Does Money Buy Happiness? A Conversation with Deca-Millionaires
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Hello, everyone, and welcome to this somewhat experimental episode of Deep Dive. I'm joined by Patrick and Matt, and I'll get you guys to introduce yourselves in just a sec. I thought it would be fun to do a bit of a deep dive into the psychological and emotional aspects of money, because money is such an important part of all of our lives, whether we like it or not. It's so deeply intertwined in literally everything that we do. And yet still talking about money is kind of weird.

Now, over the last few years, I've been making videos on my YouTube channel every year where I kind of break down how much money the channel and the business has made. And I've been doing this since like 2019, where I was making like 100K and then it was like a million and then it was like three and then it was four. And so I'm fairly transparent with my audience that my business is doing like single digit millions in profit. But Matt, you've sold a company for tens of millions. And Patrick, you've sold a company for hundreds of millions.

And I thought that's like a cool place to be where like you guys are at least 10 to 100 times wealthier than I am. And it's just that's kind of cool because, A, I don't meet people like that very often. And B, don't get a chance to sit down in front of cameras to ask them about that whole experience. So I wonder if you guys can introduce yourselves and be like, Matt, who are you? What's your background? And how did we end up here together? Yeah. So Matt Chinook, I am actually I grew up in a family in St. Louis, Missouri.

on the topic of money that is now an 80-year-old family business. It was named my last name at Schnucks, which is a supermarket business in the Midwest.

My relationship of growing up with money was one where people would meet me in this town I live. They'd associate my last name with quite a bit of wealth. Even though while I grew up with, you know, fantastic education and privilege, I didn't have access to that wealth. My reaction... Like trust funds and all that jazz. Exactly. And so my reaction to that was...

not to go into the family business, but to run from it and to become a entrepreneur myself. So I moved to San Francisco and ended up starting a business at 25 that I was able to bootstrap to this sort of eight-figure exit that was a life-changing experience for me. But I've had the unique experience of seeing wealth in a multi-generational family and the way in which that

uh, certainly doesn't necessarily lead to fulfillment and happiness. And then I've had my own experience of going to like getting this massive wire into my own bank account and, um, reckoning with that. Why are we here? Uh, we're here because one of the things on my own personal journey, um, I really love to do is, uh, create environments. And I'm doing this in partnership with Sahil Bloom. We're organizing these events thrilled that you're here as part of it. Uh,

Patrick as well, where it is creators and founders getting together. We call it the inflection to sort of level each other up and coach one another over three days in a beautiful place. So we're here at my place here in Cabo. And, uh, um, what

What a good place to film. This is like the most insane place I've ever been in my life. So thank you so much for inviting us out here. And Patrick, your journey is, I guess, a contrast in some ways to Matt's. How did you end up here? Both mid-Western dudes, though. I was just realizing this is the most relatable podcast ever for everybody. No, no. Because I think there are some interesting lessons based on the frame that you kind of brought forward. But yeah, I'm Patrick Campbell. I'm a film critic.

I grew up in Wisconsin in the Midwest, relatively poor, very blue collar type family, never wanted to go into business. Business was like the last thing I wanted to do. I wasn't the kid who had all these like, you know, different entrepreneurial type tendencies, wanted to go to like save the world. And so I worked for the US government and then that was too bureaucratic for me. And so I went and worked at Google and thought, oh, this 30,000 person tech company will be very like non-bureaucratic.

but obviously he's bureaucratic and this kind of, you know, you're seeing a theme. It was less about those entities and more about me and ended up going into business. And yeah, to kind of skip ahead, I ended up a couple of years ago going from $19,000 in my bank account to selling a company for over $200 million. And yeah,

going from that entity and you know i was making a decent salary at the time um you know as running the business and starting the business but going from like this really really um not wealth background also like a background where you know

you know, my parents were very like anti-wealthy, you know, more like every time there was someone in the news, oh, that corporate person's a crook, those types of things. To then being that crook, no, I'm just kidding. But then, but to then being that, you know, that person, it was, it, it, it's, it caused a, you know, again, this isn't necessarily relatable, but like it caused an interesting, like existential crisis the past like year or so. And so, yeah, it was a very, very interesting, lots of learnings. I'm excited to share and go deep as possible. Okay. Okay.

So one question, like opening question for both, for both you guys, how does it feel the day that you get like fricking tens of millions slash hundreds of millions just landing in your, like, how, how does that feel? I, this is not a satisfying answer. I felt nothing like, don't get me wrong. It was cool. I refreshed the bank account a bunch. I looked at it for a couple of weeks to make sure that it didn't go away. But I think that the thing about wealth is it's

First, if you have a good relationship with money where money doesn't really matter to you, wherever you are in your standing, but you're happy, just thank your lucky stars. You were hugged enough as a kid. That's amazing. I think there's others of us who like...

we either think the pursuit of it or we think that getting it is all of a sudden gonna change things. But I discovered when I got wealth, like I'm the same person and wealth actually manifested or kind of like made the extremes worse. So my good tendencies, my good habits, my good types of purchases,

Those got, you know, extra, you know, extra magnitude to them, like giving and things like that. My worst tendencies, like eating bad food, being able to like not take care of myself, those actually got worse. And for me, I thought, oh, instantly I have money now. I'm going to be healthier.

And it's like, no, that's not how it works. And so at least for me, and not everyone has this experience, it didn't change how I felt to the point that I actually thought I was broken a bit, which I'm happy to get into, but one I owe you're up to. I mean, some similar themes. Like for me, when the wire hit and I similarly refreshed the account, I didn't know this at the time, but I was driving towards...

success as an entrepreneur and towards generating money because I was hopeful on the other side of that achievement, a new level of happiness, peace, and frankly, like feeling about myself would take over. And the harsh truth was I was still the same person. My mental, like my relationship with myself did not get changed by that external event. And, um,

I will say what it did enable, which I want to be clear about, and we took some different approaches, but I see some themes, is it did create time wealth eventually and also the financial resources to be in reaction to the fact that, whoa, I didn't feel as much as I wanted. It didn't have the internal change to me as well.

I could then have some of the resources and time to then go get some help to better understand who I was. And I think that's been more, uh,

powerful for me in terms of the impact, but that's been an internal game. Nice. So the reason I was so part of the reason I was so keen to have this conversation is because, you know, some of the videos on my channel that do really well are like, you know, how to make passive income and people are like, like weirdly videos about getting to 10,000 a month do better than videos about getting to a hundred thousand a month. Cause for a lot of people, a hundred thousand a month just seems completely fucking absurd. Yeah. That's 10 K a month feels like, okay. Yeah. You know, I, you know, there's YouTubers that talk about that. I'm curious for you guys, have you,

Like, have you got a sense of what are the levels of wealth where it makes a tangible difference to your life? Because presumably there's not much difference between 100 million and like 200 million, I suspect. But there's a huge difference between like 10K and 1 million, for example. So do you have a sense of like what that's been like for you? Well, so...

My wife grew up in a very different family situation. So she, she grew up parents are both immigrants from Mexico and had a sixth grade education. And she did not grow up with the same resources that I did at all. And we've come together and talked a lot about this. And I do want to be clear. And she, you know, sort of reminds me all the time. We still didn't have developed a game. And I do think that,

creating a baseline level of financial security such that you don't have to worry about where your expenses are going to be handled, I do think has like a totally different like impact on stress. And so, and Patrick's gone into a lot deeper research on this at all kinds of levels. But I do think that like,

having a thoughtful plan, whether you do what's in Tim Ferriss' book for our work week, Tony Robbins has a book of just like creating just like a basic financial plan and then creating the resources that gives you that fundamental security.

is a wise approach and does change baseline levels of concern. This is like practically, I don't think enough people talk about that needs to get done as sort of a first baseline step. Like if you're at the point where you're worried about paying your bills, then obviously getting more money is going to make you way happier because now you've removed all that stress from your life. Yeah.

And then I also have witnessed people, even after huge exits, who will let a level of lifestyle creep go beyond where their incredible means take them. And the fundamental concerns about do I have enough will sort of persist despite having created an incredible outcome. Okay. Yeah.

So as you get more money, kind of keeping your lifestyle costs fairly in check is an important part of that. It sounds like it's an important part of that kind of not being stressed out by money kind of piece. Yeah. I mean, if you're, for example, able to live, uh, uh, after like, like once you can get to a point where your expenses are 4% of whatever you have saved, that is a fundamentally like different just as a general rule. Uh, um, yeah.

you know, as long as you're sort of thoughtfully investing, that's a secure, you know, and sustainable sort of place to be. Yeah. Wealth impacts you to the level of your insecurity. That's really where it comes from. Like if you think about,

The reason I would posit that the $10,000 per month videos do better is not only because it seems more achievable, but because $10,000 in passive income takes care of a massive amount of people. And all of a sudden getting to 100,000 is nice to have. And maybe there's a thing that they could think about that they would purchase. But a lot of people, thankfully, are pretty well adjusted if getting an extra $120,000 a year. What I have found is that

wealth beyond 10,000 a month, 100,000 a month, and so on and so forth, it really impacts or the changes that starts to impact you are at the level of where that insecurity is. So to give you an example, like...

I know, I have friends who have had similar exits to us and they are numbers people, meaning that number needs to constantly be going up. Objectively, the number does not need to be going up. They're not purchasing anything that would need the number to go up. There's nothing that they want to buy that they would want to buy.

demand that particular number, but that number gives them some sort of purpose. And this is not healthy. It's just, it gives them some sort of purpose and maybe they convince themselves that's the game that they want to play and they get enjoyment. And maybe they actually do get enjoyment, but there's something in their psyche. There's something in how they were built or developed, depending on the nature versus nurture debate that has now caused them to essentially need to chase that.

And I think that that's something that as you get to these higher levels of wealth, it

Again, it's hard to empathize with, but it is something that's interesting to kind of understand. But the one thing a lot of people should realize, if you're getting to the 10,000, you will look to the 100,000. As you're getting closer to the 100,000, you will look to the million. And you need to kind of stop yourself and realize, ask yourself why. And most people will kind of pull back because what I have found is wealth is not a replacement for purpose.

And oftentimes people look at it as a replacement for purpose and they'll go chase something and then they won't necessarily feel something. The reason I didn't feel something is because, again, I wasn't hugged enough as a child, but also...

And the journey, this whole cliche of it's the journey, not the destination was really, really true. So when the wire hit, I didn't feel like I won the lottery because it was like, yeah, maybe the numbers are bigger than I thought that they were going to be, but I just did all this work for 10 years. And so there should be some outcome, right? So it was like, that's the thing. So it wasn't this surprise.

And to give a little bit of an anecdote, so before I sold the company and I was debating whether we should sell the company or not, I talked to 30 other founders and I asked them, and they all sold their companies for different amounts of money. I asked them, would you sell again? 15 of them said, yeah, absolutely. It was the best decision. Get the bag, et cetera. The other 15 said they wouldn't.

And of those 15, eight, seven or eight went with the company post-sale, meaning like they sold the company and then they worked at the company that bought them. And they said a lot of things about it was miserable, blah, blah, blah, blah, blah. The other seven or eight didn't go with the company. And that group, at least qualitatively, was the most miserable. They had all this money and then they were sitting there and they're like, they had lost their purpose. And they were like, well,

I thought the money was important and they de-risked their lives, bought a house, whatever it is. But now I lost the thing that I was doing. And now I'm just going to try to go rebuild that, but I had already built it. So what am I doing? And then unfortunately of those seven, three or four of them became substance abuse, like drug addicts or alcoholics. They're all good now, but it was pretty intense for those three or four. And so I think that

Wealth isn't a replacement for purpose is a really really important thing to keep in mind and unfortunately It's probably one of those wisdom things you can't really learn it until you experience it But you'll listen and be like a bearded guy said this and so hopefully it saves you a cycle or two I had to feel it myself as well, but I want to tell a similar story that so I had a Mentor in my life. He's now in his 70s and

He had the wisdom in his early 20s to say, I want to have a two-part life. He wrote a business plan for his life at age 23, which was by age 40, he wanted to become an entrepreneur, build a business, and have an exit by age 40. And he named the number he wanted to exit for back when he was 23.

And he felt like it was reasonable, it was achievable. Let's call it in today's dollars maybe high single digit millions. And he's had the wisdom at age 23 to say,

I am going to say that's enough for me. And I will always potentially want... A well-adjusted here. Right, right. A 23. I never would have thought this at 23. So he is actually at Harvard Business School while he writes this plan.

He got in on like an engineering scholarship and you know, he's at HPS at 23 as yeah, yeah, right And he writes this plan he goes ahead and he executes it at age 39 a year early he sells for and he hits his number and

he shifts into the second part of his career, which was purpose-driven. He decided intellectually, he always wanted to, he loved the law. He went to law school in his early forties and he became a lawyer who basically took on cases to sort of help, uh, uh, you know, defend people who, uh, and, um,

Is one of the most like sort of purpose-driven and happy people in his life, but now he's running for president. Oh But why how did he pull it off? Cuz I've thought of like how does he pull this off? Right because I'm here we're in this amazing place right and like

Two rows down there are houses that are three times as much that I could be pulled to want more. Right. And so I try to remember this guy because, uh, um, the purpose part of his life has guided him. I think the way he's stayed on track to me is for two reasons. Uh, and you're an atomics habits fan. So I think it's in there. So number one, number one,

he defined the, his identity in life later as having been living in, you know, consistent with this purpose of having a second career and helping people. Number two, uh,

He knew that his environment would matter. He moved out of like, uh, the town he lived in in St. Louis after he had this exit, he moved to Wyoming where the currency, uh, of his community was going to be health being active and, you know, not the rat race of, you know, the, the, the business community he was in about what are you doing next? Uh, what have you? So he literally made his environment be thoughtfully surrounded with people who were not going to

sort of challenge his intention of more, more, more, more, more. So he's, yeah, that story, uh, I think has a lot of lessons that 20 years before, you know, James Clear was putting this out, uh, and how it applies to money. He lived. Just makes me feel broken. But I think that what's really interesting about that, and you and I were talking about this is like that, like,

Like you and I have done an incredible amount of like introspection over the past couple of years. And, you know, if you're watching this, you probably are someone who does introspection. Obviously, you've done a lot of introspection. And I think that that makes me spark a question in my head that we're not going to settle, unfortunately, here, which is like, can you get to that level of like peace?

Or is it something that it's almost easier to assume you can't get to that level of peace, therefore how should you live your life, right? So what I mean is I've done a lot of introspection over the past year to get to what drives me, what motivates me, what is the next thing, do I need a next thing, all of those other things.

but I don't know if I could ever get to that. And it's limiting belief at least, but I don't know if I can ever get to that level of peace. Like the best thing I've gotten to is I like increasing like concentric circles of freedom, meaning like I am able to do this. Now I want to, um, try to solve this small scale problem in my town. And then I want to be able to solve a larger scale problem. Like that type of stuff motivates me, but I still have this like energy where, um,

it's an anxiety where there has to be something more. Like there isn't a contentment and it could be an age thing, I don't have kids yet, all these other things, but yeah, it's a really, like I wanna meet this person. I hope you can intro me. - Yes, I would love to. - I just wanna like go and drive up or fly up and be like, just tell me how you got here, like that type of a thing. - I mean, but one of the things that, I don't think he would put it in these terms, but he would say,

like he hacked his brain back to identity and said, part of who I am is going to be somebody who like, like thinks this way, does this thing. You could always want more. And so if he, and he's public about that, it was literally written into a paper that his professor saw. Right. And like publicly knew. Right. So he could, um, if he was going to go,

in a pursuit of more, at least financially, then he would be essentially living in contrast to his identity. And, you know, it's something that I thought about related to like some of the things we were talking about for you this weekend is like, if your clearly defined identity and purpose is measured totally on

impact or spending your time on teaching or, or, or, or what have you. And it's explicitly not financial beyond a certain point. Yeah. And then that's public. Uh, um,

One of the benefits of creating and saying stuff publicly is it can be scaffolding to keep you consistent. And in ways like before the internet and social media with the community and people he had in his life, he put that out there, which created a little, I think like identity scaffolding and support. I think the quick getting to the point where finances are,

are not driving decision-making as quickly as humanly possible is the path. Now, one step or two steps down from that is where I would consider myself. And five steps down from that is where this friend you're describing is. Where I'm at is like, I don't have to do anything, but there are things that I would like to unlock

with what I have or what I could get, et cetera. And I think that that first level is where everyone can get either by getting content with their 40,000 or 40,000 pound salary per year, or doing some of this introspection of what's really important. And you and I have talked a lot about this the past year of how important it is to just think about what do you want? Yeah.

and then work backwards. And that's what it sounds like this person has done to a level that very few people even get close to, which is really, really thankful. Yeah. So I had a podcast guest who has now become a friend. His name is William McCaskill, and he's a philosophy professor at Oxford. And he has made a public pledge to basically donate all of his money beyond 30K a year.

And he says that the fact that he donates everything above 30,000 a year makes him happier than a lot of the billionaires he hangs out with because he's into this philanthropy stuff. Because A, it means that money just does not feature in any of his decision making. And B, it actually forces him to live with roommates and housemates, which increases social contact to the point that he's even realized that if you have the configuration of a house, that means people are forced to go through the communal space to get to their bedrooms. It increases social cohesion.

Because if they can just go straight from the door to their bedroom without going to the living room first, it means you can be ships passing in the night and not like see each other. And so he's engineered his life around social contact and connection and impact and stuff. And genuinely comes across as a really, really happy guy. I think it's one of the things I discovered through therapy this past year is I hired this therapist. We've talked about this and it hit me at the right time too. So that's where it was like such good impact.

And a lot of entrepreneurs, including myself, have this weird duality of how they like see the world or how they like think about themselves. And on one side, I have like, I score high in like depression. I score high in like nothing's ever good enough. And on the other side, I score high in this like,

it's a level of self-importance now it's not like a straight-up narcissism it's it's a i have a purpose i'm here to like do something if i'm not doing something to better the world therefore i um am you know giving the middle finger to the person who's digging a ditch who was not able to have an opportunity to do something that i'm doing basically i can't just sit still because that's just so rude to the rest of the world and i think that that duality

drives a lot of, well, we have to keep doing something. And all of it is BS, right? Like all of it is like, it objectively is not necessarily true. Like things are good enough. The depressive side is wrong. There's no reason I have to like do something, right? I can go just optimize for social interaction. I can optimize for happiness. So it's not objectively right, but

But those two sides, like nothing's ever good enough and I have to achieve, it makes this weird mix where it makes you keep going and having to find that particular purpose. And, you know, could you find a different purpose that is different? Absolutely, right? But a lot of us also think it's fun, right? Which is really, really interesting. Like the idea of like,

the 30,000 aside, but the idea of like, you know, having that existence where every day you're having just really premium social interactions. I'm sure he's, you know, getting really good fulfillment out of teaching. I look at that and I go, oh, that's great, but not for me. And that's like a hard, it's a hard thing to realize. Cause then I go and I talked to my therapist slash coach about this and I go, does that mean I'm broken? And he goes, no,

it's not a good or a bad thing, it just is. So how are you going to act given that we know this? And that's been very powerful. - Yeah, one of the most impactful blog posts I've ever read is from DHH called The Day I Became a Millionaire. - Careful, careful. It's a lot of opinions. - A lot of opinions. - Yeah, yeah, yeah. - But that was a really good blog. So I read that when I was building my first business and back when I was making, I don't know, 40K a year from this business. And basically the thesis of this blog post is like,

DTH founded, for people who are not familiar, founded a company called Basecamp. And at some point many years ago, Jeff Bezos bought like a minority stake in their business. That's right. And both founders took like a couple million off the table or something to that effect. And overnight, this guy became a millionaire. And he writes in great detail about how like, you know, for about a day, he felt like euphoric. For about a week, he felt like there's a glow of like contentment.

And then it went straight back to normal. And he was like, huh? You know, he bought all Lamborghini. It's a bit cliche. He bought some like DVD box sets, bought a fancy TV. And then he realized actually the things that bring me joy are working on my business, programming Ruby on rails and like, I don't know, hanging out with the family and stuff. And I read that when I was in the pursuit of more and more money. And that I was like, okay, sick. That's really useful to know because I'm chasing these millions or whatever it was at the time. I think it wasn't even million at the time. That would have been inconceivable at the time. But it was so useful for me to know because it's,

it just was a firm reminder that the journey is the destination. And like, after reading that, I was like, okay, this is literally the confirmation I need to make sure I'm enjoying the process of building this business and not thinking that when I hit some certain arbitrary milestone that that will suddenly make me happy. Yeah. I think that's, that's also really good for like, if you're, if you're watching or listening to this, like,

What's great is you have the opportunity to design your life in the way you want. And yes, like maybe the magnitudes of certain things are really hard to achieve or luck or whatever it ends up being. But I think that finding out what you want, figuring out what that purpose is going to be and like working backwards from that, like there's some people that want that.

multiple super cars, multiple properties, all the same. And they genuinely want those things. They don't just want those things like, oh, I'd be nice, but they genuinely want those things. Well, if you work backwards, there are certain things you're going to have to do. Then there's certain jobs you're going to have to have, et cetera. But you know, if you just want like nice vacation home, a flat, all these other fun things, and you just want to like hang out, like,

you get a very different life. You don't have to go for certain things. Yeah. Um, and in a way, the less money you need to, to hit the kind of lifestyle you want, the more freedom you have, because you then have to just spend less time at work and you are then less limited in the things that you are able to do. Um,

I'm curious for you guys. So you guys presumably hang out with a bunch of super rich people. Uh, what are the common factors? We don't hang out with commoners. Uh, no, no. Yeah. What are the common factors between the ones who are happy versus the ones who are unhappy with loads of money? I mean, one of the first things that comes to mind, you referenced this would be, um,

if they weren't already there, a shift towards some sort of clear purpose. That's pulling them towards how they're spending their time. And in some cases, that got aligned super early and that actually helped create their wealth and so be it. In my case, I had to create a level of financial success for, I would say, more people

dark energy related drives to then create space for me to be more thoughtful and, and, and find something that's more purpose-based. And, uh, um, like I get a ton of joy for me on a weekend like this, like try to figure out how to,

help the group of people who are here level up, solve their problems, and then see the chain reactions of impact that that can have. So generally, is there purpose that's pulling them towards activity? And if there's not one, I can see a lot of darkness. Wealthy folks tend to not have an excuse not to be happy.

because they have extreme agency. So the folks that I know who are wealthy tend to be either

moderately if not majorly happier than my friends who are more middle class or even lower class or much more unhappy much more depressed than that like middle or or um you know lower class friends that i have and it's it's mainly because like you just don't have an excuse so like

Imagine you have the ability to get the help you need, get the joy you need, et cetera, and you don't. That not only has the impact of not bringing happiness, but also brings the resentment of like, I'm screwing up, right? It's probably similar. It's hard to maybe empathize with this, but it's probably similar to like, I know I need to write the paper. I know I should push forward whatever I'm trying to do to the task, but I keep looking at YouTube videos, right?

you have this, oh, I know I'm not doing it just after this video. And then you just get the self-loathing, right? Like, you know, thinking about that in an extreme way and consistently, you know, can be pretty painful. And I'm not saying you should feel sorry for them or anything like that, but like can be pretty painful. And I actually coped with some of this kind of existential, you know, thinking over the past year by doing a research study on wealthy folks. So I spent a bunch of money to like research

wealth and happiness. And I just wanted to figure out, does more money bring happiness? If it does, where does the happiness come from, et cetera? And the main reason I also did this was because there's a lot of those studies where it's like, once you reach $75,000 income, all of a sudden, there's not much marginal gain in happiness. The problem with that study is it didn't account for inflation, didn't account for location, and it also didn't have any millionaires in the study.

or had very, very few millionaires in the study, right? And that data is harder to get, right? And so, you know, I know a lot of, you know, folks who have some wealth, but also have money to get access to those from a survey or from doing research. And so that's what I ended up doing. And there were a couple of really interesting learnings that came out of that. One in particular is, you know, kind of as banal as some of the things we've been talking about, where folks who had wealth, you

if they kept their wealth or they gained wealth or net worth, they were a little bit happier if they kept it. They were pretty happy if they gained it. But if they lost some net worth, they were very unhappy on like a year-to-year kind of basis, which was really interesting. And then some of the other pieces that were fascinating was

Yeah, I have basically data up till about $3 million a year in income and then data up to about $50 million in net worth. And yeah, the person who has $50 million in net worth is happier than the person who has $1 million in net worth. Now, it's not as major as a change from that delta than the delta between a million and 10,000. That's a major, major change in happiness, but it does increase the happiness. And

Where does that happiness come from is naturally the question that needs to be answered. And the research that I've seen is there's a couple of layers that are increasing happiness over the baseline. The first layer was spending money on things. If you spend money on things, you will be happier than if you don't. Now, is that happiness sustainable, durable? Probably not. But then you can just buy more things, right? And that's typically what, you know, there's a certain character or caricature of a wealthy person that does that.

Now, one step above that, meaning increasing happiness even further above the baseline, was folks who bought things on specific segments of stuff that they cared about. So if you really, really like...

You know, Birkin bags, that's your identity, that's your hobby. Buying more and more Birkin bags increased the happiness or probably a better example, really like F1 racing. So you buy yourself, you know, obviously not an F1 car, but like your own little race car and you go to the track on weekends to race it. Those people were much, much happier, basically spending money on a hobby.

Above that, you started to get what we've probably all heard, spending money on experiences. People who spent money on experiences, hanging out like we have been doing, this brings extra happiness than buying things. But the top two were really, really fascinating. One that you've probably heard of right above experiences was giving. And it wasn't just indiscriminate giving, like the person calling you and giving the $10 or the $100 or whatever to the charity that called you. It was actually...

actively choosing, "Oh, we're gonna help the kids in our district have better laptops at school," or, "Hey, I really care about dogs. I'm gonna donate to the dog park so it can continue to sustain itself." That targeted giving increased happiness over things, targeted things, and even experiences. But the top one was really, really interesting.

And that was what we labeled after kind of looking at all the qualitative data, these freedom-inducing events, activities, or items.

Things like having a private jet increased happiness, not because it was having the private jet, but because you had ultimate freedom to just basically on a whim, go wherever you wanted in a very, you know, controlled environment. Things like having a personal assistant increased happiness even more than buying things and probably a little more accessible than buying a private jet, right? But these types of things. So even if you're making, you know, the $10,000 a month,

having a cleaner, cleaner home. That's freedom inducing. You don't have to do it. You probably don't want to do it. But it's one of those things where that will bring you more happiness, at least according to the data, than buying that extra bag that you probably don't need, even though that will bring you some joy and happiness. And so that study was really, really eye-opening. And this is how I cope with my anxiety is I do research basically. But it was really, really fascinating to kind of dig into. And the last thing I'll say, because I think it's interesting based on what we're talking about,

wealthy people actually don't spend as much money as you think they do. This was really eye opening to me because I was basically before the sale, my monthly burn or my monthly expenses was like $2,700, maybe $3,000 a month. And that included my mortgage, my food, food for the dog, living with Jenny, there was extra expenses, all kinds of stuff.

And then afterwards I was like, am I, am I enriching correctly? Am I supposed to be spending more money? Which I know is a preposterous thing to think, but there's a whole cycle that you get into where you're like, am I supposed to buy a Lamborghini? I'm not into Lamborghinis. Right. Which is like, again, very hard to empathize with. But what I found is, is like,

Even very, very wealthy folks, most of them are not spending more than $50,000 a month, which is a preposterous sum of money for most people. But if you're thinking about someone who has 100 plus million dollars, that's not a lot of money relative to how much wealth they have. And there's a lot of people who also, not as much, but there is a good amount of people who do spend more than $100,000 a month.

But the people who are spending millions a month and all this crazy wealth, they're making a choice. They're not necessarily the norm of wealthier people. Yeah, one of my coaches who I worked with last year, two years ago, we kind of landed on figuring out my sort of North Star core value, which was something to the effect of

the freedom to live, learn and teach on my own terms. There you go. And so any decision that takes me towards that I have found historically has been a good decision. And any decision that's taken me away from that, which has often been for the sake of making more money, I've often been like, oh, God, like this is actually not the thing

And so having that as a clear north star, and also, you know, often I ask myself the question of like, what's the decision I would make if money were no object? And I realized, okay, realistically, I'm making this decision to do another sponsored video, not because I want to make the video, but because it's a sponsored video. Okay, that's probably bad.

And with that, we have a sponsorship from... Exactly. Yeah, yeah, yeah. What have you guys seen that rich people spend money on that does not seem to buy them more happiness? Anecdotally and in some of the data, anything out of obligation, not only from a purchase perspective, but from a just activity perspective, typically reduces happiness. So

I joked a little bit, but also a little bit serious, like, should I buy a Lamborghini? Like, I don't like cars. It's not that I don't like cars, but I don't have a passion for cars. I admire them from feats of engineering, but like, I'm not like, it's not going to bring me joy every day.

But kind of keeping up with the Joneses, I could fall into a trap of being like, well, I need a nice car, right? Or like, I need to get the place right next to Matt's here in Cabo, right? That keeping up with the Joneses or obligation type purchasing typically reduces happiness. And that can go in lots of different ways. Like, oh, I have to go to this gala because I have to like see people or I have to donate certain money. Like you might think, oh, that'll actually increase happiness. But if it's out of obligation, it doesn't. And-

That also kind of goes into, you know, kind of the antithesis of the freedom point where that was another thing that showed up with wealthier folks is like, because you have the ability to have freedom, the whole obligation of like, oh, I got invited to this wedding, but I don't really want to go. That actually impacted wealthier folks from like a happiness perspective than less wealthy folks. Because you have this dissonance of like, there's no reason I really need to go to this wedding of this person that I don't necessarily know or like or something like that.

And there's so many other things that I could be doing versus someone who's a little bit less wealthy of like, well, I don't have anything else going on. So like, might as well go to it. So yeah, those, the obligation is typically very dangerous at least. And I've found that personally as well. The other thing I would quickly say is it's amazing how much lifestyle creep that you can see even after enormous wealth. We were talking this weekend about an individual who had a life-changing exit

done incredibly well financially and is currently in a role that pays them close to $10 million a year. And even in that situation, the lifestyle creep has gotten such that he feels like he can't leave because the money he would leave on the table

By leaving, lifestyle creep has gotten to the point where now he's eating into his principal in a level that feels uncomfortable. Fancy house, private school, team staff to look after the house kind of thing. Exactly. Where you're like, damn, 10 million is not enough. Yeah. And while that sounds absurd, I've unfortunately seen a number of examples of it and there's still a prison of one's own making.

Back to why I'm advising, can you get super clear about enough? Because then you've got massive freedom. I spent some time with Bill Perkins, who wrote the book Die With Zero. And I asked him, like, what's his best ROI purchase? And he said, couples therapy. And so I've started doing prophylactic couples therapy with my girlfriend. I also know from having read Die With Zero that I should spend more money on my health. And I just don't.

because it's like, it's like, you know, I'm young enough that like, you know, I'm not that fat and all that kind of stuff. But like, I know that in the future, when I look back on this time, I'm going to be like, dude, God damn it. Like, just make sure you're doing the workouts, eating well. Like there's no, there's no reason not to, but the, yeah, the pain is not yet sufficient. And I'm just trying so hard to project myself into the future to act in service of my future self. That's a great, I think that's a great answer then for yourself. And we felt this a little bit yesterday, right? Like we, uh, I, uh, practically got

a trainer to work a few of us out and we had had a full day. And the fact that that person was there and a few of us working out together, I think we all got more done, at least physically than we might have otherwise. And that's incredibly blessed, fortunate situation to have. But especially given the way that that probably will feed you as a creative and a teacher, I think that's a good idea. How do you guys feel about Die With Zero? Just the concept of, I don't know if you've read the book, but it

basically what the title is saying. I vibe with it. I mean, he's got the chapter about what about the kids? What about charity? And it was like, you know, give money to the kids when it's helpful, not when they're 68 and give money to charity when, you know, sooner rather than later because charities need money now. But beyond those two easy objections, I do very much vibe with the philosophy. I appreciated the reinforcement on

remembering the value of experiences and experience as a dad, like experiences with my kids that I won't get back. And as a reminder, I've only got like four or five summers left with them before they're like all out of the house. And that was a really useful prompt for me. - How do you, how do, okay, so let's think. So rich people that you know with kids,

What's the difference between the kids who are spoiled and the kids who are not? Oh boy. Like how do you not spoil your kids essentially? Matt's like, I did spoil my kids. I mean, I don't have a... One of the first things that comes to mind if I could observe a pattern, I think the sort of parental modeling plays a huge part in this. Like of, is there...

like lived, I think kids pay attention to your actions way more than your words. And so if you as a, as a parent are demonstrating hard work, humility, um, uh, treating people kindly, um, that's, um, you know,

Parents I've seen have done that. I'm not saying it's a perfect rule, but that's the biggest pattern that I've noticed. Whereas if they're sort of bad behavior and

you know, words are trying to be taught in another direction. Like kids pick that up. And, um, wait, there's a, I can't believe I haven't brought this up this weekend. The book that actually really helped me on this topic. I don't have kids yet, but help me with this topic and other preconceived notions of wealth was this book called strangers in paradise. Um,

It's basically written as an allegory where there's a sale of a company and there's three executives. One of them spends all the money, ostentatious, et cetera. One never tells anybody about it. They don't tell their kids about the money. They don't spend any money. It just sits in the bank account. And there's the middle, basically, who is the one that you should follow the balance. But in that, which we were kind of getting to, is...

There's this preconceived notion that like money ruins kids. And it's like, to a certain extent, that might be true, but it's not the money, it's the parents. And it's the values that the family has or expresses in the actions or even the words as well. And I think that's, that's the thing that I've at least found where I've seen

wealthy folks with kids and the kids are very spoiled. I've seen wealthy kids and spoiled in multiple directions, meaning they're overly hard on the kids because of the wealth or they're like pushovers because of the wealth. And then I've seen wealthy folks where the kids are like incredibly well-adjusted and it's just because the parents...

We're parents, you know? And so I think that's the factor that I think like, there's a lot of preconceived notions I had about wealth. One of them, oh, it's going to spoil the kids. I was someone who was like, they're not getting inheritance. We're not even going to pay for their college. Maybe we'll put money in a retirement account and they only get it at 55. So they can go do whatever they want, but their retirement's taken care of and that type of thing. And then as I like read this book and like met a lot of people and I've started to see basically what I was expressing from the book.

Nice. Thank you, guys. This has been a very interesting conversation. Any final tips for someone listening to this who's gotten to the end of this conversation and has been resonating with the stuff? I'm assuming that most people listening to this will have, are either students or will have normal jobs, but are probably aspiring to greater levels of wealth, or they want to listen to this conversation. So what would you say to someone who's maybe earning, let's say, 40K a year and aspires to be earning...

100K, 400K, 500K a year. Do the work to understand what you want and work backwards from there. I wish I had done that work similar to the friend that you suggested at 23. I wish I had done that in my early 20s. I don't know if I was capable of doing that work in my early 20s, but I wish I would have done. And then once you've worked backwards, try to get on the quickest path to learning.

and so what i mean by that is if you want to have a life of you know getting tens of millions of dollars there's only so many jobs or industries where that is even possible and so if you've done that work you want that and then you've looked at those jobs and you said yeah that's worth it or that is exciting and that's the type of outcome

Then the quickest path to learning is going and, you know, being a chief of staff at a startup or getting into a analyst program with one of the big finance firms or whatever it ends up being. But hopefully you're like, you'll realize that

oh, I actually want less than maybe I thought I did or the movie that I watched. And that just means I need to go be a private health doctor versus a public health doctor or some variation of that. Yeah. Very similar. I would say for me, the biggest step function change was when I was

Working at an entry-level startup job and started a side project that eventually got me across that $20,000 a month passive income threshold that enabled me to leave and start my business. That was my step function change in freedom. And I would...

you know there's a exercise in either for our work week there's a exercise that's very methodical to define this in tony robbins money book uh which just makes you pick a target and work backwards and get clarity and get to that first level and uh i agree like fi like learn um uh get yourself in a learning environment to um

develop the skills that give you the best shot to sort of get there. Sweet. Yeah, this kind of reminds me in Felix Dennis's book, How to Get Rich, which is a stupid sounding title, but it's a really good book. His thing is like, the whole thing is a very sort of sarcastic, irreverent approach to how to get rich. But his kind of conclusion is that like, you know,

get to your point of enough as soon as you can and then forget about money and do something better with your life like poetry or like I don't know hobbies and hanging out with your family and stuff and he's like of all the rich people I've ever experienced including himself like that seems to be the path to happiness find your point of enough get to it for him admittedly it's like 30 million but it doesn't need to be 30 million you know speaking to whatever however you define that point and I love this sort of find the quickest route to get there and then forget about money good stuff thanks Ali thanks for having us

All right, so that's it for this week's episode of Deep Dive. Thank you so much for watching or listening. All the links and resources that we mentioned in the podcast are going to be linked down in the video description or in the show notes, depending on where you're watching or listening to this. If you're listening to this on a podcast platform, then do please leave us a review on the iTunes store. It really helps other people discover the podcast. Or if you're watching this in full HD or 4K on YouTube, then you can leave a comment down below and ask any questions or any insights or any thoughts about the episode. That would be awesome. And if you enjoyed this episode, you might like to check out this episode here as well, which links in with some of the stuff that we talked about in the episode.

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