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‘Young Money’ with Jack Raines · Reasonably Happy with Paul Ollinger

0:00
SPEAKER_00: Hey everybody, welcome back to Reasonably Happy.
0:02
SPEAKER_00: My guest today is Jack Raines.
0:05
SPEAKER_00: Jack is a writer,
0:06
SPEAKER_00: investor at Slow Ventures,
0:08
SPEAKER_00: and creator of the popular Young Money newsletter that reaches
0:12
SPEAKER_00: over 60,000 ambitious young professionals.
0:15
SPEAKER_00: After starting out in corporate finance,
0:17
SPEAKER_00: Jack did what every responsible young professional does.
0:21
SPEAKER_00: He quit his job, bought a one-way ticket to Barthelona, and started writing.
0:26
SPEAKER_00: He wandered the world like a Jack Kerouac who traded meme stocks and was proficient at Excel.
0:30
SPEAKER_00: Jack tells the story and shares his life philosophy in his new book,
0:34
SPEAKER_00: Young Money, A Field Guide to Wealth and Purpose in Your 20s.
0:38
SPEAKER_00: In the book, Jack asks a deceptively simple question.
0:42
SPEAKER_00: What's the point of making money if you're wasting your life making it?
0:46
SPEAKER_00: He explores questions of status,
0:48
SPEAKER_00: opportunity cost, career ambition, and the one asset you can never earn back, time.
0:54
SPEAKER_00: Please welcome Jack Raines.
0:57
SPEAKER_00: You're never going to be perfectly happy all the time.
1:00
SPEAKER_00: The best you can hope for is to be Reasonably Happy.
1:04
SPEAKER_01: Reasonably Happy.
1:08
SPEAKER_00: So how long have you been back in New York now?
1:10
SPEAKER_01: I moved back in February.
1:12
SPEAKER_01: So I guess six months.
1:13
SPEAKER_00: Yeah.
1:14
SPEAKER_01: Good to be back.
1:15
SPEAKER_00: Yeah.
1:15
SPEAKER_00: How's it going?
1:16
SPEAKER_01: I mean, it's the best city in the world.
1:18
SPEAKER_01: You think so?
1:19
SPEAKER_01: I certainly do.
1:20
SPEAKER_00: Wait, you grew up in South Georgia?
1:22
SPEAKER_00: Tifton.
1:23
SPEAKER_00: Tifton.
1:23
SPEAKER_00: Yeah, are you familiar?
1:25
SPEAKER_00: Swimming pools and movie stars.
1:27
SPEAKER_01: I think we have the most waffle houses per capita out of any town in America.
1:33
SPEAKER_01: I think there's five waffle houses.
1:34
SPEAKER_01: Tifton has 20,000 people.
1:35
SPEAKER_01: There's five or six waffle houses.
1:39
SPEAKER_00: That's a great data point.
1:40
SPEAKER_01: Yeah, between that and then every billboard is either a church advertisement or
1:45
SPEAKER_01: An adult superstore advertisement,
1:47
SPEAKER_01: a picture of zombie children burning in hell saying, do you know Jesus?
1:51
SPEAKER_01: Or a political ad with an American flag.
1:53
SPEAKER_01: I mean, it is the best place in the world to grow up.
1:56
SPEAKER_00: Is that off 75?
1:57
SPEAKER_01: Oh yeah, like runs right through the center.
1:59
SPEAKER_00: So if you're driving from Atlanta to the beaches in Florida,
2:02
SPEAKER_00: you're being, trying to be converted or steered away from the fires of hell.
2:07
SPEAKER_00: Correct.
2:08
SPEAKER_00: By billboards.
2:10
SPEAKER_01: Yeah, correct.
2:10
SPEAKER_01: It's zombie children on fire and it says, do you know God?
2:14
SPEAKER_01: It's like, yeah,
2:15
SPEAKER_01: man, I did not want to go to church before this, but that, The Walking Dead got me.
2:20
SPEAKER_00: Yeah, man.
2:21
SPEAKER_00: How's the book going?
2:22
SPEAKER_01: The book's going well.
2:23
SPEAKER_01: I mean, it's good that it's actually done and it exists.
2:27
SPEAKER_01: It's much easier to sell a book that exists than try to get people to preorder
2:31
SPEAKER_01: a book that isn't out yet, I've realized.
2:34
SPEAKER_01: People seem to love it, though.
2:36
SPEAKER_01: I have a bunch of angsty 24-year-old men who are DMing me saying, I really love your book.
2:42
SPEAKER_01: Ideally, you write a book to get a girlfriend.
2:44
SPEAKER_01: Instead, I'm getting this full entourage of dudes.
2:46
SPEAKER_01: Get a bunch of bros.
2:48
SPEAKER_00: Right.
2:48
SPEAKER_00: You're like the middle-of-the-road Andrew Tate.
2:51
SPEAKER_00: Yeah.
2:54
SPEAKER_01: I'm Andrew Tate for Upper Middle Class White Men.
2:56
SPEAKER_01: It's awesome.
2:57
SPEAKER_00: You're the Republican Jack Kerouac.
2:59
SPEAKER_00: That's kind of how I felt.
3:01
SPEAKER_01: Bold are you to assume I'm Republican.
3:03
SPEAKER_00: Well, I know.
3:04
SPEAKER_00: Well, you are from Tifton.
3:05
SPEAKER_00: You played football.
3:05
SPEAKER_00: I don't mean to put you in a box.
3:07
SPEAKER_00: I apologize.
3:08
SPEAKER_00: No, no, no.
3:09
SPEAKER_01: I voted Trump, Trump, Harris.
3:11
SPEAKER_01: Did you really?
3:12
SPEAKER_01: Yeah.
3:12
SPEAKER_01: One of my best friends, he was engaged to a Venezuelan girl.
3:16
SPEAKER_01: And this is a great story.
3:17
SPEAKER_01: It's not at all related to the book.
3:19
SPEAKER_01: But, you know, it was election season a couple of years ago.
3:22
SPEAKER_01: And I said, Marcos, I'm a single-issue voter this year.
3:25
SPEAKER_01: I don't want you guys to get deported.
3:27
SPEAKER_01: And I said...
3:29
SPEAKER_01: Are you going to get deported if Trump wins?
3:31
SPEAKER_01: Because I'm probably going to vote for him unless your fiancé loses her visa.
3:37
SPEAKER_01: And he said, well,
3:39
SPEAKER_01: there's a very good chance that if Trump wins,
3:42
SPEAKER_01: asylum visas get pulled and we get deported.
3:45
SPEAKER_01: And I was like, okay, I'll vote for Harris.
3:47
SPEAKER_00: There you go.
3:48
SPEAKER_01: But it's going to be really problematic if you're still an American six months.
3:51
SPEAKER_01: My family disowns me.
3:52
SPEAKER_01: They live in Guatemala City now.
3:54
SPEAKER_01: So anyway.
3:55
SPEAKER_00: So where did the idea for the book come from?
3:57
SPEAKER_01: It's funny, I've been writing a Substack newsletter for five years now.
4:02
SPEAKER_01: And initially it started... That's Young Money?
4:04
SPEAKER_01: Yep, Young Money.
4:05
SPEAKER_01: I decided to name the book the same thing as the newsletter to keep it really simple.
4:08
SPEAKER_01: It's just me and Lil Wayne.
4:10
SPEAKER_01: I had been writing a... Basically I started writing a finance...
4:13
SPEAKER_00: Most of my listeners have no idea who Lil Wayne is.
4:16
SPEAKER_01: If you Google Young Money, it's this black guy with dreads and then it's me.
4:19
SPEAKER_01: So anyway, he's that guy.
4:21
SPEAKER_01: Yeah.
4:23
SPEAKER_01: Anyway, I was 24,
4:24
SPEAKER_01: I'd quit my job, and I knew I was moving to New York in a year for business school.
4:29
SPEAKER_00: Columbia.
4:30
SPEAKER_01: Right, Columbia, great business school.
4:32
SPEAKER_00: Did they give you a keffiyeh when you matriculated to Columbia Business School?
4:36
SPEAKER_01: No, they actually didn't, but I did.
4:38
SPEAKER_01: Love checking out the undergrad campus while I was there.
4:40
SPEAKER_01: It was a ton of fun.
4:42
SPEAKER_01: But anyway,
4:43
SPEAKER_01: I wanted to get like a remote writing job for Morning Brew or one
4:46
SPEAKER_01: of these media startups.
4:48
SPEAKER_01: And I thought it would be a fun thing to do to kind of subsidize
4:51
SPEAKER_01: a year living abroad, hostel hopping when I was 24.
4:54
SPEAKER_01: Nobody would hire me for lack of journalism experience.
4:56
SPEAKER_01: And I thought that was dumb because I thought I knew more about financial markets
4:59
SPEAKER_01: than whoever was writing about the Morning Brew and the hustle.
5:03
SPEAKER_01: So I just started writing my own newsletter and called it Young Money
5:06
SPEAKER_01: because I was 24 and I was largely writing about finance.
5:10
SPEAKER_01: And then I also was backpacking Europe by myself
5:15
SPEAKER_01: and just meeting all these random crazy people and thought it'd be fun to write
5:18
SPEAKER_01: a travel blog too.
5:19
SPEAKER_01: So I basically just had two concurrent newsletters.
5:21
SPEAKER_01: One where I was discussing why NFTs were crazy overvalued and this whole thing was a bubble.
5:27
SPEAKER_01: And then another thing where it was,
5:28
SPEAKER_01: hey, here's who I got drunk with in Krakow, Poland last week.
5:31
SPEAKER_01: And then we went to...
5:34
SPEAKER_01: And then I got deported from Norway.
5:36
SPEAKER_01: So it was two totally different trains,
5:39
SPEAKER_01: but I was just always writing about what was top of mind for me.
5:42
SPEAKER_01: And then after two years of that,
5:45
SPEAKER_01: in 2023,
5:46
SPEAKER_01: an editor at Penguin Random House reached out and she said,
5:48
SPEAKER_01: hey, have you thought about writing a book?
5:50
SPEAKER_01: I said, I've thought about it.
5:51
SPEAKER_01: I was kind of waiting for somebody like you to reach out and ask if I'd thought
5:54
SPEAKER_01: about writing a book.
5:55
SPEAKER_01: Yeah.
5:56
SPEAKER_00: When an editor from Penguin calls, you should pick up the phone.
6:00
SPEAKER_01: And I'd had some smaller publishing houses reach out.
6:03
SPEAKER_01: But I didn't realize how much writing a book would suck.
6:06
SPEAKER_01: I knew that it would suck,
6:08
SPEAKER_01: so I figured if I can get an advance to write it,
6:11
SPEAKER_01: at least that suck will be compensated on the front end.
6:13
SPEAKER_00: Well, it's a forcing function, too.
6:15
SPEAKER_00: Correct.
6:16
SPEAKER_00: You've got somebody else going, we expect this book to be delivered.
6:19
SPEAKER_01: When they give you a quarter of the advance up front,
6:21
SPEAKER_01: and then you spend part of it that year,
6:23
SPEAKER_01: and then you owe them the money back if you don't turn in the book,
6:26
SPEAKER_01: it's really a forcing function to write a book.
6:28
SPEAKER_00: Yeah.
6:29
SPEAKER_00: So let's go back in time.
6:30
SPEAKER_00: You graduated from college.
6:31
SPEAKER_00: What do you think you're going to do with your life?
6:33
SPEAKER_01: Probably be an investment banker or management consultant.
6:37
SPEAKER_01: I played football at Mercer University.
6:38
SPEAKER_01: You're an Atlanta guy.
6:39
SPEAKER_01: Macon, Georgia.
6:40
SPEAKER_00: Oh, yeah.
6:41
SPEAKER_00: That's Paris compared to Tifton.
6:43
SPEAKER_01: Correct.
6:44
SPEAKER_01: And it is Tifton compared to New York.
6:46
SPEAKER_01: Yes, it is.
6:48
SPEAKER_01: And it's probably Macon compared to Atlanta.
6:50
SPEAKER_01: Yeah.
6:51
SPEAKER_01: It's directly, like, it is correctly categorized compared to Atlanta.
6:55
SPEAKER_01: Sure.
6:56
SPEAKER_00: For those not listening, Macon is, what, two hours south of Atlanta?
6:59
SPEAKER_01: About an hour.
6:59
SPEAKER_01: Yeah.
7:00
SPEAKER_01: Hour, hour and a half.
7:00
SPEAKER_00: It's a smaller town.
7:01
SPEAKER_00: It's, what, 100,000 people?
7:02
SPEAKER_00: Probably 200,000.
7:03
SPEAKER_01: Okay.
7:04
SPEAKER_01: So decent-sized, small city, big town.
7:06
SPEAKER_01: Yeah, mid-sized city.
7:07
SPEAKER_00: It's where the Allman Brothers are from.
7:08
SPEAKER_00: Correct.
7:09
SPEAKER_00: Probably most important.
7:10
SPEAKER_01: Okay, you know your fun facts.
7:11
SPEAKER_00: Absolutely, yeah.
7:12
SPEAKER_01: Yep.
7:13
SPEAKER_00: So not a big town.
7:15
SPEAKER_00: So you graduate from school.
7:16
SPEAKER_00: What do most of the kids end up doing?
7:18
SPEAKER_00: The motivated ones.
7:19
SPEAKER_01: Real estate in Atlanta.
7:21
SPEAKER_01: And I did not,
7:23
SPEAKER_01: around my junior year of college,
7:25
SPEAKER_01: I kind of realized I wanted to end up in the New York,
7:28
SPEAKER_01: California, D.C., like bigger global cities doing stuff.
7:31
SPEAKER_00: You're thinking,
7:33
SPEAKER_00: and I'm not trying to,
7:36
SPEAKER_00: you know,
7:36
SPEAKER_00: disparage people from South Georgia,
7:38
SPEAKER_00: but most of your peers aren't thinking at that scale.
7:42
SPEAKER_01: You're just not really aware of it.
7:44
SPEAKER_01: I wouldn't even call it a lack of ambition or desire.
7:47
SPEAKER_01: It's not on the radar.
7:49
SPEAKER_00: Right.
7:50
SPEAKER_01: And I thought spending some time in one of the bigger cities that wasn't
7:55
SPEAKER_01: the South would be interesting.
7:56
SPEAKER_01: And to me,
7:57
SPEAKER_01: I enjoyed my time at Mercer,
7:59
SPEAKER_01: but Mercer's not a school that Goldman Sachs is recruiting from.
8:03
SPEAKER_00: Yeah, it's not Wharton.
8:05
SPEAKER_01: Right.
8:05
SPEAKER_01: So I realized, okay, I should go to law school or business school.
8:08
SPEAKER_01: My dad...
8:10
SPEAKER_01: He went to undergrad at Davidson College and then he went to law school at Georgia
8:15
SPEAKER_01: and then he practiced law for like seven years and hated it.
8:18
SPEAKER_01: I thought maybe law school would be the move.
8:20
SPEAKER_01: I was playing football in college and they only offer the LSAT on Saturdays.
8:24
SPEAKER_01: I almost on paper converted to Judaism to take the LSAT on a Sunday.
8:29
SPEAKER_01: My one Jewish friend growing up, Alex,
8:31
SPEAKER_01: he told me that his rabbi would sign off of me being Jewish to get
8:34
SPEAKER_01: a religious exemption and take it on a Sunday.
8:36
SPEAKER_01: I just decided to take the GMAT instead and apply to business school.
8:39
SPEAKER_01: That's so funny.
8:40
SPEAKER_01: But I was almost on paper Jewish.
8:42
SPEAKER_00: I took the LSAT and the GMAT and I did very well on the GMAT and I flagged the LSAT.
8:47
SPEAKER_00: So I could have gone to Dartmouth for business school,
8:50
SPEAKER_00: which I did, or Georgia State for law school.
8:52
SPEAKER_00: And I'm like, I think I'll go the more prestigious route.
8:55
SPEAKER_01: Yeah, and it's also more fun.
8:57
SPEAKER_01: It's like an easier- It's 50% short, or 33% shorter.
8:58
SPEAKER_00: Right.
8:59
SPEAKER_00: And it's a lot of fun.
9:00
SPEAKER_00: Yeah.
9:03
SPEAKER_01: When I was coming through undergrad,
9:04
SPEAKER_01: a lot of these business schools started offering deferred enrollment programs
9:07
SPEAKER_01: where they basically you apply senior year of college.
9:10
SPEAKER_01: If you get in,
9:12
SPEAKER_01: you then work two to five years and then go to school versus working three years and
9:15
SPEAKER_01: then taking the GMAT.
9:17
SPEAKER_01: So got into Columbia.
9:18
SPEAKER_01: Figured I would do corporate finance.
9:20
SPEAKER_01: That's such a smart move of you to do that.
9:21
SPEAKER_01: It's also just way easier to take a standardized test when you're 21 than when you're 25 or 26.
9:25
SPEAKER_00: I had to go back and study algebra again.
9:29
SPEAKER_01: Yeah, that sucks.
9:30
SPEAKER_01: I had taken college calculus a year or two before that.
9:33
SPEAKER_01: It was still top of mind.
9:35
SPEAKER_01: So I got into Columbia and I kind of figured, okay,
9:38
SPEAKER_01: I should decide if I want to be a banker or a consultant when I get
9:41
SPEAKER_01: to business school.
9:42
SPEAKER_01: That was kind of what I figured I would do.
9:45
SPEAKER_01: That ended up not at all being what I did, but that was the plan at 22.
9:49
SPEAKER_00: And you ended up in a corporate finance job at the world's largest logistics company.
9:54
SPEAKER_00: UPS.
9:55
SPEAKER_00: UPS.
9:55
SPEAKER_01: I bled brown.
9:56
SPEAKER_01: You bled brown.
9:57
SPEAKER_00: Huge employer, great company.
9:59
SPEAKER_01: Great company.
9:59
SPEAKER_01: The worst thing about it, though, was I joined right when COVID hit.
10:03
SPEAKER_00: Oh, wow.
10:04
SPEAKER_01: A lot of just broader employment reasons.
10:06
SPEAKER_01: I think it's very good when you're 22 to have your starter job in an office
10:10
SPEAKER_01: where you meet your team.
10:11
SPEAKER_01: 100%.
10:11
SPEAKER_01: And I was in the office for six days.
10:14
SPEAKER_01: UPS specifically,
10:16
SPEAKER_01: all new hires in the corporate office get to spend a day driving around in
10:20
SPEAKER_01: a UPS truck.
10:21
SPEAKER_01: How fun.
10:21
SPEAKER_01: And they also get to work in a distribution center.
10:23
SPEAKER_01: So you get to do a little bit of everything, which I think is a fun, like, So what happened?
10:26
SPEAKER_01: So COVID hits.
10:27
SPEAKER_01: I'm working remote.
10:51
SPEAKER_01: We were not set up for people to really work remote.
10:53
SPEAKER_01: I hadn't been fully onboarded.
10:55
SPEAKER_01: I was still getting HR stuff and getting logins to everything,
10:59
SPEAKER_01: and I didn't have a remote token to logins.
11:01
SPEAKER_01: It was basically a month of doing fake work while they were just trying
11:04
SPEAKER_01: to figure out how do we get our new hires onboarded.
11:06
SPEAKER_01: I played a ton of Call of Duty Warzone and Fortnite with my college buddies.
11:10
SPEAKER_01: We were all in the same boat.
11:11
SPEAKER_00: You're just sitting in your apartment playing Call of Duty with your buddies.
11:14
SPEAKER_01: I couldn't do anything else.
11:15
SPEAKER_01: There was...
11:16
SPEAKER_01: I read through all the materials and it's like there's literally no work for me to do.
11:19
SPEAKER_00: And you're getting a paycheck just to sit there in your underwear.
11:22
SPEAKER_01: Okay, so great.
11:23
SPEAKER_01: And then like every other under-stimulated 22-year-old male,
11:27
SPEAKER_01: I started speculating on the stock market.
11:29
SPEAKER_00: So this is 2021?
11:30
SPEAKER_01: This was January, February 2020.
11:33
SPEAKER_00: Okay, right.
11:34
SPEAKER_00: Yeah.
11:35
SPEAKER_00: World's shutting down.
11:36
SPEAKER_00: World's shutting down.
11:37
SPEAKER_00: There's meme stocks popping.
11:39
SPEAKER_01: So I'm a very active member of Wall Street Bets with my burner Reddit account,
11:44
SPEAKER_01: Barmello's Anthony, which is a play on words of Carmelo Anthony and Xanax Bar.
11:48
SPEAKER_01: It was my group chat name in college.
11:51
SPEAKER_01: And anyway...
11:53
SPEAKER_01: I was like, this whole pandemic thing seems pretty bad.
11:57
SPEAKER_01: I should just put all my money and puts on the S&P and I bet it's going to tank.
12:01
SPEAKER_01: And I turned 10 grand into 30 grand.
12:03
SPEAKER_01: I felt like Michael Burry.
12:04
SPEAKER_01: And then I doubled down, shorting the market again.
12:06
SPEAKER_01: And it turned around and ripped in my face because it turns out,
12:09
SPEAKER_01: you know,
12:10
SPEAKER_01: when the entire economy is tech companies and we go remote,
12:13
SPEAKER_01: tech companies actually make more money.
12:15
SPEAKER_01: And quantitative easing is a real thing.
12:18
SPEAKER_01: Market went up.
12:19
SPEAKER_01: So you got crushed on that.
12:20
SPEAKER_01: 10 to 30 back to 10.
12:22
SPEAKER_00: And I was sick to my stomach and said, I'm just going to buy index funds.
12:25
SPEAKER_00: I'm never gambling on the market again.
12:27
SPEAKER_01: And then my best friend, Jake, texted me a month later and said, do you know what a SPAC is?
12:32
SPEAKER_01: I said, no.
12:33
SPEAKER_01: And he said, I don't either, but if you buy this one, it turns into DraftKings stock in a month.
12:38
SPEAKER_01: And I said, well, that doesn't make sense.
12:40
SPEAKER_01: And I looked it up, and he gave a really dumb explanation that was directionally correct.
12:45
SPEAKER_01: A SPAC is just like a shell company.
12:47
SPEAKER_00: What's it saying for?
12:48
SPEAKER_00: Special?
12:48
SPEAKER_01: Special Purpose Acquisition Company.
12:50
SPEAKER_01: So typically, the company goes public through an IPO.
12:53
SPEAKER_01: You're an ex-Facebook guy.
12:55
SPEAKER_01: Y'all are private,
12:56
SPEAKER_01: you go public, sell shares in the public markets, and now it's a public company.
13:00
SPEAKER_01: A SPAC is basically just a bank account.
13:03
SPEAKER_00: You put a private company inside a SPAC.
13:06
SPEAKER_00: That looked dirty, but I didn't mean to do that.
13:08
SPEAKER_00: That's fine.
13:09
SPEAKER_01: It did a little bit.
13:09
SPEAKER_00: Yeah.
13:10
SPEAKER_01: But yeah, basically they raise a lot of money from investors.
13:12
SPEAKER_01: They find a private company.
13:14
SPEAKER_01: They give that company that money for a percentage of the company.
13:16
SPEAKER_01: And then the ticker changes and it's publicly traded.
13:20
SPEAKER_01: And SPACs hilariously were a bubble during the pandemic.
13:23
SPEAKER_01: There were the crypto bubbles, the meme stock bubbles.
13:25
SPEAKER_01: SPACs were like a more niche bubble.
13:28
SPEAKER_01: And I won't bore everybody with the details,
13:30
SPEAKER_01: but basically I made a lot of money in a short period of time because I was better
13:35
SPEAKER_01: at playing the bubble than most people.
13:37
SPEAKER_01: And I turned, in nine months, I turned $6,000 and $400,000.
13:41
SPEAKER_01: I was 23.
13:42
SPEAKER_00: In nine months, you were 23.
13:43
SPEAKER_01: Right.
13:43
SPEAKER_01: And again, I was just not...
13:46
SPEAKER_01: I was pretending to work, basically.
13:48
SPEAKER_01: Even once I got logged in at this point,
13:49
SPEAKER_01: I was making way more money in the casino than I was at work.
13:53
SPEAKER_01: I intentionally sandbagged two promotion opportunities
13:56
SPEAKER_01: because I had more fun trading stocks than I did.
13:59
SPEAKER_01: I was like, the $15K paybop that prevents the $50K to $100K stock trade is just not worth it.
14:05
SPEAKER_00: Okay, let's be clear.
14:06
SPEAKER_00: We're not offering financial advice on this program.
14:09
SPEAKER_00: So nothing said in this episode should be taken as financial advice.
14:12
SPEAKER_01: But if you're going to speculate on stocks, do it in your retirement account.
14:16
SPEAKER_01: Why?
14:17
SPEAKER_01: One, no capital gains.
14:19
SPEAKER_01: Two, you can only contribute $7,000 into a Roth.
14:22
SPEAKER_01: So if it's your first year, you can only lose $7,000.
14:25
SPEAKER_01: That's the most you can lose.
14:26
SPEAKER_01: You actually can't put more money into it.
14:28
SPEAKER_01: Again, I wouldn't do that.
14:30
SPEAKER_01: But if you're going to do that, it's actually...
14:32
SPEAKER_01: Tax efficient.
14:33
SPEAKER_00: But don't do it.
14:34
SPEAKER_00: But don't do it.
14:34
SPEAKER_00: We're going to talk more about speculation by Gen Z in a few minutes.
14:39
SPEAKER_01: So I ended up making $393,000 profit.
14:44
SPEAKER_01: And I remember calling my dad.
14:46
SPEAKER_01: And it was February 2021 at this point, so nine months later.
14:49
SPEAKER_01: And he was just like, you should totally just sell at least half of it and put it in the S&P.
14:54
SPEAKER_01: And I said, yeah, but I'm up 6,000% in nine months.
14:57
SPEAKER_01: And if I make another 150%, I could probably hit $1 million before turning 24.
15:02
SPEAKER_01: From a $6,000 base, that's pretty cool.
15:04
SPEAKER_00: So you're tweaking on Gambler's dopamine or whatever it is.
15:08
SPEAKER_01: And the issue was I was actually good.
15:10
SPEAKER_01: It was a very niche thing I was good at, but I had an edge.
15:14
SPEAKER_01: The issue was...
15:15
SPEAKER_01: Any time there's an edge in any particular market segment,
15:19
SPEAKER_01: it'll last for a few months, maybe a year, and then it goes away.
15:21
SPEAKER_00: Because everybody else figures out what's going on.
15:23
SPEAKER_00: Other people started playing the game.
15:25
SPEAKER_01: And then a bunch of people started launching SPACs,
15:27
SPEAKER_01: and then there just wasn't enough money to go around, and it just stopped.
15:30
SPEAKER_00: Have you read Spencer Jacobs' book about the GameStop bubble?
15:34
SPEAKER_00: No.
15:34
SPEAKER_01: I do love Spencer Jacobs' stuff.
15:35
SPEAKER_00: I haven't read his book.
15:37
SPEAKER_00: He was a guest on the show a couple years ago.
15:38
SPEAKER_00: The book's great.
15:40
SPEAKER_00: It's just mind-blowing, the confluence of events that happened.
15:44
SPEAKER_00: You had Robin Hood launched,
15:46
SPEAKER_00: pandemic checks went out,
15:48
SPEAKER_00: and you have all these guys your age that are sitting at home with nothing to do,
15:53
SPEAKER_00: and they're like,
15:54
SPEAKER_00: I guess I'll go online and see what's happening in the market today.
15:58
SPEAKER_00: And then boom.
15:59
SPEAKER_00: I remember driving down Peachtree Street and seeing somebody in one
16:03
SPEAKER_00: of these apartment buildings on the ninth floor with a bed sheet spray painted with
16:09
SPEAKER_00: To the Moon on it.
16:10
SPEAKER_01: Yeah.
16:12
SPEAKER_01: It's crazy.
16:13
SPEAKER_01: I mean, I was pretty involved in some of these random chat rooms.
16:16
SPEAKER_01: There were Discord chats where people were pumping pennies.
16:18
SPEAKER_01: It was literally securities fraud.
16:20
SPEAKER_00: Diamond hands, baby.
16:21
SPEAKER_00: Diamond hands.
16:22
SPEAKER_01: There were people who went to court.
16:23
SPEAKER_01: There was this whole group called Atlas Trading where there was a guy...
16:27
SPEAKER_01: Zach Morris from Saved by the Bell.
16:29
SPEAKER_01: There was a Twitter account called Mr.
16:30
SPEAKER_01: Zach Morris who was just pumping penny stock biotech companies.
16:34
SPEAKER_01: He personally made $10 million and he had a paid group chat
16:38
SPEAKER_01: where he would tell them what he would buy and then to
16:40
SPEAKER_01: the free group chat he would send when he was buying an hour later.
16:44
SPEAKER_01: Hey, the president's doing that now.
16:45
SPEAKER_01: Well, it's legal now.
16:47
SPEAKER_01: It's totally fine if it's your own cryptocurrency.
16:50
SPEAKER_01: My favorite stat in financial markets is Trump made more money on Trump coin
16:54
SPEAKER_01: than all crypto companies have made lifetime and net income.
16:59
SPEAKER_01: It's just so good.
17:00
SPEAKER_00: Okay.
17:00
SPEAKER_00: We're not here to talk about meme stocks.
17:03
SPEAKER_00: We're here to talk about your life journey in the book.
17:06
SPEAKER_00: So you make a ton of money.
17:08
SPEAKER_01: And then I stopped making money trading SPACs.
17:12
SPEAKER_01: I'm addicted to trading at this point.
17:13
SPEAKER_01: And I was like, you know what?
17:14
SPEAKER_01: I made money trading this thing.
17:16
SPEAKER_01: I can probably just trade other stocks and keep making money.
17:19
SPEAKER_01: That's like saying, oh, I was really good at football in college.
17:22
SPEAKER_01: Let me now go play volleyball.
17:23
SPEAKER_01: And it doesn't actually work like that.
17:25
SPEAKER_00: Oh, that applies to all aspects of life.
17:27
SPEAKER_00: Right.
17:27
SPEAKER_00: Like going from working at Facebook to comedy, for example.
17:30
SPEAKER_00: Right.
17:31
SPEAKER_00: Surely I'll be just as successful in the creative world as I was in the technology world.
17:35
SPEAKER_00: Facebook's sort of creative.
17:36
SPEAKER_00: But I digress.
17:37
SPEAKER_01: So I end up losing about $150,000 in a day on a bad trade.
17:43
SPEAKER_01: How'd that feel?
17:44
SPEAKER_01: Well, considering that was two and a half times my salary, I just felt like an idiot.
17:48
SPEAKER_01: There's this whole, did you learn anything, whatever.
17:51
SPEAKER_01: I didn't learn anything.
18:10
SPEAKER_01: What I did do was once that blew up and I cut that money more than in half,
18:15
SPEAKER_01: I was like, alright, well that was dumb.
18:17
SPEAKER_01: I could try to trade it back and make it all back.
18:20
SPEAKER_01: That's going to be really annoying if I lose the rest of it or just cash some
18:25
SPEAKER_01: of it out for some fun fuck around money and then leave the rest of
18:29
SPEAKER_01: the retirement account.
18:30
SPEAKER_01: So that's actually what I did.
18:33
SPEAKER_01: So my next thought was, okay, well, this is now August 2021.
18:37
SPEAKER_01: I am going to go to business school in a year.
18:40
SPEAKER_01: What do I want to do for the next year?
18:41
SPEAKER_01: I'm obviously checked out of my corporate finance job.
18:45
SPEAKER_01: Is there anything that's just more interesting to do over the next year,
18:47
SPEAKER_01: pre-business school, that I probably won't be able to do after?
18:50
SPEAKER_01: And the two things that I thought were pretty cool were, I always liked writing.
18:54
SPEAKER_01: I was writing freelance stock articles about the stocks I was looking at.
18:59
SPEAKER_01: And then I'd always wanted to do the classic gap year, backpack Europe type of trip.
19:04
SPEAKER_01: And I'd studied abroad one summer in college,
19:06
SPEAKER_01: but I never did the whole,
19:08
SPEAKER_01: let's just go on an adventure and see what happens with no real goal.
19:12
SPEAKER_01: And that was the thing that I really wanted to do.
19:14
SPEAKER_01: It didn't make financial sense, but from a just pure fun perspective, it made life sense.
19:19
SPEAKER_01: And I had more money.
19:21
SPEAKER_01: I was already budgeting money from my Yeah.
19:51
SPEAKER_01: And she thought I'd just been slacking at work the whole time.
19:54
SPEAKER_01: I told her, hey, you probably thought I was lazy.
19:56
SPEAKER_01: I was actually just addicted to trading stocks.
19:58
SPEAKER_01: She felt a lot better because she was worried about my career development,
20:01
SPEAKER_01: but then realized, I'm not a loser.
20:03
SPEAKER_01: I just wasn't really caring about work.
20:05
SPEAKER_00: Tell me about your grandmother and the trip you took with her.
20:08
SPEAKER_01: Yep.
20:08
SPEAKER_01: So my paternal grandmother,
20:11
SPEAKER_01: Mama Ruth,
20:12
SPEAKER_01: when I was 11,
20:14
SPEAKER_01: she told me that I'm the oldest grandchild,
20:17
SPEAKER_01: and she said she wanted to take me on a trip anywhere in the world.
20:20
SPEAKER_01: And she proceeded to tell my sister and all my cousins this as well.
20:24
SPEAKER_01: I said, okay.
20:25
SPEAKER_01: Like anywhere.
20:25
SPEAKER_01: And she said, yeah.
20:26
SPEAKER_01: And I didn't believe anywhere.
20:27
SPEAKER_01: I meant literally anywhere.
20:28
SPEAKER_01: So at first I pitched like Jamaica or Costa Rica or somewhere pretty close.
20:32
SPEAKER_00: You said Costa Rica in the book.
20:33
SPEAKER_01: It was Costa Rica.
20:34
SPEAKER_00: Which is still pretty good for an 11 year old.
20:35
SPEAKER_00: For sure.
20:36
SPEAKER_01: Yeah.
20:37
SPEAKER_01: I was a huge, but the thing was like, I knew the whole world really well.
20:40
SPEAKER_01: I had a massive map in my room.
20:42
SPEAKER_01: I was like an animal planet, National Geographic nerd.
20:45
SPEAKER_01: And the place I really wanted to go was go on a safari in Africa.
20:48
SPEAKER_01: But I didn't think she'd say yes to that because Tanzania is really far from Georgia.
20:52
SPEAKER_01: Costa Rica is not that far.
20:54
SPEAKER_01: You want to go to Tanzania?
20:56
SPEAKER_01: Exactly.
20:57
SPEAKER_01: That's exactly how she said it.
20:58
SPEAKER_01: Is that right?
20:59
SPEAKER_01: You know the South Georgia accent.
21:01
SPEAKER_01: The way she kept pronouncing Arusha,
21:03
SPEAKER_01: which is one of the capitals as Arushawa, just adding random letters is incredible.
21:10
SPEAKER_01: When I said Costa Rica, she said, Well, is that anywhere in the world?
21:14
SPEAKER_01: Where do you want to go?
21:14
SPEAKER_01: And I said, okay, I actually want to go on a safari to Africa.
21:18
SPEAKER_01: I want to see giraffes and elephants and like Mount Kilimanjaro
21:21
SPEAKER_01: and all this stuff.
21:21
SPEAKER_01: Hell yeah, man.
21:22
SPEAKER_01: And she said, okay, well, give me two weeks to put together an itinerary.
21:26
SPEAKER_01: And then she booked this tour group and we went to get the yellow fever shot
21:30
SPEAKER_01: and like malaria meds and all this stuff.
21:32
SPEAKER_01: And seven months later.
21:33
SPEAKER_00: I would figure growing up in Tifton,
21:35
SPEAKER_00: you'd be immune to yellow fever, given how tropical it can be.
21:38
SPEAKER_01: No, I agree.
21:39
SPEAKER_01: Listen, we were just bathing in gnats, like gnats and mosquitoes.
21:42
SPEAKER_01: For sure, man.
21:43
SPEAKER_01: It was awful.
21:46
SPEAKER_00: I remember two-a-days,
21:47
SPEAKER_00: even in Atlanta,
21:48
SPEAKER_00: which is still a little bit cooler than Tifton,
21:50
SPEAKER_00: I remember two-a-days in that wet grass at like six in the morning.
21:54
SPEAKER_00: It's awful.
21:54
SPEAKER_00: It's the worst thing I've
21:55
SPEAKER_01: ever done.
21:55
SPEAKER_00: Yeah.
21:56
SPEAKER_01: And then south of Macon, you're below the gnat line.
21:58
SPEAKER_01: Right.
22:00
SPEAKER_01: Tifton's not that much hotter than Atlanta.
22:02
SPEAKER_01: It's equally shitty heat,
22:04
SPEAKER_01: but you have like an open scrape on your knee and there's just gnats eating at it.
22:08
SPEAKER_01: It's just gross.
22:08
SPEAKER_01: It's gross.
22:10
SPEAKER_01: Even Macon, where I went to college, right on the gnat lines.
22:13
SPEAKER_01: I was just in gnats for 10 years playing football.
22:15
SPEAKER_01: It was terrible.
22:16
SPEAKER_00: All right, so what did your grandma say?
22:17
SPEAKER_00: I mean, that's the hippest thing a grandma can do.
22:20
SPEAKER_01: She just said, all right, let's do it.
22:21
SPEAKER_01: And then seven months later, we fly to Amsterdam for a layover, and then we fly into...
22:29
SPEAKER_01: I think we flew into Arusha,
22:30
SPEAKER_01: Tanzania and then we were just there for like two and a half weeks
22:33
SPEAKER_01: and it was awesome.
22:35
SPEAKER_00: What was her rationale?
22:36
SPEAKER_00: Her take,
22:37
SPEAKER_00: I asked
22:37
SPEAKER_01: her this a couple years later
22:39
SPEAKER_01: when I was old enough I could actually like have cognitive capabilities.
22:43
SPEAKER_01: Um, I just asked her, what was your impetus for wanting to take me on that trip?
22:49
SPEAKER_01: Because then she proceeded with five of my six cousins who had done the same thing.
22:55
SPEAKER_00: Where did they go?
22:56
SPEAKER_01: I picked the sickest trip.
22:57
SPEAKER_01: My sister was the loser who picked New York,
23:00
SPEAKER_01: and I was just like, come on, you can just do that on your own.
23:03
SPEAKER_01: My little cousin Grady, he wanted to go to Japan, the pandemic hit.
23:06
SPEAKER_01: So he ended up having to do Europe instead and did Italy and Spain.
23:10
SPEAKER_01: Still there.
23:10
SPEAKER_01: Nice.
23:11
SPEAKER_01: I got to come with him because I speak Spanish to be the tour guide.
23:14
SPEAKER_00: Double dosed.
23:15
SPEAKER_01: And then he still got to do Japan with her a year later.
23:18
SPEAKER_01: So he got two trips, which is annoying.
23:19
SPEAKER_01: He did Japan, one cousin did France, and one cousin did China.
23:23
SPEAKER_01: So I think Africa wins the most extreme trip.
23:26
SPEAKER_01: But all the cousins picked cool places.
23:28
SPEAKER_01: My sister was the one who was too lame.
23:30
SPEAKER_00: You set a good bar.
23:30
SPEAKER_00: But Mama Ruth had this great rationale that you are now living out.
23:35
SPEAKER_01: Correct.
23:35
SPEAKER_01: Her whole take was I can either leave my money to my family when I'm dead
23:40
SPEAKER_01: or I can spend it on my grandkids while I'm alive.
23:43
SPEAKER_01: And I think it's a much better use of money to spend more of it now
23:46
SPEAKER_01: while we can all enjoy it than just leave it in a will when I'm dead.
23:51
SPEAKER_01: And it kind of stuck with me in that, you know, it's...
23:55
SPEAKER_01: Especially when you're young,
23:56
SPEAKER_01: it's pretty easy to be hyper-focused on savings rate,
23:58
SPEAKER_01: compounding wealth, and all that stuff is super important.
24:01
SPEAKER_01: I'm very big on you should make money and take care of yourself,
24:04
SPEAKER_01: but this idea of you have a finite window of time to spend money,
24:09
SPEAKER_01: and then within that,
24:10
SPEAKER_01: You have finite windows within your life on the different things you'll want
24:13
SPEAKER_01: to spend money on.
24:14
SPEAKER_01: When she was in her 60s or 70s,
24:16
SPEAKER_01: I'm spending money on my grandkids right now because I'm still able-bodied,
24:20
SPEAKER_01: can get around and have grandkids.
24:21
SPEAKER_00: Yeah, you say stage-specific.
24:23
SPEAKER_00: Life is stage-specific.
24:24
SPEAKER_00: Tell me more about that.
24:26
SPEAKER_01: Money is a pretty fungible thing where you can make and spend the same amount
24:31
SPEAKER_01: of money at any point in your life.
24:33
SPEAKER_01: $1,000 now, $1,000 tomorrow, whatever.
24:35
SPEAKER_01: But the things you actually enjoy spending that money on and the amount
24:39
SPEAKER_01: of enjoyment you'll get out of different life experiences varies wildly.
24:43
SPEAKER_01: If you're in your 20s in New York living with a few of your best friends in
24:47
SPEAKER_01: a three-bed flex one bathroom...
24:50
SPEAKER_01: You're probably having a blast.
24:51
SPEAKER_01: You're going out every weekend.
24:52
SPEAKER_01: You're blowing money on tables and really dumb stuff.
24:55
SPEAKER_01: And it's from a...
24:57
SPEAKER_00: Tables.
24:57
SPEAKER_00: I didn't do...
24:58
SPEAKER_00: I never did any of that stuff.
24:59
SPEAKER_00: I hate tables.
25:00
SPEAKER_01: I think tables are stupid.
25:01
SPEAKER_01: I think there's way more fun ways to enjoy getting drunk in New York City or any...
25:04
SPEAKER_01: A table is just... Every time I've been... That's setting your money on fire.
25:08
SPEAKER_01: It's just like, why?
25:09
SPEAKER_01: We're not enjoying this.
25:11
SPEAKER_01: This isn't...
25:12
SPEAKER_01: It doesn't look cool.
25:13
SPEAKER_01: Like, I...
25:14
SPEAKER_01: Anyway, that's a whole other thing.
25:16
SPEAKER_01: But it's fun to blow money on dumb stuff when you're young.
25:18
SPEAKER_01: And your standard of living is really, really low.
25:21
SPEAKER_01: Or if you want to go travel, you can stay in a bunk bed with 12 strangers in a hostel.
25:25
SPEAKER_00: Frugality is your superpower.
25:27
SPEAKER_01: Right.
25:27
SPEAKER_01: And frugality, you're not even skimping.
25:31
SPEAKER_01: The frugal thing is probably more fun at 24 than the nice thing.
25:35
SPEAKER_01: Living with your two best friends in the East Village versus having
25:39
SPEAKER_01: a kick-ass one bed in Tribeca...
25:42
SPEAKER_01: The former is actually probably more fun at 24.
25:45
SPEAKER_01: You would like to get to the point you can do the latter later,
25:47
SPEAKER_01: but when you're in that I'm going out with my friends all the time
25:50
SPEAKER_01: and everybody's young, it's actually a lot of fun to be fully in that thing.
25:53
SPEAKER_00: You mentioned Bill Perkins' book,
25:55
SPEAKER_00: Die With Zero,
25:56
SPEAKER_00: and I've interviewed him,
25:57
SPEAKER_00: and I remember him talking about when you're older,
26:01
SPEAKER_00: and his theory is give your money away.
26:04
SPEAKER_00: If you want to help your kids, don't wait until you're 80 and they're 55.
26:08
SPEAKER_00: Go to Disney World when they're 80.
26:13
SPEAKER_00: Because if you save and wait when they're 25, they're not going to want to go to Disney World.
26:17
SPEAKER_00: Give them money for a home when they're 32.
26:21
SPEAKER_00: Don't wait until they're 55.
26:22
SPEAKER_00: My dad died when I was 50-something, I think.
26:26
SPEAKER_00: And he left a substantial amount of money, but it didn't change my lifestyle one iota.
26:34
SPEAKER_00: And I was grateful, but it's like, man, that money would have had a huge impact when I was 32.
26:37
SPEAKER_00: I've thought that...
26:43
SPEAKER_01: People talk about consumption smoothing over the course of your life.
26:48
SPEAKER_01: If you've been successful and been fortunate and you get up in your 60s,
26:51
SPEAKER_01: 70s, 80s, yeah, give your kids or grandkids money when they actually need it.
26:55
SPEAKER_01: Because if they're also going to be successful, they won't need it at 55.
26:58
SPEAKER_01: So I totally agree with that.
27:00
SPEAKER_00: Okay, but this applies differently to the way you think.
27:02
SPEAKER_00: So life is stage-specific.
27:04
SPEAKER_00: Yep.
27:05
SPEAKER_00: You, it's funny,
27:06
SPEAKER_00: it's really,
27:06
SPEAKER_00: I gotta tell you man,
27:07
SPEAKER_00: it's really,
27:08
SPEAKER_00: it's heartwarming and funny to listen to a guy who's 29 write with nostalgia
27:14
SPEAKER_00: about being 24.
27:16
SPEAKER_00: And it reminds me of the great times I had in business school.
27:21
SPEAKER_00: 22 to 25 was hard for me.
27:22
SPEAKER_00: My dad gave me the gift of like, you're on your own, go figure it out.
27:25
SPEAKER_00: And I was broke, broke, broke.
27:27
SPEAKER_00: Coming out of business school, late 20s, I'm making a little bit more money.
27:31
SPEAKER_00: I'm living with a very good friend of mine with whom I'm going to Scotland
27:34
SPEAKER_00: to play golf on Friday.
27:36
SPEAKER_00: Nice.
27:36
SPEAKER_00: Right?
27:37
SPEAKER_00: Stage specific.
27:38
SPEAKER_00: We weren't doing this back then.
27:40
SPEAKER_00: Yeah.
27:42
SPEAKER_00: You know, we were having a great time.
27:43
SPEAKER_00: I mean, we're sharing an apartment.
27:45
SPEAKER_00: Who cares?
27:46
SPEAKER_00: We could afford it because we were living together.
27:49
SPEAKER_00: But, like,
27:50
SPEAKER_00: we weren't sitting there thinking,
27:51
SPEAKER_00: God, I wish I had a, you know, 3,000 square foot pad in Tribeca.
27:55
SPEAKER_01: Yeah, you're having a blast living with one of your boys.
27:57
SPEAKER_01: It's like peak life experience.
28:00
SPEAKER_00: So how, like, what's changed from your point, your worldview between then and now?
28:05
SPEAKER_01: I care more about money now at 29 than I did at 24.
28:08
SPEAKER_01: And it's because I'm 29 and single now,
28:11
SPEAKER_01: but I'm much closer to, I would like to get married and have kids in my 30s.
28:16
SPEAKER_01: Okay, that will cost more than my current life does now.
28:19
SPEAKER_00: Yes, it will.
28:20
SPEAKER_00: Especially if you're in New York City.
28:21
SPEAKER_01: Yeah, yeah, yeah.
28:23
SPEAKER_01: That's the rumor.
28:24
SPEAKER_01: A lot of people are saying that these days.
28:26
SPEAKER_01: So that's just not a thing I was worried about at all at 24.
28:30
SPEAKER_01: But the caveat is,
28:32
SPEAKER_01: Part of the reason I took that trip at 24 was because I sort of knew
28:36
SPEAKER_01: that it would play out where I was 24 and single,
28:38
SPEAKER_01: I could go do this fun thing,
28:40
SPEAKER_01: any marginal amount of money I would make then just wasn't going to move
28:43
SPEAKER_01: the needle nearly as much as what I did career-wise post-business school.
28:48
SPEAKER_01: Correct.
28:48
SPEAKER_01: Correct.
28:48
SPEAKER_01: Correct.
29:08
SPEAKER_00: Yeah, that would be a different story.
29:09
SPEAKER_01: I would not go like 25K to credit card debt to go travel the world.
29:14
SPEAKER_01: My take on a lot of this stuff is it's okay to have a lower savings rate
29:18
SPEAKER_01: when you're young if you're focused on increasing your income over time,
29:21
SPEAKER_01: but you shouldn't saddle yourself with debt.
29:23
SPEAKER_01: Like staying near zero longer than is conventional advice I actually think is fine,
29:28
SPEAKER_01: but you don't want to be going underground is my typical take
29:32
SPEAKER_01: on 20-somethings finances.
29:35
SPEAKER_00: Right.
29:36
SPEAKER_00: But now you're thinking with a longer lens.
29:39
SPEAKER_01: Yeah.
29:39
SPEAKER_01: I mean, the whole point of business school was get a pedigree stamp
29:44
SPEAKER_01: that opens up more career opportunities that are like higher leverage
29:47
SPEAKER_01: and more lucrative
29:48
SPEAKER_00: over time.
29:48
SPEAKER_00: You said something interesting
29:49
SPEAKER_00: that juxtaposed following your passion versus what you called interest leading
29:54
SPEAKER_00: to exploration and exploration leading to economic opportunity.
29:58
SPEAKER_00: Yep.
29:59
SPEAKER_00: Talk about that.
30:00
SPEAKER_01: Yeah.
30:00
SPEAKER_01: So I, the thing that I would say I was very passionate about in my mid twenties was writing.
30:05
SPEAKER_01: I enjoyed it.
30:06
SPEAKER_01: I was good at it.
30:07
SPEAKER_01: A lot of people started,
30:08
SPEAKER_01: my Substack subscriber count started going up,
30:11
SPEAKER_01: which is a very good sign that more and more people are reading my stuff.
30:14
SPEAKER_01: And then you have a publisher reaching out to you that you should write a book.
30:17
SPEAKER_01: I was pretty one track minded on going into business school.
30:21
SPEAKER_01: I'd kind of decided that I didn't really want to do the banking consulting route.
30:27
SPEAKER_01: Largely because I ended up working for a media startup pre-business school,
30:30
SPEAKER_01: saw how well they were monetizing.
30:32
SPEAKER_01: I could tell there were opportunities outside of the normal set
30:35
SPEAKER_01: of banker consulting track that could also pay well.
30:39
SPEAKER_01: So for me, writing was taking off.
30:41
SPEAKER_01: I liked it.
30:42
SPEAKER_01: And I thought the right play was to double or triple down on media.
30:46
SPEAKER_01: But the other thing I'd always, always been interested in was investing, investing world.
30:50
SPEAKER_01: Like I had some equity in startups from being an advisor and helping them with stuff.
30:53
SPEAKER_01: I obviously had the whole SPAC trading thing.
30:56
SPEAKER_01: The whole like I put money in things and make money was just a fun game to me.
31:00
SPEAKER_01: And it was two competing things.
31:02
SPEAKER_01: Do I want to do the writing media thing?
31:03
SPEAKER_01: Should I try to use business school to get an investing seat in New York?
31:08
SPEAKER_01: And I kept going back and forth.
31:10
SPEAKER_01: And then I got a job offer from Robinhood to help them build
31:13
SPEAKER_01: a media subsidiary called Sherwood News.
31:15
SPEAKER_01: And at the time, all I could think was...
31:18
SPEAKER_01: It's clever.
31:19
SPEAKER_01: It is.
31:19
SPEAKER_01: Okay.
31:20
SPEAKER_01: They have a massive platform.
31:21
SPEAKER_01: They're putting a lot of money into this.
31:23
SPEAKER_01: They have a lot of email subscribers.
31:25
SPEAKER_01: I have a chance to help build this from the ground up,
31:27
SPEAKER_01: and I'm trying to pitch a book deal,
31:29
SPEAKER_01: and all of this platform,
31:31
SPEAKER_01: like the platform Robinhood has is like very valuable for my book deal pitch.
31:35
SPEAKER_01: We should do this.
31:36
SPEAKER_01: And it was,
31:37
SPEAKER_01: in hindsight,
31:38
SPEAKER_01: like glad I did it initially,
31:40
SPEAKER_01: but it probably wasn't the right move if I'd been a little more thoughtful,
31:43
SPEAKER_01: where writing was always a fun side thing for me,
31:46
SPEAKER_01: but it was never a career primary job focus.
31:49
SPEAKER_01: And I got there and realized that for me it was probably the wrong move and
31:53
SPEAKER_01: a mistake because I didn't...
31:55
SPEAKER_01: The thing I'd always been passionate about and thought was fun,
31:57
SPEAKER_01: the second it became my day job where I'm putting out X number of columns a week,
32:02
SPEAKER_01: podcasts, whatever.
32:03
SPEAKER_00: Writing becomes a chore.
32:05
SPEAKER_01: It did.
32:05
SPEAKER_01: And then I had no bandwidth to work on the actual book and I was like, this...
32:10
SPEAKER_01: This was the wrong trade.
32:11
SPEAKER_01: I took that job during my second year of business school.
32:16
SPEAKER_01: I'm now four months post-graduation,
32:18
SPEAKER_01: seven months into the job,
32:19
SPEAKER_01: and I was just sitting there thinking,
32:21
SPEAKER_01: I'm going to pigeonhole myself as a media content guy,
32:24
SPEAKER_01: and that's not what I want to do.
32:26
SPEAKER_01: And but now I'm on the backside of business school.
32:28
SPEAKER_01: I should have thought this through better a year or two ago and had
32:31
SPEAKER_01: the classic 27 year old career panic and freaked out.
32:35
SPEAKER_01: And then after basically a two week doom spiral of not knowing what I should do,
32:41
SPEAKER_01: I I went back to, OK,
32:43
SPEAKER_01: what things was I interested in that have like higher economic optionality
32:49
SPEAKER_01: and investing world, broadly speaking, was that.
32:51
SPEAKER_01: And then it's like, OK, what realistically can I get into in this world?
32:56
SPEAKER_01: Leveraging the platform I built with all the writing stuff
32:58
SPEAKER_01: where I also will have bandwidth to work on a book.
33:01
SPEAKER_01: I can be self-promotional.
33:02
SPEAKER_01: I won't be a compliance issue.
33:04
SPEAKER_01: And venture capital was kind of the one thing that fit where
33:07
SPEAKER_01: the whole personal brand networking, like it's, it's a deal.
33:10
SPEAKER_01: I ended up looking at probably 20 or 30 different funds to see who was hiring,
33:13
SPEAKER_01: reaching out to people.
33:36
SPEAKER_01: And I started kind of looking for different stuff around August or September of 2024.
33:42
SPEAKER_01: Two months in, had a couple of potential offers, didn't feel like great fits.
33:47
SPEAKER_01: And then I saw that Slow Ventures was hiring.
33:50
SPEAKER_01: I just saw a tweet one of their partners put out.
33:52
SPEAKER_01: It wasn't even a link to the job description.
33:54
SPEAKER_01: It was just a tweet about the hiring process while they were hiring
33:57
SPEAKER_01: and looked them up, found the job application.
33:59
SPEAKER_01: And my current boss, Sam, I believe, had written the whole thing where...
34:05
SPEAKER_01: Basically,
34:06
SPEAKER_01: you're saying they're looking to hire a couple of associates that bring people
34:08
SPEAKER_01: on every few years.
34:09
SPEAKER_01: And I was going down the list of things they were looking for.
34:13
SPEAKER_01: People who had some version of like banking,
34:15
SPEAKER_01: finance, consulting background, but wanted to do something different.
34:19
SPEAKER_01: Prioritizing college athletes and people who were opinionated online
34:23
SPEAKER_01: and had like built something or put themselves out there,
34:26
SPEAKER_01: whether blog, newsletter, podcast, TikTok, Instagram.
34:30
SPEAKER_01: And it just kind of checked all the boxes of I played football in college.
34:33
SPEAKER_01: I have three years of writing online that shows I'm very interested in
34:38
SPEAKER_01: the entire investing world.
34:39
SPEAKER_00: Just everything comes together.
34:41
SPEAKER_01: Yeah, it just made sense.
34:42
SPEAKER_01: And they were hiring in New York and San Francisco.
34:45
SPEAKER_01: And I was like, this is perfect.
34:46
SPEAKER_01: I end up reaching out to the partner in New York.
34:50
SPEAKER_01: We hit it off.
34:51
SPEAKER_01: He introduces me to Sam, who's in San Francisco.
34:54
SPEAKER_01: We hop on a Zoom call.
34:55
SPEAKER_01: I go into that thinking it's like the follow-up interview for the New York job.
35:00
SPEAKER_01: Super excited.
35:01
SPEAKER_01: And he says, what do you think of San Francisco?
35:03
SPEAKER_01: And I say, fentanyl, homeless people, and no nightlife.
35:07
SPEAKER_01: And he was like, well, that's true, I guess.
35:12
SPEAKER_01: You're obviously right.
35:13
SPEAKER_00: Schellenberger, San Francisco.
35:15
SPEAKER_00: Yeah.
35:16
SPEAKER_01: And he was just like, why did you apply at a job in San Francisco?
35:19
SPEAKER_01: And I was just like, dude, I didn't.
35:21
SPEAKER_01: I thought this was an interview for a New York job.
35:23
SPEAKER_01: And he was like, no.
35:24
SPEAKER_01: And I said...
35:27
SPEAKER_01: I don't know.
35:27
SPEAKER_01: Are you interviewing me for the SF job?
35:29
SPEAKER_01: He said, yeah.
35:30
SPEAKER_01: And I was like, huh.
35:32
SPEAKER_00: I mean, I guess if you hire me, I'll move to San Francisco.
35:34
SPEAKER_00: Look, that was the right thing to do.
35:36
SPEAKER_00: Look, you've got to say yes to geographic mobility in your early career.
35:41
SPEAKER_00: 100%.
35:41
SPEAKER_00: You have no leverage.
35:42
SPEAKER_00: Yeah.
35:43
SPEAKER_00: Yeah, just go,
35:44
SPEAKER_00: just go, just say yes, and go, and learn, and do the thing, and see what happens.
35:50
SPEAKER_00: And you don't have to stay there if it doesn't suit you.
35:53
SPEAKER_00: I mean, San Francisco is a miraculous, I was just back there.
35:56
SPEAKER_00: Despite all the press, it's still a magical place.
35:58
SPEAKER_01: I enjoyed it way more than I thought.
36:00
SPEAKER_00: It's spectacular.
36:02
SPEAKER_00: It's not New York, and that's fine.
36:04
SPEAKER_00: And hey, man, you're back where you belong.
36:05
SPEAKER_00: And because you went there...
36:07
SPEAKER_00: You've proved yourself at the company.
36:09
SPEAKER_00: Now you're back living where you want to live and doing what you want to do.
36:11
SPEAKER_01: I will say when I flew out, I mean, I flew out there the first time to meet with Sam in person.
36:16
SPEAKER_01: And taking a Waymo the first time was a magical experience.
36:19
SPEAKER_01: I'm a massive self-driving car guy.
36:21
SPEAKER_01: And most of the footage on Twitter was from 2021, 2022 when the city did objectively
36:26
SPEAKER_00: suck.
36:28
SPEAKER_01: San Francisco is very back.
36:30
SPEAKER_00: Yeah.
36:30
SPEAKER_00: Well, they've got a good mare now and, you know, hopefully he'll keep them on the right path.
36:34
SPEAKER_00: All right.
36:34
SPEAKER_00: I want to talk about a couple of things.
36:36
SPEAKER_00: You said you want to get married and have kids.
36:38
SPEAKER_00: Yeah.
36:39
SPEAKER_00: I'm interested.
36:39
SPEAKER_00: What are the three most important attributes you're looking for in a wife?
36:45
SPEAKER_01: Yeah, that's a good question.
36:46
SPEAKER_01: I guess one probably needs to be shorter than me.
36:48
SPEAKER_00: I'm 6'3".
36:51
SPEAKER_00: What about with Sophie Cunningham?
36:52
SPEAKER_00: What if she came along?
36:53
SPEAKER_01: You know, she is 6'3", right?
36:56
SPEAKER_01: Are we the same?
36:57
SPEAKER_00: She's pretty tall.
36:58
SPEAKER_00: She's quite attractive.
36:59
SPEAKER_01: She is.
37:00
SPEAKER_01: I mean, there's obviously exceptions to everything.
37:02
SPEAKER_01: It's like everything's negotiable.
37:04
SPEAKER_01: Now, actual answers is...
37:08
SPEAKER_01: Ideally, somebody from the South-ish.
37:11
SPEAKER_01: You don't have to be from Tipton, Georgia, or equivalent of that.
37:15
SPEAKER_00: Are you on Farmers Only?
37:17
SPEAKER_01: Yeah, I'm on Farmers Only right now.
37:19
SPEAKER_01: I actually deleted Raya and Hinge, and I'm just Farmers Only and Christian Mingle Maxing.
37:23
SPEAKER_01: It's really good.
37:26
SPEAKER_01: I think having a similar enough background where you share a worldview of...
37:32
SPEAKER_01: It's, I don't know,
37:32
SPEAKER_01: I've gone out with girls who are from New York City proper,
37:35
SPEAKER_01: and I love New York and it's awesome,
37:36
SPEAKER_01: but there's a just different lifestyle expectation and vibe from somebody
37:40
SPEAKER_01: who grew up on the Upper East Side and somebody who moved here from Atlanta
37:44
SPEAKER_01: or Birmingham or Austin or whatever,
37:46
SPEAKER_01: where it just clicks easier because we kind of have the same,
37:50
SPEAKER_01: we are from here, we want to live in this city and do the thing.
37:53
SPEAKER_01: Maybe we want to stay in New York, maybe we don't.
37:55
SPEAKER_00: Okay, worldview.
37:56
SPEAKER_00: I heard worldview.
37:57
SPEAKER_01: Yeah, I would say...
37:58
SPEAKER_00: It was shorter
37:59
SPEAKER_01: worldview.
38:00
SPEAKER_01: Shorter...
38:01
SPEAKER_00: We'll call it a physical match.
38:03
SPEAKER_01: Right.
38:04
SPEAKER_00: Worldview.
38:05
SPEAKER_01: Physical match,
38:06
SPEAKER_01: worldview,
38:07
SPEAKER_01: and just really good sense of,
38:09
SPEAKER_01: you have to be able to riff,
38:11
SPEAKER_01: where I'm a pretty sarcastic guy,
38:13
SPEAKER_01: you don't have to be sarcastic,
38:15
SPEAKER_01: but there's this ability of some people,
38:17
SPEAKER_01: I have friends like this,
38:19
SPEAKER_01: there's girls I've dated like this,
38:20
SPEAKER_01: where if you can just banter and layer a bit on top of a bit,
38:25
SPEAKER_01: it just makes hanging out so much more fun.
38:27
SPEAKER_00: Okay, here's,
38:28
SPEAKER_00: I was thinking about,
38:29
SPEAKER_00: when I wrote that question,
38:30
SPEAKER_00: because I'm interested in,
38:31
SPEAKER_00: you know,
38:32
SPEAKER_00: you've obviously think a lot about life,
38:34
SPEAKER_00: and you think about life stages,
38:35
SPEAKER_00: and I've been married for 19 years,
38:37
SPEAKER_00: and I'm like,
38:37
SPEAKER_00: well, if I'm going to ask that question, I need to be prepared to answer it.
38:40
SPEAKER_00: And so, here's the three things I think are necessary in a spouse.
38:44
SPEAKER_00: Attraction, which is basically what you said.
38:47
SPEAKER_00: Stability and trust as one.
38:50
SPEAKER_00: Like, you need, like, you got to have, you got to be able to, Have emotional stability.
38:55
SPEAKER_00: And then lastly, being on the same page.
38:58
SPEAKER_00: And I think that's worldview slash values.
39:00
SPEAKER_00: You've got to want the same things.
39:02
SPEAKER_00: Because if you don't, it's not going to work.
39:05
SPEAKER_00: Right.
39:06
SPEAKER_00: It's good to know.
39:06
SPEAKER_00: And how's the dating life going?
39:08
SPEAKER_01: I mean, it's certainly more active in New York than it is in San Francisco.
39:11
SPEAKER_00: Especially since you wrote a book?
39:13
SPEAKER_01: Yeah, I mean, writing a book's good.
39:14
SPEAKER_01: I did mention there's a lot of 24-year-old men DMing me now,
39:17
SPEAKER_01: which isn't really what I'm going for.
39:20
SPEAKER_00: Don't close the door.
39:21
SPEAKER_00: You never know.
39:23
SPEAKER_00: San Francisco has a large gay population.
39:25
SPEAKER_01: I've worn off on me a little bit.
39:27
SPEAKER_01: Let's talk about your generation and orientation towards money.
39:31
SPEAKER_00: There was a statistic that Bloomberg put out last week that got a lot of press.
39:35
SPEAKER_00: It was actually,
39:37
SPEAKER_00: I can't remember who put it out,
39:37
SPEAKER_00: but Bloomberg was one of the people who amplified it.
39:40
SPEAKER_00: Bloomberg reported that
39:41
SPEAKER_01: 52% of Gen Z, which you are on the cusp of.
39:44
SPEAKER_01: I am Gen Z.
39:45
SPEAKER_01: You're Gen Z.
39:45
SPEAKER_01: Okay, barely.
39:46
SPEAKER_01: Okay.
39:47
SPEAKER_00: Bloomberg reported that 52% of Gen Z had directed investment funds to sports betting
39:53
SPEAKER_00: in the past year,
39:54
SPEAKER_00: and that 26% treat sports betting as a deliberate part
39:58
SPEAKER_00: of their long-term financial strategy.
40:01
SPEAKER_00: How do you feel about that?
40:02
SPEAKER_01: I mean, look,
40:03
SPEAKER_01: my former employer,
40:04
SPEAKER_01: Robinhood,
40:04
SPEAKER_01: I love opening the app and seeing prediction market,
40:07
SPEAKER_01: sports bet, and then it's the actual stocks I own.
40:10
SPEAKER_01: It's my retirement accounts on Robinhood now.
40:11
SPEAKER_01: They have a great match.
40:13
SPEAKER_01: My actual, like, I don't know.
40:16
SPEAKER_01: I've got nuanced thoughts on this.
40:30
SPEAKER_01: You will budget,
40:35
SPEAKER_01: okay, I will spend a maximum amount of a few thousand dollars in Vegas on a trip.
40:39
SPEAKER_01: Fine.
40:40
SPEAKER_01: That's okay.
40:41
SPEAKER_01: When you can just open your phone and do a parlay of Josh Allen over
40:46
SPEAKER_01: under 250 passing yards,
40:49
SPEAKER_01: 76ers to win the NBA championship,
40:51
SPEAKER_01: color of the Gatorade at the Super Bowl, and you can do that on an investing app.
40:55
SPEAKER_01: I don't think that's a good thing.
40:56
SPEAKER_00: Investing.
40:57
SPEAKER_00: Right.
40:57
SPEAKER_01: Well, I mean, prediction markets are doing this hilarious thing.
40:59
SPEAKER_00: Prediction markets aren't investing either.
41:01
SPEAKER_01: Well, it's funny how they have effectively backed into calling themselves an asset.
41:06
SPEAKER_01: It's like, oh, CFTC says that we are a derivative contract.
41:11
SPEAKER_01: Well, yeah.
41:12
SPEAKER_01: But when the majority of the volume is politics and sports.
41:15
SPEAKER_00: Well, derivatives are gambling, too.
41:17
SPEAKER_00: I mean, if you're,
41:17
SPEAKER_00: you know,
41:18
SPEAKER_00: if you're 24 and you're,
41:20
SPEAKER_00: you know, playing options, that's not a great strategy either.
41:23
SPEAKER_01: I had a tweet about this the other day or my take on prediction
41:26
SPEAKER_01: because they make their whole marketing thing.
41:28
SPEAKER_01: Oh, we are a hedging asset and you can like.
41:31
SPEAKER_01: Oh, bullshit.
41:32
SPEAKER_01: You can make money on your expertise.
41:34
SPEAKER_01: Yet, like, Calcio.
41:34
SPEAKER_01: You can.
41:36
SPEAKER_01: Calcio put out this thing showing, look at what percent of traders are making money in New York.
41:40
SPEAKER_01: And it's like, huh.
41:41
SPEAKER_01: All the high-frequency trading firms have to be based in New York.
41:44
SPEAKER_01: I wonder if they're the ones making the money or the retail investor
41:47
SPEAKER_00: in his Hell's Kitchen apartment.
41:48
SPEAKER_01: It's a transfer of money from retail investors who are gambling
41:52
SPEAKER_01: to sophisticated quants, which I guess is a sufficient use of capital.
41:57
SPEAKER_01: But the issue is you have a lot of young people who...
42:02
SPEAKER_01: I think the biggest problem with social media is that your comparison group
42:06
SPEAKER_01: of how you're doing in life expands from people you know from school or work to
42:10
SPEAKER_01: the entire world where you can be in your 20s and making six figures
42:14
SPEAKER_01: and objectively you're in a very good spot in life but feel like you're way behind
42:18
SPEAKER_01: the person who joined the hot startup that ripped or the entrepreneur who sold
42:22
SPEAKER_01: a company or the hedge fund analyst whose fund had a good year and you think,
42:25
SPEAKER_01: oh man, They're making way more money than me.
42:28
SPEAKER_01: I need to catch up.
42:30
SPEAKER_01: And when you don't have that much money saved up,
42:33
SPEAKER_01: it's really easy to convince yourself to risk the farm on a one-off moonshot where
42:38
SPEAKER_01: the odds are really stacked against you.
42:40
SPEAKER_01: But if it hits, you make a lot of money.
42:42
SPEAKER_01: And a certain number of people will hit that where I think a lot
42:45
SPEAKER_01: of people are now doing the,
42:47
SPEAKER_01: I don't give a shit about compounding or building wealth over 20 years.
42:50
SPEAKER_01: I'm never going to buy a home if I do that.
42:52
SPEAKER_01: I'd rather pull that forward, like,
42:55
SPEAKER_01: Play roulette, see if it hits, and if it doesn't,
42:58
SPEAKER_00: whatever, I have less saving.
42:59
SPEAKER_00: One of the many issues with that problem,
43:01
SPEAKER_00: and it is a problem, is that what you're looking at is a snapshot.
43:05
SPEAKER_00: And it's just the next decade's version of peaking in high school.
43:11
SPEAKER_00: The objective isn't to be winning in your 20s.
43:14
SPEAKER_00: The objective is to be thriving in your 50s.
43:20
SPEAKER_00: It's hard to think about that when you're 26, 27.
43:24
SPEAKER_00: But really,
43:26
SPEAKER_00: what you can see in hindsight is like,
43:28
SPEAKER_00: oh yeah, that dude was killing it at 28 or 38 or whatever.
43:33
SPEAKER_00: And then all this other shit happened to him.
43:36
SPEAKER_00: Whether it was financial or personal or,
43:37
SPEAKER_00: you know,
43:38
SPEAKER_00: he got cocky and he made all this money and he got divorced and lost half his money
43:42
SPEAKER_00: and blah, blah, blah.
43:43
SPEAKER_00: So it's like a whole,
43:44
SPEAKER_00: you got to see the whole field,
43:46
SPEAKER_00: not just one variable that people are optimizing for.
43:50
SPEAKER_01: And once you start playing that I'm going to risk it all on a negative EV bet and you miss it.
43:57
SPEAKER_01: Every time you do that,
43:57
SPEAKER_01: that actually sets you a little bit further back,
43:59
SPEAKER_01: both from the time suck of spending time messing around
44:02
SPEAKER_01: on sports betting versus doing other stuff that actually compounds your life,
44:07
SPEAKER_01: and on the actual money of if you lose $10,000 here.
44:10
SPEAKER_01: Again,
44:10
SPEAKER_01: I'm big on spending money when you're young on experiences that stick with you
44:14
SPEAKER_01: that are like Bill Perkins uses the term memory dividends.
44:17
SPEAKER_01: I think it's a great term.
44:18
SPEAKER_01: Spending $10,000 on an awesome experience when you're young is great.
44:23
SPEAKER_01: Blowing $10,000 on sports betting is actually the opposite of that.
44:26
SPEAKER_01: Right, because you get nothing from it.
44:28
SPEAKER_01: You lose money that could have compounded and you didn't spend it
44:31
SPEAKER_01: on something you actually enjoyed.
44:32
SPEAKER_01: And then you feel further behind the eight ball.
44:35
SPEAKER_01: So then next time you have money in your bank account, you'll gamble it again.
44:37
SPEAKER_01: The removal of friction, the gamification of these apps.
44:52
SPEAKER_00: This is what makes them so dangerous.
44:54
SPEAKER_00: And I mean, you can do it at two o'clock in the morning when you're hammered.
44:57
SPEAKER_00: That's not good.
44:58
SPEAKER_00: Now, again, this is an investment show, no investment advice.
45:01
SPEAKER_00: I just am interested in your thoughts.
45:03
SPEAKER_00: Bitcoin's at $64,000 today.
45:05
SPEAKER_00: How much does it trade for in a year and in five years?
45:08
SPEAKER_01: Well, this is a store of value, probably $64,000 forever.
45:11
SPEAKER_01: No.
45:13
SPEAKER_01: My take on Bitcoin is I think as an asset it's actually worthless,
45:17
SPEAKER_01: but because enough people think it's worth something, it will never go to zero.
45:22
SPEAKER_01: Like art?
45:24
SPEAKER_01: Well, art you can actually look at.
45:26
SPEAKER_01: Bitcoin you can't.
45:29
SPEAKER_01: I'm not going to give a price prediction, but I think there's a real risk.
45:32
SPEAKER_01: I have a buddy who had Bitcoin.
45:33
SPEAKER_01: He had $2 million or $1.8 million of Bitcoin in a cold wallet.
45:38
SPEAKER_01: Yeah.
45:38
SPEAKER_01: Yeah.
45:58
SPEAKER_01: AI gets really, really good.
45:59
SPEAKER_01: Is there a point at which there's enough security breaches from this?
46:03
SPEAKER_01: Bitcoin's only worth something because there's a collective amount of trust saying
46:06
SPEAKER_01: that it should be worth something,
46:08
SPEAKER_01: where if people get really good at using basically AI coding tools
46:12
SPEAKER_01: to hack people's wallets, does that make people...
46:15
SPEAKER_01: Even a Bitcoin itself doesn't change.
46:17
SPEAKER_01: Do people trust it less because they're worried theirs will get stolen?
46:21
SPEAKER_01: The whole point of crypto is, well, there's no institutions that protect your money.
46:25
SPEAKER_01: It's just on you.
46:26
SPEAKER_01: If money gets drained from your account at JPMorgan Chase,
46:30
SPEAKER_01: you call the bank, they'll probably make you right.
46:32
SPEAKER_01: If you lose your Bitcoin, sorry, somebody else has it now.
46:35
SPEAKER_01: I actually think the biggest risk for it is mass loss of trust if too many people get hacked.
46:41
SPEAKER_01: So, I don't know.
46:42
SPEAKER_01: I think a year from now, it probably trades up from here.
46:45
SPEAKER_01: I think five years from now.
46:47
SPEAKER_01: I think at some point,
46:47
SPEAKER_01: if we don't hit a broad crypto bear market,
46:49
SPEAKER_01: it probably starts going back up toward $100K.
46:52
SPEAKER_01: I think we're a couple of massive...
46:55
SPEAKER_01: Just security breaches away from people losing trust where it never goes to zero.
47:00
SPEAKER_01: But this whole, oh man, I have $100 million in Bitcoin.
47:04
SPEAKER_01: I've been long Bitcoin my whole portfolio for 10 years.
47:07
SPEAKER_01: Am I still comfortable doing that when people who thought their wallets were safe get drained?
47:11
SPEAKER_01: Probably not.
47:11
SPEAKER_01: I'm probably going to sell.
47:13
SPEAKER_01: So I think it trades higher in a year, lower in five years.
47:16
SPEAKER_00: All right.
47:16
SPEAKER_00: We're going to do a thing called true or false.
47:18
SPEAKER_00: Okay.
47:18
SPEAKER_00: All right.
47:18
SPEAKER_00: True or false.
47:20
SPEAKER_00: Memento mori is Latin for sauce on the side.
47:23
SPEAKER_00: True.
47:24
SPEAKER_00: False.
47:26
SPEAKER_00: True or false.
47:27
SPEAKER_00: Your 20s is a decade when it's rational to make irrational financial decisions.
47:31
SPEAKER_00: 100% true.
47:32
SPEAKER_00: True or false, Gen Z has it worse than any generation that came before it?
47:36
SPEAKER_00: False.
47:37
SPEAKER_00: Gen Z has it awesome.
47:38
SPEAKER_00: True or false,
47:39
SPEAKER_00: if you gave every 22-year-old in America $1 million today,
47:42
SPEAKER_00: they would be worse off in 10 years?
47:44
SPEAKER_00: False.
47:45
SPEAKER_00: True or false,
47:46
SPEAKER_00: a 27-year-old with $200,000 in the bank and no good stories is less well-off than
47:49
SPEAKER_00: a 27-year-old with $10K and a passport full of stamps?
47:52
SPEAKER_01: True.
47:53
SPEAKER_00: True or false, FanDuel is a great place to start building your retirement portfolio?
47:58
SPEAKER_01: Once they open Roth IRAs, why not?
48:02
SPEAKER_01: I don't know.
48:04
SPEAKER_01: I doubt they do, but I don't know.
48:06
SPEAKER_01: I was a DraftKings guy.
48:08
SPEAKER_00: All right, Jack, it's really great to meet you.
48:11
SPEAKER_00: I'm glad you've shared your story with the world.
48:14
SPEAKER_00: It's fun to,
48:14
SPEAKER_00: like I said,
48:15
SPEAKER_00: read about,
48:16
SPEAKER_00: to see the world through the lens of somebody who's
48:19
SPEAKER_01: Like me, but 30 years younger.
48:20
SPEAKER_01: Some Georgia guys in the city.
48:22
SPEAKER_00: Well, you know, we're just trying, man.
48:24
SPEAKER_00: We're just doing our best at both stages of our life.
48:27
SPEAKER_00: So what do you want?
48:28
SPEAKER_00: If you're talking to somebody my age who's got a 20-something-year-old kid,
48:31
SPEAKER_00: why should they buy the book for their child?
48:33
SPEAKER_01: Look, at the end of the day,
48:34
SPEAKER_01: most life advice books are written by people way older than you that are trying
48:37
SPEAKER_01: to push their 40-, 50-, 60-year-old lessons on the younger person.
48:41
SPEAKER_01: And if you're in your 20s, you're like, okay, this isn't relatable.
48:45
SPEAKER_01: Young Money is basically a memoir from late 20s,
48:48
SPEAKER_01: I think the book's incredibly relatable and just puts people at ease
48:50
SPEAKER_01: because it reminds them that it's okay to feel like this.
48:52
SPEAKER_01: Here's some helpful ways to think about making these decisions.
48:54
SPEAKER_01: Because the defining attribute of your 20s is...
49:18
SPEAKER_00: Uncertainty.
49:19
SPEAKER_00: Correct.
49:20
SPEAKER_00: And everybody experiences it.
49:22
SPEAKER_00: That's right.
49:23
SPEAKER_00: And that's okay.
49:23
SPEAKER_00: That's right.
49:24
SPEAKER_00: The book is called Young Money.
49:26
SPEAKER_00: Where can we find it?
49:27
SPEAKER_01: Amazon, Barnes & Noble, audiobook on Spotify, Apple.
49:31
SPEAKER_01: I recorded it.
49:32
SPEAKER_01: If you like my voice, listen to it.
49:33
SPEAKER_01: If you hate it, listen to it a little bit faster.
49:36
SPEAKER_01: Anywhere you buy books, you can find Young Money.
49:38
SPEAKER_00: And what's your substack?
49:39
SPEAKER_01: Youngmoney.co.
49:41
SPEAKER_00: Cool.
49:41
SPEAKER_00: We'll put a link to it in the show notes.
49:43
SPEAKER_00: Let's go.
49:43
SPEAKER_00: Jack, great to meet you, man.
49:44
SPEAKER_01: Thanks, man.
49:45
SPEAKER_00: Jack Raines, ladies and gentlemen.
49:47
SPEAKER_00: What a guy.
49:48
SPEAKER_00: 29 years old.
49:49
SPEAKER_00: He's kicking ass.
49:51
SPEAKER_00: He's giving it his very best.
49:53
SPEAKER_00: Not afraid to put himself out there to say things he thinks about.
49:56
SPEAKER_00: It'll be interesting to see 10 years from now.
49:59
SPEAKER_00: I wonder what he'll find that he got right and what he got wrong.
50:02
SPEAKER_00: But at least he's thinking about it.
50:03
SPEAKER_00: At least he's trying to keep the big picture in mind.
50:05
SPEAKER_00: When I was 29 years old,
50:09
SPEAKER_00: I wasn't thinking about the big picture.
50:10
SPEAKER_00: The big picture was just go kick ass and make as much money as you possibly can.
50:15
SPEAKER_00: Find a girl, you know, that kind of thing.
50:18
SPEAKER_00: And he seems to be both self-aware and totally unafraid all at the same time.
50:25
SPEAKER_00: And I think that energy is pretty incredible.
50:28
SPEAKER_00: I wouldn't be surprised if we see Mr.
50:30
SPEAKER_00: Raines in political office someday because I just think people kind of...
50:35
SPEAKER_00: Warm to that kind of energy.
50:37
SPEAKER_00: All right, let's think about what we got going on here.
50:40
SPEAKER_00: Uncertainty.
50:41
SPEAKER_00: He says uncertainty is the defining emotion or orientation during your 20s.
50:47
SPEAKER_00: And I think he's right about that.
50:50
SPEAKER_00: Uncertainty is what makes your 20s both beautiful and completely horrible.
50:58
SPEAKER_00: If you go through the typical career path, you start your 20s, you're halfway through college.
51:04
SPEAKER_00: As a man anyway,
51:05
SPEAKER_00: your brain isn't even fully formed until you're almost halfway through your 20s.
51:11
SPEAKER_00: And then you exit on the other side of it,
51:14
SPEAKER_00: if you're lucky,
51:16
SPEAKER_00: with a much better head on your shoulders than you began the decade.
51:22
SPEAKER_00: Maybe you have a little less hair.
51:23
SPEAKER_00: Maybe you got a little paunch.
51:25
SPEAKER_00: Or maybe you've worked it off because whatever you were doing in college and as
51:28
SPEAKER_00: a kid, you've decided that your priorities are to be a healthier, stronger adult.
51:34
SPEAKER_00: But the amount of growth you go through in your 20s is just astounding.
51:39
SPEAKER_00: So I think it's a really interesting time for somebody who's still in it to write
51:43
SPEAKER_00: about and reflect on.
51:44
SPEAKER_00: I don't think we get,
51:46
SPEAKER_00: you know,
51:46
SPEAKER_00: a lot of management books and memoirs and stuff are written by people who are
51:50
SPEAKER_00: a lot older.
51:50
SPEAKER_00: And of course,
51:51
SPEAKER_00: you know,
51:51
SPEAKER_00: you have a little bit more perspective when you're older,
51:53
SPEAKER_00: but you lose that sort of like vibrant enthusiasm that Jack still has just
52:01
SPEAKER_00: because life, you know, even if things go great, life kicks you in the teeth.
52:05
SPEAKER_00: Gravity pulls on parts of your body, including your hair and other parts.
52:11
SPEAKER_00: You get worn down, quite literally, in fact.
52:14
SPEAKER_00: Anyway, did I just talk about drooping?
52:16
SPEAKER_00: I don't... Never mind.
52:18
SPEAKER_00: Never mind.
52:19
SPEAKER_00: If you're still listening, I apologize.
52:21
SPEAKER_00: Okay, what else are we going to talk about?
52:23
SPEAKER_00: I don't think nature wants 24-year-old guys to have a lot of money.
52:30
SPEAKER_00: And the reason is because...
52:33
SPEAKER_00: We would self-destruct.
52:35
SPEAKER_00: A lot of us would self-destruct.
52:39
SPEAKER_00: You're still in that phase at that age where you're just like, yeah, let's go do that.
52:45
SPEAKER_00: Should I drive 100 miles an hour?
52:47
SPEAKER_00: Yeah, let's go do that.
52:49
SPEAKER_00: Should I do 37 shots at the bar on a Tuesday night?
52:52
SPEAKER_00: Yeah, let's go do that.
52:54
SPEAKER_00: Should I sleep with somebody that...
52:57
SPEAKER_00: Is a really bad idea to sleep with 100%.
53:00
SPEAKER_00: And all those things interact such that you make these just terrible, terrible decisions.
53:07
SPEAKER_00: Hypothetically, I'm not talking about myself here.
53:09
SPEAKER_00: I'm saying hypothetically a person makes horrible,
53:12
SPEAKER_00: horrible decisions in their 20s until they learn from negative feedback,
53:18
SPEAKER_00: the big bonk on your forehead from life that says,
53:21
SPEAKER_00: wait, why do I feel horrible on a Wednesday morning?
53:24
SPEAKER_00: Oh, it's because I did shots last night on a Tuesday.
53:27
SPEAKER_00: Maybe that's not a great idea.
53:29
SPEAKER_00: Why did I wake up next to somebody I shouldn't have woken up next to?
53:33
SPEAKER_00: Maybe that's not something I should be doing going forward.
53:36
SPEAKER_00: You know, and you learn a little bit.
53:38
SPEAKER_00: You get kicked in the teeth by life a little bit and you get smarter and you start
53:42
SPEAKER_00: to go, oh, hang on a second.
53:43
SPEAKER_00: What do I want from life?
53:46
SPEAKER_00: And do these things feed in to what I want from life?
53:49
SPEAKER_00: It's what Jack's talking about here.
53:52
SPEAKER_00: He's basically saying like, start from death and work backwards.
53:55
SPEAKER_00: Probably about when I was 23 or 24,
53:59
SPEAKER_00: I was living in Memphis,
54:00
SPEAKER_00: Tennessee, working in development at Rhodes College where I went to school.
54:05
SPEAKER_00: I was not a grownup yet and I was acting like a moron.
54:10
SPEAKER_00: And I was at a bar one night and I talked this girl into coming back to my place.
54:15
SPEAKER_00: She made it quite clear That she wasn't going to make out with me or anything else.
54:22
SPEAKER_00: But she slept on my couch.
54:23
SPEAKER_00: I don't know why.
54:24
SPEAKER_00: Maybe she was in a fight with her roommate or with the person she was visiting.
54:27
SPEAKER_00: She was from out of town.
54:29
SPEAKER_00: She's also a big time executive now, so I'm not going to say who she is.
54:32
SPEAKER_00: But anyway, she comes back to my place, sleeps on the couch.
54:36
SPEAKER_00: We have a perfectly nice visit, but nothing happened.
54:39
SPEAKER_00: The next morning, I'm driving her back to wherever she was staying.
54:42
SPEAKER_00: And she looks at me and she goes, why don't you have a girlfriend?
54:46
SPEAKER_00: And I was like, huh.
54:49
SPEAKER_00: Why don't I have a girlfriend?
54:50
SPEAKER_00: And I just remember that question.
54:53
SPEAKER_00: And on the way home,
54:54
SPEAKER_00: I was like,
54:54
SPEAKER_00: I don't have a girlfriend because I'm acting like an idiot because I'm a loser
54:58
SPEAKER_00: because I don't have my shit together.
55:01
SPEAKER_00: And it was right about this time that I started to think, what do I want from life?
55:06
SPEAKER_00: What are the things that are going to help me live the kind of life that I want to live?
55:12
SPEAKER_00: Well, you go, okay, well, someday I want to get married.
55:15
SPEAKER_00: Am I going to marry the girl I want to marry if I act like a total moron?
55:18
SPEAKER_00: No.
55:18
SPEAKER_00: Am I going to have the money and the financial stability that I want to have
55:22
SPEAKER_00: if I act like a moron?
55:23
SPEAKER_00: No.
55:25
SPEAKER_00: And not knowing exactly what my long-term plan was,
55:28
SPEAKER_00: it was about that time that I said, you know what?
55:30
SPEAKER_00: I think I need to get my act together professionally.
55:32
SPEAKER_00: I need to figure out what I want to do long-term.
55:35
SPEAKER_00: And I think I'm going to do that by going to business school.
55:38
SPEAKER_00: And if I'm going to go to business school,
55:39
SPEAKER_00: I'm going to go to the very best business school I can possibly get into.
55:43
SPEAKER_00: And I had no money at the time.
55:44
SPEAKER_00: But I had time.
55:46
SPEAKER_00: So I went to Barnes and Noble.
55:48
SPEAKER_00: I think I talked about this in the interview,
55:50
SPEAKER_00: but I went to Barnes and Noble and bought an SAT prep book and sat down
55:53
SPEAKER_00: at my kitchen table and studied and I did well on the GMAT.
55:56
SPEAKER_00: And I got into a great business school.
55:59
SPEAKER_00: Took school at Dartmouth.
56:01
SPEAKER_00: Anyway, that's not the point.
56:02
SPEAKER_00: The point here is there's this transformation in your 20s when you get out of school.
56:08
SPEAKER_00: Everybody's on a different journey, but this was what it was for me.
56:10
SPEAKER_00: I got out of school.
56:12
SPEAKER_00: I thought life was going to be easy.
56:14
SPEAKER_00: It wasn't easy.
56:16
SPEAKER_00: And I was like,
56:17
SPEAKER_00: why is this not kind of like As simple and straightforward as high school
56:22
SPEAKER_00: and college were because those were,
56:24
SPEAKER_00: you just go there and you do well in your classes and you run for office
56:27
SPEAKER_00: or whatever you do and then people like you and then you do well.
56:29
SPEAKER_00: No, the whole adult world is different and you got to figure it out.
56:33
SPEAKER_00: And it's by making mistakes and dusting yourself off and getting back up and getting back at it.
56:39
SPEAKER_00: And it's from rhetorical questions from girls who won't kiss you when you're 23
56:44
SPEAKER_00: and they say, why don't you have a girlfriend?
56:45
SPEAKER_00: And you go, I better get my shit together.
56:48
SPEAKER_00: That's how life starts.
56:50
SPEAKER_00: Oh, anyway,
56:51
SPEAKER_00: long takeaway here to say maybe if you got a 20-something guy or girl in your life,
56:58
SPEAKER_00: daughter,
56:59
SPEAKER_00: niece, nephew, son, cousin, whatever, maybe they'd benefit from Jack's words.
57:05
SPEAKER_00: It's not a prescription for housework.
57:06
SPEAKER_00: So start putting yourself on the path to being the person you want to be now.
57:09
SPEAKER_00: All right.
57:09
SPEAKER_00: Thanks a bunch.
57:11
SPEAKER_00: Hope you enjoyed that conversation.
57:12
SPEAKER_00: See you next week.