He Spent His 20s Exploiting Optionality. He's Doubling Down. | Jack Raines on Knowing When to Commit

I would say I spent most of my 20s exploiting optionality and did a good job of it and now it's like I'm transitioning to call the shots you want to double down on. Being from South Georgia, not knowing anybody in the Northeast at that time, I like didn't really understand the initial career outcome gap between going to like a Mercer University and a Yale. You just when you're not from call it a big city and you haven't known people that have gone to those schools or who have like optimized for that from a young age, you just don't know. And I turned 10 grand into like 33 grand. And I was just going in the handicap stall in the bathroom in the beginning of work every day and just watching the market open. It was freaking euphoric. It was awesome. And I loved it. Long story short, I lost like $160,000 in a day. And that like 5 seconds of watching my portfolio get eviscerated was the greatest lesson in behavioral finance that I will ever learn.

He paints the entire interior of his classroom like a map from the Middle Ages. It's, you know, you have these normal like whitewashed walls. No, it's like Lawrence of Arabia, Saudi Arabia, Egypt, the Levant, all the way over to like modern day Pakistan and up to like Istanbul, right? And in our world history class, basically every month we would go like all in on a random period of history, but he would focus on one or two protagonists from that period of history. And it's just not the stuff you would get from a normal history class. If you're just like reading the Wikipedia highlights, it's this country conquered that country and this happened and that happened. But no, like every single thing was driven by some guy who wanted to do something and he just decided to do it. And his motivations for doing that were either driven largely by like insecurity, money, or sex. And that's kind of like the entirety of human history is sort of one of those three things. You either want more money, you want more sex, or you just want to be better than the people around you.

I'm much more interested in writing a book that compounds over 5, 10, 15 years and something that's a flash in the pan for 2 months after launch and nobody cares.

I mean, that's the best intro I think I've ever gotten on a show. Matt, also the ad read with like the piece of paper is so good.

So good. So good.

So, let's honestly let's go in the order that you listed them. We should hit all of them.

So, to turn back the clock, there were a lot of bubbles in 2020. My favorite bubble was the SPAC bubble. I didn't play GameStop. I did not really play crypto. I did play SPACs and had a blast. I had a Reddit account for a couple years where I was not really a poster. I was more of a lurker called Carmelo's Anthony, a play on words for Xanax bar and Carmelo Anthony. That was a stayover for my college fraternity GroupMe group chat. And I was an avid acolyte of Wall Street Bets like many people were, except instead of chasing Tesla and I think Tesla, Virgin Galactic, what else were the hot ones back then? It was like the two big names in like Q4 2019, early 2020. COVID hits, I make some money shorting the market. I think I'm a genius. I was 22. I just graduated college in December 2019 and just like opened a Robinhood account, bought a bunch of SPY puts. I then lost all the money I made because I bought more puts and the market recovered because guess what? Markets tend to recover and the S&P was actually not going to zero even though Bill Ackman cried on TV and said it was okay. So, I think I'm never going to trade again. And then one of my buddies texted me about this thing called a SPAC. He said, 'Do you know what a SPAC is?' I did not know what a SPAC was. He said, 'I don't either, but if you buy this thing called Diamond Eagle Acquisition Corporation, you'll then own DraftKings stock.' And everybody I know is betting on like Korean digital ping pong or whatever people were betting on during when like sports got shut down. There were all these like weird niche like digital gaming sports betting markets that were popping up on DraftKings and FanDuel. And he was like, this thing is going to rip. And then everybody's going to be gambling on like the NBA bubble games and all this. And it was actually he was totally right. DraftKings ended up 4x-ing. Like it was a pretty astute thesis. But I was more interested in what is a SPAC and I look into it. SPACs are obviously like an alternative IPO vehicle basically. And I was really interested in SPAC warrants. I had made money trading options. I lost money trading options. The reason I lost money trading options was because time decay can really mess you up if you're buying like weekly and monthly options and then the market moves against you for a few days. SPAC warrants, they don't expire for 5 years. So I could basically get the same leveraged bet without having time work against me. And the math was basically if I think a SPAC will meme and it hasn't memed yet, I'm going to buy the warrants and you sell the pump. And I was pretty good at figuring out which SPACs are going to rip early and then I would sell them every time the chairman of said SPAC was on Jim Cramer's show. It got more specific than that. For example, Apollo took Fisker Automotive public through a SPAC. I front ran that deal because I saw that Apollo had changed their website background on their SPAC site from oil rigs to windmills. So I figured an EV deal was coming. I posted on Reddit under Carmelo's Anthony that I think the post said yolo Apollo SPAC warrants because of website change and people in the comments like you're [__] and then I made like 5x my money two weeks later and I said autism pays or something like that. Anyway, that was basically how it went.

Now, getting on to the, you're asking who else is trading. So, I co-founded the SPAC subreddit and now it has like 300,000 followers. I think it's sort of dead now because nobody cares about SPACs anymore, even though they are sort of back. I actually have some SPAC warrants right now in a battery data center play that's going public through a SPAC. But there was like a subset of people in this subreddit who actually seemed to know what they were doing or were making money. And one of the guys DM'd me said, 'Hey, we're making a Discord for people who actually know what they're talking about.' I said, 'Okay, me as a 22, 23-year-old dude in Atlanta, Georgia absolutely knew what I was talking about.' So, I get added to this. Don't know any of these guys' real names. I connect with some of them on Twitter. A few of them are, there's an SPAC man who made several million dollars on a company called AST SpaceMobile which I still think is total vaporware but has done really well because SpaceX comp. SPAC Attack who made a lot of money and I don't know any of these guys' names in real life, right? But there's probably 50 of us in this Discord chat and the guys who had computer science backgrounds are building like bots, like push notification bots through Discord. So we kind of have this like online fraternity of people from all over the world who for some reason decided we're going to make bank trading SPACs. It gets really funny where fast forward 6 months, I'm in I think I was in either London or Barcelona and just meet some dude and he's like, yo, SPAC Attack is my best friend from high school. He's like, I recognize your face from Twitter or something. And there's been over the last like five years I've had just like, I had a guy come up to me at a bar a few months ago. He's like, 'You're the SPAC guy, right?' And at this point in my life, like I get recognized for a lot of random stuff. It's usually, 'Oh, I liked your book or this or that.' But like to this day, 5 years later, I still get recognized by random people as you're the SPAC trading guy or like I remember your call on Lucid Motors or whatever, which makes it really funny.

But it's interesting because there's definitely little sub communities and subcults online right now. Like once you see all this play out once, you realize it's not going away. And one of my bigger takes on markets is I actually think cycles and the bubbles will just play out faster and faster and faster because the speed of communicating information and like coordination among people has dropped to zero where every pump and dump is going to get speedrun. Every like sensational bubble about any particular sector. The time it takes for like one person's thesis to become consensus with a subset of people is basically zero now. So, it's funny being in one of these like trading cults for basically a year because you kind of just really get to tap into the psychology of like what is not an insignificant part of market participation. Like a lot of times the marginal buyer or seller is coming from a Discord chat. And you could think that sounds crazy particularly if you know you are a like Benjamin Graham disciple but at the end of the day that is in the short and medium term what it's basically Discord chats and pod shops driving like marginal buying and selling action in like when the market's really volatile. I say all that to say I don't know any of the other traders from that SPAC game. I know none of their real names. We would hop on voice calls, like 20 of us, and just riff. Like it was like a really funny internet chat room. Like it reminded me of playing like Xbox Live back in the day with a bunch of internet strangers who I didn't know in real life, but we were making and losing tens and hundreds of thousands of dollars and it was awesome.

So kind of, I mean, so I had this professor, I never actually took a real class for him but I did an independent study with him. I got my MBA from Columbia Business School, graduated 2024, and Professor Dan Wang, he was a big fan of my LinkedIn. So, a few years ago, I was trying to get more and more subscribers on my newsletter, right? Like I had a Substack newsletter, 20 or 30,000 subscribers. I was basically blogging about everything from financial markets to like introspective philosophical takes on life from a 25-year-old to like travel blog shenanigans from a year I spent abroad. And it hit me that LinkedIn is like a really good top of funnel for newsletter subscribers because there's a billion active users on the platform and nobody posts anything and it's a text-based platform meaning the conversion to a newsletter would be higher. My growth hack to like get attention on LinkedIn was I noticed there was this whole subset of like hustle culture, what I call like sales bros on LinkedIn. It's always these like fractional go-to-market guys who are selling courses but it's like there's this entire performative finance bro culture on LinkedIn that blows up where it's like you have to take an ice bath and meditate 45 minutes a day and if you do all these things you'll make a ton of money and it's insufferable. So I started posting satirical takes making fun of that but acting like I was one of those guys. The one I'm most famous for was I claimed that I wasn't paying for food in Manhattan and I was saving thousands of dollars a month by going to random hotels around the city and signing off on like other people's room numbers and getting free breakfast, free dinner, all this stuff. And, you know, it blows up. There's a lot of people in the comments like actually tagging the New York Police Department. It was crazy and it was hilarious and it gets millions of impressions. And then at some point I put, you know, if you like this take, check out my newsletter. And the conversion rate is fairly low, but on the amount of volume I was getting, I was still driving hundreds to thousands of like new subscribers if the post went really viral.

And anyway, Dan Wang, Professor Columbia, really liked my LinkedIn. I'd never met this guy, but it was during my first year of school, second semester. One of my friends texted me and he was talking about just like how like online networking. He was doing a class, I can't remember what the class was called, but it was basically like the evolution of social networks and like how the internet has changed communication channels among humans. And he mentioned there's somebody whose LinkedIn I really love and it's Jack Raines because it seems like he's just like hitting the like, he's just speedrunning the how do I growth hack a network that nobody's using and he's basically just exploiting LinkedIn. And he's really good at it and it's also hilarious because nobody's picked up on what he's doing. So I just walk out of my class and walk into his class and he was like, 'Are you him?' And he had like my LinkedIn up on the projector screen and I said, 'Yeah.' And he's like, 'This is hilarious. I'm actually fanboying a student right now. I'm a big fan.' I ended up doing like an independent study. You can do like one independent study at Columbia. And I did one with him on like how venture capital funds use social media to like basically build brand awareness to win deal flow, which is funny because I'm now a VC and that is like sort of part of my job.

But we talked a lot about the like call it [__] posting as a service. And my take on it is I actually think that when it comes to entrepreneurs building personal brands, being able to be pretty irreverent and being yourself online matters there. Like I know so many of these ghostwriting agencies that are making millions of dollars because every, especially like venture-backed founders, every entrepreneur just thinks they need to be posting content to get eyeballs. But the ones who are really good are like actually just kind of being themselves online and people feel like they get to know that person, they trust them. When you do that and you're around the hoop, like in the VC startup world, Twitter is probably the most valuable spot. I would say if you're trying to sell stuff, there's so many more enterprise buyers on LinkedIn than there on any other site. Like having a LinkedIn presence just helps massively with like customer discovery and it just lowers your like customer acquisition cost.

So like when it comes down to will business schools be teaching this stuff? I actually think it's pretty valuable to have some coverage of like how does a founder or sales leader or like engineering leader having a personal brand online both lower customer acquisition cost and also expedite hiring. Like the amount of job offers I've received from Twitter or companies I thought were interesting because I see the founder posting about it on Twitter and I look into what they do is it's in the dozens, right? Versus if you don't have any presence online and people are increasingly spending all their time online, you're just missing a low-hanging fruit for organic discovery of your thing. I think that actually matters a lot. Like this whole how advertising works and paid acquisition, like that's fine, but you can just expedite and accelerate like it's really on hiring, go-to-market, but just by having a good presence online matters so much for this stuff. And I think right now the business school curriculum like understates that and business schools are typically a few years behind the curve. Like now Wharton and Columbia are rolling out these like how to use AI courses when in reality even like Claude for Excel has been out for a year or two now. Like that's already like priced in. So I still think there's a lot of alpha in, you know, having a personal brand is a pretty cringe term but like loudly being yourself online is how I describe it. That I think is just incredibly useful. My whole career is basically built off the back of I don't shut up on Twitter, so I'm a little bit biased, but I think it matters.

Let's go.

I was born in Macon, Georgia, so dead center of the state. That's also where I went to college, Mercer. Yeah, but born in central Georgia and then grew up in a small town called Tifton, Georgia in Southwest Georgia.

So, they're both from southwest Georgia. My dad was from Ashburn, which is a little town outside of Tifton, which is itself a little town. Ashburn is like a suburb of a town that's already tiny. And then my mom is from Albany, Georgia, which is about 30 minutes from Tifton. It's all the same area code, southwest Georgia. The whole like section of the state probably has 100,000 people total. They both grew up there. Dad goes to Davidson undergrad, law school at Georgia. Mom went to Alabama. Her first job, she's a school teacher, ends up moving to Athens, Georgia. They end up like they were like living in the same apartment complex or same part of town. And like they meet when my dad's in law school, my mom's a teacher, get married. Dad gets a job offer at a law firm in Macon, Georgia. Takes it. Mom's teaching school there. Dad wants to go back to South Georgia and then he gets a job as like partner at a law firm or promotion at a law firm down there. Does it for a few years. But basically he was like always a South Georgia guy and then career just took him back there.

I don't know how exactly I would describe it but basically representing like I know that some of the cases were representing like agriculture chemical companies that were getting sued, right? So I would call the region too, like I would call it like corporate law is probably the best way to describe it but it wasn't like some specific, he did M&A or he did these specific types of suits. It was a little bit of everything. People forget that the lawyer stories that don't end up on TV consist of what is your local industry and what is the demand and needs for your services.

She taught fourth grade and second grade. So basically every subject at different times.

No, I did not. When I was two or three, she stopped teaching because she wanted to basically hang out with me more because I was awesome as a 2-year-old. Personal brand management as a toddler. That's right. Yeah. I had a lot to teach her then. And then after that she's been an interior decorator like on and off since then, but now it's basically like a full-time thing for her. Her grandma was like a very good interior decorator and it's kind of been a thing in the family. Hilarious.

Yeah. No, I think I have like, I mean she basically furnished the apartment. I think I have a better studio apartment setup than like most of my other bachelor friends in New York. So it's this wall behind you, this under it, like the TV and the...

It's good. Listen, I...

That's right. Most of my friends will hit me up and ask if my mom can send them recommendations for furnishing their apartments because zero single guys know how to furnish like a room, a house, anything. And it just matters. Like your dating life is much improved if you're not a slob is kind of how I think about it.

One sister, Frances, she's 24. And then my parents are both now divorced and remarried. So mom and stepdad, Birmingham, Alabama, dad and stepmom, South Georgia. My sister, she went to Georgia, graduated two years ago, and she is in Birmingham now, working in marketing for like a marketing firm down there.

Harry Potter books, massive reader. I didn't really play sports as a little kid. I played football, like rec league, for a couple years. I also had glasses since the age of three, and wearing glasses inside a football helmet sucks. And I wasn't that spec or what did... I don't even remember. They were just like glasses. But I was a huge nerd as a kid. Like geeked out on fantasy books. I speed-read all the Harry Potter books when I was like eight. All the Chronicles of Narnia books. Also a massive geography and history nerd. I remember just binging, the History Channel would have a history week where they would go through the history of the world over 10 days. I would watch all of it. I had a massive map in my room that had like, it was a map of the globe and I'd memorized the capitals of every country in the world. It was just, it was a whole thing. So, I was like textbook nerd up until the age of 13.

Started playing football again in seventh grade. I sucked. And then in eighth grade, I was really good. And then in ninth grade, I started on the varsity team. And at that point, my entire like career goal was I wanted to play football in college. I played football, basketball, and then I played tennis one year and ran track three years. But football was like, I liked basketball a little bit more probably, but I was a like a 6'3" white guy with a wingspan shorter than my height. So basketball was kind of ruled out. I was better at football and I was smart. Like I graduated valedictorian in my high school, but I didn't really, I guess I didn't care about school. I was competitive. But the priority and the thing that got me fired up was being better than other people at football and I really wanted to play in college. So, and then I kind of lived as a South Georgia kid. Like I went hunting a lot. Didn't love it. Like I've killed several deer and ducks and other random animals. That's just kind of what you do in South Georgia. There's a picture of me when I was 10 with like deer blood under my eyes. Like you shoot your first buck and you do that and I have its skull mounted back home. I didn't love it though. Like my summer job was driving tractors around and baling hay. We have a farm with like soybeans, hay, corn, a lot of cows, pine trees, and I would spray pesticides in all the like forested areas and then bale hay and other dig up tree stumps with the bulldozer. It sounds fun now that I'm like a city slicker who never sees grass. I was so bored though when I was like 15 or 16. I just could not wait to get out of South Georgia. I thought it was so boring. I was also in the back of my head worried that since we owned a farm, I figured I would be the one who would have to tend to it when I was an adult. So, I always thought I would have to move back to South Georgia. And that just sounded awful. Somebody who found it really boring. Luckily since I've gotten older, I've realized that there's a lot of things you can do. For example, you can sell land. You can put a data center on it, which is kind of what I'd love to do. Just throw a bunch of GPUs on that thing. We'll see. Take that, soybeans.

You can do both.

Math. Math. I mean, I've always thought history is the most interesting thing to study because I think like the books I like reading the most are books about people's lives or like phases of history told through the stories of people for example.

Yeah. Yeah. Like my favorite subject in high school was history. And it was also because my favorite teacher in high school was my history teacher. Was it...

C-O-R-N.

K. That's okay.

No, but he was the cross country coach. This guy was absolutely crazy. I mean he was not a career educator at all. Like he ran an aluminum business in Louisiana for 25 years, sold it, and then he just started yoloing his money into different stocks and he made bank on like Cleveland-Cliffs and like he was kind of a degenerate but also a good entrepreneur and he was just the man. And he was semi-retired in his late 40s, early 50s and his kids were like starting middle school or high school and the history teacher left and he was a huge history nerd and he just like went and met with the principal and said, 'I want to teach this.' And I don't know what the process is to become a teacher. I'm sure he got whatever certification he needed, but they were like, 'Okay, like we'll give it a shot.'

He paints the entire interior of his classroom like a map from the Middle Ages. It's, you know, you have these normal like whitewashed walls. No, it's like Lawrence of Arabia, Saudi Arabia, Egypt, the Levant all the way over to like modern day Pakistan and up to like Istanbul, right? He has movie posters all over the place from like movies like Havana, Lawrence of Arabia, 300, like all of the Braveheart, all these history movies. And in our world history class, basically every month we would go like all in on a random period of history, but he would focus on one or two protagonists from that period of history, like William Wallace, Marcus Aurelius, whatever. And then we would like, we didn't even use the history textbook at all. The whole thing would be told through either like old essays. It would be told through everything from movies, essays from people like Cynica, right? Like he would pull these either modern interpretations of old text or the old text themselves. And then he would have people like basically like act out some of these scenarios almost like doing a play at the front of the class from different things. And it was funny because we were in 10th grade, but he would dive into like how different kings like had all these affairs and how their love life ended up blowing up different like geopolitical tensions or how Henry VIII, like the whole reason the Anglican church exists is because he wanted to have like eight different wives and the Catholic church wasn't cool with it. So he creates a new church that creates basically there's an entire religious schism in Europe because one guy just wanted to sleep with like a dozen women, right? And it's just not the stuff you would get from a normal history class. And I found the entire like, oh wow, you know, if you're just like reading the Wikipedia highlights, it's this country conquered that country and this happened and that happened. But no, like every single thing was driven by some guy who wanted to do something and he just decided to do it. And his motivations for doing that were either driven largely by like insecurity, money, or sex. And that's kind of like the entirety of human history is sort of one of those three things. You either want more money, you want more sex, or you just want to be better than the people around you.

And it was, and you know then you start getting into okay like stock market and like different market bubbles and crashes from the tulip bubble to the East Indian company to like there was a crazy startup bubble in Austria and Germany in the 1870s around the time that silver was removed as like a global currency, right? And you're reading about all this stuff and you just start drawing parallels like you know the difference was people thought you could inject somebody with mercury back then and cure all their ailments or put leeches on your arm like a lot of the, you know, the science evolves but the human behavior is just the exact same thing over and over again. And to this date the books and essays I like reading the most really lean into how do you tell a story of a time through people. Like 1873, phenomenal book. Have you read it yet? We might have talked about this when I was on the other pod.

Yeah, it's the whole thing is basically about the rise and fall of the Rothschilds running the banking empire. So many just wild, wacky stories.

About like family collusion or just a bunch of market speculators or grifters rising to the top and then collapsing and having to move to like some island in the Mediterranean to get away from their creditors. Um, it's just like history is so much more interesting than anything else. And I've always—I studied finance and Spanish in college, but I've always thought history wasn't anything I ever wanted to major in, but it's the thing that I always find myself reading, watching movies about, like asking LLMs about now. They're phenomenal for going down a rabbit hole in particular people and periods of time, but I've always been a history nerd.

I haven't read it. I like—it's—it's on my list.