"Don't Follow Your Passion!" VC Investor Jack Raines on Getting Rich in Your 20s

Satire as a viral content strategy works so well, and I love it. I'm very anti 'pursue your passion.' I think it's fine to do when you're really young and dumb.

It's actually worse than that.

I am. Yep.

There's so many really smart people building tech companies that like you just don't know about yet because there's nothing online about them.

that's like literally my job. [music] So, I try to be good at it.

Let's go, Matt. Thanks for having me.

That's right. It's an interesting title because when I was young, I had no money.

I've got like, you know, the subtitle is 'A Field Guide to Wealth and Purpose in Your 20s.' I wouldn't call it a typical personal finance book. It's also not a rap label. Lil Wayne, I'm hoping he doesn't sue me for trying to steal his company name with Young Money. Um, the book is really about like thinking about opportunity cost, and like money plays a role in that, right? Like I consider opportunity costs broadly how you spend your time in different sections of your life, and money obviously plays a role in that. You have to spend money on things to stay alive, pay for experiences, whatever. But it's really thinking about like, all right, you have a finite amount of time to be alive, and within that you have a very finite amount of time to be young and in your 20s, when, to your point, you're probably broke or at least at a lower income and net worth than you will be later. So like, how do you make the most out of the opportunities of this window of time before it's gone, while still setting yourself up to transition, you know, in your late 20s and your 30s and so on? So it's really a book on opportunity cost, and any stuff related to money is framed within that lens.

Well, the worst part of it too is like — I mean, I read up on your background, listened to some of your stuff before this. So like, I'm very in on the trades are kind of back. I also think there's a whole subset of jobs that are considered like low status that are actually like probably high income. Like I would argue going into tech sales instead of like trying to carve it out in private equity is like probably a better bet for some people. That's a whole other thing. But on the figuring your life out at 18, there's also always this subset of people where when you go to college who seem like they knew how the game worked a few years before you did, depending on like where they grew up, where they went to high school, what school they go to. When you're young and you're dumb and you're kind of clueless, it's like it can be really intimidating to see people who feel like they're on a fast track that like you missed the boat on, and it just kind of becomes a status game. Should I be trying to do the thing that these people who seem to know what they're doing are doing? And it's just like it's really easy to kind of architect your life direction based off of like pattern matching on other people, particularly when like you probably just are pretty insecure when you're like 18, 19, 20, 21, right? Like it's a massive problem, particularly with internet and social media. Like we just have too much exposure to like details about other people's lives. And when you aren't like a fully formed person yet, that's just really problematic.

So my take on life construction is that on one hand, like I'm very motivated to make a lot of money, be successful. Like I do not want to be in my 40s and feel like I'm poor, right? Like that was never — I'm in my — take $20. That was something I wanted. But I was also really cognizant at like 23 or 24 that I was only going to be young for a little while. And there's like a lot of dumb fun stuff that you can do when you're young and get away with that like you either aren't going to want to do when you're older, you aren't going to enjoy doing when you're older, or you just won't have the opportunity to because life responsibilities and complexity and all that. So, to your point of like, you know, kind of practicing what I preach, a thing that I always thought would be really cool when I was younger — I love studying abroad. My grandma takes like every grandkid on a trip when they were a kid, like anywhere in the world. And when I was 11, we went to Tanzania on a safari, which in hindsight, it's like crazy for a late-60s woman to take her 11-year-old grandson to Tanzania, but we had a blast. And like I was always — I had really romanticized this idea of like, it'd be fun to do one of those really cheap, like staying in hostels, sleeping on buses, kind of vagabonding trip around the world, because I knew when I was older, like I still like to travel, but it's like, all right, hopefully it's a business trip or the hotel is comped or like I'm actually staying somewhere nice. And I was like a couple years out of college, I realized I have this really short window for what's the crazy fun thing I want to do now that I can't do later that also just won't cost all that much. And that was that. And my kind of take on it was I had a couple things going for me. I'd saved up a little bit of money in my first job. I had gotten into a good graduate school, and I knew I was going to go to business school at Columbia like a year or two later. So, I kind of figured that, all right, any extra money I make now is just going to kind of pale in comparison to what my career turns into after business school. And I was pretty set on like my mid to late 20s to early 30s, like ideally I put myself in a position where my career goes like this. So for this next year before I get to kind of that stage, like what's the most fun, interesting way to spend my time? And for me it was like everybody has like stuff they want to do when they're young. My version of this was like I kind of want to screw off and go backpack the world and just like write about the whole thing. It was a very specific thing. I literally just wanted to have a thrill-seeking trip, and I did it also knowing there was an end date. You know, I think the two traps you can fall into are having things you want to do at a particular period in life and just pushing them off indefinitely until you never do them, or chasing the thing without thinking through what the exit plan and the off-ramp is, and then like kind of getting stuck in a cycle of this is really fun and exciting, and then how do I actually get my life back on track? And for me, I had grad school, career stuff would come after grad school, and it's like, all right, like let's take a shot and do something crazy and then, you know, get back on the path, so to speak, a year later. So on like how did I actually go do the thing I wanted to do? I kind of set up the exit ramp from that before I started it. So, it was almost like a trip like that is much more fun when you know that it has an end date and you can really lean into getting the most out of it knowing that like this is a finite thing, but let's go like maximize for fun. And that's exactly how I treated it.

Well, I mean, it's [clears throat] it's like anything else, just like being intentional and like thinking through how you want to do things is more important than whatever the thing is, right? Like as long as you've done the work of like, this is what I want to do, this is why I want to do it, and like this is the time frame in which I will do the thing, whether that's like you want to go start your own business, all right, like have benchmarks that you should hit where if it's not working after six months, a year, two years, you go back and get a job, right? Like you can take like anything that would be considered risky, whether like new job, entrepreneurship, like leaving your job, whatever that thing is, it's a deviation from what you're doing now. Just having your like on-ramp, off-ramp, time frame, and like burn rate very clearly established going into it makes it much easier to just lean into the thing because you've already thought about the downside case, right?

So, it's funny. Do you know who Tim Ferriss is? The Four-Hour Workweek guy. So I've read a lot of his blog posts and a couple of his books. He actually had this whole thing where he was burned out from like entrepreneurship, working like 80 hours a week, and tried to like architect his life where like basically could he hire himself out of a job, do it remotely, and like could he get his company to the point that it kind of runs itself. And like most entrepreneurs at first, he was like super hands-on and everything and thought the whole thing would fall apart. And then he just realized he needed a sabbatical, and he went to Argentina for several months, and he brought two books with him. And one of those books was Vagabonding by Rolf Potts. So, I thought it was funny like reading one of his blog posts about that, and then 10, 15 years later I did the same thing. But Vagabonding, or the author Rolf Potts, he was like a longtime travel journalist, wrote for National Geographic and a lot of similar publications, and just had like a really cool life, or like super successful journalist. Vagabonding sold hundreds of thousands of copies. Like he's just a really interesting guy. But one of his life philosophies was or is that it's stupid to just like push off like fun, travel, whatever, until the end of your life. And it's actually a much better way to live that every few years you have like a mini-retirement or sabbatical. Like maybe you do one in your mid to late 20s, you do another one in your mid-30s, and you make money, save money, take a break, do the thing, and then come back. And the entire book is a mixture of like philosophy on like why it's much more important to like stagger these different like fun life experiences throughout your life rather than backloading, because there's certain trips you can take in your 20s or 30s or 40s that you can't take in other periods. And he was also really pragmatic on like both how to do it, from like how to think about budgeting the trip, how to think about the logistics of like phone service, medical care, where you should stay, and also how to go about like reintegrating back into the workforce and society. Like whether it's you take a three-month sabbatical from your job and plan to come back, or you start putting out feelers for your next thing before you come back to the States. And it was one of those things where I had never seen somebody so clearly articulate a thing that I was thinking, that I want to do this thing now, but I also like do want to have a career and don't just want to be a drifter, right? Like he was the first person to really articulate, hey, here's how you do both. And I read that book when I was 24. My roommate had gotten it in college. My first roommate when I was like working in Atlanta, he didn't love it. He was like — he didn't have the travel bug like I did, but I read it and I was like, 'Oh, this is just a green light to go do this thing because apparently I'm not crazy for thinking this.' So, basically, Vagabonding was kind of my justification for doing the thing that I had really been kind of ruminating on for a few months.

It's so subjective though. Like it's one of those things where it's funny, like if I can — I live in New York now and like compare myself to — I have friends who like grew up in Manhattan, like super high net worth. Like I'm dirt poor compared to them, but grew up like pretty well off compared to South Georgia, right? Like when I moved to New York for grad school, like I had to pay rent, living expenses, all that. And I was like working throughout school to pay for that. But like my family covered my tuition, right? So I didn't have to take out student loans. So, I'm almost in the like the middle class of the super high net worth places where I didn't have to take on debt to do these things, but like I did have to make the ends meet to live. So, like when I decided to like go, you know, bop around Europe.

Yeah, they did. It wasn't just a free ride, right? Like I'm not a nepo baby freeloader, but also I'm not worried about going hungry. And it's like when you know that you're — you know, my — like when I called my dad and I was like, am I crazy if I want to quit my job and do this? And his advice was no. Like when my dad went to law school and was a lawyer for a few years, and he always wanted to like take a motorcycle trip around America, and then he met my mom, they got married, and he just like never did it. And his take was if you have a thing like this that you want to do, even if it feels impulsive or dumb, like you're young and should go do it, but I'm not going to pay for it. If you can basically — if you can figure out how to make the numbers work, great. If you can't, like you're coming back here and like either we have a farm — he's like you're either gonna go work on the farm, you're gonna like work for the family business, or you're going to be like doing DoorDash, right? Like he was basically like figure out how to make the numbers work and it's fine. And you know, I was in a spot where I had budgeted out where I could afford to do it, but it would be a different story if I had like student loan debt or credit card debt, right? So, like I do think everything like this is like all advice is context.

It's interesting. Like I think if I had had a lot of student loan debt, then I probably wouldn't have done it. But I also like had a football scholarship, an academic scholarship, and like you know, like it was one of those things.

Oh, moral support.

I don't know. You know, it's easy to say, 'Oh, I would have been like, fuck you,' and just done it. But like what — like at 29 maybe, but at 23 or 24, I probably wouldn't have had the balls to say that. So, I was fortunate. My family was always like very supportive of whatever I wanted to do as long as like it wasn't just stupid. But they were very much like, if you want to do a thing, cool, but don't talk about it, be about it was kind of how — that's just kind of always been the mantra. So, I can't answer that question because like I have no idea how I would have reacted to that.

Posting, but yes. [laughter]

That's what the kids are calling it. Yeah.

So there's this whole like kind of subculture on LinkedIn of what I call like performative grinding, where it's this whole group of like what I would call like either sales influencers or entrepreneurs as opposed to actual entrepreneurs, where the entire thing is like you put out content convincing people to like grind harder or do this or here's these productivity hacks, and then people are reading it because like they don't actually end up doing anything to make their lives better, and they're just reading about how to hypothetically make their lives better, and it makes them feel better. There's this whole circle of like people not really building things telling people who also aren't building things how to build things, and it's like kind of the only content on LinkedIn because unlike every other social media platform, LinkedIn is largely a professional network, which means most people aren't going to actually post entertaining stuff because they don't want to do anything that hurts their career prospects. You go on Twitter, it's unhinged and interesting. You go on Instagram or TikTok, content is all over the place. LinkedIn is like very buttoned up. LinkedIn also has like three or four times the number of users as Twitter or X or whatever we're calling it now.

It's because everybody has to be there. If you work, especially if you're working like a white-collar job, you like have to have a presence. So, I had like started writing my newsletter, and I was like — I've never done paid ads or anything, and I was always thinking through what are the most interesting channels to like find new readers. And I'd grown pretty quickly on Twitter and like Substack and whatever. But it hit me that LinkedIn was this massive — just like there was a lot of latent demand, and unlike Twitter where you're competing against a lot of engagement bait and interesting content, like LinkedIn kind of sucks, like nobody's posting there. So, I was like, 'Okay, if I can figure out how to grow on LinkedIn, I'll probably drive a lot of new readers. How do you grow on LinkedIn?' Version A, be like performative hustle slop. Option B, satirically make fun of performative hustle slop. So, like I was like, 'This could be really funny.' And I was also young enough and dumb enough I didn't think through the potential — like the whole, 'Oh, your internet footprint's around forever. Don't post anything you don't want people to see.' I was like, 'Screw that. Like I'm unemployed and then I'm in grad school. Like I'm just going to post whatever I want.' So, right after I moved to New York, I put out this long post. It starts with 'Personal finance hack of the day: how I haven't paid for food in Manhattan in four months.' And I go down this rabbit hole claiming that like, you know, my rent was three times more expensive than Atlanta, and like I wasn't making that much money in grad school. So to save money, I figured out that I could go to random hotels around the city and sign in on other people's hotel rooms and like go get the continental breakfast or like go back for dinner. And I would like take girls on dates to like hotels in Tribeca and sign off on room 421, and we would just leave before the bartender found out. And I was like, I've done the math, and there's 527 hotels in Manhattan, meaning I can do this for close to two years every day without hitting the same hotel twice. Follow me for more personal finance tips.' And it just exploded. Like the comment section was nuts. People are tagging the New York Police Department saying, 'This guy's a criminal.' And I'm like, 'What are you talking about? I'm just smarter than you.' Like I am just so playing into the bait.

Yeah. And it's you create this kind of like inside joke with the rest of the internet where 95% of people understand that it's fake, and they either think it's really funny or just lame or whatever, but like they don't — they might like it and they won't engage. But 5% of people get really pissed off about it and start yelling at you. And it's crazy because you'll see like a VP at JP Morgan like coming at your throat. I'm like, dude, everybody you work with is gonna see you commenting on bait. It's kind of like seeing somebody like comment on an AI-generated girl on Instagram saying you're so hot. It's like, dude, what are we doing here? Like you're just — this isn't a good look. And but when they comment, it puts it on like their network's feed. So you create this viral loop of people getting pissed off at satirical content that blows up, and like it just crushed. It got a little out of control because some alumni from Columbia Business School ended up emailing our dean of students a screenshot of it, and then I get an email from her. This is my like third month at grad school, and she's like, um, 'Hey, Jack...'

Yeah. Yeah. It's like the first one that got big, right? And she's like, 'Hey, Zach, this is like...' or it was probably my third or fourth, but this was the first one that really like hit like escape velocity. And I have to go meet with her about concerns about my social media content. And I emailed back, 'Hi, Dean Shabsis. Great to meet you.' Just for context. Um, or no, I didn't explain the whole thing at the time. I was like, 'Yeah, happy to come chat about this.' So, I ended up walking in her office a week later, and I was like, 'This has to be your most interesting student introduction.' And she said, 'Well, judging from your LinkedIn, you seem to be one of our more interesting first-year students.' I was like, 'Thank you.' And she says, 'So, I see this whole thing about breakfast.' She's like, 'I did my research. It seems like in [clears throat] the last month, you also claimed to have gotten vaccinated a thousand times as a side hustle when they were paying people to get the vaccine, and you called Joe Biden on his cell phone and said you wanted more student loan debt, not less, because you have that dog in you and it would make you grind more.' And I said, 'I did post both of those things.' And she's like, 'You either have some of the more interesting like side plots of any of our students, or this is like a growth marketing hack to get newsletter subscribers.' And I said, 'That's right. It is. You figured out the game.' And I was like, 'Do I need to change anything?' And she was like, 'I just needed to make sure you're not actually stealing food. It's actually really funny.' I was like, 'Okay, cool.' So, we were totally fine. She's great. We still talk a lot. But yeah, like satire as a viral content strategy works so well, and I love it. Like I've dialed it back some now because like I work for an investment group, and like we have a pretty irreverent vibe, but you also can't be like total — you have to be a little bit of a serious person now. But it was fun. Like I very much enjoy...

Yeah, it's — I'm an adult now. Like I'm not a kid anymore. But I'm glad that I did do that. I'm glad that like I get recognized from that like at least once a month still. It's hil — just in the like walking around, it's hilarious. They're like, 'You're the hotel breakfast guy,' or 'You're the Goldman Sachs beer mile guy.' And I'm like, yeah, that's — it's me.

The best comment — the best two comments on the vaccine one, somebody commented and said, 'You're the reason that minorities don't have access to vaccines.' And I was like, this is just like a — this is like a crazy direction to take this because this is so obviously fake. And then I had one claiming I got an internship at Goldman Sachs because I won a Goldman Sachs-sponsored beer mile, like where you drink a beer, run a lap, four times. And the whole bit was basically that like Goldman Sachs' CEO was a — like he used to be on the DJ circuit. He would perform at music festivals. This is real. This isn't fake. David Solomon was doing this. And people were commenting like, 'Does Goldman Sachs not have a female beer mile?' And I would be like, 'Well, they actually had a female and male beer mile. Like we — they did both.' And some people are like, 'What about people who don't drink?' And I was like, 'If you don't drink, you can't work at Goldman Sachs because every investment banker's an alcoholic.' And I'm just like just ripping back and forth. Just super toxic stuff. Yeah, it was fun. It was fun.