The Exchanges

Q and painful to be a CEO, to be a founder. Uh, in spite of that, so many people want to start companies. So many people like dream of having their own company. What do you, who, who is not right to start a company? Like what advice do you share with folks that are thinking about starting a company that may not understand just what they're about to get into?

A Yeah, so it, it's funny. So there's a couple of things, you know, John Reed, who is the CEO of Citigroup when I, when I started as CEO, said to me something I never forget. He said, Ben, the only reason to start a company is because you have an irrational desire to do so, because it's not worth the money. And, you know, I was like, wow, he doesn't, he didn't even quantify how much money, and this guy's running Citi, so he's a very numbers banking guy. And you didn't quantify it. And, um, I remember when we sold loud cloud for 1.6 billion dollars, I remember thinking, wow, that wasn't worth the month. So I think if you're doing it for the money, uh, that's a very bad reason and it'll be extremely difficult to get to an outcome. You really have to have an irrational desire to do something larger than yourself to kind of improve the world in some way, um, that, You know, somehow like that is your purpose, and if you don't feel that, uh, then you'll never get through it. It's just too many, too many bad things happen along the way.

AI assessment note: “if you're doing it for the money, uh, that's a very bad reason”

Q uh, as a great exemplar of great culture in the prison gang that he ran. Uh, so interesting, but, uh, something that he learned from you that he told me I need to ask you about is about success and how to be successful and how it's not what people think. And he said that you learned this lesson from a pilot. What is that story? What is that lesson?

A Well, it's kind of, I, I mean, I, I, I'd say it's a long life lesson, but the, the pilot story is, um, I actually, you know, I asked people like silly questions sometimes when I meet them. And so I, you know, I met this gentleman who was a pilot and I, you know, it was right around the time, uh, JFK Jr. crashed his airplane, uh, and, and ultimately died. And I asked him, I was like, you know, like what happened? Because there's always You know, the story in the press, and I know this from them writing about me or anything is it's always what's the best narrative, not what's true. So you can never kind of actually find out what happened. You just find the, like the best story version of what happened. Uh, and you know, the story in the press was all about, oh, he wasn't trained on instruments. Instrumentation was flying at night. And I wanted to know, is that right? And the pilot said, well, he said, really, it's like all plane crashes are a series. Of bad decisions. And none of the decisions by themselves is that bad, but when you add them up, it's bad. So the first decision was he needed to get wherever he was going, and that was the priority. And in flying, that can't ever be the priority. Uh, you know, because there are conditions, there are things that happen. And then the second one was, well, like his timing of when the sun would go down was wrong. So he thought he'd be f…

AI assessment note: “the pilot story is, um, I actually, you know, I asked people like silly questions”

Q Kind of going back to the origin story of A-sixteen Z, something you guys were really big on was helping founders stay COs, become great COs, not replace them with professional COs. I wanna, I wanna flip this question on you. When does it actually make sense to replace a CO? When are people not gonna make great COs?

A It really, the, the, there's a very consistent thing that happens, which is, um, you know, when somebody doesn't make it and it kind of starts with confidence is the way I would put it. So when, like if you, you're, you invent a product, you kind of recruit a team, so forth, all of a sudden you're a CEO, but you haven't run a big organization. You don't know how to do that. Like most founders are like that. Um, and so If you don't know what you're doing, you're gonna make mistakes, and they all make a lot of mistakes, and then when you make those mistakes, they're very expensive, you know, like they could cost you to do a down round, or they could cost you to lose a company, or they could cost you a customer, or, you know, you screw up the product, like they're very high impact, and not just on you, but everybody who you talked into joining you, and so that kind of motion can really cause you to lose confidence, uh, and then if you lose confidence, What happens is you hesitate on the next decision. And, you know, as we talked about, like hesitation is very dangerous because one, like it, it locks up the company, but even worse, what happens is if you have senior people working for you, they get very nervous and they feel like they need to jump into that void and make the decision for you. And that's when it gets political. Like very political because people are like vying for p…

AI assessment note: “that's generally where like, okay, the founder probably can't run this thing anymore”

Q Uh, two more questions. One, do you have a, is there like motto that you often come back to find really useful in worker in life?

A The thing that I would say has had the biggest effect on me is something my father said to me years ago, um, which is life isn't fair. And that, that seems like really, really simple, but I think that, um, the thing that defeats people more than any other thing that I've seen just in life is the expectation of some fairness. Uh, you know, like it's just not fair. And there are, like, all kinds of stuff that are going to happen to you that You know, and happen to everybody, um, that don't happen to other people that are completely unfair, but it doesn't matter because that's the way it is. Uh, and as soon as you get that idea out of your mind, um, then you can just deal with it. Like, oh yeah, of course it's unfair, but I'm going to, what should I do now? Which is the real question, not how do I go back and get people to be fair? Cause nobody's going to be fair. It's not fair. It's the nature of it. If you think about it for more than five seconds, you'll realize that. And I think a lot of, uh, you know, and it's as an individual, like if you want to make the world a better place, whatever, but for, as an individual, do not expect anything to be fair. It'll only defeat.

AI assessment note: “is something my father said to me years ago, um, which is life isn't fair.”

Q There's something that you mentioned there in your answer about the PM being the leader. There's always this kind of sense that the PM is not the mini CEO. How dare you call yourself that? I actually think that's exactly what the PM is. They're basically the closest to the CEO. Their kind of job is to think like the CEO within the team.

A Yeah. People get mad, you know, like, cause Everybody, you know, like this is the whole challenge of management in general. Like people get jealous over student shit, but like from, from the perspective of the PM, like it doesn't matter if you write a good spec or you have a good interview or you do this or do that. Like what matters is that the product wrench and you have to get all the way to there and kind of work backwards from that and You can't do that without leadership because it is about, okay, we want to build that, and, and you're not necessarily the person that comes up with every idea or this or that, I mean, you're just the keeper of the vision, you know, and that's true for CEOs too, like, you don't want every idea in a company coming from the CEO, like that's, I think it's a misunderstanding what a CEO is, is why people don't like that. They don't know what a CEO is. But a CEO isn't the one who has every idea, gives every order, does every, that's not the way it works. The way it works is there's somebody who's got to consolidate, you know, get all the good ideas, prioritize them, decide which good ideas we're going to do, and then get everybody on the same page so that they have very high fidelity and understanding of what that is. And, you know, so that it is a CEO kind of function. Now, it doesn't mean, like, I'm better than you. It just means, like, that's w…

AI assessment note: “so that it is a CEO kind of function.”

Q Along this AI thread, something that is really important to you clearly, something you talk a lot about is, is the US being successful in AI and be in leading the world in AI. Why is it so important? Why is something you spend a lot of time on?

A It starts with, uh, I think my view of the US, uh, and its role in the world. So It's, my personal view is like, it's very, very, very important, not for society to be completely fair, because it's not going to be completely fair, or completely equal, because we've never had one that's been completely equal. But it's important that everybody have a chance, um, at life, you know, and particularly, uh, you, you know, kind of both culturally, but also just like you, you can't advance the world if, you know, you can't tap into all of your resources. And so if you kind of take away motivation and these kinds of things, you get into trouble. And if you look at the kind of every country today, and this is by the way, um, so you want like the right amount of decentralized power. Um, you know, you don't want it to be completely concentrated. Concentrated power makes it very, very difficult for everybody to have a chance. This is the big kind of lesson of communism over the last hundred years is it turned out right. And, and, you know, we saw politicians selling it this way today. It's like, oh, it's power to the people. No, no, no. It's power to you, because you're removing all power from the private sector and installing it into the government, and then you're putting yourself in charge of the government, and so I become extremely powerful, and this is why it didn't matter if it was Ma…

AI assessment note: “It starts with, uh, I think my view of the US, uh, and its role”