Lenny's Podcast: Product | Career | Growth
00:27:51 · Keith Rabois, Lenny Rachitsky
[00:27:51] S0: Yeah, absolutely. [00:27:53] S1: Okay. I want to talk about something else. I asked a few people that know you well that work with you at various companies what to talk to you about. And one person said that when I asked him what to talk about, he said, "My immediate reaction is that he is a bar raiser. No matter what kind of numbers we put up, he pushes us to do more. In fact, often it seems like the better we do, the harder he pushes." Does that resonate?
00:28:16 · Keith Rabois
[00:28:16] S0: Yeah, I think that's true. I mean, I think, look, ultimately, I'll channel someone else's feedback, but it's in the same vein. So a friend of mine who's a CEO once asked Mike Moore, it's like, "What's the most common denominator of the best CEOs ever?" And he said, "It's the relentless application of force." Quote. I think that's the job of the CEO. People eventually get comfortable, complacent. The more success you have, the more complacent the organization tends to get, and the single role for the CEO is offsetting that complacency. So to the point, the more success you have, the better you're doing, the more complacency naturally kicks in. And unless you've erected a network effect, you do not want to get complacent. And even then, debate whether you should. But fundamentally, most businesses are not network-effect businesses. They're not going to run on their own for a long time. So I think that's one insight is the better you're doing, the more the CEO should push. Secondly, it's a little bit like sports when you're growing up. People, when they're winning, take advantage of feedback better than when they're losing usually. So for example, now what I do is mostly a VC, mostly a board member, mostly a consigliere to a founder. Maybe what's less intuitive, and you may picked up on this in your research and interviews of people who know me, when a company's struggling, I'm actually usually very non-critical and more like a coach and supporter. Because the company, the founder knows they're struggling. Being critical doesn't really help them solve the problems. That's when being supportive can actually somewhat counterintuitively be more important. But when the company's thriving, it's really important to be critical and isolating things that will eventually be problems while everybody in the company's really happy and borderline complacent. So you want to be the opposite as a default. And that's like a really good sports coach. When you're winning is when to polish everything and really master the details. When you're losing, you definitely also have to be exciting people and embracing the future and selling the future.
00:30:30 · Lenny Rachitsky, Keith Rabois
[00:30:30] S1: So is, say someone's listening, a founder or a product leader, the advice here is just keep pushing harder, set the bar higher as things, even if you're doing great? [00:30:41] S0: Yeah, if you're doing great. Well, also you have to remember, I remember giving a speech once at Square. It's like you get to a certain threshold, crazy inflection. Momentum gets you to certain valuation and all these attributes. But it's like winning a Super Bowl. The last year was great. Last four quarters was wonderful. It's like winning the Superbowl. You got to come back next year and start your records zero, zero again. And you got to remember that. Actually, Ventures like that. I'm only as good as my last investment. I've had 13 years or whatever, of pretty damn good investments. But truthfully, I have to wake up every day and find some undiscovered founder that's going to change the world. And if I don't do that, it doesn't matter what I've done in the last 13 years. And a company's like that and the company can skate on autopilot for a while. Venture, you really can't ever skate. [00:31:33] S1: I definitely saw this with Brian Chesky. He just felt like things were going great. And we just shipped amazing products and growth is up and he's just always pedal to the metal no matter what. Just like, "Come on, when are we going to take a little break?" And it's interesting because when we did have little breaks here and there, morales actually went down because people are like, "What am I working on? I don't know. It's not that exciting."
00:31:33 · Lenny Rachitsky, Keith Rabois
[00:31:33] S1: I definitely saw this with Brian Chesky. He just felt like things were going great. And we just shipped amazing products and growth is up and he's just always pedal to the metal no matter what. Just like, "Come on, when are we going to take a little break?" And it's interesting because when we did have little breaks here and there, morales actually went down because people are like, "What am I working on? I don't know. It's not that exciting." [00:31:53] S0: Yeah. Brian and I are usually in sync a lot. There's a really good interview when I interviewed him also at the same conference of how to hire, when he talks mostly about founder mode. But I generally subscribe to virtually all of Brian's views. He even taught me some of these things himself. But the more important point I think you identified, which is very subtle, is really talented people are like superb athletes. And when things are going well and people are really coasting, they're not happy. They have an internal clock tempo. They just want to create things and create value and drive, drive. And the morale actually does go down for the best people in the world when people are skating.
00:31:53 · Keith Rabois, Lenny Rachitsky
[00:31:53] S0: Yeah. Brian and I are usually in sync a lot. There's a really good interview when I interviewed him also at the same conference of how to hire, when he talks mostly about founder mode. But I generally subscribe to virtually all of Brian's views. He even taught me some of these things himself. But the more important point I think you identified, which is very subtle, is really talented people are like superb athletes. And when things are going well and people are really coasting, they're not happy. They have an internal clock tempo. They just want to create things and create value and drive, drive. And the morale actually does go down for the best people in the world when people are skating. [00:32:37] S1: Okay. So actually along those lines, there's a lot of anxiety in the market, in the job market about the future of careers. Am I going to have a job? Where are things going? And it just feels like people are working very, very hard. They're just putting in a lot of hours, especially the most AI people. It just feels like they're working harder than ever. I don't know if you saw this thing Tyler Cowen put out of just work harder. Now is the time to work harder because AI is eating away at your value. You probably talked to a lot of people looking for career advice of just like, "This feels scary and I feel like I'm working too hard and what should I do?" I don't know. Do you have any just advice for folks from-
00:32:37 · Lenny Rachitsky, Keith Rabois
[00:32:37] S1: Okay. So actually along those lines, there's a lot of anxiety in the market, in the job market about the future of careers. Am I going to have a job? Where are things going? And it just feels like people are working very, very hard. They're just putting in a lot of hours, especially the most AI people. It just feels like they're working harder than ever. I don't know if you saw this thing Tyler Cowen put out of just work harder. Now is the time to work harder because AI is eating away at your value. You probably talked to a lot of people looking for career advice of just like, "This feels scary and I feel like I'm working too hard and what should I do?" I don't know. Do you have any just advice for folks from- [00:33:15] S0: Well, I do think AI is going to radically reorient lots of people's careers, maybe including mine. So I think that's actually true. And I think the way to thrive in a rapidly emerging technology world is to be intellectually curious. So for example, I'm a business person historically. I did actually code when I was really young, but basically professionally, just a business person. What I've noticed in some of the best organizations is the number one consumer of tokens is the CMO- [00:33:15] S1: CMO.