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. And 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 SPACs 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 [__] poster. He's now a published author. Jack, welcome to the Rundown.
Zade, thanks for having me. I like the accolades you gave me. Professional [__] poster, way better than author, VC, or anything else. So...
I mean, dude, it's true though. You are... That's kind of how you burst onto the scene. And I kind of want to start it there.
Okay. I mean, look, this is why I love your story, man. I've been a 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 how you 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 [__] posting online. And then now you're again a published author, new book out, Young Money, and you work for a VC firm, Slow Ventures. 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 and realize, oh, I should be a thought leader or build a personal brand. I 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. Um, but no, I mean, I was very addicted to posting. And it turns out if you're opinionated on the internet, but 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 method to the madness, but it's just fun to [__] around with the internet. People seriously underestimate it.
So, like, kind of walk me through. So, like, 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. Like, so for you it was what, 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 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 Barlo Anthony in 2020, and it was like a play on words for Carmelo Anthony and Xanax bar. My entire fraternity chat had like edgy, drug-related nicknames in our GroupMe, and I made that my Reddit name, and the picture was one of the thumbs or whatever from Spy Kids.
So COVID hits, like a lot of other 22, 23-year-old guys, I was working remote, corporate finance, really bored, and I started trading SPACs. 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 changed 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 [__], this is a stupid take. And then they announced a deal with Fisker Automotive and I make like $100,000. It's like, screw you guys. It was degenerate, but it was right. So, and then the crazy thing is I start getting DM'd by other anonymous accounts and we hop on a Zoom call and it's like the CIO of a hedge fund, right? Where I start posting about different SPACs on 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 because...
That was 2020 back in the day. Yeah.
Right. So it's like a grift without it being a grift. And I was just kind of mind blown that, oh, if you just put stuff on the internet people resonate with or 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 caller because you have distribution. So that was the first step of, oh, internet is leverage if used in areas with money. Okay. So that was like basically January 2020 through August 2021. August 2021 rolls around. I'm 24. I had made a lot of money and then lost some of that money trading SPACs.
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. Are you comfortable saying that?
I turned six grand into 400 grand trading SPAC warrants in nine months, and I was 23 making like 60k at the time. So like I actively sandbagged three different promotion opportunities because I was making more money trading stocks than I would have at work. And I had a really chill job as an analyst, but if I got promoted to 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 buy, buy, buy.
And 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? Like, 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. It 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 SPACs. Again, if you have an edge in one market, exploit it. But once that edge goes away, you can't just assume you can. Then 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. 150k 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 broke up with 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 have a couple of hundred grand and you're in Georgia, you're rich.' So...
It was like, what do I actually want to do over the next year? And the rational decision was, well, vaccine is out, travel's 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 bucks a night. So I called my boss and I said, 'I'm quitting.' And she said, 'Did you take another job?' And I said, 'No, I'm just going to Spain.' And explained to her what I've been doing over the last year. She said, 'I knew you were smarter than you were acting.' I said, 'Thank you, and I appreciate that.' So I end up backpacking Europe and Argentina for the next year. Um, the writing thing really comes into play here where I had really romanticized the idea of being like a travel writer or working for Morning Brew or one of these media startups as their markets writer. 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 SPAC trading experience. So who's the real loser here? I was like, look, everything I've written on Reddit, Barlo's Anthony is a very credible source. So I just started writing my own Substack. It was like a spite Substack. I was pissed off that nobody would hire me and just started yapping on the internet. And then I was basically posting like an 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 Lliquidty Finance page. Sure. A friend of the family. I'm sure you know Lit pretty well.
Of course, I know him. Yeah.
And he was like, 'Yo, dude, I'll hire you to edit my newsletter and help sell ads. Are you good with like 500 bucks a week?' And I said, 'Yep.' I am basically hostel 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 300k 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. Um, which brings me to the LinkedIn shitposting, whatever. I used to get a lot of newsletter 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, hustlebro sales.
It's terrible, right? It's still like that. It's terrible.
Yeah. Listen, if you're shilling a course and running a pyramid scheme, LinkedIn is really lucrative for you. So I was like, huh, if I can get attention on LinkedIn, it's a way bigger audience that's way easier to stand out on that I can use to 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 ragebait personal finance advice on LinkedIn.' I was unemployed. I was going to grad school. I didn't have to worry about getting fired for [__] posting on a networking site. And I just went balls to the wall [__] 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 they told me I couldn't do it anymore to get the biggest following possible and then shitpost so it would end up on people's feeds. Like none of these people knew who I was. I didn't care.
And you know, like a year later, I had 40,000 LinkedIn followers on the back of just ragebaiting the internet. It was awesome.
I think that's where I discovered you. I think I started seeing your stuff from like the LinkedIn post would then go viral on Twitter. So...
I would post on Twitter because Twitter has 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 [__] post, piss off people on LinkedIn, build following, make people on Twitter laugh at the idiots on LinkedIn, build 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 your stuff like, this guy's hilarious. Then I would, you know, I would read your blog and I'm like, this guy actually is a really good writer.
Yeah. You know, he actually has opinions. He has like a really good perspective on what it's like to be young and, you know, build wealth and go through some of the mistakes that you made early on. So it was like a genius way where 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 has interesting takes, and then 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 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.
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. #wealthhack. Comment section: 'Scam artist is a profession that is short-lived.'
Wait, when did you post that? Was that 2022?
Yeah, 2022. Let's see. Oh my god. 'It sounds like Columbia Business School is spewing out thieves and criminals these days who openly admit their wrongdoings on LinkedIn. 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 actually...
I think people get it. You know, it's like this is funny. Like this is, you know, let's have a good time. And then what? 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 missed this the first time. 'At New York City Police Department, care to comment on an open admission of theft of services under NY Penal Law section 165.15?' Um, good call out. I just commented on it right now.
Um, anyway, I hope that guy's doing well. He's a business tech consultant at Accenture.
Oh, I'm sure he's doing great.
Thank you, Matt. So 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 Shapsis, Dean of Students at Columbia. I've received...' I forgot how she worded it. She basically said she'd received concerning emails about my LinkedIn content from concerned parties that would like me to come by her office and discuss. And I said, 'Happy.' 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-billion dollar 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're going to speedrun the press tour with you.' I was like, 'Oh my god, please kick me out of school.' Like, best thing to happen in my career. I go in her office and I say...
Were you [__] yourself? Were you like, 'Oh my god, like what is going on? LinkedIn got me here.' I sort of considered ragebaiting because I had like 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 that 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 a hundred grand. And you called Joe Biden on his 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 unaware student we've ever met into this school or a marketing genius.' And I said, 'I don't think those are mutually exclusive.' But I said, 'I lean toward the latter.' And she said, 'This is a newsletter growth hack.' I said, 'Yeah, how'd 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.' Um, and once she realized that I actually wasn't committing petty theft, but I was just acting like I had, she was kind of fine with it. I was like, 'Do I need to remove Columbia's 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 within those lines.'
But that mean that like, look what that did for you though. Like that put you on the map. You got billionaires hitting you up on the DMs. 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, maybe, you know, it was funny. Most people weren't doing that. Most 25-year-olds wouldn't do something like that. And then that landed you all these different opportunities. That kind of brings...
I was going to say, in direct, indirect... You're about to hold up the book. It actually directly got me the book deal from a LinkedIn [__] post. That's not hyperbole.
