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

Zaid Admani (0:00)

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 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 of 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.

Jack Raines (1:12)

Zaid, thanks for having me. I like the accolades you gave me. Professional shit poster, way better than author, VC or anything else.

Zaid Admani (1:20)

I mean, dude, it's true though. That's kind of how you burst onto the scenes. I don't want to start it there. 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. 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 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, a new book out, Young Money, and you work for a VC from Slow Ventures. How did all that happen?

Jack Raines (1:59)

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 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, 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 methods of the madness, but it's fun to fuck around with the internet. People seriously underestimate it.

Zaid Admani (2:54)

So kind of walk me through.

So you just graduated college, 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 you just always had this side thing that you were passionate about. For you, it was writing online, you had a blog that you started. And then just from there, when did you start getting traction? And when did you know that the best way to growth hack your blog was just to write funny stuff on LinkedIn, triggering a lot of people?

Jack Raines (3:21)

So to take a step back, I had a burner Reddit account called Barmelo Zanthony in 2020 And it was like a play on words for Carmelo and Anthony and Zadak's Bar. My entire fraternity chat had edgy drug related names, nicknames in our group. And I made that my Reddit name, and the picture was one of the thumb 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 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'd by other anonymous accounts. We hop on a Zoom call and it's like the CIO of a hedge fund, where I 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 because that might be illegal.