LSAT seriously. And that's where I decided I was going to engineer something to do after graduation, and that ultimately led to Reddit. And shout out to my friend, Walt Eamer, who's the CEO of Waffle House. He put a plaque …

AI assessment note: “I entered UVA... as a pre-med... declared my history major... ultimately led to Reddit”

Q So how did you turn from building up Reddit, selling it, spending some time at Connie Nast to investing?

A Paul and Jessica, again, shout out, had invited me to I think it was in 2010. Once the handcuffs came off with Reddit, they invited me to come out and play a role at YC, and I wasn't ready to move. I was living in New York. I love New York. I was born in Brooklyn, but they engineered a role for me as this ambassador for the firm. So then part-time partner, then full-time partner, and I eventually started moving my way out west. But that was when I first got under the hood on the other side of the table at Combinator, starting to see thousands of applicants every six months, reviewing them, Interviewing founders, accepting them, working with them. I didn't fully appreciate just how big YC was becoming in terms of its impact on the ecosystem, because Reddit was such an early small exit, but it was the first validating one of that first batch. This ten million dollar exit was the first really big one for YC, and it helped give a seal of approval that then led to Dropbox supplying, which was the first real billion dollar company, and then that led to Airbnb. Once you did it twice, it really validated YC as a model, and so getting to see that from the inside was eye-opening. Paul Graham had built just a little bit of software to manage office hours and applications, and it was just enough, and I think in part because of Paul's distaste for management and people. He built the softwar…

AI assessment note: “they invited me to come out and play a role at YC”

Q So what was that initial origin story of Reddit?

A It was a way to order food from your cell phone via text message. And so this was 2004. Now I graduated in O five. So there were no smartphones. This is era of the candy bar phone or like the Motorola razor. I think it just come out at that time, radical new flip phone. And having worked at pizza through college, I was a cook for a brief period there. And so I was used to these orders coming in through a printer and And they'd come from the front as the servers would input them on a touchscreen, but I realized, okay, well, the output's just a printer. Like, you could come up with another input, and my roommate at the time had been visiting, I think it was Sheets Gas Station, where they had touchscreens to order your subs while you're pumping your gas. Felt similarly, like, hey, I could just use my phone. And so we didn't have a good tech solution for this, because the interface, in hindsight, would have been just heinous to try to text in, but I I talked to every restaurant on the corner, which was the main strip in UVA of bars and restaurants. They all of course wanted to be nice and said, oh yeah, great idea. At the time I was so naive. I thought that counted as business development. I thought like, I'm being a good CEO. I've got customers. That was dumb. And what it took was my roommate who I'd recruited at this point, Steve to now join my company. And then his then girlfrie…

AI assessment note: “It was a way to order food from your cell phone via text message.”

Q How did you think about building an audience?

A It was grueling. In oh five, there were no social media websites. So remember, this is before Twitter, before LinkedIn. The extent of it was Facebook, which was still in colleges. MySpace friends still were already on the decline and blogs were actually the dominant UGC user generated content of the time. So building an audience involved me cold emailing a ton of bloggers to say, hey, look, I'm Alexis Ohanian. I found this company, Reddit. We think we have an interesting approach to helping people find what's doing interesting online. You may want to submit some of your articles there. Maybe some of your fans already have. That was even better when I could find one of their articles that did well that someone had submitted. It's a great way to open an email, which is like, hey, 50 people have upvoted your link on Reddit. Now they didn't know what the hell that was, but it felt nice. And Basically try to get them to do an interview with me about Reddit. You know, five, oh six, you'll see all these random bloggers who have written articles about Reddit. And this was the main way we would appeal to them and the way we would grow the fan base. I had run a forum, a PHP BB forum in college, probably had about 607 hundred members. Those were the first people I emailed to say, hey, try this new thing out. Reddit in a lot of ways is just modernized forum software. And we got some early …

AI assessment note: “building an audience involved me cold emailing a ton of bloggers”

Q I'd love to ask you about one of your investments on that other side of the barbell. Brent 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?

A 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-worn 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 Except now in the late teens. And I was shocked. I 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 sort of 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. And 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…

AI assessment note: “he knew sort of what I would call top-down... And then I knew the bottom up UGC”

Q So when you step back into Reddit a number of years later, what was the platform at that time?

A Well, the previous CEO, it just defended revenge porn a few months earlier. In the name of free speech, and that was one of his last acts as CEO. Not surprisingly, one of the first things that happened after I came back was banning revenge porn, which was a pretty obvious thing to do, but it was a company that had, I think, eight million dollars in revenue that year, 2014, that's public, despite being over a decade old, and dropping, because obviously advertisers don't want to be on revenge porn websites, and so maybe 40, 45 employees, no mobile app, Which was gut-wrenching, because I designed and shipped an iOS app in 2009. It was called iReddit, and it's supposed to be Reddit on Reddit, like iReddit on Reddit. That's why I named it Reddit. And so I shipped this iOS app, but then I left six months later, a year later, and so it died. And it killed me because here I was five years later, we still didn't have a true iOS Reddit app. And unfortunately, the culture had metastasized around this idea that desktop web was the only thing that mattered, which was sad because even in 2014, it was obvious that mobile was here to stay. So it was a lot of product to catch up on, a lot of business to rebuild, and a team to rejuvenate. And I was very lucky about a year later, we're about 60, 65 people at this point, hired Caitlin Holloway as our first ever head of people and culture, and she …

AI assessment note: “eight million dollars in revenue that year, 2014... maybe 40, 45 employees, no mobile app”

Q So 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?

A I have done a terrible job building my audience, and I know you're gonna 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, Ted. It's a lot. And if you want to do it well, you got to do the work. You got to get the reps in. And 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 I 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. Let 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, W…

AI assessment note: “I've built more and more software to help us do this better, cheaper, faster.”

Q What did you learn about giving feedback effectively?

A Really great feedback is fast. It happens pretty quickly after some incident. It is direct, and it is compassionate. Ideally, create a culture and create an environment where you're attracting the kind of folks who are going to thrive with feedback. The good news is, In many high performance cultures, there's a high correlation between folks who are high performers and who love feedback, especially this kind of feedback when delivered well, because they want to get better. They are endlessly searching self-improvement. And so if you can first and foremost, try to build a culture that attracts that, then, okay, you're delivering it in a timely manner that is compassionate. It's not hateful and also is very specific and speaks to the actions or the things or the work that needed to improve. And bonus 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.

AI assessment note: “Really great feedback is fast. It happens pretty quickly after some incident. It is direct”

Q What were those one or two key lessons you learned about management?

A Oh, number one, and this is something we'll coach CEOs on now. If there are really systemic challenges with an employee, and you give that direct feedback, and you don't see material improvements, and you keep going through the same process quarter after quarter after quarter, it's not actually going to get better. You've got about six months really to get them ramped up, moving, see the full output. And if things aren't hitting expectations, it could be because maybe you leveled them and properly and they're not quite the right role, but if they are struggling in key ways and you give them that feedback and you give them another quarter to work on it and you don't see enough change after another quarter, it's basically time to make the move. And that is one of the hardest things in the early days of a company. So much of your success comes down to the team that you build. And one of the hardest things first time founders and CEOs have is around performance management. Whether that's giving negative feedback, which is also a gift if done well and really important, but then also moving on from folks and doing separations. And those are muscles you have to exercise in the gym. You cannot just read about, and hopefully you've got good partners around. You can help you think through this stuff, role play this stuff and whatnot. And this is something we try to provide for founders o…

AI assessment note: “it's basically time to make the move. And that is one of the hardest things”

Q 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.

A The 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 nineties 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 a 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. The 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. And 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 lo…

AI assessment note: “So it wasn't something we thought about from the jump.”

Q Which two people have had the biggest impact on your professional life?

A I'll say Caitlin Holloway, who I've worked with now almost a decade since the Reddit turnaround now is seven, seven, six, and this is gonna 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 seven, seven, six 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, and 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 twenty million in climate grants that I've been putting out every year. We take open applications all over the world. It's like 20 young people, give them a 100,000 dollars each and just 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 nother generation of entrepreneurs do great things to help m…

AI assessment note: “I'll say Caitlin Holloway... and Paul Tudor Jones has really been just awesome”

Q When you're talking about sports, I just have to ask you, what have you learned from your wife?

A What have I learned? Well, it goes without saying, I wouldn't have tweeted that prophetic tweet in 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. But 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, like, this sport is way harder than I thought it was, and way more exciting, and I didn't even watch a men's match for a year, and 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. Statistically, 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 wa…

AI assessment note: “I wouldn't have tweeted that prophetic tweet in That women's tennis in America was”

Q And what have you seen about how that transcendent excellence in sports translates to day-to-day life?

A It'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. Like, 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. She 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. The 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. She always had to be a little better in order to keep up with her…

AI assessment note: “she applies that whether or not she's making cinnamon rolls for the family”

Q why customers call it miraculous, game-changing, and an awakening. If that's not how you would describe your investment management tech, request a demo at ridgeline.ai. 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?

A 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. And so as a result, I have a really broad network. You gotta imagine being a first check in companies ranging from Coinbase and Instacart to Patreon and Roe 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, and 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. You know, 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 t…

AI assessment note: “We are generalists, and so I think I've benefited through my entire investing career”

Q There'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 the sort of conviction and ideas. And then the last is founders. Maybe just start with this question of the idea and the founder, and how do you think about the intersection of the two?

A 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. So 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 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 the 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, but 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 2…

AI assessment note: “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.”