Ben Horowitz, co-founder of a16z, joins Sam and Shaan for a wide-ranging conversation covering leadership, management, and the real psychology behind why CEOs fail. He shares stories about Mark Zuckerberg’s early days at Facebook, how to have confrontational conversations that actually work, and why company culture has to be behavioral rather than abstract. The episode also covers Ben’s personal history in hip-hop, his behind-the-scenes role in reopening the Tupac murder case, and the Paid in Full Foundation he runs to give pensions to the original hip-hop pioneers.
Speakers: Sam Parr (host), Shaan Puri (host), Ben Horowitz (guest, co-founder a16z)
Introduction: Tupac, Vegas, and the Blind and Deaf Crew [00:00:00]
Shaan: All right, today we’re hanging out with Ben Horowitz, co-founder of a16z. These guys manage 46 billion in assets. They’ve invested in Stripe, Coinbase, OpenAI, a bunch of the big hit tech companies. But today we’re talking about stuff you don’t usually get to hear from Ben — things like how do you actually have a high-confrontation conversation, the advice he actually gives his founders, when he met Mark Zuckerberg and what he noticed about Mark that was different, and what makes him such a great CEO that you can kind of steal from Mark Zuckerberg’s playbook. Sam, what else have we got?
Sam: Dude, we also just hung out with him, which is like the best part. He tells a story about how he helped catch Tupac’s killer. And we also asked him what interests him right now — what books is he reading, what content is he consuming, what rabbit holes is he going down. It was incredibly interesting.
Shaan: Awesome conversation with Ben Horowitz. Enjoy.
Ben: Okay, so I have a good Tupac story for you.
Shaan: Oh my gosh. All right. I’m incredibly excited to hear it.
Ben: So my wife is the biggest Las Vegas evangelist in the world, and she was talking to Quincy Jones’s son QD3 and said, “You know, you need to move to Vegas.” And he’s like, “Fuck that. I’ll never move to Vegas. They didn’t solve the Tupac murder.” His sister Kada was dating Tupac. So I was like, “Let’s have dinner with the Vegas PD and see what happened.” Me and QD3 and Nas sit down to dinner with the Las Vegas Police Department and they bring the whole case file. It turns out the LAPD really fouled the case — almost on purpose, it looks like.
So at the end of the dinner, I say to the chief of police, Mike Janeiro, “Mike, you ought to reopen the Tupac case.” And he goes, “I’ll talk to the sheriff.” Next day I call him. “What’d the sheriff say?” He said, “If Ben wants us to open the case, we’re opening the case.” And they reopened the Tupac case. And they caught the guy.
Sam: That’s insane. So Shaan, I don’t know if you know the story, but basically Pac and Suge got in a fight at a Mike Tyson fight and then 30 or 40 minutes later he was shot right on the Strip in Las Vegas. It was a cold case for years, but everyone knew who did it — they knew it was this guy named Orlando Anderson. That was the rumor.
Ben: Orlando pulled the trigger. Keffe D told him to shoot him. Yeah, exactly. And everyone knew this, but for some reason it just didn’t happen. And Orlando ended up dying a handful of years later. The craziest thing ever is there’s this guy named DJ Vlad who does these interviews with all these gangsters, and he got Keffe D to tell the story about the murder. This idiot went on a podcast and just said, “Yeah, here’s what happened.”
Shaan: So here’s why he did that — he thought he had immunity because the LAPD had proferred him. Which means basically, in exchange for testimony, we grant you immunity. But they granted him immunity in LA. Not in Vegas.
Ben: The Las Vegas PD were like, “Oh, that doesn’t count here.”
Sam: And then little do we know that Ben’s behind the scenes getting it all done. That’s pretty awesome. I followed that case religiously. I thought it was riveting. I did not know you were involved. That’s pretty cool.
Shaan: All right. Well, Ben, we like to typically start with our intro music — for some reason it’s not playing. I’m trying to get this cassette to play but it’s just not playing. What are we looking at here?
Ben: Oh boy. That is the Blind and Deaf Crew. So my friend Seth Clark — this was back in ‘87 or ‘88 — got shot and was blind. So we formed a rap group called the Blind and Deaf Crew, D-E-F. And we had all kinds of rhymes about being blind and being deaf. Like, “The blind deaf crew, you know where fly three of us but we got four eyes” — that kind of stuff.
Shaan: [laughter]
Sam: Where did you grow up? I know who your dad is — he was a well-known academic — but where were you growing up where you were around guys who got shot and were rapping?
Ben: So I grew up in Berkeley, California, which is either an academic town or part of Oakland depending on where you are. I was in the more Oakland part of Berkeley. Then I went to school in New York, got into rap in New York. And then Seth got shot back in the Bay Area and he was very, very depressed — he was only a kid. So I sent him these DJ Red Alert and Chuck Chillout mixtapes, tapes I’d recorded off the radio show, which had brand new hip-hop. That kind of cheered him up, and that’s how we got into rap when we came around. We didn’t succeed, but we tried real hard.
Why Most Management Books Are Terrible [00:08:00]
Shaan: Well, we wanted to just hang out with you because there’s — you’ve done 50,000 podcasts. I think a16z now has 50,000 podcasts.
Ben: Yeah.
Shaan: We could sit here and be like, “Hey, is AI a bubble?” Like we can kind of do that, and we’ll probably ask you something about AI. But I think more than anything, what we try to do on this podcast is give people a sense of what it’s like to hang out with Ben Horowitz. We come from a business and tech background, so we got a bunch of questions around that. But for me and Sam, the most interesting part of what you’ve contributed to the collective wisdom of founders is your stuff on leadership. You’ve written two books. I feel like they’re really top-shelf on how to be a leader. And I think it started with a general philosophy. So tell me — why are most management books terrible?
Ben: The problem with management generally is it’s very situational and emotional. It’s like, oh, here’s a book to teach you how to play NFL quarterback, and you could read it 20 times — but you go out on the field and things are extremely different. If there’s a 290-pound guy running at you extremely fast trying to kill you, what you feel, what you think, how you process that is just different. And I think management tends to be like that, in that it really has to do with your situation and the feeling you have at the time it happens.
So these management books are written like it’s some step-by-step thing that anybody with a basic eighth-grade education can understand. The principles aren’t that complicated.
Sam: Look at the cookbook and you can just follow the recipe.
Ben: Yeah. “Oh, here are the five steps for building a strategy” or “the three steps for setting objectives.” It’s not actually very useful at all because that stuff is so simple.
I always thought the difficult thing is — you’re either going to run the risk of running completely out of money if you don’t fire half the company, but you don’t want to have that conversation because you promised all these guys the company was going to be a success when you hired them. The level of inconsistency you’re going to have to go through, the level of “I was completely wrong about everything and now I’m going to fire half of you because of the mistakes I made” — that will cause you to hesitate in a way that could kill the company itself. How do you get over that? What do you actually say? How do these conversations work? That’s the actual thing that people need to understand. What are the words that get me out of this thing — at least temporarily?
Nobody had been writing like that. The last guy who I thought wrote a book like that was Andy Grove when he wrote High Output Management, and that book was really old by that time. So I was like, well, somebody ought to write the sequel. It’s been 30 years.
Mindset vs. Technique: Getting to the Truth [00:13:00]
Sam: Do you think that when it comes to leading, it’s mostly about getting your mindset right? Is that what you’re saying?
Ben: No, no, no. It’s more complicated than that. You kind of strive to get to a point of honesty — like true honesty, where you’re actually being true and not lying to yourself. That’s hard. It’s almost like — you guys are kind of creatives on the podcast side — but to be a great creative, at some point you have to get all the way to that very vulnerable point where you’ve exposed yourself in all your issues and weaknesses. And leadership is a little bit like that, in that you’re kind of pushing and pushing to get all the way to what’s true.
That’s part of it. But the other thing is you don’t really necessarily completely know what you’re doing, particularly when you start building a company. So you have to have this confidence game where you talk yourself into: okay, I think I know enough to do this.
And it can be very little things. I had a conversation with an entrepreneur. He’s like, “Ben, I need your help.” I said, “Why?” He says, “My CTO is an asshole.” I said, “Well, he’s a good CTO — I know that from talking to you before.” I said, “You’re not even asking me to fire him, are you?” And he’s like, “No, I’m not asking you that.” I said, “Well, tell me why he’s an asshole and maybe I can help.” He says, “Well, he made a young woman on our finance team cry yesterday.” I said, “Okay, yeah, that’s kind of mean-spirited for a CTO to do that.”
I said, “So you’re really asking me not how to fire him, but just how to have a conversation with him about his behavior without him quitting. That’s what you’re saying.” And he’s like, “Yeah.” I said, “Look, here’s what I would say to him: ‘Hey, you’re a fantastic director of engineering, but you’re not an effective CTO. If you want to be a director of engineering forever, we can just run it like that and it’s no problem — you do a great job managing your team, you get stuff done on time, you’re great. But you’re not effective with the rest of the organization.’ And that’s what a CTO is. The CTO has to marshal the resources of the whole company to get the job done. And if you go to a junior person five levels below you and make her cry — you’re probably right, but you’re never going to get what you want out of her. So you can’t be effective with her. How are you going to be effective with execs? If you want to learn how to do that, let’s learn. If not, no problem — but just know at some point I’ve got to bring in a CTO.”
That’s where I would have had the conversation. And that kind of got them to: okay, now I can work with them. So much of the mistakes CEOs make — they just don’t know how to have the conversation.
So the mindset part is correct in that there’s a confidence component. But there are techniques, there are ideas, and it’s just harder than it looks. And the mistakes compound. Not talking to him is going to multiply — now you’re going to isolate engineering, nobody’s going to like them, you’re going to have politics in the company, people just don’t want to work there, you have high attrition, the board’s all upset. It snowballs on you if you can’t deal with these things.
Sam: Man, this is so cool because I just read this book called The Motive, and the whole book is about how to have a conversation like that. And I remember reading it and I was like, I don’t want to talk about this on the pod because I feel stupid that I’m having to learn a script on how to have a confrontation with someone. And then I hear you talking about this and I’m like, all right, I feel a little bit better. Why is this conversation hard for me? It should be easy. I literally don’t know what words to use for this to be an effective confrontation. I had to read a book.
And it’s cool to hear you describe that other people — I think you even said in another interview that you’ve seen inside these companies and they all face these challenging situations where they just don’t know how to communicate.
Ben: Yeah. Nobody learns how to be CEO of a big company without actually being CEO. You found a company, it starts growing, you don’t know what you’re doing, you make mistakes, it’s very scary. It’s easy to lose your confidence. And if you lose your confidence, you hesitate. And if you hesitate as CEO, somebody’s got to step into that vacuum — and then it becomes very political and dysfunctional.
How to Have a Confrontational Conversation [00:20:00]
Sam: You’ve said before that having confrontation the right way is super important. And I nodded my head and then I was like, cool, I really don’t know how to do that. So — what is the right way to have confrontation?
Ben: It’s complicated, but the first thing is you’ve got to stop thinking about yourself. You’re going to be saying something they don’t want to hear. And people get caught up in either “I need to be a tough guy” or “I need them to like me” — some other thing that’s about you. But really, you have to go: what am I going to say to them that isolates it to the thing I’m really talking about? If I need them to change this behavior, how do I get them to hear it in a way they can actually act on without getting in their feelings?
In order to do that, you just have to be very straightforward, and you have to be open. If you think they’re a shitbird, you’re probably going to have to fire them anyway. But if you think they’re otherwise good, then you kind of have to let them know that — but in a way where you’re not clearly setting them up. You’re not giving them a shit sandwich. “You’re the greatest person in the world, but this is all messed up, and I love you.” People are onto that. It’s too simple.
So you have to get to a very honest place with them and say, “Look, you’re working with us on this, you’re doing this, it’s not working, it’s not effective. I can help you get it to be effective, but I need you to get it to be effective.” People will accept things from you if they feel like you’re telling them the truth. Like: I’m completely open and honest about this. I’m not telling you it’s worse than it is, and I’m not telling you it’s better than it is. I’m telling you what it is.
When I said earlier that a lot of leadership is getting all the way to the truth — you have to sit with yourself and say, what do I really think about this? Not what people are complaining about, not that it hurt my feelings. You have to get beyond that and go: what’s really true? Why did they do it? Can it be corrected? If it can be corrected, what would motivate them to correct it? You have to get all the way to that. Otherwise they’re just going to get upset and defensive, or they’re not going to hear it because it’s too soft. “Well, yeah, Ben kind of doesn’t like that, but he doesn’t really care.”
Shaan: You’ve invested in and known for a long time a lot of the biggest tech CEOs. And the stereotype of the most successful tech founders is this slightly autistic, very high-IQ, lower-EQ persona. But that’s not what would be good at the thing you’re talking about. So is the stereotype just wrong? Did they learn these things? What’s going on?
Ben: I think some of these guys have much higher people-understanding than you might think. The ones who truly can’t read people don’t become Mark Zuckerberg. Mark Zuckerberg’s mom is actually a psychiatrist or psychologist, and he’s actually pretty insightful — you can see it in the deals he’s negotiated and the moves he’s made. The guys who are processing information at that rate of speed, it’s a little weird — you always feel like, what the hell is wrong with my clock, this guy’s thinking faster than me.
My very first conversation with Zuck was I think in 2007. At that time, the Facebook traffic had flattened, and the executive staff he had was trying to run a coup to force him to sell it to Yahoo. They were leaking stuff to Valleywag, calling for Zuck to be fired — the whole stupidness.
His first question to me was, “If I fired my executive team for the second time, would the board be nervous?” I said, “Well, that’s not even the question, Mark, because if you’re asking it, you kind of have to do it — because you can’t succeed with them. Whether or not you can succeed without them is at least a question mark. You’re going to die with them.”
And then I said, “But let’s talk about why traffic has been flat.” And he said, “Well, we doubled the size of the engineering team this year. We went from 400 to 800 engineers. The way the product is architected, we had a MySQL layer and then an API and then the applications are built on the API. But a lot of the new engineers just wrote straight to MySQL and messed up the whole thing. Now it takes like 10 seconds to log in, so traffic flattened because of that.”
I said, “How do you train these guys?” And he said, “Train these guys?” And I never forget that. I was like, “Oh shit.” I said, “Zuck, when you’re 10 people, there’s no knowledge in the company — everybody just comes on and starts working. But when you get to 800, a thousand people, you have a lot of knowledge in your company about how the product works, how you check in code, everything. You actually have to teach people that, because they don’t know who to ask.”
And just to show you what kind of CEO he ended up being — he created this two-month boot camp for every engineer and every product manager who entered Facebook. He had to go through this thing and learn everything. He is a phenomenal student of management.
The ones who truly don’t understand people don’t actually turn out to be good CEOs. You can make fun of Larry Page or Elon or Zuck, but they are actually very smart about people. All three of them.
The “Where’s My Money?” Technique for Unsticking Projects [00:30:00]
Shaan: You have these great stories. One I think is in your new book — relevant to any business size — was about collecting money. It was about the CEO of Nación LA?
Ben: Yeah. They’re living on the edge, they need every dollar collected, and cash collections were just off track. All this dumb stuff was happening — they sent out the wrong kind of email, didn’t get a response, this and that.
I said, “I learned this technique from Andy Grove: if a project is off track, just go, ‘Okay, 8 a.m. every day, we’re going to meet on it, and I’m going to be in the meeting and I’m going to want answers.’” What that meeting actually turns into is every dumb thing going wrong gets resolved very fast, because people don’t know who to ask, how to resolve it, whether it’s a problem.
So I said, “Leah, just every day at 8 a.m. get everybody in the cash collection team together and start the meeting by saying, ‘Where’s my money? Why haven’t we collected it?’ Make them explain to you why they haven’t collected it. You’ll be shocked at why they haven’t collected it.” And sure enough, it’s like, “Well, we didn’t know we could edit the email.” And she’s like, “You didn’t know you could edit the email?”
Those kinds of things start popping up. “I didn’t know I could do this, because I don’t think I’m allowed to.” And you say, “No, I’m the CEO. You’re allowed to do it.” That can unstick a project that’s way off track or a process that’s way off track.
It’s a different idea about management: as you grow, communication becomes your biggest challenge. So it’s a way to go, “Okay, I’m going to manually, unscalably fix communication in this organization right now.” And the amazing thing is it tends to be very long-lasting — once they get that, it sustains.
Sam: I had an experience with a founder you invested in. Do you know Sulie Ali? He’s one of my good buddies. You guys invested in Tiny back in the day.
Ben: Of course. Yeah, yeah.
Sam: He does this exact thing. This founder emailed us and was like, “Hey, we’re going to start raising money, it’s really important, I would love to pick your brain” — very like, “Can I pick your brain? Would you like to get coffee?” But: “My house is on fire.”
We were like, “Wait — just to clarify, is the house on fire?” He’s like, “Yeah, yeah, the house is on fire.” So we said, “Okay, well, let’s meet now. Why are you emailing me? Let’s just talk right now.” He jumps on the call. “Okay, what do you have so far? Let’s raise the money.” And he’s like, “Uh, here’s the pitch deck.”
Basically in the first 30 minutes, we gave him three things: “Hey, here’s three things. These are the three most important things you’ve got to change. This part of the story is broken. You’re missing this information. You’re framing it the wrong way.” And he’s like, “Okay, this is so helpful. Wow. Thank you guys. Would love to touch base again next week.”
And Sulie was like, “Next week. How long do you think it’ll take you to make those three changes?” And: “How about we meet today at 3 p.m. and you show me?” And we did two-a-days with that. It kind of broke my brain a little bit because there was this invisible wall as a business person: you don’t meet twice in a day. Like, that’s a faux pas. It’s bad manners. But like — is this a big problem or not? Just clarify that for me. Because if it is a big problem, I’ll just keep showing up and saying, “Okay, now what? Okay, now what?” If you just do that for three days, all of the excuses get squeezed away. All the excuses suddenly disappear and you get to the brass tacks about what’s going on. It was amazing.
Ben: That’s definitely right. Yeah. And I actually had a lot of conversations with him — he went through a lot of crises.
CEO Confidence: The Number One Reason Founders Fail [00:37:00]
Sam: Can I ask you about confidence? You give a talk with your portfolio companies about how they don’t fail due to lack of competence, but lack of confidence.
Ben: I would say the number one reason a founder fails at the CEO job is some kind of lack of confidence, crisis of confidence — whatever it is that causes them to hesitate. “Okay, I should do this, I can see that I should do this, but I’m not sure I should do this, so I’m going to wait.”
Sam: If you had to teach a class on how to improve someone’s confidence, do you have a framework? Some bullet points you’d stand by?
Ben: At the end of the day, confidence is personal. You have to feel it yourself to have it. It’s like the Wizard of Oz — I can give you a clock and tell you it’s a heart, but at some point you’ve got to believe it.
And the thing that causes the crisis in confidence is: you invent something, you hire a bunch of people, you make a decision, it’s wrong, people really suffer from it. You feel horrible because you’re like, “I don’t know what I’m doing, and I made a mistake, and it had real consequences.” Most people in life don’t face a situation like that until they become CEO.
So a lot of the idea behind the platform at a16z is: what if you could call anybody? What if you could call anybody in the White House, in Congress, any executive, any big-company CEO, and have a conversation? What if we could build that network for you?
And then I used to have this event — I should probably bring it back but I ran out of room in my backyard — called the CEO Barbecue, where we’d bring all the CEOs from the portfolio and put very famous people around them. So we had Zuck and Larry Page and Kanye all at a barbecue. No talks, no business agenda, no toast — just a barbecue. Just to make them feel like, “Oh shit, like I know Kanye. I have to be somewhat important.” So you’re trying to imbue this feeling: I may not totally know what I’m doing, but I should be CEO.
Shaan: What about the inverse — when you look at a CEO and you’re like, their confidence is going to go horribly wrong and it’ll be their demise? What decisions do those people make? What are the commonalities?
Sam: The Charlie Munger thing — “tell me where I’m going to die so I know not to go there.” What are the decisions that take me off the path?
Ben: I would say the big thing is it’s almost like a lack of decision — a hesitation. In football, they always say you have to trust your eyes, because you could be really fast, but if you don’t start running when you see the thing, if you wait, then you’re not fast. It’s kind of like that for CEOs. You could be really smart, but if you wait too long before you pull the trigger, you’re not smart anymore. It’s too late.
There are all kinds of excuses people tell themselves to not make a decision. Like: “We made such a big deal when we hired him — what’s the press going to say?” Or “I don’t have time to hire a new person to do the job this guy is messing up.” Those kinds of reasons not to make the decision — if you think about them for more than five minutes, you go, “That doesn’t make any sense, because this guy is messing up the whole org. Who cares what the press says? Just get rid of him. Start rebuilding now. No job is better than a bad job.”
Everything kind of ends up like that. “I don’t know enough to make the decision. I didn’t give them enough of a chance.” That lack of confidence causes a no-decision where there really needs to be a decision. That’s the common pattern.
Sam: Yeah. So in the two examples you gave — the first one was avoiding the conversation is the mistake. And in this one, avoiding the decision is the mistake.
Ben: Yeah. You have to run toward the pain and darkness. You can’t run away from it. If you run away from it, it’s all bad.
Sam: You’re pretty good at titling blog posts and books. “The Hard Thing About Hard Things” — that’s badass. But I think you said the publishing industry typically doesn’t go with the author’s title, and you were bragging that you came up with that one and they ran with it.
Ben: Yeah. I actually didn’t want to write the book — the publisher asked me. So I felt like I didn’t do what I wanted. So I called it what I wanted.
What Excites Ben Right Now: Defense Tech and Flock Safety [00:44:00]
Shaan: What excites you right now? A lot of what we talked about is the hard stuff, the pain. But nobody gets into this just for the pain. The pain is just a necessary thing we go through to do the good stuff. What rabbit holes are you going down? What cool stuff have you seen that you can’t forget?
Ben: One of the most exciting things going on now is — it’s well known that the United States has kind of fallen behind in defense, manufacturing, rare earth minerals, all these kinds of things. But what’s been very exciting is there are startups that are like, “Oh, I’ll solve that for America.” We just funded a company called Periodic Labs that uses AI to do novel material science — enabling better design of everything from rockets to missiles. And then we have a company called Cobalt Metals that uses AI to analyze dirt samples and tell you, “Oh yeah, there’s going to be copper below that, about a mile down.” So these techniques where you’re using tech to go, “No, we’re going to catch up fast” — that’s been very, very exciting.
Sam: My view as a founder on the ground is just that sometimes you see something and it breaks an imaginary wall you had. And sometimes things become cool. Although we try not to follow trends, sometimes you can use your psychology for you rather than against you. Seeing what Elon has done — going into these really hard spaces, literal rocket science, unafraid of that. And you going in and doing weapons and defense tech, making that cool and kind of patriotic. Is that what it took?
Ben: There are very challenging companies to build in some ways. But on the other hand, it’s a good time to do them because people because Elon has shown that it’s possible. God bless Elon for showing that it was possible. So whereas only Elon could have financed Tesla, normal people can start to finance these things now because Elon has shown it’s possible. It’s a little bit like the four-minute mile in that way.
And even in public safety — you look at something like Flock Safety. Technologically it’s not nearly as complicated as an Anduril or something, but it’s very powerful. They make policing, being a citizen, and even being a criminal more safe, because all of a sudden you’re using AI to provide real intelligence.
For example, in Las Vegas where they deployed it — a huge problem in police violence, cops getting killed, are traffic stops. A big reason is somebody reports there’s a brown Honda Acura that kidnapped a baby. That description is usually wrong. So you have Flock Safety, you have the exact match. The difference between a cop going into a situation where they may have the wrong guy — where the guy could get very agitated and you have a bad situation — versus knowing 100% this is the car and there’s a baby in the back that’s not his. You’re not sending a single person in with a gun off a motorcycle. You’ve got a whole team making sure that person is apprehended safely and correctly, and the baby is safe.
Sam: I’ve heard Flock Safety is amazing. Is it drones? Cameras? What are they doing?
Ben: It’s primarily a camera system where AI will basically — somebody does something, they grab the car on the camera, that car shows up on another camera anywhere in the city and they’re like, “Oh, there it is.” That’s actually how they caught the Tesla terrorist who set the Tesla on fire in Las Vegas. He came in earlier to case the place. Flock Safety picked up the car. They saw the car come back at night and were like, “Oh, we know whose car that is.” And they just went and arrested him.
Did You See That Ad? The Trend Toward Hardware and Defense [00:49:00]
Sam: Did you guys see that ad? I think it was about two weeks ago — it went viral on Twitter. I believe it was a solar company, and they had a whole website dedicated to recruiting. They bought an ad in the New York Times and it was like — an old man sitting with what looked like his grandson overlooking solar panels. And it was like: “Do you really want to tell your grandkids that you spent your entire 30s and 40s building just B2B software?” It was great.
And there’s this whole trend among young people on Twitter of being more traditional. And I think to answer your question, Shaan, about Anduril and Elon — I think it’s been a perfect mix of people seeing Elon and Palmer do these interesting things, and also just getting sick of just building B2B software. And the software had to get good enough to make these other things possible, which it now is. And it’s amazing that we’re at that time where you can really imagine changing the world in all kinds of ways.
AI Video Is a New Medium, Not Just a Better Tool [00:52:00]
Shaan: You get to see a lot of pitches from the smartest people in the world telling you what the future looks like in five years. You’re a little bit like a time traveler. What’s broken your brain — from a demo or a story or a pitch — sometime in the last year?
Ben: So I think in the creative space — I’m starting to realize that AI video is not making the old thing more efficient. It’s a new medium. It’s an actual new thing in the same way that movies weren’t plays. AI video is not video. The stories you can tell are completely different, because you can do things that without a $200 million budget you had no chance of doing, and now it’s just no problem.
And how well it’s working on existing stuff — the people on the cutting edge of the movie industry are now able to do whole movie scenes, have the AI actor do the third cut at a level of quality where even the actor doesn’t know it wasn’t them doing the acting. So it’s going to change dramatically, and there’s going to be white space for not only new creatives but new entertainment entrepreneurs that nobody is really imagining right now.
Sam: Is there any AI content you consume as a fan?
Ben: Yeah. Like, you know, I’ve been watching that one with the cat over the weekend — the cat playing all the instruments and the lady coming out. Unfortunately you got to cut that racket out. Did you guys see that one?
Shaan: That was pretty good. Yeah, I think it’s a Sora video.
Sam: Ben, do you mess around on Suno at all for AI music?
Ben: Yeah, Suno. And 11 Labs has a model, and Udio’s got a very good model. There are a few different really good models. I feel like I could have a music career again. That’s going to be very, very interesting to me.
One thing hip-hop showed — and people don’t really realize this, but Quincy Jones pointed it out to me before he passed — he said, “Ben, hip-hop started at exactly the same time they canceled all the music programs in schools. That’s exactly when hip-hop began.” Hip-hop kind of freed you from having to learn to play an instrument. Even for the producers, right? You had a drum machine, you had samples, so you could hear what you liked and play it, but you didn’t need to be a virtuoso. That opened up a world we didn’t have before.
I think AI music is kind of that on steroids.
Sam: I don’t know if you guys know this, but the number one song in the country right now is by an AI country artist. It’s called “Walk My Walk.”
Ben: Oh yeah.
Sam: And the first AI artist that got a record deal — so this is definitely what the future looks like. People who are non-musicians. It’s just like Replit and others making it so you don’t have to be a coder to make apps. Now you don’t have to be a musician to make music. And I don’t think people really understand how big a deal that is.
My personal trainer — who’s been in the fitness world his whole life — has been in a rabbit hole making AI music. He’s probably in the top 0.1% of AI creators in the world right now. He’s got a full band, he’s his own record label, and every day he’s up till 2 a.m. knowing these programs inside and out. Because it wasn’t really accessible to somebody without musical talent before. There’s a big difference between taste and creativity and being a virtuoso violinist. Those don’t necessarily have to be the same thing.
Ben: Right. And it’s pretty neat to have a world where, okay, if you can just do this part, you can still play.
A16z Culture: Rules That Shock, Rules That Stick [00:59:00]
Shaan: Ben, I want to ask you about the rules of culture and making them memorable.
When I was doing research, one of the things that stood out is you talk about culture in a way where — normally culture makes me fall asleep because it is so overtalked about in the business world. Culture, culture, culture. Tell me your values: integrity. All right, great. Glad to hear it. I was worried it was going to be the opposite. It doesn’t really tell you anything. And you walk into the company and the stuff on the wall doesn’t match what you see happening inside. So you get disillusioned.
But one nuance I thought was cool — you were talking about how at a16z you drive culture through onboarding. You do a one-hour culture session, they sign something at the end. And your rule for writing the culture rules is: it has to have some shock value. It has to give the other person a “what the hell are you talking about” reaction if it’s going to be memorable. If it’s not memorable, it’s never going to be remembered or used. Can you talk about your theory around this?
Ben: Yeah. It kind of comes down to what you do every day — it’s a daily habit. This idea that you put cultural values on the wall and then once a year in a performance review you say, “Do you follow the culture?” — that means absolutely nothing.
So: what do you do every day? At a16z, we meet with entrepreneurs every day. So what’s a rule that sets the culture around that? Well, if you’re late for that meeting, it’s $10 a minute. “Well, what if I have to go to the bathroom?” You owe me $50. I don’t care. “What if I had an important phone call?” You owe me $100. I don’t care you had an unimportant phone call.
“Well, why am I paying to work here?” Because building a company is extremely hard. Culturally, we want to have the ultimate respect for that. We don’t want to waste any entrepreneur’s time. So you have to plan around it.
Sam: You guys have a fine now. This is a real a16z rule.
Ben: Yeah. So every time I go to a meeting, I have to think about it because I’ve got to be on time. I’ve got to plan my day so I’m not back-to-back on that one. And then: why am I doing that? Okay, if you do that, that’s a habit that makes you go, “No, I’m going to respect what this is. I know how hard it is to build a company. And somebody here thinks it’s hard enough that I have to show up on time.”
Sam: Can you tell some more of those? The tardiness paying thing is pretty cool. What are some other examples?
Ben: A second one: if you talk smack about an entrepreneur on X, you’re fired. Doesn’t matter if they’re in the portfolio or not. Just that’s it.
Why? Because culturally, first of all, we’re dream builders, not dream killers. If you want to do something bigger than yourself and make the world a better place, I don’t care what it is, I don’t care if I think it’s stupid — I’m for that. And I don’t care if Sequoia funded you or Benchmark funded you. We’re pro-entrepreneur.
Related to that: I don’t want to give anybody credit for making themselves look smart by making somebody else look stupid. I don’t want to give anyone a gold star for saying, “That guy’s selling dollars for 85 cents. Ho ho, I’m so clever.” No. We’re not doing that here.
So it seems like a harsh punishment, but once you’ve heard it and you understand it, it becomes a way to show up behaviorally every day — as opposed to just having “integrity” on the wall. What does that even mean? Integrity only matters when it’s tested. Everybody has integrity until it’s tested. And when it’s tested — when it costs you money, when it costs you a deal, when it costs you your marriage — very few people actually have it.
So you can’t have it in the abstract. You have to say: what behaviors do you have to have to work here? How responsive do you have to be? These things end up making the culture much more than abstract values.
The samurai called them virtues, not values. These are your virtues. This is your way of being. This isn’t a set of ideas. A culture is a set of actions.
Sam: Listen to this, Shaan. If you go to a16z.com/about, you’ll see their values. I just want to read a couple. Number six out of seven: “We play to win. Our culture only matters if we’re important. And in order to be important, we must win. We are the best firm in the world, so we expect to win.” I love that. It’s polarizing — a lot of people aren’t into that — but that’s badass. And then: “We only do first-class business and only in a first-class way.” I really like that one too.
Ben: I actually stole that phrasing from JP Morgan. [laughter]
Shaan: Oh yeah?
Ben: He said it in court. They were accusing him of some kind of market manipulation and he said that. I think I read it in Andrew Sorkin’s 1928 or ‘29 book.
Sam: So cool. But what you were just saying is a little different from the website. There have to be behaviors that support the principles.
Ben: Yeah. There’s got to to be behaviors that support the principles. You have to ask: what are the daily situations and actions where we have a choice? We either show up this way or we show up that way. And sometimes with a penalty or a praise based on the extreme version of that behavior — a no-tolerance policy.
There’s a great military quote in the book: “If you see something below standard and you don’t correct it, you set a new standard.” That’s very true. And that’s why they have to be specific — because if they’re not specific, you can’t enforce it. How do you enforce “you don’t have integrity”? That just gets weaponized. “Oh, he doesn’t have integrity.” “Why not?” “He lied to me.” “Well, let’s go talk to him.” “No, I didn’t lie to you.” Whereas: “You just put out that tweet.” There’s no backing off that.
Facebook famously had “move fast and break things.”
Sam: That was really good, by the way. Hall of fame.
Ben: Hall of famer for sure. One of the few.
Sam: I thought about that for months. It’s so counterintuitive. I’m an engineer. I make things. I don’t break things. But it was just his way of saying: there is no excuse for not shipping. We’re going fast.
Shaan: But they don’t have that anymore, do they?
Ben: Well, they got bigger, and speed wasn’t their main thing they were trying to achieve.
Sam: They literally changed it to something like “Move with stable infrastructure and reliability.”
Shaan: Somehow lost its edge. [laughter]
Ben: Yeah. Yeah.
Shaan: Have you seen anything like that — a behavior when you walked into an office that had that same power?
Ben: Amazon had this thing where they made the desks out of doors and 2x4s.
Sam: I tried doing that by the way. It’s actually way cheaper to just get a desk.
Ben: Way cheaper to get a desk. But the idea back in the late ’90s was: we’re not wasting anything. Those kinds of markers are very powerful.
One of my favorite examples was actually from the Haitian Revolution. Toussaint Louverture basically made a rule: you can’t cheat on your wife. Which was so absurd, because here they are in a French colony — the British, the Spanish, the French are all raping and pillaging, all these armies. And these guys can’t cheat on their wives.
But that little cultural idea — this is about trust, I’ve got to be able to trust you, and the people have to be able to trust you — ended up really influencing the war. What was surprising to people who read about the Haitian Revolution was that here’s this slave army taking on European colonies, and the white women in the colony supported Toussaint against the French. And you go, why’d they do that? Because they didn’t rape. They didn’t pillage. These guys were super polite. They behaved in a certain way.
The legend is — slaves didn’t have last names, so where did Louverture come from? The story is Napoleon, who was furious, brought his generals together and said, “How in the hell can you not defeat this slave?” And they said, “Well, we get him backed up, we get him surrounded, and then all of a sudden there’s an opening.” And he became Toussaint L’Ouverture — “the opening.” And a lot of people say that opening was created by the townspeople, the women, who were just like, “No, we’re for him. I don’t give a shit about your army. We’re for that army.”
So the culture can be super influential.
Jeff Bezos’s $6 Billion Seed Round and the Return of the Builders [01:10:00]
Sam: You mentioned Amazon. Did you see Jeff Bezos got a new startup?
Shaan: Oh yeah.
Sam: Yeah. Project Prometheus — they raised an initial seed round of six billion.
Ben: Is that true? They called it a seed round?
Sam: Well, yeah, it’s the first round of funding. $6 billion, 100 people, and they’re building AI for the physical world. Not just robots, but basically the manufacturing of airplanes and ships and things like that. AI for advanced manufacturing. And he’s back in an operational role for the first time. Which is cool.
Ben: Yeah. How great is it that the logistics genius of our time is back at it and going to help us get back in the manufacturing game? Those things are incredible. And I think all of us were a little sad when Jeff was just living his best life, because he is so talented. So this is very great news.
Sam: I loved it. I was like, this guy’s having fun, he’s getting jacked, he’s showing a different north star, which has also kind of taken over tech.
Ben: And by the way, whatever people say — he is for sure a top two or three best CEO in the last 40 years.
What Makes Ben Tick: Balance, Trauma, and “Life Isn’t Fair” [01:13:00]
Sam: You’re a bit surprising to me. I’ve read all your books. I know about your background — you’ve guided people who have shaped destiny, and you’ve also shaped destiny yourself. But you’re a shockingly fun hang. Normally people with outsized results have very strange personalities. And I’m sure you have your quirks, but you seem shockingly well-balanced for how not-normal your success is. Is there anything in your day-to-day that you recognize probably isn’t normal?
Ben: Well, yeah. I would say probably the thing my daughter always says is unusual about me — and I think it came from the beginning of my life — is that I’m different than modern people. I was married when I was 22. I had three kids by the time I was 25. I had to grow up fast. And then I had the company and was trying to raise the kids at the same time, no money for nannies or anything. But what she says to me is, “Dad, you’re at the top of Maslow’s hierarchy. You’re very zen with all this.”
I take things for what they are. I’m pretty good at not being unemotional, but not letting my emotional reaction control my behavior.
Sam: Were you always that way, or did you become that?
Ben: No, no, no, no, no. Definitely not. I think it was just all the trauma that forced me to learn it.
Shaan: What age? Was it age, kids, success — like “look, I’ve made it, everything else is just icing on the cake”?
Ben: I think it was the combination of the kids and the company. The first company I founded, LoudCloud, which then became Opsware, was so difficult that in life since then — we’ve had difficulties building the firm, whatever — they never got a rise out of me that could compare to what I’d already been through. It’s almost like — my friend Oliver Stone was in Vietnam, and you could tell everything about him was defined by not being in Vietnam anymore. And I feel like — I don’t want to compare it to war, because people always criticize me for my war metaphors — but it’s kind of that feeling where it’s like, okay, I’ve been through that. I’m just looking at the world differently now.
Sam: Were there any other wisdom accelerators? Formative experiences besides the kids and LoudCloud?
Ben: Okay. So when I was a kid, I was in this relay race and it was a very big deal to me. We came in second because the team that came in first dropped the baton — the guy just ran without the baton — and they gave him first place and didn’t penalize it.
My father wasn’t at the race. And when I got home he asked, “How’d you do in the race?” I said, “Well, we came in second, but it wasn’t fair.” And I was going to explain why. And he said, “Stop right there. Life isn’t fair.”
That shocked me at the time, but it really stuck with me. It’s the single best lesson I ever got in my life. And I see young people wreck themselves so much because they have an expectation that something about life is going to be fair. Nothing about life is fair. It’s not fair where you’re born. It’s not fair what race you are. The job interviews aren’t fair. The tests aren’t fair. Nothing is fair in life.
And so the way you succeed is you don’t have that expectation. You just deal with it as it is. The whole time with LoudCloud, when the dotcom crashed and half our customers went out of business — it never crossed my mind to go, “This isn’t fair.” It was just: okay, I have to deal with it. And that is the single best piece of advice and way of looking at life that you can have. It is what it is — and do what you can do with it, being as it is.
Hip-Hop History and the Paid in Full Foundation [01:20:00]
Sam: You’ve referenced a lot of really cool stuff — the Haiti story, history outside of work. What interests you right now? Shaan and I like to talk about just fun stuff you’re into. I’m constantly reading about World War II. What about you? Is there anything you’re obsessed about?
Ben: Yes. I’ll give a plug for it. I have this charity I created with my wife called the Paid in Full Foundation, which basically gives pensions to the old hip-hop guys. They get $100,000 a year. And then we have this award show for them where we name them Grand Masters.
The first winners were Rakim and Scarface, and then we had Grandmaster Caz and Roxanne Shante and Kool G Rap and Grand Puba. And this year we added the Quincy Jones Award for the guys who got sampled the most. We gave it to George Clinton. The event was so amazing — I’m still thinking about it.
George Clinton knows all the words to “Follow the Leader.” So he’s on stage and Rakim says, “Can you rap ‘Follow the Leader’?” And George Clinton wrapped it, and Rakim came out and rapped it with him. George Clinton and Rakim. And then Dr. Dre brought a table to the event and couldn’t help himself — he goes up on stage just to say, “Look, I have no career without George Clinton.” And it was just so amazing to have all these guys who were so important, who influenced so many people, just being that appreciative of each other.
Hip-hop is so competitive, they’re always going at each other. But to be at the point where they could just go, “Man, you guys meant so much to me” — that was very special.
Shaan: That’s so cool. That idea of pensions for the OGs is so great. Where did it come from?
Ben: So I was listening to the Jay-Z song “H to the Izzo” where he says, “I’m overcharging for what they did to the Cold Crush.” And I was like, who was the Cold Crush? It turns out it’s Grandmaster Caz. And Grandmaster Caz wrote “Rapper’s Delight” basically — and they stole it from him. They stole it so blatantly that they didn’t even change the words. Big Bank Hank raps, “I’m the G-R-A-N-D Masterrapper” — but Big Bank Hank isn’t named Grandmaster. Why is he calling himself Grandmaster? Because he stole Grandmaster Caz’s rhyme. He never got paid and never got credit for it. And everybody in hip-hop knows this.
And Grandmaster Caz — if you meet him, he’s a star. He’s the coolest guy in the room. He dresses amazing. He’s super articulate. He can still rap like crazy today, he’s 65 or 66. And Rakim was on tour at these little clubs. I was like, “That’s Rakim. How are people treating him like that?” So that was the idea. We ought to just do it.
Getting it set up with the IRS is extremely complicated — [laughter] — but yeah, it’s been really, really amazing. And an unbelievable epilogue: Caz at the last event tells me, “Ben, I bought a house.” I said, “Oh, that’s amazing, Caz.” He said, “No, Ben. It’s the first time in my life I haven’t lived in the projects.” Grandmaster Caz — the guy who wrote the first great hip-hop song — has never not lived in the projects. And now here he is with a house in Pennsylvania, with berries in his backyard.
Sam: He’s got berries in his backyard! [laughter]
Shaan: It is pretty nuts. The people who invent the thing don’t get the thing. Shaan and I love UFC, and we see the early UFC events and these guys are badasses and they’re getting $2,000 to show up. And they still come to the Legends Awards and they’re still talking, and you’re like, “Damn, dude. This guy probably is selling insurance. He probably made $15,000 that year.”
Sam: This happens in the NBA too. This is why the culture gets kind of messed up — the old heads keep criticizing all the new players. They’re making $70 million a year and that guy didn’t make seven in his whole career. He’s like, “I’m better than that guy and that guy.” The resentment builds. And then they’re the guys doing the halftime shows and it’s bad for the product. Bad for the lineage.
Ben: Everything is a creative lineage, building on top of what came before. So it’s really cool to economically try to fix that ecosystem. The whole thing.
And it’s kind of this thought I have about capitalism — capitalism is definitely the system that lifted the world out of poverty and created the modern world. It’s incredibly powerful. But over time it does get corrupted. And even if it wasn’t corrupted, it’s not perfect. Certain things happen: you create a musical art form, you’re the guys who made it happen, it becomes the biggest musical art form in the world, and you never got paid. Capitalism shouldn’t work like that, but it’s just kind of the way it works. It’s nobody’s fault. So if you can go back and say, “Well, we’ll just correct those things” — that’s the idea.
Sam: I think you are so cool. On one hand you’re like a hard-hitting capitalist, talking about having to fire people, making really tough decisions. But then you’re also like, but we can do good by doing all this other stuff. And I think particularly in tech, people’s interests are not particularly that wide.
Ben: Yeah. People get very into tech. Tech is so deep and vast that people can get stuck in it. For sure.
Sam: Well, Ben, we thank you for coming on. I know you’ve got a lot of things going on, but this was a lot of fun. I appreciate it.
Ben: Yeah. No, it was a good time. Thanks, guys.
Shaan: Definitely. Appreciate you.
Sam: That’s the pod.