Ben Horowitz - Backing America’s Future - [Invest Like the Best, EP.457]

My guest today is Ben Horowitz, the co-founder of Andreessen Horowitz. Since its founding in 2009, a16z has grown into one of the most influential firms in venture capital, reshaping how technology companies are funded and how power and ideas move through Silicon Valley and around the world. This conversation focuses on sides of Ben’s story you don’t often hear. Ben reflects on the people who shaped him, including Nas, Andy Grove, and his father, and shares why he chose to personally fund new technology for the Las Vegas Police Department. We also talk about how he thinks about a16z’s responsibility in shaping the trajectory of America, the scale of his ambition for the firm, and what he sees as the biggest risk facing the country. Please enjoy this great and unique conversation with Ben Horowitz. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest. ----- ⁠Rogo⁠ is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps (00:00:00) Welcome to Invest Like the Best (00:02:43) Episode Intro: Ben Horowitz (00:03:27) The State of America Right Now (00:06:06) How Policy Could Destroy America (00:08:29) AI Changes the Laws of Company Building and Investing (00:11:40) Why AI Researchers are Paid $100M (00:13:16) Thoughts on Growing Inequality (00:18:07) Societal Challenges Due to AI (00:19:56) Ben’s Scope of Ambition for the Next 20 Years (00:22:48) Andy Grove’s Influence on Ben (00:27:44) Starting Andreessen Horowitz (00:32:53) Early Mistakes (00:36:17) What Capital Markets Are Missing (00:37:44) Why VC and Not PE (00:40:03) Tradeoffs with Scale (00:41:10) A Culture is Not a Set of Ideas, it’s a Set of Actions (00:43:05) Lessons from His Father (00:45:03) Exciting Use Cases of AI (00:46:46) Ben’s Friendship with Nas (00:50:05) Funding New Technology for the Las Vegas Police Department (00:54:07) The Kindest Thing

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

• 0:01Patrick O'Shaughnessy?

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• 0:42Patrick O'Shaughnessy?

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• 1:30Patrick O'Shaughnessy?

  Hello and welcome, everyone. I'm Patrick O'Neal, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. If you enjoy these conversations and want to go deeper, check out Colossus, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus, along with all of our podcasts, at colossus.com.

• 1:54Speaker 01

  Patrick O'Neal is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.

• 2:22Patrick O'Shaughnessy?

  My guest today is Ben Horowitz, the co-founder of Andreessen Horowitz. Since its founding in 2009, A16Z has grown into one of the most influential firms in venture capital, reshaping how technology companies are funded and how power and ideas move through Silicon Valley and around the world. This conversation focuses on sides of Ben's stories you don't often hear. Ben reflects on the state of America, the people who shaped him, including Nas, Andy Grove, and his father, and shares why he chose to personally fund new technology for the Las Vegas Police Department. We also talk about how he thinks about A16Z's responsibility in shaping the trajectory of America, the scale of his ambition for the firm, and what he sees as the biggest risk factor facing the country. Please enjoy this great conversation with Ben Horowitz.

• 3:06Patrick O'Shaughnessy?

  I think a fun place to begin, Ben, would be your take on the state of the country. What does it feel like to you in 2026? I know part of your mission is to directly impact the trajectory of the country. We'll talk about that a lot. But begin with, what does the landscape, the playing field, feel like to you today?

• 3:22Speaker 02

  I think the tech sector is very, very healthy. America's competitiveness is very, very good. The entrepreneurship culture is outstanding. And that's the main thing I look at from my lens. If you look at, and I go kind of all over the world, and everybody wants Silicon Valley. Like, how can we have Silicon Valley in the UK? How can we have it in France? So they have a lot of the ingredients, right? They have great talent. They've got great universities. They have like a definitely a worse regulatory environment and EU increasingly bad regulatory environment for entrepreneurship. But there's a cultural challenge where succeeding, doing something larger than yourself, making the world a better place, like, those aren't things that young people feel like society values.

• 4:06Speaker 02

  And so the likelihood, if you're building a company, of getting people to work for you and dedicate their life to a mission like that is just not that great. Whereas in the US, it's amazing. I think the economy is in much better shape than people realize. We've done a lot of kind of things to stimulate it. We've got lower energy prices. We've got much less regulation. We've got more user-friendly tax code. And that's all starting to kick in now. From our perspective, I think the bigger thing is AI is going to impact everything. There's almost no problem you can think of that you can't go, well, we have a real shot at solving that with AI. What were the big problems in the US? Autodesk, well, we got an AI solution for that.

• 4:50Speaker 02

  Cancer, we have an AI solution for that. The fact that we've got a technology where we can address everything is a real new phenomenon. And all that's, I think, going to kick in like in a fairly major way over the next 12 to 24 months.

• 5:06Patrick O'Shaughnessy?

  Why do you think 12, 24 months is a timeframe worth mentioning? That some of this stuff will start to be felt more broadly?

• 5:12Speaker 02

  It's all starting to take effect now. You know, it's got to roll out, get deployed. Deployments of technology in particular in the past have taken a long time, but you had to build out the infrastructure to do it. For cars, you needed things like roads, traffic lights and all that kind of thing. And for the internet, you needed fiber in the ground and people to have smartphones. And you needed to do a lot just to get going. The internet is here, so if you want to use AI, if you want to apply it to your business, you just do it. There is no infrastructure that needs to be built to adopt the thing.

• 5:45Patrick O'Shaughnessy?

  What could most interrupt this good trajectory that America is on? Where we are building solutions using technology? Like, what are the biggest risks?

• 5:54Speaker 02

  Policy. One of the things my father said, a bad government, no matter how many smart people you have, no matter how great a culture you have, no matter how great the country is, can ruin the whole thing. Venezuela was the fourth richest country in the world. And then communism, and that's that. If you look at how little comes out of so many of these countries in Europe that have so many smart people and then, you know, and then the ones that went into communism, and there's so many genius Romanian entrepreneurs. John von Neumann and the number of great genius scientists that came out of Hungary, like this little country, and then it was just gone once the communists took over is

• 6:34Speaker 02

  completely like nothing, from inventing everything to nothing overnight. And I think that that can absolutely happen here. We could outlaw AI. There were like pretty aggressive proposals. The last Biden administration executive order said that you could not sell a GPU without federal government approval. That was a real executive order and it got reversed. But like, we were that close to being basically out of the global chip game. It is fragile. Technology solutions work much better than policy solutions. That's the other thing. Like, policy solutions is very hard to make anything work. So if you think about COVID, we could tell everybody to stay in their house.

• 7:19Speaker 02

  Well, that's got some like extremely bad side effects. Turned out not to work that well. Or we could invent a drug that cures it, or like a vaccine that works. It's just hard to have a policy solution like, you know, all the policy stuff on climate change. And Europe actually reduced emissions and all that, but it didn't do anything because China didn't reduce emissions. But if you build a technology, say, nuclear fission or nuclear fusion facility, that would have a big effect. And I think in general, that's true. Defund the police did not make anybody safer, but technology does. If you really want to change the world, if you really want to make a better place, I think you can build a solution for darn near anything.

• 8:02Speaker 02

  If you want to change the world for the better, it's never been a better time to be an entrepreneur.

• 8:07Patrick O'Shaughnessy?

  I was with a local restaurateur yesterday here in New York, one of the best. For a couple of hours, having him describe to us how he is planning on using AI tooling to improve everything about his restaurant business. How do you think about the way all of this is changing this sort of potentially large, attractive businesses that you want to invest in? Because many great companies that have been built in and around restaurant software businesses. It seems like this restaurant owner is going to be able to have his own spun up operating system specific to him. Not going to need any of that stuff. How is this changing the way in which you view investment opportunities?

• 8:42Speaker 02

  On the positive, everything is up for grabs. I think people are kind of overreacting to that in the stock market and so forth. And that if you like, uh, existing software companies, people think, oh, they're all dead. Well, some of these guys are extremely hard targets. It's not that easy to take out Salesforce or SAP. You would be surprised, even with AI, how much heavy lifting that is. Having said that, It is true that, you know, a lot of these things, you can just make your own. You can do it yourself. It's going to be a lot easier. The number of possible interesting companies, I think, went up a lot. The other thing we're seeing is the products work so much better than any technology products we've seen in the past. Revenue growth is so much faster for these AI companies.

• 9:27Speaker 02

  And there's many such cases of companies coming out. Cursor, which is ostensibly an IDE, like, what's the biggest IDE before Cursor? I don't know, but it wasn't big. And it took probably 12 or 15 years to get to that revenue level. And, you know, they went over a billion dollars in revenue in no time. So that's super interesting. I would say, though, from an investing standpoint, the laws of physics of company building changed, which is going to affect investing in what's currently, I would say, an unknown way. The one thing you knew, if you'd ever built a software company, is you cannot throw money at the problem. What's-a-man-year, 700 IBMers before lunch.

• 10:12Speaker 02

  That phenomenon, everything was built on because you knew if somebody built a great product and it took them three years and they did it with a small team, Google's not going to hire 2,000 engineers and catch them. It's just not going to happen. That was a law of physics. Now, if you have the data and you have enough GPUs, you can solve damn near anything. And kind of we've seen that with Elon catching the big models in no time. He just took a lot of money and a really good data center design and some smart engineers. He got in the game very fast. That would have never happened in the past. The markets are also, seem to be much, much, much bigger than anything we've ever seen.

• 10:56Speaker 02

  It would cause you to think about valuations and kind of long-term value and other sorts of things in a different way than we have in the past. On the one hand, well, when you calculate the long-term value, what if this market wasn't $50 billion? What if it was $5 trillion? On the other end... What if somebody could catch you? These are concepts we've not dealt with.

• 11:18Patrick O'Shaughnessy?

  So how would the conversations feel different to me if I came in? You've got all these great investors working at Andreessen Horowitz. The nature of the conversation amongst your teammates as they're debating this stuff versus four years ago or something, where does it feel most materially different internally?

• 11:33Speaker 02

  I would say one of the most different things is when you look at AI researchers, it is really a different kind of thing. If you haven't been at Google or Facebook or OpenAI or Anthropic, and somebody gave you hundreds of millions of dollars to try and build a giant model and you weren't one of the main people, then you probably don't know how to do it. Because you can't learn it in school. You can't learn it in school because it's a little bit alchemistic in nature. It's a little bit of an art. And so if you've never done it before, the chance of on your very first try of building some kind of large model that it's going to work well, isn't that great? People are coming up to speed more. There's more companies, people are learning it.

• 12:14Speaker 02

  But that's kind of why you got to this, which from the outside world probably looked absolutely bananas. That why is somebody paying $100 million for an AI researcher or $1 billion for an AI researcher? Like, that's the craziest thing I've ever heard. Well, what if there are only 40 of them in the world? Then it kind of changes the math on it a little bit. And I think that's where we were because it's kind of the first time we've had a need for a technologist that academia can produce. That is probably one of the bigger things that changed in the conversation is like, who are all these people? Like, we track all of them and know what they're doing, but it's very different.

• 12:55Patrick O'Shaughnessy?

  Everyone talks in venture about the power law. The thing underneath the power law is a sort of inequality. It seems like so many of the things that are happening are just massive multipliers on the trend of inequality in every way. The billion dollar researcher, the size of the biggest companies, the wealth of the people creating those companies. I would argue that inequality is a feature, not a bug of the American system. But I'm curious for you to riff on like the nature of growing inequality and the good and the bad associated with that.

• 13:25Speaker 02

  What's happening in AI is, I would just say, an extension of the Kobe Bryant effect, which is, you know, a basketball player. There was a limited amount of money you could make because you basically played the game in front of the people who could show up for the game. And that was it. That's a whole market. Whereas, once you had television and a global audience and these kinds of things, you can be LeBron James, you can become a billionaire. And that was not at all possible before. And I think that we kind of first saw that with the internet where, okay, now I can build a product, I can get to global distribution very fast, then all of a sudden I can become like extremely rich.

• 14:03Speaker 02

  And then AI is another layer on top of that in that, okay, now take that same product and make it just more a valuable thing. Whoever invents that is whatever the internet company was, plus, plus, plus. And so that's going to make them even richer. That's the bad part of it. I think the good part of it is it's starting out, day one, completely democratized. Anybody gets access to very powerful AI. Most people in the world at this point have smartphones, and now you've got superintelligence in your phone. So that's a big equalizer of the opportunity in a lot of ways that I don't think we've ever seen a bigger opportunity equalizer than AI.

• 14:48Speaker 02

  Every child can have like a super advanced, amazing tutor, teacher. Great education is accessible to all. So I think it's an equalizing technology and there's some drive in inequality there. This is another thing I learned from my father when I was very young was, he said, look, son, life isn't fair. That's extremely good advice because it's just not going to be fair. No matter what government or anything tries to do, it's not going to be fair. And the problem is if you create a system that tries to correct that, it doesn't make things more fair. It just transfers all the power to the person running the system. And that's what happened with Stalin, that's what happened with Ceausescu, that's what happened with Pol Pot, that's what happened with Mao.

• 15:31Speaker 02

  Not an accident that every single system like that went bad because it really ends up just being a power transfer. When you think about, well, what do you want? You'd like everybody to have a chance. Don't give me no chance. Give me some chance. It may not be as big a chance as the other guy. It may not be a perfect chance. But if I have the desire, if I've got some capability, give me a chance to be something, to make my imprint on the world. A system like that is going to end up with a lot of inequality. By the way, all systems end up with a lot of inequality. But you can try systematically to give everybody an opportunity. I think AI does a really good job of that.

• 16:14Patrick O'Shaughnessy?

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• 16:58Patrick O'Shaughnessy?

  because of how far ahead RidgeLine's AI features are compared to anything else in investment management software. I've been hearing from a lot of investment managers about AI and they fall roughly into two camps, with some unsure where to even start and others convinced that they can build their own order management system over a weekend. The reality is that running an investment firm will always require governance, controls and a single source of truth for your data. And no amount of AI enthusiasm changes that requirement. RidgeLine is built on exactly that foundation, which is why I believe that the firms that come out ahead in the AI era will be the ones running on RidgeLine's unified platform. If you're serious about your firm's AI strategy, RidgeLine should be part of that conversation and you can request a demo at ridgeline.ai.

• 17:42Patrick O'Shaughnessy?

  One of the memes that's very popular today is that you have a couple of years to get some capital, or you're going to be a part of the permanent underclass is the phrase that is used on Twitter. And I certainly agree that now everyone has the best lawyer, accountant, advisor in their pocket, and that's amazing. But what do you think about this notion that because of that, we need less labor? It's going to be harder if you don't have some capital to begin with to accumulate capital and break in. I don't necessarily believe that. I'm just curious what you think about the challenges we'll face because of AI societally.

• 18:12Speaker 02

  I don't really think that's right. I don't think the door is gonna close behind you. I think the opportunities tend to multiply when you kind of open up a new door and open up a new way of doing things. So many people who made money on crypto were like people who literally didn't have much to start with. They just got into the technology early, then they kind of parlayed it up. And so if you have something that grows really fast, that's actually the opportunity for somebody with a little bit of capital to make a lot of money, because it doesn't take much. If you bought Bitcoin for a nickel, you did really well. And all you needed was a nickel. That's the nature of these things that go hyperbolic, and particularly if you create something. I also think the labor market

• 18:55Speaker 02

  stuff, people are acting as though it's very predictable, and when it's not at all predictable. If you look at kind of the history of the world and automation, and this is what it is, it's a kind of like an automation technology. We've been automating things since the agricultural days. And in those days, I think 95 or 96% of all jobs in the US were agriculture. Almost all those jobs have been eliminated. And the jobs we have now, the people doing agriculture wouldn't even consider jobs. The idea that we could imagine all the jobs that are going to come, sitting here, that AI is gonna enable, I think is low. I think the need for like

• 19:39Speaker 02

  more creativity jobs is gonna go way up, and the need for jobs to process work for the creatives will probably go down in some ways. But I'm not even sure about that. We've had AI going, ImageNet was 2012, and then natural language stuff in Burton, all that was 2015, and then ChatGPT was 2022. And where's all the job destruction?

• 20:05Speaker 02

  Why hasn't it happened yet? And why are you so fucking sure it's gonna happen next? And why are you so sure no jobs are gonna be created? I don't think it's nearly as predictable as people are saying.

• 20:15Patrick O'Shaughnessy?

  How would you describe the nature and scope of your ambition over the next 10, 20 years?

• 20:23Speaker 02

  So I had a mentor who's a great CEO by the name of Andy Grove. And he was the CEO of Intel. And he famously did the major pivot of them out of the memory business into the microprocessor business, maybe the greatest tech CEO we've had. And one of the things that he said that in a way is very obvious, but I think is also profound is if you're the leader in the industry, then the growth of the industry is dependent on you. It's up to you to expand the market. Nobody else is gonna do it. When I think about the firm, I think of it a lot in those terms. The reason America is America, and there's many narratives on this, but the factual one is we won the industrial revolution.

• 21:07Speaker 02

  We had Henry Ford and we had Thomas Edison. We had like great entrepreneurs. They built great technology. The technology lead led to military lead, led to an economic lead, led to cultural dominance. None of that was by accident. Had we not had all those inventions, had all those companies, which led to, you know, everything from like winning World War II, we'd be some other thing. We wouldn't be America. So we're there again. Like this is the equivalent change of the industrial revolution in terms of how everything works, governments, societies, businesses. And we're either gonna be the leader of that technology, the provider of that technology, or we're not.

• 21:48Speaker 02

  And if we're not, we're not gonna be the economic superpower, the military superpower, the cultural influence, the standard of the world that we are now. I think that would be bad. I think America's been good for the world and good for giving people a chance like we talked about before. And so our role in that, from a policy standpoint, from a funding standpoint, from a helping people build standpoint, to make sure that that next set of great companies comes out of America or allied nations. The core ambition is to do our part in helping that.

• 22:22Patrick O'Shaughnessy?

  I want to ask about some of the ingredients to do that well, but just a quick sidebar on Andy Grove. His book is incredible. Everyone should read High Output Management. What very specifically did you learn from him? Like, what did you see him do that impacted the way that you think or behave?

• 22:36Speaker 02

  I'm so overly influenced by him. It's hard to even pin it down, but I actually wrote the new foreword for it. I actually think that's the best thing I ever wrote was a foreword to High Output Management. But the reason I wrote that foreword was it was my favorite book and I wrote The Hard Thing About Hard Things was basically intended to be the updated version of it. The thing in High Output Management that he did so well that I tried to do my own version of is the concepts of management are easy. You need an eighth grade education, maybe to kind of understand management. It's not like physics. It's pretty simple, but the psychological part of it is extremely difficult, particularly for a young person to be able

• 23:21Speaker 02

  to do. It's super confrontational. You're having to look through the conversation you're having to the entire organization. You really have to be Confucian at times. The good of the whole supersedes the good of the individual. And all these things are complicated to do. His big influence on me was me trying to not only absorb that, but then tell it in a more up to date kind of modern way. I went to visit him. He had this award on the wall, which was Manager of the Year for the Santa Clara Facility of Intel. And it was from 1992. I'm like, Andy, you're like the biggest CEO in the

• 24:03Speaker 02

  world. Why did they give you the Manager of the Year award for the Santa Clara Facility? And he goes, oh, Ben, he's like, you know, Santa Clara is the lowest quality score is the lowest fucking score on everything at Intel. And so I was just like, I'm going over there and talk to them. So I go over there. And he said, I brought a roll of toilet paper and I put it under my desk. I said, when are you going to get this facility up to code? And they just started in with all this bullshit, bullshit, bullshit, bullshit, bullshit. And I fucking reached under my chair and put all the toilet paper up.

• 24:44Speaker 02

  And I said, clean up your bullshit and tell me when the fuck you're going to be up to code. And in two months, they were up to code and they were always the highest rated facility thereafter. So they gave the manager of the year for that.

• 24:56Patrick O'Shaughnessy?

  When did you first experience the lessons that drove his success? This confrontational, psychologically difficult aspect of management yourself? How would you encourage other people to like, get a taste of it? They can't just read about it, obviously.

• 25:10Speaker 02

  What happens to founders is you invent something. Now I've got to build a company. You don't know what you're doing and you make mistakes. And then those mistakes really cost the company and you lose confidence. And that leads you to hesitate. That hesitation is what causes the failure mode. So then the company is indecisive or they get very open. All these guys got so open to input from their team and their executives. The team doesn't have the full context. Only the leaders got the context. So even if they're smarter than you, you still likely can have better judgment because you have all the knowledge. But you know, they defer and then if you defer to people who work for you,

• 25:55Speaker 02

  then that creates a weird political situation because people jump into the vacuum of you're not making the decision. I'll make the decision. And then that feels political to everybody else. So that's the pattern people run into. You really kind of have to build up enough confidence in them to have that confrontation. The hardest version of this, by the way, is the reorg. Because reorg is basically you're redistributing power to make the company work better, to like have communication be better, to not have as much conflict. But what's going to happen is somebody who's really good, who you've had for a long time is going to lose power. And they're going to be fucking pissed. So then if you compromise the organization so they can maintain their power,

• 26:38Speaker 02

  then you've just redistributed power from the people doing all the work to the executives. And that's a catastrophe. So it's always that thing where people don't want to have that confrontation. They don't want to tell that person, look, the organization's here. You helped us till here, but you either have to be happy in this new role or it's going to be a rap. When you're young and inexperienced, you knew it's going to hurt to tell him that. But I don't know it's going to help me to do this reorg. I'm not experienced enough to know that. I've never done that before. I'm going to go with the known avoid hurt to the theoretical avoid hurt. And that's when you wreck your company.

• 27:19Patrick O'Shaughnessy?

  You were lucky that when you started Andreessen Horowitz, you and Mark had both had tons of operating experience, both together.

• 27:25Speaker 02

  Yeah, I still didn't know what I was doing as CEO, though.

• 27:27Patrick O'Shaughnessy?

  Fair enough.

• 27:28Speaker 02

  And he didn't know what he was doing either. If you ask Mark about management now, like he's so different than how he actually did it. And it actually makes him mad if you talk about it too much because he's like, I got such bad fucking advice, man. They told me to hire all these guys.

• 27:40Patrick O'Shaughnessy?

  How do you think he's most different? Like, what would he say is, or what do you observe to him to be the most different?

• 27:45Speaker 02

  Mark is a super emotional person. And he's just way more in control of it than he was then in terms of just like the personality. He used to be like zero or a hundred. So he would be like full emotion. What the fuck are we doing? Or like, I'm just not going to say anything, nothing in between.

• 28:03Patrick O'Shaughnessy?

  Something I know the least about your firm is like the first, I don't know what period of time, three days, three months, three years. And I'd love to hear about how you thought about the business right as it was getting started. I'm going to come back to what it is now and those ingredients you mentioned for having the impact you want to have. But this is an incredible part of the world. Silicon Valley, Wall Street, these are institutions that make America great. Lots of people listening have ambitions to do this sort of thing. And I'd love to hear like the very, very early primordial case study of what it was like and what kinds of conversations you were having and what your initial ideas were.

• 28:40Speaker 02

  Venture capital, first of all, you kind of have to understand the context of it was there hadn't really been new top tier venture capital firms.

• 28:51Speaker 02

  The last one before we started that you'd say is top tier was probably Benchmark, which ostensibly started in 1995, but it didn't really because all those guys came from another firm called Merrill Pickard. That firm was from the 80s. There hadn't really been a new one from the 80s. And if you looked at why every VC was reputation based. And so to be top tier, you had to have invested in Apple and Cisco and Google and Yahoo and all the great companies. And you couldn't, from a standing start, get to that. And then if you're not top tier in VC, you're not going to last because in a super hot period, everybody makes money. But the best entrepreneurs will only work with the top tier firms because that's how

• 29:35Speaker 02

  you're going to recruit great engineers. That's how you're going to get follow on money. Like everything comes out of that. So you'd never take money from a tier two. And so that's why the tier ones always have better returns. So we knew we had to be tier one, but we had that problem. The idea that we had was venture capital is a great product for LPs, but it's not a great product for entrepreneurs. And so if we could build a better product for entrepreneurs, we could win. And that was the original framework. And the idea that we had for the product for entrepreneurs was, because we had been entrepreneurs, was around what you and I had been talking about, which is if you're a founder who wants to run their own company, you're not getting much.

• 30:20Speaker 02

  You need so much. You don't have the confidence. You don't have the knowledge. You don't have the know-how. You don't have the network. What if we built a firm that was designed to give you enough confidence, power, network reach, advice, that you could actually be a CEO? And so that was the whole idea behind the firm originally. The second idea we had, VCs didn't ever market themselves at all. Because if you're all based on your investing track record, it's best that it's just magic. Why say anything? Like, keep that a secret. And they weren't talking. And so when we went out and talked, everybody covered it. Instantly, everybody knew we had this product.

• 31:02Patrick O'Shaughnessy?

  Where did the germ of that specific idea come from? Like, let's be fairly loud relative to what others do from the very beginning?

• 31:09Speaker 02

  Well, it's funny because, you know, Mark and I were talking about it. He said to me, why don't VCs market? The original thing went all the way back to kind of the first class of VCs. The Industrial Revolution, VCs were JP Morgan, Rothschild, Goldman Sachs, et cetera. They were the ones financing these things. And it turned out that these guys were financing both sides of World War II. So they really didn't want any publicity because that would have been like an extremely fucking bad thing. To a large extent, that just carried over all the way through Arthur Rock. And then the reputation thing clicked in and it was working. So there was no need to do it. And we got a lot of criticism when we did it.

• 31:52Speaker 02

  Our LPs would say, you know, like the other VCs say, you guys are egomaniacs. You named the firm after yourselves. You're marketing it like this. And it was so funny because the reason we named the firm after ourselves is we raised money in 2009, which is right on the edge of the financial crisis. And the big objection from LPs was you guys are like really good entrepreneurs. You're just going to leave this thing and go build another company and then we're going to be stuck with the fund. And we couldn't get them off of that. So then I had the idea, why don't we just name it with our names and then they know we're staying. And that worked.

• 32:27Patrick O'Shaughnessy?

  If you think about the period of takeoff of the firm in 2009, up until you reach, let's call it like cruising altitude. When was cruising altitude? And what was the most difficult part about getting it from takeoff to that point?

• 32:41Speaker 02

  The first thing is we really didn't know that much about investing. Mark and I had done some angel investing, but neither of us had any venture capital experience. Credit to Sequoia, credit to Greylock and Kleiner and all the guys who were around at that time. They just had years and years of doing it. We made more than our fair share of investing mistakes, missing things we should have done and doing things that we shouldn't have done. But missing things that we should have done was probably the bigger one. And then the other thing is how we thought about the profile of the investor was wrong. We so over indexed on our idea that

• 33:19Speaker 02

  We had to help the founder become a CEO that we made it a requirement that you couldn't be an investor at Andreessen Horowitz if you hadn't founded and/or run a company. And that was a very good attitude and set the culture of the firm in a lot of ways and had good things that came from it. But most CEOs aren't as interested in investing as they think they are. Also, most CEOs aren't as good at helping somebody else learn the job. So those two things ended up being not quite correct. So we made some adjustments. Fund one just went really well because we, you know, we hit the scene hard. It was a small fund.

• 34:00Speaker 02

  We did Skype, we did Slack, we did Okta, Stripe was in there. There were just too many good things in a $300 million fund for that thing not to blow the doors off. Fund two wasn't as good as one. By the time we got to three, that's when we had contention among like, oh, we really don't have the right profile for GP here. And there was a while where we thought that was going to be a terrible fund, but being a great fund because we had Coinbase and Databricks and Lyft and GitHub. But that one was scary for a while, but coming out of that, we kind of knew what the firm needed to be. So I think it was settled down after that. It wasn't such a like startup. We got across that chasm.

• 34:42Speaker 02

  The bigger thing was, we always had this idea about software is eating the world. Mark articulated really well in his 2011 piece. We always felt venture capital firms needed to be able to scale and that the other firms would have trouble scaling because of the way they worked, the way they shared control. So that could be an opportunity for us, but we hadn't figured out how to do it yet. And then I'd say, starting with the bio and the crypto fund, I started to get to the organizational picture of how we would be able to address every market of technology, but with investing teams that weren't.

• 35:22Speaker 02

  20 people, that doesn't work. So you need an investing team of four or five people. You can't address the whole technology market with five people. So you have to have multiple teams. Having multiple teams in a venture capital firm is a little bit of a novel idea, particularly when each team has a platform that helps the founder build the company. We began it really in earnest with the crypto fund, I think, around 2018. And then now the whole firm is kind of organized that way.

• 35:52Patrick O'Shaughnessy?

  If we zoom now to today and back to what you said, which is the scope of your ambition is big as the leader, be the ones that are expanding the market. What are the components of doing that? What is the system need that it doesn't currently have that you might be able to provide?

• 36:06Speaker 02

  One is the capital markets have changed dramatically with not much help. So I went public at 18 months old with $2 million in trailing revenue. That wasn't a good idea, but companies used to go public routinely with $50 million in revenue. It was fine. Now nobody's going public.

• 36:26Patrick O'Shaughnessy?

  500 million.

• 36:27Speaker 02

  A billion, right? You get to go public or something like that. And you're kind of small if you don't have that. You kind of need a lot more out of the private markets than VCs are built to do. That's one of the things we have to think about. Another one is the companies in the portfolio, they'd leave you at 100 million revenue. They're going public, they're out to the races. Well, that's not true anymore. What do you need when you get to be 200 million, 300 million in revenue? Well, you need to be multi-product, you need to be multi-channel, you need to be multi-geography. So as a venture firm, we need to help them. As a venture industry, we need to help them do that. How do I get to Japan? How do I get to South America?

• 37:09Speaker 02

  Most venture firms don't provide much along those lines. So we have to step up to those ideas if we're going to have companies in the portfolio at that stage.

• 37:19Patrick O'Shaughnessy?

  Do you hope that over time, your firm and maybe some others like it that have become these big institutions in venture, go on to be sort of like the Blackstone, Apollo-type companies that are big publicly traded enduring businesses?

• 37:31Speaker 02

  A big, huge wave among venture capitalists is private equity AI rollups. It's a good business idea, just like the spreadsheet created the original private equity business. AI is creating a new private equity business where you can buy any existing company, optimize it with AI, and it'll be more valuable. That's a good idea. It's a good thing to invest in. It's not something we're going to do for two reasons. One, it's like the cultural opposite of who we are. So we are about the creation of new technology companies, growth, believing in the entrepreneur. Price

• 38:12Speaker 02

  doesn't even matter. As long as the thing succeeds, you're going to do well. Private equity is entry price is key. I had a great dinner with Mark Rowan, who's a super genius, runs Apollo, and he was like, entry price, entry price, entry price. We think about it, but it's not. First and foremost, thinking about containing costs and this and that and the other. That's just not what a good venture capital frame of mind is. Culturally, I didn't want to mix those two things. But more than that, like, I just didn't want to be in a business where the way you make money is you figure out how to optimize an existing thing and lay off people and that kind of thing. We're about new technology companies,

• 38:54Speaker 02

  building the future, taking things forward, and I'll leave that to the other smart guys in the industry.

• 39:01Patrick O'Shaughnessy?

  Your finance team isn't losing money on big mistakes. It's leaking through a thousand tiny decisions nobody's watching. Ramp puts guardrails on spending before it happens. Real-time limits, automatic rules, zero firefighting. Try it at ramp.com/invest. As your business grows, Vanta scales with you, automating compliance and giving you a single source of truth for security and risk. Learn more at vanta.com/invest. RidgeLine offers one unified platform that automates away the complexity across portfolio accounting, reconciliation, reporting, trading, compliance, and more, all at scale. Schedule a demo at ridgeline.ai. Every investment firm is unique, and generic AI chatbots don't understand your process.

• 39:45Patrick O'Shaughnessy?

  Rogo is built by finance professionals. It's connected to your data, learns your process, and quickly produces client-ready outputs. Check them out at rogo.com/invest.

• 39:57Patrick O'Shaughnessy?

  The best AI and software companies from OpenAI to Cursor to Perplexity use WorkOS to become enterprise-ready overnight, not in months. Visit workos.com to skip the unglamorous infrastructure work and focus on your product. What if any trade-offs feel like they might exist at this scale as you continue to scale? As you consider all these different people you're trying to serve? Well, the investors internally, the LPs, the founders, nothing's perfect. What are the trade-offs to the path that you've chosen?

• 40:24Speaker 02

  With any scale of organization, you really have to overpay attention to culture or the culture will drift. We probably spend more work on that than any venture capital firm. I'm like, you're not allowed to join unless you sign the culture document. I spend an hour with every single employee, teaching them the culture. We really try to enforce it hard when we can. We have pretty good consistency, but that is hard to maintain as you grow.

• 40:51Patrick O'Shaughnessy?

  Can you teach me more about culture? You've written a book about it. You've studied some very interesting cultures that you wrote about in the book. If you had to teach a seminar or something on what a culture is in the first place, and then how to design one, given what you do and who you are, and then how to make sure people live by it?

• 41:08Speaker 02

  Let me give you a small, but probably the most important insight, which is from Bushido, the way of the warrior from the Samurai. A culture is not a set of ideas. It's a set of actions. If you define your culture as a kind of set of ideas, integrity, do the right thing, we have each other's backs, or any corporate values, it's actually just a bunch of fucking platitudes that doesn't mean anything. The culture has to be defined in terms of the exact behavior that you want that support that idea. What do you have to do to actually be that thing that you want it to be? It's the little things. How responsive are you to your colleagues?

• 41:50Speaker 02

  What's the SLA on returning a Slack message or an email? Do you show up to meetings on time? Not everybody has those ideas, but if you want that idea, you've got to manifest it through something else. We have an idea about you have to respect the entrepreneur. Well, what is that behavior? Well, like, one, you can't ever be fucking late to a meeting with an entrepreneur. I used to fine people $10 a minute in the beginning of the firm to reinforce it. And then you have to get back to an entrepreneur. If you say no, you have to say no. You have to explain why you're not investing. And we're going to survey that entrepreneur after you say no, to make sure that you said no and that they had a good experience. That's a behavior.

• 42:31Speaker 02

  If you try to make yourself look good by making entrepreneur look bad, you're fired. You get on X and say, oh, he's selling dollars for 85 cents. No, no, no, no. We're dream builders. We're not dream killers. Fuck that. If somebody wants to do something larger than themselves, build a company, make the world a better place, we're for that. We don't give a fuck what the idea is or if Sequoia funded them or whatever. We'd love that. That's who we are. And so the behavior is the culture is the actual thing. And that gets you the idea as opposed to the idea and then figure out how you're going to behave. That's probably the main thing on culture.

• 43:11Patrick O'Shaughnessy?

  Can you say more about the influence your dad had on you? You mentioned that lesson of nothing's fair or life isn't fair. Tell me about your dad.

• 43:17Speaker 02

  He was what's known as a red diaper baby. My grandparents were communists. They went to secret meetings. They had cards. My grandfather was fired during the McCarthy era from being a junior high school teacher for being a communist. And he grew up a communist and he started out on the left. He was editor of a very famous left magazine called Ramparts Magazine, which he was editor of. And he was involved in the Black Panthers with Huey Newton and, you know, in the Oakland chapter. Eldridge Cleaver dropped out of politics and he reemerged eight years later on the right. He really understood the ills of communism and socialism, which helped me a lot. One of the things that he said to me that always stuck with me, he's like, "Son, go to the library.

• 44:02Speaker 02

  Pick any book on socialism. There's hundreds of books." And in that book, I guarantee you, you will find page upon page, chapter upon chapter of how to divide the wealth. You will not find a single sentence on how to create wealth. And I was like, oh, wow. That's not like a very good system, is it? I learned a lot about systems thinking from that. He wasn't this new age father. In the old days, your father, like, they wouldn't even talk to you till he got to be like 12. And you get these little snippets of wisdom. And one of the ones, I actually put in the hard thing about hard things. But I had three kids. I was young and I remember this, like 102 degrees. The air condition was broken. The kids were going crazy. Like one of them poured a whole bottle of apple juice, like a gallon of apple juice into the rug.

• 44:47Speaker 02

  And apple juice is steaming out of the car. But I'm just sitting there, I was looking like I was gonna die. And my father looks at me and he goes, "Son, you know what's cheap?" I said, "What?" He goes, "Flowers are cheap." I said, "Okay." He said, "You know what's expensive?" I said, "No, what?" He said, "Divorce." He had been married four times, so he knew.

• 45:08Patrick O'Shaughnessy?

  He knew what he was talking about. As you look out today in the world, I'm curious what things are captivating you most? And maybe even like most inspiring you? You have such an interesting perch. You get to see so much.

• 45:20Speaker 02

  What's going on in coding now is quite phenomenal. We kind of went through this period where, okay, AI can write code. Cool. Okay, you can vibe code stuff. A lot of security calls, fine. But I think over the winter break, it turned a corner where really good programmers were going, "Whoa, this helps me." I just became 100 times more productive. And I can't remember any technology where like just all of a sudden you wake up and everything, the whole world just changed like that. That's happening on a pretty regular basis, I would say. We spent a bunch of time with people in Hollywood who are using AI. I think AI will help you make movies. Both better and at much lower cost because you can shoot a scene and then have

• 46:05Speaker 02

  the AI do a variation of that scene. That's very, very good. If you're an actress, you have to shoot a scene like 15 or 20 times or something. Wouldn't it be nice to shoot it three times and then you just take the pieces you like and make it what you want? It's a little underestimated as a tool for creatives. I think that's true in music too. I was a young person when hip hop started and the huge criticism were like, this is not music. They're just taking music and they're remixing it and they're rapping over it and it's a bunch of bullshit. It's a novelty. It was post-modern art and I think we're going to get into post-post-modern art with what people will be able to do with AI and music. And that was one of the most exciting times in music. The invention of

• 46:48Speaker 02

  the new art form is when it gets really exciting.

• 46:52Patrick O'Shaughnessy?

  What people in hip hop, specific people have had the largest impact on you personally and how?

• 46:59Speaker 02

  Nas is a very good friend of mine. He's definitely had a big impact. Just the lens at which he sees the world is so different and interesting for me. We're both like very big fans of Rakim, who is kind of like the John Coltrane of rap. So Rakim, one of his first big songs was a song called My Melody. Nas and I are listening to My Melody. The first line is, "Turn up the bass, pull up a chair, hand out a cigar. I'm letting knowledge be born. My names are..." And so he puts it on, hands out a cigar, and he pauses it. And he goes, "Ben, why is he handing out a cigar?" And I go, "I don't know." Then he plays the next line. "I'm letting knowledge be born." He's like, "It's a birth, Ben. He's

• 47:42Speaker 02

  passing out cigars at the birth of knowledge." And I was like, "Oh shit, I've listened to that song a thousand times. I never heard that." I can't tell you how many times he sees or hears something that's there that I don't see. So having somebody that I can talk to who has just like a completely different perspective of all things in life. And it was interesting, we did the Coinbase deal together and he had called me like two weeks prior to us really seeing that because he wanted to learn about Bitcoin. So, you know, I explained to him how it worked. He was very interested. When I was talking to Chris Dixon, who was working on the deal, I was like, "Tell me about the guys." And he's like, "Well, you know, one of them, Fred, is like really into hip hop." I was like, Okay, I brought Nas over to my, I was like, have him come over to my house.

• 48:27Speaker 02

  There's a boxing match on Saturday and I had Nas come over and that's how we got that deal. But he's a big influence on me personally. I think he's one of the great storytellers of all time. Just a super genius on that.

• 48:41Patrick O'Shaughnessy?

  Is there a CEO comparable to Nas where there's this class of guys in the 90s where Jay-Z, you know, not just a businessman, I'm a businessman. There are these just massive franchises that got born. These guys all became incredibly successful in the business world. It felt more industrialized almost, like the whole process, even just his album that just came out. It feels like it could have come out then or now. It's like this weird timeless quality. He still has that somehow and like Premier, same thing. Do you know anyone else like that in another domain? It seems like such a unique person relative to his peers.

• 49:18Speaker 02

  Maybe Jensen. Jensen has this very defined view of who he is, what the company is and so forth. That's kind of gone across eras, but it's still the same thing. It played in gaming. It played in Bitcoin. It plays in AI, but it's still Nvidia. He never thought he had to change the name of a company. He's gotten better over the years. In a weird sense, it never felt like he's trying to be current. Nas never feels like he's trying to write a hit.

• 49:51Patrick O'Shaughnessy?

  Can you tell the story of the work you're doing with the Vegas Police Department? And I'm asking about this, one, because it's super interesting, but also because it feels like an interesting, different kind of example of what the application of this constellation of new technologies might allow for in terms of improvement efficiencies. It's just such an interesting case study.

• 50:11Speaker 02

  A couple of things about the Las Vegas Police Force were intriguing to me. The biggest one was they were different than other police forces in the country because they're a big metropolitan area that's not run by the chief of police, but run by the sheriff. And the reason that's important is the sheriff is an elected official and does not report to the mayor. So they never got caught. In the big political movement and defund the police, one of the only cities that didn't reduce the police budget or anything like that. So they stayed intact. And they're also, interestingly, the one that I knew that never militarized and they do community policing and you can see it in the numbers. So the murder clearance rate in Las Vegas is the highest murder clearance rate, meaning they solve the murder.

• 50:56Speaker 02

  Ninety-four percent. San Francisco is like seventy-five percent and then Chicago's like in the thirties and the national average is below sixty. And I asked, why is your murder clearance rate so high? And the sheriff, Kevin McMahon, said, Ben, when somebody is murdered, there's always somebody who knows who did it. They just don't talk to the police. So, but they talk to us because we're part of the community. They know us. So I was like, wow, that's a great environment to see if this new technology worked. And I knew about all the public safety technology because we invested in through American dynamism. So I was like, look, we're going to become the highest tech police force in America, hopefully the world. I'm just going to fund it. We've got a drone program and we've got prepared nine-one-one and we've got flock safety, you know, AI cameras.

• 51:41Speaker 02

  If a nine-one-one call comes in or if a gunshot goes off, there will be a drone deployed in there within ninety seconds. And then that drone video feed will be in every police officer's phone in the vicinity instantly. Since we started the program, I think crime is down over fifty percent. And then shooting of suspects by police is down close to seventy-five percent. But everybody's safer. And I think this is the thing that was the most surprising to me on the technology deployment is that when you talk to the police, they go, look, the problem is the descriptions cause half the violent confrontation. So I'm like, well, what do you mean? So somebody jacks a car. There's a baby in the backseat.

• 52:26Speaker 02

  We get a description of the car. It's a two thousand and four Hyundai. That's blue. Well, it's really a 2008 Hyundai that's green, but we pull a guy over in a 2004 Hyundai that's blue. That person has had bad experiences with the police. Now he's got a gun in the car and all of a sudden we've got an incident and like an innocent citizen gets harmed or a police gets shot. With AI camera, we know that's the car. That's it. And we know there's a baby in the car. So we're not sending one guy with a gun to see if that's the guy. We're sending a whole squad and we're apprehending them safely. Policing is inherently dangerous, but intelligence makes it dramatically safer.

• 53:07Speaker 02

  And so I'm a huge believer in this technology for making everybody safer. Suspects, criminals, citizens, police, everybody. The other knock on fact is it's put the pride back into policing. We used to have a big problem in Vegas where because nobody wanted to be a police officer, we were lowering the standard. But now the standard is really high. So between the drone center, which is like super state of the art, and then you have these cyber trucks that look so amazingly futuristic and cool driving around. Everybody wants to be a police now. Las Vegas happens to have the highest concentration of veterans in the country. Plenty of super qualified people to choose from. They all want to be police. That's all gone really well.

• 53:52Patrick O'Shaughnessy?

  The last question I ask everyone is the same. What is the kindest thing that anyone's ever done for you?

• 53:57Speaker 02

  There's a mentor of mine, a fellow by the name of Ken Coleman, who was the big executive at Silicon Graphics. And when I was a sophomore in college, I got an introduction into him and he gave me a job as a summer intern. Without that job, I don't know that I ever got to Silicon Valley. That was the highest impact. He didn't have to do that thing that anybody did for me.

• 54:20Patrick O'Shaughnessy?

  It may interest you that that is the most common form of answer across 500 of these, someone that like took a bet when they didn't need to. Ben, pleasure to finally do this with you after a couple of years of watching you and learning from you. So thank you so much for your time.

• 54:32Speaker 02

  Thank you, Patrick. It was fun.

• 54:34Patrick O'Shaughnessy?

  If you enjoyed this episode, visit colossus.com. You'll find every episode of this podcast complete with hand-edited transcripts. You can also subscribe to Colossus, our quarterly print, digital and private audio publication, featuring in-depth profiles of the founders, investors and companies that we admire most. Learn more at colossus.com/subscribe.

• 55:13Patrick O'Shaughnessy?

  You know how small advantages compound over time? That's true in investing and just as true in how you run your company. Your spending system is your capital allocation strategy. Ramp makes it smarter by default, better data, better decisions, better economics over time. See how at ramp.com/invest. As your business grows, Vanta scales with you, automating compliance and giving you a single source of truth for security and risk. Learn more at vanta.com/invest. The best AI and software companies, from OpenAI to Cursor to Perplexity, use WorkOS to become enterprise-ready overnight, not in months. Visit workos.com to skip the unglamorous infrastructure work and focus on your product. RidgeLine is redefining asset management technology as a true partner, not just a software vendor.

• 55:54Patrick O'Shaughnessy?

  They've helped firms 5X and scale, enabling faster growth, smarter operations and a competitive edge. Visit ridgelineapps.com to see what they can unlock for your firm. Every investment firm is unique and generic AI doesn't understand your process. Rogo does. It's an AI platform built specifically for Wall Street, connected to your data, understanding your process and producing real outputs. Check them out at rogo.ai/invest.