This is like one of what I would consider the most significant lies we've all been told. I spend a lot of time thinking about problems. Paradoxes contain a lot of that. When you think about something that looks on the surface one way, but in reality, it's another way, that's fundamentally what we're talking about here.

It's not about coming up with the right answer. It's about asking the right question and about struggling with it slightly better than you were previously. The advice paradox is the idea that we all get and receive a whole lot of advice. Most of it is complete garbage. So what you're left with is a worse idea of what the overall answer is.

And so the real key then is let's talk about the opportunity paradox. The idea here with the opportunity paradox is you need to take on less to accomplish more. If you had to accomplish your 10-year goals in the next six months, what would you do and how would you do it?

Zaho, thanks for being here. Glad to be back and in the new home studio even better. I know, we're building the sauna out front and the construction has been paused for two hours for us to record. Next time I come here, I expect to do a sauna episode, though.

- Yeah, it's... - Sauna cold plunge? Yeah, one, two. Yeah, the company building the sauna, everyone will hear about it later. - It's called Haven Saunas. - Okay. And it's going to be really nice. - Yeah. - They're doing really great work. But next time we'll do it. It's always trouble to narrow down the scope of these conversations because you've written about so much and I'm an avid reader of yours.

But I was thinking about the topic today and I thought, there is one topic that you've written about on Twitter that has actually led to tremendous amazement of a lunch with a billionaire. So maybe we just start with what is that topic and why should we talk about it?

So I think what you're alluding to, because it's the only one, is the topic of paradoxes. And the funny story around all of this and the lunch with the billionaire story goes back to, let's see, November of 2021, I wrote my first... This was like a Twitter thread on the topic of paradoxes.

So basically, a paradox is like a seemingly absurd or contradictory statement that once you actually dig into it and investigate it, may actually prove true. I wrote a sort of curation of like 20 of my favorite paradoxes that I feel like I've come across in my own life or that I've struggled with on a regular basis and shared it.

And it went pretty viral at the time, probably had like 60 or so thousand likes, reached tons of people, etc. Went away. Just like most things do on Twitter, it's kind of an ephemeral platform. Once something has buzzed for 24 hours, it sort of disappears into the ether and it's gone forever.

So fast forward to January 2023, I am in India visiting my grandmother. And I wake up in the morning to a bunch of texts from friends saying like, "Whoa, Bill Ackman shared your tweet thread." So I expect like, "Oh, it's some recent thing that I've written. That's cool." I pop it open and I look, and he has quote tweeted this thread from November 2021, saying, "A friend sent me this last week.

It contains tons of wisdom. Everyone should read it." And so I'm like, you know, I'm the big like shoot your shot guy. I talk about that a lot. Closed mouths don't get fed is like one of my mantras on life. So I reply to his tweet and say, you know, "Thanks for sharing my work, Bill.

We should get lunch in New York sometime on me." You know, kind of tongue-in-cheek like he's a billionaire. I'm obviously not. I'll pay for lunch. And he replies and says, "Would love to do that." And so we DM, coordinate, and I end up getting to have lunch with Bill Ackman as a result of this Twitter thread that I had written 18 months before, whatever it was.

Unbelievable serendipity and also a perfect example of like the luck raiser, which I feel like we talked about on our last episode of expanding your luck surface area and how content is a great, great example of that. You put something out into the world and it's still creating lucky encounters for you 18 months into the future.

Yeah, so I can't promise that anyone listening is going to be able to use this content to have lunch with a billionaire, but... Maybe. Maybe, but I can promise that the value you get from it's tremendous because I've gotten it. So what I thought we'd do, similar to the last time when we talked about raisers, was just kind of run through what I thought were some of my favorites.

If I miss some, you can bring them up and I've kind of grouped them into a few categories. And so maybe talk really briefly why paradoxes, what attracted you to write about this? You kind of defined it briefly, but... Like for me, when I think about content more broadly and the content that I create, my whole goal is not to provide answers to questions for people.

You know, I don't sit down and think that I am some unbelievably wise or intelligent person that has all the answers to how to live your life in a better way. What I do know is that I spend a lot of time thinking about problems and thinking about struggles that I've encountered in my own life and about tensions and balance points and all these different areas.

Paradoxes contain a lot of that. Like when you think about, you know, something that looks on the surface one way, but in reality, it's another way, that's fundamentally what we're talking about here. And that's life. And so I thought the paradoxes piece and my writing on it was like a great encapsulation of how you actually encounter challenges and struggle in your own life.

It's not about like coming up with the right answer. It's about asking the right question and about struggling with it slightly better than you were previously. And so that's like, that's always been my attempt with writing about it and hopefully what has come across and why it's resonated with people when I have.

It's funny, I think when you just started saying that, it made me click why I appreciate your content so much. What I do is actually probably the exact opposite. I'm like, I am going to do all the research on all the cell phone plans in the country to except for Xfinity Mobile, which a few of you have reached out and said, sorry, I left it off the list.

I guess that my hatred of Comcast kind of came to fruition with the goal of like, can I narrow down all the information so you can actually just make a decision? And I think your style of content is like, let me give you a bunch of information that you can use to think differently and maybe mine is that you can use to do differently.

I mean your content, there's sort of like two areas, right? Like your content is answerable. Like there is a specific answer that you can research and give someone the best answer to definitively the type of questions you're wrestling with. The questions I'm wrestling with are like how to live your life better or you know, like how to live in a slightly healthier or wealthier way and there's no one-size-fits-all to that.

I can research it all I want. You know, I can go talk to like 90-year-olds, 80-year-olds, like learn all that I can, but the reality is that everyone's life situation is different. Everyone's in a different season of their own life and so what the correct answer for you at age 20 when you're starting out is not the correct answer for you at age 40 or may not be and so my whole perspective is like I always need to navigate and avoid being like overly definitive and providing an answer and you know, reconcile the fact that I'm 32.

Like I don't have all the answers. I'm not, you know, like a 95-year-old old wise monk living in the mountains of the Himalayas telling you that I've like learned the secret to life. What I do know is that I spend a whole lot of time thinking about these things and that I have a way where I can sort of disseminate them, you know, and hopefully like a clear and concise way that helps people navigate them in their own lives.

Yeah, so at the risk of taking too much advice, let's jump into the paradoxes. Let's talk about the advice paradox because good transition. Yeah, I feel like advice isn't what it might seem. Yeah, I mean the advice paradox is the idea that, you know, we all get and receive a whole lot of advice over the course of our lives.

Most of it is complete garbage and the more advice you take, the less well-informed you actually are and this is something that's counterintuitive. You think like, oh, I'm just starting out in my life. I need to go and get tons of advice from all these different people and the reality is that for them, most of their maps that they're going to provide you with, the advice that they provide you being the map, are not going to match the terrain of your life.

Your life is fundamentally very different than whatever it is you're going to encounter. Nassim Taleb talks about this idea of like the noise bottleneck in some of his work, which basically says that you assume that by consuming more, you're going to get more signal as a result, but the reality is that by consuming more and in this case consuming more advice, the ratio of noise to signal actually increases over time and so what you're left with is a worse idea of what the overall answer is and I really feel that way with advice.

When you go out and get too much advice, you get too many different perspectives, you actually leave feeling like, oh my God, I'm completely overwhelmed and I have no idea what the answer is to this problem and so the real key then is figuring out how to take some of the signal from what you get out in the world, sort of like narrow down to the things that are really high signal and the people that are really providing, you know, the tightest and crispest, crispest if that's a word, advice and leave all the noise, you know, get rid of all that other noise that might exist in the world.

So is it more about seeking less advice or more about when you seek that advice knowing how to process what you learn? I think it's both. I think on the seeking less advice, that really comes from curating who you seek out for advice. Seeking advice from people who have really experienced the thing that you are going through or have navigated in the way that you want to navigate it and narrowing it down to just those people is really important and then realizing that no one has the ultimate answer for you.

Like, you know, if I want to go start a business, I can't just go to Elon Musk and assume that he's going to have the perfect advice for me in my career where I am, right? Because survivorship bias plays a role, you know, like he might have just gotten lucky and he and you are very different people.

Yeah, and you know, very, very different people and want different things and have different balance points in our life and there's so many differences and yet most people when they go to do that, they go read a bunch of books on business and say like, oh, well, you know, Elon Musk bet it all after he sold his, you know, shares in PayPal and put it like pushed all the chips back in the table and it worked out for him.

Now, he's the richest man in the world. So I'm going to just keep betting it all and then you go bankrupt and you wonder why. So, you know, survivorship bias plays a real role in how advice is given. Like we take advice from the victors and that's a dangerous thing too.

Yeah, it's funny because we're both working on books and mine is kind of at the highest level principles for better outcomes and the first one is that conventional wisdom sucks and I think when I think about the advice paradox, I think about conventional wisdom and I think the most common piece of conventional wisdom that I hear so many people talk about when it comes to money and wealth is that real estate is the best way to build wealth.

I'm sure you've heard this. Maybe people in your family believe it and for me, it's like it is a way and it happened to have worked for someone and then they translate that it to being the best but who knows if they actually did the research ahead of time to pick that, you know, consciously or if it's just the thing that worked.

Yeah, conventional wisdom is an interesting thing. It's sort of like all of these like, have you heard of Chesterton's fence? Like this idea that if you don't know why a fence is there, you should figure out why it's there before tearing it down. I think about that a lot with things like this because so like the example is like if there's this fence and you think it's really stupid that it's there and you go tear it down because you can't figure out why it's there.

It might have been that it was holding back a whole bunch of wolves that you didn't know existed because the fence was holding it back and then you go tear it down and your whole town gets eaten by a bunch of wolves that are let in and so like with stuff like this, like with conventional wisdom, I just always seek to figure out, okay, why is it there?

Like before saying that it doesn't work or that it's incorrect, I want to know like, well, what created the situation where that became conventional wisdom? So like before you dispel the notion, figure out why and then it might be that it was incorrect. You know, like with Chesterton's fence, the whole idea is like no one puts up a fence just for the fun of it.

So they put it up for a reason. You need to figure out why before you go and tear it down. Yeah, it's funny. I chose conventional wisdom sucks. Not conventional wisdom is wrong intentionally because I'm like, it just sucks that people often give it as if it should apply to everyone.

It's not that it's wrong. It's just that you might not be in the same situation as your parents were and so their advice might not apply. And most people blindly give it because it's repeated ad nauseum and so most people will continue to perpetuate whatever the conventional wisdom is because it's easy to do without actually having thought about it on a first principles basis.

And so when you ask them like, well, why? Why should I own real estate and they go to start explaining it. It's like the Emperor has no clothes. There's nothing underneath the surface of that question when you ask them. Okay, so we're in the topic of life. Let's talk about the opportunity paradox, which funny enough as I read through you've written about paradoxes multiple times used to be called the say no paradox has evolved.

Yeah, it's the evolution of a problem of my writing because I think the opportunity paradox has a better ring to it than say no. The idea here with the opportunity paradox is you need to take on less to accomplish more. So when I was young and probably when you were young probably a lot of your listeners you assume that you need to just take on every single thing if you want to accomplish great things.

You need to just say yes to things over and over and over again. I think that is true to an extent early in your life because saying yes expands your luck surface area. You get exposed to different things out there. But at a certain point what you really need to do is take on less and you need to take on less but better to use the Greg McKeon thing from essentialism.

And this is like a really core trait of how you actually go deeper, how you identify what are those asymmetric opportunities that exist and how you pursue those only. It almost reminds me there's another paradox. You have the boredom paradox, which I kind of feel like might fit into if you have extra time because you haven't filled your day.

Would you say that these kind of pair well? Yeah, I think like around all of these it's sort of free time is a good thing. This is like one of what I would consider the most significant lies we've all been told which is that free time is bad. The reality in my mind is that free time is a call option on future interesting opportunities.

What I mean by that is that when you have free time in your schedule you have the headspace and you have the actual time and bandwidth to go pursue the really high upside asymmetric opportunities that come into your life. If your day is just back-to-back meetings chock full from start to finish, where are you going to pursue the interesting thing that might come your way?

You're just going to have to say no to it because you literally don't have time and you don't have the headspace to think about it. I think about that all the time. When I'm stressed because I'm running from thing to thing to thing my response when I see a text or an email that might offer me something or ask me to do something is like default no because I'm overwhelmed.

I'm stressed and I just want to get things out of the way. So creating that like Arthur Brooks calls it like ventilating your schedule like breathing some air into your schedule is a great way to spark creativity so that you can actually go and identify what those asymmetric opportunities are.

The things where you know one unit of input is creating 10, 100, 1000x units of output. Yeah, and if you don't have a thing to come back to boredom it's like actually being bored can be valuable. Yeah, I mean look at this is a silly example. Look at how Lionel Messi plays soccer.

Watch him on a soccer field. This is one of the things that announcers have bemoaned about him throughout his career. He walks around the pitch all the time and to the untrained eye it looks like he's bored. I mean during the World Cup final he's like walking around in the latter seconds of that match just like sort of aimlessly looking around and walking around and then all of a sudden he bursts into action and deploys all of his energy into a single moment where he knows there isn't a 1000x upside potential in that moment and scores one of the game winning goals.

And that is like the perfect example to me. You can be bored and then really deploy all of your energy into those 1000x opportunities that offer that asymmetric upside. Yeah, I think also watching Lionel Messi not moving around probably fits into the effort paradox as well because I think he knows what he's doing.

Yes, he definitely knows. And maybe as we hit each one feel free to recap them. Yeah, he definitely knows what he's doing. You know the effort paradox athletes are the best with this one. So I totally agree with you. The effort paradox is the idea that you have to put in more effort in order for something to appear effortless.

Like the idea that effortless elegant performances are really just the result of thousands and thousands of hours of effortful practice. Watching Roger Federer play tennis in his prime if you're a tennis fan is a perfect example of this. Like his strokes just look completely effortless but they're the result of thousands and thousands of hours of compounded, effortful practice.

There's this phrase which I might butcher the pronunciation of sprezzatura which is an Italian phrase I think from like the 15th century a guy by the name of Baldassare Castiglione who wrote this book called The Book of the Courtier. And the whole book was about how to be an ideal courtier like a person of the court in these royal courts.

And he basically said that people should an ideal courtier should walk with a sprezzatura which he defines as like a studied nonchalance meaning it appears effortless but there is a studied element to it. Like you've worked so hard to make something appear effortless in the way that you walk.

And that is the goal that all of us are pursuing. That's like, you know, reaching that level of like unconscious competence in something where you can just do it and make it appear completely effortless to do the thing. That's kind of the pursuit that we're all on in whatever our field or craft is is to reach that level of elegance in the way that we move.

Yeah, I was I mean, I don't know if you've seen Free Solo but my sport that I've done He's a perfect example of it. I've rock climbed for a long time and the ability to make rock climbing look natural is so much practice. And it's also a great sport to take someone who is very very in shape but has never been rock climbing if you want to feel good about yourself.

So you're going to take me rock climbing sometime. I get invited to do a lot of rock climbing and I always hesitate because it scares me. But Alex Honnold is someone that I would love to meet someday because just like the way that his mind works around these things is just fascinating.

It's yeah, a venture firm that I raised money from had a private event with Alex Honnold a couple weeks ago and it was really awesome to have like a small group non-recorded closed-door conversation. He is a fascinating individual. I mean the cinematography in that movie is otherworldly. I think it was Jimmy Lee or no, it's Jimmy Chin.

Jimmy Chin is the guy that does it who's an unbelievable climber himself and for the whole team to be able to actually get those shots unbelievable climbers. But that movie is incredible. I just assume people have seen it but if you haven't strong strong drop everything. It's like a drop everything and watch that movie unless you're like terribly afraid of heights in which case you might get like kind of triggered by it.

Yeah, I could see being yeah. I took a friend of mine rock climbing once just assuming this is I don't there's probably some pair about paradox or lesson in this. I assumed that he would know that climbing gear is safe, but he'd never been climbing. And so we were in Australia and we did a five pitch climb in the Blue Mountains, which is basically five pitch.

Yeah, five pitches you climb up and then you pull your gear and your ropes and then you climb again. It's like five stages and this is where you're like setting your gear in the rock like you're taking a thing pushing it between a crack and trusting that it will hold you having done it myself.

I'm like, yeah, that works my friend. I never rock climbed and we weren't doing necessarily a hard climb if we were in a gym, it would have been like a walk in the park for everyone, but we're like up on this wall and it never crossed my mind that he might not trust all of this stuff and I just remember by the end.

He was I have a I had a GoPro on. He was just cursing me. He was so mad, but there's nothing he could do because we're having a wall. Yeah, there's just no option. I I mean, I'm kind of with your friend on this like on all of these things.

I'm I'm not like a big risk taker in general. And so like when I have friends that do these kind of things, I'm like, dude, you have kids. Why are you doing that? Like, you know, like I've even scuba diving. I'm like, why are you scuba diving? Don't scuba dive.

Just like go snorkeling. You're on the top of the water. You're totally fine. Like, do you really need to get into the fishes environment and like be down there in their house? Like they don't want you there either. Just chill on the top. You don't have like a pressurized tank of oxygen on your back.

Like you're totally fine if something goes wrong. I never understood why people want to go do these things. Yeah, it's funny. I snorkeling scuba diving for me actually was one where I just feel like if you do it enough, I just kind of get bored with it. I guess it's like I've seen a lot of these things.

So it's fallen off. Yeah, and then people go to you know, and then you're like, oh, well now I need to scuba dive in like shark chummed waters. Like so now I need to go do this. It's like, okay. Well, then if you go get bit by a shark, I'm not going to feel bad for you if you decided to go do that.

I will put an endorsement in which you probably won't take. In Hawaii, there is Pelagic shark diving where it's just snorkeling with sharks. So you're kind of free diving and snorkeling in the sharks environment with a marine biologist who knows what they're doing. But it's like, what do you mean they know what they're doing?

Like they're going to wrestle the shark if the shark comes. Like that makes no sense. Why? Like why? Why would you just to see a shark? I mean, it was it was actually really fascinating because it was it was kind of like go get a lesson about sharks and be in their environment.

And I guess it's not control. Yeah, right. You're in the water with the shark. Like what do you do if the shark just comes at you? You just try to run away like you're swimming. She had like a pole. That's really going to stop a shark. That sounds great.

I mean, it sounds like fun. There was one shark and she's like, well, there's one shark with a lazy eye. It's very docile. If it comes towards you, don't be too worried. And so it's a lazy eye. So this shark would swim near people and she just kind of like bop it on the nose and it would swim away.

But I thought you probably won't take me up on it, but it's I believe it's on either the Big Island or now. I can't remember which island. I'll put a link in the show notes. But we did this shark. It was amazing. I'm just going to stick to watching National Geographic.

I'm going to get my like Apple Vision plus immersive experience. It'll basically be like I was in the water with you guys, except without the, you know, shark potentially eating me. Yeah, OK, fair. OK, OK, let's let's get back on track. Let's go to the talking paradox. And and this was particular.

I have a couple anecdotes here that came up recently. All right, go for it. Basic idea with the talking paradox is you actually in order to be heard more, like if you want your ideas to be heard, you should listen twice as much as you speak. And again, it's counter to what you would think, which is the more I talk, the more I push my ideas out there.

If I'm in a room, I need to be the loudest one. I need to get my ideas heard completely counter to that. The people that you actually listen to the most are the people that listen a whole lot. And then when they do speak, it is incredibly pointed, interesting, insightful speaking.

There's some quote. I'm going to forget who it is. Maybe it's Epictetus that it's like you have you have two ears and one mouth. You need to use them accordingly. And it's very true. And something that I think of a lot like in group events, at retreats, at different things that I go to the person that I inevitably leave being most impressed by is the person who said very few words.

But when they did speak, it was unbelievably poignant. Yeah, there was a partner at Google Ventures, Joe Krause, who's one of the I guess I call him wisest people I know. And he had this thing where he didn't talk much. And then when he did right before, he'd kind of put his hands together like this and we'd all be sitting in the room.

That's like a common thread, by the way. I feel like they always are like, OK, talking Yoda. And I just remember we're all sitting around the room and then all of a sudden you'd see Joe put his hands up and I would be like, quiet down and and listen intently.

And I'm curious. I feel like this should be a goal for mine, I guess, being a podcaster makes it hard to be like, oh, I should talk less. But. Do you feel like you do this well? And if so. How much are you thinking about what you're saying? Because I feel like, you know, to go back to Arthur Brooks, he has this whole concept of crystallized intelligence.

And as you, you know, grow in your professional life, you've built up such a wealth of knowledge. I feel like sometimes it can be easy to just speak off the cuff. Do you have any any tips for kind of restraining to really hone and focus when you kind of know the answer?

But if you took a minute, you could piece together an even more profound response. To answer your first question, I think I'm improving at it, but it doesn't come natural to me. I'm a storyteller. Naturally, I love, you know, telling stories, embellishing story, like in locker rooms. Like that was always my thing.

I was like always kind of the loud one in that way. And I need to force myself to go into, you know, what I call listen mode, which is like when you're around people, especially people that have different views than you. You really need to make an effort to listen twice as much as you speak.

And it's really hard to do because when someone says something you don't agree with, your first reaction is like, let me jump in there and contest it. Let me tell you why you're wrong, etc. And you learn a whole lot more about the world, about yourself, about the other person by defaulting to listening in those situations because no one believes something for no reason.

Like when someone has a belief, when someone has a perspective, when there's a fence sitting there, there's always a reason that the fence is there. So I think it's something that we all, you know, I definitely need to improve on. I think we all probably need to improve on.

Your second question on like, you know, kind of ways and tips and heuristics. I think that it's just that. It's like when you're in a situation and you're listening, actually make sure you're listening to the person, not formulating your response in the moment. I think there's a point in time, you know, when you've kind of gotten the gist of what someone is saying, when you kind of turn to, okay, now I'm like, I'm listening, but I'm also creating the narrative of what I'm going to say in my mind.

But it's usually later than you think. Most people, I think, stop listening very, very quickly in someone's dialogue. Like, even when we're having a podcast conversation, you notice, if you start becoming aware of it, at what point in the person speaking are you starting to think about what you're going to say next?

Like you right now, you're probably thinking about like, okay, what am I going to say next? Because it's the natural way that a conversation goes. Learning to like uncomfortably push that back a little bit and listen a little bit longer, I find that you learn a lot more from the other person.

And then as a result, you end up coming up with more insightful responses that sort of drive conversations forward. - Yeah, I just interviewed. It's funny 'cause I want to go back and listen to it. 'Cause sometimes when you're in the moment like this, I'm not always the best at listening 'cause I'm trying to plan the conversation and it's a little bit my responsibility and job even.

But there's a Stanford professor, Matt Abrahams, who his episode will be coming out. By the time you hear this, you'll have heard it. But it comes out, I think next week. And he's written a bunch of books on impromptu speaking and how to become more natural at it. And by becoming more natural at it, you can feel more confident pushing back the point at which you start thinking of what you're gonna say.

- That's interesting. I read an article recently on ways to become a better conversationalist, which I thought was really interesting because it's such an important trait, being a good conversationalist, that you don't really ever study, read about, think about. And it was written by an improv, like a person that is an expert at improv, which is an unbelievable skill.

Like if you've never done it, gone to an improv class, et cetera, it's a great way to get better at public speaking, to get better at conversations, et cetera. And what he talks about, like his mental model, his framework for improving as a conversationalist, it's all about creating what he calls doorknobs in conversations.

Like you say something that is a doorknob that someone else can open and walk through. Like you're not asking them necessarily a direct question, but you're making statements that are inviting someone to open the doorknob and walk through the door. You know, so like he, the article is great, we should link to it in the show notes, but it's got a whole bunch of like really interesting examples of that, like in an improv context of how you create a doorknob rather than just like making a statement or doing something that sort of like closes off a conversation.

It's funny 'cause it might be the same person, I don't remember the name, but after I did this call with Matt, after I did this interview with Matt, he sent me a list and he was like, here are a few people that I think would be great for your show.

And I was like, gosh, all of the topics and mainly 'cause they're mostly other Stanford professors in his department, where one of them was about improv, they were all kind of related to conversational skills. And I was like, gosh, I don't know if I'm gonna have four conversational skill episodes in a quarter, but I don't know, it's really important.

So I'm like, I'm definitely gonna line 'em up. So keep an eye out for at least one more in the future. - Yeah, I do think, I mean improv, it's something I wish I had done at a younger age, like I wish I had done an improv class in college.

So maybe this is very rare, but it was a required class in my middle school. So everyone in my middle school-- - We had drama, actually we had to do drama. - Yeah, and I think maybe it was drama, but I remember playing like park bench. If you ever played park bench, the improv, like, I don't know what you even call, skit?

I don't know, exercise? We would play it in school and you would have to kind of rehearse and, not you didn't rehearse 'cause it was improv, but like it was a thing that we would do in school. And I don't know, I feel like, I feel like this about a lot of education.

There's all these things that I was exposed to in middle school, high school, elementary school, that looking back, I'm like, why didn't I like really appreciate what I was doing? At the time I was like, oh, this is silly. And now I'm like, oh, improv, I should've practiced more.

- I mean, that was what I was gonna say is like, I think we had that too. We had drama and we had to do stuff like that. But I, and I'm sure all of my classmates, were at the time so insecure and so self-conscious that you basically don't take advantage of it.

Like you're not actually building the skill 'cause you're so worried about other people judging you and laughing at you. You know, like I was probably like, I probably had a bunch of zits on my face and I was probably like, you know, trying to hide from some cute girl that was in the class.

I didn't want to embarrass myself. And you know, you're like suffering from the ultimate spotlight effect at that age where you just assume that everyone is staring at you when in reality, everyone is just worried about themselves in that same moment. But like, I would love to go take an improv class now.

Now I might think about doing it. Like I'm sure New York has some of the best improv classes in the world. I think it'd be really fun at this age where I'm like secure enough to not really care if I'm embarrassing and bad at it. - It'd be interesting even to just think about, like I went to a conference last week in Hawaii and it was atypical in that it was not your standard conference with keynotes and that kind of stuff.

And their thing, which was, there's this thing called the game. And the best I'd describe it is like scavenger hunt meets escape room in groups of five. And, you know, you kind of get to know people and you do all these kind of mental challenging exercises, but it'd be interesting at the next kind of conference, summit, off-site mastermind, whatever you call it, to just have an improv person come and do a class.

I don't know. I know you go to a lot of these events. You probably host some of them. That's maybe a really cool idea. - I like that a lot. - I expect an invite. - You're in. - Okay, so speaking of that conference I went to, let's talk about the productivity paradox because I thought a lot about this in a session I led.

So this is all grounded in Parkinson's law, which is the idea that work expands to fill the time allotted for its completion. Basically, when you leave something open-ended and you have the whole day to do it, it'll take you the whole day to do it. And if you bucket it into a single hour, you'll find a way to get it done in a single hour.

The most classic example of this in like our modern work context, I would say is like email. If you allow it to happen, you will spend the entire day emailing. I spent a lot of my life doing this. Like the early years of my career, email would just take the entire day.

Or if you batch email into a single hour, and you're like, "I need to get through my entire inbox in this hour," you will get that done. And so the productivity paradox is basically grounded in that exact idea. It's like less time, you become actually more productive when you can work less and actually get more done.

- Yeah, there was a whole session at this conference. So it wasn't keynotes. It was kind of user-generated conversations, but about productivity, that was one. And then there was another one where someone was talking. I led this talk about the concept of die with zero, focusing on net fulfillment, how to prioritize things in your life.

And someone said, "Oh, sometimes during the day, "if I need some creativity or I just need a break, "I'll just go mountain biking." And someone was like, "Well, how do you just take "two hours off in the middle of the day?" And we talked about, it turns out that if you take two hours out of your day, you can usually just get all the stuff done anyways.

And so-- - I mean, Tim Ferriss, just to, sorry to interrupt you. I mean, Tim Ferriss, I would say, revolutionized this idea with 4-Hour Workweek, because he was the first person that just put on paper the idea of, if you could only work for an hour the entire week, what would you do?

And how would you get it done? He has mastered the art of asking the seemingly absurd question that forces you to scrub away assumptions that you might've had about your work. And I actually went through that exercise. I really thought, okay, if I could only work for four hours a day, I used to work 12 hours a day at a minimum when I was working in private equity.

If I could only work for two hours a day, if I could only work for four hours a day, what would I do? And how would I continue to make just as much, if not more money doing it? And what you realize is that you're spending time on a lot of things that you could either delegate, delete from your life, outsource, whatever, and really focus on the things that are really moving the needle.

And that's what you would do if you only had two hours. Like, gun to your head, if you only had two hours, what would you do? He recently asked one that was, if you had to accomplish your 10-year goals in the next six months, what would you do? And how would you do it?

And that's another one where it's like, okay, all of these assumptions I've had for the long-term nature of anything, how do I scrub those away? And just think about what would have to change in my life? What constraints would have to be removed? What environments would have to be changed for me to go unbelievable monk mode sprint on this given thing?

I just think it's worthwhile to ask yourself those questions to continue improving the overall flow of what your life looks like. Yeah, you mentioned, Tim, I'll give a shout-out to an episode he recently did with Sam Korkos from Levels. He is the master delegator, optimizer, being efficient, I would argue that episode is like a masterclass in all productivity.

Is that the guy that has his day scheduled down to the minute where it's like, you look at his schedule and it's from 6/17 to 6/22 brush teeth? I don't think he actually is that. I think he's more focused on how do I achieve this task? Where do I put it in the day?

How many hours do I spend on it? How do I delegate it to someone else? What's a system for that? Lots of notion, lots of loom, uses maybe the most power user of loom in the world based on that episode. We'll link to that in the show notes. But on the note of moving fast, this monk mode, get everything done, I think the common assumption is, well, if you need to do that, you just need to not stop and just go.

But you have the speed paradox, which says the opposite might be true. Yeah, I mean, the speed paradox actually goes hand in hand here, which is almost like a meta paradox of you would assume that it doesn't. The speed paradox is sometimes you have to slow down in order to speed up.

You know, like move slow to move fast. And I think there's this common, I think it's like Navy SEALs maybe, it's a military phrase that's like slow is smooth and smooth is fast. And that's like where, kind of the ethos of this paradox. The basic idea here though, when you slow down, slowing down is what allows you to identify the high upside, high leverage opportunities that you should deploy your effort into.

So like Lionel Messi, slowing down and walking around the pitch is what allows him to have the vision to see those moments where he should deploy all of his effort. If he was busy sprinting around in a million different directions, huffing and puffing at an 190 beat per minute heart rate, he wouldn't be able to identify those opportunities because his plane of vision would be shifting all over the place.

His head would be bobbing all over the place. It would be really hard to see it. And so when you slow down, your vision gets really clear and you're able to actually identify where those things exist. Yeah, it's so fascinating. Speed is actually something I've been thinking a lot about, especially when I was running a company.

It's like the name of the game in venture-backed startups is like move fast. And there's a guy named James Currier who has an investment fund called NFX, which I think is, he's one of the smartest people I know. And his blog is, you know, pure written gold, in my opinion, if you're running a company.

And he gave this talk once and I'm so disappointed it wasn't recorded, but about speed. And there were a few things that he pointed out. A lot of it is fear. The reason that you sometimes can't move as fast as you want is that you're just not sure how it will work.

And then once you get over that fear, things get unlocked. And I think Roger Bannister is like the example everyone always gives, which is no one ever ran a four-minute mile. 1954, Roger Bannister runs a four-minute mile. And I think within three months, eight more people could do it.

It's like they didn't think it was possible. It just hadn't even crossed their mind. Was it fear? Was it something else? They just didn't believe it was possible. And one of his tips was simplify everything. And so in this slowing down phase before moving fast, and some of these examples are maybe business only, but he's like simplify every contract you use with a vendor.

Like don't write custom things. Say this is what we're using. Budgeting. It's like create a simple budgeting process. But for health, an example I'll use, which I think slowing down to speed up is if you want to really focus on health, slow down, think how do I just make my meals very simple?

How do I make it incredibly easy for me to not be unhealthy? And that takes some foresight, what you stock in your pantry, how you do your shopping, how you do your meal prep. But then it actually makes it really easy to quickly be on track with food goals.

So there was just so much in that talk. If I could turn that into a podcast, I'm like I'm going through in my mind all the things that he talked about. The best example he gave, which was so fascinating about mindset, because he said mind is literally everything when it comes to moving fast.

So if you need to slow down to recalibrate your mind, but he was working at a software company that made video games. And he had a team of 40, and they said it takes two years to make a video game. That was the operating assumption. And he said we're going to ship a video game in 21 days.

And 38 of the 40 people were like no. And two of them were like we could try. And he was like great. This game looks great. I don't know. I think it was like a Facebook back in the day with Facebook games. They just copied someone else's game. But these two engineers and slowly over the 21 days people came on.

They actually did it. And at the end, they were like we did this thing that everyone on the team thought would take two years. We did in 21 days. Now the funny part of the story is I believe they got a cease and desist like immediately after from the company they copied.

But it didn't matter because as soon as he finished, they said great. We'll shut that game down. Now my entire team knows we can build a game in 21 days. We can go build our own original thing. We don't have to worry about that. But those 38 people thought it was impossible.

And so sometimes you just have to like train yourself or test yourself or push past that point at which you don't believe it's possible. And that takes some slowing down and some forethought. So that's a great story. I have a lot of thoughts on speed and how valuable it can be and how just running straight into it might not be the best answer.

Yeah, and it's a broader metaphor for life. Like, you know, there's the idea of work like a lion. Like sprint, rest, and repeat. And the rest is just as important as the sprint. And that's a piece that most people lose sight of is you have to have the rest in order for the sprint to be as efficient as possible.

If you don't have the rest, then your sprint is going to be a jog. And most people and most work cultures default to a jog where you're just sort of like grazing throughout the day. Naval has talked about this. And it's really true. And so figuring out a way to align your overall life professionally, personally, health, physically, all of these different areas into much more of a sprint and then rest system is much more efficient for actually driving progress.

And to go back, we started with the advice paradox. And yes, much advice might not be helpful, but for a lot of scenarios and things you want to sprint on, there are probably some people whose advice is very relevant. And so whether you're building something at a company or you're trying to dial in your health, not taking the time during that slowdown phase to seek out, "Okay, is there someone who's done a very similar thing?

Is there a playbook for it? Is there an answer out there so I don't have to solve every problem myself?" is something that I like to do in that kind of slowdown before sprint mode. And so it could be as simple as, "Okay, if I just sprint into fitness, I don't even know what I would do right now." But if I paused and said, "Okay, is there someone who could design a workout regimen or someone who just has already designed one and published it on the internet or a friend that could just tell me something to do so that I didn't spend all this time swirling around what?" And so I think if you solve the what in advance during your wind down, kind of slowdown time, you can execute much, much faster.

- Yeah, the flip side to it, which you need to be aware of, is that sometimes slowing down and doing all of that kind of research and evaluation is like procrastination in disguise, where like with fitness, you would say like, "Okay, well, let me slow down and figure out the right fitness and health regimen and I'm going to construct the best plan." And the reality is like, you know, it's like kind of like the midwit meme where like in the middle, they're like, "I'm going to, you know, develop a two-tiered functional strength training program that involves hypertrophy," you know, like all these middling things.

And then, you know, on the two ends of the midwit meme, it's like, "Move your body for 30 minutes a day." And you just do that. And so sometimes you just need to watch out for the fact that like, you're not slowing down as a means to procrastinate and like, "Oh, I need the perfect system." Well, you just need to start moving and you can figure it out as you go.

And so balancing those, which again, are in like a little bit of tension, is an important thing. - Yeah, in this talk that we had about "Die With Zero" and focusing on fulfillment, it was interesting. There were kind of two camps and somehow the discussion came up of like taking a year off and traveling with your family.

And two people had done this successfully. One of them went to Europe with their kids and the other one, I can't remember, took a sabbatical and did something. And then the other half of the room was like, "I don't know how to do that. Like, that seems impossible. I've tried." And what was interesting was we ended up having this long conversation about why people don't set personal goals and deadlines and structure their personal ambitions like they would professional.

We've all, almost everyone listening, you and I, we've all been in a workplace where we're like, "Wow, here's a thing that needs to be delivered by a date. What are we gonna do?" Well, we're gonna make sure this gets done in the first week and then we're gonna delegate this thing and this person has four days to do it.

And then we sit down with our family and we're like, "Well, we wanna go on a trip to Europe." It's like, "Cool, we'll talk about that next week." Like, you just don't set up these kind of milestones and structure and, you know, I won't go as far as to call them OKRs, but we just don't have a lot of process around our personal goals.

And so I think it was an episode I did with Ben Nempton who has written this book called "The Bucket List Journal," had this crazy bucket list story, really fascinating guy. And he was like, "People just need to set goals." Like, "What's the next step I'm gonna take towards this personal goal?" And so I think when it comes to procrastination, especially with health and personal stuff, you can slow down.

Like, I'm all for slowing down, but to help yourself not get caught in that procrastination and never make progress, set a goal, set a deadline, which we never do personally. - Yeah, I mean, my book is going to have that incorporated as, like, in each of these domains. And my book is gonna be called "The Five Types of Wealth." It's going to track, you know, your life across what I view as the five types of wealth.

And within each section, it's like, helps you actually identify what are your goals and what are your anti-goals around those, each type of wealth, so that you can go and do that. You can actually create a plan and actually make progress on these things. - Can I try to guess the five?

- No, we don't wanna do it now. I don't wanna reveal all this before the book. - Okay, okay, okay, well, when it comes to making progress in life, we'll not talk about what types of wealth we wanna accumulate in our life, but there is a lot of distraction.

And so I think you had two things that actually came up a little bit in that interview Tim did with Sam about things that can just get in the way of everything. So let's talk about social media and news. - Yeah, both near and dear to my heart for different reasons.

So the social media paradox, or you could call it the connectedness paradox, is this idea that we are, or we have, more connectedness than ever before, and yet we feel less connected to those around us simultaneously. There was a viral video several years ago of Look Up. It's like people just looking down at their phones all day and looking down at screens, and they forget to look up at the people that are sitting right in front of them.

And it's a really sad thing. If you go walk around in New York City, you're weird if you look at someone and smile and say hello. And if you think 20 years ago, that was what you did. You walked around, you tipped your hat at people. That was the way that people lived, and you actually interacted with people face-to-face.

Today, a young person that's trying to date doesn't know how to go up to someone and talk to them in a bar, in a restaurant, or wherever they are. They know how to swipe on their phone in order to meet people. And I mean, it's a really, really powerful trend.

And what I think is happening now is like the pendulum swings. And so you have this environment where everything is through your phones and through your interactions and digital, social media, et cetera. And you have this swing that sort of comes back towards in real life, real human connection.

And it's interesting to watch, and it's interesting to observe, especially with the rise of AI. And so is the lesson, think about it differently or do it less? I think that the lesson is like put your damn phone down more often. And this is coming from someone who, for work, quote-unquote, has to spend a lot of time on social media.

But I really need to make a concerted effort on a daily basis to put my phone down and to be present, in particular, with my wife and with my son. Because it's very easy when you are so connected there and when the dopamine drip is so clear that comes from those things, to just keep your phone on you and keep checking, keep pulling it out, keep looking at the thing.

And that's what they're designed for. Like these social media platforms and social media is a drug. And it's a really effective drug because it continuously feeds you with these tiny little drips of dopamine that make you want to keep coming back. And we need to find a way to disconnect from that in order to connect with the people around us.

- Have you ever experimented with just deleting the apps from your phone and only doing it on the computer? - I've tried. It never has made that much of a difference for me. Honestly, because a lot of my work is through my phone, I like being able to have access to it.

I've tried all the different apps that kind of restrict your time. The iPhone now has a pretty good interface for restricting the amount of time you spend on an app during a day. It requires the discipline to actually stick to it when you've hit the total by earlier in the day to actually stick to it.

But I've been able to create a system that works for me, which is basically like my phone gets put down at a certain time in the evening and that's it. It's down. - And what about news? - So the news paradox is the idea that the more news you consume, the less well-informed you are.

This tends to be a somewhat controversial topic when you talk about it or share it. Typically, you get a lot of people that actually work in media just saying you're an idiot or that's incorrect. This goes back to the noise bottleneck that I talked about to Leb's idea at the beginning, that as you consume more and more news, you're actually getting a higher ratio of noise to signal.

And so your overall understanding of the issue or of the world actually becomes worse despite the fact that you're consuming more, which you wouldn't expect. I have personally found that my life has improved dramatically since I've dramatically reduced the amount of news I consume. And I'm talking like, I cold turkey probably reduced my news consumption about like 95%, maybe like two years ago.

And I feel happier. I like have heavily curated my news sources to where like I read one or two things and I just know that I understand at least like a foundational level about the world. If I wanna go deeper on an issue, I can do that. I know where to do it and how to do it, but I don't feel like I'm hit by the barrage of like breaking news, urgent, blah, blah, blah, whatever all the things are on a daily basis.

And I actively avoid following and consuming from those accounts on Twitter or on any of the relevant platforms. - So how do you use that 5% that's left? - How do I use it? - Yeah, like if you say, well, now I've bound my news consumption to a small amount.

Is it reading people who do a good job summarizing? Is it specific sources? - Yeah, I mean, like I think Axios does a great job as one of the platforms that is really good, but it's basically like one hit per day of like you're getting the basics of the things that are happening in the world and in any different arena you're interested in.

And then from there, if you wanna go deeper on something, like if you think, you know, as the heuristic that I've seen that I think is useful, like is something going to be relevant a month from now? And if so, you should probably try to know more about it.

Most of the news that we see on a daily basis is not relevant more than like an hour later. And everything is labeled as breaking news. Nothing is breaking news if everything is breaking news. And, you know, they use it to get clicks. I totally understand how media works.

So I totally get it and I get the incentives. I get why, you know, they operate the way they do. I just don't wanna be hit by it and polluted by it in the way that I think. If I was going to like get, you know, crazy mentally connected to every single news story that came my way during the day, I would have no time to think about things that I actually care about.

And so I just try to actively avoid it. - Yeah, I think news often also follows the productivity paradox. And, you know, you could learn, if you turned on CNN and not to knock any particular news channel, but you could watch a specific piece of content for three hours and you're not gonna get three hours of knowledge.

I think sometimes I find myself catching myself thinking, "Oh, I'm gonna just consume this thing "that might take a long time." And then just pausing. I think one of the ones for me is, "Anytime Apple does a keynote." And yes, there's some excitement about it, but I find that I'm like, "Oh, I wanna watch the keynote." And I know it's gonna be an hour.

I also know I could read the summary of the keynote at the end in 10 minutes or five minutes and I catch myself. And I feel like anytime you put the news on TV or you could just fall into this trap of somehow they can make a five minute piece expand and fill two hours and it can be mind-numbing.

- I mean, this is the whole thing with CNBC. It's like financial news, right? Where no one is making a return by picking stocks. You know, like most hedge funds aren't making alpha and their entire job is to do that. So like you as a person sitting at home should probably not be spending your time picking stocks if that's not like your exclusive job and you're one of the best in the world at it.

You probably shouldn't. It's not a great allocation of resources and time. And yet CNBC, the entire day, 24 hours a day has people jumping on, trotting up there and talking about stocks that they're interested in and stock picks. And there's this story that I've heard of like someone getting asked this, like, "How can you possibly do this?

Like Kramer's on for all these hours. He has all these terrible stock picks." And you need to reframe it as it's entertainment. Like we have 24 hours of programming that we need to fill. And so we need entertaining people to be up there. And like a lot of news has become entertainment.

It's no longer information. It's like, they're trying to hook you. They're trying to keep you there and keep you entertained. And what's entertaining, but like blaring, breaking news in all red, bold font, sitting across the page. It's not entertaining for them to talk about, you know, the new speed bumps that were put in in your city or, you know, the, you know, Girl Scout cookie campaign that's going on.

What's entertaining for them and what keeps people there is fear. It's like, "Hey, so and so, these many people got killed. This terrorist attack happened, this thing." Like, that's what's keeping people there. And it makes you think that the entire world is that, is that's what's going on, right?

There was this chart that was like comparing actual causes of death to causes of death talked about in the media side by side. And you look at it and like the actual causes of death was like heart disease, cancer, you know, like the actual things. And then when you look at the media one, it's like terrorism, you know, like crime, murders.

Like that was what it was. It was like inverse. Like it was literally like, it was like a parody almost, but it was reality. And it's because what do they report on? It's the things that they think will get people to click and that will stick there. And that's fear.

And if you want to live that way, that consume more of that. - Yeah, I don't imagine the evening news focused on heart disease would be that exciting for the average person. - There was this old movie, like way back in the day, I think it might've been a Michael Moore movie.

Like, I feel like I saw it when I was 13 or 14. I think it was called "Bullying for Columbine" that, you know, politics aside on all of this stuff, like there was just an interesting juxtaposition that I remember he did in it of like showing the news in Canada and then showing the news in the US.

And the Canadian one was like, it was looking at like speed bumps or something that got put like painted differently in town. And then it showed the US one, which was all shootings and crime and all this stuff. So it was interesting. - Yeah, I used to watch PBS News Hour because it was just like a much more practical source of news.

And then I was like, oh, then they'd put all the news in a podcast for an hour. I don't know where it dropped off in my routine, but it wasn't replaced by other news. So I guess maybe that's a good thing. But it was like a good, quick, felt like it didn't go into the fear mongering.

- The other thing is there's a lot of opinion and not a lot of fact in news these days because it's entertainment, because that's what drives clicks and that's what drives the business model. And that's challenging because like a lot of these, it seems like a lot of these news stories, they're changing minute to minute.

Like if you go look at the headline on one of their webpages when something happens, it's one thing. You go back an hour later and the headline and the entire spin on it has changed because some new information surfaced, whatever it was. And so it's actually hard to know at any point in time, like, okay, what am I getting?

Like, is this real or is this biased in some way? Has this been hit by like a bunch of filters and like hierarchies, whatever it is. It's hard to figure out like where can you actually count on the news source. - So maybe we'll close out and put this all in perspective with the death paradox.

- Oh. - Just to take like a hard turn. - We're gonna end on a really bright, shiny, sunny rainbows note. - I think it kind of is. - I agree. So memento mori is this idea of knowing your mortality. It originates from, I think the Roman empire where the returning conquering hero after a military campaign would be paraded through the cities with adoring fans, cheering for them in this like golden chariot.

And they would place a person behind the conquering hero, whispering in their ear, memento mori, which means like know your mortality. Remember that you are mortal. And the whole idea is that you have to know your death in order to live your life. The idea is like, if you aren't aware of your own mortality, you expose yourself to a terrible thing and to terrible life.

So I think about this a lot. You know, there's these calendars that have become this like very viral trend of like, it's 52 rows across, like squares across, and there's 80 squares down. And the whole idea is that you shade one in every single week and you can actually see your own life sort of like going into black as you shade them in across your life.

And for some people, that's really morbid. And for other people, it's really empowering to know that like every week matters. I mean, you can physically see the weeks going by in your life and that the weeks you're never going to get back, how precious time is with people. So it's something that I think about personally often, probably much more often now that I'm a father than before that.

But something that I think everyone should reconcile a bit more in their life. - Yeah, I mean, when you were talking about news, it's like, "Oh, do I want to cut out an hour here, here?" I think when you start to really put into perspective how much time you have on this earth, is it 40,000 weeks or 4,000?

- 4,000 weeks. - 4,000, I know, 40,000. - There's a great book, by the way. - Yeah, I don't know. - Oliver Berkman wrote "4,000 Weeks." - "4,000 Weeks." - It's an incredible book on all of this stuff. - Yeah, and it just makes me think, you know, "Die With Zero" was a, you know, they're all in the light of, we have this limited time, focus on how we use it, prioritize things that matter, don't let things that you don't care about fill your days.

I feel like with that perspective, you could go back and think about a lot of these paradoxes and figure out the best way to apply them so that you're living a life that's truest to what you want, which unfortunately seems to be, not seems to be, is the most common regret most people have at the end of their life, is not living life true to what they want.

- Yeah, not all time is created equal. I mean, you're like, you're in your 30s, I'm 32. This 10-year period relative to the 10-year period when I'm 80 is very, very different in terms of what I can do with my son, in terms of what I can do with my parents while they're still around, all of these different things.

And so if you just wait, if you delay all satisfaction, if you continue to say, like, play the deferred happiness game of, "Oh, well, when I get to this much money "or when I get this promotion "or when I get whatever it is, then I'll be happy," what you're gonna find is that you're gonna keep saying that until you die and until your kids are gone and they've moved off, they don't wanna hang out with you.

And until your parents are gone and you're not able to hang out with them or spend time with them anymore. And that's a terrible thing. And it's really, really sad when that happens to people. - Yeah, so I didn't mean to bring us to this place of thinking about death before the end, after we talk about the news, talking about death, but I think it's really valuable to put everything in perspective.

- I agree. - All right, I think, I mean, obviously, we'll put a link to the multiple paradoxes. I don't know how many there are in total 'cause you wrote one with 10, 15. - Eight million, I don't know. - One with 20, there were a lot, but I'll link to a few of them in the show notes.

We didn't get to all of them, but I think we hit on the ones that I was most excited to talk about. - Yeah, this was awesome. Really, really fun discussion. - Yeah, thanks for being here in person. - Love doing it. - Next time we'll have to do it in the sauna.

It'll be a different conversation. - We'll do sauna cold plunge and we'll see who can last longer in the cold plunge. - We'll see, I need some practice.