Simplify Decision Making, Reduce Stress and Improve Your Life

00:00:00.000 | if you have enough smart friends talking about something, you should take it seriously.

00:00:03.840 | And again, a lot of these were for me, derived from bad experiences, where I didn't listen to

00:00:11.200 | this, and then I came to regret it. And so smart friends for me, I mean, again, going back to early

00:00:16.080 | COVID, all of these smart friends of mine were talking about board API club as a silly example,

00:00:21.760 | which maybe now it's not as much of a thing. But at the time, it was like this,

00:00:26.240 | whatever, you know, NFT project, I didn't understand what NFTs were, but I had all these

00:00:29.760 | friends that were talking about it. And I was like, dude, that sounds stupid. I'm just going

00:00:33.120 | to ignore this. Like, that sounds super dumb. But I had multiple friends saying it over and

00:00:36.320 | over again. And then like, you know, if I had listened to them, and done something about it,

00:00:41.200 | 12 months after that, I probably would have made like a million dollars off of just putting in a

00:00:45.920 | little bit of money into this thing. And so I developed a rule, basically, that was if three

00:00:49.920 | smart friends, like three friends that I consider intelligent, tell me about the same thing,

00:00:54.000 | I'm going to put like a little bit of skin into the game, no matter what, even if I'm not going

00:00:57.520 | to go deeper on it, it just like gives me kind of a hedge against looking like an idiot later

00:01:02.000 | on, like I did with that one. Zile, thanks for being here. I'm so happy to be doing this in

00:01:11.520 | person. I know. I don't do a lot of these in person. We're here in New York City at Podstream,

00:01:16.480 | which I've never been to, but right in the center of Times Square, but we are in a dark room between

00:01:21.120 | two ferns, as it were. Yeah, we are. So, so much of what you've written online for the past few

00:01:27.120 | years has had a big impact on me. And every time I come into a conversation, I'm like, oh, there's

00:01:31.520 | so much, but I got this advice from someone recently about travel. They said, whenever you

00:01:35.920 | go to travel, pretend like you're going to that city a million times for the rest of your life.

00:01:40.400 | Just don't, don't feel like this is your last trip. So I'm gonna treat this conversation like

00:01:43.680 | it's not our last conversation on the show, so I don't have to cover everything. So I thought back

00:01:48.480 | to kind of the first content of yours that I'd read, and it was all about razors, which at the

00:01:52.640 | time I was like, I don't even know what that is. And I felt like that would be a great place to

00:01:57.520 | start for this conversation, but like everyone else listening, I'm sure people don't know what

00:02:02.960 | razors are. So can you talk a little bit about what they even are and we can jump into why they're

00:02:07.120 | important? Yeah, absolutely. So it's not for shaving. Yeah. Would be the first thing I would

00:02:12.160 | start with, I suppose. No, I mean, a philosophical razor, the term is from philosophy and basically

00:02:18.640 | the idea is that it's a rule of thumb or some sort of decision-making heuristic that allows you to

00:02:23.280 | cut through available options and make a decision. So the whole idea was like in philosophy, you can

00:02:29.040 | take a razor and it allows you to like strip away any of the unnecessary things in order to cut

00:02:33.680 | through the noise and just make a decision. So Occam's razor is the one that if people know a

00:02:38.080 | single razor, Occam's razor is the thing they've heard of. And that's like the whole idea that

00:02:42.000 | basically simple is beautiful. It's like if you have a whole bunch of hypotheses, the one that

00:02:46.880 | requires the fewest assumptions is generally the one that is right. If you're kind of like looking

00:02:52.480 | to decide which path you believe is the driver of some situation. So I've written a bunch about

00:03:00.400 | razors and basically like extending the concept into a whole bunch of different realms. I think

00:03:04.960 | a lot about ways to simplify decision-making. It's always been something that I've liked.

00:03:08.800 | You're sort of similar to that, like life hacks, right? Are all sort of razors in their own way,

00:03:12.960 | shape or form, like ways to make a decision, cut through things, that'll just simplify your life,

00:03:18.640 | hopefully, like tools in your toolkit. So that's been the kind of genesis of me writing about them

00:03:23.360 | in the past. Yeah, I think when it comes to my whole scope in life is like, how do I optimize

00:03:27.840 | everything? I think one of the challenges you get into is there's just too much and you get

00:03:32.000 | overwhelmed. So for me, I love these idea of razors, rules of thumb to just make some of it

00:03:37.520 | a little easier. Although the risk is that you then have like a million razors, which would be

00:03:41.840 | the pushback against this, which is like, "Oh, I have a million razors. I can't remember a single

00:03:45.440 | one of them." So the way I always think about these things is like tools in your toolkit.

00:03:49.600 | You don't need to like know that you have all of those different wrenches or all those different

00:03:53.840 | things at every single point in time. You just need to like have your toolkit and be able to

00:03:58.320 | open it up and think about, "Okay, what applies to a situation at any point in time?"

00:04:02.480 | Yeah, and I don't expect anyone listening to go home and be like, "I got 17 razors to use in my

00:04:06.880 | life." I did try to bulk them into a couple of categories because I thought that might be helpful

00:04:11.920 | for people to think, "Okay, I need to make a decision on this thing. Is there something that

00:04:16.240 | might make this easier?" So the first one I thought about was related to people. There's people in

00:04:20.720 | your life. First one I had was the optimist razor, which I consider myself an optimist,

00:04:24.640 | so I like this one. Let's start there and kind of go through a few people one and see where we get.

00:04:29.280 | Yeah. So the optimist razor is basically the idea that you should always default to trying to spend

00:04:35.440 | time with optimists. And if you have a choice between spending time with optimists and pessimists,

00:04:39.440 | you're always better off spending time with optimists. And the grounding of this, I mean,

00:04:43.520 | I originally came up with this during like the period of COVID when there was a whole ton of

00:04:48.400 | pessimism out there around like, "Oh, the markets are going to hell. The economy is going to hell."

00:04:52.720 | And then there was like little shades of optimism and like kind of mid-2020 about,

00:04:58.000 | "Okay, but a lot of these things are happening X, Y, and Z that might be positive actually for

00:05:02.800 | the future." I mean, the Fed was printing trillions and trillions of dollars. And what I found was

00:05:08.000 | my initial skew was to pessimism. And I was like, "Oh, short the market. Everything's going bad.

00:05:12.320 | Everything's going bad." And really regretted that after a few months when I realized that

00:05:16.720 | the optimists were actually the ones that were getting rich by betting on things going well in

00:05:21.520 | that time period. And so, I started just thinking about, "Well, there's this little heuristic that

00:05:27.360 | pessimists sound really smart, but optimists seem to be getting really rich." And it all of a sudden

00:05:35.200 | cemented in my mind like, "Okay, there's something to this. And really, I want to be spending more

00:05:39.440 | time around optimists in general." But it's not just about investing and making money.

00:05:44.080 | It can be just who you want to hang out with on the weekend.

00:05:46.240 | Totally. I mean, that's why it applies so broadly to life. And when I took it beyond that,

00:05:51.360 | I just started thinking, "Who do you feel good when you're around?" Just as a general rule of

00:05:56.960 | thumb. You're like, "Who do I get energy from? Who makes me happy and feel good to be around?"

00:06:02.480 | And that tends to be optimists. Again, pessimists, they sound smart. They have a lot of things and

00:06:08.000 | negativity, et cetera. But being around people that are positive and optimistic about the future,

00:06:12.160 | about what it looks like in any arena, just tends to feel better. And what I find is that good

00:06:17.200 | things happen when you spend time with optimists. They just have a better outlook on the future.

00:06:21.120 | And if you believe that energy attracts energy, optimists tend to attract good outcomes.

00:06:26.480 | Yeah. What about finding people to work with more than just hanging out?

00:06:31.440 | Yeah. I mean, it applies to another kind of area that I've thought about, which is

00:06:35.600 | originally from Nassim Taleb, the author of Black Swan, who I don't know if... I forget what book

00:06:43.600 | 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

00:06:47.520 | Anti-Fragile, where he talks about this whole thing of the surgeon and how you pick a surgeon.

00:06:52.960 | And so he tells this story of you choosing between two surgeons who are of equal merit. Assume they

00:06:59.520 | both have the same track record of successful surgery, say. And one of them looks like this

00:07:03.760 | beautiful, polished Harvard Medical School credentialed surgeon. Perfect, clean cut,

00:07:09.120 | everything's good. And then the other one looks like a butcher. He's got blood all over him.

00:07:13.120 | He just doesn't look the part. He's big hands, whatever, big beard, scraggly.

00:07:18.480 | And his whole thing is that most people pick the nice, clean cut surgeon when what you should

00:07:24.320 | actually do is pick the one who doesn't look the part. And his logic is that the one who doesn't

00:07:29.440 | look the part has had to overcome not looking the part in order to get to where they are.

00:07:33.920 | And so if they have equal merit, that one is actually the better one because they've had to

00:07:37.920 | overcome not looking like they should all along the way in order to get to that level.

00:07:42.960 | And I've always thought that was like another interesting way of thinking about who to work

00:07:46.160 | with, because we do have all of these little biases and prejudices that are in our head.

00:07:50.800 | And people that have managed to overcome all of those all along the way to get to where they are

00:07:55.360 | tend to be great, great people to work with. - Yeah, I don't know if you've ever done

00:07:58.880 | unconscious bias training, but it just kind of like opens your eyes up to, "Oh, okay."

00:08:04.240 | Like even someone who might not think you have bias, you have bias for sure.

00:08:07.520 | - Yeah, I mean, the statistics on those things are insane. Like you can go on Google and just

00:08:11.680 | like look one up and do one of the tests quickly and you can get like a score on it. It's usually

00:08:15.760 | pretty shocking. - Yeah.

00:08:16.720 | - What about smart friends? - Again, like with people, man,

00:08:21.120 | the smart friends one is basically that if you have enough smart friends talking about something,

00:08:27.920 | you should take it seriously. And again, like a lot of these were for me derived from bad

00:08:34.720 | experiences, like where I didn't listen to this and then I came to regret it. And so like

00:08:38.640 | smart friends for me, I mean, again, going back to early COVID, like all of these smart friends

00:08:43.120 | of mine were talking about board API club as like a silly example, which maybe now it's like not as

00:08:48.560 | much of a thing, but at the time it was like this, you know, whatever, you know, NFT project.

00:08:53.440 | I didn't understand what NFTs were, but I had all these friends that were talking about it.

00:08:56.800 | And I was like, dude, that sounds stupid. I'm just going to ignore this. Like,

00:08:59.280 | that sounds super dumb, but I had multiple friends saying it over and over again.

00:09:02.400 | And then like, you know, if I had listened to them and done something about it, 12 months after that,

00:09:08.240 | I probably would have made like a million dollars off of just putting in a little bit of money into

00:09:12.240 | this thing. And so I developed a rule basically that was if three smart friends, like three

00:09:16.560 | friends that I consider intelligent, tell me about the same thing, I'm going to put like a little bit

00:09:20.720 | of skin into the game no matter what, even if I'm not going to go deeper on it, it just like

00:09:24.640 | gives me kind of a hedge against looking like an idiot later on, like I did with that one.

00:09:29.120 | But again, it's just another way of thinking about, you know, drafting off of the intelligence

00:09:35.440 | of your peer group. Like if you have smart people that are talking about things and you're in these

00:09:39.680 | circles with intelligent people that have domain expertise that goes beyond yours, listening to

00:09:44.320 | them and taking it seriously when there's enough density in a single idea is usually a good bet.

00:09:49.600 | Presumably they have to be excited about it or just talking about it. I think excited about it,

00:09:54.080 | you know, like, and again, and domain experts, right? Like not just like you don't want to have,

00:09:59.120 | you know, your like coder and engineer friends, maybe like weighing in on like culture and

00:10:04.720 | fashion and being like, oh, I'm going to listen to them. Like you want it to be people like if

00:10:08.800 | they're in technology and they're weighing in on some new technology, like AI could be an example

00:10:12.720 | today. If you have a certain domain within AI that a bunch of your smart friends are really

00:10:17.200 | interested and excited about, it's worth taking seriously. It doesn't mean you have to invest in

00:10:20.720 | it or do something, but it's worth at least digging into it and trying to understand more

00:10:24.320 | because it might be like an asymmetric bet on the future. - Right now, I feel like this about AI,

00:10:29.920 | except I just don't know how to make that asymmetric bet. Or maybe it's not even asymmetric

00:10:33.760 | anymore because what is it like a hundred million people are using chat GPT at this point?

00:10:37.360 | - Is it really a hundred million people? - The growth curve on chat GPT, you can search it,

00:10:40.960 | or I'll find the link and put in the show notes. It's like, you know, Instagram grew to a hundred

00:10:45.280 | million users this fast and all this, and you see these curves like this. And then chat GPT is just

00:10:49.360 | like a straight line up. I think I've seen that. I still just wonder with technology stuff like

00:10:57.200 | this, how much of it is that we're just in a bubble of sort of like semi-nerdy people on Twitter

00:11:01.760 | versus true mass proliferation of an idea. I honestly just don't know. I think chat GPT

00:11:09.120 | is probably across the chasm, but I used to wonder that like with web three stuff,

00:11:13.440 | like if you go to like a normal person on the street, they're like, "What the hell is an NFT?"

00:11:16.640 | Right? And so like there clearly wasn't a mass proliferation of the idea.

00:11:20.640 | The utility of chat GPT makes me believe that it is actually mass proliferating.

00:11:25.280 | - It's funny because I had this experience this morning. I flew to New York today and I'm waiting

00:11:29.600 | for my bag to go through the metal detector. And I hear three TSA agents talking about AI. And

00:11:35.200 | they're like, "Yo, I use this thing and it creates song lyrics, it creates art." And I was like,

00:11:40.400 | "Okay." It's clearly crossed to the mainstream, but the use cases everyone's excited about are

00:11:46.240 | not necessarily use cases that I think will drive business. The challenge I have is it's something

00:11:51.520 | that I feel really passionate about being big and have no clue how to bet on. And there was a pretty

00:11:56.640 | good episode of the All In podcast where they were debating how to invest in this space.

00:12:01.360 | And these are some of the smartest investors in the world. And I can't remember which one said,

00:12:05.760 | "I still haven't invested." Because if you look at the early days of so many of these industries,

00:12:10.640 | even look at social, the first few social networks actually didn't work out. And so I'm frustrated

00:12:16.720 | because I feel like there's a there there, but I don't actually know what to do about it.

00:12:21.200 | You also have to separate it. If you're going to invest, you also have to separate it from

00:12:24.320 | hype cycle. Normally, TSA agents talking about it, I would say is really peak hype cycle of

00:12:28.800 | something. And so hype cycle drives valuations. And so if you're looking... I have this fund where

00:12:33.760 | I invest in early stage companies. And if you were to look at the average deal that says they're an

00:12:39.360 | AI company right now, the valuation at pre-seed or seed is like $25, $30 million, which is very,

00:12:45.120 | very hard to drive a return in the aggregate across an asset class. And so that's what I

00:12:51.040 | struggle with. They're benefiting from hype cycle on their early valuation, which hurts investors on

00:12:56.080 | the margin. And so it's tough. It's tough to discern, "Okay, what's there? What's actually

00:13:00.880 | just going to get eaten by whatever big company decides to do this?" It's tricky. And most of them,

00:13:05.520 | by the way, are just doing an open AI API call. They don't actually have anything internally or

00:13:10.800 | proprietary about it. And so again, it's like, "Okay, you're just linking to another person's

00:13:15.200 | platform." Yeah. The number of companies that have pitched me a thing that's like, "Hey,

00:13:19.200 | we take a document and we give you answers on it." And I'm like, "There's literally... You're

00:13:22.480 | just monetizing this other API." With your own UI/UX. Although a lot of companies have been

00:13:27.280 | built in that general way in different areas where it's just like, "Oh, we link to whatever

00:13:32.000 | platform we're using their backend." So I'm not saying that company can't make money. I'm just

00:13:36.080 | skeptical in investing in anything at these valuations. Totally. Totally.

00:13:38.720 | But to come back to Razors, what do you do when someone comes to you with a crazy idea?

00:13:43.360 | Oh, man. So my favorite thing around crazy ideas is... I think it was Paul Graham. Yes. Paul Graham,

00:13:52.000 | the famous investor, he didn't actually frame it as a Razor. I turned it into a Razor,

00:13:57.280 | but he wrote this piece on what to do if someone comes to you with a crazy idea.

00:14:01.600 | And basically, his thing boiled down to two questions to ask yourself, "Are they a domain

00:14:06.080 | expert? And do I know them to be a reasonable person?" And if the answer to both of those

00:14:10.480 | things is yes, then you should probably take the idea seriously because it might be an asymmetric

00:14:15.280 | bet on the future. And I thought that was such an elegant way to think about this because

00:14:19.040 | it's very easy to write off crazy ideas. You hear something and you're like, "You don't understand

00:14:23.520 | this." You're just like, "That sounds ridiculous. That seems ludicrous that that would ever happen

00:14:27.920 | or that the future would look like that." But if you slow down and you ask yourself those two

00:14:31.360 | questions, you can actually totally deconstruct the entire problem. You're asking, "Are they a

00:14:36.160 | domain expert? So do they understand this thing that they're talking about, the area around this

00:14:40.720 | thing very, very well?" If the answer is yes, move on to the next question, which is, "Are they a

00:14:44.160 | reasonable person or are they completely ridiculous?" And if you know they're completely

00:14:47.360 | ridiculous, you're like, "Okay, maybe I'm going to hesitate a little bit." But if they're not,

00:14:51.760 | if you know that they're a reasonable person and that they do reasonable things,

00:14:55.520 | now you start to take the whole thing seriously a little bit based on those two.

00:14:58.960 | So I've always thought that that was a really, really good way to cut through the noise on it.

00:15:02.800 | Yeah. I find that my instinct is often to be like, "That's not right."

00:15:07.280 | Totally.

00:15:07.840 | I think that's most of our common instinct when we hear anything.

00:15:10.400 | Especially because I don't understand it. I'm not technical enough to know on most of these things.

00:15:14.720 | And so when someone says something that sounds crazy to me about the future,

00:15:18.000 | what the future is going to look like, what people are going to be doing, my default is like,

00:15:21.600 | "That's stupid. No, no way." And generally, on five or 10-year time horizons, anything I thought

00:15:27.440 | was stupid, I've been completely wrong about. If there were enough people talking about eSports,

00:15:31.600 | people filling... Someone said this to me in, I don't know, it's probably 2009. When I got to

00:15:37.360 | college, someone was like, "Dude, eSports is going to be the next big thing. People are going to fill

00:15:40.640 | stadiums watching people play video games." And I was like, "You are an idiot. I'm not listening

00:15:45.200 | to you anymore. That was dumb." And again, if I had bet on that in some way, that would have turned

00:15:49.920 | out pretty well for me at the time. And so now my new default is like, I take anything any smart

00:15:55.360 | person says, at least remotely seriously. It's like I had one of my razors was around listening.

00:16:01.040 | And the whole idea was like, if someone says something that is very different from your

00:16:06.480 | beliefs, you should listen twice as much as you speak. And that applies to this type of thing

00:16:13.040 | with new investment ideas or ideas on what the future of technology looks like, just as much

00:16:17.440 | as political debates or anything that you're trying to educate yourself on. Because generally,

00:16:22.720 | our bias when we hear something that we don't agree with becomes, "Okay, I'm just going to

00:16:28.560 | talk over them and I'm going to tell them why they're wrong about this thing." But if you flip

00:16:32.160 | the script on that and you say, "I'm actually just going to listen to a whole bunch and at least hear

00:16:36.640 | them out," usually you end up learning something. Even if you don't agree with them at the end,

00:16:40.240 | that's fine, but you end up learning something from how they're thinking about it.

00:16:43.840 | Well, also, I think one of your life hacks, so Silas' great PDF of 50 life hacks,

00:16:49.200 | if I remember right, is trying to be interested, not interesting.

00:16:53.200 | Yeah. Yeah. I mean, this is like a simple reframe. Especially when you're young,

00:16:58.880 | I definitely fell into this trap when I first started my career. My whole thing was like,

00:17:03.440 | "Okay, if I'm going to go to an event and I'm going to talk to people, I really want to be

00:17:06.640 | interesting. I want to talk about all the interesting things I'm doing or the interesting

00:17:10.240 | things." The challenge is you're actually just not that interesting at age 22. I mean, on the margin,

00:17:14.880 | most people are not that interesting at 22. At 25, frankly, most people aren't interesting for

00:17:19.760 | the first 10 years of their career because you just haven't done enough. There's not enough

00:17:22.960 | experiences in your life. My whole reframe around it is focus on being interested rather than

00:17:29.520 | interesting. Being interested means you're listening to people. It means you're asking

00:17:33.680 | follow-up questions. You're diving down the rabbit hole with them to learn more about why they think

00:17:38.160 | certain things or why they're interested in certain things. When you do that, people want you around

00:17:43.760 | because interested people are really fun to be around because they're actually listening to you

00:17:47.680 | and they're actually asking follow-up questions. Most people at a cocktail event or at a party or

00:17:52.240 | whatever are just waiting for their turn to speak. You're talking to someone, having a conversation,

00:17:57.600 | and you see them sitting there and they're just like, "Mm-hmm, mm-hmm, mm-hmm." Then as soon as

00:18:01.200 | you get done, they're like, "Ah," they jump in with their thing. That's not a particularly fun

00:18:05.040 | conversation part. I just think it's a great way to stand out in conversations and to actually

00:18:09.920 | learn things when you're in them. It doesn't even have to be if you don't have anything

00:18:13.280 | interesting. It could just be to build more relationships. Totally. I just think it's a

00:18:16.240 | good way to live life in general. You end up learning so much interesting stuff by just

00:18:20.720 | being interested. Paradoxically, being interested is how you become interesting because then you end

00:18:26.960 | up getting into those cool situations. You end up learning interesting things. That's what you end

00:18:31.280 | up going and capitalizing on, working on, etc. How do you start that conversation? I think there

00:18:35.280 | was another life hack by just how to start the conversation to build it. I just found meetings

00:18:41.360 | or situations where I was way over my skis early in my career. I've always just been great about

00:18:48.560 | finding my way into weird situations that I don't belong in. Even this last weekend, I was at the

00:18:53.360 | Berkshire Hathaway annual meeting and I had a chance to talk to Bill Gates. In a situation like

00:18:59.280 | that, you're like, "What am I possibly going to have to offer or talk to Bill Gates about? I don't

00:19:02.960 | have anything possibly interesting that he would find interesting, given who he has access to."

00:19:08.480 | What I found is that the best way to get someone like that talking in what would otherwise be a

00:19:13.200 | weird, clumsy, awkward situation is to ask them what they are most excited about in their life

00:19:17.920 | right now. That can be personal or professional. They can take it however they want it.

00:19:21.520 | Normally, really successful people have something that they're fired up about at any point in time.

00:19:27.600 | If you can get them talking about that, then it becomes really easy. The pressure's off you.

00:19:31.520 | They're excited. They're energetic about whatever it is that they're telling you about.

00:19:35.280 | Then you can just ask follow-up questions. You can just dig deeper on stuff, again,

00:19:38.720 | to being interested. That becomes a much, much easier conversation with anyone.

00:19:43.280 | So, what was Bill Gates interested in? What was Bill Gates excited about?

00:19:46.640 | I actually don't know that I'm allowed to talk about the thing that he was excited about

00:19:51.200 | in public because it was in a private setting. I actually don't want to share it.

00:19:55.040 | Okay, but it was a fun conversation. I mean, short, fun conversation. You get someone that

00:20:00.080 | otherwise you would be like, "Hi," to talk for five minutes. That's an amazing experience and

00:20:05.120 | opportunity. It was generally around climate technology, something that he's working on.

00:20:08.880 | I think it'll be public. I think it is public, maybe, but I just don't want to.

00:20:11.840 | It's funny. I talked to Catherine Minchu, who runs this company called The Muse,

00:20:14.800 | based in New York. Her power move in situations like this, also, when you're talking to someone

00:20:19.280 | that's more senior than you, chances are that person is like, "When is this going to end?"

00:20:24.160 | Yes, you can make them excited. She tries to be the one that always ends it first.

00:20:28.000 | She's like, "Oh, I'm going to remember that person. I could talk to them again

00:20:31.040 | because they didn't just sit here and dominate my time."

00:20:32.880 | Oh, that's interesting.

00:20:33.920 | She brought up a time where she was at some conference, and she was talking to Elon,

00:20:37.840 | and in the middle of it, she's like, "Hey, you know what? I got to go.

00:20:40.240 | It was really great to talk to you," and just walked away.

00:20:42.160 | That is a power move.

00:20:43.040 | And she said it's made people that otherwise would be like, "When is this person going to

00:20:47.760 | leave this conference?" It just made it so much better.

00:20:50.080 | Yeah, and it makes it less awkward for them to have to end it, too, when you just do it.

00:20:53.520 | I also find, by the way, that following up and sending someone a book is one of the best life

00:20:58.080 | hacks in the world because all of these hyper, hyper successful people get sent so many fancy

00:21:04.880 | bottles of wine, expensive champagnes, expensive bottles of alcohol, super nice gifts that you

00:21:10.800 | couldn't possibly spend enough money to send them something that would stand out.

00:21:14.160 | But if you send someone a book that really mattered to you with a handwritten note on

00:21:18.800 | personalized stationery of why you think it'll resonate with them and something from the

00:21:24.320 | conversation that you enjoyed, you'll always stand out in their mind forever. They'll remember that

00:21:29.200 | because no one really does that. It's just an old-fashioned thing. So, it's a great,

00:21:32.480 | great way to stand out with people.

00:21:33.840 | Is there a book you've gifted the most?

00:21:35.840 | Yeah, One Breath Becomes Air, by far. Probably 95% of the time,

00:21:40.560 | that's the book I share with people. If you've never read it, it's unbelievable.

00:21:43.200 | I know. I haven't read it. I'm like, "Oh, man."

00:21:44.800 | Oh, you haven't?

00:21:45.520 | No.

00:21:45.840 | Oh, my God. Well, it'll knock you out. I read it on a plane for the first time,

00:21:50.560 | and the last piece of it, I was full-on crying on this flight, and the woman next to me had

00:21:57.120 | to ask if I was okay. So, don't read it in a situation where you're not comfortable crying.

00:22:03.200 | Okay.

00:22:03.920 | So, to wrap up all of these people-related razors, I want to talk briefly about Henlon's Razor.

00:22:12.320 | Never attribute to malice what could otherwise be attributed to stupidity,

00:22:16.800 | is the way that that is typically put. So, basically, the idea is if someone does something,

00:22:22.960 | we have this tendency to say, "Wow, they're acting maliciously. They're acting negatively

00:22:28.000 | towards me or towards other people, whatever." And we should never do that if stupidity is a

00:22:32.800 | potential argument. So, it's like the whole idea that we give people too much credit for being

00:22:37.280 | malicious actors, when in reality, they might just be ignorant or dumb or unintelligent, etc.

00:22:42.800 | This is a great one for Twitter. In general, you read people sending mean comments or saying things,

00:22:50.640 | and you're like, "Oh, they're acting so maliciously, and they're acting in such a

00:22:53.680 | bad-faith way," when sometimes you can just chalk it up to them being ignorant or stupid.

00:22:58.720 | Is this similar to assume best intent or in the ballpark? Because I feel like that's one I use a

00:23:05.120 | lot. Yeah. I'd say it's similar. Maybe, yeah. Assume best intent is probably a nicer way of

00:23:12.240 | saying this. I just always found Hanlon's razor to be really funny because it's just like,

00:23:15.760 | if you are finding that you're thinking someone is acting in some

00:23:20.240 | bad, nefarious, calculating way, sometimes it's just that they're just not intelligent.

00:23:24.400 | Okay. So, I think we covered a bunch of... You've written multiple posts with lots of

00:23:31.040 | razors in lots of forms. I tried to pull some from the old posts, some from the new posts,

00:23:35.040 | and that was a lot of things related to interactions with people. I'll link to those

00:23:39.440 | posts in the show notes. What I like is that, in a lot of those posts, you say, "Hey, use this when

00:23:44.000 | you're deciding who to hang out with. Use this when." We can link there if you want to recap

00:23:48.720 | from this conversation. The other area that you alluded to at the beginning is making decisions,

00:23:53.200 | which I think is something that, when optimized, can really save you time because I know myself

00:23:59.120 | and a lot of people listening spend a lot of time making decisions, trying to get to the optimal

00:24:02.800 | outcome. So, let's talk about a few of these decision-making ones. Let's start with the arena.

00:24:09.440 | The arena. This all comes from the man in the arena, Teddy Roosevelt's speech of,

00:24:14.880 | "It's the person in the arena that really counts." And my whole operating principle around this is

00:24:22.800 | that you should always try to put yourself in the arena. And that takes on different forms

00:24:28.720 | in different areas of life, but basically, don't sit on the sidelines and sling rocks at people

00:24:33.680 | that are out there doing things. And so, if you have a choice of two paths of how to operate,

00:24:38.960 | you should put yourself in the vulnerable position in the arena because that's where

00:24:42.720 | you end up having the high upside things happen. That's where real growth occurs and where you end

00:24:47.360 | up having those wins, et cetera. You can't really win long-term by sitting on the sidelines,

00:24:52.720 | especially not sitting on the sidelines throwing rocks at people that are out there.

00:24:55.760 | And you said this is the one you feel the most strong about in one of these posts.

00:24:59.760 | Yeah.

00:25:00.260 | Have you seen a lot of personal wins from playing this?

00:25:03.600 | Yeah. I mean, I think that it's the most wins, but it's also the most,

00:25:09.440 | I don't know, emotionally draining and trying sometimes because by putting yourself in the

00:25:14.720 | arena, you're exposing yourself to the whole lot of people out there that do just want to sling

00:25:18.720 | rocks from the sidelines. I mean, you've seen it, right? We're sitting here, you're producing this

00:25:22.640 | podcast. You've been creating this for a long time. You share everything publicly. It's out

00:25:26.400 | and about. There are going to be people that don't like it, that criticize it, et cetera.

00:25:30.080 | That's not fun because you're like me. You're a very positive, optimistic person. You're happy.

00:25:34.800 | You generally are just a good, positive guy. And when there's random people out there that

00:25:40.240 | are reading your stuff or engaging with your stuff and are like, "I hate Chris. He's awful.

00:25:44.720 | What a bad person," et cetera, it's a weird feeling where someone doesn't know you and

00:25:48.560 | they're engaging that way, but you've gotten so much upside from putting yourself in the arena

00:25:52.880 | and just consistently putting things out there. So I think it's like you have to be able to have

00:25:58.160 | thick skin and take it when you're going to be putting yourself in the arena, but that's where

00:26:03.120 | the real wins actually end up happening. So for me, with my platform, with anything I'm

00:26:07.040 | putting out there, you're constantly putting your neck on the line and exposing yourself to it.

00:26:10.960 | And when you're sharing ideas publicly, that's a very vulnerable state to put yourself in.

00:26:16.080 | The same thing applies to working in a corporate job. If you're going to put your ideas on the line

00:26:22.400 | with your boss or with your team or however you're going to do it, again, it's very easy to just sit

00:26:28.000 | back and let other people do that, but that's not how you're going to end up progressing and making

00:26:32.560 | it to the next level of whatever you want to do. Any tips for how you take that negative feedback?

00:26:37.600 | I feel like I'm fortunate because I don't love that podcasts are such a one-way medium

00:26:43.440 | that I don't hear. It's so much more effort to be like, "Oh, I was listening to something cool.

00:26:47.680 | Now I'm going to go find that person's contacts, send them a note." So I tend to get pretty

00:26:51.440 | positive feedback because it's people that were pretty excited about what happened and sent an

00:26:55.280 | email and I replied to them. I know you replied to a lot of, if not all the emails you get.

00:26:59.280 | But a friend of mine posted on the close Instagram thing this morning. She posted

00:27:03.600 | something online. She's like, "I'm just having a bad day." And she posted a picture of Ben and

00:27:06.560 | Jerry's. "I'm having ice cream." And she posted photos on her close friends of all the DMs she

00:27:12.000 | got. And people are like, "I can't believe you would promote a brand like that." Or like, "Can't

00:27:15.920 | you eat healthier ice cream?" And I was just like, the internet can be a mean place, especially

00:27:22.320 | social media, which I don't spend a lot of time on as much as I do recording. But I know a lot

00:27:27.760 | of people have probably faced this, whether it's at work, throwing out a bad idea. How do you take

00:27:31.120 | that? Because I'm sure you've gotten a lot. I think defaulting to empathy is the single

00:27:36.160 | healthiest and best way that I've found to combat negativity. Basically, when someone says something

00:27:42.800 | super negative on the internet to someone that they don't know, it's pretty fair to assume that

00:27:47.760 | that person is not in a happy place in their life. Like happy people... Have you seen Legally Blonde?

00:27:52.720 | This is going to be an embarrassing reference. In the movie Legally Blonde, she's like, "Happy

00:27:56.880 | people just don't kill their husbands. They just don't." And I think about that with happy people

00:28:01.920 | on the internet. Happy people just don't comment mean things to other people's posts on the internet.

00:28:06.480 | They just don't. It's just not a thing that you would think to do. You're a happy guy. I don't

00:28:09.840 | think you would think to go and attack someone that you don't know on the internet. It's just

00:28:13.600 | not a thing you would do. And so, I tend to think that when someone attacks you with negativity,

00:28:17.440 | there's usually something that's going on in their life that's tough. And we don't know what that is,

00:28:23.120 | and we're not behind that person's eyes. And so, I try to default to empathy when I read something

00:28:27.120 | like that, of just like, "Oh, that person's having a tough day." Or the person is in a tough spot for

00:28:32.000 | whatever reason, and not get all wound up about it. I never engage or fight back on that kind

00:28:37.440 | of stuff. Because again, it's like, I'm not going to convince them they're wrong. I'm not going to

00:28:40.720 | make their life better or change it. And so, there's no point. Back to some of the career

00:28:46.080 | stuff. What about when you're faced with trying to decide between two paths you could take at work?

00:28:52.320 | So, this is one from Naval that I really like, where he talks about making uphill decisions,

00:28:58.240 | I think is the way that he phrases it. Which is basically when you choose between two paths,

00:29:02.640 | you should choose the path that is harder in the short term, because those tend to be the

00:29:07.040 | paths that work out better in the long term. So, it's like the whole short phrase of hard

00:29:12.320 | choices now, easy choices later, easy choices now, hard choices later. And I think it's an

00:29:17.360 | interesting, although nuanced one, to be totally honest, as I've thought more about this one over

00:29:21.200 | time, because sometimes choosing the hard path means that you're not allowing yourself the time

00:29:29.440 | to think about whether there's an easier way to do it. Like Tim Ferriss, who I know we both really

00:29:33.520 | like his work, talks about often, what if this were easy? What would this look like if this

00:29:37.920 | were easy? And I think it's a really important question to constantly ask yourself, is there

00:29:42.560 | actually an easy mode that I can play this game on that I'm just ignoring because I'm taking pride

00:29:47.520 | in doing it the hard way? And as someone who's sort of a recovering hustle culture bro from back

00:29:53.360 | in the day in finance, I often missed the easy mode way of playing the game because I was so

00:30:00.080 | prideful about playing the hard way. And so, I think this uphill decision one is actually a

00:30:05.440 | nuanced one I need to think about more and that people should think about more of anytime you're

00:30:10.560 | doing something and it feels hard and difficult, you should pause and ask yourself, is there

00:30:15.040 | actually an easy mode? Is there an easy way that I can do this that I'm just missing out on because

00:30:20.720 | I'm grinding away in the way that I am? - Yeah, and I sometimes think there's both

00:30:25.200 | easy and I sometimes think that gets caught up in cheaper, especially in a world of trying to

00:30:32.240 | optimize your life and your money and you're like, oh, well, this is the cheapest way,

00:30:34.960 | so I should do it this way. - Give me an example of that.

00:30:38.080 | - So my wife and I, I've just talked about this on another episode, I don't know if it will have

00:30:42.240 | aired at this point, but my wife and I are talking about our children and we have a daughter who's

00:30:47.200 | about to be three, you'll learn this in a couple of years and she had this stint where she would

00:30:53.680 | just get out of bed after going to bed. She'd say, run out the door, open the door and say,

00:30:57.520 | I have to go to the bathroom. Okay, I need a stuffed animal. She would just get out of bed

00:31:02.000 | constantly and my wife and I are like, okay, what do you do? You go on the internet and there's

00:31:06.400 | a bajillion people who have an opinion about what to do and it's hard to figure out what the right

00:31:10.560 | thing is. So it's like, what's your manifesto? Who do I trust? And when it came to a lot of

00:31:16.400 | early decision stuff, we just went to Emily Oster, who's written a few books about parenting and

00:31:20.880 | she's like, this is what you need to know about the expecting phase, the baby phase, but I didn't

00:31:25.040 | have something from her for this. And my wife was like, well, I really like the content that this

00:31:28.880 | company called Big Little Feelings puts out. And I believe we use their course for potty training.

00:31:34.480 | And it was like, instead of reading 10 books, my wife's just like, I really like how they teach

00:31:39.120 | what they believe in. So she took their course, it was 30 bucks or something. She's like, we have

00:31:43.200 | this other course, it's $100. And she was like, do you think it's worth spending $100 to get a

00:31:49.040 | source I really trust database of how to handle every toddler scenario? And I was like, well,

00:31:54.800 | what's the alternative? So what we did was we were like, well, one alternative. So I just asked

00:31:58.240 | ChatGPT, I was like, what should I do? Answer was like, okay, it's surprisingly good. But it's like,

00:32:03.520 | do we want to go do a bunch of research or just trust this thing? And so a part of my mind was

00:32:07.600 | spinning saying, well, I could go find the answer. The answer exists on the internet, it's all this

00:32:12.640 | work and it's the cheaper one. So I was both taking this uphill battle of the hard work of me

00:32:18.160 | deciding what the right answer is, but also the cheaper answer. But my wife asked me, and this

00:32:22.400 | time she was in this situation I usually am, which is like, she's saying I want to do all the work.

00:32:25.840 | And what I learned is it was really easy for me to make a different decision when it wasn't

00:32:30.720 | for me. And when I put a little bit of emotion in it, I was like, just buy the thing. No problem.

00:32:35.360 | It was an easy decision for me, but for her, it felt so hard because she was like, well,

00:32:39.680 | I could do this research, could do it. Maybe I'd learn more.

00:32:42.320 | So cheap is not always cheap. The thing I've always found is that the thing I think is cheaper

00:32:47.520 | is generally more expensive. And I find this with everything. I've always been a big, this is me not

00:32:53.760 | being frugal too, but I've always been big on just like, my wife would ask, we were getting our new

00:32:59.680 | house here in New York and she's like, what furniture? There's this furniture or there's

00:33:04.640 | this furniture. And I was like, just get the nice one because you're going to have it.

00:33:08.480 | And getting the cheap furniture sounds good when you get it and it's 50% cheaper, but when it

00:33:13.680 | breaks and you need to get new, we got cheap outdoor furniture and really nice indoor furniture.

00:33:18.480 | Well, the outdoor furniture after one winter in New York now looks like crap and I'm going to

00:33:22.080 | have to buy new outdoor furniture. Now I'm going to have to get the nice outdoor furniture so this

00:33:25.680 | doesn't happen again because I don't want to replace it every year. Would have been better

00:33:28.080 | off just getting the nice one and taking care of it and doing that. And so I've generally found

00:33:32.080 | that the thing that is like the cheap way of doing it, like spending tons of time on chat,

00:33:36.240 | GPT, researching all this stuff. Well, now I have the headache of having to like synthesize

00:33:40.160 | all of this stuff that I've found and convince my wife. Cause it's like what I found and she

00:33:44.080 | didn't find it. And I just would have been better off buying the course and spending whatever it

00:33:48.480 | costs because it would have saved me so much time and so much stress. Yeah. So nothing makes me

00:33:52.240 | happier. And you are an example of this, of finding someone who's done all the research

00:33:56.080 | to come up with a bunch of, I'm not going to go research what my razors should be.

00:33:59.280 | I'm just going to take your list of razors and be like, I'm going to use this.

00:34:01.920 | That's how I feel about hacks with you. Yeah. So that's my, my, my gift is, uh,

00:34:06.880 | optimizing life. Yours is synthesizing. I guess it's kind of a similar thing. It's,

00:34:11.680 | you know, you've got business advice, personal advice. It's a different advice, just maybe not

00:34:16.240 | as focused on deals and travel and optimization. But when it comes to decisions, there was another

00:34:22.000 | one about rare opportunity. So I learned this one, this is an interesting one. Cause I heard

00:34:27.600 | this for the first time from the founders. Let's see the two of the three partners at the first

00:34:33.440 | firm that I worked at. And basically they were two younger guys who spun out from their prior

00:34:40.800 | firm with one of the founders of that prior firm to start a new one. And they were like 30 when

00:34:45.360 | they spun out and got to be co-founders of this new private equity fund. And I asked them how

00:34:49.280 | they thought about that decision. And the way that he said it was there are certain

00:34:54.960 | opportunities in life that you get on average zero to one time

00:35:00.000 | in your life. Like the average person gets zero to one. And so if you get, if you're one of the

00:35:06.480 | lucky people that gets that one chance, that one opportunity for this really rare opportunity,

00:35:11.040 | you have to jump at it. And he was like, starting your own private equity fund is an opportunity

00:35:16.320 | that you get zero to one times in your life. And so the fact that he was getting it, he was like,

00:35:19.840 | I have to go do this. Even though he was on the safe track doing really well at his prior firm.

00:35:24.080 | And I remember registering that as very, very interesting. And then when I was thinking about

00:35:28.080 | my own opportunity to go and kind of build this ecosystem and the thing that I was working on,

00:35:33.120 | it was a really key factor in me deciding to kind of go all in and do it because I felt like,

00:35:37.520 | okay, I might get one chance to do this unique thing while I'm on a growth curve and things are

00:35:42.400 | going well. And there's all this stuff happening in the world. Like this might be my one chance

00:35:46.640 | to go do the interesting thing. Because if I don't, then I'm going to have like all this gravity

00:35:50.560 | around what I've been doing and it's going to have built and we're going to have kids and it's

00:35:53.920 | going to be much more challenging. And so here's my like rare opportunity that has popped up

00:35:57.760 | and I need to just jump at it. And I think it is like a really good framework for thinking about

00:36:02.640 | those unique moments in life. Just like being able to pause, recognize when you're in that,

00:36:07.600 | like you're having that unique chance and to just sort of throw caution to the wind and jump at it.

00:36:12.960 | Yeah. And I think not overthinking the reasons not to do it. So I look back,

00:36:17.200 | I was in college and I won't go into the whole life story, but I didn't know what I wanted to do.

00:36:21.760 | I didn't even really realize that you were supposed to plan your job so far in advance.

00:36:25.840 | So I was like springing at the end, like I got to go get a job. I got to do this quickly.

00:36:29.520 | And I got an opportunity to work at an investment bank in New York called Allen & Company. Kind of

00:36:33.680 | like weird, small boutique bank. I knew it. But the only job they offered was an internship.

00:36:39.520 | And I was talking to friends that actually knew, like at the time I was like one month

00:36:43.360 | into even knowing what investment bank was. And I only went down that path because I asked my

00:36:47.520 | friends who were well more prepared and said, "What's the best job you can get out of college

00:36:50.800 | in American investment banking?" I was like, "Well, I guess I should do that. I don't know

00:36:53.120 | what I want to do." And they were like, "Allen & Company is like a very, it's not like one of

00:36:57.680 | the places you could just get a job." It was like, kind of had this mystique and allure.

00:37:01.520 | And I was like, "Do I take an internship at a company?" Not a full-time job, just an internship

00:37:06.720 | and see where it goes. But everyone was telling me like, "This is a rare opportunity. You don't

00:37:11.120 | usually get an offer from a company that's so secretive and cool."

00:37:14.320 | Especially when you don't know what investment banking is.

00:37:16.240 | Yeah. I mean, I had read my vault guide. I don't know if the vault guide still exists,

00:37:21.120 | but back then it was like, there was this book. It's like, "Read this and you understand the

00:37:24.080 | industry." So I took that. That was one. I feel like starting a podcast was one.

00:37:27.760 | There've been a handful of times where I've quit a job to go do a thing, or I don't know,

00:37:33.680 | we traveled around the world because we were like, "This is a window to do it." So I love that one.

00:37:37.840 | Yeah. It's just taking advantage.

00:37:40.240 | There was a Razor you had about regret minimization,

00:37:44.160 | and I'm curious, it didn't make it to your new list related to Bezos, not Gates, so sorry. But

00:37:51.520 | I'm curious if that's still something you think about.

00:37:53.280 | Yeah. I mean, the regret minimization framework, I think the first time Bezos talked about this

00:37:58.720 | was in an interview with Walter Isaacson. It might be like 1996, way, way back interview.

00:38:06.560 | Basically, we're super nerdy Bezos, not jacked out of his mind Bezos that we have today.

00:38:12.560 | Really nerdy Bezos is talking about how he made the decision to leave D.E. Shaw.

00:38:16.640 | This relates directly to the rare opportunity, by the way. Leave D.E. Shaw, which is this famous

00:38:21.840 | quant hedge fund where he was making tons of money, and on a very certain path to make tens

00:38:27.440 | of millions of dollars in his life. Amazing, amazing outcome in career, top 0.01% life.

00:38:33.920 | Leave that to go start a bookstore on the internet, which makes no sense. Again,

00:38:37.760 | crazy ideas going back to connect it to other Razors. His whole thing was zoom forward to the

00:38:44.160 | future. Think about your 80-year-old self looking back on this decision. Will you regret not doing

00:38:50.160 | it? If the answer is yes, then you should do it. That's what he did. He thought, "Well, I regret

00:38:56.080 | not taking this opportunity and going after this." The answer was yes, and so he left and started

00:39:01.440 | an Amazon, and now we all get packages in 24 hours from drones that are dropping them off.

00:39:05.680 | I think it's a brilliant general way of thinking about this. I've often thought about it as in

00:39:11.600 | both directions. You're like, "Okay, what would your 80-year-old self say about this decision?

00:39:16.800 | Also, what would your 10-year-old self say about this decision?" The reason I think that one's

00:39:20.880 | good is because your 80-year-old self really cares about the compounding of the decisions

00:39:25.920 | you make today and how any decision you're making today is going to compound into the future,

00:39:30.320 | but your 10-year-old self also reminds you to not take shit too seriously along the way.

00:39:34.560 | You're probably like this too. You're an optimizer. You're thinking through every

00:39:39.920 | decision. You're really thoughtful. You're constantly trying to get little bits of ROI

00:39:44.240 | out of everything you're doing. That's great. I think there's a lot of value that can be gleaned

00:39:47.840 | from that. At the same time, sometimes you just need to have some fun and not think about razors

00:39:53.040 | and not think about hacks and just go have a beer and sit on the couch and not take advantage of

00:39:58.000 | whatever time you're wasting by doing that. I think that that always helps. I call it the

00:40:04.160 | young and old test. It's like you think about the decision as a 10-year-old and as an 80-year-old

00:40:09.200 | and then meet in the middle. The Bezos thing, it ties directly to the rare opportunity.

00:40:15.280 | You have this one potential opportunity in your whole life to go do this thing and you should

00:40:20.880 | capitalize on it. To your point on making these decisions without thinking too much about them,

00:40:26.480 | I've often thought about that as a concept, which is big decisions, paradoxically, I find are better

00:40:34.000 | made quickly versus slowly. There's this desire when you have a big, big decision, you're like,

00:40:38.960 | "Okay, I'm going to sit down and make this big chart of pros and cons and spend all this time

00:40:42.720 | thinking through them." What I tend to find is that your instinct actually is usually pretty good.

00:40:47.120 | Sometimes you just need to open the door, jump out and hope you packed your parachute really well.

00:40:55.200 | I think it ends up making for much better outcomes. You don't waste so much time.

00:40:59.200 | I did an episode recently, I haven't aired it yet, where I had a performance coach come in and we

00:41:06.640 | picked a topic and we just recorded the session. The topic was I struggle so often of over

00:41:15.200 | optimizations. I have all these decisions to make. What he actually broke down through this

00:41:20.240 | interesting conversation using tactics that we later in the episode talked about the tactics

00:41:24.560 | he was using, was that a lot of times most decisions are made emotionally, but you don't

00:41:30.000 | think that in the moment. You might be talking about big decisions, you want to make your pro

00:41:35.520 | and con list, analyze everything. He's like, "You need to stop and not just reflect, but maybe get

00:41:42.160 | outside and force yourself into a different state because the emotional decision might actually be

00:41:46.800 | the easy way." He was basically trying to teach me that this thing that we often think of as our gut

00:41:52.320 | decision might actually be more of an emotional decision. We talked about this exact example I

00:41:57.280 | used about my wife in this course. He was like, "It was so easy for you to make that decision

00:42:01.280 | because you were thinking about it emotionally. You weren't in the middle of doing the research."

00:42:04.400 | My new thing is whenever I'm in the middle of trying to make a decision, big or small,

00:42:09.280 | I try to pause and then get myself out of the research phase. Not pause and look at my options,

00:42:16.320 | pause and look at my spreadsheet, but pause and go outside for 10 minutes and just think about

00:42:21.120 | what's the right decision here. Sometimes it just comes to you. It doesn't come to you when you're

00:42:26.160 | looking at the data. It comes to you when you think, "What would the right decision here be?"

00:42:30.000 | It's interesting. My reflection is just I've never made a single pro-con list that actually

00:42:36.320 | swayed my decision. I've never drawn... In a movie, they make the pro-con list and then they

00:42:41.680 | look at the list and the pros are like, "There's 30 of them," and the cons, there's three. You're

00:42:45.600 | like, "Oh, okay. It's clearly a pro," but that's never happened to me in real life.

00:42:49.840 | What ends up happening is I just sit there and stare at something that looks relatively balanced,

00:42:54.400 | and then you just end up making the decision anyway. It's not like it actually helped me

00:42:57.520 | think it through. I don't know. I go back and forth. I'm like you. I have all these frameworks

00:43:03.920 | and mental models and razors, but it's not like I'm sitting going through a checklist of them

00:43:08.160 | when I'm going and making decisions. It's again, things that are in your mental toolkit that you're

00:43:13.280 | generally thinking about. To go back to one, the optimist razor, it's not like I'm thinking like,

00:43:18.480 | "Okay, well, Chris invited me to do a podcast and Chris is an optimist, so I should... Okay,

00:43:23.280 | by this decision-making, I'm going to go spend time with Chris." It's just ways to live your

00:43:27.440 | life that you just generally are trying to be around optimists or whatever it is.

00:43:31.120 | I try to avoid being mechanical about how all this stuff gets implemented. It's just general

00:43:38.240 | rules and ideas that you have floating around your brain that you're applying to how you live

00:43:42.480 | life on a daily basis. Yeah, I really like that. I was thinking maybe you had the contacts sorted

00:43:48.320 | by optimist score. Yeah, yeah, yeah. Optimist score, Chris, 7.2. Okay, we're doing the podcast.

00:43:54.160 | Okay, so we're not going to spend all of our time optimizing every decision we make,

00:43:59.760 | going through these rubrics every time we do anything. Let's talk a little bit about how we

00:44:03.840 | spend our time and how we choose what to do with our time. One of the things I know you value is

00:44:10.240 | serendipity. Yeah, I have this concept of luck surface area that I've probably adapted from

00:44:18.880 | people that have talked about it over a period of time. The first time I ever heard serendipity,

00:44:25.280 | I think it was serendipity, I forget what he called it, was this guy, Tim Brown, who was the

00:44:31.120 | CEO of IDEO, the big design firm. He talked about the whole idea of engineered serendipity, that you

00:44:38.560 | could create luck. It was the first time I had ever heard of it. This was probably back in 2010

00:44:44.320 | or something like that. I was in college. It always stuck with me. I've recently been thinking

00:44:48.960 | about luck surface area, the whole idea that you can actually expand your surface area for having

00:44:54.000 | lucky things happen to you. How you do that is by, again, putting yourself out there. It's like,

00:45:01.040 | you don't get lucky sitting on the couch watching Netflix at home. You get lucky by being out,

00:45:06.080 | engaging with people, meeting new people, publishing your work, putting things out there

00:45:10.480 | into the world and seeing what can bounce off of it and the connections that can be made.

00:45:14.640 | My whole idea with the luck razor or with the serendipity razor is you should always try to

00:45:21.600 | expand your luck surface area. If you're going to choose two paths, a decision to make between

00:45:26.320 | staying in and watching Netflix on a given evening or going to that opportunity, the dinner, the

00:45:33.360 | meeting, the people, whatever it is, or to publish something publicly rather than to just have it

00:45:39.040 | sit in your journal, you should take the path that has the larger luck surface area. I think

00:45:43.360 | this applies mostly when you're trying to expand your luck surface area earlier in your life and

00:45:48.240 | in your career. Once you've done that, you've figured out where the ripest opportunities are,

00:45:52.800 | then you can start going deep and you can narrow it. For instance, today, I would probably choose

00:45:57.600 | to sit at home and relax and spend time with my wife and son rather than going out and about to

00:46:02.480 | some big event because I don't really feel like I'm trying to get lucky on things anymore. I've

00:46:06.240 | sort of figured out where my luck has come from, and now I'm just going down and digging deeper

00:46:10.800 | into that area, into that hole. Early on, expanding your luck surface area in any way, shape, or form

00:46:17.360 | early in your life and career, I think is important. I want to come back to how we do spend

00:46:22.240 | our time. Let's say you are going out and I'm going to tee up one other razor, which is there's

00:46:28.160 | two rooms. How do you pick which one to go to? The one where you're going to be the dumbest one

00:46:32.400 | in the room. Always, always. This is a common thing that people say. If you're the smartest

00:46:37.120 | person in the room, you're in the wrong room. I really do believe that. Putting yourself in

00:46:42.640 | uncomfortable positions where everyone is smarter than you tends to lead to really interesting

00:46:47.680 | things, especially when you pair it with some of the stuff we talked about earlier, like good ways

00:46:51.680 | to get those kind of people talking, good ways to think about how you can be valuable to them,

00:46:56.160 | how you can stick out in their minds, walking away from the conversation. Like you said,

00:47:00.000 | I like that one a lot. I'm going to steal that. Sending people books, etc. Just getting into

00:47:04.960 | rooms where you feel a little bit uncomfortable, that's where you end up having the most growth

00:47:09.200 | come. Yeah. I love just walking up to a table of people. I'm like, "I have no idea what you're

00:47:15.200 | talking about. Let me just listen." It's super uncomfortable. Yeah, it is super uncomfortable.

00:47:20.400 | And you could do it in a weird way. But in the right environment, I think it's wildly interesting.

00:47:26.800 | Yeah. I'm going to this event in Santa Barbara in a couple of weeks. And there's a lot of wildly

00:47:32.960 | successful people that it looks like are going to be there. And I literally don't know a single

00:47:36.960 | person. And today, I was like, "Man, it's going to be really hard to go and do this." Because I

00:47:43.520 | don't even have a wingman. I don't have a friend who's my guy that I can go around with or girl

00:47:48.080 | that I can go around with. I literally don't know anyone. And I feel like a total imposter going to

00:47:53.200 | this event. Because everyone is... CEOs are really, really impressive people. And I had to snap

00:48:00.960 | myself out of it and just say, "Oh, what a cool opportunity to just be in this room." You can

00:48:04.480 | just go listen to people and add value in some other way other than talking. So I'm excited for

00:48:10.320 | it now. What's your networking move when you're at an event like this? And you're like, "I don't

00:48:15.440 | know about you." Even though I love being around people, I get energy from people. I think my

00:48:19.200 | default is like, "Well, should I just go stand around here and check an email?" Even for someone

00:48:24.960 | who loves people, it can be a lot to just walk up to random people all day. Yeah. I try to find

00:48:31.600 | circles of people. I think I tend to just walk and push myself into a circle and listen a little

00:48:40.720 | bit to what people are saying. And then I honestly use that question a lot. "What's getting you

00:48:44.640 | excited these days?" I've been asking people, "What lights you up?" Because oftentimes, people

00:48:49.680 | will talk about their kids. They'll talk about their family. You end up getting to a more personal

00:48:53.120 | level than the same questions they constantly get asked. Like the CEO of United or something,

00:48:58.960 | an airline is going to be there. They probably constantly get asked about things about their

00:49:02.720 | business. Analysts are asking them those questions. Earnings are... All this random stuff.

00:49:06.880 | But if you ask them about their family or like, "Do you have any kids? What are you getting

00:49:11.280 | excited about?" It just opens the door to a much more interesting connection that you can make with

00:49:16.080 | those kinds of people. And then you become interesting to the whole circle of people

00:49:20.640 | because you're the one that's driving those things forward. Because at the end of the day,

00:49:24.400 | everyone feels awkward in those things. I don't know a single person that goes to a big networking

00:49:29.200 | gala dinner or whatever and walks in and is like, "Oh, I feel great. This is amazing. This is my

00:49:35.040 | favorite thing in the world." Those things suck. Nobody likes that. And it's the reason most people

00:49:39.040 | end up drinking at those things is to loosen up a little bit. So I just think having a go-to move

00:49:45.040 | of how you insert yourself and talk to people. And honestly, just not caring if you feel a little

00:49:50.880 | embarrassed. Yeah. Earlier in my career, I learned something. I wish I remembered who it was from.

00:49:55.760 | But most of these events, especially when not everyone's the CEO and it's obvious what they do,

00:50:00.400 | the opener question is always like, "Oh, what do you do?" And I picked up from someone the

00:50:06.080 | idea of just opening with, "What's your story?" I don't know if I like it more than asking what

00:50:13.120 | someone's excited about right now, because then you get more energy. But if you're sitting at an

00:50:17.920 | event, you're trying to figure out, "Well, who are these people?" Because maybe you are trying

00:50:20.800 | to do some networking. You're trying to figure out who you need to spend your time with. What's

00:50:25.040 | your story is just a much better opener, especially when you're around people that maybe are in

00:50:30.960 | between jobs and it's super awkward to be like, "What do you do?" It's like, "Well, I don't have

00:50:34.320 | a job right now." Yeah. And if you know them, if they are someone that everybody knows,

00:50:38.720 | and you know what their story is, and they know that everybody knows them,

00:50:41.920 | I've always found that just telling someone that you admire something that they've done

00:50:46.320 | is a great, great opener. No one is immune to flattery. And people love to know that people

00:50:51.040 | have recognized things that they've done. Bill Gates, when I first said hello to him,

00:50:54.640 | I just told him I admired his philanthropic work in the developing world, because I really do.

00:50:58.800 | I've seen a lot of impact from it. My family's from India, and they do a lot of work there.

00:51:04.080 | And that's not something that he typically gets told, probably. It's all about Microsoft,

00:51:08.560 | or all about being a mega billionaire, or whatever it is. And so, it jumps out immediately. And no

00:51:13.520 | one will look at you and be like, "Shut up," when you say something nice to them about things that

00:51:18.560 | they've done. So, I also just find that that's a nice little way to get an entry point to a

00:51:24.880 | conversation. And while I don't think that the best thing to do is try to be the person who's

00:51:29.440 | jumping in and talking all the time, we already covered that. I will say, if you can find a

00:51:33.360 | question to ask someone about what they're excited about in that realm, but that ties

00:51:37.360 | into something that you have some unique expertise in, or I think we all probably know the topic that

00:51:43.840 | maybe lights up the room when you talk about, I wouldn't try to just jump in and have that.

00:51:48.400 | But if you could steer the conversation towards a place where something that you're uniquely

00:51:53.200 | knowledgeable about. So, it just made me- Hey, were you guys talking about Twitter threads?

00:51:56.480 | Were you guys just talking about Twitter threads? Well, for me, this idea came to me when you're

00:52:02.560 | like, "What are you excited about?" I was like, "Oh, are you taking any exciting trips this year?"

00:52:05.840 | Almost everyone has a trip in the next 12 months. It's like, I could steer the conversation towards

00:52:11.280 | something related to travel. That would be something where I'd be like, "I probably have

00:52:15.040 | some interesting hacks or tips to the average audience." But in a way that gets them to take

00:52:20.960 | it there in a way that they're excited about. That's a very good idea. It's like shepherding

00:52:24.800 | them. You're like the river god guiding them. I like that a lot. That's smart.

00:52:29.520 | But I want to come back finally to where we spend our time. And you have a Time Billionaire Razor,

00:52:34.240 | but you actually did a really great post about this and looked at some data on how we spend time.

00:52:38.640 | So, maybe let's end talking about how we spend our time and how that's evolved for you.

00:52:42.480 | Yeah. I mean, this is a topic that's very near and dear to my heart. You have young kids.

00:52:46.320 | I guess by the time this comes out, he will be one. And I have thought about time more in the

00:52:55.600 | last year than I had in my entire life. Part of that is because when you have a young kid,

00:53:02.400 | you all of a sudden start measuring time in weeks and months, which you never really do

00:53:08.800 | otherwise. People ask you how old the kid is and you say like six weeks or nine weeks or 12 weeks,

00:53:12.960 | whatever. I've never thought about the passage of weeks as a passage of time. In the past,

00:53:17.360 | it's just like another week. A lot of people have now seen that life calendar,

00:53:21.840 | like Memento Mori calendar, where it's 52 rows across and it's 80 rows down. So,

00:53:26.960 | it represents your entire life. Every row is a year and the 80 rows is your life and you fill

00:53:32.720 | in black every week that goes by. So, you can literally see the passage of your life, passage

00:53:36.720 | of time. So, I've been thinking about this stuff more and more over the course of the last year.

00:53:41.840 | And I came across this American Time Use Survey data set that I think it was Our World and Data

00:53:49.120 | kind of crunched together to look at how we spend time over the course of our lives and specifically

00:53:53.840 | who we spend it with. And I saw it, they had kind of combined it into a single chart of all these

00:54:00.960 | lines, like how much time you spend with your children, how much time you spend with your

00:54:04.480 | parents, how much time you spend with friends, coworkers, alone, etc. I went in and downloaded

00:54:10.240 | the data and split it out into individual charts that you could really see like each line and kind

00:54:14.640 | of the curvature of each line. And it was an unbelievably powerful image when you look at

00:54:20.800 | them individually because you really get a feel for like, especially with kids, how you basically

00:54:26.160 | spend all of your time with them during this very short window of their life and then it falls off

00:54:31.760 | a cliff. And the reverse of that is with your parents, you spend almost all of your time with

00:54:36.880 | them over the first 18 years of your life and then it just goes like this and you're not spending time

00:54:41.520 | for the rest of your life. And so it just brought to the fore all of these really difficult

00:54:47.760 | conversations, but also sort of empowering ones for who you spend your time with, who you want

00:54:53.200 | to be spending your time with and how you want to sort of change the curves as it were over the

00:54:58.400 | course of your life. And so have you made changes in the last year as a result of thinking about

00:55:04.080 | this? Yeah. I mean, the biggest change we made was in May 2021 where we picked up our life and

00:55:09.280 | sold our house in California, bought a house in New York and moved to be closer to my parents and

00:55:14.640 | to my wife's parents. And that was based on the initial realization of how little time we had

00:55:19.840 | left with our parents. Not because they're particularly old or sick, knock on wood,

00:55:23.920 | but just based on math and their age, our age, how often we were seeing them about once a year.

00:55:29.920 | And now I see my parents at least a few times a month. They're like a big, big part of my son's

00:55:35.360 | life, similar with my wife's parents. They're constantly around. And it makes a huge difference.

00:55:40.960 | And it makes them so happy too, to be a part of our lives, to be a part of our son's life.

00:55:45.040 | So that was a huge, a huge life change. And then the kids one is the biggest for me in terms of

00:55:50.320 | what it's done in the last year. I mean, I think it's this friend of mine, Kay, he, who has talked

00:55:56.800 | about the magic, the magic window, I think he calls it, or the magic years, which is like this

00:56:00.960 | 10 year period of time where you are your kid's favorite person in the world.

00:56:05.360 | And once they're older than 10, there are other people that fill that role. They have best

00:56:10.240 | friends. They have girlfriends, boyfriends, they get married. They're going to have kids,

00:56:13.760 | like they're going to go on and live their entire life where you as their parent are not really the,

00:56:18.320 | like the central figure and actor. But during this 10 year window, you are, and they love you more

00:56:24.400 | than anyone else in the world. Yet we live in a culture where traditionally those are the years

00:56:28.800 | where you're also working the most and like trying to make the most of your life and of your career.

00:56:32.400 | We were talking about this earlier, like your life is really good, but you also want more,

00:56:36.800 | you know, from your career, from businesses you're building. How do you balance those two?

00:56:40.800 | Because anything you decide to do or take on is a direct trade-off of time with your kids.

00:56:46.000 | You're going to be like, if you're going to be grinding on some business or project or working,

00:56:50.160 | that's just time away that you could be spending with them. And so how do you figure out and find

00:56:54.400 | the balance of that? I've been thinking about that more and more and more. And being home during

00:57:00.720 | this, like first year of my kid's life and getting to spend tons of time with him and really build a

00:57:04.720 | bond with him is meaningful to me. And so does that mean saying no to a lot more professional

00:57:10.960 | things? I mean, like I say no to 99% of opportunities that come my way. And now,

00:57:15.440 | 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

00:57:21.840 | of stuff and a lot of financial things that I'm just turning down, you know, out of hand.

00:57:25.840 | And for me, that's been a conscious decision of, I don't actually particularly find myself

00:57:30.640 | motivated by money all that much. So I actually don't feel like I need much more money than I

00:57:34.320 | have today. And we have a great house and we like our life a lot and we're happy and we have, you

00:57:39.760 | know, like I have tons of time at home and free time with my son. And I actually wouldn't change

00:57:44.800 | that much. Like if you offered to pay me today, you know, $50 million to work 80 hours a week

00:57:50.240 | this year, I would not do it. Full stop, like wouldn't even consider it. And that's a pretty

00:57:54.880 | empowering feeling when you realize priorities and the trade-offs. But that, I mean, to me,

00:58:01.200 | just like really being ruthless about what my North Star is and what I want to focus on has been

00:58:08.160 | a pretty liberating thing and a really meaningful thing for me.

00:58:13.280 | What do you think has helped you not want to play Keeping Up With The Joneses, which I feel like

00:58:18.560 | many of our peers are still feeling that? I think the biggest thing is avoiding the like

00:58:25.680 | when then psychology around this stuff. I saw a great clip of Dax Shepard recently talking about

00:58:31.040 | this and how he had all of the trappings that he thought were going to make him happy and successful.

00:58:36.000 | And he had convinced himself all on the way that like, well, when that thing happened,

00:58:39.200 | then I'm going to be happy and this'll be great. And then he got that and he realized he was like

00:58:43.840 | suicidal and not happy at all. And so it was really liberating that on the back end of getting

00:58:48.480 | healed and treated for all of that to realize, "Oh, those external things aren't actually going

00:58:52.880 | to ever make me happy." He saw it really viscerally. Most people never have that.

00:58:56.400 | You don't realize that all of those games you're playing in your mind, like, "Well,

00:59:00.240 | when I get to vice president or whatever, then I'll be happy because I'm going to be

00:59:03.920 | making all this more money." Or, "When I get a million followers on whatever platform,

00:59:08.560 | then I'm going to be really happy. I'm going to have made it. Things are going to be good."

00:59:11.440 | The reality is if you're looking for something external to be what creates your internal

00:59:16.240 | happiness, it's never going to work out. Happiness is full-on inside job. You have to be finding

00:59:21.840 | happiness from something that is a deeper meaning, deeper purpose, something internal. It can't be

00:59:27.040 | some external achievement because it just doesn't last. You just revert to whatever the next when is

00:59:32.080 | that you're going to create. For me personally, I've realized that. I stepped off the treadmill

00:59:38.480 | around all those things. That doesn't mean that I don't want more because I am motivated by growth,

00:59:43.360 | but the growth is an internal thing versus an external thing.

00:59:47.120 | It's not, "Hey, I want to make X dollars or do this or that." It's like, "I want to feel like

00:59:53.360 | I'm getting better at things. If that's getting better at being a dad, that's great. If that's

00:59:57.040 | getting better at running because I'm really into running right now, then that's great."

01:00:00.960 | But it's not, "I want to get a better house. I want to get a better car. That guy got this,

01:00:07.200 | so I want to do that." It's just turned everything internal in a much deeper way.

01:00:12.880 | Yeah. The way I describe it for me is I want to feel pulled into things instead of pushed

01:00:16.720 | into things now. I had a friend who was like, "I want to start a company." I was like, "Why do

01:00:20.400 | you want to start a company? You started a company. You've done this. You've been successful."

01:00:23.840 | The more he thought about it, he was like, "Well, I feel like I don't know what I want to do." I was

01:00:28.400 | like, "Just wait until there's a thing that's pulling you towards it instead of trying to push

01:00:33.040 | yourself into it." That's what I try to look for, which is ultimately why I left. I was like,

01:00:37.840 | "I just feel that I have to go do this full-time." Yeah.

01:00:41.280 | The other way to think about it is, again, I think this is from Tim Ferriss.

01:00:45.840 | He has this question of, "What am I saying no to by saying yes to this?" I think about that

01:00:50.880 | constantly in the context of family and in the context of what my priorities are. If my son is

01:00:56.960 | my number one priority in the world right now and building a deep relationship with him over this

01:01:02.800 | next 10 years and really, really having that closeness and that bond, anytime some new

01:01:09.840 | opportunity comes along, I have to think that question through and think about, "Okay, what am

01:01:13.440 | I saying no to with him by saying yes to this?" If some new travel comes up, someone wants me to go

01:01:18.960 | and speak at something and it's going to require me being gone for a few weeks, what am I going to

01:01:22.400 | miss? What am I going to be saying no to? It might be $50,000 that someone wants me to come speak at

01:01:28.240 | something and they're going to pay and it's going to be this cool trip and I'm going to get to go

01:01:31.040 | to this cool place, but if I'm missing his birthday party, hell no. There's no amount of money you

01:01:37.920 | could pay me, right? Really thinking that through and it might not be kids. Maybe it's something

01:01:42.480 | else. Maybe it's time with your family. Maybe it's some hobby that you really enjoy or a trip

01:01:47.760 | with friends that you really wanted to take that you're going to have to say no to because of some

01:01:52.000 | new work thing that you're going to really have to dive into if you get the opportunity. Thinking

01:01:56.240 | through those trade-offs I think is a really healthy thing to do, but it requires you to sit

01:02:01.520 | back and figure out what your priorities are. What are the core ways that you're going to measure

01:02:06.400 | success of your life at the end of the day? Yeah, I mean that could be a whole other episode,

01:02:10.080 | so we're not going to go down that path, but I will say that my hack here is I took a lot of

01:02:14.480 | time to craft what I thought was like my perfect no email and then I made it a snippet so that I

01:02:20.800 | could just fire it off anytime and someone's like, "Hey, I really want to talk about this thing,"

01:02:24.240 | and I'm like, "I'm heads down. I should probably just publish it because people could steal it."

01:02:28.960 | It's like I'm really heads down focusing on stuff that's important. Feel free to shoot me an email,

01:02:33.680 | but not going to have time to meet. Really appreciate you reaching out. It means a lot.

01:02:37.360 | Yeah, I do the same. By making it easy, I use it so much more. Honestly, the difference between

01:02:45.440 | thinking about it and having it as a keyboard shortcut level ease makes me send it so often

01:02:51.760 | and feel okay about it. I got this, I think it was from Cal Newport. No, it was from Derek Sivers,

01:02:57.840 | who was like, "If you're always busy and you can never meet with anyone, you're kind of projecting

01:03:02.560 | that you can't prioritize your own time. And if you leave free time in your calendar, you're able

01:03:08.160 | to take advantage of things when they happen that are really interesting." And so I'm trying to live

01:03:13.280 | by that. It's hard because especially when you're younger, it's like every opportunity could be more

01:03:17.920 | serendipity, more serendipity. But I feel like as we have families and we kind of understand our

01:03:23.120 | areas, you've got to really do it. So I appreciate you saying yes to this because there's always so

01:03:29.200 | much knowledge that gets dropped doing it. Where do you want to send people today who are listening

01:03:36.720 | and want to stay on top of what you're doing and learn more? I guess my newsletter is probably the

01:03:40.880 | best. You can find it at sahilbloom.com, just my name. I guess sahilbloom.com/newsletter takes

01:03:46.800 | you straight to the newsletter. But everything's on my website. And then I'm on all social platforms

01:03:53.040 | at Sahil Bloom. The virtue of having a weird name is you get your own handle.

01:03:57.440 | Kind messages only. No need for snarky.

01:03:59.200 | Kind messages only if you send me the mean ones. I won't reply, but I will feel empathy for you.

01:04:03.120 | Amazing. Thank you so much for being here.

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