Lenny's Podcast: Product | Career | Growth
01:14:02 · Lenny Rachitsky, Keith Rabois
[01:14:02] S1: When people hear this, it may feel like, "Oh, wait," it feels aggressive to be criticized everyone public comment. Any advice for just how do you not make it this, I don't know, scary environment or is that part of it? [01:14:14] S0: Well, I think you want to win. And there's probably in art to this, I would say some of the best coaches in sports probably do a bit of both. There's things they will say in front of the team. And then there's things that probably channel to the individual player. So there's probably a mix. It could be very effective too. [01:14:33] S1: It feels like you're not focused on psychological safety as a core tenent. [01:14:38] S0: No, no, I don't believe in that at all. High performance machines don't have psychological safety. They're about winning. [01:14:46] S1: Bam. [01:14:47] S0: For those who want to ... A good book that's off central casting for you is read Jordan Rules or watch The Last Dance, if you like, but fundamentally, read Jordan Rules. If you want to be Michael Jordan, you got to act like Michael Jordan. [01:14:59] S1: Do you feel like that's negatively correlated to this idea of psychological safety with success? There's just- [01:15:03] S0: For the most part.
01:15:03 · Keith Rabois, Lenny Rachitsky
[01:15:03] S0: For the most part. [01:15:04] S1: Yeah. Interesting. I'm going to take us to failure corner. Okay. So failure corner, so that you talk about all these things you've done that are incredibly well. All these companies you invested in, all these businesses you've built, PayPal, all these things. People don't realize there's also a lot of failures along the way. Is there a story of a time you failed in your career or investing that might illuminate the doubt when things don't go great?
01:15:28 · Keith Rabois
[01:15:28] S0: Well, I mentioned one, I alluded to one by accident. I talked about being acquihired or whatever into Google and being stuck there. So clearly not successful. That was a slide. So we did sell for 187 million, but nowhere near the ambition, didn't really achieve any of our goals product-wise or company-wise. Investing teaches you mostly about failures. If you're a world-class investor in the early stages, 30 to 40% hit rate is great and golden. By definition, that's 50 to 60%, 70% failing. It's a little bit like those old Nike commercials where there's the Michael Jordan one where it's like, "I've missed 109 game-winning shots in my career." Or there's the tennis one. I think it's Federer that's like something like, "I win 60% of my points. Actually, I'm not the best tennis player ever, but I lose 40%." So there's a lot of that in venture. You definitely have failures all day long. I think one of the arts is not getting too caught up in failure, actually. I think over ... and I actually gave this feedback in the board meeting recently, which is someone well-meaning one or two board members were like, "Well, let's do retros on our failures." And the company's doing really well. So I was like, "You know what? Honestly, I'm not sure I would do this." I was like, "I don't want to deter people from taking ambitious shots on goal." And if you overemphasize failures and people think they're going to get criticized, this is where psychological safety maybe has some validity, which is be ambitious, be bold. Don't worry about the failing part unless there's things you miss that could have been factored in, but you want people to take risk and you want people to be excited about raising their hands for very difficult problems and challenges because that's how you create value. And so I was like, "No, let's really not do these retros. Let's just focus on winning."
01:17:28 · Lenny Rachitsky, Keith Rabois
[01:17:28] S1: Contrarian takes all around. Keith, is there anything else you wanted to share, anything else you want to leave listeners with before we get to our very exciting lightning round? [01:17:36] S0: I'm excited for your lightning round. This is usually one of the best parts of your podcast. [01:17:39] S1: Okay. First question, what are two or three books that you find yourself recommending most to other people? [01:17:43] S0: So the number one one is called The Upside of Stress by Kelly McGonigal, Professor at Stanford. And basically it argues in an incredibly compelling way that if you want to be happy, healthy, or wealthy, you need more stress in your life, not less. So it's magic. The evidence she marshals is effectively uncritiquable at the outcome level, at the biochemical level. It is transformative to people to read this book, so I highly recommend it. [01:18:10] S1: Favorite recent movie or TV show you've enjoyed? [01:18:14] S0: TV actually just watched Nuremberg Trial. Highly recommend Nuremberg. There's a lot of lessons there that are applicable to the modern world, so I won't spoil it all, but even I'm kind of a student of history and politics and watching the movie, I've probably learned five or 10 things that I never knew before. Highly, it's extreme ... And I mean, obviously it's not an exciting, thrilling movie, but it's an extremely well-produced movie and incredibly useful to understand some of the travesties of history and how to prevent them in the future. [01:18:55] S1: Where do you find this? Is that one of the streaming services?
01:18:55 · Lenny Rachitsky, Keith Rabois
[01:18:55] S1: Where do you find this? Is that one of the streaming services? [01:18:58] S0: It's either on Netflix or iTunes or both. [01:19:00] S1: Sweet. Okay. Is there a product that you've recently discovered that you really love? [01:19:06] S0: Rarely. I do find products that I'm addicted to. I'm on this crusade about Eight Sleep, which is another one of my conventions is you must sleep eight hours a day, you must prioritize sleep even when you're very busy. I am an investor and so I'm somewhat biased in Eight Sleep, but it transforms people's lives. So I'm still addicted to that one. I don't know if there's a new product that I've been fanatically addicted to recently. [01:19:34] S1: Eight Sleep counts. Do you have a life motto that you find yourself coming back to in work or in life? [01:19:40] S0: No days off, #NoDaysOff. I don't believe in taking days off for workout. I don't believe taking days off from work, period. Derivation for those who are interested is when Bill Belichick won the Super Bowl for whatever billionth time with the Patriots. As back to back Super Bowl wins, I think he started the championship celebration parade with this chant of, "No days off." So that's kind of my mantra. And [01:20:06] S1: When you say, "No days off," are you saying, "Work every day, work the weekend," sort of thing, or what do you ...
01:20:06 · Lenny Rachitsky, Keith Rabois
[01:20:06] S1: When you say, "No days off," are you saying, "Work every day, work the weekend," sort of thing, or what do you ... [01:20:12] S0: That too. So let's talk about the workout side. I believe I've missed seven days and seven years of working out. And it still kills me. Half of those I still am annoyed that I missed. If I really, really had reoriented my schedule, I should have been able to hit at least four of those. And I measure it and I post it at the end of every year. Last year I missed none, so I was very happy, but I don't believe in excuses basically. No days off is a proxy for I don't believe in excuses. [01:20:38] S1: And do you work out every day? Is that the role? [01:20:41] S0: I mean, literally there's only seven days in the last seven years I haven't worked out. [01:20:45] S1: Okay. I see. [01:20:45] S0: That includes all kinds of illness, sickness, travel, international, time zone, travel- [01:20:50] S1: So it's actual okay. [01:20:50] S0: ... weddings. There's no excuses. [01:20:53] S1: Actually every day. All right. And then- [01:20:56] S0: Typically more than once a day. [01:20:57] S1: And you've told me before we start recording, you had a Barry's class this morning. You have another one later today. [01:21:02] S0: I do. And a lift. [01:21:04] S1: Okay. Final question. So you were famously part of the PayPal Mafia. I'm curious if there was someone there that's over-performed, someone that you worked with that you never thought would be that good.