Afford Anything - Your 20s Are a Unique Window: Why You Should Optimize for Adventure Before Career - with Jack Raines

Episode Date: August 14, 2026

#740: Jack Raines turned $6,000 into $400,000 trading blank-check stocks during the 2020–2021 bubble — and he says it was some of the least fun money he's ever made. Jack Raines is a writer and investor at Slow Ventures, and the author of the new book Young Money: A Field Guide to Wealth and Purpose in Your Twenties. In this episode, we discuss: Why "golden handcuffs" are almost always a choice, not a trap How to tell if you're staying in a job for the right reasons, or just fear Why the same decision can be exactly right at 24 and wrong at 34 What actually helps when comparison and "falling behind" turn into apathy How he turned $6,000 into $400,000 trading a stock bubble, then gave much of it back Why hitting your number rarely feels like the finish line people expect Two questions worth asking before you spend years on something that isn't working This one's for anyone who feels behind, stuck, or unsure if their current path is a smart trade-off or just fear in disguise — Jack's way of thinking about money and time might be the reset you need. ⏱️ TIMESTAMPS Note: Timestamps may vary slightly depending on dynamic ad placements. (02:00) He liked his boss on a dating app (06:57) Two very different ways to spend your twenties (17:56) Why grad school became his built-in sabbatical (19:16) Why 30 gets judged harder than 24 (34:12) The real cause of career apathy (39:20) His best fix for feeling stuck (46:27) Same decision, right at 24, wrong at 34 (01:01:43) What's really keeping you in a job you hate (01:14:12) Why more money doesn't fix stress (01:17:56) Turning $6,000 into $400,000 in a stock bubble 🔗 RESOURCES MENTIONED 👉 Take the free 10-day FiiRE money-mindset workbook: if "I make too much to quit" sounds familiar, this helps you find out if that's actually true. → https://affordanything.com/fiire 👉 Jack's new book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties → https://jackraines.blog/book 👉 Nick Maggiulli's The Wealth Ladder, the six-level wealth framework Paula references → https://www.amazon.com/Wealth-Ladder-Proven-Strategies-Financial/dp/0593854039 👉 Freedom, the app Jack and Paula both use to block social media and protect focus time → https://freedom.to Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. And that involves tradeoffs, 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. So 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.

Hi, Paula. When you were in your early 20s, you matched with your boss on Hinge. Yes, I did. Well, actually, I wouldn't say that I matched with her. I did like my boss on Hinge. It was not reciprocated. And then you saw her at a Braves game, multiple beers deep, and like drunkenly told her that you were quitting. Right.

Tell us that story. So I should have a little bit of context to this. So it was like summer 2021. I was working in corporate finance in Atlanta, Georgia, and I was just kind of like 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 like pretty set at this point on just quitting my job and like 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 and I actually thought it would be really funny to like

engage, which I don't, I do not recommend doing this. This is like until. 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 like engagement on the other end. And then I actually had a meeting with my boss. We had like a standing meeting on Mondays. And I was sitting there thinking, I wonder if I'm going to get fired. Like, you know what I'm meeting on Monday? Was brought up at all. And then we were at, 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 Brave 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 see 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. And 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, like, yeah, I think I'm just going to leave. 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 text 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. When I did quit, I went to turn in my computer. And I'm a big, I think writing notes are important, sentimental, whatever. And anytime I've left a job, I've always written my boss a thank you note.

And the one to her at the end, I put P.S. I really thought you would have at some point said something about that hinge message. I know it was funny. And she texted me after. And she was like, thank you for the note. Very sweet. Like, let me know if you ever need like a job. referral, whatever. And she said, I did think the message was hilarious. I obviously just wasn't going to engage with that. She's now like married and I think has a kid. So I'm not. So anyway, everything worked out as it should have. But that did happen.

I raised the story in part because as you guys were sitting at the bar and she was complaining about having to work over the weekend, I mean, it's a funny story generally, but it also is a little bit insightful because you were seeing the path that your life would take. Like if you continued down that road, if you got the promotion that would elevate you to her position, you were seeing what that work life would be like. and based on the way that she was reporting it, it kind of sucked. Yep. Yeah, that was my take. Yes. You write about a philosophy of how to be in your 20s. And a big piece of that is particularly in your early 20s.

And you differentiate between early 20s and late 20s. We'll talk more about that in a minute. But particularly in early 20s, you're maximizing for adventure and flexibility. Yep. My take on this, and I think everything about how you should spend your time is so nuanced and situationally dependent. For me, I was in a situation where I kind of knew what my late 20s were going to look like because I'd gotten into business school and kind of knew that I would move to New York for business school at 25 or 26 and would have a certain career path after that.

So I kind of had this window from 22 to 25 where I was, I kind of just had to figure out what to do for three years. Broadly speaking, there's like two pretty interesting ways to spend your early 20s, you either go really hard after the, like, difficult to get high achieving, high paying job, like investment banking, whatever, or you do something like really weird and different where you know that like your cost of living is incredibly low when you're 23. Your burn rate is really low. Like, you don't really have that much money saved up. So you don't have that much to lose in the first place.

Like your worst case scenario is you flame out of whatever you're trying to do and you go home and find a part-time job for a few months. something that I like always really romanticized was it'd be really cool to go like backpack Europe and Latin America. I'm a big Anthony Bourdain fan. I always like this idea of, oh, there's all these cool countries out there I want to go see. And I'd studied abroad. I'd gone to France one time with some friends. I'd been out of the country before, but it was like a month at a time or a few weeks at a time.

And it was just in the back of my head, I think everybody has something they want to do when they're young. in mind was how much of the world can I see and make an adventure out of it. Staying in hostels, doing it cheaply, like partying with random people. I just want to lean into that. The thing I kind of realized at 23 or 24 was there was this really finite window of when I could do that cheap thrill-seeking travel where it would be super fun. I would get a lot out of it. And then once that window is gone, it's not like I couldn't travel again, but I couldn't get that specific life stage young person, happy go lucky, flying by the seat of my pants version of it. And it was also really cheap. It was like $250 to fly to Barcelona. Hostels were $15 a night.

The whole thing just really didn't cost that much. So my kind of early 20's decision was I really want to optimize for like young me's version of fun as hard as possible for like a year. And that's ultimately how I spent basically August 2021 through August 2022, which also kind of goes back to the boss hinge thing. It's not like I was trying to get fired, but like I was much more willing to like flirt with the line a little bit of like if I lost my job for this, it's a funny story. I'm planning on quitting in a couple of months anyway. But yeah, like I made a decision that I'm going to spend a year having as much fun as possible knowing that on the back end of grad school, my career is going to be more important. I won't have the flexibility to do stuff like this. So like the amount of money I would save at my like first job in Atlanta working another year really just wasn't that much versus the amount of fun I would have going and doing crazy stuff over that period and just figuring it out.

And it was now five years later, totally the right decision. Yeah. Yeah, exactly. Your story, it reminds me a lot of mine when I was in my 20s did the same thing like quit my job after a couple of years and spent 27 months. So two years and three months just traveling. I flew to Egypt on a one-way ticket and then just kind of made it up as I went and just lived out of a backpack. I'm curious, what was your favorite country or city or place? Yeah, you know, people ask me that.

And I don't have a universal favorite. I've got favorites for different, like favorites in different categories. Like, favorite beach and actually like favorite quiet beach versus favorite party beach. I've got favorite for meeting locals. I've got favorite for like the place where I would not live, but. well, but temporarily live, live for a while. Within these different categories, there are different favorites. Yeah.

Favorite for meeting locals, Myanmar. Okay. Favorite secluded beach. If you go to Indonesia and you go to, there's like Bali and then there's Lombok and then there's this one other island and to the west of that, there's this island called Flores. So if you go to Flores, on the west coast of Flores, there's this little town called Laban Bajo. And if you take a boat from Laban Bajo, and this is like kind of, kind of, kind of where like Komodo Island is.

If you take a boat from there, there are these small little islands, Sarawa Island and Kanawa Island. They're tiny. There's like 10 huts. There's electricity maybe. There's like a couple of fish and some water that you can eat and drink. And that's it. It's very, very like remote and secluded. And I absolutely loved it.

Spent weeks there just like with a big stack of books and a snorkel. That's awesome. That was definitely favorite for like secluded beach. So yeah. So for all of these various categories, there are different favorite places. Cool. Yeah. Broadening this out for the rest of the audience, you write about a philosophy of how to live your 20s.

And 20s are an interesting time because, you know what? 22, 23, 24, you haven't proven yourself yet. Right. And with that comes the insecurity of not knowing if you have what it takes. a lot of people aren't just working to make a paycheck. They're also kind of working in a sense to prove themselves. As you were traveling or as you were optimizing for freedom and flexibility and adventure, did you grapple with the conflicting thought of, but I haven't proven myself yet? Not really, but for me, there were like a couple of things going on. One, because it was still like 2021 and everybody was working remote and whatever, I think I would have viewed the whole thing. a lot differently if I was like in the office interacting with coworkers, blah, blah, blah. But everything was so isolated that I kind of felt like I was just wasting my time.

Like there was, I don't know how else to put it. There was like no good way to prove myself as like an individual from behind Zoom calls all day, Excel sheets, whatever. Like I kind of felt like it was like a waste of time. Like all the compounding relationships or whatever, I just wasn't getting any of the upside for that. Again, I knew I was going to grad school in a year. So I was kind of like in a different world where I was.

was like had more like I'm an extroverted guy like being in an office environment where like I would have been like around co-workers and there probably would have been more like challenges and tasks I could have taken on and this and that maybe I think about this differently but in in a world where everything's remote and you're doing this and doing that I actually thought the better version of proving myself was just doing something totally crazy and off the wall and different and it's like am I cut out to just like ditch America for a year and go to other countries? forced myself to make friends of new people, that almost felt like it didn't feel like a shirking away from responsibility. It actually felt more like this is a much more interesting challenge to go

after right now and is a better use of my time. I kind of knew that proving myself career stuff would probably come a couple of years after that where in my head it was like when I'm 27, 28, 29, like that's going to be the thing I'm optimizing for. But right now, when I'm 27, I'm going to be much happier that I did all this crazy stuff now versus just maintaining some kind of passive existence for the sake of a moderate paycheck, right? So I take the opposite where like the thing I did was a version of proving myself, just not the typical way people think about hitting certain notches in their career to advance to the next level. Right. That makes sense. Had you already received grad school admission at the time? Yes. So for context on that,

I went to business school at Columbia. That makes us, we share a university. A lot of business schools now do this deferred enrollment offering where if you're a college senior, you can, normally for business school, you work anywhere from like two to eight years and then you apply to grad school and then you get in, you go to business school for two years. 15 or 20 programs now offer deferred enrollment options where you apply your senior year, take the GMAP, the GRE, whatever.

If you get in, you then work two to five years and then go back to school. I got into Columbia through that, and I kind of knew that I was probably going to start in like August 2020 or 2023. Because of that, I had this like mental kind of timeline in my head of everything I do, not that everything that I do pre-business school doesn't matter, but like my career afterward likely won't at all be dependent on what I was doing before versus opportunities I set up while in grad school. So why, I shouldn't actually be optimizing for career. at this point. And that was also somewhat dependent on, like, I knew the companies that would be recruiting out of Columbia Business School were probably better companies than those recruiting out of Mercer University. I love Mercer, played football there, had a blast in undergrad. I wanted to go to New York or California, and that's not like Mercer's not a recruiting hotbed for that.

So, yes, like that also made it easier to kind of set the expectations of, I know in three years I'm going to do this, therefore I have this two and a half year window now to kind of do whatever. Yeah, so you're looking at grad school as an inflection point. Correct. Yeah. There's so many like biographical similarities in our story because I don't know if you know, we have, we have the Atlanta connection. Although you grew up in South Georgia. I just landed there for a while, but my parents live there. I like Atlanta. It's, I live there two and a half years. It's great. It's like there's a non-zero chance I end up back there at some point. Yeah. Yeah. What part did you live in? Buckhead. I was on Lennox Road, like a mile

and a half south of the mall, like a little townhouse with two of my buddies. Oh, nice. Cool. I was in midtown. Nice. Right by Park Tavern, actually. I love Park Tavern. Great spot. So what's interesting to me about seeing grad school as, as that inflection point is society generally expects more of people in their late 20s than in their early 20s. You made the point that all else being equal, if you are 24 and you haven't quote unquote achieved it, anything yet, but you've done some really cool stuff versus if you're like 29 or 30. And only thing you've done is like a decade of cool stuff. Those things are like looked on very differently.

Yeah. I mean, I, the way that I think about it is like the younger you are, the more the people judge you on your potential where like if you're high energy, you have a good story, maybe you don't have the right logos on your resume or whatever, but you just genuinely bring like good energy to the room. And people like that and think you'll work hard. They'll open doors for you. And I even know this in my own life from when I first started blogging online or whatever,

I was 24. And random people were just reaching out to me with like, I would necessarily say job opportunities, but just like kind of wanted to be in my orbit because they thought I was interesting from what I was putting online. That still happens now, but it's increasingly more related to like, I work for venture capital fund or like I have a book coming out. And it's like, okay, I now have these career or professional. related like accolades or just like positions in life that lead to like the doors being open.

And I think there is like a mid to late 20s inflection point where people start judging you more on your results than on your potential. And like downstream of that, your future career and like life opportunities are kind of downstream of the things that you've done where like everything starts compounding. So one, like the direction that you put your 20s somewhat, I don't think it's ever impossible to start over. I'm like very much in the. camp of people have agency and can like pick up and do new stuff whenever they want. But it does become increasingly more difficult and like inertia is very much a thing where you're kind of just a blank slate that can like start fresh, start fresh, start fresh over

and over again in your early to mid-20s. And the ability to do that disappears or like you just mentally feel like you're having to like take a step back to redirect the order you get where like if you have moved up to a certain point in a finance career, then you want to pivot to like tech or whatever. If you're 25, you do banking for two years, you just kind of like jump into a tech job. That's pretty like a lot of people join a startup or do whatever. If you're 35, it's weirder because you're probably like a VP level, whatever in your job. And it's like, all right, does this skill set translate to this other thing?

If it doesn't, you have to kind of take a step down, relearn a lot, move up. And it becomes harder to do that, both from like lifestyle expectations, societal expectations. societal expectations, whatever, because the younger you are, the more that potential waits your opportunities versus when you're older, it's outcomes. Yeah, it just shifts like how easy it is to do a next thing. Right, right. To your point about the, you've got that VP position at the age of 35, it's harder to make lateral moves. Right. You know, you'd have to truly make a career change. You may have to regress. Correct. And that's tough. Right. It's like people, talk about the financial hit of taking a pay cut. But I also think there's a massive ego hit to

the more that your identity is tied to your career. Right. Like you will stay in a thing that you actively don't enjoy because you put some level like personal self-worth and the thing that you're doing. Right. Well, and once you get used to a certain level of autonomy, it's hard to give that up. Often with a regression in career status comes a reduction in in autonomy. Maybe you are more tightly managed, you are more tightly governed. You know, you don't have the, the authority. I guess that's the word I'm searching for. You don't have the authority that you used to. And I think probably the hardest thing is giving up the authority, the level of decision-making power, which would have to happen if you took a regression position. Because I went to grad school in my 30s. For me, it was not an

inflection point, but it was because I already had so much momentum in what I was doing. pre-grad school that I was like, well, obviously, I'm going to continue doing this. So for me, grad school was a sabbatical rather than an inflection into something different. It's funny that I kind of do think grad school literally serves two purposes. Either you need to take a break from your thing before continue to wrap your thing or you read or that's the, like, most people shouldn't go to grad school unless you just want a like call like professionally acceptable sabbatical or like you can have fun but also have more mental bandwidth to explore stuff or you're trying to rerout from like this thing to that thing.

Yeah. Yeah, you're right. It's either a sabbatical or a redirect. So it was a redirect for you and it was just a sabbatical for me. It was a socially acceptable sabbatical. A lot of people these days, people in their 20s spend a lot of time alone in front of screens. And I think this kind of intensified during the pandemic. Yeah. What advice would you have for anyone who's listening who just feels sucked into that. Like they like the notion of adventure, but then on an actual day-to-day level, it's really hard to like stop playing Fortnite.

Yeah. And it's funny because my screen time is probably worse than most people's, both from like I spend a decent amount of time riding on my laptop. And then there's the whole like, you have to put out a certain amount of content on Twitter or LinkedIn or Instagram or whatever. And then I'm like terminally addicted to Twitter. I love Twitter.

I live on it, whatever. But I do think it's pretty important to realize you only have a certain number of hours a day. And for example, I haven't touched a video game in years, but during the pandemic, I was playing a decent amount of Fortnite. Like all my college friends and I were still playing it. But that sucks up, like, a big chunk of that non-work free time versus you almost have to, like, force yourself to, like, get out of the house, go of like social interactions with people. Like living in New York now, it's easier because a lot of my friends, you can just, like, walk to your friend's apartment, whatever. It's different. But like in Atlanta, I had like a basketball league I played in twice a week.

Or it's like very good to have social setups where like you have to interact with people, particularly if you're in a job where you're remote heavy or even if you're in an office, but you're like it's a small team. You're in like a cubicle in front of a screen all day. Like I do think you have to force yourself to have social interactions. Are you talking about like in the like day to day of getting screen break? You're talking about broader like you want to go do something crazy but don't know how to unplug and do it. Well, what I was thinking about was how you've written about apathy.

Sometimes too much screen time can kind of turn into a, you lose a piece of your soul. Like the screen becomes a horrocks to use a Harry Potter analogy. Yeah, yeah, yeah. No, that's a very apt analogy. I mean, the problem of screens, and I wouldn't even say screens as much as like social media specifically and cell phone social media. I don't think screens themselves are the problem. You can't be on your laptop and you're like walking around. Some people are now doing it, like, the meme of, like, people with their laptop open so all their AI agents can keep running.

Like, that is kind of a thing in San Francisco. But when you're not, like, sitting in front of a desk on a laptop, you're not on the screen. But, I mean, if you just look at the subway or, like, look at people waiting in line at Starbucks. Like, everybody's default is if they are, like, by themselves with their own thoughts for more than 30 seconds, impulse is to, like, check phone, scroll Instagram, scroll TikTok. I like to tell myself that scrolling Twitter isn't as bad because it's mainly words instead of short form videos. It's still, for the most part, slop. It's all slop. There's a real problem where people's attention spans are totally fried.

Ability to focus is totally fried. Most stuff that actually gives you some sense of like satisfaction or like self-worth is downstream of like concentrated work on a thing. Accomplishing tasks gives people like such a sense of reward and like positive momentum. is just a thing that matters a lot, I think. And when you have your phone next to you and you're 15 minutes into something and it's difficult and you have to like think it through, whether like you're working on like a really intense project or like say that I'm doing like research on a company we're looking investing at and it just takes hours and hours to get up to speed on some new industry like

the legal system. We're looking at an AI company doing some kind of legal AI thing and there's so much stuff I just don't know about it. It's really easy 20 minutes in and just like look at your phone. Say I'm going to take a two minute break. start scrolling, 20 minutes go by, and then you just completely blow up your train of thought. It's like you're losing your focus. So constant exposure to social media just blows off ability to develop positive momentum and like

getting things done, which leads to a spiral of like you feel like you're falling behind and then you scroll social. It's like people who bingey. Like social media is just another version of that where like you just keep going for that short-term dopamine hit that leaves you feeling like worse after and then you feel like you're falling further behind whatever thing you were going after. And it's just like a doom cycle. And when I'm working, I try to, I have an app called Freedom where I can just block social media online. I have that same app. Yeah. Do you actually use it? So initially, I used freedom to block

Instagram from myself 23 hours a day. And I left 8 p.m. to 9 p.m. open. But of course, I never set like a calendar reminder for that. And so most days what would happen is I would look at the clock and it's like 917. And I'm like, oh, I miss my window today. Then that happened. doffin enough that eventually I just set freedom for like block Insta. I was off Instagram for maybe, I don't know, two, three months. I finally got back on there and I was checking my DMs and like, I saw one from 19 weeks ago. And this woman was like, hey, it was great to meet you tonight. And so that's the problem is like, oh, whoops, here's a potential friend that was trying to follow up with me 19 weeks ago.

I do think it's also uniquely tough if you're like a kind of. content creator where so much of your livelihood is based off of like keeping the content train going online. I do think having the time block of you have like one or two slots per day where you can like check the apps and then you're totally off of them is probably the right way to do it where 30 minutes in the morning, 30 during lunch, 30 in the like early evening and that's it. And it only takes even if you're doing this for living like an hour max of both posting checking engagement and like see if there's any comments or DMs or whatever and and like getting off. The issue is if you just give yourself like unblocked amounts of time,

the doom scroll rabbit hole. These platforms are like built to capture people's attention. They're very good at what they do. Yeah. When you were traveling, did you ever get stuck in like a social media spiral in some beautiful place, but stuck in a social spiral there? I wouldn't say got stuck in a social spiral. I have this weird like, again, my main platform is like trying to grow my newsletter and then like downstream of that kind of like it was mainly Twitter then like I wasn't really posting that much anywhere else I was a little bit obsessed with like making newsletter subscriber account go up where like I would actually refresh like subscriber count too much I was like pretty obsessed with open rate and click through rate and all that which wasn't

healthy either and then I was still probably spending too much time on Twitter but I would say that like I was a little bit neurotic about am I growing same amount of subscribers by week or by month as I used to and like is my Twitter following going up and all this stuff. So it wasn't like an Instagram Reels rabbit hole doom scroll thing, but like there was some level of probably unhealthy attention to detail on Twitter newsletter growth metrics. Right. Well, that sounds healthier because at least that is productive and work related. Right. Right. But it took up way too much mental bandwidth relative to what it should have. Right. We've talked about apathy in the context of screen time and social media. What are some of the other factors?

that play into the apathy or the malaise that afflicts a lot of people in their 20s? I think there's two things. And it's like what I call like the two biggest traps, young people fall into. One of them is apathy, one of them is status. I actually think that they're very, very related in that everybody's seen a version of the status trap where you go to a like competitive school with a lot of other people. There's a lot of wealthy kids there. And then everybody's gunning for the same jobs at the same companies. It's some subset of like finance, big tech, law, whatever. And once you're on that train, everybody's trying to one up everybody else with like finance job, finance job, finance job, finance job, tech job promotion, blah, blah, blah.

Everybody's seen the version of that. Apathy is almost like a consequence or side effect of status obsession where there's a real problem now where like people start feeling hopeless and apathetic about their own circumstances or position in life because they're comparing themselves to others, which is it's a status thing. Like, I don't think my job is as good as like the people I went to college with. Therefore, like, I feel like I'm falling behind. And the issue now is because of social media, you have so much visibility and exposure into other people's lives. But it's like a fun house mirror version where like even if you see what career somebody has, you don't actually know how much money they're making or frankly how much money they're

keeping what their burn rate is. You don't know if they're happy in their personal life. They might be totally miserable. All you really know is maybe what they do for a living, then what version themselves they put online. and everybody's only like nobody's actually putting out their low lights online it's always a highlight real you now have exposure to some percentage of the lives of thousands to millions of people some that you know personally some that you know professionally some that you don't even know

but they look like they're around your age once it was similar school but you think they're doing better than you and then you are looking your own life like i'm only making this much money or like i feel behind other people are advancing their career 30 years ago you kind of only knew how people were doing that were like in your immediate orbit, like in your community, in your job, in your office, whatever. Now you know how 50,000 people are doing. Yeah. It's just a horrible spot to be in.

The two outcomes from that are, I actually think status chasing is the lesser of two evils. While the motivation is unhealthy of like I am trying to catch status of my peers, the outcome is like maybe you do make career progress or whatever. It's just you're probably not going to be happy and you'll be stressed. Apathy is the other version where like you feel. like you're far behind and like can't keep up and it's hard to break that inertia and take action and you feel over time, the longer you delay taking action, you feel further and further behind and more and more hopeless. But both sides that are so downstream of, we're all just playing

these like permanent comparison games now and you can't really, even if it doesn't affect you as much as other people, you're still aware of it. Like I know which people in my network are like, they started a company and sold it or like they're doing really well to hedge fund or whatever. And it's, and some people probably look at me like that, like, oh, it seems like Jack is doing all this and all that super well. And it's, like, I've taught of people making way more money than me that seems to be somewhat envious of like certain parts of my life. And then like, there's a version of me that's like, well, this guy cleared almost a million dollars this year. And everybody is comparing the parts of their life. They just don't really enjoy or appreciate to the parts of other people's lives they deem to be better than them. And I just think it as everybody stressed out. And like apathy is a like very common. manifestation of that stress. Like, I'm just going to doom spiral. Right. When you get so stressed out by the constant comparison that you end up just kind of quiet quitting.

Yeah, you freeze. You just like, I don't know what to do. Therefore, I just stop. Yeah. Right. Right. You have a freeze response. Sometimes I feel a freeze response just from inbound overwhelm.

Yep. There's so many things coming at me that I cannot reasonably manage at all. and either like literal messages, like literal inbound messages, or sometimes it's just like so many tasks and so many things. And I'm the bottleneck in all of it. And when all of this is rushing towards me, sometimes it just gets so overwhelmed that I have a freeze response and do nothing because there's just too much. Yeah. And I hadn't thought of that as apathy. But a freeze response when chronic can become apathy.

Right. Yeah. It's a defense mechanism, really. It's like if you just kind of numb yourself to the thing, it doesn't hurt as much or stress you out as much. And then, yeah, like you're just like totally removed from the game at that point. Right. Yeah. What are some of the best antidotes? I think for most things in life, just feeling like you have positive momentum matters.

Like at rock bottom, simply like getting out of bed, making your bed, going to the gem. That's a way. Just like maintaining level of self-care and life responsibilities is. is a basic step one, but actually like matters a lot when you're spiraling. It's such a cop out to say like don't compare yourself to other people, but being able to focus on a task at work and getting it done, stuff like that just matters. Something that I've realized in my own life is like relative position in life actually is a fleeting feeling of satisfaction.

Like it's the whole hedonic treadmill, blah, blah, blah. Being at any particular level, you're still subject to like comparing yourself to people above, you just reset your baseline expectations of this is where I am now. I'm at a better place in life now that I was three years ago. But on one hand, I also almost feel like more anxiety is too strong of a word, but more sense of urgency to like, I need to do more and more and more. It's like you can see more opportunities as you keep moving up. But for me, the thing that kind of helps alleviate some that stress is just feeling like you're making progress. Writing a book, it was a lot harder than I expected to be. I very much in my mind going into that was like, all right, I've written probably close

to a million words online. A book is a lot less than that. It's basically just 20 blog posts. It's much harder than that. But you get a chapter done. You're happy with it. It feels like progress. Okay. Now we need to do that again. And setting difficult, but very achievable goals and then hitting those just matters. Feeling like your momentum is going in the right direction is so much more important than being at any particular place. It feels good to feel like you're making progress. Other people can kind of detect that. Like if somebody feels like they're on an upswing, you're like energy changes. It's like a perceivable thing by other people in your environment. So you almost just have to set up tasks or goals or quest or whatever you want to call them where you have to strive to hit

thing, but it's doable. And that's also dependent on where you are in life. Like if you're just struggling to get out of bed, that thing might literally be like getting out of bed, making your, just like having your apartment put together and just like functioning normally is a massive improvement from where you were. You can't focus on, I want to be in the C suite of company when you are at rock bottom, but you can put yourself in a better foundational position to like get the next step and the next step. So I think like breaking tasks and goals down into like things you have to put effort into achieve, but are doable is regardless.

this of where you are in life, kind of the only thing that matters. Much of what you've described is the act of becoming. Yeah. I was just talking about this the other night, actually, on a Zoom call. Because somebody was asking the question, and this is a question that a lot of early retirees grapple with, the achievement treadmill. When do you get off the achievement treadmill? And when have you racked up enough achievements?

Yep. Someone asked me that question. And my response was similar to yours. I was, you know, I was like, it's really not about the achievement itself. It's about the person that you have to become in order to be able to do that thing. And because we are always in an act of becoming, human life is dynamic. So we are always becoming every day for better or worse. You know, sometimes we're becoming worse.

But because we are always in an act of becoming, a goal is simply a way to, it's a forcing function that gives direction to what one is becoming. Yep. Yeah. You write about how life is stage-specific. What do you mean by that? Let's say somebody lives 90 years, right? Let's call the median human life.

You stay healthy 90 years. On one hand, you have the same 52 weeks in every year. But what gets missed when you look at like a calendar view of life is that the experiences you would want to get out of like any one of those years or call it like any block of five years is very different. from like any other block like the the things that you will want to do and have the ability to do it call it from like 22 to 27 as much different from like 52 to 57 you're just in a totally different life stage the desires you're going to have the responsibilities that you have the

energy levels that you have the opportunity set that you have is like totally different and I think it's really tough for a 22 year old out of school to be fully cognizant of the fact that I am going to get older and while still being me, the like things that I will want to do, the amount of money that will cost to do, the things that I want to do, like all of this stuff is just going to change a lot as I get older. And because of that, you can like graduate from college at 22 and have all these ideas of things that you want to do, but then commits yourself, you need some level of stability or money saved up or whatever to go do these things. And then 10 years later, you blink and you're like 32,

you're married, you're starting to have kids. And the window of opportunity for a lot of those things shuts. At the same time, a new window of opportunity opens for other things that involve like your spouse, your kids, your community, all that stuff. But if you're not aware of this shifting window of opportunity as you go through different parts of life, it's like really, really easy to just not achieve or do some of the things that you want to do because you didn't realize there was an expiration date on those things. When I was in my early 20s, I wanted to do this whole backpacking trip abroad. I had a blast with it. It was super fun. I was. I'm 29 now.

I still like to travel. I'm going to France in a few weeks for vacation. I'm still very much go do interesting stuff. I have very little desire to do a three-month stint. Like, I love living in New York. I like how my life's set up right now. I just don't want to go to Australia for three months or whatever. But I'm really glad I did do that at 24, where it was the 24-year-old Jack got way

more enjoyment out of an experience than any other older or younger version of myself would have. That was an example of doing the right. thing at the right time for me versus if I try to do that exact same experience later, I could do the exact same trip. I would enjoy it way less, right? Because it was a stage specific thing. And careers are like that. Relationships are like that.

Like every part of life is the amount of enjoyment or like utility you get from a particular thing isn't just dependent on that thing. It's dependent on the version of you and the life stage version of you that's doing that, which I don't think people take that into account enough and they're thinking through like what you want to do with your career, what risk you want to take and when you want to take them. There's so much more to any decision than how much will it cost or how much time will it take. If you aren't thinking through, is this a thing that like I only have a couple of years that I could go after? Therefore, I should do it now. You might miss the window.

Once a window has closed, it's very obvious that it has closed. As you get older, there's always things that maybe you wish you would have done when you were younger and you can't. or if you go do them now, you're just not going to get the same enjoyment that you did. It's like a stereotypical example. But if you're like out at a nightclub and you're 25 and then you see the like group of like 45 year old dudes over there with the table, like maybe they're like having fun, but they kind of look out of place. You can spend so much money to be in the club, but you can't buy back the experience of being the 25 year old in the club. That applies to a lot of stuff. I'm going to challenge you a little on this.

I get how it's stage specific, but I don't necessarily correlate stage with age. And what I'm thinking about are all of the people who in their 30s or 40s or even 50s, either retire early or they take a sabbatical, prolonged sabbatical from work and do something awesome. Yeah. You know, like ride the Trans-Siberian Railway or backpack through South America for six months or get an RV and maybe they've got kids and they're like road schooling. with the kids, like homeschooling, but like turning it into a big field trip. And so when they're doing their chapter on Machu Picchu, they take their kids there. And when they're doing their chapter on the Great Pyramids, they take the kids there. With the right, and of course you need some level of disposable income for that,

but with the right attitude, with a commitment to it, and with adequate disposable income, seems like you could create that stage at any age. I agree with that. But even let's take the like road trip school. example. Two things on that are one, you do need some level of disposable income. It's higher than doing like a solo backpacking trip, whatever. It's not that the window of opportunity to like go have interesting experiences abroad expires, but the window of opportunity to do the like, I'm fresh out of school, hostile hopping experience expires. That's not to say you can't do that then, but there's a

difference between being like 24 and a hostel with a bunch of 22 to 25 year olds and being like 35. Like, your relation to the people around you in that environment changes because the majority of people doing that are in a different, they're like 10 years younger than you or whatever. It's not that it's right or wrong, but it is a totally different thing with just how you relate to the other people around you. That's honestly a big part of it is, like, for example, a lot of people do, I don't know if I would say a lot, but people do retire early. And a lot of people take sabbaticals at some point here or there. one of my concerns about the veneration of the fire movement is that while you can get to a point that you have a lot of freedom to do whatever you want earlier than what would have been a traditional retirement timeline, if most of your peers are still fully in the employment cycle, it can be fun for a year, but at some point you're going to find yourself increasingly alienated from people who are like, if you're 38 and retire and then you're 39, most of your peers are working another 15 years. And they are like starting to like peak on what they're doing with. their careers, while you fully stepped away from the career game, you're going to just find yourself less and less able to relate to people that you, like, it's not that you're going to lose

those friendships, but you're just not in the same game that they're in anymore. It makes it harder to relate where, like, we're social creatures and none of us live in a vacuum. So if you're doing the thing that's totally different from the other people your age, or it's not just age, but you're just broader peer group before that, part of the value of any life experience is the relationships and the connections of the people like doing that thing with you. And even though you have full autonomy over what you're doing, you don't have autonomy over how that relates to other people in your environment. There's like a whole cohort of people that either right out of school or like they've worked for a year or two, do the whole like vagabonding abroad thing, which is cool. And there's

a digital nomad community of all age groups. I'm like well aware. I like hung out with plenty of people in their 30s and 40s in Argentina when I was down there, for example. But it becomes an increasingly like smaller and smaller cohort, the older you get. Like, you traveled for like a couple years in your 20s. I'm sure you saw the same type of thing where like there's a version of that that's very like 20s weighted. And then there's like a different version of that where there's people with more disposable income. Maybe they work 10 or 15 years. And then they're taking a year off going to do different stuff. But it's just different. So it's not that adventure expires. But the version of this is cheap and thrill seeking and I'm trying to do this on the cheapest budget possible and blah, blah, blah. And I'm

hanging out with other people my age, that does go away and gets replaced by like different iterations of that. Right. And you do see with the fire community, one of the dominant conversations that you hear often is that loneliness. In part, that's why there are so many in-person meetups. Yeah. Because it's such a, a rare thing to do that you have to have those in-person experiences, especially for people who don't live in major cities, that can be really hard to find. I mean, a lot of people like to say the work sucks. I would argue, like, Okay, well, what's the alternative? We're not made to just chill permanently either.

Like, it's working toward things is the default state of satisfaction. It's funny, I just started reading, I think it's called The Strenuous Life by Theodore Roosevelt. It's a collection of speeches and essays he has. The recurring trend is basically, and it's funny, these essays are, they were from year 1900, approximately. But he has this whole thing about how people were created to, like, go after difficult things. peace is a byproduct of like hard work or of war or of conflicts and like overcoming stuff versus if you're just optimizing for like a life even if you're like he talks about people who are super high at worth whether they're rich because of like work they did or that their family did that wealth

is a byproduct of doing the work and even if you have reached that point it's still your responsibility to contribute to society through like writing or art or like scientific discovery we should just always be doing things and having positive momentum. And that's where the only sense of true satisfaction, life satisfaction comes from, not just enjoying this consumer surplus or whatever, right? With a fire move it, it's like, it is a very good thing to have enough money where you don't have to worry about money anymore, but you still need to work on stuff. Like, everybody needs to work on stuff. I just really disagree with the idea of the whole point of making money is you get to a point where you don't need to make money anymore. I think obviously financial

responsibility matters. Having money is much better than not having money. But I don't think the end outcome of life is just gets to the point that you can opt out of the labor force. Yeah. Anecdotally, at least, what I often see with the fire movement is they're very highly educated, very driven, very ambitious, and they often are in some type of a work environment that they find constraining. Yep. Reaching a particular net worth allows them to get rid of that constraint. Yep.

And often, at least anecdotally, often what tends to happen is there might be a short period of three months or six months where it's like, great, I'm free, let's go travel. Then their attention turns to, all right, with those constraints off and with cash flow not being an urgent need, what then do I want to do? Yeah. It is very nice to have that mental bandwidth to take a few months and just think things through that you just don't get when you're working full time, especially if you like in like third. I don't have any kids, but like working full time plus kids. There's like zero room for I need to take three months and just figure out what to do next. The biggest benefit of achieving fire is you just have flexibility to like take a pause and figure out next thing. You just don't want the pause to become like the default. state of like what you're doing. Yeah. And I think what's valuable about your message is for people who are in their 20s is such a reminder that like you don't want to be 24 or 25 and so committed to this idea

of what your life will be like 20 years in the future that there's that expression, plan for the future, don't live in it. Right. And I think what can often happen, especially among people who self-select as people who listen to personal finance podcasts, We're often so focused on planning for the future that that can sometimes translate to living in the future, over-living in the future. Yeah, it's a very bad trade-off to continually sacrifice the present for, like, a hypothetical future. A lot of people live in the past and ruminate too much, which is not great either. Everybody knows that staying stuck in the past is bad. It is much easier to fall in the trap of living in the future because you tell yourself you're being prudent and frugal and this and that.

in reality, you're just, life is only in the present. You know, wisdom is holding two seemingly contradictory ideas simultaneously. We simultaneously have to hold the value of, I mean, I hate the phrase delayed gratification. I've always hated that phrase because I believe that if you're doing it right, the act of saving and investing itself should be inherently gratifying, which is why I hate the phrase delayed gratification, but in any regard, we live in a society where like delayed gratification, deferred rewards, those things are considered prudent and are considered wise. And it's all about working hard today so you can reap the benefits tomorrow. And that has to be held

in tandem with also living in the present. And that can be very hard to do, particularly when you're in a situation, you're in a job that you hate. Actually, yeah, what advice would you give to anybody who's listening to this who's like in a golden handcuff situation? I think it's just you have to be very honest with yourself where when golden handcuffs are actually a pretty good spot to be in all things considered. If you're employed in making a lot of money and your biggest issue is like you want to do something else, but don't know if you can give up the paycheck. I guess the alternative is like not making a lot of money.

Like there's I don't think that like golden handcuffs are it's such a kind of ridiculous label to me because what you're basically saying is like, I'm making too much money to go do something else. If that's true, that constraint is some mix of like you're spending too much money or it's kind of a self-imposed restriction on you just refuse to either take the status hit of leaving the thing or you've put yourself in an incredibly expensive lifestyle where like if you're living in Manhattan, your kids are private school in Manhattan, this and that. Yeah, that's very expensive in golden handcuffs are a real thing. the alternative is like you move somewhere else.

You can make the changes to get out of the golden handcuffs. It's just a matter of being honest with yourself. You're either making the choice that the more expensive lifestyle is worth the job that I'm increasingly growing tired of. Or I want to do other stuff, but to be able to do that comfortably, I might have to like make radical lifestyle changes. You still get a pick, right? Like golden handcuffs are a like lifestyle specific thing where there are changes you can make. or those don't exist anymore, you just have to be comfortable making those changes. I guess my advice is to be honest with yourself.

Do you want to make this change enough that you're willing to make lifestyle changes to make it affordable? Because the reality is very few people are in a spot where they can leave the high-paying job and still maintain the high-cost lifestyle unless they have sold a company. Maybe they sold their company to a big company. They made a lot of money in that. They're now working for that big company and still have high pay. well, if they made $20 million and they sold their company, like, yeah, you can take your foot off

the gas for a little bit and do other stuff. If you're a high paid salary employee at a bank or a tech company or whatever, and you want to maintain the like Manhattan, Palo Alto, whatever lifestyle, okay, like to be able to change the lifestyle how you want, you might have to think about this is the right geography to live in, whatever. It's just a matter of being honest with yourself. Do you think that also applies to other types of of golden handcuffed scenarios that aren't specifically a job. So, for example, there are a lot of people right now who they're living in a home that they bought in 2020 and they locked in a 2.9% mortgage and they don't want to live there anymore. Maybe they don't even want to live in that

city or state anymore, but they feel golden handcuffed in. The other example that comes to mind, I know a few couples that probably should break up, but then they would lose 50% of their assets. I mean, I don't think I'm in a spot to give, like, marriage or divorce advice as a unmarried 29-year-old. I've never bought a home either, but on the home thing, it's like, yeah, that's a thing. And if you sell your home and then go buy a new home, your mortgage rate's going to be higher and that home's probably going to be like, it's definitely going to be more expensive than whatever you paid in 2020. The flip side is, like, you could sell a home and go rent, you're going to be paying rent and you're not going to build equity in a home. But if you can

sell your home for like $1.5 million, and then you're paying $7,000 a month in rent for like, a nice home after that. I don't know. There's always another thing you can do. It's just, that's kind of the trade, right? There's no perfect fix where I feel stuck in this home and I think we should downsize homes. But if I sell this, I'm going to buy another home at a higher interest rate. You could sell it and then rent and see if rates keep going up and then prices drop or maybe mortgage rates dropping. Nobody actually knows it's going to happen with interest rates or home prices or whatever. I don't think you should make a decision on what to do with a home you own based off of a hopeful forecast on where prices or mortgage rates are going to go in the future.

You either stay or you sell it and you move, but it's the same thing as anything else. It's just a matter of you just have to have a very clear-eyed, transparent view of this is the reality of the environment right now. Therefore, these are the choices I can make. Same thing with relationships. I mean, I've never been married. So therefore, I've never lost assets through a divorce. I have been in the spot of like you're dating someone. You thought at one point you were going to marry them. And then you're sitting there like, I don't know if this is it or not. The longer you delay having a very tough conversation, it actually only gets worse.

Like you're just setting the whole thing we talked about earlier about living in the future. You're actually like kicking future you in the ass by like putting off a conversation for six months or a year or two years. I have multiple friends now who started dating someone in college or right out of school. And then, I don't know, like you, you date two or three years. You probably have a pretty good idea at this point as working adults if you think you're going to marry this person. And then you see people getting like six or seven year relationships. And then finally somebody breaks up with somebody.

If you started dating at 22 and you broke up at 24, you don't really ruin anybody's life. People have their entire future ahead of them. You didn't waste someone's time. You just figured out it didn't work. But if you kind of knew two years in, this probably isn't it. And you just kept kicking the kids. hand down the road because nothing was quite wrong, but you don't think you're going to get the conviction to, like, get out on one knee and propose. Then you're 28 or 29. I don't think breaking

up after a year or two waste someone's time, but like if you break up after seven years, when you kind of knew after two years, it probably wasn't it. That kind of wasted two people's 20s when they could have been dating other people. No problems in the onset are big problems, but refusing to address a certain problem until X number of years goes by, then becomes a big problem. That's like relationships. It's if you think you're in the wrong career path. If you do the wrong thing for two years and you change jobs, fine. Everybody does that. If you knew two years in that you should have changed careers and just didn't do the work to do that up front, it becomes exponentially more difficult seven years down the road. The simple solution of most of these problems is

just address the thing sooner rather than later versus letting it metastasize. There are kind of two things that I'm hearing from you. One is that problems get bigger the longer you delay. The second thing I'm hearing is don't let the tail wag the dog. Right. Because so much of the time, people, especially people who are very financially savvy, they will make the decision that maths out on paper. Yep. Even if it's not what they want. Yep. And it seems like a major theme of what you're talking about is let the heart lead and then the mind execute. Yeah. It's like if you do want to make the decision that maps out on paper. Cool. Just know that you're making that decision. Like I actually, I don't know, I do think that there can be a misconception of,

it's easier to romanticize the idea of money doesn't matter, live, laugh, love, go chase your dreams. I don't actually think that's good advice typically. I think it can be in like specific windows. Like if you want to take a career sabbatical to go do something, yeah, you should do that. But I have a plan. At the same time, I actually see nothing wrong with spending a few years where, like you tolerate a really rough lifestyle and work-life balance to make a ton of money. Okay, investment banking is kind of a grind, but it's also the highest-paying job. The median person can get right out of undergrad if they play their cards right. Making $200,000, $23 or 24 is pretty crazy.

And your social life is going to be worse than some of your friends. But if you know going in, I'm doing this to get the right prestige job and make a lot of money along the way, I think that's a totally valid decision to do. you just should know what trade you're making you you can't get upset about the circumstances of a decision where like you should have known the consequences and the tradeoffs going it just like if you pursue the like more frivolous have fun whatever thing you can't be mad the people who made another choice are making more money than you and i think envy is such a toxic trait that's also like so universal and pervasive because everybody wants what they can't

have but like just having honesty with yourself of like i made this choice there for for like this outcome shouldn't surprise me. I think more people should just be honest with themselves about that. Yeah. Yeah. And envy is funny because people often, they envy the result, but not the sacrifice of that took to get there. Right. Like, why do you envy the life? I don't know. Like, it's the whole, oh, look at a list of billionaires. Eleven divorces for the seven wealthiest people in the world. Shout out Mark Zuckerberg, the only like mega billionaire who's actually so married to like his college sweetheart. What I trade spots of Elon Musk? Probably not. He seems like he doesn't really seem like he's having fun. He seems incredibly stressed out. Like, would I like to have a

trillion dollars? I mean, like, probably. That would be cool. But it doesn't seem like he's happy. He's successful, but he seems stressed. You just have to be really honest with yourself about what the cost of the thing is. We had a former president of Tesla as one of our guests. And he described a moment where Elon was having a pretty significant like mental health. crisis. And, you know, he talked about how, like, Elon didn't want to show up for this earnings call and was laying on the floor of the conference room with all of the lights out. Yeah. Just having an absolute breakdown. And this guy, John McNeil, laid down on the floor of a dark conference room with all of the lights out and talked to him long enough that eventually

they both got up off the floor and made it to the call. But those mental health crises can happen at any net worth level. Yeah. I don't know what the number is. There's probably a sweet spot of net worth where like if you go above it, stress only reaccelerates. And if you go below it, stress accelerates,

the level that your home is paid off and you have flexibility. You can quit job if you need to and you can cover emergency medical situations and you can just do what you want. But not at the level of like you feel like there's like whole companies dependent on you or you're just in this. I don't know. There's a level between like, being broke and being Elon Musk that's much better than both of them. And I don't know where

that it's probably aged, depending on where the like net worth tapers off and both ends on life satisfaction. I would much rather have $10 million than a trillion dollars based off of the like what it would take to get to either of those levels. Yeah. This reminds me of Nick Majuli's levels of wealth where he talks about the level between one million to 10 million. That's the sweet spot. And then once you go above 10 million, like, The combination of obsession plus luck plus time that it takes to get to that. And then you find yourself in like management mode. Like how do I allocate my money?

How do I set up my estate? How do I minimize taxes? Like you hit a level of where it's probably not just like index funds and maybe some bonds or whatever and chilling. Like there's a whole. There's just complexity increases. There's a guy John Arnold who's like one of my favorite Twitter follows. He was one of the most successful. traders of all time. And he now has his own investment group, does a lot of philanthropic stuff.

He put out a tweet that was pretty interesting. He's worth probably a billionaire, if not a billionaire, like hundreds of millions of dollars and just discussing how complex, like his own family wealth management is now with where do they allocate money into like private investments or fund managers or real estate or does he still trade some of his own money and this and that? And it's just the amount of things you have to think about when you have that much money, it almost like a family office kind of becomes a full-time job. Good problem to have. I would love to be in a position where I'd have that problem, but those aren't problems that you have with $5 million. They are with $500. Speaking of trading, you rapidly made 400, this is a hard pivot. It's a great pivot. Yeah. You rapidly made $400,000 trading spaks. Correct. And then lost it all. Yeah, I didn't lose it all. I didn't lose it all. And this is actually probably the worst financial advice anybody's ever going to. to give on your show, but I don't recommend trading. Steve, can we have an alarm sound of like not

financial advice? This is the opposite of financial advice. If you are going to actively speculate in the market, I do think it actually makes sense to do it in your Roth IRA rather than in a taxable account because one, if you do manage to make a lot of money doing it, you want to go taxes on it. And two, your accountant won't have to look at you. Like, dude, why do you place 700 trades this year to make like $200 or whatever? I started working right with the pandemic hit. I graduated college December 2019, start working February 2020, and I was in the office for a week. I distinctly remember I had like $10,000 to my name. I put it all in a Robin Hood account.

I bought put options on the S&P. Basically, you make money if market goes down. And I made like $20,000 in a week. And I thought I was like the next Michael Burry. I was just like the man. I bought more put options the day the market bought it started going back up. And I round-trip $10,000 to $30,000 and $10,000 in two weeks. almost threw up. I was like I was I was like a broke 22 or 23 year old. After that I was like I'm not going to trade stocks again. I put I think Roth contributions are $7,000 now but at that point there's $6,000 put in a Roth TD Ameritrade. I put in like the QQQ and the S&P and wasn't going to touch it again. And then one of my buddies texts me and he's like do you know what a SPAC is? And I say I have no idea what a SPAC is. Tell me about it. He said well I don't either. But if you buy this thing called Desert Eagle.

acquisition company, in two months, it'll turn into Draft King's stock. And I was like, that makes no sense. So I look it up. He was right. Like basically a SPAC is just a, it's like a shell company, a blank check company that's publicly traded. You can buy shares in it just like it's Apple or Tesla or whatever. But it's called something acquisition company. These companies raise a bunch of money from investors. They go find a private company to take public. They give them that money in exchange for like 10% or 20% of the company. And then, whole thing merges and then you have a publicly traded, in this case, draft kings. Spacks are pretty interesting because if you buy the SPAC when it's publicly traded

and you don't like the deal, you can redeem your shares for cash before it closes. So basically, if a SPAC is trading at like $10 and there's $10 per share, like in its bank account, then you can just like get your money. You've got full liquidity. Even if on paper it crashed, like a lot of these crashed 10 or 15% in 2020 with the market crash, like there was actually free money in buying them because the net asset value that you could redeem out was $10 a share. Spacks were also a total bubble in 2020 and 2021, like a lot of other stuff because it was like COVID and everybody was trading and whatever. I basically figured

out that a lot of these specs were a total bubble and that because of the redemption clause, if you buy really close to 10 and then they go up to 15 or 20, you basically risk anywhere from one to five percent to make, if it's a literal meme stock, 100 or 200 percent. So I just kept parlaying over and over and over again, buying SPACs really close to $10 and then selling them as they started catching heat basically on Twitter or like Jim Kramer would talk about them or whatever. And yeah, I turned six grand and a $400,000 in like nine months. And it was like pretty close to risk free just because of the redoubt. Like I was tactical about what I bought. The issue was like anything else, they became a bubble, then everybody raised a SPAC.

There wasn't enough money to go around, and they just stopped going up. So I would buy one, and then it wouldn't move. I hadn't realized at the time, but I was kind of addicted to the whole making more than my salary at a week because I bought the right SPAC is actually like a pretty intoxicating feeling. I was like, oh, I could probably just trade regular stocks. So I bought like a really speculative buy now, pay later company and like put my entire portfolio in it. I thought they were undervalued compared to other companies.

I was right, but it turns out that even if you are right on if they're undervalued, if the market thinks it should be even more undervalued, it can tank from there. And I lost like $160,000 in a day on an earnings report that went poorly. I basically lost like $200,000 from like top to bottom in a period of about a month. And I was like, okay, well, I'm not going to trade. The actually smartest financial decision I ever made was looking at it like, I'm not going to trade stocks anymore. I still have a decent chunk of tax free money in a retirement account. now, we should probably just let that compound. I've still bought a stock here or there,

but I'm certainly not going to say it was fun. It was actually entirely stressful, but I certainly learned a lot about both my own psychology and investor psychology and just like how markets work. Nice. So in some ways, there might be a glimmer of financial advice here, which is the cautionary tale around trading. Well, it's like the cautionary tale is if you make a lot of money doing one thing and it worked and then that thing stops working, and you try to do another thing, it's probably not going to work. Like the whole like, oh, I had an edge here. Therefore, the ability to make money trading stocks actually doesn't just apply universally across all things you can buy and sell.

So V1 is like, don't trade at all. V2 is if you ignore V1 and you do trade and you make a lot of money doing a specific thing, if that thing stops working, you should just like throw out an index fund. And then V3 is, again, you probably just shouldn't be trading to begin with. But if you do, I guess, do it in your Roth IRA. I don't know. I don't know if I should tell people that or not, but like it kind of worked for me, ish. I'm also probably the only person who made money buying SPACs, considering pretty much the stock charts for all of them is just like, like, in the last five years.

Yeah. I don't know anyone else who made money in SPACs, which is why it makes for such a unique story. It was a weird year. Yeah. Did you buy a portion of the Constitution? That was another thing. No, one of my friends did. So, again, talking about weird things happening in 2020 and 2021, there were like 12 different bubbles happening at the same time.

Spacks were certainly one of them. Another one was NFTs. They were non-fungible tokens. You buy a picture of a thing that picture serves as a store of value. Again, this was like the stupidest thing of all time. People were paying $2 million for a picture of a rock. the the ETH rocks. I was like,

or the whole, if you remember the, the, um, the board ape yacht club where people were buying pictures of monkeys for like hundreds of thousands of dollars. Yeah.

Yeah. I remember that. Incredibly stupid bubble. When I was bopping around Europe, I mean, Copenhagen at this Irish pub with two of my buddies who'd flown out a visit. And we get this call from our friend, Austin.

He's telling us, he worked like, wealth management too, like very normal job in Atlanta. He was like, do you guys want to buy the Constitution? I just think he's like, like drunk making something up whatever and I was like dude what are you talking about he's trying

to explain it to me and I just said just tell me about this tomorrow like I don't want to hear this right now so he says to me an email with a super long there's seven copies of the constitution that are privately owned one of them the guy who owned it died and his family trust is putting it for auction Sutherbees is running the auction and they expect it to fetch like a $15 million bid basically he and some other guys created a they call it Constitution Dow or decentralized autonomous organization where a Dow is basically just a group chat with a bank account. There's all this weird lingo and verbiage of like, oh, we have these governance rights. No, no, no. It's like you make a WhatsApp or like I messaged group chat and they have a

shared Chase account and everybody just puts in money and now there's, in this case, there raised $42 million of people in the group chat. That's a great description, a group chat with a bank account. Yeah, it's crazy. He and a few other people flew to New York for the auction and they bid $42 million for the Constitution. What they were going to do is, like, they'd raised all this money where if you put money in, you got a certain number of Constitution tokens, basically. And again, they were, like, actually kind of worthless, but the idea was whatever proportion of tokens you earned gave you, like, voting rights on what to do with the Constitution. And they were going to like, they were going to, like, put it in some museum or whatever, how to apply this is a

constitution down. Again, 2021 was an incredibly stupid year. What a weird time. How did we all live through that? And it was just like a totally normal thing. So they go up there. They made the bid. Hilariously, they get outbid by Ken Griffin. Oh, the Citadel guy. Citadel securities.

He was already like, this is right around the time that the whole game stop fiasco happened. I actually think Ken Griffin did nothing wrong in that. There's the whole popular narrative. He's manipulating markets. People don't understand T plus two, stock settlement, whatever. But Ken Griffin was like a like known kind of villain figure in the stock trading internet, whatever.

The problem with this Constitution Dow was because they had like a public ledger of how much money they raised, somebody who had a lot of money could just come in and like outbid them by a dollar. And they would just win. It's like there's no way to. It's like playing poker where like your cards are face up and like everybody else can see them beside if they want to fold or double down. So he just outbid them by like a million dollars because he knew they didn't have a million dollars. And if they were to raise more, he would have just raised another dollar. And getting outbid by a billionaire who then got infamous for the whole GameStop thing is hilarious. That is literally what happened.

And Ken Griffin now owns that copy of the Constitution. I have a few Constitution DAL tokens, and then I ended up selling them. And, like, the transaction fees I'm making them cost about half as much of the money put in. So, like, I think I lost, like, $500 or whatever. After that whole thing ended, pretty much everybody just sold or redeemed or burned their tokens where there weren't that many left. And the tokens, for no reason, just turned into a meme stock. And, like, a few people made several hundred thousand dollars, just,

because like the tokens ran up and they still owned stuff. It was like, again, 2021 was proof to me that the efficient market hypothesis doesn't exist because like people are just throwing money at stuff. And that was just one example of a few people probably made a lot of money and a ton of people lost a ton of money. Yeah. 2020 and 2021, especially with the benefit of hindsight. It's like such an interesting social experiment in what happens when everyone is just stuck at

home in front of their computer with nothing to do. and then there's a bunch of liquidity injected into the system. Yep. Yeah. And it's that. Yes. Yeah. Everything that you've just described is that's the outcome.

Yep. Any takeaways that people, I actually want two separate buckets of takeaways, one for people in their 20s and at the risk of asking two questions at the same time. We'll start with takeaways for people who are currently in their 20s. And then any takeaways you have for people, let's say in their 40s or 50s who are like, my 20s are a distant memory, but how do I take some of the wisdom of that era and how do I apply it to my life now? So we'll start with takeaways for people who are currently in their 20s. I think the biggest two things for people in their 20s are one, you should just be incredibly optimistic. Like there's so much doom or porn out there about AI is going to take all the jobs or we don't know what's going to happen or like the economy is awful.

the world's going to shit. There's actually basically never been a better time to be alive just from a like the level of call it consumer surplus we have of technologies on so much cool stuff that our standard of living is so good. And on the whole AI thing, I just think artificial intelligence is kind of democratized the ability to build and do really interesting stuff quickly where there's like never been a better time to be early in your career because so much stuff is changing. just opening opportunities everywhere. So there's like a lot of uncertainty in what does a job

look like or like the correct paths to go after 10, 15, 20 years ago. They don't really exist. Like it's true that pattern matching might not work as well as it did 10 years ago. But there's just so many opportunities. I think those are only going to keep going that the first piece of advice is be optimistic. And the second piece is it's so okay to like not know what you want to do at 22 or 23, even though it feels like a lot of your peers know exactly what they're doing. You're falling behind and blah, blah, blah. Like, it's okay to, like, experiment with two or three or four different things. It's way better to spend your 20s trying a lot of different stuff and then figuring out

where, if you want to call it your zone of genius or like what overlapping interest you have that you find yourself to be good at. It's okay if you don't find those until you're five or 10 years in versus the one thing that you shouldn't do is like commit to a certain path out of fear. or scarcity mindset and doubling and tripling down on that, despite your internal compass saying, this is not what I should be doing. I should be doing something else. Again, there's never been a time to be like a curious generalist.

And I think that it's easy to fall in the trap of, I don't know what to do, so I'm going to panic. Like, there's just so many opportunities out there. I think that still applies to like anybody regardless of age. I think it is easier to restart and try different stuff now just because of 10 years ago. if you didn't know how to code, there were a lot of limitations on what you can do with a computer. You can build really interesting stuff. Everybody has their own set of life experiences. And there's just so many ways to do interesting stuff with your individual experience and expertise now that whether you're 25 or like 55, there's just a ton of opportunities out there.

But I do think the through line of my book about life being very stage specific is just being honest with yourself about if you are 25, like are there things you want to do now that like you won't be able to do later. go do those. That exact same phenomenon exists, whether you're 25, 35, 35, 45, 55, 65, there's a certain window of opportunities that are just very, very pressing and in the now. And regardless of what stage of life you're in, you should be honest with yourself about, this is where I am, this is what's going on around me. Like, these are the things that matter to me now. And these are those things that, like, I probably need to take action on in the next year or two to, like, make the most out of them. And these are some of the things that might be more of a lifelong pursuit and then kind of stack rank those and go after them. I know you mentioned earlier,

like the whole information overload of feeling that there's so much inbound, not just from messages, like, so much information, so many things you might want to do, whatever. My kind of, I call it filtering mechanism for like what are the right things to go after are what are the things that I consider to be fun. I think your internal barometer of fun is like a very useful, it's a very useful tool for figuring out what are the right things worth pursuing, where when I say life is stage specific, I think having a sense of fun or enjoyment around a particular thing helps reveal to you which things are the things you're supposed to be going after in that stage of life. Where, example, if you're 24, you want to go backpack Europe and you do it and

you're having a blast, it was probably the right move. If I did the same thing now, I would probably actually be somewhat stressed about like, oh, like, will I be able to get back on career path after that or this or that. That same experience, I would probably find more stressful than enjoyable. It's probably the wrong thing to be doing at that time. Right. Like having this sense of just fun and satisfaction and what you're doing with your life, I think is a very, very, very strong signal that you're doing the right thing. And if you're lacking that, you should probably do a bit of soul searching on like, what things can I do now that would bring out that feeling. Right. And that goes back to letting the heart lead and then the mind execute.

Yep. Well, thank you for spending this time with us. Where can people find you if they'd like to learn more? Look up Jack Raines on basically any social media platform. I have a cowboy hat on and my profile picture on everything, so it's pretty easy to recognize Twitter, LinkedIn, Instagram, substack. My substack, youngmoney.com. I write a weekly email newsletter. And then most importantly, pre-order by my book, Young Money by Jack Raines. It's on Amazon, Barnes & Noble. You can go to jackrains.com.com. At the time of us, recording this. I'm recording the audio book next week. So there's going to be an audio book. So if you like listening to me here, you can get that. If you hate the sound of my voice, get me an e-book or a

physical book. But yeah, get the book. Hopefully you like it. That is Jack Raines, the author of Young Money. Thank you so much for tuning in. If you enjoyed today's episode, please download our free, it's like a workbook on how to think through your money at afford anything.com slash f-I-I-R-E. That's afford anything.com slash FIIRE. And we walk you through financial psychology, increasing your income, investing, real estate, and entrepreneurship. And it's a space where we walk you through how to think through the way that you want to approach those.

So on the topic of having a philosophy of money, download this, it's completely free. Affordanything.com slash F-I-I-R-E. Thank you again to Jack Raines. His book is Young Money. Check it out. I've read it cover-to-cover. It's fantastic. It reminded me a lot of the.

world travel that I did in my 20s and how unique that time in your life is. So I highly encourage you to check it out. Give a copy of the book to anyone you know who's in their 20s. And if you are in your 20s, check it out for yourselves. Thanks again for tuning in and for being an afforder. My name is Paula Pan. This is the Afford Anything podcast and I'll meet you in the next episode.