I made a lot of money in a short period of time because I was better at playing the bubble than most people. And I turned in nine months, I turned six grand into 400 grand. I was making way more money in the casino than I was at work.
I intentionally sandbagged two promotion opportunities because I had more fun trading stock. So, I called my boss, said I was going to quit, and she said, 'Did you take another job?' I said, 'No, I'm going to Barcelona for a week, and I bought a one-way ticket, and I don't know when I'm coming back to America.' I was discussing why NFTs were crazy overvalued and this whole thing was a bubble. My favorite stat in financial markets is Trump made more money on Trumpcoin than all crypto companies have made lifetime of net income. He was just like, 'You should totally just sell at least half of it and put in the S&P.' I said, 'Yeah, but I'm up 6,000% in nine months. And if I make another 150%, I could probably hit a million dollars before turning 24.'
You're like the middle of the road Andrew Tate. Like all of a sudden, you're inspiring these kids.
I'm Andrew Tate for upper middle class white men.
Hey everybody, welcome back to Reasonably Happy. My guest today is Jack Raines. Jack is a writer, investor at Slow Ventures, and creator of the popular Young Money newsletter that reaches over 60,000 ambitious young professionals. After starting out in corporate finance, Jack did what every responsible young professional does. He quit his job, bought a one-way ticket to Barcelona, and started writing. He wandered the world like a Jack Kerouac who traded meme stocks and was proficient at Excel. Jack tells the story and shares his life philosophy in his new book, Young Money: A Field Guide to Wealth and Purpose in Your 20s. In the book, Jack asks a deceptively simple question: What's the point of making money if you're wasting your life making it? He explores questions of status, opportunity cost, career ambition, and the one asset you can never earn back: time. Please welcome Jack Raines.
You're never going to be perfectly happy all the time. The best you can hope for is to be reasonably happy.
So, how long have you been back in New York now?
Uh, moved back in February, so I guess six months.
I mean, it's the best city in the world.
Wait, where you grew up in South Georgia?
Swimming pools and movie stars.
I think we have the most Waffle Houses per capita out of like any town in America. There's, I think there's five—Tifton has 20,000 people. There's five or six Waffle Houses. Um, so we have.
That's a great—that's a great data point.
Yeah. Between that and then every billboard is either a church advertisement, an adult superstore advertisement, a picture of zombie children burning in hell saying, 'Do you know Jesus?'
Or a political ad with an American flag.
I mean, it is the best place in the world to grow up.
Oh, yeah. Like runs right through the.
So, if you're driving from Atlanta to the beaches in Florida, you're being—trying to be converted or steered away from the fires of hell.
Yeah, correct. It's Zombie Children on Fire and it says, 'Do you know God?' It's like, 'Yeah, man. I did not want to go to church before this, but that—The Walking Dead got me.'
Yeah, man. How's the book going?
Uh, the book's going well. I mean, it's—it's good. It's good that it's actually done and it exists. It's—it's much easier to sell a book that exists than try to get people to pre-order a book that isn't out yet, I've realized. Um, people seem to love it, though. I have a bunch of angsty 24-year-old men who are DMing me saying, 'I really love your book.' You know, ideally you write a book to get a girlfriend. Instead, I'm getting this full like entourage.
And a bunch of bros, right?
You're the—like you're like the—the middle of the road Andrew Tate. Like all of a sudden, you're inspiring these kids.
Yeah. Yeah. I'm Andrew Tate for upper—upper middle class white men. It's—it's awesome.
You're—you're the Republican Jack Kerouac is kind of how I felt like.
Yeah. Bold of you to assume I'm Republican.
Well, I know that's—well, you are from Tifton and you played football. I—I don't mean—I don't mean to put you in a box. I apologize.
No, I voted Trump—Trump, Harris. One of my—one of my best friends was—he was engaged to a Venezuelan girl, and this—this is a great story, not at all related to the book, but you know, it was election season a couple years ago, and I said, 'Marcos, I'm a single-issue voter this year. I—I don't want you guys to get deported.' And I said, 'Is this like—are you going to get deported if Trump wins? 'Cause I'm probably going to vote for him unless your fiancée loses her visa.' And he said, 'Well, there's a very good chance that if Trump wins, asylum visas get pulled and we get deported.' And I was like, 'Okay, I'll vote for Harris.'
But it's going to be really problematic if you're still an American in six months. My family disowns me and they live in Guatemala City now. So anyway,
So where did the idea for the book come from?
It's funny. I've been writing a Substack for like—Substack newsletter for five years now. And initially it started.
Yep. Young Money. I decided to name the book the same thing as the newsletter to keep it really simple. It's just me and Lil Wayne.
Um, I had been writing a—basically I started writing a finance.
Most of my listeners have no idea who Lil Wayne is.
If you Google Young Money, it's this black guy with dreads and then it's me. So anyway, he's that guy. Um, anyway, I was 24. I'd quit my job and I knew I was moving to New York in a year for business school and.
Columbia, great business school. I—I also.
Did they give you a kaffiyeh when you matriculated to Columbia Business School?
You know, no, they actually didn't. But I did love checking out the undergrad campus while I was there. It was a ton of fun.
Um, but anyway, I—I wanted to get like a remote writing job from Morning Brew or one of these media startups. And I thought it would be a fun thing to do to kind of subsidize a year living abroad, hostel hopping when I was 24. Nobody would hire me for lack of journalism experience. And I thought that was dumb because I thought I knew more about financial markets than whoever was writing about the Morning Brew and the Hustle. So I just started writing my own newsletter and called it Young Money because I was 24 and I was largely writing about finance. And then I also was backpacking Europe by myself and just meeting all these random crazy people and thought it'd be fun to write a travel blog too. So I basically just had two concurrent newsletters: one where I was discussing why NFTs were crazy overvalued and this whole thing was a bubble, and then another thing where it was, hey, here's who I got drunk with in Krakow, Poland last week, and then we went to Auschwitz, and then I got deported from Norway. So it was two totally different trains. But I was just always writing about what was top of mind for me. And then after two years of that, in 2023, an editor at Penguin Random House reached out and she said, 'Hey, have you thought about writing a book?' I said, 'I've thought about it. I was kind of waiting for somebody like you to reach out and ask if I'd thought about writing a book.'
Yeah. When an editor call from—from Penguin calls, you should pick up—pick up.
Correct. And I've had some smaller publishing houses reach out, but I kind of—I didn't realize how much writing a book would suck. I knew that it would suck. So, I figured if I can get an advance to write it, at least that suck will be compensated on the front end.
Well, it's a forcing function, too.
You got somebody else going, 'We expect this book to be delivered.' When they give you a quarter of the advance up front, then you spend part of it that year and then you owe them the money back if you don't turn in the book, right? It's really a forcing function to write a book.
Yeah. So, let's go back in time. You graduate from college. What do you think you're going to do with your life?
Probably be an investment banker or management consultant. I played football at Mercer University. You're an Atlanta guy.
Macon, Georgia. Oh, yeah.
That's—that's Paris compared to Tifton.
And it is Tifton compared to New York.
Yes, it is. And it's probably Macon compared to Atlanta. Yeah. Um, it's—it's—it's directly like it is correctly categorized compared to Atlanta. Sure. Um, for those not listening, Macon is what, two hours south of Atlanta?
About an hour—hour and a half.
It's a smaller town. It's what, 100,000 people?
Probably 200,000. So decent-size small city.
Yeah. Mid-size city. It's where the Allman Brothers are from. Most—probably most important.
Okay. You know your fun facts.
Absolutely. Yeah. Yeah.
Uh, so not a big town. So you graduate from school. What—what do most of the kids end up doing?
Um, the motivated ones: real estate in Atlanta. And I did not—around my junior year of college, I kind of realized I wanted to end up in New York, California, DC, like bigger global cities doing stuff.
You're thinking—and—and I'm not trying to, uh, you know, disparage people from South Georgia, but most—most your peers aren't thinking at—that scale.
You're just not really aware of it. Like there's—it's not even a—I wouldn't even call it like a lack of ambition or desire. It's just your radar, right? And I thought spending some time in one of the bigger cities that wasn't the South would be interesting. And to me, having gone—I enjoy my time at Mercer, but Mercer is not a school that Goldman Sachs is recruiting from.
Yeah. It's not, believe it or not, Wharton, right?
So, I realized, okay, I should go to law school or business school. My dad, um, he went to undergrad at Davidson College and then he—great school—and then he went to law school at Georgia and then he practiced law for like seven years and hated it. I thought maybe law school would be the move. I was playing football in college and they only offer the LSAT on Saturdays. I almost on paper converted to Judaism to take the LSAT on a Sunday. One of my—one Jewish friend growing up, Alex, he told me that his rabbi would sign off on me being Jewish to get a religious exemption to take it on a Sunday. I just decided to take the GMAT instead and apply to business school. It's so funny. But I was almost on paper Jewish, which—I took the LSAT and the GMAT and I did very well on the GMAT and I flagged the LSAT. So I could have gone to Dartmouth for business school, which I did, or Georgia State for law school. And I'm like, I think I'll go the—the more prestigious route.
Yeah. And it's also more fun. It's like an easier.
It's a year. It's 50% short—or 33% shorter, right? And it's a lot of fun.
Yeah. When I was coming through undergrad, a lot of these business schools started offering deferred enrollment programs where they basically—you apply senior year of college, if you get in, um, you then work two to five years and then go to school versus working three years and then taking the GMAT. So got into Columbia, figured I would do corporate finance. Such a smart move. For me to—it's also just way easier to take a standardized test when you're 21 than when you're 25 or 26.
I had to go back and re-study algebra again.
Yeah, that sucks. Like I was still—I had taken college calculus a year or two before that, right? It was still top of mind, right?
Um, so I got into Columbia and I kind of figured, okay, I should decide if I want to be a banker or a consultant. Yeah. When I get to business school, that was kind of what I figured I would do. Um, that ended up not at all being what I did, but that was—that was the plan at 22.
And you ended up in a corporate finance job at, uh, the world's largest, uh, logistics company, UPS.
You bleed brown. Huge employer. Great company.
Great company. The worst thing about it though was I joined right when COVID hit.
So that's bad for a lot of just broader employment reasons. I think it's very good when you're 22 to have your starter job in an office where you meet your team.
And I—I was in the office for six days. UPS specifically, um, all new hires in the corporate office get to spend a day driving around in a UPS truck and they also get to work in a distribution center. So, you get to do a little bit of everything, which I think is a fun like culture company-building thing. Didn't get to do that with COVID, which is really—I was really looking forward to just speedrunning all the package routes. Um, yeah, the plan was I just applied to a lot of corporate finance-y, strategy-y jobs and I figured I would do one of those for two or three years, get promoted, go to Columbia, and then like gun for a banker seat basically.
So, COVID hits, I'm working remote. We were not set up for people to really work remote. I hadn't been fully onboarded. I was still getting like HR stuff and getting login to everything and I didn't have a remote token to log in. So, it was basically a month of doing fake work while they were just trying to figure out how do we get our new hires onboarded. I played a ton of Call of Duty Warzone and Fortnite with my college buddies who we were all in the same boat. Like,
You're just sitting in your apartment playing Call of Duty with your buddies.
I couldn't do anything else. There was—there was—I read through all the materials and it's like there's literally no work for me.
And you're getting a paycheck just to sit there in your underwear.
Okay, so great. And then like every other, um, understimulated 22-year-old male, I started speculating on the stock market.
So, this is 2021. Was it January, February 2020?
Early shutting down. You start shutting down. There's meme stocks popping.
So, I'm a very active member of Wall Street Bets with my burner Reddit account, Barlo Anthony, which is a play on words of Carmelo Anthony and Xanax Bar. It was my, uh, group chat name in college. And, um, anyway, I was like, 'This whole pandemic thing seems pretty bad. I should just put all my money in puts on the S&P and I bet it's going to tank.' And I turned 10 grand into 30 grand. I felt like Michael Burry. And then I doubled down shorting the market again. And it turned around and ripped in my face because it turns out, you know, when the entire economy is tech companies and we go remote, tech companies actually make more money and quantitative easing is a real thing. Market went up. I then went.
So you got crushed on that.
10 to 30 back to 10 and I was sick to my stomach and said, I'm never going to buy—I'm just going to buy index funds. I'm never gambling on the market again. And then my best friend Jake texted me a month later and said, 'Do you know what a SPAC is?' I said, 'No.' And he said, 'I don't either, but if you buy this one, it turns into DraftKings stock in a month.' And I said, 'Well, that doesn't make sense.' And I looked it up and he gave a really dumb explanation that was directionally correct.
A SPAC is just like a shell company. What's it stand for? Special—
Special purpose acquisition company. So, typically the company goes public through an IPO. Um, you're an ex-Facebook guy. Y'all are private. You go public, sell shares on the public markets, and now it's a public company. A SPAC is basically just a bank account. It's—it's—it's effectively just a public.
You put a private company inside a SPAC. That looked dirty, but I didn't mean to do that.
That's fine. It did a little bit. Yeah.
Um, yeah, basically they raise a lot of money from investors. They find a private company. They give that company that money for a percentage of the company, and then the ticker changes, and it's publicly traded. And SPACs, hilariously, were a bubble during the pandemic. There were the crypto bubbles, the meme stock bubbles. SPACs were like a more niche bubble. And I won't bore everybody with the details, but basically I made a lot of money in a short period of time because I was better at playing the bubble than most people. And I turned—in nine months, I turned six grand into 400 grand. I was 23.
In nine months, you were 23, right?
And I again, I was just not working. Like I was pretending to work basically. Even once I got logged in at this point, I was making way more money in the casino than I was at work. I intentionally sandbagged two promotion opportunities because I had more fun trading stocks than I did. I was like, the 15k pay that prevents the 50 to 100k stock trade is just not worth it.
Okay, let's be clear. We're not offering financial advice on this program. So, nothing said in this episode should be taken as financial advice.
But if you're going to speculate on stocks, do it in your retirement account. Why? One, no capital gains. Two, you can only contribute $7,000 into a Roth. So, if it's your first year, you can only lose 7 thou. Like, that's the most you can lose. You actually can't put more money into it. Again, I wouldn't do that, but if you're going to do that, it's actually tax efficient, but don't do it.
But don't do it. We're going to talk about more—more about speculation by Gen Z in a few minutes.
So, I end up making 400 grand and then—or 393 grand profit. And I remember calling my dad and it was February 2021 at this point, so nine months later. And he was just like, 'You should totally just sell at least half of it and put it in the S&P.' And I said, 'Yeah, but I'm up 6,000% in nine months. And if I make another 150%, I could probably hit a million dollars before turning 24 from a $6,000 base.' That's.
So you're tweaking on invest—or on gambler's dopamine or whatever it is.
And the issue was I was actually good. It was a very niche thing I was good at, but I—I had an edge. The issue was anytime there's an edge in—in a particular market segment, it just—it'll last for a few months, maybe a year, and then it goes away because everybody else figures out what's going on. They all move their money in. A bunch of people started launching SPACs and then there just wasn't enough money to go around and it just stopped.
Have you read Spencer Jakab's book about the GameStop, uh, bubble?
I do love Spencer Jakab's stuff. I haven't read his book.
He's, uh—he was a guest on the show a couple years ago. Book's great. Yeah, it's just mind-blowing the confluence of events that happened. You had Robinhood launched. Yeah. Pandemic checks went out and you have all these guys your age that are sitting at home with nothing to do. Yeah. And they're like, I guess I'll go online and, you know, see what's happening in the market today. And then boom. I—I remember seeing—driving down Peachtree Street and seeing somebody in one of these apartment buildings on like the ninth floor with a—like a bed sheet spray painted with 'To the Moon' on it.
Yep.
It's—and it's—it's crazy. I mean, I was like pretty involved in some of these random chat rooms. There were Discord chats where people were pumping penny—it was literally securities fraud. Like a lot.
Diamond hands, baby. Diamond.
There were people who went to court. There was this whole group called Atlas Trading where there was a guy like Zack Morris from Saved by the Bell. There was a Twitter account called Mr. Zack Morris who was just pumping penny stock biotech companies. He personally made $10 million and he was—he had a paid group chat where he would tell them what he would buy and then to the free group chat he would send what he was buying an hour later. So he was just.
Hey, the president's doing that now, right?
Well, it's legal now. Like—like it's totally fine if it's your own cryptocurrency. My favorite stat in financial markets is Trump made more money on Trumpcoin than all crypto companies have made lifetime in net income. It's like—it's just so good.
Okay, we're not here to talk about meme stocks. So you made a ton. We're—we're here to talk about your life journey in the—in the book. Okay. So, you make a ton of money and then.
And then I stopped making money trading SPACs. I'm addicted to trading at this point. And I was like, you know what? I made money trading this thing. I can probably just trade other stocks and keep making money. Which act—that's like saying, 'Oh, I was really good at football in college. Let me now go play volleyball.' And it doesn't actually work like that.
Oh, that applies to all aspects of life, right? Like going from working at Facebook to comedy, for example. Surely I'll be just as successful in the creative world as I was in the technology world.
Facebook's sort of creative.
So I end up losing about $150,000 in a day on a bad trade. My earnings miss. Well, considering that was two and a half times my salary. I just felt like an idiot. Like there was this whole—did you learn anything? Whatever. I didn't really learn anything I didn't already know. Like I actually should have—when the thing I was doing wasn't working, I should have looked at it like, 'Okay, I just made a lot more money than I should have by exploiting this one thing. Let's throw it in an index fund.' And then now you have like a $400,000 retirement account.
Great head start. Great head start.
The smart thing I did do was once that blew up and I cut that money more than in half, I was like, 'All right, well, that was dumb. I could try to trade it back and make it all back, but that's gonna be really annoying if I lose the rest of it, or just cash some of it out for some like fun fuck-around money and then leave the rest in the retirement account.' So, that's actually what I did. And my—my next thought was, okay, well, I'm going to go—this was now August 2021. I am going to go to business school in a year. What do I want to do for the next year? I'm obviously checked out of my corporate finance job. Um, is there anything that's just more interesting to do over the next year pre-business school that I probably won't be able to do after? And the two things that I thought were pretty cool were—I always liked writing. I was writing like freelance stock—freelance stock articles about the stocks I was looking at. And then I'd always wanted to do the like classic gap year backpack Europe type of trip. And I'd studied abroad one summer in college, but I never did the whole let's just go on an adventure and see what happens with no real goal. And that was a thing that I really wanted to do. It didn't make financial sense, but from a just pure fun perspective, it made life sense. And I had like more money. I was already budgeting money from my job to like put toward a two or three month trip. I now had call it 150 grand that I wasn't really expecting to have. And to me, the right math was take—leave most of that in like a retirement account, but take part of it and go have fun with it because I was only going to be 24 once. So, I called my boss, said I was going to quit, and she said, 'Did you take another job?' I said, 'No, I'm going to Barcelona for a week, and I bought a one-way ticket, and I don't know when I'm coming back to America.' Yeah.
And she thought I'd just been slacking at work the whole time. When I told her, 'Hey, you probably thought I was lazy. I was actually just addicted to trading stocks,' she felt a lot better because she was worried about my career development, but then realized I'm not a loser. I just wasn't really caring about work.
Yeah. Tell me about your grandmother, the trip you took with her.
Yep. So, my paternal grandmother, Mama Ruth, um, when I was 11, she told me that I was—I'm the oldest grandchild. And she said she wanted to take me on a trip anywhere in the world. And she proceeded to tell my sister and all my cousins this as well. And I said, 'Okay, like anywhere.' And she said, 'Yeah.' And I didn't believe anywhere. I meant literally anywhere. So, at first I pitched like Jamaica or Costa Rica or somewhere pretty close.
