(upbeat music) - 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, 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 are all sort of razors in their own way, shape, or form, like ways to make a decision, cut through things, you know, 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.

- Yeah. - 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, oh, I got 17 razors to use in my life. I did try to bulk them into a couple categories 'cause 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. 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. Like the, 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, you know, who do you want? Like, 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, and they have a whole 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. - 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, 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, like, you're 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, like, Harvard Medical School credentialed surgeon, like, perfect, clean cut, everything's good.

And then the other one looks like a butcher. Like, he's got blood all over him. Like, he just doesn't look the part. He's like big, you know, big hands, whatever, like, big beard, scraggly. And his whole thing is that most people pick the, like, 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 that was, like, another interesting way of thinking about who to work with because we do have all of these little, like, 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 gonna 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 gonna put, like, a little bit of skin into the game no matter what. Even if I'm not gonna 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 the 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 wanna have, you know, your, like, coder and engineer friends maybe, like, weighing in on, like, culture and fashion and being like, oh, I'm gonna 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 trying to understand more because it might be like an asymmetric bet on the future.