Ravi Gupta: The Realities of Success

One of the main jobs Ravi Gupta has as a partner at venture capital giant Sequoia Capital is to help founders see the difference between fantasy and reality. On this episode of The Knowledge Project, Gupta dives deep into a wide range of topics that will help you better understand the realities of success, decision making, why it’s crucial to practice doing things you don’t want to do, the best advice he ever received, and the value of quality over quantity. Gupta has served as a partner at Sequoia Capital since 2019. Prior to joining the world of venture capital he served as the Chief Operating Officer and Chief Financial Officer for Instacart, and he also spent a decade working in private equity with KKR & Co. -- Want even more? Members get early access, hand-edited transcripts, member-only episodes, and so much more. Learn more here: https://fs.blog/membership/ Every Sunday our Brain Food newsletter shares timeless insights and ideas that you can use at work and home. Add it to your inbox: https://fs.blog/newsletter/ Follow Shane on Twitter at: https://twitter.com/ShaneAParrish Our Sponsors: MetaLab: Helping the world’s top companies design, build, and ship amazing products and services. https://www.metalab.com Aeropress: Press your perfect cup, every time. https://aeropress.com Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  If what it takes to be the best in the world at the thing that I'm doing is to lose some of those aspects that we're talking about, then I don't want it. Number one is the family and it is sort of what Avni and the kids are going to say. And maybe I should say I'm kind of fearful that what you just said is true, but I'm not fearful enough to change it, you know?

• 0:39Shane Parrish?

  Welcome to the Knowledge Project. I'm your host, Shane Parrish. This podcast is about mastering the best of what other people have already figured out, so you can apply their insights to your life. Don't miss out on exclusive content and early access to your favorite podcasts by joining our membership at fs.blog/membership, you'll unlock special episodes unavailable anywhere else, hand-edited transcripts from each conversation, and support the podcast you love. Visit the show notes for a link and upgrade your listening experience. Today, my guest is Ravi Gupta, who has mastered the art of balancing quality and quantity in both investing and life. From his time at KKR to steering Instacart through pivotal moments, and now as a partner

• 1:22Shane Parrish?

  at Sequoia, Ravi has not only accumulated insights, but as you'll see, he's put them into practice. After talking with Ravi on the phone a few times, I found myself coming back to parts of our conversation over and over again, and I wanted to know more. In this episode, we dive into the best advice he's ever received, the importance of keeping the main thing the main thing, and the reasons even exceptional people fail. Get ready to be inspired and learn from his unique perspective on life and success. It's time to listen and learn.

• 2:07Shane Parrish?

  What's the best advice you've ever received?

• 2:10Speaker 00

  And it's from my dad, right when I first started working. And he said, listen, son, don't have a work personality and a home personality. It'll just tire you out and, you know, you don't want to have to live two different lives. And, you know, I'm sure there are way better versions of advice from when I was a kid or any of that around integrity and, you know, all that. But the piece of advice that just came to mind when you asked was that one.

• 2:35Shane Parrish?

  Have you worked with people who seem like two different people? One person at work and one person outside of work?

• 2:41Speaker 00

  Yes, 100%.

• 2:43Shane Parrish?

  How does that make you feel?

• 2:44Speaker 00

  I think the first thing is you're surprised when you see them in the home environment. Cause you have this vision of the way they are. And then you see them in a different environment. And let's just say they're very, you know, tough at work and then they're different at home. They're understanding, they're, you know, uh, they're smiling more, whatever. So I think the first thing is surprise of, oh my gosh, this person is so different than what I expected. And then I think the part that is bad is you're sort of like, why don't I get that person? Man, I would love to work with that person, you know? And this is where I think COVID was sort of interesting because like in COVID, you actually did mix that up a little bit more.

• 3:28Speaker 00

  And you'd see somebody who was generally a certain way. And then, you know, their kid would come bouncing into the room and you'd see how different they were with their kid. And it really warmed them up to you. And, um, yeah, so I think that, uh, it kind of makes you feel bad because you feel like you're not getting the real person, right? People generally are more real, I think, at home. And so you feel like you're getting this act almost.

• 3:55Shane Parrish?

  And then that, that becomes an impediment to trust too, in a way, right? Because it's like, who am I getting? How do I predict what I'm getting?

• 4:02Speaker 00

  Totally.

• 4:03Shane Parrish?

  Well, when your father told you that you you were a teenager, I'm assuming?

• 4:08Speaker 00

  I I had just graduated college. I was about to start my first real job.

• 4:12Shane Parrish?

  What what were your teenage years like?

• 4:15Speaker 00

  So I have an older brother, uh, who's three years older than me. And, uh, I bring him up because I think he was pretty impactful to my teenage years because a lot of it was in comparison to him. Um, and my brother is wonderful and kind, but he was better than me at most things. And a lot of my teenage years felt like trying to either live up to what he was good at or differentiate myself. And that, I do think it's an interesting answer that when I say it out loud because it does feel like my answer as a teenager is sort of in relation to somebody else. Um, but I was a happy kid and all that, but it it was all, I always had that in mind.

• 4:56Shane Parrish?

  Was he naturally good or did he work hard?

• 4:59Speaker 00

  Both. I think my brother has an extremely, he has a wonderful work ethic. But he also, you know, it it did come easy to him on some things. Um, and then I realized I, to your point, I tried to spend time on things that were different than what he did. So he liked baseball. He liked lacrosse. I didn't play baseball or lacrosse. I played basketball. He really was, uh, deeply studious and was into pre-med. And I was like, I'm definitely not going to be a doctor. He went to college at Northwestern, which is close to where we're from. And I said, I can't, I can't go to Northwestern. So there was a lot of that where a lot of my decisions almost felt like they were a response to his. Um, and

• 5:44Speaker 00

  the other thing is my parents are from India and I think that they have a very strong sense of what success looks like. And I'm very close to my parents, but that also informed my teenage years for sure because you know, there was a very clear message from them around like, look, you gotta, you gotta get after it. There there's laziness was like a huge, um, ding in our household. It was just so offensive, you know, to be lazy. Um, and so any moments where I had that, you know, reeked of laziness were really, uh, poorly received in my house.

• 6:20Shane Parrish?

  Are you like that with your own kids today?

• 6:22Speaker 00

  Certainly somewhat. I I think, um,

• 6:26Speaker 00

  I think what we try, let's think about this. I think for Avne and me, both of us had parents that were pretty, you know, had an opinion on the value of trying to be traditionally successful, whatever, which I think is very typical for children of immigrants. I think we probably have a slightly different view than them on that of, you know, there are probably a broader definition of things of success than what they had. But I think we both do believe that we want our kids to be happy and we think, and I certainly think that like earned success is the key to happiness. I really believe that. I heard this one time from Arthur Brooks, who used to run the American Enterprise Institute, has really sat with me. It is something I believe a lot. And so a lot of what we try

• 7:09Speaker 00

  to get into our kids is this belief of whatever you do, just make sure you feel like you're good at it and make sure that you feel like you've earned some level of success in it. And that comes from trying, that comes from practicing, that comes from doing something hard, you know. And I have no idea how successful we are at that because they're the older, there's three boys, the twins are 10 and the youngest is eight. But I would say that that is kind of the theme that we try to use as we're talking to them.

• 7:38Shane Parrish?

  I like the idea of earned success. Going back to sort of your parents' definition of success, do you think it was narrower then than it is now because you have the luxury of being broader? And I mean that in the sense of being narrow because here, this is your path out of this situation to a better life. Whereas now, when you look at your kids, you have a much broader sense because you don't, you have a lot more luxury in how they become successful.

• 8:07Speaker 00

  A hundred percent, a hundred percent. You know, everything my parents said and wanted, and Avne's parents said and wanted was out of love and it was out of what they saw as the path to the things that they would, that would make, they basically thought what would have made them happy and then applied that to us of, you know, okay, let's try to make sure that you have all that. And I think, to your point, I think that them... Immigrating to America, it was a different life than they had in India and it's a different life than their parents had in India. And I think what you just said is absolutely a luxury that we have. And that's a luxury that was largely provided to us from our parents, you know? But yeah, I 100% agree with the premise.

• 8:52Shane Parrish?

  The other thing I sort of wanted to go back to is laziness. It's like such a trigger for me with my kids. I don't know why, but any hint of laziness, I'm just like all over.

• 9:02Speaker 00

  Mine, mine is whininess. Any whining drives me nuts. And it is because I thought about this a lot. It's a huge trigger where I am irrational in my response to it. And, but the reason I think I am is I just, I really dislike whiny adults. I really dislike people that are victims. And I really have a hard time with it. And I have this thing that I just want to make sure that my kids are not like that. And so I'm sure that I'm not doing it right, but it is such a triggering thing for me when there's whining or feeling like, oh, this happened to me and kind of their, that their life happens to them versus like, no, you know, it's not a mistakes were made situation.

• 9:47Speaker 00

  It's not like, gosh, there was nothing I could do. No, we can always do something. We have agency. We are the captains of our own ship. And so I always joke with my wife that like if they're, you know, in therapy when they're older and they're telling their therapist about what their parents did, one of the things is certainly like, man, I couldn't even complain about anything. But that's my trigger.

• 10:08Shane Parrish?

  How do you talk to them in that moment about whininess? Like, what does that conversation look like when you catch them sort of whining?

• 10:16Speaker 00

  Yeah, I think, well, there's probably two different versions of it. The one that I'm not proud of is the one where I'm emotional. I'm quick. I sort of haven't taken the time to think about how exactly I want to deal with it. And I just kind of react, you know? So hopefully that doesn't happen a lot, but that's definitely one version of it. You know, stop whining, that one.

• 10:57Speaker 02

  How do I negotiate so many great travel deals? My greatest gadget, the Priceline app. It's got hotel deals, flight deals, rental car deals, all of those deals in a bundle. Deals, game day deals, concert trip deals. No one deals more deals than Priceline. Hold your horses, there's more. The app lets you filter hotels by neighborhood, vibe, star level, and amenities like pools and spas and beachfronts. Wait, I'm not done. Stop cutting me off.

• 11:23Speaker 00

  I think the one that is much better is sort of

• 11:28Speaker 00

  asking them questions. Hey, what happened here? Hey, why are you, why do you sound like that? What is the thing that actually went on? Do you think you could have done anything differently? And I think that kids, they are good at answering questions and they give you surprising answers sometimes. And what we find is if you just get them talking, it's generally much better. And the questions generally help with that. And so I'd say when I'm at my best or when we're at our best in that situation, it's much more asking them about what they think and trying to get them to get there themselves because it's the same thing, right? They have to believe it. You know, my parents have this thing of you can't learn someone else's lessons for them. And I think that applies a lot, right? I think about that, like they have to believe it. They have to get there.

• 12:13Speaker 00

  And I'll give you an example that's a little bit broader, but it's a moment that I was pretty proud of. And it's not totally related to the whining, but it is related to the earned success point that just happened. Okay. And afterwards, I told my wife, I said, gosh, if the lightning bolt hits right now, it's fine. I will be happy because, so my older boys, all my sons play soccer, okay? And my older boys, they had this soccer tournament. It's called the state cup and they won it. And they've won it, their team has won it two years in a row. And so they were pumped, right? They have this medal, their team got this big trophy. And my youngest son, he plays soccer too, you know, you know, for his own age group. And he's gone and his team hasn't won it before. Okay. So anyway, we're on the way home and the older boys have their medals. And they're just pumped. They're excited to talking about the game, whatever.

• 12:58Speaker 00

  And my youngest son says to us, he's like, hey, guys, can you sign us up for a state cup this year? His team. And we're like, of course, buddy. But his team historically hasn't been quite as successful as the older boys. So we're like, we'll definitely sign you up. You know, we're not sure exactly how it will go, but we'll sign you up. And then the older boys have some real empathy for their little brother, which was awesome. And they're like, Saven, both Nayan and Shreya, my older boys, Saven, don't worry. Even if you guys don't win, we'll get you a medal. Okay, we'll get you a medal too. You sit on the bench with us when we go to the games, we'll get you a medal too. And Saven, my eight-year-old, you know, I don't say anything. My wife doesn't say anything. He looks at them and he says, he smiles. He said, no, that's okay. I want to earn my medal.

• 13:43Speaker 00

  And that moment was so much better than us like interrupting and being like, well, it doesn't matter if you get the medal unless you win it. And all this stuff, he said it himself, something inside of him has now been internalized of the medal is valuable if I earn it. Right? The medal is not valuable if somebody gives it to me. And that is like the success case. There's a thousand failure cases, but the success case of, you know, earning it is the thing that counts. That was a pretty cool moment that I think is something we hope to get more often.

• 14:09Shane Parrish?

  That's awesome. It's so countercultural these days too, in a, in a world or era of participation medals.

• 14:16Speaker 00

  Oh, oh, it, it really does miss the point entirely of what the purpose is of a medal. Right? Because, you know, the medal isn't valuable because it's shiny, right? The medal is valuable because I read something recently, I don't remember where, but it was talking about memory dividends. And the reason that the medal is valuable is if it provides you with a memory dividend, with something you can think back on as to, oh, my gosh, this is what this represents. And if you get it for just going, then like, come on. And I, I do believe that there's value in participating in sport. There is all that, but it, it's like we've. It's like we've solved the easy part of the problem, right?

• 15:00Speaker 00

  The, the, the, the hard part is that kids wanna get trophies and they wanna earn them. And only one team can win it, right? And maybe the second place team, I guess. But we've solved that by like, okay, cool. We'll just give everyone a trophy. It's like, no, the way you solve that is by going home and having the hard conversation with your child afterwards of, if you wanna win, why do you think we didn't win? Well, we didn't win because they probably practiced more than us. We didn't win because they, uh, maybe more naturally talented than us. What are we gonna do about that? And the easy answer is, well, sure, we'll give everyone a trophy, but that doesn't solve the actual problem. And so I do think that to me is pretty endemic in general. I sound like I'm, you know, preaching, but I, I, I think that's a real thing.

• 15:40Shane Parrish?

  You and me both, man. I, I think the same thing sort of about, uh, you know, the slow elimination of gifted classes versus non-gifted classes.

• 15:50Speaker 00

  Yeah.

• 15:51Shane Parrish?

  And it's all in the name of equality.

• 15:54Speaker 00

  Yes.

• 15:55Shane Parrish?

  But it's so interesting in terms of how to think about that, which is like some kids, uh, are better at math than other kids. And you wanna challenge them or you're gonna lose them. And those are the kids that might do something amazing in math in the future. And if we lose them, then we're, we're losing all this talent too. We're doing them a disservice in a way.

• 16:13Speaker 00

  Well, I think it's also to your point, Shane. You know, even when people say equality, it really is mistreating the kid that's better at something.

• 16:21Shane Parrish?

  Totally.

• 16:21Speaker 00

  Right? Why do they not get to be challenged? If you really think about it, why do they not get to enjoy school anymore? Why do they not get to feel like they're learning something? You, you know? And I think that, um, you, you wanna give everyone a chance for sure. You know, we are products of people being given a chance. But you, you can't mistreat somebody who, uh, either has worked hard or has natural, you know, talent. I just don't think that that represents it. I think that we've talked about companies, all that. That happens in companies too. You know, um, and I just think that, yeah, I don't, I don't like that.

• 17:01Shane Parrish?

  You want.

• 17:02Speaker 00

  And it also is dishonest to the, to the person because at some point, you're gonna have to pay the piper. At some point, the world will decide whether you are good enough for the thing the world is asking you to do. Whatever it is, like no one's gonna listen to your podcast if it's not good. Right? Like, so at some point, the bar becomes the absolute bar. You can't fake it.

• 17:23Shane Parrish?

  I want to come back to the bar for a second. What seems to be happening is we just kick that can. It's like, yeah, we all know intuitively, we have to have this conversation and that there's a reckoning, a moment when reality meets the situation. But it seems like, at least in elementary school and even in high school increasingly, it's like, we're just going to kick that can a little further down. I don't want to have that conversation. The next person can have that conversation.

• 17:48Speaker 00

  Yes, yes. Well, this is, it's so fascinating. You just said that and you mentioned reality. So I have a couple of things that I say a lot at home. I say a lot at work and I say a lot, you know, in any setting where someone will listen to me. But two things, one, reality is undefeated, right? Reality is undefeated. And the second is embrace reality. The sooner you figure out what reality is and you embrace it, then you can do something about it. Right? And I have a friend who's a founder and he was, he was down like six months ago. And he asked, he said, can we have dinner together? I'm not feeling great. And we went and we had dinner and, um, you know, it's not like the dinner ended and all of a sudden he was feeling great. But then three weeks later, he sounded like a different person. So I asked him, I said, what happened?

• 18:33Speaker 00

  Why, you sound so much better. What happened? And he said, you know, instead of just thinking about the problem in the last few weeks, we've just started working on it. He's like, and we've only made like 1% progress. But he's like, it's so much better now that we're just working on it. Now we're just working on a problem. Whereas before we were just thinking about it. And I think that that comes from the embracing of, okay, this is where we are. This is what we got to go do about it. And I, uh, I think your point of effectively trying to avoid reality and kind of kick the can down the road and have somebody else have to deal with it. That's a real disservice to someone you care about or someone you love. It's the same point, reason that feedback is valuable.

• 19:14Speaker 00

  It's the, you know, I, I think it's the reason that sports teams are a good analogy when they're at the, at a very high level. Because the feedback happens every minute. If you're not good enough to be on the floor, if you're not good enough to be on the field. The ball goes by you, your team might give up a goal, you know, it is quite obvious and the feed mechanisms are quick. And so I think that one of the things that I think about is sort of the speed of reality, how quickly does reality hit you? And what is the impact of reality? And so there's that saying that every morning in Africa, I saw this on Twitter recently, but you know, every morning in Africa, Gazelle wakes up and knows that if he doesn't outrun

• 19:59Speaker 00

  the fastest lion, he's gonna die. Okay, cool, so he wakes up running. Every morning in Africa, a lion wakes up and knows if he doesn't outrun the slowest gazelle, he's gonna starve. So he wakes up running. Well, for those folks, for the gazelle and the lion in that case, reality hits, you know, very fast, every minute of every day. And the cost of not facing reality is death. Obviously, that's not quite the same for any of us sitting in our offices or whatever. But I do think, understanding that reality does hit you every moment and that not embracing it does have a cost, I think that's really important and valuable.

• 20:36Shane Parrish?

  Well, let's dive into that a little more because you work with founders who live and operate in a reality-based world. They can't create their own reality, they have to deal with reality, they're in the truth business, if you will. How do you help them see reality instead of misinformation, or erroneous information, or getting caught up in their own beliefs or their own ideas that may or may not be true?

• 21:06Speaker 00

  Yeah, well, I think the first thing is, a lot of founders, you know, they're different. Some of them are amazing at that to begin with, right? That's their wiring, that's the way they are. And so frankly, with those folks, a lot of it is just making sure that you're helping get the right signals to them, because by nature, they are such where, you know, they do that. There are some who, I think, I'm sure you've heard about the Steve Jobs reality distortion field, right? I think that's actually been pretty negative overall to the like startup ecosystem, because I think that people have heard that as Steve Jobs didn't embrace reality and Steve Jobs...

• 21:48Speaker 00

  I actually think that his was quite different. That was a representation of ambition. That was a representation of we need to be great. And I think that that was a representation of I'm not going to be constrained by what someone tells me can or can't happen. He still was embracing reality as to whether or not people love the product, right? He still was embracing reality as to whether or not it was selling and things like that. And so I think that, um, I think one aspect is sort of reminding people that the Steve Jobs example, which is incredible in so many ways. You kind of have to dig underneath that. The reality distortion field wasn't that he wasn't listening to market signals, right? It was that he was ambitious for his team of we can do better, we can do more, we can do more, right? Go ahead.

• 22:29Shane Parrish?

  When, when I think of Jobs, what I think about when that happens, this reality distortion field, which I think we've mislabeled in a way. I think that his standard was just so much higher.

• 22:42Speaker 00

  Yes, yes. The better example to me of Jobs is, have you ever heard the anecdote about him with the, with, uh, when he looked at a cabinet?

• 22:51Shane Parrish?

  No.

• 22:52Speaker 00

  It's an amazing anecdote. Okay. So there was this beautiful cabinet that he saw. Okay. And he loved it and he thought it was gorgeous. And then he looked around the back of it and in the back of it was plywood and it was ugly. And he was so offended by this notion that the front of it was beautiful and the back of it was ugly. Because someone's like, no one's ever going to see the back. And he's like, no, I see the back. The back should be beautiful too. If you want to try to make something beautiful, it should be beautiful from every angle, right? If the purpose of this is it's supposed to represent craftsmanship and beauty, don't, don't go halfway and make the back ugly.

• 23:31Speaker 00

  To me, the things that are interesting are like if you tear apart the iPhone, even the switch, even the board underneath is, you know, clean and gorgeous and thoughtful. And I think that even the words on the back of the iPhone where it says, you know, designed in California, assembled in China, like it doesn't say made in China.

• 23:52Speaker 00

  And so every choice that they made, I think, represents those are cool stories about Jobs and the standard that he had and the sort of willingness to be disliked in the name of going to get excellence. There's a story about Alexa with Bezos that's similar, where they came back and said, "Look, the latency is going to be this." And I don't know what the unit was, but Jobs or Bezos effectively said, "Well, I want it to be, you know, one-fifth of that." And they said, "That's impossible. We can't do that." He said, "Well, then we're not going to ship it."

• 24:23Speaker 00

  But that was the magic, and then they ultimately ended up doing it. So I think that consistent raising of the standard, that's the lesson from these folks. And so I think, going back to your point on reality of talking to founders, I think it's helping them see the right signals. Because sometimes, especially in the environment, and look, you know, investors, you know, all of us, we sent many of the wrong signals for a couple of years where people were rewarded. And so they could look at something of like, "What are you talking about? My business keeps on getting valued higher and higher and higher, you know? I'm doing the right stuff." But I think the duration of their perspective was not necessarily correct in that ultimately, you know, your business is going to be measured on the financial performance of it. And the financial performance

• 25:06Speaker 00

  is a representation of how much customer love there is and how much what you've actually created. But I think the point, Shane, for me on getting people to embrace reality is, okay, cool, that signal that you're looking at is supportive of the point that we're doing great. What about all these other signals? And I think that, you know, you have to earn the trust of somebody, like you said, to be able to share that perspective. But I think that idea is one that I think is really important to make sure that people have.

• 25:34Shane Parrish?

  Before you worked at Instacart, you were at KKR, right?

• 25:39Speaker 00

  That's right.

• 25:39Shane Parrish?

  I haven't heard you talk much about your experience at KKR, but you were there like a decade. I'm curious, like, what did you learn while you were there?

• 25:46Speaker 00

  You're right. No one has ever really asked me about my time at KKR. And I was there a long time. So what did I learn? One, I learned it is extremely hard to build a real business. I think that when you think about...

• 26:05Speaker 00

  The companies that KKR will try to buy or invest in. There are businesses that have generally been around a long time. And they produce a lot of profits, right? But I think that when you first get there, you think that those are just a dime a dozen and they exist all over the place. But anytime you go and study one, you realize that every business is fascinating. If you're willing to go down into the details, every single one, any business that you want to go and learn about. If you go and learn the details, you will find it fascinating. So that was one lesson, which is that every business is hard and every business is fascinating if you go deep.

• 26:42Speaker 00

  The second thing that this will relate to why I tried to join a tech company is that uh, growth is extraordinarily hard to come by once you've kind of stopped growing. It is so hard to get something to move up again. It is so hard. We have gotten numb to growth rates like 20%, 40%, 80%, 100%. I mean, this in any sort of day to day company outside of tech, these numbers are insane. And it's quite intoxicating when something is growing. It's so fun. And I think that one of the things that you look at in private equity is like, if you can get something to grow, if you can find a management team that can help you grow a business, it's amazing.

• 27:27Speaker 00

  But it's very hard to go from, you know, 2% growth or flat to 5% or 10%. And so I think uh, there's this Eric Schmidt quote of like, growth solves all problems. And it's not exactly right, but it's pretty close. Like growth is incredible.

• 27:44Speaker 00

  And then the last thing, well, not the last thing, but one other thing that I think I found valuable from KKR that I think, you know, ports over is every time you make an investment, you are kind of thinking here are the three things that need to go right in order for this thing to work. And I think that that logic or that focus and that kind of belief, I think, has applied when I worked at Instacart, it applies when I work at Sequoia. And it is, I feel like, a pretty enduring lesson of, you know, what are the things that you're actually betting on? What are the things that need to be right for this to become what you hope it becomes? And then my personality is to be maniacally focused on those one to three things.

• 28:29Shane Parrish?

  I want to come back to that a little bit, in terms of the focus. I like that in the sense because it forces you to actually make a decision, too. Not everything can be important. And I want to spend a large time talking about that. Before we do, you said something that was really interesting, which is restarting growth after you've stopped growing is really hard. And I'm wondering if we can get into some of the reasons why. I have a hypothesis that one of the reasons is actually human nature or biology kicking in, which is when the pie is growing, we live in this culture of abundance. Our mindset is surrounded by abundance. And so it triggers our biology, like our biological instincts

• 29:10Shane Parrish?

  in a way that is growth oriented. We're happy with people, we're getting along, but the minute growth stops, it triggers scarcity. And what do animals do in scarcity, right? Well, now it's about self-preservation. So we hoard, and we hoard. So the culture actually changes, too, because now it's about, oh, we're dividing the pie. I want to make sure I get my piece, and I want to make sure my piece is slightly bigger than yours. And that's all of our animal instincts. I don't think it happens consciously. I just think it's sort of like how we subtly react to these environments.

• 29:42Speaker 00

  Yeah, it's so fascinating. I think you're totally right. I'd never thought about it like that, because to, but you're right. Everyone is, the people are so much happier when it's growing, right? And you actually can solve a lot of problems by being like, folks, if this all works, we're all going to be great, right? Don't worry. There's enough to go around, right? You know, to your point, we'll grow the pie. And I think related to what you said, there's another human nature point, which is You know, when you move away from growth, the way to improve the business is to optimize it. It's to optimize it, optimize it so that you can get a little bit more profitability, a little bit more profitability. Right. And you sort of start focusing on and you bring in people that are much more oriented towards optimizing, optimizing, optimizing. And you become good at that.

• 30:26Speaker 00

  The problem is that actually has almost nothing to do with creating. It has almost nothing to do with actually going and making something attractive to more people. And so you have a different set of people in the org. And then you also have the loss aversion, another element of human nature of the only way sometimes to get it to go is you have to experiment and you'd have to risk something that you already have. And so people put in the constraint of, well, I don't want to have, I have a innovation budget. I have, I want to keep my profits at this level. And all of a sudden you have some constraint that's actually quite hard to operate around. You know, and I think the other thing is, look, at the most fundamental level, it's really hard to get people to use something.

• 31:09Speaker 00

  If you really think about what growth means, it means you're going to get somebody new. Right. To use the product that doesn't use it now. Or you're going to get somebody who uses it now to change their behavior to use it a lot more. It is really hard to get somebody to change their behavior. This is this whole idea of it can't be 20% better, it can't be 40% better. It needs to be 10x better. It has to fundamentally change, you know, your experience. And it's very hard to create things that are way better. Cause we all talk to ourselves, well, this is a little better here, it's a little better here, but nobody cares. One of the big things that's so fascinating is, again, Bezos says this in one of his letters, but consumers are divinely discontent. You can give them something amazing and then it's just normal.

• 31:54Speaker 00

  People really do just like find things to be normal. So it's hard to innovate. I think that's the other thing.

• 31:59Shane Parrish?

  Well, it becomes the new baseline, right? So the new baseline is like, why would I write an essay? Chat GPT can do it for me.

• 32:06Speaker 00

  Yes. One of the best pieces of advice I got in writing was from Mike Moritz, who's obviously this beautiful writer. But he said, after you read, after you think you have aversion, read it out loud. Read it out loud. See how it sounds. And he's like, most of the time you'll be horrified. And until, read it out loud and edit and edit and edit until you like how it sounds. But it really does demonstrate, you know, the quality of the thinking when you can read it out loud and feel good about it. And I think on your point, if it could be written by chat G P T, then maybe it's not that good. Maybe you should try to write something better or more insightful. And I think that the ones that I am proud of, I think probably would be harder to write by that right now. And maybe the ones that could have been written by that aren't as insightful as I thought.

• 32:52Shane Parrish?

  I'm curious what other writing advice you've been given that you've found useful.

• 32:56Speaker 00

  Yeah, so there's been a few because I was almost scared to write for a while because I assumed that it was hard for me and easy for everyone else. And therefore I just wasn't very good at it. And, you know, the logic, even as I say it out loud, is pretty dumb. But a lot of what I've heard is just sort of embrace the fact that it's difficult. It's difficult for everyone, right? Even the best writers don't, they don't, it doesn't just come out, right? They just do so many drafts, they do so many versions and they just kind of, you know, hammer it every day. I'm sure you've heard the stonecutter's credo, right? Of, you know, pounding the rock.

• 33:38Speaker 00

  A lot of what I think great writers do is they just sit down and they write every day.

• 33:45Speaker 00

  So that was one piece of advice, which was if you want to get good at it, just keep going over and over and over again.

• 33:53Speaker 00

  I think another thing that I have found that's been good advice for me is

• 34:04Speaker 00

  choose the topics that you actually care about. Don't try to write about what you think someone else will think is interesting. Write about something that you actually care about. And it'll either be interesting or it won't, but at least you'll find that you want to write about it, right? Find the thing that you're compelled to write about. And so I think that was good advice. And then the last one that actually is one that I take in very seriously is if something comes to mind you want to write, stop what you're doing and go write. Don't, you know, get out of the meeting, go and sit down, write it down, write it down, write it down. One of my, one of the things that I wrote that I'm most proud of is actually it didn't get a lot of attention or anything like that. But, and it shouldn't have because it's a very like niche thing. But I wrote it on my notes section on my phone in the airport.

• 34:49Speaker 00

  And but I felt something and so I just started, I wrote the whole thing on my notes section and that was cool like otherwise I would have been like, oh, I just like put the thought in my head and then I would have never written it otherwise. But I was taking a red eye and I was, you know, I was a connecting red eye and it was in between the connection and I wrote it there. And I'm really happy it exists because I wrote it when I felt it and I have it for me. And it was something that I think was good advice on the, if you feel it, just stop what you're doing and go right.

• 35:19Shane Parrish?

  I like that a lot. I sometimes do that on my watch. I'll actually just pull out, hit record and then talk because I find that a little easier and I can be anywhere. I mean, I've done this in the sauna, I've done it sort of like in the lake. It's like I got an idea, I can't get to a pen and paper, I'm just gonna like hit record and, and sort of get it out and then I can come back to it later. Often I don't come back to it, but sometimes I do. The other thing you said that I thought was really important there was doing things when you don't feel like doing it. I think that's almost the key to success in any domain is like doing things that are important, even if you don't feel like doing it in the moment because you know long-term it's important.

• 36:00Shane Parrish?

  How do you motivate yourself or how do you create a ritual around that to, in order to be able to do it when your willpower is lacking?

• 36:09Speaker 00

  I would segment it into different components because I, I do think there are different answers for me on different things. So let's take like physical exercise. You know, some people love exercising, they love it, they, you know, it's their, they say all these wonderfully poetic words about it. I don't particularly enjoy it at all, right? I like the result of it. But a lot of the willpower comes from there of, I really do wanna like live a long time so I can see my kids when they're older and spend time with my grandkids and all that kind of stuff. And I wanna be able to do things with them now and I, I'm afraid of, you know, not being able to do active things with the kids.

• 36:54Speaker 00

  And so a lot of times I just sort of. A lot of the willpower there comes from a want to do stuff with my kids and my family for a really long time. I love playing sports with them. I love being active with them. And frankly, it's kind of like meeting them where they are, which I know is like a little bit of a statement that doesn't really sound like it means anything, but I actually think it's a real thing. Sort of like what they want to do, I kind of want to go do with them, you know? And a lot of times what they want to do is run around and I like being able to do that. And so the willpower there comes from sort of, man, you don't want to be one of those parents that can't do stuff with their kids, right? At any age. And I think a fear of like, I, I do, I want to do everything I can to live a long time.

• 37:38Speaker 00

  And I'm sure that if I was more zen, I could say like, oh, you know, I'm be fine and whenever it goes, it goes. But I'm not like that. I really do want to live a long time. I like life.

• 37:48Shane Parrish?

  Oh, I was gonna say, I'm the same way. Like I, I have a different approach than you, but I have the same goal, right? Like I want to live as long as I can, as healthy as I can, for as long as I can. Uh, it's not sort of duration, but I want to actually like live and, and, and sort of be able to do things with my kids and all of that. When it comes to willpower, it's like, I know I need to go to the gym. I hate the gym. I'm not one of those people who's like, oh, this is fun. Can't wait to go. And so for me, I've determined that every day is easier than some days. Because if I go to the gym some days, it ends up being a negotiation with myself.

• 38:32Speaker 00

  Yeah.

• 38:32Shane Parrish?

  And that negotiation is, I don't have to go today. I'm gonna go tomorrow. But if I go every day, there is no negotiation about whether I'm going to do it. So whether I'm gonna do it is predetermined. So I go every day. The negotiation becomes, when do I fit this in my schedule? When does this make the most sense into my calendar? And it changes the way that you talk to yourself about it. And I found it super powerful because the people that I know have started working out and then stop, it's always a negotiation with them. I don't feel like getting out of bed today. I don't feel like going to the gym today. I don't feel like, and it's like, who cares how you feel, honestly? Like, if you've decided that the gym is important to you,

• 39:17Shane Parrish?

  and that's something that you need to do, how you feel about it doesn't really matter. Same as like, I don't feel like going to work today. It's like, it doesn't really matter. You still gotta show up, do your job.

• 39:26Speaker 00

  Well, so, okay, I like your answer so much better than mine. And so I'll, I'm gonna, I'm gonna do an addendum because I actually think more of the physical part to me is actually food than working out in terms of the discipline. And so I think to your point, though, in probably my favorite book, How You Measure Your Life, Clay Christensen has this quote of, you know, it's easier to follow your principles 100% of the time rather than 98% of the time because you don't know what 98% of the time to follow them, right? It can always be a negotiation as to what's the two. And so I think your point on the everydairness is a big deal. So, yeah, my physical fitness answer on exercise is pretty mediocre. I think the food one, I have a more of a framework, which is, I work out with this trainer twice a week and he told me one time, he said, look, there's 21 meals in a week, okay?

• 40:09Speaker 00

  He goes, if you want to lose weight, 19 or more of them have got to be good meals, okay? If you want to maintain your weight, 15 to 19 of them are gonna be good meals. And if you're less than 15, you're probably gonna gain weight. And it was really simple. And so for me, that is actually the thing that I think about for food all the time. I do a count. I'm like, okay, I got 21 of these. And what I try to do is remove any sort of decision on 10 of them. Monday through Friday, breakfast and lunch, just do the same thing every day, right? And then ideally, I do it on the weekdays too. I can avoid, ideally, I avoid a work dinner, right? Or I avoid eating at a restaurant or something like that. Because what I'm trying to do is get as many in the house as possible before the weekend, right?

• 40:52Speaker 00

  Because the baseline would ideally be that my Friday night and Saturday night are the ones that I can, even if we don't even go out, which I can do with the kids, whatever, those are the ones where they're not good meals. But I'd say framework wise, on the, I try to almost remove the willpower by not having the ability to make a decision on as many of them as possible. So that is one thing I try to think about on the physical side. And it's similar to you of like, Everything is a discussion. You just try to have fewer negotiations almost on that.

• 41:22Speaker 00

  On the, on the work front of sort of like doing the right stuff.

• 41:28Speaker 00

  This is one where I, I have a quote on my desk and it's from Tom Izzo, the coach of Michigan State. And I'm a Duke fan, but I thought this is a pretty good quote. And it says on there, it's not because you've got to, it's because you get to. And it's at the top, they have that quote at the beginning of the Michigan State locker room or the weight room. And I think it's this reminder of dude, you chose to do this job. Yeah, sure. It's a hard job, whatever, but you chose to do this. You, every day you don't have to do it. And so if you're gonna do it, remember like you, you made the decision to go and spend your time away from your family doing this. And I think again, like I come back to the family point. It's like, make it worth it.

• 42:09Speaker 00

  If you're going to be gone from the kids, from your wife, from people you care about, make this worth it. Otherwise, what are you doing? And I think reminding yourself that, you know, you wanted this and you have affirmatively chosen this. That for me is an important part of the, the kind of self-talk to have the willpower to do the thing that you need to do is don't waste this important time that you're using away from people that you care about. Cause I do think like time is precious and you know, you gotta be affirmative in how you spend it. And so it's kind of like, uh, every day, make a decision that you've made it worth it.

• 42:45Shane Parrish?

  I love that. I love the meal thing too. I've never heard it put that way before. And I think that's simple and easy to understand and very actionable.

• 42:52Speaker 00

  It also prevents you from having more than the three meals, right? Because you're kind of like, oh man, 21 is the number and

• 42:59Shane Parrish?

  It's only Tuesday. I've already hit that.

• 43:01Speaker 00

  Yes. Yeah, exactly. Like, oh, I had, you know, nachos at 10:30 last night. Darn.

• 43:08Speaker 03

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• 43:41Speaker 02

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• 44:07Shane Parrish?

  I want to go back to your time at Instacart a little. I'm wondering, you know, what seemed missing or broken when you were there doing that? And you still don't think has been really solved or fixed?

• 44:20Speaker 00

  Of course, you know this. I love Instacart. I, the reason I went there was we used it a lot. And when I was meeting with the company, I asked my wife, what do you think of Instacart? And she said, oh, my God, I love Instacart. And I said, OK. And she said, if you wanted to move, the first thing I would do is see if Instacart delivered to the new house. And I just remember thinking like, I mean, what an anecdote, right? Someone, the person you respect most in the world telling you that they wouldn't move unless this product delivered there. So the love for it existed seven, eight years ago. It exists now. I love it. In terms of something that was missing when I was there and is still missing,

• 45:00Speaker 00

  it's really hard to get everything you ordered every time. It's just, it is, it is a hard problem. And I'll, I'll do the math, right? A typical order has 15 to 20 items in it. OK, and we have a very high chance of finding that specific item. But grocery stores don't always know exactly what's in it, right? They don't always have a perfect thing. And people's algorithms for what they want to replace it with are not always the same. So I have a friend, one of my closest friends. He, you know, likes to eat grilled cheese for dinner. But if the grocery store doesn't have something that goes into a grilled cheese, that would be kind of strange if they didn't have it. But you get what I'm saying. If they don't have one of the ingredients for grilled cheese,

• 45:43Speaker 00

  his algorithm for what he wants, if he doesn't eat grilled cheese, is a quesadilla. Well, that's not like, oh, the cheddar is not there. I want the medium cheddar. It's like, oh, if they don't have sharp cheddar, I want an entirely different dish. And it's very hard to predict exactly what somebody wants if you don't have what the thing that they ordered. And grocery stores don't always know what's in it. And so Instacart's gotten so much better at this. But it still is not 100% of the time, everything you ordered or something that you would want perfectly as the replacement. And I think that it's one of those like, you gotta enjoy climbing the mountain because, you know, the company keeps on getting better at it. But like, it's not there, it's not perfect, and it's still not perfect.

• 46:24Shane Parrish?

  I had never thought about it that way. Like if I order Windex and you switch it for a no name brand, I mean, that's simple, pretty obvious.

• 46:31Speaker 00

  Yes.

• 46:32Shane Parrish?

  99.99% of the time that works. I had never thought about the fact that if I'm trying to make real cheese and you run out of cheese. Well, then in my head, I don't go for a substitute from cheddar to mozzarella. I actually move to an entirely different meal. And so you're replacing the cheese doesn't really fulfill my need, but it's an unstated or

• 46:55Speaker 00

  Yes.

• 46:56Shane Parrish?

  almost impossible to discover invisible need.

• 47:00Speaker 00

  Yeah. And, and, and, you know, you can imagine, oh, well, you should ask the person, what exactly, what do you want if this doesn't happen, if this doesn't happen? And I mean,

• 47:08Shane Parrish?

  But that also requires like real time interactions because you don't want somebody standing around a store or

• 47:14Speaker 00

  Yes.

• 47:14Shane Parrish?

  this endless loop or like diagram of like, okay, if this, do this. And on a 20, 20 cart order, that could end up with like 15,000 different like permutations of

• 47:27Speaker 00

  Of course. And this is where it's so funny because, you know, what I would tell people when they would say, well, isn't the space competitive? I was like, yeah, of course it is. I was like, but guys, Instacart started in 2012. So at this point, you know, the company is, you know, 10 and a half years old. I was like, we've made 10 and a half years of mistakes. This is hard. And I think that that is actually a huge advantage. And you think about what we were talking about earlier on businesses, businesses being fascinating, businesses being interesting, businesses being complicated. Instacart is a hard business, but it's a good business now that like, you know, the company has done really well and, you know, learned a lot of lessons. But that, that's one thing that I think. Was missing, it's like less missing now, but it's definitely still not perfect.

• 48:09Shane Parrish?

  One of your beliefs is quality over quantity. And I'm wondering, are there fun ways that that applies that may be not, non-intuitive to the rest of us? I think it's easy to be like, oh, I'm gonna buy higher quality food. I'm gonna consume less of it. But what are the non-intuitive ways that that idea applies to your life?

• 48:28Speaker 00

  Well, I'll tell you them, and then I'll tell you the one place where I think that, that what I just said does not apply clearly, where quantity is more important than perceived quality. So I'll give you one where I think I'd break my own rule. I think one non-intuitive way is,

• 48:46Speaker 00

  Shane, if I think about the jobs you've had, okay? And you look at the percentage of people that delivered 90% of the value in the places you've worked. Right? What percentage would you put on it? What percentage of the people do you think delivered 80 or 90% of the value in the places you've worked?

• 49:06Shane Parrish?

  Five?

• 49:08Speaker 00

  Yeah. So that's a pretty extreme thing. I would say the same thing, five to 10%. Everyone talks about 80, 20 and all this stuff. What company acts like 5% of the people deliver 90% of the value? Very few, very few. And so to me, one non-intuitive thing is like, think about, you know, in the company you work at, what percentage of the people deliver 90% of the value? And think about whether you're actually acting like those people are treated that way. I don't mean in terms of money. I just mean in terms of respect, authority, love, you know, responsibility. Frankly, like, are you acting like if they left, it would be a big problem? All those kinds of things. And I think that 80, 20 is conventional, 590, not conventional.

• 49:52Speaker 00

  But my experience is closer to yours. And that is one aspect where, if you think about what that means time-wise. It means if you can get one of those five, right? You should spend a crazy amount of time going to find them, right? You should spend a crazy amount of time getting to know people who could possibly be one of those five. And actually, the entire point of being a leader might be to go find two or three trajectory changing people for the company, rather than all of the other things that make you feel like you're making more linear forward progress. So I think five ninety would be something that I would think about, right? I think about that a lot. And if you have one of those people, that's one of the five. Are you behaving?

• 50:36Speaker 00

  Are you aware of everything that could make them go? And are you in sync with them? Because I think that people spend a lot of time trying to appease the ninety-five percent that are delivering the ten, delivering ten percent of the value. Think about comp systems. Think about the number of times that you'll be in a company and somebody great will be like on the fence of staying. And you'll be like, well, could we do this on compensation? Could we do this on title? And they'll be like, well, the bands don't allow that. Like, you created the bands. What are we talking about? Well, the purpose of the bands is so that we win. That is a tool that we're using. Now the band is preventing us from winning. What are we talking about, right? People, well, it's fairness. I'm like, it's not fair to the person who's excellent.

• 51:19Speaker 00

  So that'd be one where I think the quality over quantity, I think people really don't, you know, do it in the, the way that they should. I think the second thing that I, I'd put on that is, I don't know, what percentage of your time do you spend with the people that matter most to you? A lot of people, not very much. Like, one of the things that I wonder about, and I wonder about this in my own life, like, you know, I think my wife and I are very good on spending time together, spending time with the kids, spending time with our very close friends who are, who live close to us. I think we're pretty good on that. We don't just kind of peanut butter it. And I feel like, you know, we have been thoughtful and affirmative in those decisions. But like, my parents live in Chicago.

• 52:03Speaker 00

  My parents live in, you know, my brother lives in North Carolina. My mother-in-law, who we're very close with, my wife's mom, lives in North Carolina. I don't know. They come, they spend, they come every six or eight weeks. They spend a week or two with us. So we're like pretty good. But we made a pretty weird decision to go and like live pretty far away from them. One of the things I wonder about is whether this. I think kind of American mentality of like, go where your career takes you, go where the best professional opportunity is rather than living close to your family. I wonder if that's an experiment that's not going to turn out to be right. Because um, so I think we're doing that in some ways and we're doing it pretty well. But not as well as we could relative to our grandparents, relative to the grandparents and you know, our families. Uh, so that's some another thing.

• 52:49Speaker 00

  And then I'll tell you the place where I think that the quality over quantity theory actually leads to some pretty bad behavior. Is that okay if I go there?

• 52:55Shane Parrish?

  Yeah, please.

• 52:57Speaker 00

  So I think with your kids, when they're young, I think the quality over quantity is a very pernicious. Thought because it allows you to not spend that much time with them and be like, oh, it's all good. I'll, we'll, I'll just be there for like a. Kick ass birthday party, right? I'll be there for, I'll take them to Disneyland and I'll create this incredible memory that they'll love. And it allows you to be gone more than I think you should. And it gives you an excuse. And it gives you a reason that you can do that. And I think the truth of the matter is for young kids, you have no idea when the good moments are coming. You have no idea when the quality or moments are coming. It might not be at the birthday party. It might not be when you go to Disneyland. It actually might be when you're just like sitting on the couch.

• 53:41Speaker 00

  And they say something that makes you like, oh, my gosh, right? There was somebody, we spend a lot of time on like youth sports. We don't care, we don't care if our kids like do anything with sports. We're not, we don't care about it at all. But we end up driving all over, you know, Northern California uh, on the weekends. And I had a friend who was like, what are you doing? Do you think your kids are going to do anything with sports? I was like, probably not. He said, why do you spend so much time? Why do you waste so much time on that? And he's smart. And I thought about it and I'm like, well, the truth of the matter is, I love being at my kid's sports game. They're having fun. I love watching them. I actually really enjoy driving them to those events. Because kids kind of forget when they're in the car. They have nowhere else to go.

• 54:26Speaker 00

  And they're super chatty, right? And getting a lot of those in-between moments with them. What would I be doing if I wasn't doing that? Would I like be looking at my phone, like on my, what would I be doing? It's actually the thing I do want to do. And I love that the quantity is there, if I really think about it. And so anyway, I think quantity is kind of the main thing when it comes to family time, particularly with young kids. And I actually think that a lot of people tell themselves a story on this one that I think is not going to be great long term.

• 54:54Shane Parrish?

  Have you ever invested with a founder, and no names here if you have, that was focused on their business to the detriment of their family in an extreme way? Like that neglected their kids, neglected their wife, that was successful?

• 55:16Speaker 00

  Yeah. I don't know if it's direct me investing, or, but I've certainly seen it, for sure. And

• 55:25Shane Parrish?

  How does that play out later?

• 55:27Speaker 00

  Yeah. Well, I think the first thing is it doesn't always like end in a obvious schism, or an obvious break, like divorce or something like that. I think sometimes it ends up as just, the relationships aren't the way that they would want them to be. I think the way it plays out Shane, is, a lot of times it's sort of like the moment by moment corrosive behavior of just sort of, that's the thing that you want to talk about. That's the thing that has your attention. So like when, when Afni and I have fought about work taking up too much mind share, it's not that all of a sudden I'm a jerk. It's that I'm not present.

• 56:11Speaker 00

  It's that the only thing that, it's that when she's talking about something, the thing that's going through my head is the thing that I'm thinking about. And it's something related to work. Or the stuff that I am talking about with her, or with our friends, is all stuff all about me. Or it's that like, when I go to the, I'll still go to the kids' stuff, but I'm not paying attention. I'm looking at my phone.

• 56:31Shane Parrish?

  You're not present.

• 56:31Speaker 00

  And so I think a lot of the things that, the way it plays out is, it's not sort of like the lightning bolt. Moments, it's just sort of a general drifting because the person finds you to be kind of selfish. You know, they don't feel like they're number one.

• 56:47Speaker 00

  And so I think that's the constant battle, at least as I've seen in the ones that are successful, is people kind of. It's hard, you know, funny enough, when I was at Instagram, one of the values that we had was this is your baby. Okay, and you know, the reason that came out was that people would a lot of times tell our founders. Like, that's like a statement of like, yeah, of course you care this much. This is your baby. And it was kind of a controversial value because of some of the people were like, wait a second, like, I don't. I don't like those words. And the point of it was sort of treat it like it, you care about it. Oh, treat it like you're an owner. And it was like a lot more fun of a way to say it, or a more interesting way to say it than like, you know, act like an owner. But anyway, I think that if you take that logic, though, of sometimes the company for somebody particularly who created it.

• 57:31Speaker 00

  You know, it feels like it is a family member almost. It feels like something that they hold dearly on to. And their identity is tied up and all that is not crazy to think of to like, why it could take up a lot of your mind share. And it's hard to compartmentalize. So I think that happens a lot. I've definitely seen that up close. And I think the way it plays out, Shane, is that later. They say, well. Gosh, like, I wish I would have done something different before. And one of the things I think that's true is you can't go back and change it, but you can change it that day. And I do think that people react. People are pretty good at noticing if you're doing something every day. If you've changed something and you've really committed and you're doing it every day. Right?

• 58:15Speaker 00

  You talk about this all the time in your, in the various writing that you do, which is just the value of consistency. So maybe that's the point. I think anything you're doing consistently shows up to people. It might take a long time, but it shows up and that's in both directions.

• 58:29Shane Parrish?

  On the other hand, I hold this thought, which doesn't conflict with that, but sort of wrestles with it in an interesting way. Which is I. I don't believe you can be the best in the world at anything. And be a well-balanced person.

• 58:47Speaker 00

  Okay, let me let me fight with you for a second on it.

• 58:49Shane Parrish?

  Well, you know, the example that comes to mind is like Warren Buffett, right? Best investor we've ever seen historically, you know, arguably wasn't a role model, family person. It's easy to look back and be like, well, he should have been, you know, he might have those regrets, but he might not be Warren Buffett if he had been a better family person.

• 59:09Speaker 00

  Yeah, so maybe the reason I said I would fight with you on it is actually kind of a poor argument, because the truth of the matter is, the vast majority of people that I think about as best in the world, I would agree with you on, right? Most of the examples that I think of, I do think they tend to not be that well adjusted. The person that came to mind, who I obviously have no idea about, but from a distance, is Steph Curry, where it does seem like he has a real, you know, family life, and he is, you know, the best in the world at, you know, something. Now, I think it might be a situation where the exception proves the rule, or the truth of the matter is like, you know, I obviously don't know Steph Curry, and so maybe, maybe it's not.

• 59:52Shane Parrish?

  I thought that about Tom Brady until this year, too.

• 59:55Speaker 00

  Yeah, exactly. Yeah, no, that's the problem, is that like, you know, you don't really know anything about these people. But I think, you know, maybe Shane, here's what I'll tell you, and this is something that I, it feels weird to say out loud, right? But I think it is true. If what it takes to be the best in the world at the thing that I'm doing is to lose some of those aspects that we're talking about, then I don't want it. You know, I hope, I hope I can be. I want, I am ambitious, I really want to go and try to do that. But, you know, it's not number one for me. Number one is the family, and it is sort of what Avni and the kids are going to say

• 1:00:40Speaker 00

  about the way I was and am with them. And so. And maybe I should say I'm kind of fearful that what you just said is true. But I'm not fearful enough to change it, you know?

• 1:00:53Shane Parrish?

  I totally agree with you. And then I also catch myself going, you know, the maybe the worst parts of conversations with myself.

• 1:01:02Speaker 00

  Yeah.

• 1:01:02Shane Parrish?

  Is, uh, that's an excuse.

• 1:01:05Speaker 00

  Yeah.

• 1:01:06Shane Parrish?

  Right? You're scared. You're you're getting in your own way. You could do so much more and you could. You know, this is the weird thing about about being an entrepreneur is like every minute you're not investing, you could be.

• 1:01:18Speaker 00

  Yes.

• 1:01:19Shane Parrish?

  Every minute you're not working, you could be forwarding the business. You could be doing something more. You could be improving your position for the future.

• 1:01:27Speaker 00

  Oh, it's infinite.

• 1:01:28Shane Parrish?

  You have to wrestle with this when you have kids and it's sort of like, well, what are these trade offs and what are these lines? And where do I stand with this? And I.

• 1:01:36Speaker 00

  Yeah.

• 1:01:36Shane Parrish?

  I came out with the, you know what? Uh, my kids are first and foremost always. And if I want to do more when. It's less impactful for them. And I define that by them not living with me.

• 1:01:51Speaker 00

  Yeah, I like that.

• 1:01:53Shane Parrish?

  I will, uh, I will work harder. And if I still have those ambitions and goals, I will commit to myself that I'll go all in. On whatever it is I want to do. And I define it as that because I saw a lot of parents of teenagers. Define it as them being independent. So they hit grade seven. Eight, nine, they can come home, they can make dinner by themselves. And because they can do that, you tend to, um. Take liberties that you might not actually know you're taking in the sense of, I work with a lot of people who put their careers first.

• 1:02:29Speaker 00

  Yep.

• 1:02:30Shane Parrish?

  Uh, but then they didn't know anything about their kids. They would come to me and be like, what should I get my 16 year old for Christmas? And I'm like, well, tell me about your 16 year old. And you get these like. You know, high level sketches of this kid and you're like, well, this is because you work 14 hours a day, six days a week. I can understand you might not know a lot about your, I don't want to be in that position. And so I, I create these rules for myself to keep me the best version of myself, if you will, right? So I create rules that the best version of myself wants, and then I just follow the rules. One of those rules is I'm home every day when the kids get home.

• 1:03:04Speaker 00

  Yeah, that's a good one.

• 1:03:05Shane Parrish?

  And that keeps me, they don't even talk to me anymore. They're in seven a day. They like chuck their book bags down, they go for a shower, they start their homework, they're grumpy. But I'm there.

• 1:03:14Speaker 00

  Yes, but this is where, so, so I really like that because I think to your point on sort of the, the when they live with you versus when they don't. It's again, it's very hard to predict when they're going to want to talk to you.

• 1:03:29Shane Parrish?

  Totally.

• 1:03:29Speaker 00

  Right? It, it really is very hard to know when that's going to happen, you know? And I think just sort of like being there provides a huge benefit because when they are wanting to do it, okay, you're ready to, for that serendipity, you're ready for that moment because you're there. Right? And the other thing is, like you said, in knowing them by seeing them, you actually know what the heck to say and you've earned the trust with them to kind of, you know, provide the thoughtful feedback, like there, that is a real thing. And I am just like you where I count the number of days that I have dinners. I count the number of days I'm on the road. I go to pretty serious lengths to avoid unnecessary travel.

• 1:04:14Speaker 00

  And one thing that I do firmly believe is I think focus is such a helpful aspect of trying to thread the needle because I just, I hate when I am wasting time when I'm away from them. I hate it because I'm like, no, I'm not even furthering the thing that I'm trying to be good at. This is just dumb. Why am I doing this? And so I think that like that, uh, my, my zealotry around focus is something that I think makes me feel better of like, no, I'm, I'm trying to move the ball forward.

• 1:04:47Shane Parrish?

  Well, that's your most, that's your best time, your most expensive time. You're giving up the one thing that matters to you most. So it has to have arguably the biggest payoff, if you want to think of it that way. We've talked about this on the phone a little bit and now's probably a good time to talk about it, but. It's about that concept of taking simple ideas, which we've been talking about throughout this whole episode so far, and taking them seriously. And one of the ones that you have that I admire the most, I think, about your relentless pursuit of it, is to keep the main thing, the main thing. And I'm wondering if you could explain why that idea is so important to you and how it applies in various aspects of your life and when it breaks.

• 1:05:31Speaker 00

  So obviously, this is a quote that came from, I think, Jim Barksdale. But, you know, I remember the first time I saw it and I remember just the wording and why it sat with me, but it almost sounds silly when you first hear it. The main thing is to keep the main thing, the main thing. And just, you know, anytime you see a quote with the same words three times in a row, it's really remarkable. But when I've thought about it, and it really came to life when I was at Instacart, right? It came to life for me when I was at Instacart because there are so many people pulling you in different directions about the thing that they want to talk about. And so specifically at Instacart, you know, when I got there, we were losing a lot of money on every delivery.

• 1:06:14Speaker 00

  I was very concerned that we were going to go out of business. And there was a genuine fear of our business is not going to exist. And so truly an existential concern that I thought was well-placed and fully informed by the data, right? We had less than a year of cash, it was getting worse every day, we were losing money on every order, so its volume wouldn't help us. There was an existential and, you know, imminent threat. And the number of conversations that people would have because they didn't know, right, about things that had nothing to do with that was remarkable. And I realized I could spend my whole, I could spend six months, I could spend 11 months, I could spend all of our cash months left, doing things that didn't matter to the one

• 1:06:59Speaker 00

  thing that actually was going to determine if we had a business. And that moment was like, wow, this this quote is exactly right. You have to keep focus on the thing that matters. And actually, that is the job of the leader is making sure that the organization is focused on the thing that matters. And sprawl and just spending time and little compromises on that is a disaster. And it actually, it is a, it destroys the obligation you have as the leader. So I'd say like the, the play, it became real to me when I was, you know, one of the few people responsible for the outcome of a company.

• 1:07:37Speaker 00

  And then I started seeing it that it applied everywhere. It applied everywhere. Okay, well, it applies personally. Well, your relationship with your wife and your children or the relationship with your spouse and your children. That seems like the main thing. Cool. How do you make sure that you actually are investing in that above everything else? Right? How do you make sure that the people that you're spending time with are the ones that you actually want to spend time with? And it just, I saw it everywhere. And so the reason I say, Shane, it became important to me was because I felt like it was a dramatic. It was a huge unlock for like how I wanted to live my life personally and professionally. And then it also fit with this book I referenced earlier of the Clay Christensen book, How Will You Measure Your Life?

• 1:08:19Speaker 00

  And I think so much of that was sort of being able to answer that question and making sure your decisions every day. You know, fit with that, with that answer of how you actually go about measuring your life. In terms of your question of when it breaks.

• 1:08:36Speaker 00

  It, it's at risk of breaking all the time for me. Right? Because, so when I was at Instacart, it would break when people were unhappy that our goals were too commercial. Right? All we talk about is the GMV of the business. All we talk about is the metrics. What about this other thing? Right? And somebody would say, what are we doing for climate? Climate is a big deal. What are we doing for climate? And you, you want to tell people like it will help with recruiting some great engineers if we are really forward thinking on climate. Right? And so you can talk yourself into, well, it will help us if we have the best people in the world.

• 1:09:19Speaker 00

  And the best people in the world sometimes care about these things. And gosh, like, maybe we should have a climate program. But we shouldn't have. That was not the right answer for the company at that time. And I think that, so it's at risk of breaking because it's also easy to say, yes, people feel good. You feel like you're listening. A lot of times it can feel like you're being obstinate when you're not, when you, you know, it just feels easy to make that little compromise. And then the same thing, it's at risk of breaking all the time. You know, I'll get invited to an interesting dinner. I'll get invited to an interesting thing that, you know, is away from home. And it's just like, oh, just one night, you know, that's okay. You know, there's

• 1:10:00Speaker 00

  364 other nights. But so I'd say I find it to be a constant battle, but it is something I take pride in and that I think that I am, I think it's like in my soul. It's something I really believe.

• 1:10:16Shane Parrish?

  I like the climate example because it's sort of an example that we, we see a lot today, right? We see it in politics. We see it everywhere where somebody throws something on the table. It's not the most important thing, but it's also really hard to argue with.

• 1:10:34Speaker 00

  Yeah.

• 1:10:35Shane Parrish?

  Because you feel, or it's framed like, oh, you don't think environment's important?

• 1:10:41Speaker 00

  Yeah, exactly. Oh, you don't care about social responsibility? And it's like, no, no, of course, of course I care about that. And, and I actually, I think the climate is a huge problem. I don't think that we are the people who are best suited to solve it with this company. And I think for this company, the best thing we can do is be a great company, right? And I think I also, I think I'm also more nervous about companies' ability to maintain their ability to be great. And I think people misattribute things a lot. Like, you know, a lot of people will be like, well, we should use the, the comp system or the leveling system that Google uses. Look at how big of a company Google is. We should borrow a lot of Google's processes.

• 1:11:23Speaker 00

  And it's just, to me, it's crazy because I understand the logic. Google is a giant company. It is a very successful company. It has a lot of processes. It has a lot of leveling and compensation bands and whatever. I don't think that's the reason Google's successful. I think the reason Google's successful is because they have a product that you have to use. Most of the time you use the internet and they effectively get to charge you a toll every time you use it. And I think all that other stuff is like bolted on around it. But people, I think there's a lot of correlation versus causation that people use to suggest things. And I think frankly, it's hard to disagree with people a lot, you know?

• 1:11:59Shane Parrish?

  Yeah, you don't want to be disagreeable. We, we used to sort of use it as a filter in operations because if people couldn't consistently identify the most important thing.

• 1:12:10Speaker 00

  Yes.

• 1:12:11Shane Parrish?

  Then it was sort of a sign that they shouldn't be doing what they're doing. And they should maybe find another, another job within the organization.

• 1:12:20Speaker 00

  Oh, no, I was gonna say, one of the things that we do at Sequoia now is every Tuesday, every single person writes down their most important thing for the week. And we, and we share it. We like literally have it on a Google sheet. Every person, what is the most important thing you are doing this week? And you can pick whatever unit you want or unit of time. But I really like that discipline of like, please write it down and don't write down two of them. The purpose is to have one, you know? But I like that, but sorry, I interrupted you.

• 1:12:48Shane Parrish?

  No, I was, I was thinking like, have, do you know anybody that uses this as an assessment tool to gauge success? I'm formulating a hypothesis as we talk that if you were to give somebody a complicated scenario, and this was their only interview question. And the only question was identify the most important thing in this scenario.

• 1:13:09Shane Parrish?

  That that would correlate to outstanding job performance.

• 1:13:15Speaker 00

  I like that. Yeah, I, you know, literally, uh, somebody, Alfred Lynn, the other day, asked me, you know, who, what is your favorite interview question? And I sent him to him. Now, honestly, I felt like it wasn't that good of an interview question after I sent it to him. And I would so much rather have asked what you just asked. And I'm gonna take that because that is what I care about. I care about someone's ability to identify the thing and then to execute against the thing, right? Um, and I, I, I like the hypothesis that you just, you know, formulated.

• 1:13:48Shane Parrish?

  Well, if anybody does this, I wanna email me. I wanna see the results.

• 1:13:53Speaker 00

  Yeah, of course, I'm gonna do it. I'm, I'm gonna take it. I'm gonna experiment with it now for the next few months. So if I ever interview somebody soon, that's the question they're gonna get. I'm gonna come up with a scenario and be like, what's the most important thing?

• 1:14:03Shane Parrish?

  And, and you can make it complicated where you, you can email your partners and not everybody would agree, but they sort of correlate on, you know, 80% of high performers would pick this as the most important thing. And I bet you, uh, yeah, I'm interested to see the results. I bet you that would be a really good proxy for on-the-job actual performance.

• 1:14:26Speaker 00

  Well, so there's this person who I worked with at Instacart, um, who told me she was, you know, you mentioned ops, she was, um, uh, an ops leader in San Francisco. And the scenario she would give is, uh, and I thought it was an amazing question, effectively this, but she would say, look, she was interviewing somebody, hey, you're, um, one of the managers in San Francisco and one of the people at the store in, at the Safeway in Portero Hill calls you and says, hey, look, the refrigerator where we store the groceries, because, you know, we would have a shopper pick it and then put it in a refrigerator and then a delivery driver come get it from the refrigerator, you know, and then take it to someone's house. The refrigerator's not working, right? Um, what, what do we do?

• 1:15:10Speaker 00

  And she said, you get all these answers of people. Sometimes people have, you know, backgrounds that are academic in nature or whatever. You know, I'd, I'd call all the rest of the stores and I'd figure out if there's a systematic problem with our fridges. You know, I would analyze the data. I'd look at the sales that we're going to lose in that store based on the fridge. And I would try to create a new algorithm that didn't have people drop it off in the store and all these answers. And then the people she'd hire every time would be like, I'd go to Potrero Hill and I'd fix the fridge. Or I'd go and stop somewhere else and buy a new fridge and bring it there every time. And she's like, the answer is fix the fridge, right? Find a way to have us have a refrigerated thing as soon as possible, so we can continue to run the business.

• 1:15:50Speaker 00

  And I always loved her question because I thought it perfectly embodied, you know, what somebody would have to do and the kinds of problems they'd have to solve in the way that the action orientation that she wanted. And I think it's a version of what you just said, because I've always thought that that was such a wonderful interview question. And now I can abstract it to what you just said.

• 1:16:08Shane Parrish?

  I love it. What you're really trying to do is, we used to ask this at the intelligence agency in some of our interviews, which is like,

• 1:16:17Shane Parrish?

  we're going to use a different question than we use, but like, how would you break me out of a third world prison?

• 1:16:22Speaker 00

  Yeah, yeah.

• 1:16:23Shane Parrish?

  Which is what we're really trying to figure out is, are you resourceful?

• 1:16:28Speaker 00

  Totally.

• 1:16:29Shane Parrish?

  Right? How do you think through problems that you've never encountered? Not no way of like, how do you move Mount Fuji? Because like, I think those are easy to prepare for and

• 1:16:39Speaker 00

  Yes.

• 1:16:39Shane Parrish?

  But this is like, how would you actually do this? How would you fix it? Like, how would you fix this problem? Well, I'd buy a fridge. That's a simple answer that's effective and works. That's amazing. But it's surprising that that answer is not the, that answer is not the standard.

• 1:16:55Speaker 00

  I know. And, and to your point, yeah, like I, I always, one of the things I tell people who I work with, you know, I'm like, guys, this is not gymnastics. There's no points for degree of difficulty.

• 1:17:06Shane Parrish?

  Yeah.

• 1:17:07Speaker 00

  Let's just go, let's just get to the, the right answer. Let's go. If it's hard, it's hard. Cool. But sometimes it's not hard. Let's just do the thing.

• 1:17:14Shane Parrish?

  Well, that's easy. It's, actually, it's interesting. You mentioned that you said that there's no points for degree of difficulty. One of the things that I've been Playing around with in my head lately is that most of the people that I think of as exceptional decision makers, consistently good decisions,

• 1:17:36Shane Parrish?

  find themselves in consistently good positions.

• 1:17:40Speaker 00

  Yes.

• 1:17:40Shane Parrish?

  And when you're in a consistently good position, all of your options basically are good.

• 1:17:47Speaker 00

  Yeah.

• 1:17:47Shane Parrish?

  You're never forced into a bad decision. And when you're in a bad position, there's like one hail Mary that might get you out, but everything else is just going to go from bad to worse.

• 1:17:57Speaker 00

  Yes.

• 1:17:58Shane Parrish?

  How do you react to that?

• 1:18:00Speaker 00

  I think, I think that it is generally true in my, look, I mean, you have a lot more experience actually than I do in thinking through this and talking to people. So the reason that I find myself largely agreeing is I think the really good decision makers, what they do is they're very good at identifying the one-way doors versus the two-way doors. Right? And on the one-way doors, their metric is, you know, speed. And they're sort of like, I need the feedback as soon as possible. Or sorry, on the two-way doors, their feedback mechanism is just like, I gotta, I gotta optimize for speed. I gotta make this one quickly. I don't care if it's wrong. If it's wrong, we'll fix it. Right? One of my big things is you can bounce back from any mistake other than a mistake of integrity. If you don't make a mistake of integrity, you can really actually just like fix almost anything.

• 1:18:44Speaker 00

  Right? And then I think those same decision makers on the one-way doors, they're super thoughtful. And they, they get them right. They get them right more often than they don't. And the only reason that I hesitated on, you know, are they always in good positions is there were definitely a couple of times where we felt like we did not have a great option at Instacart, right? And I've seen good companies that don't feel like they have a great option. I think the thing that I admire when people have that though, is they kind of make it into a good option. So when Amazon bought Whole Foods, that was a terrible moment for us at the time. Right? We, our blood competitor who's known for annihilating everyone in their way,

• 1:19:29Speaker 00

  buys our biggest partner who owns, who has responsible for 43% of our volume. And we are afraid we're going to go out of business, right? At that moment, we don't actually have a great set of options, right? We can't get Amazon not to buy Whole Foods. We can't get Whole Foods to at some point not work with us, right? So 43% of our volume is now gone. I think what we did a good job of was, okay, our only way out is if this is the impetus for other grocers to work with us. That's the only way out of this problem. Okay, let's go make sure that we have left everything on the field to go get that to make that happen. So now every week, we're gone. We're in Grand Rapids. We're in Lakeland, Florida. We are in Idaho.

• 1:20:12Speaker 00

  We are everywhere, over and over and over again to meet them. And it ended up being an amazing impetus. We had a good pitch. They, over the next 12 months, everybody signed up with us. But I don't think that at the moment, it was that that was a great option. But I feel proud, I think, as a team, that we were able to turn it into one. So that's the only reason I hesitated on what you said. But I agree with it, generally speaking, because I think that they're just, great decision makers are good at identifying one-way doors versus two-way doors. And getting the one-way doors right, but then on the two-way doors, just realizing that speed is the main thing.

• 1:20:48Shane Parrish?

  Keep going on the great decision makers. You hang a lot, well, you work with a lot of them as a profession. You're exposed to a lot of different types of people from a variety of different backgrounds. I'm curious if there's common traits you see amongst the best decision makers that apply to decision making.

• 1:21:06Speaker 00

  Totally, yes, yes. I very much, I'm excited that we're talking about this because I think it's a big deal. And I take pride, I hope, in being somebody who is a good decision maker, right? So I think that the good ones, one, I think a lot of them use writing, just like you've said. I think a lot of them write, and they kind of write for themselves. Because it reflects the, it reflects the, it exposes the weaknesses of their process. And so one trait that I found for a lot of the good ones is you'll ask them something, they'll be like, let me show you this memo I wrote. And the memo won't have been distributed to anyone. It'll just be for them.

• 1:21:51Speaker 00

  And so I think that's one trait that is pretty interesting, that is. Relatively consistent amongst people that I really admire is that they they test their thinking for themselves. They're very honest with themselves about where it's strong versus where it's weak. Right? The second thing is they're actually pretty good at figuring out whose advice they want and whose advice they don't want. I think a lot of great decision makers, they they are not polite when it comes to the decision. They just decide whose opinion they care about and they're super targeted and thoughtful and it's different people for different topics. Right? Maybe there are some people whose counsel they keep for everything, but it's not a lot.

• 1:22:33Speaker 00

  And I'll give you an example of someone I work with who I think is a very good decision maker. Max Rhodes is the CEO and co-founder of Fair, this B two B wholesale marketplace that we're involved with. Max is extremely good at asking each of his board members or advisors a specific question that they he thinks they will be useful on. He doesn't ask the whole board when he's making certain decisions. He goes and decides who is the right person to go ask. He goes and spends real time with them on that. And even in the board meeting, he's thoughtful about the order in which he asks for people's feedback. Right? Because he's like, look, on this topic, this person is the one who I want to hear the most on. Whereas on this one, somebody else might be the topic. And he's not worried if it's been three questions and he hasn't asked somebody something.

• 1:23:18Speaker 00

  You're on the board, you obviously are somebody whose opinion he values. Cool. So that's another one. I think they're very thoughtful about whose counsel they keep.

• 1:23:27Speaker 00

  I think the the third one is they are aware of when their decision making. They're aware of concepts like decision fatigue and they they sort of

• 1:23:41Speaker 00

  they they work around it. Right? So they say, OK, look, I I'm sure you've read the Bezos stuff of Bezos's point was like, my job is to make two or three good decisions a day. Well, what that means is I should structure my entire day around making sure that I'm in the right state of mind to make those decisions. My meeting should be at a certain time. Right? I should.

• 1:24:02Speaker 00

  I think the point of this is they don't confuse activity with insight. They don't just go do stuff. Right? They do things that they think will help them make the right decisions. You know? And then the last one, Shane, I think. Is they are very thoughtful about what uncertainty they're willing to live with and what uncertainty they're not. So I'll be more specific here. Every good decision maker is good at making decisions in the face of uncertainty. Right? Otherwise, it's not a hard decision. One time, Michael Lewis wrote an article about the presidency. And effectively, what he described it was he's like, look, it's a series of fifty one forty nine decisions or fifty fifty decisions. Oftentimes, they're life and death. Because otherwise, they would have been made by somebody else. So they're like really hard, you know?

• 1:24:45Speaker 00

  But the thing that I think really good decision makers do is they know how to get all of the available information by asking the right questions. And when someone just sort of like, it's a hard decision. Here's what we here are the two options. They don't just accept those are the two options. They'll be like, well, wait a second. On this one, let's go deeper. Did we evaluate this? Did we evaluate this? So they're almost good at like efficiently getting the information they need so that, yeah, there's uncertainty. But it's the only it's uncertainty that can't be solved in the time period they got it. So those are some things that come to mind.

• 1:25:20Shane Parrish?

  I love that. There there's a couple of things that came out of that that I want to talk about. One, structuring your day to match

• 1:25:30Shane Parrish?

  either your goals, your energy level, your what's most important, however you want to think about that. I'm always struck by how so few people structure their day in a thoughtful, conscious way. And how many seemingly high performers Yes. Put a lot of conscious effort into, you know what? I'm best in the morning, so I'm going to make decisions in the morning. I get really tired around two, so I'm going to go to the gym around two. And they structure their day in a way that sort of works for them in a very thoughtful approach. I'm curious as to what you've seen and what you think.

• 1:26:09Speaker 00

  Yeah, so I'll give you an example from work now. Uh, so venture capital in many ways is a decision making business, right? You know, there are going to be some, everyone knows the stats, but effectively like one, you make forty or fifty investments in a fund. One of them is worth more than all the rest. Right? Okay, so you got to get them right and got to get in the right companies, whatever. So the decision making, you know, apparatus is important.

• 1:26:35Speaker 00

  So one of the things that's funny is at some places, there'll be an important decision and someone like, "Well, we gotta hurry up because we have a meeting coming up after this." Think about how crazy that is for a moment, right? Of like having a time around like, how much time should you spend debating whether or not to make the most important decision of the year? Well, that's insane. So like our partner meeting times, they don't have an end time. There is no back end. They go as long as they go. And that, I think, is a really thoughtful, small thing. They start in the morning because the same point, we all think we're better in the morning. And they go as long as they need to go. And sometimes if we're not getting to an answer, we won't be like, "Well, we gotta make it today." We'll be like, "Guys, we're not getting somewhere.

• 1:27:18Speaker 00

  Let's break and let's meet again tomorrow morning on it." And I think the point of sort of realizing that you're not like a slave to your calendar, but your job is to make a good decision. That is one example that I really like because there's a real respect. Sometimes if the memo is distributed late, right? We generally try to send a memo that's thoughtful and deliberate and detailed on Fridays before our Monday decision meeting. Sometimes it's not possible. People get the memo out Sunday night because they have to. They're doing a ton of stuff. We'll be like, "Well, let's just not have the meeting until everyone's read it and internalized it and thought about it." You know? And I think that maybe when I worked at McKinsey, this is my first job was at McKinsey, that one person told me like,

• 1:28:01Speaker 00

  "You have to be willing to release your agenda and just like kind of have the meeting that needs to be had." Because a lot of times people are just like, "Well, we're on point one. We gotta go to point two. We gotta move to point three." That's not the way that, that doesn't reflect reality of the difficulty or the importance of each thing, right? And so I think those would be a couple of examples that I think come to mind that I like a lot, which is, "Why don't we just move the meeting after this? Or let's just not even put a meeting after this? Or there's no constraint on our need to do it now." And just kind of thinking about that and not putting artificial stuff around.

• 1:28:36Shane Parrish?

  I like that a lot. That's very useful and practical advice for everybody out there. The other thing that sort of struck me about your answer is something you didn't say, which I'm curious as to how you think about the trade offs between short term and long term and how they affect decision making.

• 1:28:55Speaker 00

  I might be contrarian in this, but I think that- Most people dramatically overestimate the impact of most decisions. Right? Like, I think most short-term decisions don't really matter. And so the number of times that I will say I don't care about something is pretty high relative, I think, to most people. And I think, look, to be fair, Shane, that's different than a perfectionist. I am not a perfectionist. I am not. That's not like my Enneagram or whatever. And so some people are sort of like, the way you do anything is the way you do everything. Everything is important and we gotta get everything. We need to have a really tight process around all that. I am not like that at all. So many things where someone say, I don't care. It's fine. Whatever you want to do is fine.

• 1:29:40Speaker 00

  Whatever you want to do is fine. And so a lot of decisions I don't even care to make. And I'm perfectly happy with whatever somebody wants to do. And so, and they tend to correlate with things that are short-term and two-way doors. Right? If they're short-term and two-way doors, cool. Like, whatever happens is fine and we'll figure it out. And then if it's, if what you just said is not right, then, you know, cool. We'll just fix it. And then if they're long-term, they tend to be correlated with more one-way doors in nature. And then I pay a lot of attention. So the reason that I tell you on the investment thing that I pay a lot of attention is like, we're not gonna not, once we invest in the company, right? We're in. We're in for, you know, 10-plus years.

• 1:30:25Speaker 00

  And it's not just in investing, it's sort of in anything where there's a big, important, long-term decision. And so maybe to your point, I think, I didn't say it because maybe by nature, the only decisions that I think really, that I'm super thoughtful about, you know, are the long-term one-way doors. The other ones, I'm actually more, I'm like interested in velocity as much as anything else. And there are occasionally things that I care about, in which case, you know, I will. But I also think that you're more likely to listen to me if I don't always push for my way. And I'm kind of like, there are three things a year I really care about. Please listen.

• 1:31:08Speaker 00

  I'm telling you now, this is one of them, you know? And I also really believe in this idea of like reasonable minds can differ. You know? That's fine. But on like really important ones, I wanna, you know, have a voice that matters a lot. I wanna consider it and I wanna treat it like I care.

• 1:31:28Shane Parrish?

  I like that a lot because if you care about everything and you care about everything equally, then you're not caring about the most important things either to you or the company or life in terms of how you think about that. I have a good friend who gave me this advice a long time ago, and it was about his partner and how they argue. And he said, when they catch themselves arguing, they would basically, they can't say seven, but they would rate how important it is to them on a scale of one to 10.

• 1:31:56Speaker 00

  Yep.

• 1:31:57Shane Parrish?

  And he's like, very rarely was it ever a tie.

• 1:32:00Speaker 00

  Yes.

• 1:32:00Shane Parrish?

  And often I'd be like a six and she's an eight. And it's like, oh, well, then you decide, right? Then it just becomes sort of this, this fast track pass out of that.

• 1:32:09Speaker 00

  I actually saw that. There was, the co-founders of HubSpot gave an interview and I think it was Dharmesh who said this, but it was effectively the exact same thing. Hey, when, when they disagree, rate it one to 10. If you're a 10, cool. Just do it your way. If we're both 10s, which like does not happen very often, then let's debate it as long as it takes. And until we knock down, drag them out. And then if it's in these areas, you decide. If it's in these areas, I decide. Right? But I, I really, that goes a long way with me because I think that

• 1:32:45Speaker 00

  there is a human element to the decision making too. Right? And I think that people have got to feel like their opinion matters. They got to feel like their opinion is valued. And I think that you actually can do that a lot by saying, sure, like it's, you don't even need to tell them you disagree. Let's, yeah, cool. That sounds good. And they're like, well, what do you think? Well, I probably wouldn't do it exactly that way, but like, that sounds as good as any other idea. Let's, let's try it. And I think that you can gain a lot of trust with people, which you started this with, by really telling them, like, I do trust you. I, I, I'm not going to be second guessing you after that. I want us to do it the way you're saying. Right? And, you know, let's see. But I think that then you also have.

• 1:33:31Speaker 00

  You have a framework that someone can understand. It's the same thing we were talking about earlier about the home personality versus the work personality. It's hard to create your algorithm to assume, to predict how they're going to behave. Except if you do this, you actually can have a pretty good algorithm. If someone can predict pretty well if I'm going to care.

• 1:33:48Shane Parrish?

  I like it too. It's also good for self-awareness. I find it moves you to the end of the bell curve in either way, which is I either know a lot about this thing, which is why I care about it, or I don't know a lot about this thing. And I I'm caring about everything, which is a sign if you're reflective that you're you're probably missing the element of whatever it is that you're talking about that matters.

• 1:34:12Speaker 00

  Well, and in that case, like, you know, this happens all the time where a founder or someone you work with, they will ask you a question. And you have, and remember, you have very little context. You're not in the organization. You don't know what any of the people are thinking. And so first, to give a really strong opinion is pretty bold, right? Because you don't know a lot of what's going on. And they actually might know a lot more than you specifically about the content. So I think a fair amount of the time, the answer when it comes to that is like, well, here are the things that I would be considering. Here are the dimensions that would inform my decision. But I actually know less about those dimensions than you do.

• 1:34:54Speaker 00

  So like, the framework I'd use is this, if you use that framework, what would it come out with? Right? You're almost trying to help on that dimension. And then, once a year, when you say, please, hear me, I think, I know I don't know as much about this as you do, but I really still feel like this is something we should do. They pay attention, right? They don't always do it, but you've earned the right for them to listen because you don't say it all the time.

• 1:35:19Shane Parrish?

  One of the words you used there was stood out to me as important, which was you used the word velocity and not speed. Why'd you choose that word?

• 1:35:29Speaker 00

  I don't know if this is correct. I'm not a linguist. When I think of velocity, I think of throughput. I think of sort of, you know, this, this concept of, it's almost like I'm training the machine, you know, to make decisions. I want as much feedback as possible so that I can input that feedback back into the machine so that the next one's better. And so somehow, it's like I want that machine turning as many times as possible. And I don't know if that's specifically like more correlated to velocity than speed. But the word that's in my head that keeps on coming to is throughput, throughput, throughput. On the two-way door, short term, I want throughput to like inform.

• 1:36:13Speaker 00

  You know, I want as much feedback as possible to inform the next one. And I just want to get a little better, a little better, a little better every time. One of the things that's interesting is,

• 1:36:25Speaker 00

  you know, the speed of, you know, the speed of shipping, the speed of people actually creating new things and putting them out into the world. It seems to be very correlated with the ultimate success that a company has, is like shipping velocity in the early days. And so I think I tend to apply that into the decision making. And I think that that is, that's probably why I said it. Or I was just trying to sound smart with you, Shane, and use velocity instead of speed. One of the two.

• 1:37:01Shane Parrish?

  You, let's switch gears a little bit here. You work with a lot of exceptional people. What are the ways, what are the common ways that you see them self sabotage?

• 1:37:12Speaker 00

  A very good friend of mine gave me a book called Ego is the Enemy,

• 1:37:19Speaker 00

  which it came to mind when you said this. I think that

• 1:37:27Speaker 00

  one way that folks self sabotage is thinking your past knowledge is enough, rather than treating the problem at hand like it's hard and deserves study. I think a lot of times people overly pattern match from the past, particularly in an investing business.

• 1:37:50Speaker 00

  And they sort of think that they have the ability to be right because they were right before. And it's like, no, like you gotta go earn it each time. It's like thinking that because you were good at shooting threes in the past, you're going to be good at shooting threes today. It's like, no, you gotta go do it today. It's not about what you did yesterday. And so I think that sort of having the, a belief that something is beneath them in the work, or having a belief that the past success will make it possible, I think is a self sabotage.

• 1:38:27Speaker 00

  I think the, another thing

• 1:38:31Speaker 00

  that comes to mind is um management is really hard and I think that I think people sometimes choose to be loved rather than respected. And I think that uh when you

• 1:38:47Speaker 00

  when you do that, you you optimize for people liking you in the moment rather than respecting you in the long term. And I think that what I, what I, what I mean by that specifically is I think all you can really do as a leader of a company is have people believe that the decisions you're making are always in the best interest of the company. And I think anything you do that breaks that algorithm, anything, I think it might serve you in the moment and then it ultimately

• 1:39:17Speaker 00

  comes back to bite you. Cause every leader I've ever really respected, every single one.

• 1:39:24Speaker 00

  I know why they're choosing what they're choosing. I know what the North Star is and it doesn't change. And I think that, like you said on successful people, I think that sometimes they I, I, that to me is a version of, you know, choosing appreciation or choosing affinity in the moment rather than choosing the right thing, the obligation for the long term, you know, and so I, I think that applies to parenting. I think that applies to a lot of stuff like my parents were very different in parenting me versus my brother. And I was pissed when I was in high school about that. I was really upset and I was like, you know, smart enough to make a coherent argument.

• 1:40:06Speaker 00

  Like this is not fair. You treat him differently than you treat me. This is not fair. Right? Where are your kids? You're supposed to treat us exactly the same. And I remember very clearly my parents saying, one, we think we treat you guys pretty similarly, but if you don't, fine. But our job is not to treat you the same. Our job is to try and get the most out of you in the long term, right? That is our job. And if that means treating you differently now, we are happily going to treat you differently. It's not a science experiment. It's not an A B test. Right? You know, you guys are different. We're gonna do it differently. I don't care if you're mad. Man, I'm really happy they did that now, right? We are different. And I think that showed a lot of courage at that time. And I think that, um, but I, I guess my point would be like, I think they could have easily like,

• 1:40:52Speaker 00

  improve the relationship with me as a 14 year old by being like, you're right. That's a really good point. Well, it's, you know, cool. We'll do it that way. So those are a couple of things that come to mind. I don't know if they resonate, but those are two things that come to mind.

• 1:41:04Shane Parrish?

  Well, that example definitely resonates with me because I'm, I'm sort of going through that with my kids right now, where I'm getting a little pushback on, I'm treating them differently. And it's all with the intent of sort of putting them in the best position possible for success, given who they are, where they're at, their strengths and weaknesses. And it doesn't always come across as perfectly fair. And I think, you know, my argument is, uh, life isn't fair, which is what my parents told me. And it's like, I never thought of phrasing it in that way. I like that a lot better.

• 1:41:35Speaker 00

  It, that one really sits with me a lot because I remember how upset I was that then. And I really am grateful in that respect that they didn't take the reaction of a 14 year old and have it impact the way they did it. And they did what they thought was best. Now, whether it's right or wrong, who knows? But I like that they sort of had the courage of their convictions there and, you know, didn't just listen. And again, at least again, that trust point, we keep on coming back, but so much of it is just like trusting why somebody is doing something. Cause then if you disagree, at least you're like, all right, cool. Like I, I think, I, I think I mentioned this to you in one of our phone calls, but like,

• 1:42:19Speaker 00

  you know, my wife and I, we, we never really fought much, but before we got, before we had kids, like whatever level of fighting it was, it was slightly higher before we had kids than after, which is a little weird because kids are like a stressor, you know, in some ways. But the things that would happen beforehand would be, we'd discuss like career stuff. And it'd be like, well, what's better for your career? What's better for mine? My wife is a doctor. And so you can imagine all the different things that you could optimize for. Is it economics? Is it impact? You know, is it, you know, your turn, my turn, all, all these things.

• 1:42:52Speaker 00

  After we had kids, we basically never had an argument about that. Not once. Well, why? We have arguments about other things. We never had an argument about like, what do we go do? And the reason is actually simple. We actually both very clearly know what the optimization function is. Both of us have the same one. What is best for the family? If Avneet tomorrow was like, we should move to Alaska. And, you know, I would kind of be like, I don't really want to move to Alaska. But, but why do you say that? And I would be pretty open minded because I would know that she has done some calculation in her head that that's better for the five of us. Right? And so you can hear something that's kind of a cuckoo idea on its face. And you're like, no, I'm listening because I know that we have the same goal. I know that. I know exactly why you are.

• 1:43:36Speaker 00

  I know exactly what you're trying to accomplish. That is so powerful. Right? That to like, have that understanding and that trust. And so I think maybe the things that people do to self sabotage themselves, they, they fall into anything that breaks that trust with the people around them. That breaks that trust and breaks that ability to predict why they're doing what they're doing.

• 1:43:58Shane Parrish?

  I have the, the luxury of knowing we're going to have another conversation like this that we record. So I'm not going to try to fit all my questions in, in the remaining time. I do want to end this, this version of our, our interview with, what does success mean to you?

• 1:44:15Speaker 00

  Success for me means that the people that are most important in my life

• 1:44:21Speaker 00

  feel like I gave them everything I had

• 1:44:30Speaker 00

  all the time. Right? I think that

• 1:44:34Speaker 00

  that they feel like that they know how much I love them, that they know how much I care for them. And that I

• 1:44:45Speaker 00

  that that comes through. And that it's not something that they know because of grand actions, but it's something they know because of every day-ness. Right? It's something that they know because of the

• 1:44:59Speaker 00

  just that I showed up for them. You know? That would be success. And then I think. I think even professionally, I think that that is kind of similar. Like, the person I admire the most professionally, at least from a distance, is Bill Campbell. The way that people talk about what he did for them and how much he cared for them and, you know, what he meant to them, that is an impossible standard that I will never, ever, ever reach. But that, to me, is a pretty amazing professional hero to have.

• 1:45:38Speaker 00

  So those would be the things I'd say. And I will tell you, I feel very, I'm very proud that you said that you'd want to do this again, because I really love the show, I love The Way You Think. And I was very happy when you emailed me to ask me if I could be on it. And I also would love to do it again.

• 1:46:03Shane Parrish?

  Thanks for listening and learning with us. For a complete list of episodes, show notes, transcripts, and more, go to fs.blog/podcast, or just Google The Knowledge Project. Recently, I've started to record my reflections and thoughts about the interview after the interview. I sit down, highlight the key moments that stood out for me, and I also talk about other connections to episodes and sort of what's got me pondering that I maybe haven't quite figured out. This is available to supporting members of The Knowledge Project. You can go to fs.blog/membership, check out the show notes for a link, and you can sign up today. And my reflections will just be available in your private podcast feed. You'll also skip all the ads at the front of the episode.

• 1:46:49Shane Parrish?

  The Front Street Blog is also where you can learn more about my new book, Clear Thinking: Turning Ordinary Moments Into Extraordinary Results. It's a transformative guide that hands you the tools to master your fate, sharpen your decision-making, and set yourself up for unparalleled success. Learn more at fs.blog/clear. Until next time.