Prof G Markets - The Art of Spending Money

Episode Date: December 2, 2024

Scott breaks down the best and worst purchases he’s ever made, and why he prefers spending money on experiences rather than things. He also shares how his childhood still impacts the way he thinks about spending. Scott and Ed then discuss how to navigate spending in common situations such as dinners with friends, weddings, and the holidays. Ed asks for advice about how to prepare for the cost of having children. And Scott also explains why it's important to make sure your spending lags behind your income.  Order "The Algebra of Wealth," out now Subscribe to No Mercy / No Malice Follow the podcast across socials @profgpod: Instagram Threads X Reddit Follow Scott on Instagram Follow Ed on Instagram and X Learn more about your ad choices. Visit podcastchoices.com/adchoices

I'm Ashley C. Ford and I host Into the Mix, a Ben and Jerry's podcast about joy and justice produced with Vox Creative. For the past few years, I've seen a lot of hand-wringing about Governor Ron DeSantis's agenda to end what he calls woke indoctrination. But we wanted to know, what does that mean? And how does this agenda actually affect the people living and working there, especially those who have benefited from the diversity, equity, and inclusion programs that DeSantis' policies would uproot?

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speed of the world's most experienced cloud. Today's number, $91 million. That's how much King Charles III's coronation cost British taxpayers last year. Ed, what does Burger King and vaginas have in common? What's that? It's generally considered bad form to eat them in the lawsuit. That wasn't easy to bring Burger King and the King into something this profaned.

And you're pretending not to laugh for fear that you'll be named in the lawsuit. I don't get, you can laugh out loud. That's right. Even Claire is laughing. And Claire is literally the general consulate of Locustan. I always laugh at your pussy jokes, come on. She does.

She does, Claire's down with me. We're both looking for the same thing, if you know what I mean. That's right, that's right. Yeah, we're both on the same team. We both point out the same accouchement. We're looking at the same, we're seeing the same sights together on the road.

All right, I need to get out of this. Ed, what are we talking about today? We're talking about, what are we doing today? We're doing something different today. Here, you take this. Gladly. Well, we've got a special episode today, we're talking about what are we doing today? We're doing something different today. Here, you take this. Gladly. We've got a special episode today, Scott. We are diving into one of our favorite topics.

We're not going to be talking about saving money or even investing money. We're going to be talking about spending money. We're going to be answering questions like what are the best ways to spend money? How should we think about spending? And most importantly, how do you spend your money? So I'll walk us through a series of questions about spending. You'll give me your honest answers, I hope, and then hopefully we'll learn something along

the way. This doesn't fit my opening joke. I think we might have to re-record. This sounds very thoughtful and responsible anyways, but yes, I'd please continue. It is going to be very thoughtful. It's, it's, it's practically going to be a therapy session. Yeah, I'm in. I'm in.

All right. Well, we'll start with a pretty easy question. And that is what is the worst purchase you have ever made? Oh, um, when I was, I grew up in California and I grew up in this era that you don't relate to to it was kind of California dream and American graffiti The only thing you had to express any sort of coolness or wealth or aspiration or macho was your car in addition Living in Los Angeles you had literally no aspect of a social life

Unless you had a car there was no public transportation. There was the RTD, but it wasn't really efficient. So if you wanted to go to Friday, you know, on a Friday night, go and crash a party that someone was having, you were invited to see above Scott Galloway. You needed a car. And so from the age of about 13, I saved pretty much everything for a car. And I got, my dad gave me an old Volkswagen Rabbit from his old home in Phoenix. On the way back from Arizona with a friend, the tire blew out and there was no spare tire.

Gives you a bit of a sense for the protective instincts my father did not have. Bought a Renault La Car. And finally, I think the Renault got towed my freshman year in the fraternity and I didn't even go get it. I think I just let it be sold for scrap. So buying a car, my first cars were the worst purchases.

Hands down, I ever made, they literally took all of my disposable income and more. It was like $2,500 to buy insurance when you were 16, which on an inflation adjusted basis, probably meant $10,000 a year. I did not have that kind of money. And yet I found it. So hands down, the worst purchase I ever made was, uh, was a car. What about the BMW you got after you got your bonus from Morgan Stanley?

I'm always kind of blown away by the fact that that's how you spent your bonus. I respect it to be clear, but, Oh yeah. And all of that. I think I told you, I think I, I bought a three 25, I Navy blue. I bought it off out of the recycler. I think I spent, I forgot what it was. My first bonus was like 25 grand.

I spent 28 grand on a car. But I think of that, I mean, this sounds dumb, but a bad car that you don't need in college and high school, I kind of needed it, but I just couldn't afford it. You know, that's a dumb purchase. I would argue that when you're 23, working a Morgan Stanley and you're in your mating years, that buying a BMW and hanging swim goggles

from the rear view mirror, it makes a lot of sense. You're trying to signal the women that if you have kids with me, your kids are more likely to survive than if you date someone who is driving a Hyundai and does water aerobics. So I empathize with what I'll call

smart signaling purchases. I think it's difficult to lecture someone your age and does water aerobics. So I sort of, I empathize with what I'll call smart signaling purchases. I think it's difficult to lecture someone your age on to not occasionally buy cool shit and do cool things. Your 20s come and go, you want to signal attractiveness. I get sort of the irrational purchases. To me, the BMW kind of made sense. And also I sold it and it paid for my European trip.

So it was worth it. And I don't think I lost so much value on it. Yeah. My follow-up was going to be, was there ever an item that you splurged on that seemed pretty irresponsible at the time, but ultimately, as you reflect, turned out to be completely worth it? Perhaps the BMW?

Perhaps something else? No. And I'll turn this back to you. But I wish I'd learned earlier. And I did learn it accidentally, but it was more organic than anything I read. You remember experiences, you don't remember stuff. People overestimate the joy they're going to get from things and they underestimate the joy they're going to get from experiences. When I left Morgan Stanley, I initially, towards

the end of Morgan Stanley, I thought about trying to do a third year and maybe making the jump to associate or interviewing with another firm. Cause everyone had convinced me that if you have your foot in the door in investment banking, you never want to leave because you'll never get a job that good. Even this, even though, despite the fact I hated it and they hated me, I wasn't very good at it. I was trying to figure out a way to maybe stay in

it. And then the only time I've ever been in the hospital was I got an arrhythmia and towards the end of my second year in a, what an arrhythmia had something called ventricular tachycardia, which is an irregular, irregular heartbeat. Okay. And the timing was, was really unfortunate because

the week before this guy named, was it Hank Gathers, the best high school or the best college basketball player, uh, got a rebound, went down for a monster jam in front of a national audience and then turned back to run up to court and drop dead on the court. He was diagnosed with VTAC and an enlarged heart, which is quite regular for people who, your heart is a muscle and if you work out a lot,

which I was doing in crew, your heart actually can get too big for your chest cavity and it can create an electrical imbalance. I was overinsured. I was having this irregular heartbeat. Hank Gathers the week before, they stuck me in the hospital. So while I was in the hospital, this woman, I was at St. John's, I think it was, and she said, why are you, she looked at me, you know, I'm 23, said you're in the ICU unit of the

cardiology unit. She just looked at me, not a doctor, and said, you shouldn't be here. What's going on with your life? And it hit me so hard. I became very emotional because I'd obviously tried to push down all these emotions about how fucking freaked out I was that I was in the ICU unit of the cardiology unit at St. John's.

And basically, net-net, that afternoon I decided I was gonna leave investment banking and do something different. I moved back in with my mom and I sold my car and I went to Europe with that money, with my friend Lee Lotus and we got a backpack, a U-rail pass, and that still remains as evidenced by anyone who watches this podcast.

I do amazing travel. I travel to the best places. I have an extraordinary life with respect to travel. The best trip I've ever taken was when I was 24, right out at Morgan Stanley with the U-Rail Pass, sleeping in hostels with my good friends. Lee Lotus and then David Kingsdale joined us and I connected with a woman I was dating at the time

and to be in, you know, McInnes on no money, but with someone you were into, that was just the best expenditure I've ever made. And I spent everything and more. I think I had to call my mom and ask her to wire me some money, but it was hands down the best expenditure I've ever made. So I'll put it back to you. The dumbest and best purchases you've made today, other than like a big wheel and

that glass dildo I saw you had on your shelf. Turn off the camera. Jesus Christ. I'm sorry, go ahead. No, that one was worth it. Yeah, I think it's experiences for me too. It's funny. The first thing that comes to mind for me is also Mykonos.

There was one night in Mykonos, I went last summer with a bunch of friends, and there was one night, it was probably the most amount I've ever spent in a single night, And it was ridiculous. We decided that, you know, we had picked out what the best club on the island was, and that club is Alamogu. And we decided, okay, me and my boys got together and said, okay, we're going to pay for this

whole thing. We're going to get all the girls and they're not going to pay a penny. And we're going to just spend like crazy on this one night. On Thursday night, we're going really, really hard. And so we got the best table at the club. We got one of the biggest bottles that they have on offer. Um, and we kind of just decided like, this is, this is our big night. And, you know, I turned, we're having a great time.

I turned to my left and we're in the VIP section sitting next to the table that is occupied by Paul George, Carl Anthony Towns, and basically just all of the biggest NBA stars in the world right now. And that was a moment where it's like, okay, this is, this is the amount of money that I don't have clearly, but I've made a very intentional choice and an intentional decision. Like this is something that I know I'm going to enjoy. I know it's going to be special. We had, we stayed up till sunrise. It was like the greatest night ever.

And that to me is like a moment where it was very irresponsible when you think about it numerically, but in terms of like the intention and the purpose behind it where I was like, I know that I'm spending a lot right now and I'm going to be very responsible when I get home to New York. That was probably my number one. It's funny, it reminds me of my dad occasionally would say something that, you know, was close to insight and he always said to me, doing nothing is fine as long as it's planned. And I remember another saying that anger is anger is actually a productive emotion as long as it's planned. And I remember another saying that anger is actually a productive emotion as long as it's planned.

And I think what you're saying is you made a responsible decision to be irresponsible. And I think that's okay. You know, occasionally it's fun to splurge and, you know, I would argue the splurges when you're young are, I think you remember them more, especially if they're around experiences. Anyways, my advice to young people, you know, Andrew Huberman and Peter Attia will say, you know, don't drink alcohol. I don't see drunkenness. I see togetherness.

And I just love the image of you and your homies in Mykonos doing your thing and then late at night getting shut down by every woman in the club. Still, it was worth it. That was definitely worth it. What about the best purchase you've ever made? Probably the best purchases both financially and emotionally for me were homes. That is right out of business school, I was very much in love and we bought a home together.

And it just represented like a commitment to each other. And we got a dog and it just, at the age of 27, it just felt really nice to have some of that feeling, that domestic bliss to be committed to someone, to be making a mortgage payment and owning a home. And the home was just a vehicle, I think, for kind of that commitment to each other. And it felt really, it was emotionally very rewarding. And then going back to the last house purchase I made,

when I sold L2, I had a big windfall. And my partner said, we should buy this beautiful home. I mean, it is a beautiful home on the beach. And one of my flaws, many flaws as investors, I think nothing is ever cheap enough. And the home was, they were asking 15 million. She said, trust me, we can get it for a lot less. I'm like, she offered, ended up getting it for nine and a half. And I'm like, I didn't want to buy it.

I'm like, no, it'll be worth six and two years. We're going into recession. This is 2019. I'm sorry, no, it'll be worth six and two years. We're going into recession. This is 2019. I'm sorry, 2017. And it took three years to renovate shit ton of money. And then COVID comes and we have, uh, you know, a really nice home on the beach. And then again, see above better to like, be lucky than good. This mass migration of people to Florida from COVID, all these masters of the universe who all want to live

in the same area and beyond the sand. And that home has probably doubled or tripled in value. And more important than that, in an environment where people had to sequester and isolate with their families, I was in a beautiful home, more time with Netflix, more time with my boys, and my stocks were skyrocketing.

And COVID was in my opinion, the most unfair, pornographic, gross transfer of wealth and health from the already wealthy and the incumbents from people who were unhealthy or poor. And I was, I was on the right side of that. And it just strikes me, it just feels so uncomfortable to say COVID was the best two years of my life. But this is a long-winded way of saying the best purchases

I have made, and I'm not suggesting that it's right for everybody because a lot of it is timing, but emotionally and financially, the best purchases I have made were my first and my last home. Will Barron Are there any categories of spending that you kind of refuse to skimp on or that you pretty consistently go all out on? Something where you look at the price tag and you say, doesn't matter, I'm going to

buy this no matter what. I'm sitting in a room that costs $5,000 a night. I mean, enough said. I don't own a car. I don't spend a lot of money on clothes. I spend a crazy amount of money on travel. The next door in the next room is my friend Augusto. And Augusto is like this greatest guy, easy going, super nice. And when I'm doing a lot of traveling and I'm lonely and my partner can't come with me or my kids can't be with me, I call one of many friends and I say, come join me.

And if it's not easy for them, logistically or financially, I make it easy for them. And we go out and we go to the best place. I mean, and I feel self-confident. It's so funny. I've always, I've self-conce- it's so funny. I've always- I've had this weird shame around money. Up until the age of 30 or 35, I was ashamed that I didn't have more money.

I was always- I was broke because I was in school, I had student loans. I was really self-conscious about how much- how little money my mom and I had. It made me feel very insecure. And then student loans, starting businesses, never had enough money, even when my friends were starting to make money. So I didn't have enough money.

I was embarrassed by that. I think from about the age of 30 to kind of 45, I had just the right amount of money. I had enough money to do nice things, but I wasn't self-conscious. Then I got exceptionally lucky. And by the way, I'm not humble. I think I'm a f*****g monster. I think I'm exceptionally talented, but I also got really lucky. And by the way, I'm not humble. I think I'm a fucking monster. I think I'm exceptionally talented,

but I also got really lucky. There are a lot of exceptionally talented people out there. And now I'm not embarrassed, but a little self-conscious by how much money I do have. And you're not supposed to talk about it. And I think that is nothing but a bullshit construct to keep poor people poor. Because when you speak a different language,

rich people talk to other rich people about money all the time. They talk about taxes, they talk about investments and they get more literate. And then we're told not to talk about money in case you decide to share your salary with someone else or you figure out how much money I have and decide to fucking, you know, show up with a guillotine or actually vote for people who have a progressive tax structure or maybe demand more compensation because you realize the person down the

desk from you is making 30% more because they've been there 10 years or their different sexual orientation. I mean, basically the asymmetry of information and this inclination that you're not supposed to talk about money keeps the financially illiterate illiterate and also keeps rich people richer. So other than bragging, it is, I think,

important to talk about money, even when you have it, but hands down where I go ape shit with money now that I have it and spend more than I should is on travel. I'm going to Africa. I'm taking my sister and her family and they didn't want to go. They have responsibilities.

Their kids in choir, they're working hard and I'm called her and I'm like, you're going to Africa, I'm taking my sister and her family and they didn't wanna go, they have responsibilities. Their kids in choir, they're working hard and I'm called her and I'm like, you're gonna be dead soon. When are you next going to Africa like you're gonna go with me? When are you gonna roll into Africa like you're gonna roll with me? What the fuck are you thinking?

And that was the right lecture for me to give my sister. These experiences, if there's anything the research shows around spending money, it's the following following drive a Hyundai and take your husband to Africa. I don't really buy a lot of things. I'm not, I'm just not into that. I don't buy stuff. Do you look at the price tag much when you buy things? So if you, I don't know, you walk into a nice clothing store, are you

thinking about how much it costs? I do because I can't get out of that habit. I was in, I forget where I was, but there was just an insane price on something. And I'm just like, this is offensive. I can't, I can't bring myself to spend money on this thing. It's just, you know, I'm like, that's just ridiculous that you would even try and charge this amount of money. I can't buy it.

I really need it. I really like it. It doesn't make any difference to me, but I, there's that part of you.. I can't buy it. I really need it. I really like it. It doesn't make any difference to me, but I there's that part of you. You just can't do it. You just, you remember back when you didn't have enough money and you establish a value system and you're like, I just can't do it. I can't, I can't, you know, I can't spend this kind of money. What do you think is the difference then?

What do you think makes justifies like a good purchase versus a bad purchase? Like this is the majority of people, 99.9% of the planet doesn't have these problems. They, they have a much bigger problem. And that is they're constantly trading off needs versus wants. And that is the majority of our planet, I think only about one third of the planet are consumers. What does that mean? It means that they have enough money to buy things beyond basic food,

shelter and education. So only a third of us even get to make these decisions. So do I want a scarf or do I want to go to McAnose or do I want to take my spouse out for a nice dinner? Yeah, it's, I think you're in a unique position because you have experienced pretty much every economic class there is to experience in a way. I mean, you haven't experienced real poverty, but you did not grow up wealthy and now you're

extremely wealthy. And the way I kind of think about like, you talked about there are certain people that can't make those trade-offs that we're describing. It feels like there's a progression when it comes to spending. It's like in a certain economic weight class, you can't make trade-offs because you have to survive and you have to get by. And then you, there's another class, which is you start being able to make trade-offs. And then there's another one where I feel like you are where it's like, you don't

even really need to be making trade-offs that much. I mean, it sounds like you can generally speaking, have your cake and eat it too, in most situations, I would say. So what I would be interested to know is like, how has the psychology of spending money changed for you as you have breached each of those economic weight classes? Like, did spending money take on a different gravitas to you as you got richer or as you got poorer? So I think it's important that everyone have a certain code or values that they want on their tombstone and then try and live their life across those two or three values. And one of my values is I pride myself on being generous and I'm

generous with everything, but my time. I like spending money on it. I like treating people. I like buying things for people. I know that's virtue signaling, but anyone who knows me knows that is true. And the reason why is not because I'm, I have this inner nobility. It was because I was deeply traumatized by my father's relationship with money. My father was born and raised in depression era Scotland, where you could

literally starve if you didn't have enough money. And so he was painfully cheap. He was the guy when my parents were divorced and he came and took me and my friend, best friend, Adam to see Greece. Amazing movie in 1976. After the movie, he collected two bucks from my friend Adam, because he had bought the tickets.

I had to sit there and watch this go down. I went to Hawaii once with him on a big golf vacation, or he was the crown-circled ITT Salesman of the Year, and he got to go on this golf trip and take his family. We went to Baskin and Robbins, they got ice cream, I ordered a shake. And then for two days, my dad didn't speak to me. And you're 13 years old and you're a guy and you're looking up to your father and you're like, why is my dad not speaking to me?

Like just ignoring me. And finally I asked Linda, his third wife, my stepmother, a wonderful woman, I'm like, what's going on? Why is dad mad at me? He's like, he's upset you ordered a shake at Baskin and Robbins, it costs $3 and you didn't ask him. My dad didn't speak to me for two days. And so when my parents got divorced, he immediately

went to the upper middle class. We immediately went to the lower middle class. He was so awful to us financially. He could have made our lives so much easier with just a little bit of money. I really struggled in college and I like to think, Oh, Bill grit bullshit. It was really fucking stressful.

Not knowing if you were going back to college every summer and he could have made my life so much easier. And so I remember just explicitly and implicitly deciding if I ever have money, I am not going to be this guy. I mean, and I can't stand it now. I can't stand, I have friends who are really wealthy.

Who always find reasons not to pick up the bill or what I, and I just find it such a grotesque attribute and some of it is them, they're just responsible. They were just raised that way. I, I find being cheap, one of the grossest attributes, especially for men, I'm sexist this way. I just, I can't even be around these people. If I, if every one of my friends isn't fighting over the bill, we're not friends.

But my, my spending right now in large part, or some of it is, I'm just, God, I just don't want to be my dad. He was awful with money, just awful. And I always thought if I ever have money, I'm not only going to enjoy it, I just don't want to be my dad. He was awful with money, just awful. And I always thought, if I ever have money, I'm not only going to enjoy it, I'm going to share it. Yeah, I feel like people don't seem to understand

how good it feels to be generous. I think I started only sort of to realize this recently, that it does actually feel really, really good to get the check and give someone a nice experience. I mean, I did that recently with my dad for the first time and it felt like this sort of exciting, important moment where it's like, no, I can get this. I can give to you.

And yeah, I mean, it sounds so trite when you say it, but the reality is just as you say it, it's like, it actually just makes you feel really good. And it's almost the same as getting something for yourself. It's all, as you say, it's all, it's selfishly motivated. It makes you feel good, but it seems like, I've just found, I'm surprised by how many people don't realize that, that like it's really enhances your life

and your own personal experience to be generous. There's all sorts of different ways to garner emotional reward from money if you handle it well. You know, money is nothing but the transfer of time and work. And there's few things you can do that are more generous than give someone time and work. I was a services, I used to park cars, I was a waiter. I remember I was a waiter in the Mondrian Hotel

and this lovely old lady was a character actress. I forget her name. Every time she was there, every time I would walk by, she'd put five or 10 bucks in my pocket, like literally every time I walked by her table, she'd come over and she'd like slip five or 10 bucks in my pocket. And you're going to UCLA and you can barely afford your books. It like changes your fucking day.

It's like nice old lady gives you 30 or 40 bucks. I mean, it's the difference between being able to go on a date or buy lecture notes or whatever it is, it is wealthy people who do not tip big. That makes just absolutely absolutely no sense. It is so easy to give in a liquid economy time and work to people by giving them money and it has nothing to do with nobility or ethics. It just, like you said, it just feels really good. The other thing that you inspired is that I think

even more, I love spending money. I am really good at it. It's one of my core competence. I'm outstanding at spending money. I'm, I always say I'm spending money like a gangster in the fifties, just diagnosed with ass cancer. I am just, I am just going large and I'm loving

every minute of it. I'm really good at it. And it creates a lot of joy and happiness for people near me and around me and for me myself. I do think though that even more rewarding than spending it or having it was making it, specifically making it with someone else, both professional and personal partners. My ex-wife and I, we were working so hard, we were trying so hard, we were making good money,

we had setbacks and then, you know, I had businesses fail, I had businesses work, she got promoted, she didn't get promoted, but we were saving money and we bought a house together and we started saving money together and we really built economic security together and it was just so rewarding to do it with someone. And then where you also get a lot of that reward is, let me be clear, the

businesses I've started and sold, my first obligation was to, for me to make the most money and I always have. That felt better than anything, but it also just felt fucking awesome to bring in really good people who'd worked really hard with you alongside of you and go, hey, I know you're 27, but you're gonna make $550,000 next week when this transaction closes. And them just looking at you like they couldn't believe it.

You know, like I get huge reward out of underpaying you. No, but look, no one ever feels overcompensated, but for the last 10 or 15 years of my life since I've gotten wealthy, I've made it objective to say, okay, what is this person's market rate and how do I pay them 20, 30, 50% more than market? And it just feels good. So building, spending it is great, but I found actually the making it, specifically the making it with other people was actually the most rewarding part.

Yeah. Wow. I 100% agree with that. I think that's one of the things that makes relationships so fun is that you're building something together. It's just so much more exciting than doing it on your own. Well, by the way, it just dawned on me that it's no accident that you've asked me to do all this virtue signaling around generosity right before bonus season.

It's clear that everyone has figured this out. And there's like eight people on this line taking notes that reviews are about to come out. You know, I find it's- It's so great to give money away, isn't it? I find it's all about grit and helping people realize their inner child and save by not by underpaying them. That's how you build character.

I'm planning to build everyone's character here. We've got more after the break and by the way, we'll be recording an Ask Me Anything episode very soon. So please send in your questions for me and Scott to officehours at profgmedia.com or leave a comment on our YouTube channel. We'll be right back. Look. Support for Profit Markets comes from fund rise. Venture capital is widely seen as one of the most lucrative asset classes in the world. Go look at the S&P 500. Nearly every major tech company on that list was once funded by venture capital firms, producing billions of dollars in profits in the process.

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I'm going to go through some individual situations where spending is very important and I just want to get your reaction on how you would deal with these little situations I've come up with. So the first one is restaurants. You're out to dinner with friends and let's imagine you're not as wealthy as you are right now for this. One of your friends orders a really expensive bottle of wine. They order like a bunch of plates for the table.

And then when the check arrives, it's way more expensive than you thought. It's one of those checks where you see it and you start to feel kind of anxious and uncomfortable. You don't really know what to do. So what would you do? Would you still offer to get the check? Would you split it equally? How would you handle that?

Is this a group of guys or just friends? Group of guys, friends. I mean, I roll with a different crew. I just don't, we were, I never had friends that were into fancy wine until I got rich. And now I have friends who are trying to like inject class or some air of prestige into their life by ordering stupidly expensive bottles of wine and buying art. If you want to talk about, you know, if you want a signal for someone with a little dick, find someone who's all of a sudden really into art and, or, you know, orders, orders,

anything above a hundred bucks a bottle, a bottle of wine, unless you're really, I mean, if you're really into art and you're really into wine, fine. My friend, Adam is really into cars. He buys expensive cars because he's always been really into cars. Fine. Fine. I get it. But if someone ordered an expensive bottle of wine and I was with a group of guys and we didn't have a lot of money, I mean, okay, if he's a baller and he's paying for it, the general form is the following general, general like manners. If you order an expensive bottle of wine,

it means you're paying for dinner. You're basically signaling, I am going to pay for dinner. You can't be generous with other people's money. And then when the check comes, if it's a group of guys, your age, you're all friends, you all split the bill unless someone went crazy in. What about, what about if you're like in your thirties, like it's, it's, it's not as absurd to be in your late thirties, everyone's making good money. Maybe everyone's with their partners.

Like, what do you do in that situation? I personally feel like with friends, I mean, young people split the check or whatever it is, Venme or send me a request. I get it. Right. I think if you're in your thirties and you're blessed with some reasonable economic security,

general format should be the following. We get this one. Oh, the next one, they get it. And if people aren't, if things aren't kind of evening out over time, you have to decide whether you want to stay friends with these people because, you know, generally what I have found is that you're out with couples. I can't stand splitting the check. I'm at a point now where people say, oh, you did this.

I'm like boss, either pay for it or I'm paying for it. We're not splitting the check. We're fucking grown men. It's just, and I'll get this one. You get the next one, whatever it is. And especially when you're out with couples, I think you're mindful of each other. But for the most part, I think one couple gets the check and then the other couple gets the next one. I don't, I think the moment, I think it's always that strange moment when the bill comes.

I think it's awkward that strange moment when the bill comes. I think it's awkward. It's very awkward. But it should all come out on the wash. If you have good friends, they're not going to be stupid in terms of over-ordering. And you'll realize that you trade off two or three couples, two or three friends. And if they, if, if their turn never seems to come around, you call them out on their bullshit and be like, Hey, how come

you never see, how come you always seem to find a way not to pay? Okay. This one's particularly relevant right now. Christmas is around the corner. Let's say again, you're in your late thirties. You've got like two children, a partner, two parents, you got aunts, you got uncles, you got friends, Godchildren, etc. Who gets presents and how much do you think you should be spending on those presents? And do you spend more on one

person? Do you spend less on another person? How do you think about presents and Christmas as it relates to spending? I think about Hanukkah, you anti-Semite. Hanukkah, sorry. Okay. Actually, that's not true. The holidays. I think about Christmas. I don't know. Hanukkah, sorry. Okay. Actually that's not true. The holidays. I think about Christmas. I don't even know what the, I don't know what Hanukkah is. This is personal, how your approach is spending the holidays.

When the kids were little, it was fun to just buy them a ton of shit and have this consumer orgy that morning with a wrapping shit and then playing with it for two minutes. And that was fun. As we've gotten older, what I do with my boys is they make a list of stuff. We try and connect it to George or something or something, and we, we pull stuff off their list and maybe we wrap one or two gifts. We just don't, I don't want that kind of consumer Lollapalooza in the morning.

And then with my partner, I ask her to, you know, occasionally we don't buy each other's stuff around the holidays or for birthdays. I buy her stuff randomly, because I think it's just more fun that I think she'll love. And she drops hints every once in a while. That she wants something? Oh, yeah. As in, I've been looking at this, or it's like, you haven't given me a present in a while. No, she'll send me an instance. She'll send me a photo of a Birkin bag with the exact color and be like, Hey,

what do you think of this? I'm like, okay, message received. And what I try and do is wait just long enough such that she forgets about it. And it's a surprise, but yeah, I'm not a big, I'm not a big gift giver. I don't want, I don't want gifts. The gifts I like, you know, for me, I want meaningful gifts. I want, you know, my sons will write me a note or they'll get me a book that was meaningful to me.

All that gets a picture of us framed. That's the shit I want. I can buy anything I want personally. And I don't, I'm not into stuff. You know, the gifts that, I mean, it sounds like a Hallmark commercial, but I don't, I don't want stuff. I don't want, I don't want automatic tie rack or a

cream shave heater. That's what we got my dad. Ooh, was he thrilled. Back in the seventies, you put shaving cream in shave heater. That's what we got my dad, who was he thrilled. Back in the seventies, you put shaving cream in a heater and you'd have, you'd have the delight and the supple feeling of warm lather on your beard. That's a great idea. I'm probably going to get a rotating tie rack.

I have so many ties. I need to, I need to see them electronically whizz by me. I love that too. We're not big, we're not big gifters. So who gets presents then? This is a question I've been thinking about. I can't tell, or it's not totally clear to me who I'm supposed to be getting presents for during the holidays and also how much we're supposed to be spending. First and foremost, your boss. Yeah, okay. Because I will say, by the way, you get presents for us

at the end of the holidays. I don't know if you know what you're getting us, but we have received Christmas gifts from you and I would assume that that's sort of part of, you know, you build that into the budget, okay? Over the holidays, I need to put aside this amount of money to get my employees some gifts and to get these people gifts. I feel like it's an important part of the, the income statement, if you will. But it's strategic and it's selfish.

So employee gifts and it's the following. First off, I don't buy anything. I don't know what it's going to be in that fucking bag. MJ, who has much better taste than me. She does a great job. She'll say, I'm going to spend 500 or a thousand bucks on employee gifts per person. Like fine. And she'll figure out the latest cool thing and she'll do a great job and

merchandise it. And I just give her my credit card number. And the reason it's strategic is that if I spent a thousand dollars on a gift or gifts for employees, it's worth more than a thousand dollars. If I gave them a thousand dollars in compensation, one, they'd have to pay 30, 34% taxes on it. Whereas if I give you a thousand dollars, or whatever, AirPods and a scarf or something, it's pre-tax income. And also it's more meaningful. The psychological benefit is greater than if I'd just given you a thousand dollars cash. My first business partner would always be like, he was totally gruff. He'd be like, just give them cash. And I'm like, no, they like gifts. The kids like gifts.

For me, the holidays, I can't stand the holidays. They were not an enjoyable time for me growing up. So I literally loath them. It's so personal though. You might find, I mean, so for example, I think gifts are more important for women. Cocaine, jewelry, cocaine and jewelry, women have a special relationship with that.

And maybe you don't like cocaine. Maybe you don't like cocaine, maybe you don't like jewelry, but if you don't in your 20s offer that to women and in your 30s and 40s offer jewelry to women, you are not a good person. And mostly the jewelry. Like I can't ever imagine spending, oh, I guess I buy watches now, I never used to buy watches, but I can't

imagine people spending this money on jewelry But you've got to determine what's important to the people in your life That's what it means to be generous is you're doing something for someone else you wouldn't do for yourself It makes no sense to you, but it makes but it's important to them. So you do it for them Do you think that people don't value gifts enough? What I have found is that, and I wish I'd figured this out earlier, writing somebody and complimenting them and recognizing them, or telling them you were thinking about them or telling them how impressive you, you, you are with them or, or taking the time to say, you know, you handled

this situation so well, or congratulations, this is just such a, this is such a nice achievement for you. Or taking the time just to recognize their achievement in a very thoughtful, explicit way, especially men to men. I think that's the best gift you can give another man. My best friend, Lee, on a regular basis, he will text me when he, I get choked up thinking about it. He'll literally, he'll literally text me. He'll say, me and my parents saw you on, on Bill Maher and we're just so proud of you. Yeah, that is so nice.

Those are the gifts. Like, and everyone's different. Maybe people like stuff. Like that's the, you know, that's the shit I remember. And wouldn't you know, my friend Lee is gay and I think gay men have an easier time expressing their emotions than straight men. And, and, and just registering how important and meaningful that stuff has been for me has helped me be much more generous with my emotions. But in my opinion, that's true giving. We'll be right back after the break. If you're enjoying the show so far, hit follow and leave us a review on Proffjee Markets, wherever you get your podcasts.

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Autograph Collection is part of the Marriott Bonvoy portfolio of over 30 hotel brands around the world. We're back with Profit View Markets. I want to move on to some things around what is essential to spending, like what kind of things in your life you find essential. I mean, we talk a lot about like discretionary versus non-discretionary and the technical definition of non-discretionary is like the stuff you can't live without. So, you know, food and housing costs and health insurance, et cetera. But I can imagine that as you get richer, that category sort of starts to expand.

Like, you know, I sort of feel like I can't live without an iPhone at this point. Like that's sort of the way I think about it. So I guess my question for you is like, what stuff can you not live without at this point? What do you have to spend on? And what is your approach to spending on those items? Michael O'Brien This is going to sound under the title of infinite douchebag, it would be really hard to lose my plane. I've gotten very used to having a plane.

So, I mean, there's something around ramping or spending behind making sure you're spending lags your economics because it's the joy you get from having something isn't as great as a disappointment if you lose it and can no longer do it. You get used to this shit really fast. So when I bought a plane seven years ago, the best piece of advice I got was a friend of mine who said, just make sure you have way more money than you need for this because

you do not want to give it back. He's like, don't buy it until you know, you can, you can keep it. And that was what's so been so rattling about being rich and then poor and then 2000 being rich and then poor again in 2007 and 2008, because to kind of step backwards and I didn't really actually, I didn't step back materially because I'd never, I was lived below my means, but you step back from an emotional security standpoint, that is really frightening. Yeah, I was going to ask, like, have you ever sort of downsized your lifestyle because you just couldn't

afford it anymore? Yeah, I did. And after the great financial recession, hit in 2008, I had a loft in New York. I had to sell that. I just didn't have any money. I wasn't making any money and all of a sudden I was had negative net worth. So I had to sell my loft. That was very disappointing. I loved, it was kind of just humiliating to be whatever I was 43 and have to sell my house to pay my bills. I was never in debt.

Will you with a partner at that point? No, I was single at that point, but it still felt really fucking humiliating. Um, so yeah, I've had to step back and I think most people have to step back at some point, maybe, I mean, if you're really responsible, hopefully not. But I got crushed. Yeah. I feel like that's a really, that's a big one for me. Just the prospect of downsizing it for the way I have it in my head right now is like, I'm doing forced savings, so I'm good.

I'm being responsible. How are you doing that? How are you doing forced savings? I have the automatic 5% that goes into the 401k and then you match that. And then I'm also just immediately, when I get at the beginning of the year, I just take a chunk of cash and just put it in the IRA and that's the end of it. I just want to say you're like light years ahead

of where I was when I was 25. I just, I wasn't even thinking that way. And part of the reason I do that is like, I want to spend a lot and this might sound dumb, but I like nice things and I like nice restaurants and I like going out to cool places and I spend a lot of money on all of those experiences. And part of it for me is that I want to kind of surround myself in that world and get myself deep in that position such that I have no choice but to go on and make a lot of money. And I think the scary thing for me is the idea that at some point, you know, this podcast

stops being successful and I sort of find myself at a crossroads and suddenly I can't do all of this anymore. I can't live this cool life in New York. And that's the thing that I'm gambling with. I need to make sure that I'm working so hard that I can keep up. And I can sort of see how this is going to be a potential slippery slope in the future

when it gets bigger and bigger, when you start dealing with kids. And I'm gonna start thinking, oh, they need to go to the best school. And I need to have a house in this area where all the cool people are. And I can feel that sort of like treadmill feeling. Um, but I almost don't want to get off because I don't want to give myself permission to stop working really hard in a way.

I wouldn't look at it that way. I mean, you, you go to the playbook you played when I was your age, I, I didn't appreciate nor had access to nice things and nice restaurants. I just didn't. You know, you're at a point, Ed, where you shouldn't be saving 5%. You should be saving 10% and then the 5%, you know, 15%. Because if you just do the math, it's like what Brian Chesky from Airbnb says, you can have it all, you just can't have it all at once. And the reason why I have so much balance in my life and so much opulence was because I had a lack of it when I was your age.

And that is, I was very disciplined. I worked a lot, I didn't spend a lot of money, occasionally went out to dinner or whatever, went to Club Med in Mexico. That was my big vacation when I was your age. But you just gotta recognize that some of the, that indulgence now, and I'm not going to tell you not to do it. It's just a trade-off.

If you can find a way. I mean, my, my out of control opulence now is a function of the fact that didn't have it when I was young, I could have had more of it, but I wouldn't have been able to, you know, for the most part, I was constantly investing, reinvesting in startups, reinvesting in the stock market. And then sometimes I'd lose it all, which hurt, but I was always putting myself in a position that if the winds kicked up and my sales were up, I was going to make

a lot of money because I was constantly reinvesting in my own companies, constantly reinvesting in the own companies, constantly reinvesting in the markets, and not consuming a lot. I think it is very difficult when you're a guy your age, especially, I know you have a girlfriend, but you guys don't live together, right? No, we do. You do live together, Jesus Christ. Yeah.

Okay, so you're on your way. By the way, that's been a big, that's helpful in terms of just creating a more responsible lifestyle for sure. Huge. We always say greatness is in the agency of others. Wealth is in the agency of others. One, your ability to attract and retain really talented people, especially if you're an entrepreneur, or just find them. Go to a place where you're working with other talented people.

You want to be able to where you, if you look left and right and think these people are talented, you're going to make more money. That's sort of what I mean, right? Like I kind of, I feel like I need to spend to be, to be there, you know, I need to go out with my friends and go to these social events. Like one of, one of the questions I have on this list here of like situations, um, I'm not going to be specific about who this is, but you know, here's a situation. Your friend is getting married and has planned a very big bachelor party and you look at the agenda and you realize you're gonna have to spend a lot of money on flights, a lot of money on meals, on alcohol,

on going out, and it's all beginning to get pretty uncomfortable. But this is a really good friend and you don't wanna just not show up and let them down. So in a way it's sort of like, you need to, you need to be spending in order to maintain relationships at a certain point in life, I feel like. So I guess how do you think about that? If he's a really close friend, you should be able to say to him, boss,

this is a strain for us. I make really good money and it's a strain for me. I can't imagine what it's like for some of the other guys. And quite frankly, you're being a little bit selfish here. You're putting us in a difficult position because nobody wants to say, no, is there any way you can ratchet this back a bit? So I don't think that's unreasonable. You're at that age where you're just going to spend a disproportionate amount of money on the wedding industrial complex.

That's just going to happen. And it's going to be worse for your partner because she's going to have to buy bridesmaids dresses and way, way worse for women for sure. And then go to hotels that are overpriced because, you know, unless they bought out the hotel, but yeah, that's just part of that's just a tax that you paid at Williams Sonoma. I love that. That's right.

It's just part of it. Yeah. It's I guess it's just, I bring it up because I find it interesting how, as you age, it's like just the, the financial burdens just accumulate in ways that you didn't really expect, like the wedding tax that you just described is a very real tax and planning for those things. I I'd like to do it as best I can, but I think it is very difficult because is a very real tax and planning for those things. I'd like to do it as best I can, but I think it is very difficult

because costs just sort of come up out of nowhere. And the one I'm gonna bring up now, which is probably the biggest one, is children. Like children are a huge cost. So my question for you is, were you surprised by how much kids cost? And two, to what extent do you sort of budget in the cost of your children? Like how do you think of your kids as that line item on your income statement? Well, this is not financial advice, but my

experience with kids was that when I had them later in life, so I was a little bit more economically secure. You know, I had my son when I was 41, 42. And for me, it was actually, I think part of the reason I'm as wealthy as I am now is because I had kids. And the reason why is because I just scared the shit out of me and it got me very focused. I think having kids when you're younger, if you don't have dual income, would be really financially stressful. Also, something I did once I had kids was, and what I would recommend is ask yourself, can you make a lifestyle arbitrage? And this was my partner's idea. She said, let's move to Florida. We're going to be able to cut

our rent in half, if not by 60%. We're going to cut our private school tuition for our two boys by two thirds. Grace Church wanted $58,000 a year. And for me to bring that lady muffins. And then they ask you, are you philanthropic? Like, are you going to give us more money? Anyways, so we immediately cut our burn and that was her idea. She was smart, she's like, no, we're going to love Florida tonight.

Stop being such a snob. I'm like, I'm not going to Florida. They're all yeehaws down there driving F-150s and shooting at each other and their guns and everything. She's like, don't be an idiot. You love that stuff anyway. Yeah, all those better things life. But what I did do was smart.

I took all of the money that we saved and I put it into the market. So immediately, I think combined combined we were probably making, you know, I was probably making between, I don't know, 400,000 and 700,000 a year between the two of us. And then we took that 14% swing in savings and all the other savings. We took about 150, 200 grand a year and we put it into stocks for 10 years

from 2010 to 2020. Yeah. I mean, the thing that really shocks me is that, I mean, just how crazy it's gone 400 to $700,000 a year and you got priced out of New York. Like it's unbelievable. That's the part that I can't really wrap my head around in, especially living in New York and that's sort of what this, this treadmill feeling is. It's like in order to just get some basics done in New York, you need crazy amounts. There's a reason why people are moving into Texas. And there's a reason why the South

is economically booming. The people, a lifestyle arbitrage is, you should always be thinking about a lifestyle arbitrage, especially in a world of remote work. Where could I move? Don't be a snob. A lot of people are really happy in Atlanta. And economic security is an enormous ointment for stress and anxiety. And if you are blessed with mobility, you want to take advantage of it. I'm just going to start wrapping us up here. I know you've gotten a lot into philanthropy recently. Um, I know you've gotten a lot into philanthropy recently. We were talking about what is essential in life is philanthropy essential to you at this point? Is it something that you budget for and, you know, are you trying

to make more room for giving? You know, I've always said that my, my, one of my biggest unlocks is my atheism because it, I really think having a strong sense of the finite nature of life creates a lot of courage and a lot of boldness to share your emotions, to take risks, to tell people you care about them, to seize the moment, to embrace now. And one of the things I decided, when I sold my company

in 2017, I sold it for 160 million bucks. I was worth somewhere between 50 and 100 million, depending on how you would calculate my private investments. And I thought, all right, I'm going to put in $25 million. I'm going to go raise another 250 or 300, start a private equity fund, because I thought I need to be a billionaire by the time I'm 65. That was my goal. And I thought the only way I'm going to do that is through a private equity fund. I have the credibility, the contacts, I'm going to raise a fund. I got the first, I think I got about $50 million in commitments just from three calls. I was going to start a

consumer private equity fund right after I sold L2. And then I thought a friend of mine got sick, passed away, and I thought, okay, this is going really fast. I have enough money to live really well. I didn't have enough money for a plane,. I have enough money to live really well. I didn't have enough money for a plane, but I had enough money for everything else at that point. I thought, okay, why do I need to be a billionaire? I thought, well, all right, would I have more influence? Maybe, not much more.

Would I be able to do anything else? No, I can pretty much do anything I want right now. So I made a conscious decision that I would change my approach to money, and it was the following. Once I hit my number, which I was about to, anything above that, I would do one of two things. I would either spend it or I would give it away. I love spending money.

I'm selfish. I like nice things, nice experiences. But every year I look at my net worth and if it's up $7 million and I've spent four, I'll give three away. I do not need to increase my net worth. Hoarding is a disease that infects a lot of Americans. There's just no reason. I don't begrudge billionaires. I don't think they're as happy as me.

I don't think there's any reason to hoard money. Spend it. In a capitalist society, there's so many amazing things to spend it on. And then if you still have more money than what you need to spend to have an amazing capitalist society, there's so many amazing things to spend it on. And then if you still have more money than what you need to spend to have an amazing life, for God sakes, why wouldn't you find if you believe young men are struggling and it freaks

you out that four in five people in a morgue have died from suicide are men, why wouldn't you give money to an amazing charity with really talented people focusing on mental health? You know, the JED Foundation. Why wouldn't you, if you are constantly lecturing at people about the misgivings or the moral corruption of the university system and how we need more vocational training, well, if you have the money to start a vocational problem,

why the fuck wouldn't you? And you know what? It feels really good. It makes me feel strong. It makes me feel nice. I don't, it's not It feels really good. It makes me feel strong. It makes me feel nice. I don't, it's not even an ethical thing. It makes me feel like a baller. And also just some of it is an overdue nod

to California taxpayers. I give a lot of money back to UCLA and Berkeley because they spent so much money on me despite the fact I was such a fuck up. You know, California taxpayers kept giving me another chance. So this is a great position to be in. But once you hit your number, why on earth would you not do one of two things, spend it or give it away?

Well, this has been great. A final thought for me. So I, I feel like spending is kind of like the truest, most accurate reflection of ourselves. Like, you know, we tell ourselves these stories about, oh, this is who I am and this is what I like. And then we take these personality tests to sort of like figure out, oh, yeah, I'm kind of like a EQZ or whatever the fuck that test is. But it's like, if you just look at how you spend, it's like this data set testimony that says with no biases, like this is who you are, this is what you care about, this is what you want to achieve, and these are the people who you want to impress. Like I feel like if you want to understand who

you are, you just look at your bank statement. So we've been talking about your spending, we've been discussing it on this podcast. So I'm wondering what do you think your spending says about who you are as a person? I'm an atheist, I'm generous, and I'm a father. I recognize the finite nature of life. I'm spending a lot of money on experiences. I think I'm a generous person. I give away a lot of money.

I'm generous with my friends and I'm very focused on being a really generous provider for my kids and my partner. Those are the things I aspire to. It also says, quite frankly, I'm indulgent. I'm selfish. I spend a lot of money on my own comfort and my own joy and my own, you know, I do frivolous things that make me feel important and good. I spend money on things, you know, I spend money on dumb shit because I'm a bit of a narcissist. I mean, that's an interesting way to look at things.

So there's some very good things about my spending. There's some things I'm also probably not that proud of in terms of how I quit. I spent too much money on nightlife and alcohol. That's not good at my age. I have nice things quite frankly to probably impress other people that I shouldn't need to impress. How do you know I'm building a house in Aspen? I tell you. That's sort of fucking pathetic, isn't it?

So you're right, it does say a lot of things about me. It says a lot of good things, a lot of bad things. You know, I'm human. This episode was produced by Claire Miller and engineered by Benjamin Spencer. Our associate producer is Allison Weiss, Mia Silvario is our research lead, Jessica Lang is our research associate, Drew Burrows is our technical director, and Catherine Dillon is our executive producer. Thank you for listening to Proffigy Markets from the Vox Markets feed. What you're saying is you were irresponsible, but it was planned.

You made a conscious decision to be irresponsible. That's my room service. Speaking of irresponsible, I just ordered a shit ton of beef. It probably costs a little over a million. Talking about forced buyout. Yeah. Hold on. I'll be back in a second. You can leave it there because I'm on a podcast. You can leave it there because I'm going to, I'm on a podcast so you can leave it in there.

I'll bring it out. Thank you, sir. Thank you. So what you're saying is you made a responsible decision to be irresponsible. And I think that's okay. You know, occasionally it's fun to splurge and, you know, I would argue the splurges when you're young are, I think you remember them more. It is clearly bonus time.

You guys planned this. You guys so planned this. Scott, do you think it's important to be generous with your employees who don't have as much money as you? Where does that rank in your priorities? Scott, how do you think your employees get by and what could you do to make their lives easier? Yeah, yeah.

Something to think on. Oh, God. Support for this episode comes from AWS. AWS Generative AI gives you the tools to power your business forward with the security and speed of the world's most experienced cloud.