Cody (2:08)

It's so funny you say that. I was at this YouTube thing this week, and so I have top of mind. But one of the creators there, I think it was Mark Rober, who has like a huge science YouTube channel. And he did something with like the Discovery Channel or another science Channel. And so the, you know, CEO of YouTube was joking with them and he was like, yeah, you know, it was really nice of you to do that thing with Discovery Channel. It's incredible to collab with a smaller channel because their viewership's like 10x smaller than Mark Rober's on YouTube. And so it's interesting. Like this idea of capital, code and media. How do you judge whether you have those kinds of leverage or you don't?

Patrick O'Shaughnessy (2:46)

If you're a normal person, ideally, you want your earnings, your inputs and your outputs to be separate from each other. You don't want to have to work an hour to earn, you know, 10 bucks or 100 bucks or 1,000 bucks. You want to earn independent of your input. If you're in a normal job, your linear inputs and outputs. If you are working on a podcast, like you record the same podcast, you publish it, whether a hundred people listen to it or a hundred thousand people listen to it, you put the same amount in, but you get an unbelievably higher reward for doing the same amount of work. If you're investing in a company, like whether you invest $100,000 or a million dollars, it's the same decision, but the rewards for doing it are an order of magnitude higher. So you want to look for these places where your inputs and your outputs are uncorrelated. And the more levered you are, the bigger that difference is going to be. And the way you get leverage is by winning a smaller leverage game. So start small and just let those things accrue incrementally. Like we talked about Elon Musk, he's like the most leveraged person alive. And it's because people choose to give him capital. People choose to go work for him. People choose to support his companies and invest in him. And they do that because they trust his judgment. They trust that he's going to use that well and give them good rewards for doing so.

Cody (4:02)

Yeah. So interesting, because in today's age, it's even more normal, like it used to be. Maybe even like 30 years ago. I would say most people had none of these. Right? You had no money, capital, you had no code, you weren't an engineer, and you had no media because you weren't CNN. So it was like unless you were a top 10% or 1% in any of these three, you had zero. But now everybody could actually have all three really easily. So you could literally just ask yourself, am I making money? And thus am I taking my money and investing in other things. That's leverage. Can I code? No. But now I've got all these AI tools, so I can now use code. That's leverage. And media. Do I own cnn? No. But I actually have a podcast or I have an email newsletter or I have an Instagram account that I talk about. And so yeah, I actually am levered with all three and then it's degrees of them. But it's a wild time to be alive because for the first time ever, any human really, at least in, you know, most established worlds, can have all three of them for almost a zero dollar cost. Except capital.

Patrick O'Shaughnessy (5:05)

Yeah. If you can get a device that can get on the Internet, like you can enter the global meritocracy essentially. And like, most people aren't even trying. Most people are just on the consumption side. And so if you do, if you start creating, if you start coding, if you start trying to build products, like, and you think about it in terms of where do you get those uncorrelated inputs versus outputs and try to build a business, that's where you're going to get those exponential returns. And this true in every industry. Right. Like, I think people, you know, running a plumbing company would probably say, like, yeah, that's all well and good for a podcaster or a hedge fund, but like I run a plumbing company. Every business is just their growth is determined by how levered they are and how elegant they are and how long those levers can get. And Naval has a great. It's a long thing. I won't take you all the way through it. But he has goes step by step all the way through the real estate industry where, you know, you could be a day laborer working on a house, you could be a general contractor, you could be a real estate investor, you could be a developer of big properties, or you could take the final leap into like maximum leverage of external investors and technologists and everything and build Zillow. Right. And so the difference between a day labor and Zillow is just like how leveraged are you and how comfortable are you using each of those different forms of leverage.

Cody (6:23)

It's a really good point. I actually haven't thought of that before. It'd be interesting to put names on the tiers, you know, because every industry Actually has that. Everyone has the day labor all the way to the CEO, to the like level of CEO of what kind of company you are, to investor, to, like, I don't know, capital allocator plus risk taker. So it's actually an interesting way to think about the world. I think a lot of times people just think, am I entry level? How much do I make? But they don't think about what is the game the company that they're in is playing too. And I feel like Naval's the king of contextual awareness, like, you know, understanding the game that you're playing.

Patrick O'Shaughnessy (7:00)

It would be a fun game book to build of just breaking down the business from the beginning, all the way up the whole ladder. Because we hear these incredible stories of people who entered as a dishwasher in the restaurant industry and over the course of their career built a 50 restaurant chain. And those are people who just sort of figured out, what does the person above me know that I don't know? What tool do they know how to use? What were they able to access? How can I figure it out? How can I take that next step, that next risk, and climb all the way up the ladder?

Cody (7:32)

Naval talks about something that is kind of controversial these days. He says hard work is overrated and judgment is underrated. What do you think he means by that?

Patrick O'Shaughnessy (7:41)

I think the Archimedes quote, give me a lever long enough and a place to stand, and I can move the world. One totally correct decision can dominate everything. And Naval is really an elegant thinker. I think he's really enamored with the idea of where can you flick one domino and everything takes care of itself, which is this incredibly kind of like Zen business thing. What's the smallest action I can take to create the biggest result? It's very different than somebody like Elon or Goggins or whatever who are just kind of like trying to get the most out of themselves possible. But I think that's a really interesting approach. It's a good tool for thought to just be like, yeah, how easy could this be? He describes himself as lazy, which I don't think he is. But he's like, you know, I just want. I want the greatest reward for my effort. And I don't want to expend effort wastefully.

Cody (8:32)

Yeah, there is something to this idea of how do you become incredibly ambitious while also being lazy and lazy in the things that you will allow to take up your time? Because if you are crazy particular about the things that take up your time, then you have time to Figure out where to flick that domino that's gonna live rent free in my mind. Actually, you could spend a lot of time in the middle of and you will never actually have the full effect than if you spent the time to find the beginning.

Patrick O'Shaughnessy (9:03)

The real thing is hard work has a limit. Eventually you can't work 100 hour weeks forever. Hard work is respectable and admired. And yes, we should work hard. But hard work can only get you a 2 or 3x improvement in what you're doing. And if you don't learn to improve how you're working or the elegance or improve your leverage, like learn where you can have those hundred x where one hour of work or ten hours of work can have a 10x or 100x impact. Like you're going to be kind of stuck in that 2-3x improvement window no matter what you do.

Cody (9:37)

I think the part that then becomes hard. So then you're like, okay, that makes sense. Of course I'd want to find the fulcrum, or of course I'd wish to find the first place to flick the domino. But then the question becomes, how do you know? And like, Naval has great sort of critical thinking frameworks, but what does he mean by live like a lion?

Patrick O'Shaughnessy (9:56)

If you go see a lion on safari, like, they're just chilling most of the time, like 30, 45 hours at a time. They're just laying there and sleeping and kind of whatever. And then when they are both hungry and see prey, they leap into action like maximum adrenaline, full sprint, unbelievable violence and attack and take down this thing and have an incredible feast and then just lay there and sleep again for like 30 hours. And I think Naval sort of learned wisdom is that this is how he now approaches projects. Like, he'll see an opportunity, see an investment, just kind of be like reading and casually working, learning, going about his life. And then an opportunity will arise or a person will make themselves known as kind of like, all right, we all leap into action. We got to have a sprint, we got to start a company, we got to make an investment, we got to get up to speed on this really, really quickly. But if you were mired in something else, just like plodding along on not the biggest opportunity, rather than having the space to jump on the best opportunity when it came about, then you might miss it. And that's the live like a lion kind of mindset, is like you want to have the space to evaluate and attack the most important thing at any time.

Cody (11:06)

You know, it's interesting you talk about that because one of the things I've been obsessed with lately is people sitting in meetings that they shouldn't be in. And it's a big phenomenon. And you know, my team will all sort of chuckle about this because I will often say, like, you guys don't have anything to do in here. Why are you still in here? But what I haven't gotten to yet is where they self select to leave the meeting because there's so much social normative behavior of just, no, no, I'm supposed to be here from this time to this time, and I'm paying attention. And I'm sitting here and it's like, why are we being such good little girls and boys? Instead you really should be saying, you pay me and we are here to do this mission. And if I am sitting here doing this thing that is not top priority, I'm actually wasting your time, our money, our mission, all of it. But somehow we've all become like, way too politically correct to say anything like that. And so we just sit in meetings that we know are a waste of time, we tell nobody, and we think that's normal and that a CEO might like it.

Patrick O'Shaughnessy (12:03)

I feel like there's probably two types of person in that meeting. One is like, this looks like work and it's the easiest thing I can do today. So I'm just gonna sit in here and like, I'm gonna be in a meeting, I'm doing my job with the lowest effort possible. And then there's somebody else who's like sitting there and their skin is crawling because they're like, I hate this. I'm useless. I feel like I can't leave. I've got more important work to do. Like, please let me out of here.

Cody (12:24)

Yeah.

Patrick O'Shaughnessy (12:25)

But both are caught in the. Like, if you make the first step of the meeting, like, what is the point of this meeting and who belongs in it? Like, who has a hand in the solution that we're trying to arrive at and spend the first five minutes of a meeting on that and make it a cultural norm to dismiss people from meetings that are not. Like, I don't have a good case for being here and great, I want to be somewhere else.

Cody (12:44)

Yeah. It seems like such a no brainer, but I think off, even at our company where I'd say people say this to people, that I don't think we've done a good enough job giving them permission.

Patrick O'Shaughnessy (12:52)

Yeah.

Cody (12:53)

To beat it. You know, if they're like, cody, I don't think this meeting is relevant to me. I don't think I'VE ever gotten mad at anybody for that, but. Yeah, right, right. Get out of here.

Patrick O'Shaughnessy (12:59)

Yeah. There's a dynamic where people I think, want to be in the same room as like the. The person, the CEO, the leader, the whatever. Like that. Those meetings are an opportunity for FaceTime, probably in some ways that are like more about the political game than the output.

Cody (13:12)

I've actually never thought about that. That's a very good point. I think it's another screen that happens. Like the more successful you get, the more you forget that your presence can have negative or positive effects. Like when you give feedback, sometimes you have to be careful at which levels of the game because it can just ruin somebody. Or simultaneously, they want to hang out with you more, even though you're like, I would like you so much more if you didn't. Do I have to sort of say that too? I actually. It's kind of like an interesting idea because this goes back to authenticity. But there's a quote that I found originally from. You find what feels like play to you, but looks like work to others. You're going to out compete them because you're going to do it effortlessly. To you, it's art, it's joy, it's flow. You escape competition through authenticity. If I had to summarize how to be successful in life, I would just say two words. Productize yourself. Tell me more about that. And what does that even mean? To productize yourself?

Patrick O'Shaughnessy (14:03)

Yeah, I mean that is the two word summary of half of the book, which is like very difficult to fully unpack. But the ability to really understand and observe in yourself what you want to do naturally. You're ikigai or whatever. And one way to do that is to look at the things that you did as a kid, like when you were like 10, 12. Ask your family, ask your friends, what are the things that you were naturally drawn to? What are the things that you do in spare time? What are the things that you do even though nobody's paying you to do it? Or what's the 10% of your job that you like, really, really love and find yourself doing it more than you should? Like, these are all maybe signs that you're sort of drawn to do a particular thing. And I've experienced this in my life, is like the stuff that you do for fun or without expectation of reward is sometimes turns out to be the most rewarding thing.

Cody (14:55)

This book, you didn't even make money on this, really. Right. Didn't you give away most of the money from this book?

Patrick O'Shaughnessy (15:01)

I give away. We've given away, like, 5 million copies of this book, but we've also sold, like, millions. So I have made a lot of money. But when I. When I wrote it, I fully expected, like, a thousand people to buy this thing. I thought it was going to be a passion project for naval nerds like me that would never make any money, but I would have learned a lot by doing it. And I did learn a lot by doing it. And I'm still, like, completely shocked that people of all ages and races and countries and languages are, like, reading this thing and finding. Revisiting it and finding joy in it. And I'm like, I'm delighted by it. I think it's just a testament to how far reaching some of the principles that naval puts forward are.

Cody (15:40)

Yeah. What about this idea of. He talks about in the book? No one is going to beat you at being you and specific knowledge and how important it is that you have specific knowledge in what you're doing. What does that mean? And if somebody is struggling to figure out what they should. Should do, how do they figure out if they have specific knowledge?

Patrick O'Shaughnessy (16:01)

I think, I mean, the word should is the thing that he talks about of, like, there is no shoulds. But it's so hard to train yourself out of that. Right? Like, we spend the first 20 years of our lives sitting in classrooms, all being taught the same thing and being assessed on the same thing. And so then we go out into the work world and we're sort of like, all right, what's the job? What am I told to do? And what you find in successful people is that they're rewarded to the degree that they are unique and authentic and excellent. Actually, they're rewarded to the degree that they're unique and excellent. And that is usually downstream of them being authentic. Right. Like, your business works because you have fun being you, and you're authentically interested in all these concepts and building businesses and buying businesses. You buy crazy stuff all the time, and you have so much fun telling everybody about it. And I don't know how many of them work out, but it doesn't matter because it's all fun to watch, right? Like, or watching you, like, buy vacant land in Texas, abandoned land in Texas at an auction or something. I was like, that's just cool. And you're clearly just having fun doing it. And for whatever reason, I'm sure it'll be a nightmare for plenty of people. But I have fun spending thousands of hours breaking down very specific, useful ideas and articulating them and finding supporting arguments for Them and putting them all together in this thread that helps me remember it and helps other people identify with it. These are examples of specific knowledge that are outcomes of just how we chose to live. And we just continued to do things that felt authentic and unique to us and people responded to it and we sort of iterated through like, all right, I had fun doing that and the world enjoyed it. So I'm going to do it again and I'm going to do it in a new way and I want to continue it like. And we both ended up in unique careers that would have been very difficult to predict or define ahead of time. There were no blueprints for, you know, this is not an existing genre. Like, your particular combination of businesses is not one that there's a ton of historical precedent for. It's not like you set out to say, I'm going to build a real estate brokerage and I'm going to do it using all the best practices of real estate brokerage, right? Like this combination of media and capital is like new and emerging and dynamic and everybody's kind of doing it in a new way. So I think that mixture of like, authenticity and excellence, like, be yourself, do it to the best degree you possibly can, and specific knowledge will sort of come downstream of that. I know you Bill Gurley on and he's like, you know, become this incredible student of your, your industry. And if you set 10 people down and said like, all right, you are all going to go study the history of venture capital, great venture capitalists, those 10 people are going to study different things, are going to make different branching decisions all the way down. And one might become an expert in the history of biotech or green tech or fintech. Like, those people will make authentic human decisions. That makes them ever more unique. And one of my, like the degree that you specialize, even if you set out to be a generalist, you will end up becoming a specialist. A sufficiently advanced generalist becomes a unique specialist. And you should aspire to be a unique combination of authentic traits performed to excellence. And those are the careers that you are going to enjoy and products that are going to end up being unique.

Cody (19:09)

Such a good point. I mean, Scott Adams talks about the skill stack, right? Which really is a lot of what Naval talks about too. I think in different ways he would say specific knowledge and Scott Adams would say skill stack. And then he would talk about how you could either go become Michael phelps and do 10,000 or really 100,000 hours in order to become Michael Phelps, or just do hundreds of Hours at totally disparate tasks that when you stack them together, create an unfair advantage. And so I think that's super interesting. I want to circle back to this idea on shoulds because you have very interesting takes on it. You've caught me twice on it. And naval is very aggressive on shoulds, too. Like, do you believe in the word should? Does naval Ravikant believe in the word should? And how should we speak to ourselves?

Patrick O'Shaughnessy (19:54)

So should is one of those words that just indicates to you that you might be feeling more of an obligation than an interest in something. And so you hear people talk about, like, I should go work out. Like, yeah, but also your relationship to that thing is now, like, I don't want to. And the voice in my head is telling me that I have to. And the common thing is, like, I get to work out. So just like, change your phrasing about, you know, you have the opportunity to go do this thing that you want to do. There's a bunch of funny, like, little reveals in language that, like, when you're paying attention to people's relationships with things that's in there. But, like, I should go to work. I should, you know, follow in my family's footsteps. I should pursue this opportunity. Like, we all have those, and it just listening for them. Yes. It's either an obligation or an imposition from some version of yourself that you don't necessarily agree with or some external voice that is like, speaking to you more loudly than your inner voice.

Cody (20:54)

Yeah, it's really good. I mean, he talks about. He has like, a pretty brutal heuristic about if you're faced with a difficult choice, you should do. Gosh dang it. Can't even say the word choice. But if you're faced with a brutal choice and there's not an obvious one, then don't do either. Like, what would he say about when to do something or when not to do something?

Patrick O'Shaughnessy (21:16)

There's one from his personal trainer, which is hard choices, easy life. Which in the short term, if you take the hard path, you will sort of naturally bias. You'll come up with an excuse not to work out. You'll come up with an excuse not to have the hard conversation. And so if you find yourself in that position where there's something hard to do and there's something easy to do, if you just become good at making yourself do the hard thing, your life will become better as a result. There's probably something magical that's on the other side of something you're avoiding. And if you just Build a habit of tackling that. A lot of problems will take care of themselves. That's one. Paul Graham has a similar thing competitively, which is just like, run upstairs. If you're fighting a big company, do something really hard that they're going to find it very difficult to imitate.

Cody (22:04)

Yeah, that's a great point. Especially as the world gets less and less moated. Like it feels like every year actually, there's more and more opportunity to do things in business. You know, you used to have to have a ton of capital to launch a media company and now you have to have none. You used to actually have to have a lot of money to invest in startups. Now because evangelists, you could have a very small amount. Like everything has gotten kind of progressively easier in society or I guess easier to access in society. And so if you don't do the hard thing that is hard today, well, you know, you're definitely not gonna make it next year because that thing that's hard today will probably be even easier next year. So it's a good way. We say here at our company, one of our slogans is choose your hard. And so like, no matter what, anything in life is going to be hard. Being employed is hard. Being an owner is hard. Choose your heart. One of them is going to have a better outcome than the other.

Patrick O'Shaughnessy (22:52)

Working out is hard. Being fat is hard.

Cody (22:54)

Yeah, you got to choose one.

Patrick O'Shaughnessy (22:55)

Yeah.

Cody (22:55)

And you know, he also talks about, I love the way he talks about luck. And in particular he talks about four types of luck. Blind luck, luck through persistence, spotting luck, and built luck. Can you break down some of those types of luck? What does naval mean by these different types?

Patrick O'Shaughnessy (23:11)

Yeah, and this ties in well with the sort of authenticity and specific knowledge. Because the ultimate form of luck is to like, be the kind of person that luck is your. Your destiny. Right. Like opportunities just befall you. So the blind luck is the first. Right. Which is what most people think of like, did you walk over $100 bill today or not? Did you pick it up? Did you notice it? What was the second?

Cody (23:35)

The second is luck through persistence.

Patrick O'Shaughnessy (23:38)

Lucky persistence. Okay, so like if you happen to walk across a $100 bill versus if you went out on the beach with like your, you know, your metal detector and like spent hours looking for something that's, you know, these are simple metaphors, but like, did you happen to run into somebody who wanted to you to paint their house today, or did you knock on 200 doors and find three people who wanted you to paint their house today?

Cody (24:04)

But that's also too, because there's like a lot of studies now that show that you actually will not see lucky things if you think you are an unlucky person. Oh yeah, like, have you seen. I just was reading a study the other day where they gave two groups of people, you know, blind study. Basically. One group of people was told varying things to the degree of they're lucky, good things happen to them. And they are the type of people that believe that. The other group was the type of people who say things, good things don't really happen to me. I'm not super lucky. Then they were given a task and the task was to go and look through a booklet for how many times some word was said. So I don't know, bad. And it's like, go through it and look for how many times bad is said and tell us at the end how many times bad is said. And then you'll get 1000 bucks or something when you find the 217 variations or whatever the number is. And so the first group that thought that they were not lucky, they went through diligently. They got to the 217 number. They told them, okay, 217. And the other group goes through it. And on page five, there's a little paragraph that says you can stop searching. There's 217 instances of bad. And this other group finished it in like 60 seconds. And this group took 10 minutes on average. Like their, their vision was the same, like they came from sort of the same socio demographics. But one associated it's not lucky and one associated it's lucky. And so I thought that was fascinating. I love that, you know, and so explain to me spotted luck and then built luck.

Patrick O'Shaughnessy (25:38)

Spotted luck is just the ability to sort of position yourself at a place where luck happens to you, right? And so this is, you know, maybe the highest order decision is like, where do you live? Like, what's your exposure? What's your surface area to look? If you say you can't find anybody, like, ask out on a date. Like, okay, how often are you like going to parties? Have you left your house? Like, where are your habits? How many companies have you started? How many companies have you met with? Like, how many customers have you approached? Like these things are. You can control your surface area to luck essentially. And then the final form where like luck becomes your destiny is just. You just become so uniquely known for a thing, like you've reached such a final form of awareness and excellence and authenticity that luck finds its way to you. And like Warren Buffett is an example of is it lucky that he gets a phone call to like buy a bank and do a deal of financing that like nobody else has the capital or the reputation or the speed in order to do. Like he has become the only person on earth who can get that lucky. And that's a crazy example, right? But like there are many smaller forms of that. So your reputation, your mindset, your positioning essentially like that is a, is a very long term game.

Cody (26:57)

It's a really good point because I feel like what naval actually teaches a lot of us is that all these things that seem like unfair magic, AKA leverage, luck are actually really curatable and you can change your ability to have more of them as opposed to be a victim of the world around you. And so like luck can be manufactured

Patrick O'Shaughnessy (27:19)

in effect in particular if you're young. I feel like it's hard to appreciate that what, how lucky some people are getting is actually 20 years of like carefully grown seeds and reputation and relationships and effort. And like you shouldn't expect to get as lucky as somebody that has created that much surface area and covered that much ground. But you can sort of match their pace or outpace them by, you know, being thoughtful about your luck surface area.

Cody (27:50)

What would naval say about how to become luckier? Like, how could you become luckier?

Patrick O'Shaughnessy (27:54)

I think the path towards luck is you can follow those things up, you can sort of go from one level to another. You can do luck through persistence and effort that then becomes a little bit more of luck through. I have a feel for the dynamics. And if you really, if you gain enough information through the persistence and reputation, through the persistent luck, you'll have better information on where the luck might be heading and you can sort of meet it there and position yourself for it. And if you do that enough times over time, like you become the only person who can do it. So if we use the real estate example that it uses for leverage and just like take that as like, you know, if you're a, if you're starting off as a general contractor handyman, like you don't just wait around for jobs, you go knock on doors. If you knock on doors and do a great job, you'll start working more and more and get higher and higher quality referrals. If you are doing a bunch of work in one particular neighborhood, you start to learn like maybe that neighborhood neighborhood is up and coming and a new development is going to move in. And then you can, you can buy land ahead of the development or you can invest in the person who's coming in to like renovate this neighborhood. And if you do that a few times, then you become, you know, the person who builds the developments in the city. You've done the last five. They've all been successful. And so of course the sixth development is going to like pick up the phone and call you directly. And you don't even have to pitch anybody, right. And I bet you if you go through like all of the A list of Hollywood right now, you can map their career phases to those different forms of luck. You know, there's people that like, when you need a specific type of actor or character, you're like, well, Christopher Walken's the only person who can do that role. That's who everybody fills that gap with. If you need a certain kind of movie directed like, like it's. And you want it to be top tier, it's going to be one of 10 people. And those people had to all like grind and then iterate and position themselves. And then they became like a singular person who is like, gets the phone call. Like, is Christopher Nolan lucky when he gets the next phone call or is he like spent his entire career becoming the person?

Cody (30:03)

That's so true. And I feel like that's true in everything in life. It's like a mixture of like data collection that you do and then data collection that other people do, all on you. And when those two things come together, you get luckier. And so in the beginning, all you can do is collect as much data and do as much action as possible, which would be play a lot of poker hands in the beginning and really learn what the cards mean and what the percentage likelihood is. And oh, most people that tell right there they did on their face is actually a thing. And oh no, it's a really bad probability if I play that hand. So I probably shouldn't play that hand over time. And I need to put more chips in because if I don't, it turns out over time actually taking too little risk isn't good. And so I think most people in life don't think about life as like a series of hands or a series of like data collection points, but that is all that it is. So like, if you, whatever your life is today is really a reflection of like how many hands have you played, paid attention to, looked at the data on and then iterated on and like, that's it.

Patrick O'Shaughnessy (30:58)

Yeah, I'm not, I was a little impatient early in my career and I'm not advocating for patience or slowness or anything, but my perspective now in my 30s, is that, you know, the first 20 years of your career is an audition for the second 20 years of your career. And, like, if you look at Walter Isaacson, right, Like, did he get lucky? When Steve Jobs called him, was like, hey, I'm. I've got a few good years left. Like, I want you to write my biography. It's because Isaacson spent the first 20 years of his career writing permissionlessly writing biographies of da Vinci and Einstein. Like great figures, but they were historical. Anybody could have written those. He didn't have unique, special access, necessarily. But by doing that work, he became the person who got that call. And by doing Steve Jobs biography, he got the Elon Musk biography. And so these are permissionless books. I've spent the first 20 years of my career building permissionless curations of public material. And I don't know what's going to happen in the second half of my career, but I imagine that it will look like luck. And it's only because people have been reading my books for 20 years and have a respect for what they have done that I will get opportunities that, you know, no other author will have

Cody (32:07)

had such a good point. What does Naval say about. Or. And I don't know if he does, but this. I have a recency bias. Lately, I've noticed a lot of creative people saying they don't do creative free work. Meaning, like, they'll want to apply for a job and not want to do a project. And at our company, one of the rules is, like, we have to see your work because resumes and history has so little correlation to good and a fit. There's almost no correlation. And it used to be that if you worked at some of these big companies, you're like, there's a pretty high indicator that you might continue to have, like, a certain output or level. And since then, we've realized, in fact, that sometimes those are the worst people to hire. And now you almost have to talk me out of, if you went to Harvard and worked at Google, why you should work here. And so now we make everybody do a creative project. And I don't like to pay people for it. Not because of the expense. I don't like to pay people because I want to know how they feel about doing work with us. Are they really interested or are they merely kind of curious? Because if they're kind of curious, there are many companies to go be curious at, but it's not this one. And so I'm curious, like, you've done so much free work throughout your career, both like writing and collating things and doing lots of stuff on the Internet. One, how do you feel about doing free work in order to get eventual super highly paid work? And two, is there anything Naval says about that?

Patrick O'Shaughnessy (33:32)

I'm very happy to do free work that I assign myself. I don't know if I have the same relationship to free work that somebody else wants me to do for them. If it's along my natural curiosity, maybe, but. But kind of a natural independence is like when you're doing things for their own sake, you do them at a different level. But if I want to really wanted a job at a company, absolutely. I feel like I would do a project to get a job for sure. I mean, Naval is a fan of, like, doing things for their own sake. And he has an interesting story he tells that I think about all the time, where he's like, the most lucrative year of my career, where I created the most value. I didn't think I was working. I told everybody I was retired. And I just kind of, like, cleared my calendar and did what I wanted and followed my curiosity. And, like, in retrospect, that was outrageously productive. And I didn't know it and I didn't intend it. I didn't trick myself into it. I just followed my curiosity and it all worked out. So I think, you know, like many things, sometimes rewards are best pursued indirectly. And so, like, this book is excellent. If people see excellence in it is not because, like, somebody told me to make it great. It's because I cared about it enough to invest a lot in making it great of my own choice and volition. Like, I'm not a perfectionist in any other area of my life. But, like, when it comes to putting out a book with my name on it that I think, you know, might make a difference in people's lives, I'm, like, utterly meticulous.

Cody (35:00)

Naval has a line I loved, which is desire is a contract you make with yourself to be unhappy until you get what you want. What a line. What does that mean? And how do you integrate that into your life? Or how did you see him do it?

Patrick O'Shaughnessy (35:14)

Yeah, his happiness arc is so interesting. Right? So he had achieved all this incredible material success. He built successful companies. He'd been an incredible investor. He was well known in Silicon Valley. And he sort of looked around and was like, all the things that I thought would make me happy, I have them, and they do not seem to have made me happy. So maybe I need to just make a study of happiness. And somebody said to him, if you're so smart, why aren't you happy? And it's like, oh, I can apply my intelligence to this problem and I can break it down. And so he started reading the most of the happiness canon is kind of this Eastern Buddhism and things like that. So desire is a contract you make with yourself to be unhappy and to get what you want is a very. A modern phrasing of a Buddhist idea that type a business people like us sort of immediately identify with. And it identifies if you set yourself a goal, which we are all doing constantly, unconsciously, probably hundreds of times a day, especially if you're on social media, Instagram in particular seems like this bottomless well of desired creation. Of course you're going to be unhappy. And if you can learn the discipline of having few desires carefully chosen. His words that you spend a lot more time being content being happy, not feeling lesser, not waiting for some future state where you have something that you don't yet have, which is a very natural human tendency. But you can make just as much progress and maybe more by just not holding a strong burning desire that is making you unhappy every minute until you've achieved something.

Cody (36:51)

Naval also talks about getting a partnership and what it means to be in like partnership. What would Naval say is important in choosing your partner?

Patrick O'Shaughnessy (36:59)

Naval cites the great Buffett as like using the energy, energy plus intelligence plus integrity as like the formula for a successful partner and somebody that you want to work with or invest in. I mean Munger and Buffett are like the partnership that everybody aspires to, right? Like great friends, phone call every day, you know, 60 year, zero fight partnership. And Buffett's track record is investing in CEOs and abdicating entirely to them. And so you got to be a really good people picker when that's your strategy. And so I think that's a perfectly great formula to emulate.

Cody (37:39)

I can't remember if it's Munger or Buffett that says when you get a dog, don't do the barking for it. So I like that in partnerships too, it's the same thing. You know, don't hire a CEO and then do the CEO in the forum. Yeah, I think that makes a lot of sense. What about. It's interesting because we've talked about happiness with Elon Musk, we've talked about happiness with Naval and sort of that neither of them really seem to aspire much to raw happiness. Do you think that success and happiness go together? Would Naval say that they go together? Do you believe that they go Together,

Patrick O'Shaughnessy (38:16)

I think they go together. For some people. I think some people there's a balance of like some people it's easier to achieve your material desires and for some people it's easier to lower them or dismiss them. Naval's got a great line. It's maybe like the ultimate Naval line, which is the true test of intelligence is whether you get what you want out of life. And if what Elon wants out of life is to be like the maximum contributor to the flourishing of humanity and human progress, no matter what the cost or risk, then he's getting what he wants out of life. And if somebody just wants as much peace as possible, then they should go live in a monastery and yield any desires to affect the material world or have deep relationships. And maybe they have an incredible subjective experience and most people will end up somewhere in between. But as long as you're at peace with the trade offs that you're making and you're not trying to fit five impossible things to coexist into one life, I think your formula for happiness and getting what you want out of life is going to be uniquely yours.

Cody (39:23)

What are the lessons that you keep going back to from Naval? You've studied him for years and now interacted with him for probably a decade plus. Like what do you go back to?

Patrick O'Shaughnessy (39:35)

I think that's a, that test of what you want out of life is a good one. I first felt drawn to Naval in the same way I felt drawn to Munger because I such a high percentage of what they said was both surprising and just like immediately like felt correct to me when like 90, 99% of what you hear somebody say is like huh, Nailed it. In a way that felt right to me. They're not going to be everybody's heroes, but they spoke to me for some reason. And Naval takes all of Munger and sort of puts him in a progressive technological setting that's exciting and futuristic and more growth oriented. And I like the combination of those very much. But Naval also lives quite a balanced and well rounded life. I'm more of a Munger guy than a Buffet guy because Munger is kind of a polymath and Buffett is maniacally focused on just Berkshire and compounding his capital. But Munger has many different interests and many different curiosities and has gone down many rabbit holes and lived many lives in the same way that Naval does. He's founder of Angellist and investor in a ton of companies and started many companies and is intellectually well rounded and well read and curious and plays around with ideas and applies them in many different ways and has found a way to find both peace and happiness and success, like material success kind of all at the same time. And material success in a way that is like, meaningful to him. Not externally or image driven. I think, in my view, which is certainly what I aspire to, because those are winnable games. The inner scorecard is a winnable game. You can set the goalpost and achieve them and you can make sure that you're always happy with. With where you are, that you're not trying to fill this bottomless bucket with someone else's perception that you have no hope of controlling.

Cody (41:28)

Naval has a line that I love that's very jarring about how a salary is the most addictive form of heroin. Something to that degree.

Patrick O'Shaughnessy (41:39)

It's a Taleb quote. The three most addictive substances are these. Heroin, carbohydrates, and a monthly salary.

Cody (41:48)

Yeah.

Patrick O'Shaughnessy (41:48)

And that, like that push to get you out of the. Out of the comfort zone. Right. Like, Taleb's morality is all around, like, are you a risk taker? Are you exposed to the upside or downside of your own behavior? Or are you kind of like a lamb in the paddock? And, you know, like many things, Naval finds, like, a pithy, kind of powerful way to phrase it, but it's. It's a nice way to just kind of like, give you a nudge towards your authentic self and to, like, feel the rush and the risk of being. Feeling your skin in a game and feeling exposed to the upside and being a little more authentically you. And on life's adventure.

Cody (42:27)

Yes. I think a lot of people live life like they're watching the football game and they've never stepped foot on the turf. And that, to me, is sort of sad because the difference between feeling what a hit feels like and smelling the grass and having that actual adrenaline that comes up at the beginning of it versus the small percentage that you feel when you watch somebody else do it is. It's a world away. And so I do think a lot of what I've learned from Naval, at least, is how do you get a little closer to the action? Because that is the only way. One, you get leverage. But two, it's the only way that you can actually feel the full human experience in many ways. And he talks about. I don't agree with him on all of it, but I do like, I like that he pushes. Like there's. He talks about how, you know, he'll never get rich renting your time.

Patrick O'Shaughnessy (43:20)

Yeah.

Cody (43:21)

And I actually don't agree with that. I mean, mathematically it's not true. Like Sheryl Sandberg, quite rich, always been

Patrick O'Shaughnessy (43:28)

an employee, but also she was an employee at the level where she had massive equity upside, right?

Cody (43:33)

Well, I think that is the part that gets waylaid in some of this, like is a belief that you can't be an employee without massive upside. And you can rent. I mean, she does typically, she does actually, you know, like quantifiably rent her time. She is paid a salary, right? But her upside probably comes all from equity warrants, options, et cetera. Well, so what maybe explain that. Like that would be an interesting question, which would be something like, can you get really rich on a 9 to 5? Can you get really rich renting your time or on salary?

Patrick O'Shaughnessy (44:10)

Maybe the nuance is that you need asymmetric upside, right? And so one of Naval's sort of directions in one of the chapters in the book is like build or buy equity in a business. Like you need equity upside, you need asymmetric exposure. And there are many jobs, there's many ways to get that. There are people who get reasonably rich, who become millionaires, who work nine to fives their whole lives, but they're really diligent savers and investors and they max out their 401k and they live on half their salary. And this is like the fire movement, right? They, their way of getting equity is just like buying the index with half their salary and keeping living below their means. That's a way to get equity. You probably won't become a billionaire on $100,000 a year and a, you know, 50% savings rate on equity, but you will almost certainly become a millionaire if you're diligent about it over a 50 year time period. If you ascend to, you know, if you're climbing the corporate ladder, there are career paths where your salary will go up, but you'll still never get equity exposure. I feel like doctors are the famous example of this, right? Like we all know cash poor doctors who are like making 700 grand a year, spending 700 grand a year. They never have equity, they never bother to figure out the game and they have no retirement plan or they have a, you know, they never build up a net worth because they're just like their lifestyle consumes everything that they earn and they have no equity. But you know, in the case of CEO, cfo, C suite, VP and above, like, you just want asymmetric exposure. If you believe in the company that you're working at, you want part of your package to be equity so that you get like. Even salespeople have asymmetric exposure. They have nonlinear earning potential. But if you ever want to be like sort of truly passive and live off the capital, you need to start figuring out the equity gain.

Cody (45:57)

It's so true. Naval Al has a quote where he says the real winners are the ones who step out of the game entirely, who don't even play the game, who rise above it. These are the people who have such internal mental and self control and self awareness. They need nothing from anybody else. What does he mean by that?

Patrick O'Shaughnessy (46:14)

I think this is the very ultimate inner scorecard, right? So much of what people are driven to do is driven by this memetic desire. And they're always sort of moving the goalposts on themselves. You have to know why you're playing the game. This is the enlightenment path. And there's all kinds of books that he recommends and conversational that he's had with people. But if you study those sort of enlightened people, they're just like removed from it. And some people feel compelled. They can't remove themselves from the game until they've won the game. And not everybody's like that. Some people could be like, this is all a hallucination. I'm just going to remove myself. But some people need to win the game and then look around and be like, oh, there's nothing else here so I can escape the game. But there are so many games that you can spend your whole life playing them and just kind of leap from one to the other and always feel, you know, behind or pressured or like driven. And if you know where the road ends, like what I took from Naval reading this, you know, building this book when I was like 30, is like, oh, if you grind and beat yourself up and have this brutal internal monologue and like, like all the way to like winning the game, finally achieving all these things that you hope to the whole time you have the same epiphany that you can have right now, which is that like, none of it matters. It's all made up. You don't even exist. None of this exists. We're all in this like a hilarious, absurd dream state. So don't take it all so fucking seriously. You can get the things that you want, or you can choose not to want them, or you can, you can be almost. You can probably be equally effective by just like, by having emotional detachment rather than having like being all in, all consumed emotionally, like wringing yourself out every day, feeling massive stress about everything that you're doing. And if you know that that's the eventual end state is like, do I need to wait until I'm 80? And I've lived a whole life of mistakes before, like embodying that epiphany or can you just be like, I can keep playing the game because it's a fun game and we're here and why not? Like, yeah, it's a fun dream and

Cody (48:34)

then it kind of doesn't even have to stop you from your speed. Like I don't know about you, but when I was younger I used to think, well, if I don't care the most and if I don't get emotional, if I don't get upset, then I'm not gonna win because that's what winning takes. Then I realized actually having like a pretty big step back from like that pain in your stomach or that anxiety in your heart when something happens and being able to look at it rationally is a complete step function change in your decision making capability because you're not living in flight or fight and your

Patrick O'Shaughnessy (49:06)

longevity in the game and your energy level within it and your ability to sort out like what is what matters and what doesn't.

Cody (49:13)

Yeah. Because otherwise you just, you get adrenal fatigue, you're just, you get burnt out, you have decision fatigue. You know it's interesting, I had a member of my team and you know, he was really good and you know, in his words, he burnt himself out. And so I was like, well, let's talk about that. And he said, well, you know, I just don't know that I want to keep doing this. And I've got all these things and I go, well, do you need to hire somebody? Like, do you think that that is a truth? That you always have to stay in said role doing the exact same thing continuously and then yeah, surely if you look down into the future, 10 years down the road, you probably think that doesn't look like a very fun role road to go on. So why would you? And what I found with a lot of people that job hop or can't figure out what to do next or when they jump around, they have a great sprint for two years and they're kind of not sure is like wherever you go, there you are. And so you can change your location and even change your title, but if you are a people pleaser and you stay one, if you don't know how to delegate and you never figure it out, it's really problematic because again, you build this constraint that isn't even there. And so some of the stuff I think that he at least teaches me is, yeah, it's about what do you want or not want? But also like even figuring out what is possible or not and where do you have these fake constraints that you don't even realize?

Patrick O'Shaughnessy (50:35)

That's what I was back to. The Elon algorithm is like the question of requirements and having like, how do you give your team members agency over their environment is like, I love this company, but this role is now breaking me. What do we need to change in order to unlock this and continue it and help the energy proceed? And of course there's many solutions to that.

Cody (50:57)

What questions do you ask yourself when you're in that position? Because I think part of this is self realization with Naval. So Naval would you would even have to first recognize in yourself. I feel this way. I need to name it. I need to figure out why. Like, how would you, if you were struggling right now and felt trapped or lost and not know what to do next, what have you learned?

Patrick O'Shaughnessy (51:16)

To me, the most universal thing and the most, the thing that I come back to most often here is like thoughtful desire management. I've. I've now noticed when a new desire enters my mind and I have to like triage it and I've learned to like, you know, I used to, I used to like watch stand up comedy and half of my experience of watching stand up comedy would be like, I want to be a stand up comedian. I fucking love stand up comedy. There's a version of me that should be a famous stand up comedian. Like, and I, I've just totally dispelled that desire in my life. I still love it, I still respect it as a medium. I think it's incredible. And I don't know if it's age or just thoughtful desire management, whatever, but it's like very clear to me now that I do not want to pay the price to become. I don't want the lifestyle, I don't want all the things like, you know, the price tag is too big. It's a fun thing to fantasize about. And now that's kind of like I've just completely dispelled that desire. And that's. There are a thousand examples like that. And I bet you know, open Instagram or Twitter for five minutes and you will, you will feel a new desire welling up in you. You just walk outside and you. A new desire will well up in you. And big or small, learning to identify that and say, like, do I really want that? Is that a meaningful desire? Is that a Long term desire, is it worth changing, you know, the course that I'm on? What would I sacrifice? Do I want that thing enough to pay the price tag for it is like almost always the answer is no. And the quicker you can close that loop and the fewer of those that exist in your head at any given time, the happier you are on a minute to minute basis.

Cody (52:52)

So how do you do that? Do you literally go, okay, I feel a desire. So like, I hear in my head I want that, so I recognize that. And then I think, what would be the prices that come with that? Like, what does that thought process look like for recognizing a desire and not immediately latching onto it?

Patrick O'Shaughnessy (53:08)

Well, I mean, an example, like a friend texted me today and is like, did you hit your targets for the book launch? And I was like, I don't have targets for the book launch. I don't have. Like, that is an arbitrage. I'm not going to pick a number that I have, like may or may not work is If I pick 10,000 copies and I sell 9,000, am I supposed to be sad for how long? Like, is that a useful desire or not a useful desire? Which is arbitrary. So like, I don't know. I don't hold any desires particularly closely. And the longer the term and the more vague they are, the more helpful it is. Right? Like, I want to have a wonderful relationship with my wife. I want my kids to have an incredible whole life. Am I stubborn about any of the specifics about how that needs to look? No, not really. And so the version of like, do I have to go to one specific place at one specific time on a vacation? No. Oh, yeah.

Cody (54:02)

I don't know.

Patrick O'Shaughnessy (54:02)

It's just there's like a loose grip over almost everything is like, maybe where you end up after some practice of like triaging these desires.

Cody (54:12)

It's fascinating because it is very Zen in many ways. But I guess you and your career have been like that. Like, you've done tough things, a turnaround, you know, of a company while writing books. Books themselves are not easy to do in general. You've also had startups prior to that and you felt what failures felt like. So I guess maybe the last thing would be are there quotes you turn to from naval this book, this period in your life that you think would be helpful to someone who's listening right now, who is a little lost maybe and doesn't know where to go next?

Patrick O'Shaughnessy (54:48)

I think the lesson that so many of us learn and have to learn many, many times is to trust yourself and Your intuition. Right. Like, that seems to be like the weird arcs and turns of my career have all sort of come back to, like, just trust me. Trust that little voice a little sooner sometimes. Is that, like, also your experience?

Cody (55:13)

Yeah. I think we're wrong a lot less often than we think we are. You just talk yourself out of it. Yeah, that's not in every case, but especially once you've developed that. In the beginning, I would say I was a little bit of an idiot, and I thought I knew a lot, probably. And through most of my 20s, the

Patrick O'Shaughnessy (55:31)

kind of like Dunning Kruger, like, small information, high conviction.

Cody (55:35)

Exactly. And then at some point, you start to see a lot of cycles and think, oh, I've seen this before. I should just listen to it.

Patrick O'Shaughnessy (55:42)

Yeah.

Cody (55:42)

Then when you figure out that little voice in your head is telling you something, I think then the question becomes, like, what do I do with that? Because usually it'll tell you something, but it won't say, you could go bad. Like, if you say, like, I'm so mad at my wife, I'm gonna leave her. Well, that might not be. It might just be saying, there's something really wrong in my relationship. Like, that's what the voice is saying. And so what does that mean? Well, maybe it means you actually lean in more. You do more things. But I think most often we just try to shove it down, Ignore it.

Patrick O'Shaughnessy (56:10)

Yeah. I mean, listening to the voice, allowing it to go long enough that you see the patterns. Right. Like in that moment of anger, maybe you're not getting a clear signal. If you think that twice a day, every day for six months, maybe there is something really know, really wrong with the relationship. But in another, like, after you listen, you need courage. Like, a lot of people hear the voice and the choice is either to repl. Repress it or to act on it over a certain amount of time. And I think the people that end up the most unhappy have repressed so much because they never summoned the courage. And so they're, like, deeply aware of what it is that they truly want to be doing or feel like they could be doing and just never took that next leap. I think it's a Winston Churchill quote. Like, courage is every virtue at its highest form. And so you can understand all the virtues, but if you don't have the courage to act on them when it's difficult, when everything else is sort of going against them, they have no form.

Cody (57:14)

If we were going to get really tactical with it and somebody wanted to hone their desire plus their courage, what would you Tell somebody listening right now, how do you get more courage and how do you listen to that little voice inside of your head more often?

Patrick O'Shaughnessy (57:30)

This is not a Novalism, but I know people who swear by this, which is just like a morning brain dump on paper. The process of externalizing these thoughts somehow helps you evaluate them and it forces you to be honest. And so if you see what sounds like absolute certain reality in your head of like, I have to be this or become this or get this or I will never be happy, as soon as you write it down, you're like, that's stupid. But if you just live with it in your head the whole time, you're like, you could feel your body responding to it. And that, that practice of externalizing it just helps you observe it rationally. And it's, it's a. What's. It's a shortcut to doing that. Meditation is the same way. It helps you separate sort of the evalu, like the observed from the observant, like, see your own thoughts from above. But writing it is a shortcut to doing it. And that's a helpful method. And by the same token, like doing that over time, like you can only write, I hate this job, I want to quit. So many times before you're like, oh my God. You know, you will respond to observing that over time, you know, whatever it is, like, if you stay present with it, the courage, I think, will eventually sort of culminate and you will manifest that in some ways.

Cody (58:55)

So true. That's so true. I loved this book. It was my, obviously my first book I read of yours. I read it years ago. I come back to it often. Thank you for writing this and so many others. So we get to learn from the great.

Patrick O'Shaughnessy (59:07)

Thank you for having me. It's been really fun to sort of co evolve with you and see like you are living some of the principles in this book at an extremely high level. And it's really, it's really awesome. Like if you don't. For people that don't understand sort of the journey that you've gone on, I think like the principles here that are making you successful are of like leverage and equity and compounding are like you took this blueprint and ran with it and built something.

Cody (59:37)

Probably. I definitely did. We've known each other a long time now, now that I think about it. How many years do you think

Patrick O'Shaughnessy (59:44)

this book, this came out in? 2020.

Cody (59:46)

So yeah, well, definitely before that.

Patrick O'Shaughnessy (59:48)

So eight, 10 years, maybe 10 years.

Cody (59:50)

Which means we're old.

Patrick O'Shaughnessy (59:51)

It was like early Twitter X You know, I, like, we were in a, like, Twitter, like, support group together where we were like, you. You assembled this, like, team of people to help each other. Like, it was like, dude, it was like a Sprint 100K, and, like, you made it in three months, and now

Cody (60:08)

you're at, what, I think 700K.

Patrick O'Shaughnessy (60:11)

700K? Yeah. Unbelievable.

Cody (60:14)

It's true. Well, that is another thing that I think, you know, both the leaders we've talked about do a really good job of and I've tried to learn from is, like, not just, like, it's a big world, pull along other people. Like, why do we have to shove other people down? I mean, I pretty much never, ever talk shit on the Internet to an individual because I just find that, like, it's so much more beneficial to, like, celebrate friends, celebrate wins. You know, try to win more myself, and then get in other groups where other winners already are, you know? And I learned, I think that group, most of those people in there probably, besides you and I, were bigger than us on the Internet, and now probably aren't because, like, I think we were connectors. And you're, like, a super connector, you know, with lots of companies and people on the Internet. So that's another lesson I've learned.

Patrick O'Shaughnessy (61:00)

So we just sit at home and write, and, like, you're out there running a media empire.

Cody (61:05)

Well, we run a lot, but that's what I like to do. I like to run companies.

Patrick O'Shaughnessy (61:08)

I like to sit at home and write. Where you sound. Right?

Cody (61:10)

No. And you definitely know who you are. I think it's a very good point that, like, this makes me incredibly happy, what I do. So I would consider myself a happy builder, even though it's really hard. And. And my happy looks totally different than yours. But we both, like, kept listening to that little desire and playing into it more and more and more and sort of obsessing on it. So, like, people are gonna have a hard time beating you at writing. These people are gonna have a hard time beating me at building media companies because it's just what I do for fun.

Patrick O'Shaughnessy (61:36)

People are incredibly unique, and, like, the further you go in life, the more unique you should become, you know, like, if you're not weird, how do you know you're free?

Cody (61:45)

Oh, yeah. One of our main 13 principles is bring your weird. It's better than boring.

Patrick O'Shaughnessy (61:50)

Yeah.

Cody (61:50)

So, like, that is so true. All right. You're the best. Thank you.

Patrick O'Shaughnessy (61:53)

Thank you.