We just raised a $63 million fund to invest directly in creator-led businesses.
This is Jack Raines, a successful writer and content creator with over 170,000 followers across platforms. He's the creator of Young Money, a newsletter that gets over a million views each year, where he shares insights on money, work, and life's big questions. In this episode, we'll cover why writing is important to businesses.
I think it's incredibly important. It's one of those things where you're going to see a bigger gap between people who do and don't write, such as people who can and can't write. The secret sauce on how anyone can become successful in any industry. And the sweet spot is when the thing that you're doing for money, you also just have some level of interest and enjoyment from where you go down the rabbit holes of the thing that pays you. It's not a bad way to live.
What will the creator economy look like in the next five years?
I think that we're going to see a lot more.
How will AI impact writing and content creation?
I think we're going to see a lot of people that just become increasingly reliant on outsourcing too much of the writing, such as the thinking process, to a robot. I think that people are overestimating how much AI discounts the value of really human things.
And what's the best platform to start creating online? According to Jack, I think that the most valuable one is probably... You have it. That is why I...
If somebody asks you what you do for a living, what do you typically tell them?
Yeah, that's a good question. So it depends on who asked and what the context is. The answers range from being really pretentious and saying that I'm a venture capitalist, which is really fun. Like, I've been able to do that for about four weeks now, to saying I'm a blogger. I used to say I shitpost on the internet, but typically, if you say that I'm a writer or I work for a venture fund and then kind of go from there, because those are both true. But I don't know. It depends on which kind of image you're trying to convey on the first impression.
But when you were in school, though, you got a finance degree or was it journalism? Were you writing then? Like, was your background...
Yeah, undergrad was finance and Spanish. So I kind of was just typical go to finance after graduation. The basic setup was graduated undergrad in 2019 from Mercer University with degrees in finance and Spanish. I'd gotten into business school at Columbia. They had like a two plus two deferred enrollment program where if you got accepted, you then work like two to five years before starting your MBA. So I knew I was going to go to CBS in like 2022-ish. So I figured just like work in finance for a few years, go to Columbia, and then work in like big boy finance, like investment banking, basically any place that wouldn't recruit out of Mercer University, which is probably banking or consulting, then do that after business school. That obviously is not what ended up happening at all. So I did end up coming back to the finance route. But yeah, I never studied journalism, just started blogging as a non-professional journalist.
When did you start, let's say, your professional career? That was like prior to 2020, prior to Covid, January or February 2020?
So I graduated December 2019 and then I was working in corporate finance, like for UPS, shipping company, and I was in the office for like four days. And then the pandemic hit and they're like, all right, we're going remote for two weeks. Two weeks obviously turned into two years, as everyone knows. So yeah, I mean, great timing to start your career.
Were you already posting, we'll say, on Twitter and LinkedIn when you were in school and coming out and like starting to look for jobs, or was this something you started taking that like... And when I say that, I mean, like legitimately just like writing down everything, right? Like, did you start doing that after you graduated, or had you already started and built a little bit of a following when you were in school?
So the shitposting specifically probably started Q1 2021. I don't know why. Like I actually went back and checked because I was curious too. I can remember when I actually started doing that, because I remember when I started doing it like intentionally with like a purpose, trying to funnel more people to my newsletter. But I was just doing it for the love of the game, like while I still was working at UPS. Like I did at least like four or five shitposts while I was like fully employed and didn't really have any bigger like writing growth ambitions. I just thought it was funny.
What does your employer say then? Were you ever concerned at that point? Because like, I feel like you go back, I don't know, maybe ten, fifteen years, and like being on social media is like so taboo with like employers, right? And you're like, were you ever worried about that?
No. But the caveat to that is I had already like planned to quit my job sometime summer 2021. Like basically, we can get into this a little bit, but I had a very fortuitous run on the stock market during the pandemic, and knowing that I was going to go to business school in fall 2022, then having a lot more money than a 23, 24-year-old should have. And like Q1, Q2 of 2021, I kind of knew that sometime around August, I was probably gonna quit my job. Like I wanted to travel and just go do more interesting stuff than work on like UPS's 2026 profit plan. So like, I already kind of knew I was going to leave, so I wasn't really that concerned with anything like that. Like it probably should have been more concerned about, you know, your parents always tell you the internet is forever. Be careful what you put out there. But I just thought it was very funny making fun of hustle culture on LinkedIn. So now I did have my boss tell me one time that she thought one of the posts was hysterical. Like it rarely got mentioned and it never got brought up as an issue. And there was just one specifically where she was like, this is pretty funny. Which then like gave me a lot more courage to keep doing it.
Definitely like incentivizing confidence to be like, okay, I'm getting that confidence. Yes. So yeah. All right. So let's talk about this fortuitous run on the stock market. Like, so what were you trading? You were just day trading or like what led to, I guess, you having success in the stock market?
Yeah. So I was going back to like February 2020, like right when the pandemic really hits, market starts going down, shoots back up, going down. I, like every other 22-year-old dude, had been spending a little bit too much time on Reddit and Wall Street Bets, and initially it was literally just buying SPY puts. Market tanked, thought I was a genius. Then the market recovered, realized I wasn't a genius because I bought more puts and basically lost the money that I made. So sitting there, like with my kind of tail tucked between my legs, thinking, all right, like I'm not doing that again. Like I made and lost like $15,000 up and down over the period of a month. That hurt. And then I saw that DraftKings was going public through this thing called a SPAC. Funny enough, your cousin Jake actually was the one who was like, dude, you can buy DraftKings stock before it actually goes public. Check this out. I didn't really know what he was talking about. I thought he had something totally misconstrued because he's not really a finance guy. He was actually 100% correct in this case. So I look into it and I'm like, oh, this is interesting. It's like a weird IPO vehicle. And long story short, like the DraftKings stock did very well. And all of these companies that went public through SPACs also had warrants that were effectively call options. Like if you basically buy them, they're going to go up, and if the stock doubles, the warrants are going to go up like five to seven x. So without like, I can talk like 30 minutes just on this. I'm not going to deep in the details. I got very good at figuring out which SPACs were going to blow up before they blew up, effectively. And like at one point, it parlayed six grand in my retirement account into 400 grand, like nine months. And then that bubble popped. And then I just like kept trying to trade stocks. And then I ended up losing like half of that, which wasn't great, but still went from six K to like close to 200 K in about a year and a half. Wasn't bad. I was pretty happy with the performance.
And then pretty good track record.
Yeah, it's not bad. There was one point where my dad and uncle were like considering giving me some like family money to invest because I'd made so much, and that just would have... I mean, that should have been a screaming top signal, like just throw this thing in the S&P, which is what I should have done at 400. But, you know, you live and you learn.
It's funny, you did well on all these SPACs, yet you're very also critical of the, I don't know if you call it the SPAC king, but Chamath.
Chamath. Oh, total grifter. I mean, yeah, like horrible, horrible person. I don't know him, so I can't call him a horrible person, but like what he did to make money off of that stuff was like it was a grift. Maybe he's a great person.
And this was just like, explain that. Explain what Chamath was doing to make money off the SPACs.
The way that it works is like, if you're the SPAC sponsor, you put up some nominal amount of money upfront, like it's not a ton, but you then raise money from investors to fund a SPAC, which is effectively a bank account that's just like a publicly traded bank account, effectively. They have like $100 million in them. And that SPAC exists to go find a private company that wants to go public. And you say, hey, instead of like taking a year to do like this whole IPO roadshow, paying these banks all this money to underwrite the deal, like just work with us or with the bank. It'll be faster, it'll be quicker. We'll give you $100 million for, say, 10% of your company, valuing the company at a billion. And then you'll go public. The SPAC shares just change, and it's like the SPAC shares then become that other company. It's like DraftKings. The SPAC told DraftKings they wanted to take them public. The existing DraftKings shareholders then own like 80 or 90% of the stock. The SPAC shareholders own the rest, and those shares unlock like, say, after six months or a year. And they're all publicly traded. If you're the sponsor, you get a ton of free shares for like a nominal, we'll call it like $25,000 or whatever their fee. Yeah. And like sometimes the sponsors might put in more money, like a pay-to-play deal. But long story short, he took like seven or eight companies public through SPACs. He had gotten a big Twitter following and he would tweet like, called them his one-pagers. But it was a screenshot of a Word doc with like his write-up on these companies, like why they're worth much less than that. And like 14 out of 15 of the SPACs he was involved with were down at least like 80% from the SPAC price. Now, a couple of them have bounced back, but the majority of them are down horrendous. And like Virgin Galactic, he used to pump it on Twitter all the time. And then he like quietly dumped like everything and then put out this tweet about how he had to manage his liquidity after saying that like he was in it for the long haul. And like again, there's nothing wrong with anybody like selling, as long as you're not like straight up pumping a thing saying I'm in it forever, which I think he was, and selling it. Like people can sell stuff whenever, insiders sell all the time, whatever. Like he took them public. He was in it for a couple years. But when you're actively pumping your SPACs on Twitter and then you're getting like free shares from it, and you're getting a lot of like retail interest to buy it, the price doubles, you get your free shares, you exit all your positions. And then it turns out all these companies are just trash. Like most of them had no business being public. Unprofitable, like growth was very coveted, inflated, and it wasn't sustainable. Yeah. I mean, you're basically just transferring money from your Twitter following to you, and it works. Like he probably made $1 billion off of like the SPAC boom in a two-year period. But none of that or very little of that value had like any staying power, because it just wasn't... those companies weren't real for the most part.
I think one of the biggest things regarding that, though, too, is just like the value of, and maybe even the responsibility too, of having a big following, especially in the industry. So like I guess talking about your, you know, following and kind of what you've built, let's go back to that for a minute. So like if you were to look back and kind of, you know, the last five, six or seven years, however long it's taken you to kind of, we'll call it, build relevancy on the internet, right? How did that start and when did you start like gaining that relevancy and like realizing that like, hey, I'm on to something here?
Yeah. So I remember it was, I mean, it was probably right around the time the whole SPAC trading thing started. I had a burner Reddit account called Marshmallow Anthony. And if you're familiar with the meme of like the massive naked black guy, you know who I'm talking about, sitting on the edge of the bed. Yeah, yeah. So that was like my picture on there. Like the whole thing was a bit. But I was one of the moderators and like co-founders of the SPAC subreddit, and that thing blew up because so many people were interested in SPACs where like I was publishing on my burner account, like deep dives on all these SPACs that like I was looking at or trading. And I mean, it wasn't like the same thing as when you read like a sell-side equity research report on a publicly traded stock. It was like, hey, Apollo SPAC website has changed their background header from oil rigs to windmills. Like that probably means they're going to take an electric vehicle or like green energy company public. I was right, like I was a month early, but they announced a deal with Fisker Automotive, like stuff like that, like very niche stuff. And I got a pretty big following on Reddit from that. And then I was like, okay, this is like very interesting how you can disseminate information so quickly through the internet, like how people really like buy in and lock in the stuff. And that subreddit now has like 200,000 followers or whatever.
Are you still pretty active in there?
No, I mean, like SPACs are dead. I actually think they're going to make a comeback. Like I've seen there's been a couple of SPAC issuances over the last year or two, but like it kind of fell off in like 2022. But I had that. And then around summer 2021, I realized that this website Seeking Alpha would pay you like decent money, like 100, 200 bucks a pop to do like different stock write-ups. And I was essentially just like repurposing the stuff I was putting on Reddit and putting it on there, but just like making it a little cleaner or more official. And I got like a decent following on there from just like finance pros. But the thing that really made it, like where I really started getting a following, was after I quit my job in August 2021, I ended up reaching out to this finance meme page called Liquidity, seeing if he needed help. It was a newsletter, he had like a finance newsletter with like probably 100,000 subscribers at that time. And he basically hired me to like edit the newsletter every day and do some random like bizarre stuff. So from that and like seeing, once I saw the business side of what he was doing and how much money he was making from ad revenue and stuff, I was like, okay, my initial plan of go to business school, go to banking, whatever, that's absolutely stupid. Like there's so many more interesting ways to like leverage the internet to make money, especially if you have some level of distribution that I should like be doubling and tripling down on, like building a newsletter. And luckily I just enjoyed writing and had a lot of thoughts that I wanted to put out on the internet where like it was... it's not that I was already writing on like a regular weekly cadence for fun, but it was... there was like no... it was not difficult at all for me to start doing that. Like it was something I enjoyed doing. So yeah, I started blogging a lot, like starting a Substack. I was writing like putting out one or two blog posts a week, and then I got very, very loud and active on Twitter through that. Or like anybody who I thought was interesting, I was always in their replies, talking about stuff. Like Twitter just felt like such a cool... it was kind of like the lunchroom where like in high school where like there's so many different conversations going on. If you just walk by and overhear something interesting, you can jump in. And it was crazy how much of like an equalizer it was, where again, Twitter isn't as useful now. Like it's still very valuable in that like I have a lot of relationships from it. Twitter from like a direct messaging perspective is still where like there's a lot of cool stuff happening. But at that time it was just very like people who you had no business knowing or talking to who were just like in either totally different domains or like seven steps ahead of you in your domain. If you were tweeting thoughtful stuff, like you were engaging with these people who are worth like hundreds of millions of dollars, sold companies. And it was just cool. So I was like, all right, well, this seems like the best way to one, like get to know interesting people online, funnel some of this traffic back to the newsletter. Like it was... I was just having fun yapping on the internet and then people liked what I had to say, signed up for my newsletter. And it was kind of a cool flywheel for a couple of years.
