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

Jack Raines - writer, Slow Ventures investor, and author of the new book Young Money - built his career by going viral making fun of LinkedIn, then turned it into a job helping invest over a billion dollars in startups and creators. In this episode he makes the case against "follow your passion," explains why he backpacked the world at 24 on purpose (with an exit ramp built in), and lays out why creators with engaged audiences are the next generation of startup founders. He also tells the story of the satirical post - claiming he ate free at 527 Manhattan hotels - that got him tagged to the NYPD and summoned to his business-school dean's office. Part career playbook, part comedy, part contrarian investing thesis on where money and media are headed.

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Transcript

SPEAKER_00 0:00

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. Your passion might not pay, is what you're saying.

SPEAKER_01 0:13

It's actually worse than that. You're working with a VC group now.

SPEAKER_00 0:16

I have you're investing in creators. 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, right? On the creator stuff, these people have YouTube channels, they have newsletters, they have podcasts.

SPEAKER_01 0:30

Think your skill at spotting talent and people's gonna serve you well, Jack.

SPEAKER_00 0:33

That's like literally my job, so I try to be good at it.

SPEAKER_01 0:38

Jack Reigns, I'm excited for this one. I've seen you at a couple interviews with you, and I think this is gonna be a lot of fun. Let's go, Matt. Thanks for having me. Got a big deal going on with a new book dropping. Name of the book is Young Money. That's right. It's interesting title because when I was young, I had no money. But is it really about what to do with money when you're young or what's really it's funny?

SPEAKER_00 1:00

I've got like, you know, the the subtitle is a field guide to wealth and purpose in your twenties. I wouldn't call it a typical personal finance book. It's also not a rap label, little way. And I'm hoping he doesn't sue me for trying to steal his uh company name with Young Money. Um the the book is really about like thinking about opportunity costs, and like money plays a role in that, right? Like I consider opportunity costs broadly how you spend your time in different, you know, 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 these like 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 like 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 it's really a book on opportunity cost and you know, any stuff related to money is framed within that lens.

SPEAKER_01 2:04

Interesting you say that because you know, I do a lot of work talking about opportunities in the trades and stuff. And and part of it is like trying it doesn't mean you're stuck with it forever. Right. And I feel like there's so much pressure on young people to have it figured out at 18. Like what they're gonna do with their whole life is supposed to be known right when you're heading into college and making those decisions. That seems like a whole lot of pressure for someone that can't possibly know their whole life at that age, I don't think.

SPEAKER_00 2:30

Well, the worst part of it is too, is like, I mean, like I you know and I like I I read up on your background, listened to some of your stuff before this. So like I'm 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 like high income. Like most like I 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 like that's a whole other thing. But on the like figuring your life out at 18, there's also always this like 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, where you know, and 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 um it just kind of becomes a status game. Like, 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 uh it's it's a it's a massive problem, particularly with the 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.

SPEAKER_01 3:55

So I feel like talking to you is is great on this subject because you've kind of you've kind of drank your own Kool-Aid. You you've somehow figured out to from what I've seen that you've done already in your life, you did do what you're encouraging others to do in your 20s. How did you figure that out? Because that's not everybody at all. Everybody else does what everybody what what mom and dad push you to do, what what society says you're supposed to do, I think is what most people feel stuck doing. You you somehow win a little rogue on that, which is great.

SPEAKER_00 4:32

So I my my like take on call it like life construction is that on one hand, like I'm very motivated to make a lot of money, be successful. Like I I do not want to be in my 40s and feel like I'm poor, right? Like that's like that, that was never I'm in my late 20s now, there was never something I wanted, but I was also really cognizant at like 23 or 24 that I was only gonna 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 gonna want to do when you're older, you aren't gonna enjoy doing when you're older, or you just won't have the opportunity to because life responsibilities and complexity and all that. So, like to your 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. Um, I love studying abroad. My grandma takes like every grandkid of the family 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 like 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, ooh, 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 where the hotel is copped, or like I'm actually staying somewhere nice. And I was like a couple years out of college, I realized I had 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 my kind of take on it was I I had a couple of things going for me. I'd saved up a little bit of money in my first job. I'd I'd got into uh a good graduate school and I knew I was gonna 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 gonna 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, that 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, like 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.

SPEAKER_01 8:01

Well, what I just heard is you you did something that was well thought out and experience you wanted to have, and thought through it really well. Whereas from the outside looking in, a lot of people see a young person do that, and it's probably impulsive with with no outcome in mind. So um it's that thought process that uh has really helped you, is my is my bet on the experiment.

SPEAKER_00 8:25

Well, I mean, it's it's like anything else, just like being intentional and like thinking through how you want to do thing is more important than whatever the thing is, right? Like as long, 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 like time frame in which I will do things, 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 it's 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?

SPEAKER_01 9:18

Agree with you a hundred percent. The the best thing to mitigate risk is time, and you have no more time than when you're you're young, so can definitely subscribe to this. You read a little bit uh and reading your background. You read you stayed up all night once and read a book, I think, called Vagabonding that might have helped influence some of this. What what'd you read there and how did that change or help your thinking?

SPEAKER_00 9:40

So it's funny. Do you know um, do you know who Tim Ferris is, the four-hour work week guy? He um so I've read like a bunch, like I've read a lot of his blog posts and a couple of his books. He actually had this whole thing where he was burnt 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. Um, 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. Um, but vagabonding is 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 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 it's 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 in college. Um, my like first roommate when I was like working in Atlanta, he didn't love it. He was like, it's 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 it basically was the the vagabonding was kind of my justification for doing thing that I had really been kind of ruminating on for a few months.

SPEAKER_01 12:33

Now I I can tell you that I've been nose to the grindstone since I was a teenager. So I've done the exact opposite of what you're encouraging, and probably gonna wish I did more of what you're encouraging, but now I'm starting to pay attention to that, starting to try to you know put some life events more often in besides just career events.

SPEAKER_00 12:58

It's it's so subjective though. Like it's it's one of those things where it's funny, like if if I can I live in New York now and like compare myself to I have friends who had 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 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 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.

SPEAKER_01 13:41

Sounds like your parents figured out a right mix for you then. Yeah, they did. So it wasn't just a free ride. Right.

SPEAKER_00 13:45

Like I'm like, I'm not 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 my like like when I 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 like, no. Like when I 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 gonna pay for it. If you can fit 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 gonna be like doing DoorDash, right? Like he's he's 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 I'd 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 contest.

SPEAKER_01 14:49

What I would ask you is what if you didn't have his support? What if you did it anyway?

SPEAKER_00 14:53

It's it's interesting. Like I I think if I 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, I'd like it was one of those things.

SPEAKER_01 15:08

Not financial, I meant more moral support. Moral support.

SPEAKER_00 15:11

Yeah, like what if he'd have condemned it? I don't know. You know, it's it's it's easy to say, oh, I would have been like fuck you and just done it. But like what like like at 29 maybe, but at 23 or 24, I probably wouldn't have had the balls to say that. So um I I 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. Um, 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 the that 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.

SPEAKER_01 15:46

Well, great thing to be thankful that you had uh supportive parents on it, I I think for sure. You know, one thing I want to talk about and and for sure is because I think everything's better with a little humor. Um, and one of the things that you're most known for, I think, is the the the satire and the humor on LinkedIn.

SPEAKER_00 16:08

The specific term is shit posting, but yes. Is that what it's called? That's what the kids are calling it, yeah.

SPEAKER_01 16:14

Can tell how unhip I I am on on on some of it. So um maybe for those that haven't heard, what what direction did you take on LinkedIn and and why?

SPEAKER_00 16:26

So 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 um 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. Then people are reading it because like they don't actually end up doing anything to make their lives better, they're just reading about how to hypothetically make their lives better and it makes them feel better. It'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. And is that true? It's that big. 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 never 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 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, B 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 I'm unemployed and then I'm in grad school. Like I'm just gonna 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 in 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'm just so playing into the bit. So you would double down on the hate.

SPEAKER_01 19:41

Yeah, yeah, yeah.

SPEAKER_00 19:42

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 VP of 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 like 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 and but when they comment, it puts it on like their networks feed. So you create this viral loop of people getting pissed off at satirical content that blows up and like it it just crushed. And 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. This is your very first one, your very first post. Yeah, yeah, yeah. It's like the first one that got big, right? And she's like, Hey Jack, 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 got it. I have to go at a meet with her about concerns about my social media content. And I email back, hi Dean Shabsis, great to meet you. Just for context. Um, or no, I I didn't explain the whole thing at the time. I was like, Yeah, happy to come chat about this. So I end up 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've seen 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 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 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. Um, 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 shit. You have to be a little bit of a serious person now. Um, but it was fun. Like, I very much enjoyed it. Yeah, it's like I'm an adult now, like I'm not a kid anymore. But I'm 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 like just in the real like walking around, it's hilarious. 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. I'm him.

SPEAKER_01 22:47

That's great. I guess I never really thought about it from the perspective of if you took it seriously and and didn't get the joke, you kind of embarrass yourself probably for a lot of people.

SPEAKER_00 23:00

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 crazy direction to take this because this is so obviously fake. And then I have one claiming I uh I got an internship at Goldman Sachs because I want 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 uh like he used to be on the DJ circuit, he would perform at music festivals. This is real, and this isn't fake. David Solomon was doing this, and people were commenting like, does Goldman Sachs not have a female beer mile? And then I would be like, Well, they actually had a female and male beer mile. Like we they did both, and then 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 riffing back and forth. Just super toxic stuff. Um, yeah, it was fun. It was fun.

SPEAKER_01 23:57

You know, uh interesting because we're we're taking that something similar at at Crash Champions or even mine, because you know, with any business you get the hater sometimes too. And rather than taking the approach of hiding the the the comment or something, we're just gonna start embracing it and give give a little humor back. We'll see how it goes.

SPEAKER_00 24:21

It could be like a hater of the week where it's like a LinkedIn or Instagram reel where it's like it's just like screenshots of comments of people telling you to like kill yourself or you're a bad person or whatever. It's like it's it's good to highlight the hate because also people forget that like when you're it's easier to just it's easier to be mean behind like the facade of the internet. And when you actually like engage with things, sometimes people are like, oh, somebody's actually reading this. Like there's this, oh man, like I I forget that there are other people on the other side of these. So I do.

SPEAKER_01 24:51

Yeah, and that's the clear, like we want to make it right by the person anyway. If totally something went wrong, so we're we're gonna go ahead and fix it, but rather than just ignore it online and deal with it out off online, we might as well embrace it online too. So we'll see how it goes. Cool. It was a young person that brought that idea to me.

SPEAKER_00 25:07

So I mean, listen, the young people are full of great ideas sometimes.

SPEAKER_01 25:11

Yeah, I'm a guy who grew up without any technology, so um, it doesn't surprise me that I'm not the idea guy on how to how to do it right on on social media. Yeah. From from that, now you mentioned something. You're you're working with a VC group now. I am, yep. So tell me about that because it's not just you're not investing in in businesses, right? You're investing in creators.

SPEAKER_00 25:38

So we have we we have two funds that I work across. So I'm at um I'm in an early stage venture capital fund called Slow Ventures. We manage like a little bit over a billion dollars. Um, we've been around for like over a decade. I've been there for about a year and a half. Um I joined to work on two funds. We have one that like invests in startups, so like all the tech stuff you're seeing in Silicon Valley and New York, we're in the middle of all of that. Like you're meeting with all these like wizard kids from Stanford and MIT that are building like AI for dogs. We're talking to those kids. And I don't know what half the stuff is half the time. And it's like, and then you're like, oh like yeah, we just raised like a hundred million dollars for like distilling AI for tractors. And I'm like, I don't know what any of that means, but congrats. I guess somebody does. Um, and then the other half is we've increasingly, and um, I mean, you have a platform, so I'm sure you've picked up on this too. Like, there's this increasing trend of there's so much slop on the internet now, like both so many people posting, so much AI generated content that everybody's internet is different now. Like it used to be the internet was kind of like you had the one Facebook news feed, or media was a few TV channels, and now everything's so algorithmically driven that everybody has their own corner of the internet. But there's certain people that carve out their kind of niche as like call it the like market or segment or theme leader in whatever their space is. Like, like there's people who are just really, really, really dominant. Like you could argue James Clear was one of the OGs doing this with like just talking about like habits and like life productivity. And like he's like okay, he's the habit guy, right? Um, but there's there's a lot of different versions of this in pretty much any vertical. And we we had this bet that basically, okay, AI is making it easier and easier to make software and just like create technology. Um, distribution is actually getting harder and harder because there's so much noise. Like everything from the cost of running meta ads and Google ads gets more and more competitive. Like there's no like easy distribution that's cheap anymore. But if you have millions of followers or subscribers who love your stuff and who are super engaged, guess what? It's much easier to like grow a business and find buyers and find customers and like get feedback from those customers and build stuff faster. It's kind of like, I don't know, like the Kardashians, their ability to like spin up brands and make money off of them. Yeah, when when they have the entire world watching what they're doing, you can get eyeballs on skims really fast. Or Haley Bieber, or there's like so many versions of this with like people with massive online influence being able to leverage that influence to benefit their brands. The Paul brothers, right? There's there's just this is an obvious thing. Tom Brady's doing it with all of his endorsement deals now and companies he's invested in. So we raised a separate fund where we are now investing in uh like creators and specifically like what we call creator entrepreneurs who they have a platform, they've built an audience in a specific niche, and they figured out how to build businesses on top of that, or have very good hypotheses for building businesses on top of that that are like high leverage, scalable, and they want to raise a couple million dollars to hire people, invest in technology, blah, blah, blah. And our bet is these people with platforms could build two, three, four companies off of these platforms. Then we have stakes in all of them. So we've been doing it for a little over a year now. It's still pretty early, but like it feels like the world is kind of waking up to this. Like CAA just raised like a big multi-hundred million dollar fund to like invest in kind of creator-len commerce brands. Like this is this is very much where like a big part of the media content world is going. And I think we're really early to it.

SPEAKER_01 29:21

Yeah, I I think it's a great idea. I mean, quite honestly, I'm trying to build a platform to to support my business, to promote my business.

SPEAKER_00 29:30

Yep.

SPEAKER_01 29:31

What you're basically saying is people who uh already have are on the verge of the platform can launch the business um in the right in the right segment. So uh it's it's it's the opposite direction of I did the business first and now I'm trying to grow the business bigger through building a platform. Yep. You're you're trying to catch the people at you, hey, you got this platform, can we help you do something with it? Yep. How do you get them mad? Because you probably want to catch them right before they blow up or right as they're blowing up, right? Like so it is there some intuition behind it that's it's it's hard, right?

SPEAKER_00 30:10

Like it's it's one of those things where the good thing and bad thing about like the call it creator investments versus normal startups, a lot of these people are more visible earlier. Like, there's no way to know, like, 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, right? Like, and then all of a sudden you see, oh, so-and-so raised $40 million to build these types of robots. You actually can't stay on top of all those because like they're in the shadows, and so much of it is like you just have to have the right network where like stuff gets funneled to you. On the creator stuff, these people have YouTube channels, they have newsletters, they have podcasts, like there's a lot of publicly available information about them. So, like being able to use like web search or even like AI tools that can go out and like find creators in interesting niches makes it much easier to find people who have good, good engaged audiences. But the hard part about creators are like a lot of them aren't entrepreneurial. Like the the overlap of person who knows how to make compelling content and build an audience, and also person who's like very entrepreneurially driven. Like, like I would put you probably in the camp of like very strong entrepreneur who's realized content has leverage and is now figuring out content thing, right?

SPEAKER_01 31:25

And like exactly right. Yeah, and not very good at it either, but but trying, yes.

SPEAKER_00 31:29

So so there's like there's a there's a lot of people who are like they figured out the content thing and think they want to be an entrepreneur, but like being an entrepreneur, like a lot of it really sucks. Like the idea of like, like there's people who want to have a company, but like the but actually like doing the like gritty work of building it day to day just kind of sucks. So being able to suss out like pattern matching, okay, what attributes we're looking at like a tech company founder, like grit, discipline, just like general ability to like be a winner and also be very smart in their market. We have to layer that on top of person who's also good at building audience. So it ends up with like there's a lot of people with big audiences that probably just like either they don't want to build the business, or if you're making a million a year on brand deals, like there's not a lot of incentive to like risk cutting that revenue to like build your own thing where if it works, you know, the equity value of your thing could be worth multiples of what you're making cash flow every year from brand deals. But do you want to take that two to three year hit and uncertainty where it might not work? Like that's just not a trade a lot of people want to make. So it's like there's there's a lot of ways to find people to talk to that have big audiences, but then the intuition and the diligence work is about sussing out like, have they built like you start evaluating the you know, you you have to do the work of like, okay, do they actually have an audience? And like, are they growing and like are people engaged? Cool. Assuming you have that, all right. Then you're looking at it like any other business investment. It's like, is this entrepreneur really good? Are they scrappy? Like, what have they proven while bootstrapped or on minimal amount of capital raised? Like, do they actually like do they want to build a really big business? Like, do we trust that they're in this for like five to 10 years or are they gonna burn out in a year? Like it's a lot of the same, you know, human and business diligence you do for looking at any other investment. Um, and yeah, it's kind of over time you develop an intuition for like they have it or they don't. But there's basically just one additional step versus evaluating any other investment opportunity.

SPEAKER_01 33:31

Yeah, I think it's no take, for example, talk to the guy to the investors on Shark Tank. Like it's it's the horse they're betting on more than the idea all the time. So you're betting on the you're doing the same thing, betting on a horse, you just don't have a business yet, maybe to model. So it depends.

SPEAKER_00 33:49

Sometimes they do, sometimes they don't. Like we've done, we've done deals where like they're making a few million dollars already, and we've done some where maybe they haven't, but this person has been working like two part-time jobs while also building the platform and they've fully mapped out what their wedge is going to be, where you know, they're just executing at a really high level. And by giving them money, it gives them the flexibility to like quit one or both of those jobs to spend more time on this. And like it's like, okay, maybe you do a lower valuation on this deal because they haven't proven out the business, but they have proven out a very, very capable person who has high velocity who can build a business. So it there, there's a whole spectrum of like this thing is working. I need to raise capital to grow it quickly, and I think this thing will work. I'll raise a little bit less capital at a lower price to like prove it out, and then you guys can put more in as it works. Love it.

SPEAKER_01 34:39

What's your what's your take? Where are you at on the camp of maybe playing it safe versus controversial? Uh from what you've done, you're not afraid to get a little edgy, obviously.

SPEAKER_00 34:53

But are you talking are you talking about like publicly spoken opinions about like what you do with your career? Like we can take this in all sorts of directions.

SPEAKER_01 35:01

Yeah, I guess like I would say my platform has pretty played it pretty safe so far, and others have encouraged me not to play play it so safe. Uh the world's pretty we're pretty politically divided. It's easy to say something to offend people, and then others would say offending a few people is the exact way to go. Curious how you feel.

SPEAKER_00 35:21

My my take on a lot of stuff is like I think like I'm very careful to steer away from like politics, religion, like all the stuff you're not supposed to talk about on like a on like a first date or a cocktail party. It's like there's there's very few wins you're gonna strike up with talking politics, religion, divisive stuff, unless the the the one caveat on that is like if you can do it in like a disarming, humorous way, it's fine. Like typically the only time I bring stuff in is if it's like slightly self-deprecating humor to like make other people feel at ease. Fine. Like that works, right? But like I think it's just a like, I think it's a zero-sum game to like try to be overly opinionated about the kind of controversial topics unless you have a very specific reason to do so, or unless like, you know, your platform is actually like like I don't know, if you're like a Fox News commentator or like a CNN commentator, that's kind of your job. Like you should do that. But for like normal person building thing, I I just don't think that that's useful. But I do think being opinionated in general is very useful. Like you should have things you agree with and disagree with on and like be public about those. For example, there's the hypothetical infinite number of like startups that we can look at, right? By like writing frequently online about like things we think and don't think about markets. Like you go, like some of the AI stuff on like, okay, like if you think open AI and anthropic are crazy overvalued and like they have no real edge and their tech is gonna become like a commodity, and you can take that stance. A lot of people disagree with you, but the people who agree with you that are building companies that if that version of the future comes true could have massive opportunities to get big, they're gonna want to work with you because they know you already agree with their vision of the world. So, my take in general is like like don't don't be over-opinionated in zero-sum games that don't actually like forward your mission. But like, if like my job as an investor, putting out takes that some people disagree with and some agree with, but like you don't have time to meet with everybody or talk to everybody. So you kind of you have to set up a filtering mechanism for like who do I want to care about my thing. It was kind of the same thing when I was working on my book, right? Like the first time I pitched this thing, I didn't want to target a certain age demographic. I wanted to make it broadly about like opportunity cost and life optimization, which I don't think my book is only applicable to young people, but I do think by gearing the messaging toward people who are in a stage of life that I am in or was previously in, it just like they feel more drawn to it immediately. And you want like uh, like it'd be much better to have a ton of like 25-year-olds like just super fanning my book than like a bunch of people thinking it's fine, but not really feeling like it's for them. So being opinionated online is useful in that like it helps you attract your tribe and repel people that probably wouldn't be a fit anyway. But you should just be opinionated about the things that actually move the needle for what you care about, whether it's like book sales, business opportunities. Same thing with like dating. It's like, I don't know, like if you if you try to be somebody like I'm like a single dude in my late 20s in New York, if you try to be like the guy that fits for everybody, like you'll probably get a second date and then nice to meet you, but like it didn't really stick. Like you should probably be somewhat divisive where people are like really into it or they're not. So you just gotta pick the right things to be divisive about.

SPEAKER_01 38:43

Yeah, I think I agree with uh what you said. Uh an example for me would be the the the the blue collar versus college. Yeah. So I I I don't condemn college, I just want people to know there's other ways. Yeah. And you might disagree with me, and that's fine. Um, but you don't necessarily have to hate me just because of it. So there's there's things that people are gonna hate you because you went there, and there's things that this is an opinion and it's valid, and you can disagree, it's okay.

SPEAKER_00 39:12

And guess what? The world's big enough that like there's plenty of people who take both sides of that argument, and like you don't have to win all of them. Like like you were trying to attract people who like either agree with you or who find your take on this really interesting and want to learn more about it. The worst thing you could do is like repeatedly hedge that opinion to not piss off the people who wouldn't work with you anyway, right? Like that's that's just like that's a losing uh proposition.

SPEAKER_01 39:35

Do you think the world's gonna punish young people for stupid stuff they put online when they were young? Because, you know, I never had to worry about that when I grew up. There weren't there weren't even cameras on phones yet. So I there's plenty of stuff I wouldn't be proud if it were online that I did when I was young. So I feel like it's something to worry about, but I also feel the world's probably gonna forgive young people for being silly.

SPEAKER_00 39:58

So my um I have like uh a couple of different takes on this.

SPEAKER_01 40:02

I actually Although I would tell my kids not to post it.

SPEAKER_00 40:04

So I I think we I think we hit peak cancel culture a few years ago where the whole like somebody gets drafted by the NFL or NBA and then a tweet comes out where they like called their friend gay when they were 13. It's like, come on, man, like this guy isn't homophobic. He was just like a dumb 13-year-old. It's like there's there's just certain things that were getting called out in like called 2018 to 2022 that just are you really gonna judge a 23-year-old guy because he tweeted like something that was slightly edgy at 13? And also, also like cultural windows shift a lot where you start like evaluating, like if you retroactively evaluate a thing now based off of like what people didn't care about back then, you can play that game all day, like going back in history where like there's stuff that happened 80 years ago that would be appalling if it happened today. But like, yeah, if that person was alive today, they wouldn't do it today, right? Because it's just like a moment in time, and it doesn't make stuff right or wrong. It's just like you have to take context into account when people are saying stuff. And my my general rule on thing is like like don't be racist, don't be misogynistic, right? Like, don't like basically don't do like don't do or say discriminatory things. But outside of that, if you say thing that's like the wrong opinion or piss people off, I just think there was so much unnecessary, like kind of like wits trial, scarlet lettering of people for stuff that just didn't really hurt anybody. I think everybody just got collectively tired of it. Like this whole like everybody was walking on eggshells and like 2020 about all sorts of stuff, like it just like grow up. Like nobody actually cares. But the flip side of that is because there's so many weird niche, edgy communities um online now. I think there's a lot of college kids who like grow up and spend too much time in like a certain Discord server, subreddit, corner of Twitter live stream where there's like these super niche conspiracy theory type of things that go out of control. Like, are you familiar with uh Clavicular, the looks maxing guy? You know what I'm talking about?

SPEAKER_01 42:04

I've heard of it, but I'm not familiar enough to say that's like uh like a 21 year old.

SPEAKER_00 42:08

I don't even know if he actually believes the stuff he's putting out there, but he's got a massive audience. Like he's been like, like, he's been like taking like testosterone and all this stuff. And he's like 21, right? He shouldn't be touching any of this stuff. And he's got this whole take, he's got this like like he's almost like In fact, it's probably gonna regret that when he's older. Well, there's there's this whole like uh there's always like in your cycle of like the pickup artist type. Like there was like Neil Strauss, the game. There were different guys who had did this at different periods. He's sort of like a cartoon character or a caricature version of that, where like he's like intelligence doesn't matter, like nothing the only thing that matters is like he calls it looks maxing or like being attractive. And it's like he has this like oh like he's like it's almost misogyny and like like degrading women, but also it's like almost ignoring women and saying like guys just need to like maximize like male attractiveness for the sake of doing it. And I don't even know if he's like I actually don't know if he actually believes this take or if this is just like a performative thing, but there's like a lot of like 15, 16-year-old dudes that kind of look up to this guy as like a guy worth like venerating and like this is the thing we should be optimizing for. Where you spend like four or five years in internet echo chamber, you might tweet or like post on Instagram some just really edgy, messed up stuff where if the you know the version like 15 years ago was like like just making a dumb joke about your buddy that's like, yeah, you probably shouldn't have tweeted that, but it's fine. You now get stuff that's so much more fringe aggressive and like just really weird pockets that like I think there's gonna be more young people that take that take like the really extreme stance on a thing, whether it's like racism, anti Semitism, misogyny, whatever, where they don't even realize what they're saying, but they say something super messed up. Could haunt them for life, but the canceling people for pretty benign stuff, I think we're kind of past that. So it's like most normal stuff you won't get canceled for. And I think in general, posting on the internet is a good thing. The risk of like doing something super, super out there that haunts you is like much higher. And also, like it's really easy to just get on your phone and put that thing like impulsively. That's actually the real thing. There's no friction between thought and posting. So if you're impulsive, you might just do a thing that you're gonna regret.

SPEAKER_01 44:28

So it's silly or stupid young people stuff for given.

SPEAKER_00 44:34

Uh super edgy stuff. You're an absolute whole thing. Yeah, yeah, yeah. Yeah, yeah, you might be you might be totally cooked. Right.

SPEAKER_01 44:43

Yeah, which is how real life kind of works too, right?

SPEAKER_00 44:46

That's how it should work.

SPEAKER_01 44:48

So maybe the whole uh social media world's catching up to reality. Good old-fashioned reality goes, maybe. Where's the jack 10 years from now? What what do you out of all the stuff you're experiencing or dipping your toe in, so to speak, or or even full on bent on, 10 years from now, where where do you see yourself?

SPEAKER_00 45:10

Yeah, I mean it's a good question. Like I I I've worn a few different hats in my 20s, and the things I've kind of landed on are like I love writing. I love like, you know, podcasting, stuff like this. Like the I would say thing that will definitely be there is like I'll still be writing. I'll probably write more books. Like there's a good chance I have a podcast or some other like medium like this. Um, but I don't really ever want media to be like my full-time thing. Like I like my job a lot investing at a venture capital fund. So there's a very good chance, and I I love keeping up with like tech trends and just like what people are working on. So whether I end up starting my own thing or not, I'll probably always be involved either working for or slash with like tech companies or like investing in them. And then I think I'm always gonna want a platform to just like you know, put my opinions out there and also just BS with people. It's kind of fun. I mean, I I think a platform is a thing that compounds over time. And then as that compounds, it just like it keeps bringing me new opportunities to meet interesting people where I don't want to like overly narrow my options to like, oh, I have to like do this at this company or like I have to start this company. But like keep doing things in the compound and then opportunistically, like when they're like I ended up at current job because it was like I thought that given my platform and interest in tech investing and all that, like VC could be very, be very interesting. And then like the fund I'm that slow happened to be hiring, and like I kind of liked everybody's shtick there when I was looking into them, and it was just like right place, right time. They like me, I like them. So that's not a thing I would have planned five years ago, right? So I the my bet is like keep chasing the things I'm interested in, and then like as opportunities to like like high-leverage opportunities and those interests appear, run after them.

SPEAKER_01 47:00

Wish you all the best, that's for sure. You know, what I would like to ask is big lessons you've learned already. Like, what how about a mistake or something that ri that that stuck with you?

SPEAKER_00 47:12

Yeah. I mean, I I think that there's I'm very anti-pursue your passion as a career thing. I think pursuing your passion is great when you're already rich. And I think it's fine. I think it's fine to do when you're really young and dumb. Your passion might not pay, is what you're saying. Well, it's it's true, it's actually worse than that. Like, one, no, it almost certainly won't. And two, even if it does, you probably won't like it that much anymore because it becomes stressful when like your passion isn't the thing that puts food on the table, right? So my example is writing. Um, my my first job after graduate school, I like didn't I was in this like I love the writing and media and podcasting, and I've always liked you know investing. And it's like, okay, I tried to split the difference in grad school where I interned for a different venture capital fund, and I was helping them basically like marketing editorial content, yada yada, yada. Didn't love that because it felt like by splitting the middle, I wasn't really getting either because like I was very I was like, I could only write about like stuff relevant to the fund, but I also wasn't the one meeting with founders, writing checks, all that. Um, so I like I got a job offer from Robinhood, the like stock trading platform, to um they were building a media subsidiary called Sherwood News. It was a cool opportunity. I was gonna go in like podcast newsletters, build out different content verticals. And I'd always liked writing, and that was what I did in grad school. When I was like backpacking Europe, I was writing a blog. Like I kind of just thought that was gonna be my thing. When I got there, I quickly realized it was my first time having like a full-time W-2 day job in media. And I kind of realized I liked riding my brain blasts as they hit me and yapping on the internet, but like I didn't love the like structured, like content cadence. You have to put out this, like the output is like you have to have this much every week or every day. It just kind of like it just wasn't what I wanted to do. And then, you know, looking forward, it there like the the career outlook in call it journalism isn't that great unless you kind of start your own platform and have all the leverage. And I just like that's just not what I wanted to do. It wasn't gonna pay me what I wanted, you know, into my 30s and 40s. And I was just like, this is the wrong bet. But I was very tunnel-visioned from like riding, riding, writing. I was fortunate that I was able to leverage the platform that I built to like move into venture capital world, which is much more where I want to be like tech, investing, financial markets. Um, but it was a misstep. It was a thing where if I'd been more thoughtful in grad school, I probably would have played that differently, but I course corrected really quickly. And it's like, would I do it differently? Probably not, because I learned a ton then. It like I made that move pretty quickly. And also, like candidly, I'm happy that the fund, I'm happy with the fund that I joined. And that opportunity actually wasn't there until I hit the point that I needed to make that switch. They just weren't hiring nine months before that. But um, yeah, like I I think compared to my early 20s, I think money matters more than it did when I was younger, which is pretty aligned with what I say in the book. Like the like it takes more and more money to maintain standard of living you want as you get older, because like life gets more expensive. Family stuff, you just have higher standards and like desires. Um, so that's not really a change. It's like it's a thing that I knew would happen, but I'm experiencing it now. Like, I want to make more money than I did at 23. I think that's understandable. Um, but like I'm like very anti-pursue your passion. And my take is actually like while I stand by the idea that like if you have a crazy thing you want to do and a finite window to do it, you should go do it. I think on the whole like pursue your passion stuff, whatever that thing is, start it as like a either keep it as a hobby or start it as a side hustle on the weekends. And if you hit the point that like it can replace 75% of your income and you want to double down, great. But like don't preemptively try to focus your career on passion or you'll probably end up pretty disappointed. Love it. So for the book, for sale everywhere? For sale everywhere. So I guess we're recording this on July 30th. I don't know when the episode is gonna come out. So I'm assuming when it comes out, it's either for sale everywhere or about to be for sale everywhere.

SPEAKER_01 51:11

Um probably for sale everywhere.

SPEAKER_00 51:13

Yep. As of August 4th, for sale everywhere. Young Money by Jack Reigns, Amazon, Barnes and Noble, Books a Million. Apparently that still exists. Um, Books a Million. We have the audio book to Spotify, Apple. Um, if you like listening to me here, you can listen to it there. And the whole thing is it's all opportunity cost, status games, like how to not regret not getting what you want out of the current stage of life. But yeah, go buy a hundred copies. Please try to earn out my advance.

SPEAKER_01 51:40

Uh, very good. Now, we always close this podcast by asking, you know, we're all about championing people. Yep. And so always close it by asking the question uh given the platform here, who would you in your life like to champion and why?

SPEAKER_00 51:56

Oh, so I got this, I got this kid who's like, he's like about to start college and he's a total wizard, right? Kids' name is uh Noah Barbados, and he like hit up, he actually hit up my boss just to like, he was like 17 Canadian kid, like working on a bunch of random tech stuff. And he's like, hey, I just kind of want to chat. And he like sent a whole list. Most high school kids, their hobbies are like playing football and chasing girls. And he had like, oh, I've started working on this company and that company. I'm working for the startup, and I'm also training for a marathon. And my boss, Sam, was like, you should just like talk to this kid, see what he's up to. And like, he now, we've stayed in touch. That was a year ago, and he sends me like a monthly update on what he's working on. He like started and sold an agency, basically like a search engine agency, but for AI chatbots. Like, started, sold that, has started another company where he's going to raise venture capital for it. Um, he got into like a very good school in Canada and is still planning on going to college. He was also interning for like a really big like Canadian fintech company. So he basically had two and a half full-time jobs, sold a company, started another startup, and it also like ran like a mare. Like he's the dude's just like wheeling and dealing at a pretty high level for the high school. Really? Yeah. So like I don't know. I I'm kind of I'm kind of waiting for him to have a like really big, interesting idea he's all in on, and just gonna be like, yo, like, here's some money. Just like go, you know, like go make yourself really rich and make me like moderately rich. Um, but like, yeah, Noah is great. I'm like a I'm a big fan in general of just like young kids who are just like really hungry and like excited about life and are like, I'm just gonna go get this thing. And he's one of those guys.

SPEAKER_01 53:34

I think your skill at spot and talent and people is gonna serve you well, Jay.

SPEAKER_00 53:38

I hope so. I hope so. We'll see. That's like literally my job.

SPEAKER_01 53:41

So I try to be good at it. Yep. Well, thanks for spending the time today. Appreciate it. Matt, thanks for having me. All the best with the book. Thank you.