The Rundown - Why You Should Take More Risks in Your 20s (ft. Jack Raines)

Episode Date: September 7, 2026

Jack Raines, Venture Capitalist and Author, joins The Rundown to explain why your 20s might be the best time to take bigger risks with your career, money and life. He shares how he turned $6,000 into $400,000 trading SPACs and eventually built a career through writing and posting online. Jack also breaks down the philosophy behind his new book, Young Money, and why he thinks young people should worry less about optimizing every dollar and more about maximizing the unique opportunities of early adulthood. Plus, he and Zaid discuss the value of making financial mistakes while the stakes are still low, building an unconventional career and knowing when to spend money on experiences instead of saving it.

Welcome back to the rundown, interview edition. Today, we are talking to Jack Raines, the author of a new book called Young Money. Jack and I have been internet friends for years now, but this was actually our first face-to-face conversation. We recorded it about a couple weeks ago. And honestly, it barely felt like an interview. It felt more like just two guys chopping it up, talking about money, career, risk-taking, all that stuff.

We got into Jack's unusual career path from working a normal corporate job to writing a book. We also talked about how Jack turned $6,000 into almost $400,000 trading Spacks back in 2021, and we got into some of the ideas behind the book and how hard it is to write an actual book. One quick heads up, though, this conversation is more casual than our typical interviews, and there were a couple choice four-letter words that started flying in the middle of it, so fair warning if you're listening around the kids. That being said, this was a really fun conversation. I think you guys are going to really enjoy it, so let's get into it.

All right, guys, today we are talking to Jack Raines. I'm a big fan of Jack's work. I've been a big fan of his work for a long time. Now he's an incredible writer. He's an investor. He's a professional shit poster. He's now a published author. Jack, welcome to the rundown.

Zay, thanks for having me. I like the accolades you gave me. Professional shit poster way better than author, VC, or anything else. I mean, dude, it's true, though. That's kind of how you burst onto the scenes. You're not wrong. I want to start there. Okay.

I mean, look, this is why. This is why I love your story, man. I've been, I've been, you know, big fan of your work for a long time now. So let's just kind of get into it. You know, before we talk about the book and anything else, let's talk about, like, how you, you know, got to where you are today. Your career is so interesting, you know, you started off just like, I think a lot of people do. You went to college. You got a degree.

You got a normal finance job. And then you started writing online. You started shit posting online. And then now you're, again, a published author, new book out, Young Money. And you're, uh, you work for a VC firm. slow venture. So how did all that happen? So there's this funny thing in venture capital where every VC wants to like, they become a VC, realize, oh, I should be a thought leader or build a personal brand. They kind of inverted that where I was just addicted to posting on the internet when I was

23, 24, 25. And there was initially no grand plan behind it other than I was just leaning into my dopamine addiction. And it did hilariously end up leading to a book deal and a job offer. And it almost got me kicked out of business school at one point. But no, I mean, I was very addicted to posting, and it turns out if you're opinionated on the internet that somewhat know what you're talking about, people like it. And a lot of it was also just a newsletter growth hack where I knew if I could go viral online, I could funnel some amount of that to a newsletter list, get more subscribers, have more people read my stuff. So there was a little bit of methods of the madness, but it's just, it's fun to fuck around on the internet. People seriously, like, underestimate it. So like, kind of walk me

through. So you just graduated college. Like you're working your desk job, right? And I think this is relatable to a lot of people. They're doing their thing. They're working. They're earning a paycheck. But like you just always had this side thing that you were passionate about. So for you, it was writing online. You had a blog that you started. And then just from there, like, when did you start getting traction? And when did you know that like the best way to like growth hack your blog was just to write funny stuff on LinkedIn, triggering a lot of people? So to take a step back, I had a burner Reddit account called Barmello-Zanthony in 2020. And it was like a play on words for Carmelo and Anthony and Zadax Bar. My entire fraternity chat had like edgy drug-related like names,

nicknames in our group me. And I made that my Reddit name. And the picture was one of the thumb-thumb-thums or whatever from spy kids. Really, yeah. So COVID hits, like a lot of other 22, 23-year-old guys, I was working remote, corporate finance, really bored. And I started creating spacks. Specifically, I was trading SPAC warrants in my Roth IRA. I know this is a somewhat investing podcast, not investment advice. Do not trade SPACs in your Roth IRA. But if you're going to actively trade and you do trade in a retirement account, you don't have to worry about capital gains. So anyway, I'm doing that and I make a lot of money doing it. But I'm also posting on my anonymous burner account on Reddit, like, oh, I put my entire portfolio in Apollo warrants because they

change the background of their website from oil rigs to windmills. And I think they're going to take an EV company public. And people are like, you're retarded. This is a stupid take. And then they announce a deal with Fisker Automotive and I make like $100,000. It's like, screw you guys. It was degenerate that it was right. So and then the crazy thing is I start getting DM by other anonymous accounts. We hop on a Zoom call and it's like the CIO of a hedge fund, right? Where I'd start posting about different SPACs and seeking alpha and sponsors of these SPACs are basically. trying to get me to post about their company without telling me to post about their company. Yeah, of course. That was 2020 back in the day. Yeah. Right. Right. Right. Right. So it's like a griff without

being a grift. And I was just kind of mind blown that, oh, if you just put stuff on the internet, people resonate whether find it interesting or useful, you can just kind of, you can skip a lot of prestige or like career steps and just kind of talk to the shot collar because you have distributions. So that was the first step of, oh, internet is leverage if used in areas of money. Okay. So I, that was like basically January 2020 through August 21. August 2021 rolls around. On 24, I had made a lot of money and then lost some of that money trading stacks. I think you're underselling a lot of money because I remember, I think you wrote a blog post about this, right? You had like half a million.

I turned six grand and 400 grand trading spec warrants in nine months. And I was 23 making like 60K at the time. So like I was, I actively sandbag three different promotion opportunities because I was making more money trading stocks than I would have it work. And I had a really chill job as an analyst. But if I got promoted to a supervisor, I would have, I would have, if I got promoted a supervisor, I would have had to actually do work. So I just kept not getting promoted and saying, oh, no, like, what should I do better? When in reality, I was making 80K a week just like hitting by by by yourself. Your bosses have no idea.

Like, you're richer than them and they have no idea. No, no, they're probably thinking, like, he seems so smart. Why is he not driven? And meanwhile, I'm on Reddit, like, yo, anybody looked into this like outer space rocket ship SPAC? What do we think? Is it going to short squeeze? So that was my life, basically, during the pandemic.

Fast forward to 2021. I made money on SPACs. SPAC game stops working because if there's an easy trade for too long, everybody figures it out that stops. I think I can make a couple of big aggressive swings. I get from 400K to a million, trading just other stocks that aren't specs. Again, if you have an edge in one market, exploit it. But once that edge goes away, you can't just assume you can bet it's like going from,

oh, I was trading like S&P futures, but now I'm going to trade like wheat contracts. No, you're going to get blown up. It's not the same thing. So fast forward, I lose basically $200,000 in about a week, $150,000 of that in a day. I decided to stop trading, which is the most mature move I could have made, threw it in an index fund and I was like okay well I'm 24 I just broken up my girlfriend I knew I was moving to New York for a year for graduate school and I had like it's not like retirement money but you know if you're 24 and I'm a couple of hundred grand and you're in Georgia you're rich so oh yeah it was like

what do I actually want to do over the next year and the rational decision was well vaccine is out travels reopening travel's still really cheap because nobody really trusts going international yet, I can fly to Barcelona for $200 and stay in a hostel for $12 a night. So I called my boss and I said, I'm quitting. She said, did you take another job? And I said, no, I'm just going to Spain and explain to her that I, what I've been doing over the last year. And she said, I knew you were smarter than you were acting. I said, thank you. I appreciate that. So I end up backpacking Europe in Argentina for the next year. The writing thing really comes in a play here where I really romanticized the idea of being like,

a travel writer or working for Morning Brew or one of these media startups is their markets rider. And I felt like I had enough credibility because I'd made money trading stocks that I could actually write about what was going on in the market. Nobody wants to hire me because you don't have journalism experience. I'm just like, shut up. Like, neither does. I don't have journalism experience, but your markets person doesn't have spec trading experience.

Who's the real loser here? I was like, look, everything I've written on Reddit, Barmello-Zantany is a very credible source. So I just started writing my own substack. It was like a spite substack. I was pissed off and nobody would hire me and just started gaping on the internet. And then I was basically posting like a investing blog once or twice a week and a travel blog once or twice a week of what I was doing in Spain or Poland or whatever. And I was like, okay, well, I need to make some money. And I end up DMing a few Twitter accounts, including Liquidity, Finance Meet page. I'm sure a friend of the family.

I'm sure you know lit pretty well. Of course. Yeah, yeah. And he was like, yo, dude, I'll hire you to edit my newsletter and help sell ads. You go with like 500 bucks a week. And I said, yep, I am basically hostile hopping for the foreseeable future. That more than subsidizes my lifestyle. So I'm working for him.

My newsletter is growing quickly. We grow his newsletter from like 60K to 300kk. subscribers. I was like, this is sick. We were making tens of thousands of dollars a week in ad revenue. It was just like a really interesting exploration into how internet money works, which brings me to the LinkedIn shit posting, whatever. I used to get a lot of newsletters subscribers from Twitter. I realized that LinkedIn has three times as many people actively on it as Twitter and nobody posts. Twitter's tough to get attention because there's so many people going after eyeballs. But on LinkedIn, nobody's posting anything except for the hustle culture,

hustle grow, sales growth. Oh, it's terrible, right? It's still like that. It's terrible. Yeah, listen, if you're showing a course and running a pyramid scheme, LinkedIn is really looped for you. So I was like, huh, if I can get attention on LinkedIn, it's a way bigger audience. It's way easier to stand out on that I can use the funnel to newsletter subscribers. How do you go viral on LinkedIn. Either be cringe or satirically make fun of the cringe, which is somewhat cringe, but also funny. So I started like testing it out and I was like, okay, I should just start basically doing satirical rage bait personal finance advice on LinkedIn. I was unemployed. I was going to grad school. I didn't have to worry about getting fired for shit posting on a networking site. And I just went balls to the

wall, shit posting with the end goal being get a bigger and bigger LinkedIn following and funnel some of it to newsletter subscribers by putting, if you like this piece, check out my newsletter for more. So for about three months every day, I would add every recommended connection on LinkedIn manually until I told me I couldn't do it anymore to get the biggest, basically see the biggest following possible. And then shipposts, it would end up on people's speeds. Like none of these people knew who I was. I didn't care. Right. And, you know, like a year later, I had 40,000 LinkedIn followers on the back of just rage baiting the internet. It was awesome. I think that's where I discovered you.

So I think I started seeing your stuff from like the LinkedIn post would then go viral on Twitter. Right. I would post a screenshot on Twitter because Twitter is a smarter audience than LinkedIn. So I would post something on LinkedIn. People would freak out in the comments like you're a bad person or you should go to jail. I would post on Twitter and say LinkedIn is going crazy about this. And I would get a Twitter following from that. So it became this shit post, piss off people on LinkedIn, build following, make people on Twitter laugh.

idiots on LinkedIn, built following there. It became this flywheel of everybody laughing at like five people in my LinkedIn comment section. It was so brilliant because I remember seeing those posts on Twitter. They were going viral. And I'm like, who is this guy? And I would read yourself, like, this guy's hilarious. And then I would, you know, I would read your blog. And I'm like, this guy actually like is really, he's a really good writer.

He's introspective. Yeah. You know, he's actually as opinions. He has like a really good perspective on what it's like to be young and, you know, like, build wealth and go through like some of the, the mistakes that you made early on. So it was like a genius way where like you knew what would get you attention. And then people kind of went into the Jack Raines funnel, realized this is actually a smart guy and he like has like interesting takes.

And then, you know, now you've turned it into a full on career. I want to bring up one specific LinkedIn post. I think it's probably your claim to fame. And I think it's probably how I discovered you. The one where you've, where you hacked how to get free food in Manhattan. Right. Where you said that you would go around to every hotel and just hit the breakfast buffet and never have to pay for food.

And that post got you in trouble at your school, right, at Columbia? Yeah. So I will read the post right here. It's not too long. Please. Three years ago. For the last two months, I haven't paid for a single meal in New York City. How is that possible, you ask?

It's simple, free hotel meals. New York has 3,600 hotels, and many of those offer complimentary breakfast. By walking in and acting like you're supposed to be there, you can simply grab bacon, eggs, and toast at any Hilton or Marriott in the city. The real trick is securing free lunch or dinner. To do this, you dress up a bit nicer and head to the restaurant. Order whatever you'd like, enjoy the occasion. When the waiter comes, he's going to ask, card, credit, or charge to a room.

You say, charge to the room. Then you write down a random room number and name and make sure you leave before the payment processes. With 3,600 hotels, you can do this for 10 years without double dipping. follow me for more personal finance tips hashtag wealth hack comment comment section scam artist as a profession is short-lived wait when did you post that was that 2022 yeah 22 let's see oh my god it sounds like columbia business school is spewing out thieves and criminals these days who openly admit the wrong moons on linked end the world is so incredible i've never seen a thief so proud and then some people really like it the sort of pettiness we can get behind, especially with inflation. So some people, I think people get it.

You know, it's like, this is funny. Like, this is, this is what, you know, let's have a good time. And then, and then what, someone, someone called the dean? Like, what happened? Yeah, so somebody emailed the dean. Oh, wait, there's a funny comment here. Somebody tagged the New York City, I didn't, I missed this the first time at New York City Police Department. Cared a comment on an open admission of theft of services under NYP penal law section 165.15. Good call out. I just commented. on it right now. Three years later. Anyway, I hope that guy's doing well. He's a business tech consultant at Accenture. I'm sure he's doing great. Thank you, Matt. So somebody, somebody screenshots this,

and they send it to our dean of students, Samantha Shapsis. And I get an email from her that night and it says, hey Jack, I'm Dean Shapses, the dean of students in Columbia. I've received, I've received, I forgot how she worded it. She basically said she'd received concerning email. about my LinkedIn content from concerned parties would like me to come by her office and discuss. And I said, happy to. And I then screenshot her email and posted on Twitter and said, all right, who snitched?

And then that blew up. So Ryan Peterson, the CEO of Flexport, like multi-billionel logistics company, DMs me. He says, hey, I go, hey, Ryan. He says, so I went to Columbia Business School like 12 years ago. And I never signed the honor statement or whatever. I thought it was stupid.

He said, if they try to make you take anything down or change anything or apologize, don't do it. And if they kick you out of school over this, I'm going to hire you. And we were going to speed around the press tour with you. I was like, please kick me out of school. Like, the best thing happened in my career. I go in her office and I say, were you shitting yourself or you like, oh, my God, like what is going on?

I was kind of considered rage. I sort of considered rage baiting because I had like employment. I sort of had an employment offer on the table with a kick-ass company. And I walk in and I was like, hi, Dean Shapsis. I'm Jack. She goes, hi, Jack. I said, this has to be one of the more interesting student run-ins you have. She said, well, you appear to be one of our more interesting students.

It appears in the last month. You've not only been stealing hotel breakfast, but you got vaccinated a thousand times as a side hustle to make 100 grand. And you called Joe Biden on the cell phone. and said, you want more student loan debt and not less because you have that dog in you, and it will make you grind harder. I said, yeah, I did say all that. That's correct. She said, you're either the most socially unawares student we've ever met into the school

or a marketing genius. I said, I don't think those are mutually exclusive, but I said, I lean toward the latter. She said, this is a newsletter growth hack. I said, yeah, how does you figure it out? She said, because every time you say, if you like this, check out my newsletter for more. with a link to subscribe to your newsletter. She's like, it's pretty smart. Is it working?

I said, it is crushing. You have no idea. And once you realized that I actually wasn't committing petty theft, but I was just acting like I had. She was kind of fine with it. She said, I was like, do I need to remove Columbia stuff from my page? She said, no, just don't say anything racist or misogynistic and don't actually steal stuff. I said, okay, I can probably stay with those lights.

But that would, look what that did for you, though. That puts you on the map. You got billionaires hitting you up on the DMs and just, and I think that's like a good story right there is like you took a shot. Obviously, you put yourself out there. You did something unconventional. And I mean, you know, it maybe, you know, it was funny. Most people weren't doing that.

Most 25 year olds wouldn't do something like that. Right. And then that landed you all these different opportunities. So that kind of brings. I was going to say indirectly, you're about to hold up the book. It actually directly got me the book deal from a LinkedIn shippost. That's not hyperbole. So tell me how those dots connect.

How did you go from a LinkedIn shit post to now being a published author and getting a book deal? So I want about a year into working on my, like writing my blog, I kind of had this idea that I should write a book. At some point, I think if you call yourself a writer and you're putting out consistent content, nobody really remembers a blog poster and newsletter. People remember a book. And if you're writing long form concept, the goal is always to publish a book. I kind of knew that writing a book would suck. I underestimated how much the process would suck until doing it. But I was aware enough, even at 24, that if somebody gave me a decent book deal, I would do it.

But I probably, like, wait. I had a few different publishers reach out at different points that were, like, smaller publishing houses. But I was always waiting for, like, a Penguin Random House, Simon & Schuster, Harper Collins, to reach out. So, summer 2023, I get an email from Lydia Yadi at Portfolio, which is an imprint at Penguin Random House. She said, hey, Jack, really like your subs. back. I'm an editor at Portfolio. We'd love to chat to see if you were interested in writing a book. I said, yeah, let's chat. So we grab coffee, kind of talk through the process and start high level kicking around different book ideas. Fast forward a year later, after a couple of revisions of the proposal,

we pitched a few different houses. I actually ended up signing with her portfolio in summer of 2024. After signing the contract, I asked her, how did you even find me in the first place? She said, well, you have this LinkedIn post about getting vaccinated a thousand times that I thought was hilarious, but I also didn't know if it was actually funny or if you were just insane. And I sent in our team's Slack chat and said, is this funny or am I crazy? And a lot of the teams said, that's hilarious. And then I found your substack from that. So LinkedIn shitpost, like meme of Indian guy pushing domino, LinkedIn shitposts, but deal with people in Random House is literally how it would know. I want to learn more about the book. So, like, you know, you've talked a lot about this on your blog, right? Like, you know, experiences in your 20s. And it's kind of unconventional from what a lot of people say where it's like, hey, save all your money in your 20s because you're compounding that money and it's going to lead to, you know, more money in retirement. You kind of go a little bit different. You know, you on, you know, what you were like traveling through Europe, backpacking through Europe and your 20s? You quit your job to do all that stuff living off of what, three, 400 bucks a week? So, you know, who did you write this book for? And what are some of the, you know,

messages that you want people taken away after reading this book. So a message to all the haters when I went on Scott Galloway's podcast. If you look at the Spotify comments, everything says this guy is detached from reality and he's a Nepo baby. Unfortunately, I'm from Tifton, Georgia. I had not heard of a trust fund until I moved to New York when I was 25. I'm not a nepo baby. I did make some money trading stocks, but not enough to touch trust fund levels. I have a lot of unconventional financial advice. There's some caveats to it. If you have student loan debt, credit card debt, you have dependents who like rely on you for income, you should probably, at least from the finance, financial advice specifically ignore everything I'm about to say.

If you come from middle class or higher background and are on a good career track, even if you don't have much money saved up, if you don't have debt, I do think what I have to say is particularly useful and interesting. And the book is really geared toward college graduates of medable debt that feel this like, these competing desires for fun and adventure and risk and career accomplishment and achievement and call it like striving for a really good career. The entire point of the book is thinking through making the most of the opportunity cost of different stages of life and specifically your 20s.

I'm 29, so I can't really tell you how to live your 40s. I do think there's some universal truths to life is very stage specific. You should be thoughtful about what you want to get out of this stage in your 20s and your 30s in your 40s, when you're single, when you're married, when you have kids. But in your 20s specifically, you can have a lot of fun for not a lot of money. You have a ton of optionality. And you're flexible to do basically anything. Like older people who like your energy, you're willing to give you a shot and hire you on a whim if you've done the prep work.

You can kind of pick up and move to a new city whenever you want. You can take high-paying jobs, low-paying jobs. You can go to grad school. You just have max optionality. It's only once you get closer to 30. The stakes really start mattering. So it's not that you should join a startup or travel abroad or work for a big company. It's that you should be really aware that early adulthood, high optionality, really short window of high optionality.

How do you get the most out of a certain part of life before it's gone? For me, I wanted to go backpack Europe and was willing to forego making money doing that. But with the knowledge that, hey, I'm going to a good business school next year, realistically, most of the, the money I make is going to come from the ages of 28 plus after I lead business school, then it is 24. So if I want to do fun stuff now and it means foregoing $60,000, I need to work really hard on the backside of business school to like compensate for that lost income, but I'm only going to be 24 once. I should go do fun stuff and then figure out the money on the back end. So my kind of two pieces of personal finance advisor. One, if you don't have debt

and you don't have dependence and you have fun stuff. In Toronto, every arrival is a And nothing says it better than this. Cadillac Optic was the number one selling luxury EV in Canada for 2025. Find your rhythm across a seamless 33-inch display and an immersive 19 speaker AKG surround audio system. This city demands agility and optic delivers with precision to make every drive extraordinary. Let's take the Cadillac. Find out more at Cadillac Canada.ca. Luxury sales claim based on S&P Global Mobility Canadian New Vehicle Total Registrations for calendar year 2025 for the Cadillac definition of luxury.

I want to do, it's okay spending a higher percentage of your income and your 20s to do fun stuff and stack up memories, assuming that you are aggressively going after a career path with a high payoff. It's like you can only cut costs so much. You can always make more and more money. So be intentional about making more money over your late 20s and 30s and 40s and do the fun stuff when you're young, right? Because when you get to be 40, you're actually not going to give a shit about if you put back an extra $10,000. in your retirement accounts of 24. But if you miss out on a kick-ass trip with your friends,

you're always going to wish you took it is my general philosophy in life. That's so true, man. I mean, I'm 34 now. I have two kids. And when I look back in my 20s and I, you know, it's one of those things where I'm like,

I wish I took more risk. You know, I started doing making videos and stuff online at 29. So I kind of caught the late end of my 20s. But I think about if I was 24 in making videos, where would my career be today? And so I think you're absolutely right. When you're in your 20s,

especially if you don't have any dependence on you, like you can take so many more risk. That's why I don't really worry about like, you know, people talk about how, you know, 18 year olds are trading penny stocks or like, you know, day trading. I'm like, if you're doing that at 18, 19, 20, it's the best time to do it. You can't lose that much. Like, if all you have is $5,000 or $10,000, then you blow that, it is going to scar you. But guess what? You're not going to risk your mortgage when you're 35 because you know how that feels. Like when I was trading stocks in 24, even if I had made and lost all of it, that would have really sucked, but it just wouldn't have impacted my life that much.

And it's, I don't have that much of a desire to speculate now because I know what it feels like to make money and to lose money at high levels. It's, it's so useful to do dumb stuff when you're young so it doesn't ruin your life when you're older. I think that people don't talk about that enough. I think you're 100% right. And yeah, everyone gets like vilified. Oh, you shouldn't be, you know, doing day trading or this and that.

And to me, I'm like, if you're going to do it, do it when you're 18. do it when you're in your early 20s so you can learn the lessons from it. I'd rather have you do it then than when you're 36 and have a mortgage and then you're like, you know, buying zero day options and like, you know, gambling your Roth IRA. Don't do it then because then the consequences are so much larger. You can make up for it when you're in your 20s. So I have a hot take here. You know how Trump has rolled out?

I forgot what he called. Is it called the Trump accounts? Yeah. Trump accounts for kids. Whoever, whoever's the next president should roll out like the degenerate version of a Trump account where every 18 year old is given $1,000. to trade however they want, but they owe the government that money back, like, alone if they blow it and just like, like, like force 18 year olds to speed run the like gambler way.

Because like at the end of the day, we have, you can trade stocks. You can just lie on Robin Hood and trade options, like all the KYC stuff. Oh, yeah. I was trading. I was doing call and put options on triple levered ETFs before I had a full-time job because nobody cares, right? Oh, let me go on polymarket. That's like, or sorry, Cal's because polymarket, you can't trade in the U.S.

US, but everybody has a VPN so they can. Cali's like, oh, like, these are, you know, searching for truth. And the truth happens to be Josh Allen over under 252.252.5 passing yards. Yeah, fuck about like. So, so I'm very big of the cap of it's, we're never going to have, like, there's zero friction to speculating at this point. You should probably just like, like force-induced speculation on 18-year-olds. So they blow money and get scarred by it.

It's like exposure therapy. That's a great take, man. That's a great take. That's a great take for 2020. I mean, dude, I remember I saved up $1,000 over the summer when I was 18. I'm kind of older than you. So I opened up a Scots trade account. I immediately started trading penny stocks at 18 years old, immediately lost, or doubled the money one day, lost it all the next day, learn my lesson. And then I started doing a little bit more due diligence, lost more money.

But by the time I was like in my mid-20s, I kind of knew what to do and what not to do. It's the best lesson you can learn for a thousand bucks, a couple thousand bucks. It's like that's the best lesson at that age. And I think you're right. More people don't talk about it enough. And in fact, there's like the opposite effect where you're like, filified, oh, you should always be saving and putting away 10% for retirement. And I think that advice you start applying as you get closer to your late 20s and early 30s.

But I guess where do you draw the line, though? There has to be a line somewhere, right? Like, I guess where is the line where you don't completely go off the deep end in, you know, when you're making mistakes in your early 20s? Yeah. So it's like, I don't know. Drug addiction. Right?

Like, you should not get addicted to the cocaine and spend hundreds of thousands of dollars. That would be bad. You should probably not go 100K in credit card debt on draft kings, which does happen to people. There's probably an amount of money that's like the, you know, like there's a portfolio, efficient frontier of how to allocate your money. There's probably an efficient frontier of dollars lost to speculation at like 21. That's good.

And if it's below that, you don't quite do it enough. And if it's above that, you risk ruining your life. Maybe it's $7,852 when you're in college. I don't know. I'm just like making stuff up. I don't know what the line is. But yeah, I like, and I do not know how you find that. I do think in general having like minor financial setbacks from your own youthful

stupidity is very useful for preventing you from having catastrophic setbacks from financial stupidity when like you have kids. 100%. And look, a lot of our audience is younger. A lot of people that listen to the show are in college. I think this book is a fantastic week for them. Jack, if I'm being perfectly honest, I haven't read it yet, but I have read your other writing, right, and you're a fantastic writer, so that's the other thing. Not only is there a lot of, I'm sure a lot of good stories in here, but like Jack's

writing style, I really like it. So I think if you're in your 20s right now, you're going to like reading this book. You're probably going to take away a lot from it. I want to end with this question. Like, just the writing process. I mean, what does it take to write what is like a country? couple hundred page book. Like what, what is that take? Are you grinding away? Um, like, is it like a, do you grind for a week and then take a break? Do you just go grind for a three

months? Like, what does it take to write like a long book like this? Um, well, you just open Claude and say, write a six thousand more book, make no mistakes. Here's my blog. No, no, what's, I would say what's funny about the whole, the whole book writing thing. I did not realize how many, like, bestselling books are written by Ghost Rider in the nonfiction space until getting in here. So really? Yeah, like 70% of nonfiction books either use or heavily rely on a ghost writer. So there's the people I know who've actually written their own books, I have like a ton of respect for it. To be clear, I wrote my own book. There was no ghostwriter or AI involved. Okay, good to know. But anyway, for people who have gone through the process themselves and for all

the ghost riders in the background, keeping the industry going, kudos to you, writing a book is hard. actual process. I signed this deal in September of 24. I was then recruiting pretty heavily to try to switch jobs that fall. So it didn't really start working on the book until February. I joined Slow, the venture fund I'm at in January of 25. I moved to San Francisco for a year. So that February, I was like, okay, I have to write a book. I have published about a million words online and blog form. A blog is about 2,000 words. The book is. A book is. 60,000 words. I thought it was just going to be writing 30 blogs. It's actually more like writing 300 blogs because the complexity scales like exponentially with length of book because all of a sudden everything has to connect. And this sounds really good standalone, but it doesn't flow well with the rest of the book. And I basically was grinding on it. I would get off work on Friday and I try to write before and after work. But I write better when I have like a six hour block where I can just crank on words, at least when working on a book. And the only way to

do that was just Friday through Sunday nonstop. So I do that every weekend for five months. Oh my God. I'm reading the manuscript and I hate the whole thing. I'm like, oh my God. And I owe the first draft on July 1st to Penguin. And I was supposed to go on vacation with a couple of buddies to Spain for like a week and a half. The day before, I bailed on the trip and I locked myself in a hotel room in the Citizen M and the Bowery in New York and just like didn't leave until I was pretty happy with the first draft. I wrote, I think, I think I wrote a combined 42,000 words in 13 days. I lost 15 pounds. And I just like, oh my God. It was, it was like pretty traumatic. It was, it was a very good forcing function to get it done, though,

because when you get a book advance, you owe them a manuscript. If you don't turn it in, they've already given you some of the money and they can claw the money back. So I was, shoot, I have to get this pressure. Yeah. So get that turned in. I get the book back. after a month and a half and I was like, I still hate this. But it's much easier when you have a full manuscript that you don't like to then edit, revise, restructure until you like it, than it is going from blank page to shitty manuscript. And you have to go through that process. Like every other author I've talked to is that a similar, you write a chapter, you hate it. And then you get all the chapters that you hate together. You have a manuscript that you hate.

And you edit it one time and it's like fine. And then after several rounds of that, you end up with a book that you're excited to publish. And for me, it was like, Like the whole spring was just trying to get that first thing done. Finally, I have something serviceable. And then August through December was getting it to the point that I wanted to take it public. And like now I'm very happy with the book and judging from Instagram, DMs, emails, Twitter. Other people seem to like it a lot too, which is good. Writing a book sucks.

You got Morgan Housel. Dude, you got Morgan Housel on the bag giving you a goat. He's been on the podcast, by the way. So Morgan Housel is even giving it a thumbs up. And yeah, I mean, look, I'm really excited to dive into the book. I'm going to read it over the next couple days. And I just wonder what that process is like because like, I mean, I've thought about writing a book myself, but I think I'm going to stick to kids books. If I ever do write a book, it's just going to be like a 10 page kids books so my kids can read it.

I don't know if I can ever do like a 40,000 work. I also, I tried every shortcut on this because it sucks so bad that I try to do the, oh, well, typing nonstop sucks. Can I get the first draft or at least like rough draft chapter ideas out using whisper flow or like a voice of text thing? But for getting scrambled notes out from email, it's fine. If we're writing a book because so much of the writing process is you're mid-sentence and it pulls you to another idea, you can talk faster than you can think. Therefore, the voice to text actually just doesn't work it off in book drafts. So eventually, I realized the only way to do it is I have to sit in a room and put my phone in a box and just write for six hours. And then you get food, you sit back down, and you write for another six hours, and you go to sleep.

And that was kind of dead for... several months. That's brutal. Well, I mean, look, I'm happy that you did it, though, because, I mean, I think a lot of people are going to get some value out of this. And when's the sequel coming out? I don't know. Ask me a year. 39. When you're 39, you got to be 30 years. I'll do one at the end of every decade until I die. Oh, man. That's actually a great idea. That's a great idea. This is sign you up for that right now. Jack, I'm so happy we did this, man. I'm so happy you came on. We got a chance to do this. And is there anything else you want to plug? So listen, Young Money, that's the name of the book, Young Money, a field guide to wealth of purpose in your 20s. A substack newsletter, also Young Money. You can follow me on any social media. I have a cowboy hat on and my profile picture across all platforms.

So Young Money is the book and the newsletter. Jack Raines is my name on basically everything. That's awesome. I'm surprised Lil Wayne hasn't reached out to- So I, you know, I wasn't doing with this. I was like, can I get sued for this? And apparently copyrights and trademarks work in different verticals, but a record label can't press charges against a book title.

And also book titles can't press charges against other book titles. Kevin Ruse from the New York Times had a book called Young Money like 10 years ago about Day in the Life of Investment Banking Analyst. Turns out that multiple people can use the same book title. So somebody else can write Young Money next year. It's totally five. Okay, that's good to know. Yeah.

Maybe we'll get one of the low-way. Yeah, for your children's book, you can call it Young Money. I'm going to call it Young Money. Oh, Younger Money or something like that. Youngest money. Yeah, exactly. Well, look, guys, this is on Amazon and I'm sure all the books are as well. Yeah, every buy books.

Awesome. That sounds good, man. I appreciate it again. And we'll have you on in 10 years to do that part two. Can't wait for the sequel. Yes, sir. Appreciate it, Jack. Well, all right, guys.

Hope you enjoyed that conversation with Jack Rains. I thought that was a super fun one. It was just great talking to Jack and hearing. about his backstory. I'm still working my way through his book. I'm about a third of the way through, and yeah, I think it's a great read for someone in their 20s. Let me know what you guys thought about today's conversation, and do you want more casual interviews like that? Drop your thoughts on Spotify and YouTube. And why you're at it, consider giving us a five-star rating as well. You know, all that engagement really does help us out and it helps other people find the show. Thank you guys so

much for listening, watching, and commenting. Shout out to Mike for all the work behind the scenes. And we'll see you guys back here on Tuesday.