Alex Rampell on TBPN: Revenge, Redemption, and Founder Drive

a16z General Partner Alex Rampell joined the Technology Brothers Podcast Network following the announcement of Andreessen Horowitz’s new fund to discuss what drives founders to build enduring companies. Drawing on his journey from early software entrepreneur to leading a16z’s apps fund, Alex shared how high agency, deep historical understanding, and the ability to attract talent, capital, and customers separate great founders from the rest. He reflected on motivation beyond money, explaining why “revenge or redemption” often fuels the resilience required to push through the hardest moments of company building.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Alex Rampell?

  You either want revenge or redemption. And some of the best entrepreneurs have this in common. And you see this with some of the best entrepreneurs. Like, what is the driving motivation? These are all industries that I wouldn't say they've been untouched by software. They've been untouched by specialty software. And the reason why is because the market was perceived to be too small. That's the really hard thing to disambiguate today, which is you can have things grow so quickly, but they can also go to zero so quickly because anybody can build software in like a weekend, which is both great and terrifying at the same time.

• 0:33Erik Torenberg?

  Today's episode is a conversation with Alex Rampell on TDPN following the announcement of A16Z's new fund. In this discussion, Alex reflects on his path from early software entrepreneur to leading A16Z's apps fund and how those experiences shape the way he evaluates founders today. He shares what he looks for in exceptional builders, including high agency, deep knowledge of category history, and the ability to materialize talent, capital, and customers, as well as why motivation beyond money, what he calls revenge or redemption, often determines who endures. They also get into how Alex is thinking about the application layer in an AI-driven market, from greenfield opportunities and labor-replacing software to proprietary data votes, and why compressing timelines are raising the bar for defensibility, distribution, and long-term advantage.

• 1:21Speaker 02

  What a day. Congratulations. How are you doing?

• 1:24Alex Rampell?

  Good, good.

• 1:25Speaker 02

  Fantastic.

• 1:26Speaker 03

  Super excited to have you on. I've enjoyed, you're somebody who's, I've read your writing and listened to your podcast appearances for a decade now and always appreciated your point of view on a bunch of different things. So, welcome to the show.

• 1:44Speaker 02

  Yeah.

• 1:45Alex Rampell?

  Thank you. Yeah, I'm here to prove that I'm real.

• 1:47Speaker 02

  Fantastic.

• 1:48Alex Rampell?

  It's like proof of life is very important increasingly, right?

• 1:51Speaker 03

  Yeah, it is.

• 1:53Speaker 02

  I mean, first time on the show, can you give us a little bit of backstory, the journey to Andreessen and how long you've been there?

• 2:00Alex Rampell?

  Sure. So, I've been here for 10 years. Previously, been a long time on...

• 2:07Alex Rampell?

  Previously, a longtime entrepreneur. Started by writing software when I was a kid in high school, actually even before that. And then out of college, I was like, I graduated in 2003. I was probably the only person in my class that just kind of became an entrepreneur right away. And it wasn't because I was smart or dumb, probably more dumb than smart. It's like I had a little business that I was running in college. So I kind of kept doing that. Met this guy named Chris Dixon, who was at Harvard Business School when I was at Harvard College. You have to remember like 2002 when we met, the internet 1.0 had just died. Everybody lost their jobs. September 11th, it happened. And what do you do if you're a dried up entrepreneur? You go to business school. I remember this company called Cosmo.com, a huge hit that kind of went from zero. What did that guy do? He went to HBS.

• 2:52Speaker 02

  No way.

• 2:53Alex Rampell?

  So Chris Dixon was there and he and I were like the only two people, I swear, in like the entire state of Massachusetts that thought that the internet was still kind of cool. We got introduced by a mutual friend, had coffee at Aubon Pan, this little East Coast chain, and then cooked up a product called Did They Read It?, which is still around today. It's an email tracking tool that embeds a tracking pixel in every email that you send out. That did pretty well. Then we started a venture-backed company together that became Site Advisor. That got acquired. And then I started another company called TrialPay. Like the thing that we learned at Site Advisor is that nobody likes paying for software. Like you're willing to pay for an intangible good, like a glass of wine, $20 for that seems totally reasonable, right?

• 3:34Alex Rampell?

  But paying $20 for one song on iTunes, there would be riots in the streets. So the idea was, I'll give you this digital good for free if you buy something else. And if you know how affiliate marketing works, it kind of plugged into that. So it's like, hey, we'll give you this product for free if you sign up for Netflix, or if you switch to Geico, or if you shop at The Gap, or if you get a Discover card, using the affiliate commission to go pay for the product. That did pretty well. Like it was like half of the revenue of Site Advisor. It was like for my little shareware business that I used to have back in the day, it doubled our revenue. So I turned that into a company called TrialPay. That did great for a while, then it did terribly, then it kind of resumed to okay, sold it to Visa. And then along the way, met this guy Max Levchin, after he had sold Slide to Google, and we

• 4:18Alex Rampell?

  cooked up a company called Affirm. So I co-founded Affirm with Max in 2012, and actually brought Affirm to Andreessen Horowitz as a funding opportunity, which they did. And Chris Dixon kind of ended up talking me into joining here in 2015. So I've been here ever since.

• 4:37Speaker 03

  How quickly did you realize that Chris and Max were special? Because I imagine during those two periods, you were meeting hundreds of different people. I'm sure people wanted to build stuff with you, other entrepreneurs. And you picked well, back to back. And it's probably the hardest, one of the hardest things to actually clock at times.

• 5:01Alex Rampell?

  Yeah, I mean, I think a lot of the greatest people, they have two things in common. They have this term that's going around a lot, like high agency. Like they don't just like follow the rules. They just like take matters into their own hands and do something. And then they just kind of know the history of everything before. Like they're just like students of history, philosophy. Like, you know, Chris was a philosophy major. People don't know about him. He went to, like, he went to, you know, he got his bachelor's degree in philosophy, was going to do a PhD. He kind of realized that was a bad idea. And then eventually went to business school, which was, he will probably say the worst idea. But it was kind of self evident. I mean, Chris and I, I mean,

• 5:36Speaker 03

  The history, the history thing's a real thing. Like, if you're talking to an entrepreneur that has been building their business for one to two years, and you can tell them companies that in somewhat recent history, in the last decade even, that have like attempted that, or companies that are adjacent, and they're like, oh, I'm not familiar with that. It's like immediately like such a bear signal.

• 5:54Alex Rampell?

  Oh, it's a red flag. Well, the opposite, like, that's the red flag. The whatever the opposite. Green flag.

• 5:58Speaker 03

  Yeah, that's what I'm saying. But yeah, the green flag is,

• 6:03Alex Rampell?

  Never white flag. What's the green flag? The green flag is not only do I know everything. I mean, I'll give you one example. I think the Collison brothers went out to like D. Hawks Ranch. Like D. Hawks started Visa. He's kind of like a weird quasi-communist, even though he started one of the biggest companies in the world. Because Visa was meant to be this like, it was a nonprofit. Visa was a nonprofit until 20, I don't know, 2008, maybe 2009. It was the biggest IPO. Yeah.

• 6:29Speaker 02

  That's right.

• 6:30Alex Rampell?

  Yeah, but it was a nonprofit until then. A nonprofit like the NFL is a nonprofit. It like makes a lot of money, but it's owned by the constituents. And the constituents that own Visa were the banks. And it's like, okay, I'm starting a payment company. There were a lot of payment companies that came before, but it's like, who will? Let's find this guy who's 90 years old, who's moved outside of capitalism, is working as a farmer just to learn from him. And like I have this mental model that I now use for entrepreneurs, and it's a memo that I've written that we use internally a lot. I gotta say, like, the best entrepreneurs, they have five things that I look for. They can materialize labor, capital, and customers, and hopefully those are self-evident. It's like you can get people to quit their high-paying job for like certain failure. It's like the Ernest Shackleton thing. It's like you wanted men for Dangerous Journey, almost certain failure and death, but if it worked, you might be famous, right? It's like you want that.

• 7:15Alex Rampell?

  Very, very hard to do. You have to find people that can materialize capital. It's like get people to give you money. And the best, the best sign of future fundraising success, like if we do round N, we want to make sure there's going to be a round N plus one, or you're going to be profitable on round N, which is unlikely. So are you good at fundraising? Can you get customers? Like imagine, it's like, I have two weeks of cash left. Please be my first customer. I have none. Like, who? It's very hard to pull that off.

• 7:37Speaker 02

  Yeah.

• 7:38Alex Rampell?

  Then you want to know the history of the space, which is super important to your point. You want that green flag version, not just the intermediate, you know, what's the, what's the, the combination of green and red flag like the

• 7:48Speaker 02

  Brown?

• 7:48Alex Rampell?

  The tur- you don't want the turquoise or the whatever. Like you, you want the green flag. This person knows everything that's tried before, and they have a new angle of attack. They're not going to learn on the job. They've actually learned through history. And then the last thing that I care about a lot, everybody in my, my team knows this. My favorite book is The Count of Monte Cristo by Alexander Dumas. And it documents the story of this guy, Edmond Dantes, who's like wrongfully accused, is like in prison for 17 years, but then becomes the richest person in the world, but doesn't give a shit. Right? It's like, all the, all the riches in the world do not matter. He wants revenge.

• 8:19Speaker 02

  Yeah.

• 8:20Alex Rampell?

  Right? You want, or so you could either, revenge kind of sounds bad. It's like a testimony, but you either want revenge or redemption. And some of the best entrepreneurs have this in common. And the reason why it's so important from a venture lens is imagine that you're a 20 year old kid, you start a company, and somebody offers you, I don't know, half a billion dollars to buy your company. And you own 25% of it. You're going to make over a hundred million dollars. You'd have to be insane to turn that down. Right?

• 8:44Speaker 02

  Yeah.

• 8:45Alex Rampell?

  And we need people that are insane, that that actually are going for it. It's not that we don't want people that aren't capitalists that don't care about money. But it's like, they care about if you've seen the movie Spaceballs. It's like, we're not doing this for the money. We're doing it for a shitload of money. A little, a little different here. It's, I'm doing it for another reason. And like, a great example of this is there's this guy, René La Plante, who started a company called Lending Club.

• 9:05Speaker 02

  Oh, yeah.

• 9:05Alex Rampell?

  Um, very famous company at the time. There was like a dearth of IPOs, like Lending Club kind of gets to scale, goes public. He gets fired from his board, ousted from the company. He's probably made hundreds of millions of dollars. He's the Count of Monte Cristo. He's like, you know, fuck those guys. I'm going to start a new company. I'm gonna, I'm gonna start an upgrade. And you know what he called his new company? Upgrade. It does the exact same thing as Lending Club. It's probably 10 times the size of Lending Club now. And what's motivating him is not just the, hopefully, you know, shit ton of money, Spaceballs quote. But he wants revenge.

• 9:36Speaker 02

  Yeah.

• 9:36Alex Rampell?

  He wants redemption. And you see this with some of the best entrepreneurs, like, what is the driving motivation? And because when times get tough, like, you need something, because like, there is no money. Like, if, if your company's going to zero, uh, if you're Ernest Shackleton in the winter of Antarctica, like, your voyage is not successful, right? You, you need something else driving you at that point. And that's why that, that metal is something that, that I, I find extremely valuable.

• 10:04Speaker 02

  Have you seen Spaceballs, Jordy?

• 10:05Speaker 03

  I have not.

• 10:06Speaker 02

  You got to.

• 10:07Speaker 03

  I famously, I famously, I famously have seen like, 110 movies.

• 10:10Speaker 02

  He's not a spaceball, no. Nice question.

• 10:13Speaker 03

  One of my, uh, probably like a, I really, I was gonna say, maybe, I, it's hard to exactly place a top 10. Like, I, I loved your episode on, uh, Invest Like the Best, on operating systems. How is AI kind of like updating your thinking on moats and operating systems? And, uh, how somebody can create a lot of value with a startup?

• 10:35Alex Rampell?

  Yeah, well, I think, well, maybe I can rewind a little bit and just because we announced this new fundraiser, I can tell you exactly what we told our LPs in terms of like what we want to invest in at the application layer, because I do application layer stuff. And it's really three things, you know, category one is, I call it greenfield bingo. And kind of maybe another way of answering your question is, there's something that there's a quote that I use a lot, the best companies have hostages, not customers. Right? Like, that's why nobody likes using Salesforce. You gotta be taking revenge. You gotta be taking hostages. You know, it's very Old Testament stuff. The best companies have hostages, not customers. Those are great companies to invest in, right? And that kind of goes to the part that I

• 11:17Alex Rampell?

  was making, like, you know, NetSuite, Workday, Salesforce, like, they're all hated by their customers, but none of those customers can leave. However, if you build a better version, like, kind of a more AI-first version of all of these companies, and you're selling into the greenfield, you've got a shot, right? Because, like, I was lucky enough to be the first investor in Mercury, and Mercury worked not by stealing people from SVB. They just worked, it's like, oh, you're a brand new company, you can use shitty SVB, or you can use really good Mercury. And that worked. Whereas, they never got customers from SVB until the weekend that SVB failed. So that greenfield opportunity for software, like, that is AI-enabled, in the same way that, like, that was true for cloud, right? That

• 11:59Alex Rampell?

  was true for Volvo. It's like, here is the new thing, the incumbent will eventually build it. Like, another expression that I use a lot is, like, the battle between every startup and incumbent is whether the startup gets the distribution before the incumbent gets the innovation. The incumbent, my default assumption is that the incumbent normally wins. Because they have the distribution, they will get their act together three years later. And with AI and cursor and everything else, they'll get their act together maybe three weeks later. So the, the, the kind of... The might of distribution is very, very powerful. So one option is you just go into the greenfield. So that's kind of category one is, you know, we call it greenfield bingo. It's just like build, we have a bet that's just like NetSuite. It's better, it's AI enabled, but they're not going to steal customers from NetSuite. They're just going to get greenfield.

• 12:43Alex Rampell?

  Category two is this kind of new, super exciting category of software does labor. And like, there is no incumbent software product for, I don't know, trial attorneys. Like, it's called Microsoft Office, but like Eve does that and does that really well. There's no incumbent software product for dental office receptionists, but Tenor does that and does that very well. So that's a really, these are all industries that I wouldn't say they've been untouched by software. They've been untouched by specialty software. And the reason why is because the market was perceived to be too small. And this is exactly what happened to SaaS. Like fintech really changed SaaS significantly because take, I'm sure you've heard of Toast. Toast is one of my favorite businesses.

• 13:27Alex Rampell?

  It's like Square, but it's only for restaurants. It's this whole operating system for restaurants. How many restaurants on their IBM PC Junior in 1984 use software? Like, zero. And how many of them would pay tens of thousands of dollars a year for software? Zero. But they all need payment processing, they all need payroll, they need these other services. You kind of bundle them in with software. And this is the really exciting thing about AI is you go say, hey, trial attorney, I want you to pay $50,000 a year for software. You said this 10 years ago, like, no way. Like, we'll pay for Microsoft Word because we use it to write demand letters. Like, that's it. And now you can say, hey, we'll handle all these cases for you that you could not handle profitably, and that's AI plus software. Now they are software buyers. So that's category two.

• 14:11Alex Rampell?

  And then category three, I call the walled garden. And I wrote a post about this a little while ago, but walled garden businesses are amazing because if you assume that in the world that we live in today, and this is another way of thinking about kind of defensibility in AI.

• 14:27Alex Rampell?

  OpenAI has their sights kind of on everything, right? Like Anthropic probably has their sights on everything. It's so easy to build everything. So I'm the, have you guys heard of open evidence?

• 14:35Speaker 03

  Yeah. Yeah.

• 14:37Alex Rampell?

  Okay, so I tore my Achilles in February. It's almost a year ago. It sucks, right? It's all better now.

• 14:43Speaker 03

  Doing something fun?

• 14:45Alex Rampell?

  It was, I was skiing in Japan.

• 14:46Speaker 03

  There we go. That's a good reason, that's a good reason.

• 14:49Alex Rampell?

  There we go, there we go. Tear my Achilles, what do I do? So I go to ChatGPT. I'm in like the clinic in Nisoko, Japan, talking to the Scottish doctor and he tells me, oh yeah, you only have surgery in the US. Nobody does it outside the US. I was like, this guy's on crack. Like, of course you have surgery to fix an Achilles. I go to ChatGPT, it tells me everything. Then I think, I find this thing, open evidence, and it's like ChatGPT, but it has every single medical document in the world. And imagine that tomorrow, ChatGPT 5.3 comes out, it's AGI, everybody agrees it's AGI, human race is over, but it has no medical data. And then on the other side, you have GPT 3.5, and it has every single piece of medical knowledge ever known to mankind. What would you rather use? And the answer, at least for me, and I did use this, is open evidence.

• 15:34Alex Rampell?

  So there's so many businesses that look like this, where they find some proprietary piece of data. They're the only ones that have, because before you would have to sell data. That was like your only, that was your only hope as a business. And like another example that I mentioned in this post, there's a company called Vlex. And Vlex is this like 25-year-old European data business that bought up, you know, legal records in Spain to start, and they would sell it to firms like Wilson Sonsini that needed it for case law. Now they sell an outcome, because they're the only ones that have all the records. So you can chart, you can build a really interesting business if you're the only source of some unique form of data. And I love businesses like that, because that's the other, sorry for being so long-winded

• 16:16Alex Rampell?

  here on the answer to your question, but the businesses that can be very, very large in AI, that can grow very, very quickly, you still need to make sure that they're fundamentally defensible. And that's the really hard thing to disambiguate today, which is you can have things grow so quickly, but they can also go to zero so quickly, because anybody can build software in like a weekend, which is both great and terrifying at the same time.

• 16:39Speaker 02

  Yeah, indeed. Well, thank you so much for hopping on the show and breaking it down.

• 16:43Speaker 03

  Incredible overview.

• 16:44Speaker 02

  Yeah.

• 16:45Alex Rampell?

  Thanks, guys.

• 16:46Speaker 03

  Yeah, great to meet you.

• 16:49Erik Torenberg?

  Thanks for listening to this episode of the A16Z Podcast. If you liked this episode, be sure to like, comment, subscribe, leave us a rating or review, and share it with your friends and family. For more episodes, go to YouTube, Apple Podcasts, and Spotify. Follow us on X at A16Z and subscribe to our Substack at A16Z.substack.com. Thanks again for listening, and I'll see you in the next episode. This information is for educational purposes only and is not a recommendation to buy, hold, or sell any investment or financial product. This podcast has been produced by a third party and may include paid promotional advertisements, other company references, and individuals unaffiliated with A16Z. Such advertisements, companies, and individuals are not endorsed by AH Capital Management,

• 17:33Erik Torenberg?

  LLC, A16Z, or any of its affiliates. Information is from sources deemed reliable on the date of publication, but A16Z does not guarantee its accuracy.