if you have enough smart friends talking about something, you should take it seriously. And again, a lot of these were for me, derived from bad experiences, where I didn't listen to this, and then I came to regret it. And so smart friends for me, I mean, again, going back to early COVID, all of these smart friends of mine were talking about board API club as a silly example, which maybe now it's not as much of a thing.

But at the time, it was like this, whatever, you know, NFT project, I didn't understand what NFTs were, but I had all these friends that were talking about it. And I was like, dude, that sounds stupid. I'm just going to ignore this. Like, that sounds super dumb. But I had multiple friends saying it over and over again.

And then like, you know, if I had listened to them, and done something about it, 12 months after that, I probably would have made like a million dollars off of just putting in a little bit of money into this thing. And so I developed a rule, basically, that was if three smart friends, like three friends that I consider intelligent, tell me about the same thing, I'm going to put like a little bit of skin into the game, no matter what, even if I'm not going to go deeper on it, it just like gives me kind of a hedge against looking like an idiot later on, like I did with that one.

Zile, thanks for being here. I'm so happy to be doing this in person. I know. I don't do a lot of these in person. We're here in New York City at Podstream, which I've never been to, but right in the center of Times Square, but we are in a dark room between two ferns, as it were.

Yeah, we are. So, so much of what you've written online for the past few years has had a big impact on me. And every time I come into a conversation, I'm like, oh, there's so much, but I got this advice from someone recently about travel. They said, whenever you go to travel, pretend like you're going to that city a million times for the rest of your life.

Just don't, don't feel like this is your last trip. So I'm gonna treat this conversation like it's not our last conversation on the show, so I don't have to cover everything. So I thought back to kind of the first content of yours that I'd read, and it was all about razors, which at the time I was like, I don't even know what that is.

And I felt like that would be a great place to start for this conversation, but like everyone else listening, I'm sure people don't know what razors are. So can you talk a little bit about what they even are and we can jump into why they're important? Yeah, absolutely. So it's not for shaving.

Yeah. Would be the first thing I would start with, I suppose. No, I mean, a philosophical razor, the term is from philosophy and basically the idea is that it's a rule of thumb or some sort of decision-making heuristic that allows you to cut through available options and make a decision.

So the whole idea was like in philosophy, you can take a razor and it allows you to like strip away any of the unnecessary things in order to cut through the noise and just make a decision. So Occam's razor is the one that if people know a single razor, Occam's razor is the thing they've heard of.

And that's like the whole idea that basically simple is beautiful. It's like if you have a whole bunch of hypotheses, the one that requires the fewest assumptions is generally the one that is right. If you're kind of like looking to decide which path you believe is the driver of some situation.

So I've written a bunch about razors and basically like extending the concept into a whole bunch of different realms. I think a lot about ways to simplify decision-making. It's always been something that I've liked. You're sort of similar to that, like life hacks, right? Are all sort of razors in their own way, shape or form, like ways to make a decision, cut through things, that'll just simplify your life, hopefully, like tools in your toolkit.

So that's been the kind of genesis of me writing about them in the past. Yeah, I think when it comes to my whole scope in life is like, how do I optimize everything? I think one of the challenges you get into is there's just too much and you get overwhelmed.

So for me, I love these idea of razors, rules of thumb to just make some of it a little easier. Although the risk is that you then have like a million razors, which would be the pushback against this, which is like, "Oh, I have a million razors. I can't remember a single one of them." So the way I always think about these things is like tools in your toolkit.

You don't need to like know that you have all of those different wrenches or all those different things at every single point in time. You just need to like have your toolkit and be able to open it up and think about, "Okay, what applies to a situation at any point in time?" Yeah, and I don't expect anyone listening to go home and be like, "I got 17 razors to use in my life." I did try to bulk them into a couple of categories because I thought that might be helpful for people to think, "Okay, I need to make a decision on this thing.

Is there something that might make this easier?" So the first one I thought about was related to people. There's people in your life. First one I had was the optimist razor, which I consider myself an optimist, so I like this one. Let's start there and kind of go through a few people one and see where we get.

Yeah. So the optimist razor is basically the idea that you should always default to trying to spend time with optimists. And if you have a choice between spending time with optimists and pessimists, you're always better off spending time with optimists. And the grounding of this, I mean, I originally came up with this during like the period of COVID when there was a whole ton of pessimism out there around like, "Oh, the markets are going to hell.

The economy is going to hell." And then there was like little shades of optimism and like kind of mid-2020 about, "Okay, but a lot of these things are happening X, Y, and Z that might be positive actually for the future." I mean, the Fed was printing trillions and trillions of dollars.

And what I found was my initial skew was to pessimism. And I was like, "Oh, short the market. Everything's going bad. Everything's going bad." And really regretted that after a few months when I realized that the optimists were actually the ones that were getting rich by betting on things going well in that time period.

And so, I started just thinking about, "Well, there's this little heuristic that pessimists sound really smart, but optimists seem to be getting really rich." And it all of a sudden cemented in my mind like, "Okay, there's something to this. And really, I want to be spending more time around optimists in general." But it's not just about investing and making money.

It can be just who you want to hang out with on the weekend. Totally. I mean, that's why it applies so broadly to life. And when I took it beyond that, I just started thinking, "Who do you feel good when you're around?" Just as a general rule of thumb.

You're like, "Who do I get energy from? Who makes me happy and feel good to be around?" And that tends to be optimists. Again, pessimists, they sound smart. They have a lot of things and negativity, et cetera. But being around people that are positive and optimistic about the future, about what it looks like in any arena, just tends to feel better.

And what I find is that good things happen when you spend time with optimists. They just have a better outlook on the future. And if you believe that energy attracts energy, optimists tend to attract good outcomes. Yeah. What about finding people to work with more than just hanging out?

Yeah. I mean, it applies to another kind of area that I've thought about, which is originally from Nassim Taleb, the author of Black Swan, who I don't know if... I forget what book it's in. It's either in... I don't think it's in Black Swan. It might be in Skin in the Game or Anti-Fragile, where he talks about this whole thing of the surgeon and how you pick a surgeon.

And so he tells this story of you choosing between two surgeons who are of equal merit. Assume they both have the same track record of successful surgery, say. And one of them looks like this beautiful, polished Harvard Medical School credentialed surgeon. Perfect, clean cut, everything's good. And then the other one looks like a butcher.

He's got blood all over him. He just doesn't look the part. He's big hands, whatever, big beard, scraggly. And his whole thing is that most people pick the nice, clean cut surgeon when what you should actually do is pick the one who doesn't look the part. And his logic is that the one who doesn't look the part has had to overcome not looking the part in order to get to where they are.

And so if they have equal merit, that one is actually the better one because they've had to overcome not looking like they should all along the way in order to get to that level. And I've always thought that was like another interesting way of thinking about who to work with, because we do have all of these little biases and prejudices that are in our head.

And people that have managed to overcome all of those all along the way to get to where they are tend to be great, great people to work with. - Yeah, I don't know if you've ever done unconscious bias training, but it just kind of like opens your eyes up to, "Oh, okay." Like even someone who might not think you have bias, you have bias for sure.

- Yeah, I mean, the statistics on those things are insane. Like you can go on Google and just like look one up and do one of the tests quickly and you can get like a score on it. It's usually pretty shocking. - Yeah. - What about smart friends? - Again, like with people, man, the smart friends one is basically that if you have enough smart friends talking about something, you should take it seriously.

And again, like a lot of these were for me derived from bad experiences, like where I didn't listen to this and then I came to regret it. And so like smart friends for me, I mean, again, going back to early COVID, like all of these smart friends of mine were talking about board API club as like a silly example, which maybe now it's like not as much of a thing, but at the time it was like this, you know, whatever, you know, NFT project.

I didn't understand what NFTs were, but I had all these friends that were talking about it. And I was like, dude, that sounds stupid. I'm just going to ignore this. Like, that sounds super dumb, but I had multiple friends saying it over and over again. And then like, you know, if I had listened to them and done something about it, 12 months after that, I probably would have made like a million dollars off of just putting in a little bit of money into this thing.

And so I developed a rule basically that was if three smart friends, like three friends that I consider intelligent, tell me about the same thing, I'm going to put like a little bit of skin into the game no matter what, even if I'm not going to go deeper on it, it just like gives me kind of a hedge against looking like an idiot later on, like I did with that one.

But again, it's just another way of thinking about, you know, drafting off of the intelligence of your peer group. Like if you have smart people that are talking about things and you're in these circles with intelligent people that have domain expertise that goes beyond yours, listening to them and taking it seriously when there's enough density in a single idea is usually a good bet.

Presumably they have to be excited about it or just talking about it. I think excited about it, you know, like, and again, and domain experts, right? Like not just like you don't want to have, you know, your like coder and engineer friends, maybe like weighing in on like culture and fashion and being like, oh, I'm going to listen to them.

Like you want it to be people like if they're in technology and they're weighing in on some new technology, like AI could be an example today. If you have a certain domain within AI that a bunch of your smart friends are really interested and excited about, it's worth taking seriously.

It doesn't mean you have to invest in it or do something, but it's worth at least digging into it and trying to understand more because it might be like an asymmetric bet on the future. - Right now, I feel like this about AI, except I just don't know how to make that asymmetric bet.

Or maybe it's not even asymmetric anymore because what is it like a hundred million people are using chat GPT at this point? - Is it really a hundred million people? - The growth curve on chat GPT, you can search it, or I'll find the link and put in the show notes.

It's like, you know, Instagram grew to a hundred million users this fast and all this, and you see these curves like this. And then chat GPT is just like a straight line up. I think I've seen that. I still just wonder with technology stuff like this, how much of it is that we're just in a bubble of sort of like semi-nerdy people on Twitter versus true mass proliferation of an idea.

I honestly just don't know. I think chat GPT is probably across the chasm, but I used to wonder that like with web three stuff, like if you go to like a normal person on the street, they're like, "What the hell is an NFT?" Right? And so like there clearly wasn't a mass proliferation of the idea.

The utility of chat GPT makes me believe that it is actually mass proliferating. - It's funny because I had this experience this morning. I flew to New York today and I'm waiting for my bag to go through the metal detector. And I hear three TSA agents talking about AI.

And they're like, "Yo, I use this thing and it creates song lyrics, it creates art." And I was like, "Okay." It's clearly crossed to the mainstream, but the use cases everyone's excited about are not necessarily use cases that I think will drive business. The challenge I have is it's something that I feel really passionate about being big and have no clue how to bet on.

And there was a pretty good episode of the All In podcast where they were debating how to invest in this space. And these are some of the smartest investors in the world. And I can't remember which one said, "I still haven't invested." Because if you look at the early days of so many of these industries, even look at social, the first few social networks actually didn't work out.

And so I'm frustrated because I feel like there's a there there, but I don't actually know what to do about it. You also have to separate it. If you're going to invest, you also have to separate it from hype cycle. Normally, TSA agents talking about it, I would say is really peak hype cycle of something.

And so hype cycle drives valuations. And so if you're looking... I have this fund where I invest in early stage companies. And if you were to look at the average deal that says they're an AI company right now, the valuation at pre-seed or seed is like $25, $30 million, which is very, very hard to drive a return in the aggregate across an asset class.

And so that's what I struggle with. They're benefiting from hype cycle on their early valuation, which hurts investors on the margin. And so it's tough. It's tough to discern, "Okay, what's there? What's actually just going to get eaten by whatever big company decides to do this?" It's tricky. And most of them, by the way, are just doing an open AI API call.

They don't actually have anything internally or proprietary about it. And so again, it's like, "Okay, you're just linking to another person's platform." Yeah. The number of companies that have pitched me a thing that's like, "Hey, we take a document and we give you answers on it." And I'm like, "There's literally...

You're just monetizing this other API." With your own UI/UX. Although a lot of companies have been built in that general way in different areas where it's just like, "Oh, we link to whatever platform we're using their backend." So I'm not saying that company can't make money. I'm just skeptical in investing in anything at these valuations.

Totally. Totally. But to come back to Razors, what do you do when someone comes to you with a crazy idea? Oh, man. So my favorite thing around crazy ideas is... I think it was Paul Graham. Yes. Paul Graham, the famous investor, he didn't actually frame it as a Razor.

I turned it into a Razor, but he wrote this piece on what to do if someone comes to you with a crazy idea. And basically, his thing boiled down to two questions to ask yourself, "Are they a domain expert? And do I know them to be a reasonable person?" And if the answer to both of those things is yes, then you should probably take the idea seriously because it might be an asymmetric bet on the future.

And I thought that was such an elegant way to think about this because it's very easy to write off crazy ideas. You hear something and you're like, "You don't understand this." You're just like, "That sounds ridiculous. That seems ludicrous that that would ever happen or that the future would look like that." But if you slow down and you ask yourself those two questions, you can actually totally deconstruct the entire problem.

You're asking, "Are they a domain expert? So do they understand this thing that they're talking about, the area around this thing very, very well?" If the answer is yes, move on to the next question, which is, "Are they a reasonable person or are they completely ridiculous?" And if you know they're completely ridiculous, you're like, "Okay, maybe I'm going to hesitate a little bit." But if they're not, if you know that they're a reasonable person and that they do reasonable things, now you start to take the whole thing seriously a little bit based on those two.

So I've always thought that that was a really, really good way to cut through the noise on it. Yeah. I find that my instinct is often to be like, "That's not right." Totally. I think that's most of our common instinct when we hear anything. Especially because I don't understand it.

I'm not technical enough to know on most of these things. And so when someone says something that sounds crazy to me about the future, what the future is going to look like, what people are going to be doing, my default is like, "That's stupid. No, no way." And generally, on five or 10-year time horizons, anything I thought was stupid, I've been completely wrong about.

If there were enough people talking about eSports, people filling... Someone said this to me in, I don't know, it's probably 2009. When I got to college, someone was like, "Dude, eSports is going to be the next big thing. People are going to fill stadiums watching people play video games." And I was like, "You are an idiot.

I'm not listening to you anymore. That was dumb." And again, if I had bet on that in some way, that would have turned out pretty well for me at the time. And so now my new default is like, I take anything any smart person says, at least remotely seriously.

It's like I had one of my razors was around listening. And the whole idea was like, if someone says something that is very different from your beliefs, you should listen twice as much as you speak. And that applies to this type of thing with new investment ideas or ideas on what the future of technology looks like, just as much as political debates or anything that you're trying to educate yourself on.

Because generally, our bias when we hear something that we don't agree with becomes, "Okay, I'm just going to talk over them and I'm going to tell them why they're wrong about this thing." But if you flip the script on that and you say, "I'm actually just going to listen to a whole bunch and at least hear them out," usually you end up learning something.

Even if you don't agree with them at the end, that's fine, but you end up learning something from how they're thinking about it. Well, also, I think one of your life hacks, so Silas' great PDF of 50 life hacks, if I remember right, is trying to be interested, not interesting.

Yeah. Yeah. I mean, this is like a simple reframe. Especially when you're young, I definitely fell into this trap when I first started my career. My whole thing was like, "Okay, if I'm going to go to an event and I'm going to talk to people, I really want to be interesting.

I want to talk about all the interesting things I'm doing or the interesting things." The challenge is you're actually just not that interesting at age 22. I mean, on the margin, most people are not that interesting at 22. At 25, frankly, most people aren't interesting for the first 10 years of their career because you just haven't done enough.

There's not enough experiences in your life. My whole reframe around it is focus on being interested rather than interesting. Being interested means you're listening to people. It means you're asking follow-up questions. You're diving down the rabbit hole with them to learn more about why they think certain things or why they're interested in certain things.

When you do that, people want you around because interested people are really fun to be around because they're actually listening to you and they're actually asking follow-up questions. Most people at a cocktail event or at a party or whatever are just waiting for their turn to speak. You're talking to someone, having a conversation, and you see them sitting there and they're just like, "Mm-hmm, mm-hmm, mm-hmm." Then as soon as you get done, they're like, "Ah," they jump in with their thing.

That's not a particularly fun conversation part. I just think it's a great way to stand out in conversations and to actually learn things when you're in them. It doesn't even have to be if you don't have anything interesting. It could just be to build more relationships. Totally. I just think it's a good way to live life in general.

You end up learning so much interesting stuff by just being interested. Paradoxically, being interested is how you become interesting because then you end up getting into those cool situations. You end up learning interesting things. That's what you end up going and capitalizing on, working on, etc. How do you start that conversation?

I think there was another life hack by just how to start the conversation to build it. I just found meetings or situations where I was way over my skis early in my career. I've always just been great about finding my way into weird situations that I don't belong in.

Even this last weekend, I was at the Berkshire Hathaway annual meeting and I had a chance to talk to Bill Gates. In a situation like that, you're like, "What am I possibly going to have to offer or talk to Bill Gates about? I don't have anything possibly interesting that he would find interesting, given who he has access to." What I found is that the best way to get someone like that talking in what would otherwise be a weird, clumsy, awkward situation is to ask them what they are most excited about in their life right now.

That can be personal or professional. They can take it however they want it. Normally, really successful people have something that they're fired up about at any point in time. If you can get them talking about that, then it becomes really easy. The pressure's off you. They're excited. They're energetic about whatever it is that they're telling you about.

Then you can just ask follow-up questions. You can just dig deeper on stuff, again, to being interested. That becomes a much, much easier conversation with anyone. So, what was Bill Gates interested in? What was Bill Gates excited about? I actually don't know that I'm allowed to talk about the thing that he was excited about in public because it was in a private setting.

I actually don't want to share it. Okay, but it was a fun conversation. I mean, short, fun conversation. You get someone that otherwise you would be like, "Hi," to talk for five minutes. That's an amazing experience and opportunity. It was generally around climate technology, something that he's working on.

I think it'll be public. I think it is public, maybe, but I just don't want to. It's funny. I talked to Catherine Minchu, who runs this company called The Muse, based in New York. Her power move in situations like this, also, when you're talking to someone that's more senior than you, chances are that person is like, "When is this going to end?" Yes, you can make them excited.

She tries to be the one that always ends it first. She's like, "Oh, I'm going to remember that person. I could talk to them again because they didn't just sit here and dominate my time." Oh, that's interesting. She brought up a time where she was at some conference, and she was talking to Elon, and in the middle of it, she's like, "Hey, you know what?

I got to go. It was really great to talk to you," and just walked away. That is a power move. And she said it's made people that otherwise would be like, "When is this person going to leave this conference?" It just made it so much better. Yeah, and it makes it less awkward for them to have to end it, too, when you just do it.

I also find, by the way, that following up and sending someone a book is one of the best life hacks in the world because all of these hyper, hyper successful people get sent so many fancy bottles of wine, expensive champagnes, expensive bottles of alcohol, super nice gifts that you couldn't possibly spend enough money to send them something that would stand out.

But if you send someone a book that really mattered to you with a handwritten note on personalized stationery of why you think it'll resonate with them and something from the conversation that you enjoyed, you'll always stand out in their mind forever. They'll remember that because no one really does that.

It's just an old-fashioned thing. So, it's a great, great way to stand out with people. Is there a book you've gifted the most? Yeah, One Breath Becomes Air, by far. Probably 95% of the time, that's the book I share with people. If you've never read it, it's unbelievable. I know.

I haven't read it. I'm like, "Oh, man." Oh, you haven't? No. Oh, my God. Well, it'll knock you out. I read it on a plane for the first time, and the last piece of it, I was full-on crying on this flight, and the woman next to me had to ask if I was okay.

So, don't read it in a situation where you're not comfortable crying. Okay. So, to wrap up all of these people-related razors, I want to talk briefly about Henlon's Razor. Never attribute to malice what could otherwise be attributed to stupidity, is the way that that is typically put. So, basically, the idea is if someone does something, we have this tendency to say, "Wow, they're acting maliciously.

They're acting negatively towards me or towards other people, whatever." And we should never do that if stupidity is a potential argument. So, it's like the whole idea that we give people too much credit for being malicious actors, when in reality, they might just be ignorant or dumb or unintelligent, etc.

This is a great one for Twitter. In general, you read people sending mean comments or saying things, and you're like, "Oh, they're acting so maliciously, and they're acting in such a bad-faith way," when sometimes you can just chalk it up to them being ignorant or stupid. Is this similar to assume best intent or in the ballpark?

Because I feel like that's one I use a lot. Yeah. I'd say it's similar. Maybe, yeah. Assume best intent is probably a nicer way of saying this. I just always found Hanlon's razor to be really funny because it's just like, if you are finding that you're thinking someone is acting in some bad, nefarious, calculating way, sometimes it's just that they're just not intelligent.

Okay. So, I think we covered a bunch of... You've written multiple posts with lots of razors in lots of forms. I tried to pull some from the old posts, some from the new posts, and that was a lot of things related to interactions with people. I'll link to those posts in the show notes.

What I like is that, in a lot of those posts, you say, "Hey, use this when you're deciding who to hang out with. Use this when." We can link there if you want to recap from this conversation. The other area that you alluded to at the beginning is making decisions, which I think is something that, when optimized, can really save you time because I know myself and a lot of people listening spend a lot of time making decisions, trying to get to the optimal outcome.

So, let's talk about a few of these decision-making ones. Let's start with the arena. The arena. This all comes from the man in the arena, Teddy Roosevelt's speech of, "It's the person in the arena that really counts." And my whole operating principle around this is that you should always try to put yourself in the arena.

And that takes on different forms in different areas of life, but basically, don't sit on the sidelines and sling rocks at people that are out there doing things. And so, if you have a choice of two paths of how to operate, you should put yourself in the vulnerable position in the arena because that's where you end up having the high upside things happen.

That's where real growth occurs and where you end up having those wins, et cetera. You can't really win long-term by sitting on the sidelines, especially not sitting on the sidelines throwing rocks at people that are out there. And you said this is the one you feel the most strong about in one of these posts.

Yeah. Have you seen a lot of personal wins from playing this? Yeah. I mean, I think that it's the most wins, but it's also the most, I don't know, emotionally draining and trying sometimes because by putting yourself in the arena, you're exposing yourself to the whole lot of people out there that do just want to sling rocks from the sidelines.

I mean, you've seen it, right? We're sitting here, you're producing this podcast. You've been creating this for a long time. You share everything publicly. It's out and about. There are going to be people that don't like it, that criticize it, et cetera. That's not fun because you're like me.

You're a very positive, optimistic person. You're happy. You generally are just a good, positive guy. And when there's random people out there that are reading your stuff or engaging with your stuff and are like, "I hate Chris. He's awful. What a bad person," et cetera, it's a weird feeling where someone doesn't know you and they're engaging that way, but you've gotten so much upside from putting yourself in the arena and just consistently putting things out there.

So I think it's like you have to be able to have thick skin and take it when you're going to be putting yourself in the arena, but that's where the real wins actually end up happening. So for me, with my platform, with anything I'm putting out there, you're constantly putting your neck on the line and exposing yourself to it.

And when you're sharing ideas publicly, that's a very vulnerable state to put yourself in. The same thing applies to working in a corporate job. If you're going to put your ideas on the line with your boss or with your team or however you're going to do it, again, it's very easy to just sit back and let other people do that, but that's not how you're going to end up progressing and making it to the next level of whatever you want to do.

Any tips for how you take that negative feedback? I feel like I'm fortunate because I don't love that podcasts are such a one-way medium that I don't hear. It's so much more effort to be like, "Oh, I was listening to something cool. Now I'm going to go find that person's contacts, send them a note." So I tend to get pretty positive feedback because it's people that were pretty excited about what happened and sent an email and I replied to them.

I know you replied to a lot of, if not all the emails you get. But a friend of mine posted on the close Instagram thing this morning. She posted something online. She's like, "I'm just having a bad day." And she posted a picture of Ben and Jerry's. "I'm having ice cream." And she posted photos on her close friends of all the DMs she got.

And people are like, "I can't believe you would promote a brand like that." Or like, "Can't you eat healthier ice cream?" And I was just like, the internet can be a mean place, especially social media, which I don't spend a lot of time on as much as I do recording.

But I know a lot of people have probably faced this, whether it's at work, throwing out a bad idea. How do you take that? Because I'm sure you've gotten a lot. I think defaulting to empathy is the single healthiest and best way that I've found to combat negativity. Basically, when someone says something super negative on the internet to someone that they don't know, it's pretty fair to assume that that person is not in a happy place in their life.

Like happy people... Have you seen Legally Blonde? This is going to be an embarrassing reference. In the movie Legally Blonde, she's like, "Happy people just don't kill their husbands. They just don't." And I think about that with happy people on the internet. Happy people just don't comment mean things to other people's posts on the internet.

They just don't. It's just not a thing that you would think to do. You're a happy guy. I don't think you would think to go and attack someone that you don't know on the internet. It's just not a thing you would do. And so, I tend to think that when someone attacks you with negativity, there's usually something that's going on in their life that's tough.

And we don't know what that is, and we're not behind that person's eyes. And so, I try to default to empathy when I read something like that, of just like, "Oh, that person's having a tough day." Or the person is in a tough spot for whatever reason, and not get all wound up about it.

I never engage or fight back on that kind of stuff. Because again, it's like, I'm not going to convince them they're wrong. I'm not going to make their life better or change it. And so, there's no point. Back to some of the career stuff. What about when you're faced with trying to decide between two paths you could take at work?

So, this is one from Naval that I really like, where he talks about making uphill decisions, I think is the way that he phrases it. Which is basically when you choose between two paths, you should choose the path that is harder in the short term, because those tend to be the paths that work out better in the long term.

So, it's like the whole short phrase of hard choices now, easy choices later, easy choices now, hard choices later. And I think it's an interesting, although nuanced one, to be totally honest, as I've thought more about this one over time, because sometimes choosing the hard path means that you're not allowing yourself the time to think about whether there's an easier way to do it.

Like Tim Ferriss, who I know we both really like his work, talks about often, what if this were easy? What would this look like if this were easy? And I think it's a really important question to constantly ask yourself, is there actually an easy mode that I can play this game on that I'm just ignoring because I'm taking pride in doing it the hard way?

And as someone who's sort of a recovering hustle culture bro from back in the day in finance, I often missed the easy mode way of playing the game because I was so prideful about playing the hard way. And so, I think this uphill decision one is actually a nuanced one I need to think about more and that people should think about more of anytime you're doing something and it feels hard and difficult, you should pause and ask yourself, is there actually an easy mode?

Is there an easy way that I can do this that I'm just missing out on because I'm grinding away in the way that I am? - Yeah, and I sometimes think there's both easy and I sometimes think that gets caught up in cheaper, especially in a world of trying to optimize your life and your money and you're like, oh, well, this is the cheapest way, so I should do it this way.

- Give me an example of that. - So my wife and I, I've just talked about this on another episode, I don't know if it will have aired at this point, but my wife and I are talking about our children and we have a daughter who's about to be three, you'll learn this in a couple of years and she had this stint where she would just get out of bed after going to bed.

She'd say, run out the door, open the door and say, I have to go to the bathroom. Okay, I need a stuffed animal. She would just get out of bed constantly and my wife and I are like, okay, what do you do? You go on the internet and there's a bajillion people who have an opinion about what to do and it's hard to figure out what the right thing is.

So it's like, what's your manifesto? Who do I trust? And when it came to a lot of early decision stuff, we just went to Emily Oster, who's written a few books about parenting and she's like, this is what you need to know about the expecting phase, the baby phase, but I didn't have something from her for this.

And my wife was like, well, I really like the content that this company called Big Little Feelings puts out. And I believe we use their course for potty training. And it was like, instead of reading 10 books, my wife's just like, I really like how they teach what they believe in.

So she took their course, it was 30 bucks or something. She's like, we have this other course, it's $100. And she was like, do you think it's worth spending $100 to get a source I really trust database of how to handle every toddler scenario? And I was like, well, what's the alternative?

So what we did was we were like, well, one alternative. So I just asked ChatGPT, I was like, what should I do? Answer was like, okay, it's surprisingly good. But it's like, do we want to go do a bunch of research or just trust this thing? And so a part of my mind was spinning saying, well, I could go find the answer.

The answer exists on the internet, it's all this work and it's the cheaper one. So I was both taking this uphill battle of the hard work of me deciding what the right answer is, but also the cheaper answer. But my wife asked me, and this time she was in this situation I usually am, which is like, she's saying I want to do all the work.

And what I learned is it was really easy for me to make a different decision when it wasn't for me. And when I put a little bit of emotion in it, I was like, just buy the thing. No problem. It was an easy decision for me, but for her, it felt so hard because she was like, well, I could do this research, could do it.

Maybe I'd learn more. So cheap is not always cheap. The thing I've always found is that the thing I think is cheaper is generally more expensive. And I find this with everything. I've always been a big, this is me not being frugal too, but I've always been big on just like, my wife would ask, we were getting our new house here in New York and she's like, what furniture?

There's this furniture or there's this furniture. And I was like, just get the nice one because you're going to have it. And getting the cheap furniture sounds good when you get it and it's 50% cheaper, but when it breaks and you need to get new, we got cheap outdoor furniture and really nice indoor furniture.

Well, the outdoor furniture after one winter in New York now looks like crap and I'm going to have to buy new outdoor furniture. Now I'm going to have to get the nice outdoor furniture so this doesn't happen again because I don't want to replace it every year. Would have been better off just getting the nice one and taking care of it and doing that.

And so I've generally found that the thing that is like the cheap way of doing it, like spending tons of time on chat, GPT, researching all this stuff. Well, now I have the headache of having to like synthesize all of this stuff that I've found and convince my wife.

Cause it's like what I found and she didn't find it. And I just would have been better off buying the course and spending whatever it costs because it would have saved me so much time and so much stress. Yeah. So nothing makes me happier. And you are an example of this, of finding someone who's done all the research to come up with a bunch of, I'm not going to go research what my razors should be.

I'm just going to take your list of razors and be like, I'm going to use this. That's how I feel about hacks with you. Yeah. So that's my, my, my gift is, uh, optimizing life. Yours is synthesizing. I guess it's kind of a similar thing. It's, you know, you've got business advice, personal advice.

It's a different advice, just maybe not as focused on deals and travel and optimization. But when it comes to decisions, there was another one about rare opportunity. So I learned this one, this is an interesting one. Cause I heard this for the first time from the founders. Let's see the two of the three partners at the first firm that I worked at.

And basically they were two younger guys who spun out from their prior firm with one of the founders of that prior firm to start a new one. And they were like 30 when they spun out and got to be co-founders of this new private equity fund. And I asked them how they thought about that decision.

And the way that he said it was there are certain opportunities in life that you get on average zero to one time in your life. Like the average person gets zero to one. And so if you get, if you're one of the lucky people that gets that one chance, that one opportunity for this really rare opportunity, you have to jump at it.

And he was like, starting your own private equity fund is an opportunity that you get zero to one times in your life. And so the fact that he was getting it, he was like, I have to go do this. Even though he was on the safe track doing really well at his prior firm.

And I remember registering that as very, very interesting. And then when I was thinking about my own opportunity to go and kind of build this ecosystem and the thing that I was working on, it was a really key factor in me deciding to kind of go all in and do it because I felt like, okay, I might get one chance to do this unique thing while I'm on a growth curve and things are going well.

And there's all this stuff happening in the world. Like this might be my one chance to go do the interesting thing. Because if I don't, then I'm going to have like all this gravity around what I've been doing and it's going to have built and we're going to have kids and it's going to be much more challenging.

And so here's my like rare opportunity that has popped up and I need to just jump at it. And I think it is like a really good framework for thinking about those unique moments in life. Just like being able to pause, recognize when you're in that, like you're having that unique chance and to just sort of throw caution to the wind and jump at it.

Yeah. And I think not overthinking the reasons not to do it. So I look back, I was in college and I won't go into the whole life story, but I didn't know what I wanted to do. I didn't even really realize that you were supposed to plan your job so far in advance.

So I was like springing at the end, like I got to go get a job. I got to do this quickly. And I got an opportunity to work at an investment bank in New York called Allen & Company. Kind of like weird, small boutique bank. I knew it. But the only job they offered was an internship.

And I was talking to friends that actually knew, like at the time I was like one month into even knowing what investment bank was. And I only went down that path because I asked my friends who were well more prepared and said, "What's the best job you can get out of college in American investment banking?" I was like, "Well, I guess I should do that.

I don't know what I want to do." And they were like, "Allen & Company is like a very, it's not like one of the places you could just get a job." It was like, kind of had this mystique and allure. And I was like, "Do I take an internship at a company?" Not a full-time job, just an internship and see where it goes.

But everyone was telling me like, "This is a rare opportunity. You don't usually get an offer from a company that's so secretive and cool." Especially when you don't know what investment banking is. Yeah. I mean, I had read my vault guide. I don't know if the vault guide still exists, but back then it was like, there was this book.

It's like, "Read this and you understand the industry." So I took that. That was one. I feel like starting a podcast was one. There've been a handful of times where I've quit a job to go do a thing, or I don't know, we traveled around the world because we were like, "This is a window to do it." So I love that one.

Yeah. It's just taking advantage. There was a Razor you had about regret minimization, and I'm curious, it didn't make it to your new list related to Bezos, not Gates, so sorry. But I'm curious if that's still something you think about. Yeah. I mean, the regret minimization framework, I think the first time Bezos talked about this was in an interview with Walter Isaacson.

It might be like 1996, way, way back interview. Basically, we're super nerdy Bezos, not jacked out of his mind Bezos that we have today. Really nerdy Bezos is talking about how he made the decision to leave D.E. Shaw. This relates directly to the rare opportunity, by the way. Leave D.E.

Shaw, which is this famous quant hedge fund where he was making tons of money, and on a very certain path to make tens of millions of dollars in his life. Amazing, amazing outcome in career, top 0.01% life. Leave that to go start a bookstore on the internet, which makes no sense.

Again, crazy ideas going back to connect it to other Razors. His whole thing was zoom forward to the future. Think about your 80-year-old self looking back on this decision. Will you regret not doing it? If the answer is yes, then you should do it. That's what he did. He thought, "Well, I regret not taking this opportunity and going after this." The answer was yes, and so he left and started an Amazon, and now we all get packages in 24 hours from drones that are dropping them off.

I think it's a brilliant general way of thinking about this. I've often thought about it as in both directions. You're like, "Okay, what would your 80-year-old self say about this decision? Also, what would your 10-year-old self say about this decision?" The reason I think that one's good is because your 80-year-old self really cares about the compounding of the decisions you make today and how any decision you're making today is going to compound into the future, but your 10-year-old self also reminds you to not take shit too seriously along the way.

You're probably like this too. You're an optimizer. You're thinking through every decision. You're really thoughtful. You're constantly trying to get little bits of ROI out of everything you're doing. That's great. I think there's a lot of value that can be gleaned from that. At the same time, sometimes you just need to have some fun and not think about razors and not think about hacks and just go have a beer and sit on the couch and not take advantage of whatever time you're wasting by doing that.

I think that that always helps. I call it the young and old test. It's like you think about the decision as a 10-year-old and as an 80-year-old and then meet in the middle. The Bezos thing, it ties directly to the rare opportunity. You have this one potential opportunity in your whole life to go do this thing and you should capitalize on it.

To your point on making these decisions without thinking too much about them, I've often thought about that as a concept, which is big decisions, paradoxically, I find are better made quickly versus slowly. There's this desire when you have a big, big decision, you're like, "Okay, I'm going to sit down and make this big chart of pros and cons and spend all this time thinking through them." What I tend to find is that your instinct actually is usually pretty good.

Sometimes you just need to open the door, jump out and hope you packed your parachute really well. I think it ends up making for much better outcomes. You don't waste so much time. I did an episode recently, I haven't aired it yet, where I had a performance coach come in and we picked a topic and we just recorded the session.

The topic was I struggle so often of over optimizations. I have all these decisions to make. What he actually broke down through this interesting conversation using tactics that we later in the episode talked about the tactics he was using, was that a lot of times most decisions are made emotionally, but you don't think that in the moment.

You might be talking about big decisions, you want to make your pro and con list, analyze everything. He's like, "You need to stop and not just reflect, but maybe get outside and force yourself into a different state because the emotional decision might actually be the easy way." He was basically trying to teach me that this thing that we often think of as our gut decision might actually be more of an emotional decision.

We talked about this exact example I used about my wife in this course. He was like, "It was so easy for you to make that decision because you were thinking about it emotionally. You weren't in the middle of doing the research." My new thing is whenever I'm in the middle of trying to make a decision, big or small, I try to pause and then get myself out of the research phase.

Not pause and look at my options, pause and look at my spreadsheet, but pause and go outside for 10 minutes and just think about what's the right decision here. Sometimes it just comes to you. It doesn't come to you when you're looking at the data. It comes to you when you think, "What would the right decision here be?" It's interesting.

My reflection is just I've never made a single pro-con list that actually swayed my decision. I've never drawn... In a movie, they make the pro-con list and then they look at the list and the pros are like, "There's 30 of them," and the cons, there's three. You're like, "Oh, okay.

It's clearly a pro," but that's never happened to me in real life. What ends up happening is I just sit there and stare at something that looks relatively balanced, and then you just end up making the decision anyway. It's not like it actually helped me think it through. I don't know.

I go back and forth. I'm like you. I have all these frameworks and mental models and razors, but it's not like I'm sitting going through a checklist of them when I'm going and making decisions. It's again, things that are in your mental toolkit that you're generally thinking about. To go back to one, the optimist razor, it's not like I'm thinking like, "Okay, well, Chris invited me to do a podcast and Chris is an optimist, so I should...

Okay, by this decision-making, I'm going to go spend time with Chris." It's just ways to live your life that you just generally are trying to be around optimists or whatever it is. I try to avoid being mechanical about how all this stuff gets implemented. It's just general rules and ideas that you have floating around your brain that you're applying to how you live life on a daily basis.

Yeah, I really like that. I was thinking maybe you had the contacts sorted by optimist score. Yeah, yeah, yeah. Optimist score, Chris, 7.2. Okay, we're doing the podcast. Okay, so we're not going to spend all of our time optimizing every decision we make, going through these rubrics every time we do anything.

Let's talk a little bit about how we spend our time and how we choose what to do with our time. One of the things I know you value is serendipity. Yeah, I have this concept of luck surface area that I've probably adapted from people that have talked about it over a period of time.

The first time I ever heard serendipity, I think it was serendipity, I forget what he called it, was this guy, Tim Brown, who was the CEO of IDEO, the big design firm. He talked about the whole idea of engineered serendipity, that you could create luck. It was the first time I had ever heard of it.

This was probably back in 2010 or something like that. I was in college. It always stuck with me. I've recently been thinking about luck surface area, the whole idea that you can actually expand your surface area for having lucky things happen to you. How you do that is by, again, putting yourself out there.

It's like, you don't get lucky sitting on the couch watching Netflix at home. You get lucky by being out, engaging with people, meeting new people, publishing your work, putting things out there into the world and seeing what can bounce off of it and the connections that can be made.

My whole idea with the luck razor or with the serendipity razor is you should always try to expand your luck surface area. If you're going to choose two paths, a decision to make between staying in and watching Netflix on a given evening or going to that opportunity, the dinner, the meeting, the people, whatever it is, or to publish something publicly rather than to just have it sit in your journal, you should take the path that has the larger luck surface area.

I think this applies mostly when you're trying to expand your luck surface area earlier in your life and in your career. Once you've done that, you've figured out where the ripest opportunities are, then you can start going deep and you can narrow it. For instance, today, I would probably choose to sit at home and relax and spend time with my wife and son rather than going out and about to some big event because I don't really feel like I'm trying to get lucky on things anymore.

I've sort of figured out where my luck has come from, and now I'm just going down and digging deeper into that area, into that hole. Early on, expanding your luck surface area in any way, shape, or form early in your life and career, I think is important. I want to come back to how we do spend our time.

Let's say you are going out and I'm going to tee up one other razor, which is there's two rooms. How do you pick which one to go to? The one where you're going to be the dumbest one in the room. Always, always. This is a common thing that people say.

If you're the smartest person in the room, you're in the wrong room. I really do believe that. Putting yourself in uncomfortable positions where everyone is smarter than you tends to lead to really interesting things, especially when you pair it with some of the stuff we talked about earlier, like good ways to get those kind of people talking, good ways to think about how you can be valuable to them, how you can stick out in their minds, walking away from the conversation.

Like you said, I like that one a lot. I'm going to steal that. Sending people books, etc. Just getting into rooms where you feel a little bit uncomfortable, that's where you end up having the most growth come. Yeah. I love just walking up to a table of people. I'm like, "I have no idea what you're talking about.

Let me just listen." It's super uncomfortable. Yeah, it is super uncomfortable. And you could do it in a weird way. But in the right environment, I think it's wildly interesting. Yeah. I'm going to this event in Santa Barbara in a couple of weeks. And there's a lot of wildly successful people that it looks like are going to be there.

And I literally don't know a single person. And today, I was like, "Man, it's going to be really hard to go and do this." Because I don't even have a wingman. I don't have a friend who's my guy that I can go around with or girl that I can go around with.

I literally don't know anyone. And I feel like a total imposter going to this event. Because everyone is... CEOs are really, really impressive people. And I had to snap myself out of it and just say, "Oh, what a cool opportunity to just be in this room." You can just go listen to people and add value in some other way other than talking.

So I'm excited for it now. What's your networking move when you're at an event like this? And you're like, "I don't know about you." Even though I love being around people, I get energy from people. I think my default is like, "Well, should I just go stand around here and check an email?" Even for someone who loves people, it can be a lot to just walk up to random people all day.

Yeah. I try to find circles of people. I think I tend to just walk and push myself into a circle and listen a little bit to what people are saying. And then I honestly use that question a lot. "What's getting you excited these days?" I've been asking people, "What lights you up?" Because oftentimes, people will talk about their kids.

They'll talk about their family. You end up getting to a more personal level than the same questions they constantly get asked. Like the CEO of United or something, an airline is going to be there. They probably constantly get asked about things about their business. Analysts are asking them those questions.

Earnings are... All this random stuff. But if you ask them about their family or like, "Do you have any kids? What are you getting excited about?" It just opens the door to a much more interesting connection that you can make with those kinds of people. And then you become interesting to the whole circle of people because you're the one that's driving those things forward.

Because at the end of the day, everyone feels awkward in those things. I don't know a single person that goes to a big networking gala dinner or whatever and walks in and is like, "Oh, I feel great. This is amazing. This is my favorite thing in the world." Those things suck.

Nobody likes that. And it's the reason most people end up drinking at those things is to loosen up a little bit. So I just think having a go-to move of how you insert yourself and talk to people. And honestly, just not caring if you feel a little embarrassed. Yeah.

Earlier in my career, I learned something. I wish I remembered who it was from. But most of these events, especially when not everyone's the CEO and it's obvious what they do, the opener question is always like, "Oh, what do you do?" And I picked up from someone the idea of just opening with, "What's your story?" I don't know if I like it more than asking what someone's excited about right now, because then you get more energy.

But if you're sitting at an event, you're trying to figure out, "Well, who are these people?" Because maybe you are trying to do some networking. You're trying to figure out who you need to spend your time with. What's your story is just a much better opener, especially when you're around people that maybe are in between jobs and it's super awkward to be like, "What do you do?" It's like, "Well, I don't have a job right now." Yeah.

And if you know them, if they are someone that everybody knows, and you know what their story is, and they know that everybody knows them, I've always found that just telling someone that you admire something that they've done is a great, great opener. No one is immune to flattery.

And people love to know that people have recognized things that they've done. Bill Gates, when I first said hello to him, I just told him I admired his philanthropic work in the developing world, because I really do. I've seen a lot of impact from it. My family's from India, and they do a lot of work there.

And that's not something that he typically gets told, probably. It's all about Microsoft, or all about being a mega billionaire, or whatever it is. And so, it jumps out immediately. And no one will look at you and be like, "Shut up," when you say something nice to them about things that they've done.

So, I also just find that that's a nice little way to get an entry point to a conversation. And while I don't think that the best thing to do is try to be the person who's jumping in and talking all the time, we already covered that. I will say, if you can find a question to ask someone about what they're excited about in that realm, but that ties into something that you have some unique expertise in, or I think we all probably know the topic that maybe lights up the room when you talk about, I wouldn't try to just jump in and have that.

But if you could steer the conversation towards a place where something that you're uniquely knowledgeable about. So, it just made me- Hey, were you guys talking about Twitter threads? Were you guys just talking about Twitter threads? Well, for me, this idea came to me when you're like, "What are you excited about?" I was like, "Oh, are you taking any exciting trips this year?" Almost everyone has a trip in the next 12 months.

It's like, I could steer the conversation towards something related to travel. That would be something where I'd be like, "I probably have some interesting hacks or tips to the average audience." But in a way that gets them to take it there in a way that they're excited about. That's a very good idea.

It's like shepherding them. You're like the river god guiding them. I like that a lot. That's smart. But I want to come back finally to where we spend our time. And you have a Time Billionaire Razor, but you actually did a really great post about this and looked at some data on how we spend time.

So, maybe let's end talking about how we spend our time and how that's evolved for you. Yeah. I mean, this is a topic that's very near and dear to my heart. You have young kids. I guess by the time this comes out, he will be one. And I have thought about time more in the last year than I had in my entire life.

Part of that is because when you have a young kid, you all of a sudden start measuring time in weeks and months, which you never really do otherwise. People ask you how old the kid is and you say like six weeks or nine weeks or 12 weeks, whatever. I've never thought about the passage of weeks as a passage of time.

In the past, it's just like another week. A lot of people have now seen that life calendar, like Memento Mori calendar, where it's 52 rows across and it's 80 rows down. So, it represents your entire life. Every row is a year and the 80 rows is your life and you fill in black every week that goes by.

So, you can literally see the passage of your life, passage of time. So, I've been thinking about this stuff more and more over the course of the last year. And I came across this American Time Use Survey data set that I think it was Our World and Data kind of crunched together to look at how we spend time over the course of our lives and specifically who we spend it with.

And I saw it, they had kind of combined it into a single chart of all these lines, like how much time you spend with your children, how much time you spend with your parents, how much time you spend with friends, coworkers, alone, etc. I went in and downloaded the data and split it out into individual charts that you could really see like each line and kind of the curvature of each line.

And it was an unbelievably powerful image when you look at them individually because you really get a feel for like, especially with kids, how you basically spend all of your time with them during this very short window of their life and then it falls off a cliff. And the reverse of that is with your parents, you spend almost all of your time with them over the first 18 years of your life and then it just goes like this and you're not spending time for the rest of your life.

And so it just brought to the fore all of these really difficult conversations, but also sort of empowering ones for who you spend your time with, who you want to be spending your time with and how you want to sort of change the curves as it were over the course of your life.

And so have you made changes in the last year as a result of thinking about this? Yeah. I mean, the biggest change we made was in May 2021 where we picked up our life and sold our house in California, bought a house in New York and moved to be closer to my parents and to my wife's parents.

And that was based on the initial realization of how little time we had left with our parents. Not because they're particularly old or sick, knock on wood, but just based on math and their age, our age, how often we were seeing them about once a year. And now I see my parents at least a few times a month.

They're like a big, big part of my son's life, similar with my wife's parents. They're constantly around. And it makes a huge difference. And it makes them so happy too, to be a part of our lives, to be a part of our son's life. So that was a huge, a huge life change.

And then the kids one is the biggest for me in terms of what it's done in the last year. I mean, I think it's this friend of mine, Kay, he, who has talked about the magic, the magic window, I think he calls it, or the magic years, which is like this 10 year period of time where you are your kid's favorite person in the world.

And once they're older than 10, there are other people that fill that role. They have best friends. They have girlfriends, boyfriends, they get married. They're going to have kids, like they're going to go on and live their entire life where you as their parent are not really the, like the central figure and actor.

But during this 10 year window, you are, and they love you more than anyone else in the world. Yet we live in a culture where traditionally those are the years where you're also working the most and like trying to make the most of your life and of your career.

We were talking about this earlier, like your life is really good, but you also want more, you know, from your career, from businesses you're building. How do you balance those two? Because anything you decide to do or take on is a direct trade-off of time with your kids. You're going to be like, if you're going to be grinding on some business or project or working, that's just time away that you could be spending with them.

And so how do you figure out and find the balance of that? I've been thinking about that more and more and more. And being home during this, like first year of my kid's life and getting to spend tons of time with him and really build a bond with him is meaningful to me.

And so does that mean saying no to a lot more professional things? I mean, like I say no to 99% of opportunities that come my way. And now, I mean, by virtue of the scale of my platform and how it's been growing, it's a lot, like it's a lot of stuff and a lot of financial things that I'm just turning down, you know, out of hand.

And for me, that's been a conscious decision of, I don't actually particularly find myself motivated by money all that much. So I actually don't feel like I need much more money than I have today. And we have a great house and we like our life a lot and we're happy and we have, you know, like I have tons of time at home and free time with my son.

And I actually wouldn't change that much. Like if you offered to pay me today, you know, $50 million to work 80 hours a week this year, I would not do it. Full stop, like wouldn't even consider it. And that's a pretty empowering feeling when you realize priorities and the trade-offs.

But that, I mean, to me, just like really being ruthless about what my North Star is and what I want to focus on has been a pretty liberating thing and a really meaningful thing for me. What do you think has helped you not want to play Keeping Up With The Joneses, which I feel like many of our peers are still feeling that?

I think the biggest thing is avoiding the like when then psychology around this stuff. I saw a great clip of Dax Shepard recently talking about this and how he had all of the trappings that he thought were going to make him happy and successful. And he had convinced himself all on the way that like, well, when that thing happened, then I'm going to be happy and this'll be great.

And then he got that and he realized he was like suicidal and not happy at all. And so it was really liberating that on the back end of getting healed and treated for all of that to realize, "Oh, those external things aren't actually going to ever make me happy." He saw it really viscerally.

Most people never have that. You don't realize that all of those games you're playing in your mind, like, "Well, when I get to vice president or whatever, then I'll be happy because I'm going to be making all this more money." Or, "When I get a million followers on whatever platform, then I'm going to be really happy.

I'm going to have made it. Things are going to be good." The reality is if you're looking for something external to be what creates your internal happiness, it's never going to work out. Happiness is full-on inside job. You have to be finding happiness from something that is a deeper meaning, deeper purpose, something internal.

It can't be some external achievement because it just doesn't last. You just revert to whatever the next when is that you're going to create. For me personally, I've realized that. I stepped off the treadmill around all those things. That doesn't mean that I don't want more because I am motivated by growth, but the growth is an internal thing versus an external thing.

It's not, "Hey, I want to make X dollars or do this or that." It's like, "I want to feel like I'm getting better at things. If that's getting better at being a dad, that's great. If that's getting better at running because I'm really into running right now, then that's great." But it's not, "I want to get a better house.

I want to get a better car. That guy got this, so I want to do that." It's just turned everything internal in a much deeper way. Yeah. The way I describe it for me is I want to feel pulled into things instead of pushed into things now. I had a friend who was like, "I want to start a company." I was like, "Why do you want to start a company?

You started a company. You've done this. You've been successful." The more he thought about it, he was like, "Well, I feel like I don't know what I want to do." I was like, "Just wait until there's a thing that's pulling you towards it instead of trying to push yourself into it." That's what I try to look for, which is ultimately why I left.

I was like, "I just feel that I have to go do this full-time." Yeah. The other way to think about it is, again, I think this is from Tim Ferriss. He has this question of, "What am I saying no to by saying yes to this?" I think about that constantly in the context of family and in the context of what my priorities are.

If my son is my number one priority in the world right now and building a deep relationship with him over this next 10 years and really, really having that closeness and that bond, anytime some new opportunity comes along, I have to think that question through and think about, "Okay, what am I saying no to with him by saying yes to this?" If some new travel comes up, someone wants me to go and speak at something and it's going to require me being gone for a few weeks, what am I going to miss?

What am I going to be saying no to? It might be $50,000 that someone wants me to come speak at something and they're going to pay and it's going to be this cool trip and I'm going to get to go to this cool place, but if I'm missing his birthday party, hell no.

There's no amount of money you could pay me, right? Really thinking that through and it might not be kids. Maybe it's something else. Maybe it's time with your family. Maybe it's some hobby that you really enjoy or a trip with friends that you really wanted to take that you're going to have to say no to because of some new work thing that you're going to really have to dive into if you get the opportunity.

Thinking through those trade-offs I think is a really healthy thing to do, but it requires you to sit back and figure out what your priorities are. What are the core ways that you're going to measure success of your life at the end of the day? Yeah, I mean that could be a whole other episode, so we're not going to go down that path, but I will say that my hack here is I took a lot of time to craft what I thought was like my perfect no email and then I made it a snippet so that I could just fire it off anytime and someone's like, "Hey, I really want to talk about this thing," and I'm like, "I'm heads down.

I should probably just publish it because people could steal it." It's like I'm really heads down focusing on stuff that's important. Feel free to shoot me an email, but not going to have time to meet. Really appreciate you reaching out. It means a lot. Yeah, I do the same.

By making it easy, I use it so much more. Honestly, the difference between thinking about it and having it as a keyboard shortcut level ease makes me send it so often and feel okay about it. I got this, I think it was from Cal Newport. No, it was from Derek Sivers, who was like, "If you're always busy and you can never meet with anyone, you're kind of projecting that you can't prioritize your own time.

And if you leave free time in your calendar, you're able to take advantage of things when they happen that are really interesting." And so I'm trying to live by that. It's hard because especially when you're younger, it's like every opportunity could be more serendipity, more serendipity. But I feel like as we have families and we kind of understand our areas, you've got to really do it.

So I appreciate you saying yes to this because there's always so much knowledge that gets dropped doing it. Where do you want to send people today who are listening and want to stay on top of what you're doing and learn more? I guess my newsletter is probably the best.

You can find it at sahilbloom.com, just my name. I guess sahilbloom.com/newsletter takes you straight to the newsletter. But everything's on my website. And then I'm on all social platforms at Sahil Bloom. The virtue of having a weird name is you get your own handle. Kind messages only. No need for snarky.

Kind messages only if you send me the mean ones. I won't reply, but I will feel empathy for you. Amazing. Thank you so much for being here.