The Exchanges

Q is life about happiness? It's about impact. You can have an impact on Uber, which is a really important company in the world that's shaping the future of cities. And I thought, thought to myself, my God, this is so obvious. I've got to take a shot. I knew it was going to be uncomfortable. Can you just explain how you think about optimizing for impact or happiness and why?

A Well, first off, it's, it's incredibly kind of Dara to say that, um, You know, I, I think about this. I think happiness is a trailing indicator of impact. And, uh, I think you can be, you know, you can feel happiness in small bursts, in small moments, uh, and you can have a lot of variance in your life. So you can choose to have that part, which is the ups, the downs of life, et cetera. So I'm not saying you can have happiness, but I think truly sustained happiness comes from, uh, impact and impact is something that's deeply personal to you. Uh, only you can define what What impact means for you. Um, so I think it means different things for different people, but I do think it's a trailing, um, indicator. So the way, uh, you know, I would put it in this case is, you know, what was obvious for me, uh, with someone like Adara, uh, was he was content. He wasn't happy. And, um, you know, he had gone through a phase, um, knowing him for a while where, uh, he had a lot of ups and downs with Expedia and all that stuff. And he kind of mostly figured it out, and so he was content. And I think that in his case, you know, where he was at his life, um, it was such an obvious thing that he didn't even realize that he'd just grown content. And so, for me, um, you know, Uber is a very special company, and to even be asked to be the CEO of that, and the impact I knew he could have on that compa…

AI assessment note: “I think happiness is a trailing indicator of impact.”

Q Were you content after you sold your first company? You were like, 22, 23.

A Well, content is the right word. I wasn't happy. Uh, so I was content for a moment of time. I was 22. Um, I never had much, much success with, with women, uh, because I was a computer geek and back then computers was not the coolest thing, uh, in the world. And, um, you know, so I, I was like, okay, well now I've got all this money and, uh, you know, this, this was my worldview. I can go out in nightclubs and I'm going to be the cool guy. Um, and I had fun for a while. I'll tell you that. But, um, it also was incredibly, um, hollowing because, um, you know, I realized that these girls, uh, weren't with me because of me and they were with me because, you know, I had status. And I was able to use money to buy status, uh, and be a cool guy for a small moment of time. And so, um, that taught me a lot, right? And, and actually, you know, I kind of walked away for over a year, not doing anything at all, um, and just sort of deeply reflecting on life, uh, what I wanted to do, because for me, you know, I had a magic, um, number. Which was ten million. If I got that number, I would retire. That was the goal. And I was thinking to myself.

AI assessment note: “Well, content is the right word. I wasn't happy.”

Q because they also had it. So I'm very curious. Do you feel different? Um, and what I mean by that is, like, as you've grown from, you know, a kid in the projects, even if you had early success, to now being, you know, one of the most successful entrepreneurs on the planet, which I know, don't do the face, but it's an undeniable fact, like, do you feel different?

A I think yes and no. Um, so I, I feel different in, in the same way a 40 year old would feel different than a 10 year old would do. I feel different in, um, I'm a product of all the experiences of my life, and obviously I've been incredibly fortunate to, uh, I was counting the other day, I've been to like a 130 countries or something in my life. I've seen so many cultures, so many people, I have friends all over the world. All of that has shaped me into who I am. Um, I don't feel different because innately many of the things, the drive, the long-termness, the obsession, the, um, uh, This sort of willingness on the paradox of winning on the one hand, but then also trying to truly find a win-win, um, and work with people to try to find a win-win, which is really important to me.

AI assessment note: “I think yes and no. Um, so I, I feel different in”

Q Like, we can't, we have to talk about quality, so like, do you want to, like, just pick up where that quote leaves off?

A Well, there, there's so many strands of quality, right? Um, um, it is both, um, sort of the distinction of taste, whether taste is subjective or objective, you can go so many ways with this question. But, um, the way I think about quality, um, is, um, I think so much of your early life, um, certainly my case was the formulation of just trying to go for more. And the further I've gotten, uh, I've realized, um, and, and it's about everything, right? You mass more stuff. Uh, you mass, uh, you try to do, uh, you know, more things at the same time. You try to do all of these things, um, at the same time. And the further you go, you realize that, um, It, it, it really is about sort of ultimately this very simplistic try thing, less is more. And, and the older I get, I feel more and more. Um, you know, we talked about it with friends. Um, I think most people, uh, start out thinking having more friends is better, but I think more people are happier with fewer but better friends than many friends. Um, and, and so I think quality is ultimately this sort of notion around, um, Focusing, um, distilling, uh, getting to the essence. Uh, we can even talk about, like, quality in communication is often trimming things down and saying less things, right? Um, why is it, for instance, that when we're talking about very hard things, most people's instant reaction is just to try to add more complexit…

AI assessment note: “the way I think about quality, um, is... focusing, um, distilling, uh, getting to the essence.”

Q the first time there was gonna be all these, like, crazy colors and everything else, like, and Johnny tells the story, he's like, you know how we chose the colors? He's like, me and Steve went to the design, like, where, the Apple Design Center, and we talked about it, and 30 minutes later, the colors you saw, we shipped. That was it. Where are you on, like, that spectrum?

A Yeah, I think the most important thing that, uh, you described is it's a spectrum. It's not a hundred percent, um, you know, one way or the other way, because again, sort of like, I remember early on, um, you know, people talking about that sort of dichotomy of how Google does things and how Apple does things, and many founders then tended to gravitate when Apple was at sort of peak Steve Jobs to, no, I run the product review, it's only my opinion that matters, um, and it's my taste, and I've got this articulation, all these things. And lo and behold, like, uh, some terrible decisions, uh, ended up, uh, coming out of this, et cetera. And, and I think where people, um, sort of break down on almost all issues is they take it literally. I don't believe for a second that Apple was a hundred percent in the camp where Steve Jobs just had universally the answer to everything. He didn't listen to anyone else's opinions. He didn't try things out. Sometimes maybe trying it out by testing his ideas on multiple people inside and outside, um, you know, et cetera. But of course he did that. Right. And I know one of the ways he did it, which was brilliant and that don't get talked about. He actually called up journalists. Sometimes, and tested ideas on them, and, and like, we might do this, um, kind of thing, and then hear the journalists react to it, and it's like, okay, that was a bad idea,…

AI assessment note: “it's a spectrum. It's not a hundred percent, um, you know, one way”

Q because 80% of your customer intelligence is invisible, hidden in emails, transcripts, and conversations. Unless you have HubSpot. HubSpot is where all of your data comes together so you can see the patterns that matter. Because when you know more, you grow more. And that is a pattern that never fails. Visit HubSpot.com today. That is HubSpot.com. Are there any product updates that get pushed live that you didn't like?

A Oh, plenty. Um, plenty. And, and, and this may be a little bit unique, but you know, coming back to it. So, you know, I, I ended up, um, Having, you know, so, so the typical thing is that the founder needs to be the product person, right? Um, by the way, it's a hundred percent true. I, I totally believe that. I think it's the most important thing in the zero to one stage. But what a lot of people don't talk about is the fact that there isn't one stage of this journey. It's like you're oscillating between zero to one, one to a hundred, and then, you know, the last stage was more like optimization stage. And you have to like constantly do that. And you're going to need different skills at different places. And this, this is why, by the way, I believe it's so important for entrepreneurs to realize when to apply what tools, um, in this journey. So what happened with Spotify is sort of against all the common wisdom and wealth, which is I don't really run product, um, anymore. Um, because what happened was I got this guy called Gustav that you now met and he runs product. And he's actually way better than me at doing it. And so, uh, speaking about sort of being truthful, what ended up happening, uh, many years ago was, um, I was running these product meetings. Um, he was sort of running it, but I, I wanted to run it, so I kind of interjected myself over him. Um, but I didn't have the…

AI assessment note: “Oh, plenty. Um, plenty. And, and, and this may be a little bit unique”