You Can't Buy Back Your 20’s — with Jack Raines

Paula Pant (0:00)

How should you spend money in your 20s? A lot of people approach that question through the lens of tactics, but I want to zoom out and talk about the philosophy, the life. What kind of life do you want to build through the way that you spend money in your 20s?

I'm not talking about compound interest, blah, blah, blah. We all know about that. I'm talking about what are the things that you can do only in your 20s, that you're not going to be able to do in your 40s? What are the things that are worth spending money on? We're going to have that discussion today with the author of Young Money, Jack Raines. Welcome to the Afford Anything Podcast, the show that knows you can afford anything, not everything, and saying yes to some things implicitly means saying no to other things. That involves trade-offs, opportunity costs of the ways that you spend money in your 20s or in your 30s versus how you spend money in your 50s and 60s. We're going to have that age-based discussion today. I'm your host, Paula Pant, and our guest is Jack Raines. I first heard of him probably a year or two before I met him. He is a recent graduate, MBA graduate of Columbia, which is where I first heard about him. He had a, even then, had a reputation as someone with a lot of thoughts around business, around money. He has a very popular substack, and he just came out with his first book called Young Money, all about the philosophy of how to spend money in your 20s. Here he is, Jack Raines.

Hi, Jack.

Jack Raines (1:30)

Hi, Paula.

Paula Pant (1:31)

When you were in your early 20s, you matched with your boss on Hinge. Yes, I did.

Jack Raines (1:36)

Well, actually, I wouldn't say that I matched with her. I did like my boss on Hinge. It was not reciprocated.

Paula Pant (1:43)

Then you saw her at a Braves game, multiple beers deep, and drunkenly told her that you were quitting.

Jack Raines (1:50)

Right.

Paula Pant (1:51)

Tell us that story.

Jack Raines (1:53)

I should add a little bit of context to this. It was like summer 2021 I was working in corporate finance in Atlanta, Georgia, and I was just fed up with it was a year and a half of COVID, working remote the whole time. I knew I was going to grad school in a year, and I was pretty set at this point on just quitting my job and going and backpacking Europe, very 24-year-old shenanigans.

Around that time, I had broken up with a girl I was dating, and I did see my boss on Hinge.

I actually thought it would be really funny to engage, which I do not recommend doing this. This is a totally bad idea. But she had one of those, I think the prompt said, it was something like, what's your ideal day? And she had put like day drinking by the pool with friends. And I was like, I had a pretty funny reply to that. I replied and said, same, especially on Wednesdays after work, but don't tell my boss.

Anyway, obviously, there was no engagement on the other end. And then I actually had a meeting with my boss. We had a standing meeting on Mondays. And I was sitting there thinking, I wonder if I'm gonna get fired. Like, I went to that meeting on Monday, wasn't brought up at all. And then I was at a Braves game with some buddies, like a month, month and a half later, run into her there. There's like a lot of bars around the Braves stadium. And yeah, it was three beers deep. We like made eye contact. She waved. I hadn't seen her since like COVID hit. Like I was in the office for one week when COVID hit. So anyway, I'd seen her in like a year and a half, walk over, say, hey, we're like riffing back and forth for 10 minutes. And she was kind of complaining about work over the last couple of weeks and how she had to work on the weekend. I was like, huh, I think I'm going to quit in a couple of months. She said, what? And I was just like, I don't know. Like, it doesn't really seem like you're loving this right now. And if I got promoted, I would be doing what you're doing. And I like, yeah, I think I'm just going to leave. And she was like, you're telling me that at a bar. And I was like, I am, I am like, this is kind of mutually assured destruction since we're both talking about this right now. So a month later, I texted her and said, hey, she said, let me guess, you're like about to quit. And I was like, yeah. And she thinks I have another job lined up. And I just said, no, I'm going to Barcelona. I found a plane ticket for like 250 bucks.