Jack Raines — The Authentic Path | Episode 170

This is the best time ever to be alive in human history. But I don't think we are by default well equipped to deal with the amount of choice that we have. And it leads to like paralysis by analysis. People get overwhelmed with choice now.

Everybody sometimes just completely ignores opportunity costs or even thinking about them.

Because I was 24 when I was doing that. You're healthier, easier to get around, more malleable, but it's still a finite window that you don't have. Peak health forever.

Memento mori, I think, is a good practice, right? Some people think it's morbid. I think it's quite liberating.

The current situation that I'm in now is probably the healthiest I'm ever going to be. So I should be doing as many things as I can. I didn't know anybody in Barcelona when I got there. That was my first stop. It kind of separates the, like, parts of you that were a byproduct of your environment, like where you fit in and the social hierarchy of where you are. And then the stuff that's left is what you actually like. You don't actually have to do whatever default path you think you're on. It's like essentially trying to trigger that wake-up moment. Don't take life so seriously, you know, just like have fun.

Well, hello everyone, it's Jim O'Shaughnessy with yet another episode of Infinite Loops. Today's guest is somebody that I have been watching off and on on social media, on his, uh, Beehive, on all of the various things he does. Uh, you're very well known for one particular thing that we're going to talk quite a bit about, but we'll get to that. My guest today is Jack Raines, who writes the Substack, or Beehive actually, right? Uh, Young Money, which I subscribe to and recommend that you should check out. It's very well written. For one so young. So congratulations there. The wisdom, the wisdom is strong in this one.

Yeah. Thanks, Jim. I appreciate it.

You are also a full-time MBA student at a little place I've never heard of, Columbia. Is that even an accredited business school or no?

The business school is. The undergrad had— there's a little fiasco there. I think the business school is still accredited, though.

Still accredited? Okay. Well, so— but you're doing it via correspondence course, right?

Yeah.

Yep. I'm kidding.

I'm kidding. No, I'm— yeah, I know.

No, no, you, you, you are definitely at one of the better business schools in the country. Congratulations on that. I love your stuff. I particularly love your LinkedIn Jester mode, which we're going to talk about a little bit. But first I want, I want to hear your story because you have a really fascinating story. During the pandemic, you took $6,000 and turned it into something like $400,000. Trading, uh, in SPACs and, and other, uh, instruments. Uh, you, you took full advantage of the low interest rate regime, so kudos to you. Good. You then lost a bunch of money and decided to have your first existential crisis at quite a young age, uh, in which you quit your job and traveled around the world for more than a year. We're going to talk about all this, uh, but first off, Jack, welcome, and tell us a little bit of your— what's your origin story? If we're going to sell this to Marvel, man, you better have a good one.

Well, first of all, thanks for having me. I've been listening to your podcast for a while, so it's like an honor to be on here. My origin story is that I'm from Tifton, Georgia. We're the reading capital of the world. You can double-check that. I'm not really sure how we got that label, but Tifton, Georgia is self-proclaimed reading capital of the world. Small town, like 20,000 people in southwest Georgia. I played football at Mercer University, small Division I school about an hour south of Atlanta. I always wanted to play at the University of Georgia. Wasn't big enough, fast enough, strong enough, or good enough to play there. Mercer was a consolation prize. And then I moved to Atlanta for 3 years. I worked in corporate finance for UPS there, had an existential crisis, as you said, after making and losing a lot of money and honestly, probably just being locked in an apartment for like a year and a half doing Zoom call meetings and fake work like a lot of other people were doing. And yes, just spent like a year traveling after that and then moved to New York for business school. And now I'm a very happy New York resident doing all the fun things that you can do in New York. So that's my elevator pitch on me in like 30 seconds.

I like it. I like it. We're going to need more color, though, if we're going to sell this.

Of course.

Marvel. So let's, let's, let's go in on the color. You write and say lots of really super interesting things that I want to talk about today. The first one is about opportunity costs. And you make the— you contend that opportunity costs are literally at the core and center of every decision that we make. And yet many people, and it, let's not, you let's not paint with a broad brush and say millennials or Gen Ys or boomers. Everybody, everybody sometimes just completely ignores opportunity cost or even thinking about them. Talk about that a little bit.

I think it's, I think it's weird now because we kind of, we live in a time where there's more access to optionality for literally everything, like career path, where you live, especially now that remote work is more flexible. How you spend your time, like who you date, who you marry, who you're friends with, just like everything you engage in. We have— we used to live in our own little respective bubbles in our parts of the world, and the internet's kind of blown that up. And then the post-COVID world has blown that up. I think people kind of get— I see it a lot now, especially with like young people trying to figure out what they want to do. There's this, this idea of like feeling like you have to do this amount of steps in this type of career and then essentially like buy your freedom to do whatever you want with the rest of your life. But the opportunity cost of that is you could spend your 20s and 30s doing stuff you don't really like with the intention of like buying back the ability to do what you want, like do what you like in your late 30s or 40s or 50s. And what I think happens is once you get to that point, you get so solidified in what you're doing that it gets even harder to make those changes or The way that I look at it is there's like different phases in your life that are like the right time to do different things. Like how you want to spend your time at 25 is probably going to be different from 35 or 45 or 55. So for me personally, like that decision to go travel a lot and see the world, I mean, part of it was like, as you alluded to earlier, I made some money trading stocks so I could afford to, but like there's a kind of hostel hopping, like no real worries, no responsibilities, where I could just go without a plan and go see and do a bunch of fun stuff that I wouldn't want to do when I was like 35 or 45. And I've seen other people hint at this stuff too. Like in Bill Perkins' book Die With Zero, he directly talks about his roommate doing a trip like that at 24. The Bill didn't go on because he didn't think it made sense financially, and they both ended up being very successful, making a lot of money later. But Bill missed out on experiences when he was younger because he didn't realize what the tradeoff was. Because it's like, it's really easy to see how much stuff costs, like money-wise. It's very hard to see how much something costs on just like the decision to do one thing over another thing. And because you can't really see those, like you can see dollars in a bank account, I think people miss out on how important opportunity costs are until like stuff's gone.

Yeah. And kind of invisible but very strong, right? The invisible threads that bind us as a society. Once you start examining them, you see that they're of like spiderweb strength. And, you know, for the most part, most people kind of go through life unaware that they have all of these strings attached to them. And one of the things that I like about you is that you became very aware of that. And took, took the opportunities in your youth to, to do those things. I have long maintained that anyone who can in their 20s, if they can live in New York City, they should live in New York. Yeah. Just because of all of the things you're exposed to that you simply can't get exposed to in any other major American city, I would say. Places in Europe you can. Talk a little bit about the hostel hopping though. What was, give me like, what are the 5 things you still like think about all the time that you learned on that 1-year trip around the world?

I think there's this like, there's this idea that people have of like going to Europe or whatever and finding yourself. And I think that's a lot of bullshit. I don't think you can go find yourself in like a nightclub in Budapest or anything like that. Something that I did realize is once you get out of your like home environment, for me, like getting out of Atlanta and going to like, I didn't know anybody in Barcelona when I got there. That was my first stop. It kind of separates the like parts of you that were like a byproduct of your environment, like where you fit in and the like social hierarchy of where you are. And then the stuff that's left is what you actually like. So like, I don't think you find yourself when you're going and hostel hopping, but you do get a lot better idea of like what stuff you did was actually stuff you wanted to do or what stuff you valued. And then I think it surprised me how quickly you can make friends with people who really have nothing in common with you just because you both have this plan of like traveling and seeing and doing a bunch of fun stuff. Like the first guy that I met, like I had this idea going into like into this trip, this whole romanticized, oh, see the world, this and that. And then you land in Barcelona My Spanish was rusty. Everybody's speaking Catalan and it's a little bit overwhelming. Feels like a mistake immediately. And then my first roommate is this like staunch, like socialist German guy named Jules, who we probably disagreed on everything worldview, but he was hysterical. And we went out, got dinner that night, got beers, went out, and then I'm in Berlin 4 months later. We end up hanging out. I meet a bunch of his friends. So like the amount of commonalities that like people can have and the speed that those relationships develop because you kind of like in the back of your head, both parties know you might only be hanging out for like 3 days. You can develop friendships that are legitimate, like strong bonds very quickly. I probably have like 20 people around my age that I've met, some of them only for like 12 hours, some of them for a week or two that I still keep up with. And when I'm back in Europe, I got 4 friends in London that I only know because we were in a hostel together. So the first tour that one it gives you a very good way to kind of evaluate like what you actually like, what you dislike, where your values are, just by getting out of your home environment, which for me was doing the hostel thing. Uh, like the speed at which you can make good friendships and how you can kind of skip the whole bullshit, like surface level, like the, like in the US there's like an appropriate level. You can't talk about really deep topics right away with new people because it looks like you're coming on strong, but when you're only with people for 3 days, you jump right into the like real life conversations with people who would be strangers, which is an interesting dynamic. And it's also just like a cheap way to travel. Like people think like travel's this expensive thing, but I was spending like $20 a night staying in hostels and like, yeah, you have like a lot of times you're going to have roommates and stuff and that leads to a whole other thing. Like some people are snoring, coming in late, coming in early. You'll have I had a French guy in a hostel room in Sevilla, Spain, that brought a girl back to this 10-person hostel, which is just a completely heinous thing to do. But I don't know, it's cheap. And then you also— the fourth thing is you can adapt to different living situations so quickly, like going from having like a pretty nice apartment in Atlanta, my own bathroom, living with my roommates, to being in places sometimes they had AC, sometimes they didn't. Sleeping on a train sometimes, but it's fine. Like, you can— like, it's much easier to adjust. So I guess the, the 4 things would be like, you get a better sense of kind of who you are, it's incredibly easy to make pretty deep friendships, um, it's cheap, and you're just a lot more adaptable than you would think. Those are, those are kind of my big takeaways.

Yeah, Mark Twain said, "Travel is fatal to prejudice, bigotry, and narrow-mindedness." And like, I totally agree with that. And You know, then there's the concept that Timothy Leary pioneered, which is that we all kind of experience the world through our own reality tunnel. The author who I love, Robert Anton Wilson, talks about this quite a bit. And one of the prescriptions that I agreed with when I was young and agree with now even more so is that if you can successfully, through travel, through like reading things that you normally wouldn't read, or even on social media. I, you know, if I was not lazy, I would have an alt that would subscribe to all of the people who I disagree with. As it is now, what I'll do is I'll go over and spend a day in their world just to try to figure out what the fuck is going on inside their head. And sometimes I'm successful and sometimes I'm not, but oftentimes I get like really cool insights that I know I would not have had had I not done that, right? And it's kind of like the, the idea that you're, you're always going to be better off rather than attacking a straw man, attack a steel man, create a steel man. No, no, the other point of view so well that you can, you can actually argue in its favor. As opposed to against it. You know, it just seems to me that the state of a lot of conversation, discussion, debate these days has really kind of gotten dumbed down to simply people making assertions. Just, I assert this, I believe this, and, you know, that's it. Do you have any proof for this? No, I know it's true. Right. And so, I think it's great to be able to, you know, build arguments based on data, things like that. And, you know, where appropriate. One of the other things you write about a lot, which I find really interesting in terms of where you are in life, you're young, obviously healthy, but you talk about health quite a bit. And, you know, Schopenhauer had a great quote, which was, "Health isn't everything, but without it, everything is nothing." What got you thinking about health at such a young age?

I remember like being in— I think it was in Barcelona too. But when you're— you see the, like, the cruise ships of, like, tourists coming through. And it was this whole— just a lot of, like, kind of senior citizens coming off and, like, struggling to get through, like, the cobblestone streets in the Gothic Quarter and this and that. And it's like these people probably have a lot of money. They're on a very nice cruise ship spending like, I don't know how much, tunas, more than Mediterranean. They can't actually do anything with it. Like they're very limited in like the, like, I guess the amount of like satisfaction they can get from that money because their health limits their ability to do stuff. And like, it's something that I've told, like, like I'm very fortunate that all my grandparents are still alive. That's something I've talked to them as they've gotten older, just in like, like my grandma's always loved to travel, but it's like You know, like she can't get around as well now as she could have like 20 years ago. And that's part of the reason like she wanted to go on this trip with my younger cousin was like she still can get around pretty well, but this might be one of the last like big international trips she does. But like talking to people who've like been alive a lot longer than me and seeing how like stuff that they said, like when you're young, you just have a lot more ability when you're healthier, like you you have the, like, the energy and the ability to, like, go do all this stuff. Like, what I was saying about the, like, like, ridiculous living situations, hostel hopping, like, part of the reason that that doesn't bug me is because I was 24 when I was doing that. Like, you're just, like, you're healthier, easier to get around, more malleable. Um, so I think part of it was just, like, seeing, like, knowing, like, as I age and get older, I am going to be less able to do a lot of different things. And then there's also, like, you never know if, like, like, I mean, you know, knock on wood, but you never know if you're going to get diagnosed with something or if an accident happens. So it's like, I don't know, it's a little bit morbid to think about, but I think you should have in the back of your head that like the current situation that I'm in now is probably the healthiest I'm ever going to be. So I should be doing as many things as I can, both like playing sports, doing active stuff, stuff that I think would be very enjoyable that I couldn't do later. And then also like taking care of myself to kind of prolong how long I can do that. But I think it's just like seeing people get older and stuff and realizing that health is a you can extend it, but it's still a finite window. Like, you don't have peak health forever. So yeah, it's probably that.

And memento mori, I think, is a good practice, right?

Yeah.

Remember that you're going to die. And the more you focus on that— some people think it's morbid. I think it's quite liberating in many respects because it helps you prioritize. Like, do I really want to die doing this?

Yeah. No, that's real.

And you'd be amazed. I'm sure you've experienced it. You'd be amazed at how much stuff that just eliminates from even you considering doing it, right? Like, yeah, no, I don't want to die doing this.

I— 100%.

You know, and it also speaks to your attitude about grind culture. Talk to me, because you've written a lot about it. I like what you write. What is going on? And that seems to be kind of a universal thing. It started as the Protestant work ethic, right? Which was, you know, you work, work, work, delay everything until, you know, you've succeeded and then you can enjoy life. In other words, it focused always on the outcome and not the journey, right? And you seem to be far more inspired by the journey By the experience, by doing things, as you just said, things when you're young, taking advantage of that, the ability to do that in good health. Also things like, you know, I can't remember who's originator of the quote, but all young people are time billionaires. And like, that is so cool. That is so cool. When I think back to what I was doing like in my 20s, I'm very happy I did most of it, but had I had that kind of concept of, dude, you're a time billionaire. You can use this time to like just do crazy stuff if you want. Talk about grind culture and why is it so pronounced? Is it, do you think it's social media? Do you think it's these endless guy accounts? You know, I'm the deck guy or I'm the travel guy or whatever. What— speak to me as an old who doesn't understand all that shit.

I think part of it is like there's— I don't know, it's the, the like flashy cars, lifestyle, stuff like that is very appealing to people who especially feel like you don't have money. That becomes kind of the thing that you want. And the people that are like putting that stuff out there propagating on social media attract a lot of eyeballs. So like people who are in money tight situations look at that like the opposite of what they have and therefore are kind of like inclined to lean into it. My general take on like the hustle culture stuff is that like the idea that you have to choose between one or the other, like you either have to grind 100% of your time or you're going to fall behind, just isn't true. Like I think the most successful people are people who do take, like I do pick a lot of fun at it, but like I take the like work stuff that I do, if you call it work, seriously, but it's not like all-consuming. And I think most Like the people that I look up to and whose lives like I kind of want to emulate are very good at what they do, but they also do what they want. Like you, like this idea that you have to sacrifice like the first like 15 years of your adult life in order to reach some like abstract idea of financial freedom just isn't true. And I would push back even more and say that like, if you do have to sacrifice all other like relational or fun or just outside out aspects of your life to reach that level of success, it says more about your inability to like prioritize stuff and like compartmentalize stuff than it does about the need for the grind culture in general. So for me, it's like, it's like, I think satire is a very good way to, I don't know, it's like a good way to like express truths without saying it. Like if you go on Twitter and say grind culture sucks or it's annoying, you just look like a hater. But if you can go over the top in grind culture, making fun of it, it gets the same point across, but it's funnier and it sticks with people. And a few people aren't going to understand it, which also kind of adds to the joke. Yeah, I think it's, I think it's, I think there's also a thing where people will like listen to like podcasts, read books, and take courses on how to be successful without ever actually taking action on a thing that would help them be successful. And it tricks your brain. You're getting that dopamine hit without actually doing the work. It's like actual, like, Success is like, like you've, you've had a very successful career, a lot of, in a lot of endeavors and a lot of us probably doing a lot of boring work that compounded over time. Like it wasn't this like flashy, like you didn't take some course then a year later we're like making millions of dollars. It's just like doing a lot of small decisions right along the way. But that doesn't sell. So yeah, it's, it's, that's kind of my, I don't really have like a fully refined thesis on it. I just think the whole thing is obnoxious and just like completely untrue. Um, but you're selling people on a dream is what it is. And I would like to, I guess, expose that by making fun of it. It's kind of my take on it.

I, I think that if you really want to teach anyone anything, first off, you can't. You, you can be useful to them, uh, but people learn what they want to learn. You, you're not going to take somebody aside and change them, in my opinion. You can't change a person. You can help them in If they want to change, you can do all sorts of things to help them. But like, if not, it just doesn't matter. And it seems to me that everyone's looking for the list, right? Here, if I do these 10 things, then I will succeed. I think like that is the biggest pile of horseshit I've ever heard in my life. And like, I got so triggered one time, like 5 years ago, reading one of these like, But wait, there's more. Yeah, you know, it was, it was beautifully crafted as, uh, as sales copy.

It was brilliant.

But I was so triggered by it. Like, I wrote a thread for Twitter, and I know for some reason they're forbidden now. Uh, I still write them. I like them. So fuck everyone who doesn't like them.

I think threads are actually a great, like, method of delivering stuff. It's just really shitty content has taken over most threads, so it gets associated with it. Like, I think, like, I know, you know, you and Trung are pretty good friends. Trung writes brilliant threads. I think he's one of the best. But it's the threads that are like the listicles of like 10 Chrome hacks or AI hacks that you have to know. Like, like shut up all the prompt engineer bullshit. Like these guys were peddling Web3 tokens 3 months ago. No, I like, I don't dislike threads. I think threads can be great.

So I completely agree on the idea though that if you wanna, if you really want to be of help to somebody, or at least if nothing else, be memorable, you really have to make it entertaining. Yep. And humor, I think, is one of the most misunderstood, like, superpowers. If you can be consistently funny, right, and make people laugh, because humor's all about the disconnect, right? It's all about the, ooh, I did, you know, that's the whole classic setup of a joke.

Yeah.

You know, did not see that coming. So, let's shift gears now to something that you do that I really love and I admire your balls for doing it. And that is the LinkedIn pranks. Tell our listeners and viewers about some of your favorites and what motivated you to actually begin these things because they are like fire and they also go viral, right?

Oh, it's insane.

Yeah.

Like they'll get like several million views. It's ridiculous. So for like some context, for the last, probably the last year now, I've been like shitposting on LinkedIn, which is posting stuff that's intentionally over the top, like ridiculously just not true, but positioned as financial advice, like hustle culture advice, entrepreneurial advice, money-saving advice. And it's been ridiculous. And part of the reason that I have done it and been able to get away with it is like, I don't have a real boss. We can get into this in a little bit, but like my only kind of boss is Liquidity, which is like a well-known finance meme page. And it benefits him to have me like grow my social accounts too, since I'm running his newsletter. So it's like, if I'm like causing, like stirring up a lot of attention on LinkedIn and getting more followers from it, then like it also indirectly sends more people to exact some. So I have like a lot more margin for error. But LinkedIn is a really weird platform because pretty much everybody's on there. Like it has 3 times as many active users as Twitter. So it's the most widely used text-based platform like out there. But nobody posts real stuff on there because everybody is either tied to their employer, their school, or a potential job hunt. If you put anything even mildly controversial on there, It could be the reason why you don't get a job. It could be the reason you get fired. It could get you sent in with a meeting with HR. So everybody's on LinkedIn and they're basically using it to congratulate coworkers on new jobs. And the entire, like, every LinkedIn post looks like ChatGPT is trying to write a LinkedIn post is what it feels like. Like nothing actually feels personal except the quote unquote hustle culture gurus who are selling some pyramid scheme course on I'm going to teach you how to be a business coach so you can teach other people how to be a business coach. Or here's 10 entrepreneurial hacks that I have on how to make millions of dollars. Now buy my course for like $5,000 so you can travel the world like me. It's ridiculous. And those are the only people posting like authentic stuff because like it's their business model. So one day it just kind of hit me like, one, it would be really funny making fun of this type of stuff. Two, the way that LinkedIn works is content stays on the newsfeed longer. Like on Twitter, stuff disappears within like 30 minutes. On LinkedIn, stuff resurfaces like a week later if somebody likes, 2 weeks later. So the half-life on a LinkedIn post is like 10 or 20 times longer than Twitter. And 3, because less people are posting content on there, it's just more likely to blow up because there's less competition. Like there's a lot of good content on Twitter. Twitter's tough. LinkedIn isn't tough. And I saw people were like just blowing up on LinkedIn and, but I didn't want to do what I would consider cringe, like stuff that wasn't my voice just to get a follow on LinkedIn. So the only thing that made sense was to just make fun of hustle culture by being over the top. So last fall, I wrote this LinkedIn post about like how I hadn't spent any money on food in Manhattan in 4 months since I moved here by just stealing food from like all these different hotels around Manhattan. I would walk in, go get the continental breakfast, like sign off on a random room number and leave. I would go back for dinner, like get like a nice steak, sign off on the penthouse, leave, like, take girls out to dinner at, like, the Intercontinental, leave. Obviously never did that. But I mean, people in the comments are going crazy, like, go fuck yourself. Like, people are actually writing stuff like this on LinkedIn. And you see, like, this person's like, like a VP of Microsoft. They're telling some, like, 25-year-old kids who literally, like, like, you're a piece of shit, you go to prison. How, like, you can't post that. You're like, you are— you're missing that. This is the joke. Your coworkers are going to see your comment. Like, you're actually harming yourself professionally. But then their network sees it and 95% of people get that it's satire. So it keeps blowing up because those 5% of people just keep feeding the engagement engine. So that one ends with an alumni from Columbia Business School emailing a screenshot of it to our Dean of Students, Samantha Shapsis. She's the bomb. I love her. She's great. But I get an email from her saying, hey, Jack, this is Dean Shapsis. I got an email from a concerned third party. About a LinkedIn post you put concerning your behavior. Can you come meet with me to talk about this? Because I really just have no idea what's going on here. It was like more so pure confusion than accusatory because again, it didn't make any sense. So I emailed back, yeah, like, would love to come meet on Thursday. Just for context, in the last few weeks I've also said that I got vaccinated 1,000 times as a side hustle back when New York was paying people $100 to get vaccinated, that I stored my little cousin in my carry-on bag to save on a flight. And then I called Joe Biden on his cell phone saying I wanted more student loan debt instead of forgiveness because it would make me grind harder. So I walk in her office like 4 days later and she's just looking at me. I was like, this has to be one of your more like interesting student meetings, right? Because we'd never met before. And she was like, well, I've read a lot of your stuff. You seem to be one of the more interesting students in business school. She's like, you're certainly not the typical going to banking or consulting. And I was like, I'm going to be honest, I don't think I could get hired by an investment bank at this point. Like, I think I would get dinged off off the rip. And she actually knew exactly what was going on. She was like, so let me guess, you're doing this to get attention on LinkedIn, to funnel it back to your newsletter or your blog or whatever. And it's basically just like your marketing strategy is pissing people off on LinkedIn. And I was like, yeah, I mean, that's the— in a nutshell, it's basically what I'm doing here. And she thought it was hysterical. I thought— I was like, do I need to remove Columbia from my LinkedIn? Like, is this like an issue? She was like, no. I'm just glad I know what you're doing now. So next time I get one of these emails, I can say, oh no, he's not actually like defrauding hotel chains. He's just lying on the internet. And I was like, all right, that's completely fair. But yeah, so the one that really got people going was I pretended like I was applying for an internship at Goldman Sachs. And I think this was in April. We have this cluster cup where like all the classes at Columbia were divided into clusters. Our first semester, we have a big competition, like there's a soccer tournament. We have a big, like, charity auction, fundraise, scavenger hunt. But we also had a beer mile, and it was the worst thing I've ever done in my life. You run a lap, drink a beer, run a lap, drink a beer. It's like 4 beers, 4 laps. It's— I'm decent at drinking beer and I'm decent at running a mile. Those two shouldn't ever be done together. But one of my buddies got a funny picture of me across the finish line looking like I was about to die. And I've made this ridiculous LinkedIn post about how like after David Solomon, Goldman CEO, has been doing this DJ tour because he is actually a DJ. He's been taking advice from other 25-year-olds he's been partying with and he couldn't figure out what to do to fill out a competitive internship class. And they told him, oh, you should have them do the beer mile. The rationale is Goldman interns work notorious hours, so you need to see if they have the stamina. And there's also like kind of an alcohol dependency problem in the banking industry. So you need to make sure that they both have the stamina and the tolerance to handle like long nights on the bottle. And I put this ridiculous thing about how I trained, like running, like drinking beer and running a mile on the West Side Highway every morning for 4 months. Went out there, smoked everybody. I mean, the comments were insane. Like, this is misogynist. Like, oh, was there a woman beer mile too? There was. We actually timed them differently. So it was a pretty DEI event. But I mean, it got like 7 million views. And some of my buddies who work at Goldman said that it actually did get brought up in an HR meeting. Like, somebody from Goldman was like, this kid's pretending to be an intern and he posted this. But if they would have contacted me, I would have blown it up even more, right? Like, it would have been even more ridiculous. But yeah, it's just funny seeing how angry people get at something where if you just take a second and think about it, you have to realize like this didn't happen. Like Goldman Sachs— no company is going to have kids like run a beer mile to see who gets an internship slot. Doesn't even make sense. But because it fits that, like, like that, oh, like Goldman Sachs, like fraternity culture, it's just a bunch of white dudes in suits who party, finance, whatever. It's just plausible enough that somebody's going to believe it. And it's been hysterical. Like, it's my favorite thing that I do on the internet. It's so much fun.

Hey, for those who didn't hear me cackling, I think that these are hysterical. You know, O'Shaughnessy Ventures might do a beer mile.

You should. I think it's, it's a hysterical competition. It is so funny. I mean, it's horrible. Like, I played football in college. I'm playing rugby now, and there is not an athletic event I've done that's more tiring and just like mentally difficult than a beer mile. I stand by that.

I'll tell you, too, back to the power of travel, right? So if you haven't been to Bhutan, I highly recommend you go there. Okay. It's like the— its formal name is the Dragon Kingdom of Bhutan. Which shows you how badass they are.

That's just—

that's awesome. And, and, and one of the things that's really cool is archery is their national sport. However, it is drunken archery. Basically, we got a chance to watch these young guys and women compete in this competition where literally the target is almost a football field away from them. But first, they get massively fucked up on Bhutanese beer. And like literally they are staggering when they, when they take the bow in hand and you know, you're, you just can't look away, right? Yeah. You're watching and you're watching and then the, the thing that just blows you away is you see them plant their feet, draw back, bullseye. And they are obviously drunk. Then the next guy comes up. What does he do? He splits the first guy's arrow. And then like, I'm looking at my wife and the people we were traveling with and I'm like, is this really happening? Can you like, do you think they're faking the being drunk? No, because we went early and we watched them drinking and like, it was beer. I went, our guide was with us and he goes, yes, many of the clients that I take around actually insist on going and taking a sip to make sure it was—

To make sure they know.

Yeah. That it's really, you know, the doubting Thomas aspect. But so the next thing that I wonder is, was this you subconsciously just basically saying, you know what, I'm going to close off any opportunity that I have to— you call it a collar of a job— to put on the collar of a Wall Street job or an investment banking job or whatnot? Or was that not part of the thought process?

I think it's not even so much to close that off, but it's like anybody who I would want to potentially ever work with or do anything like that with would probably appreciate what I'm doing or see it like as something that's valuable, entertaining beyond just like, oh, this guy's like such an HR liability, I probably would be on that aspect with stuff like this. But like anybody that I would potentially work with, something like this is going to make enough noise that it makes me more likely to meet people like that. And it like has worked. Like I've, like I've met so many random people. Like, so like, like I've posted some shit posts on Twitter about BlackRock owning everything and then me actually owning BlackRock. And like I saw Gary Tan, CEO of Y Combinator, follow me on Twitter the next day. Like stuff like that. Like He's hysterical. I sent him a screenshot. I Googled who owns Y Combinator and like DM'd him a screenshot of that and said, you're next, Gary. And he just sent back the eyeball emoji. Like, I love that. Like, okay, I know that he has a great sense of humor off the rip. But yeah, like it's both. It puts me in a spot where I literally couldn't get a job that I probably wouldn't want. Like it forces me to find something else that works and also like increases my likelihood of finding opportunities. Of like potentially working with people or just like meeting people and chatting with people that like I actually wanna talk to. So it's a win-win. It works better on both fronts.

Yeah. Yeah. It's a great sorting mechanism too, right? Because 100%, as you point out, right? If, if somebody doesn't, first, if they don't get the joke, they're an NPC to begin with, right?

Yeah.

Like, yeah. You know, so you get rid of all of those. Then the people who might get that it's a joke but think it's, inappropriate. Also, people stick up their ass. You probably aren't going to want to deal with them. So you managed to like sort all of those, those types out of the equation. I love the fact that you did it on Twitter and that Gary followed you.

It's hysterical.

Yeah. Like, listen, if you don't get the joke and, you know, it's kind of a great metaphor for what's happening right now. We're doing this series that is slow because they've got so many other things going on called the Great Reshuffle, right? And like, it's all of the old business models are collapsing and you have all of these people having these hysterical meltdowns, like legacy media, like the campaign to get people back into the office. It's just so painfully bad. And then when, and it also for anyone who's looking, you can see the collusion of the handmaidens in the legacy media writing all the stories that, like, why don't you just announce bought and paid for by, right?

100%.

One of the things that I always, uh, propounded was we should make all of the Congress critters be like NASCAR drivers. They should have to wear the logos of the companies that have bought them, right? So you know when they're walking into Congress, oh, here comes GE or BlackRock. And yep. And, oh look, they're talking to Goldman. I wonder what they're going to talk about over there. And like, it lays that bare in a really humorous way that people are just having a hard time like figuring out, right? In terms of like, that the man in the gray flannel suit just isn't going to cut it in this new world.

Yeah.

Do you find that, is there an age thing going on here? Is it mostly old fucks like me who are getting all setting their hair on fire about it, or are young people too?

Definitely old fucks like you for the most part. But no, I think the kind of reason that it happened is like COVID kind of, like we were talking in the very beginning about how people kind of get so caught up in life, they just start living passively. And then COVID was a real shock where a lot of people working remote, which one all of a sudden shows that, oh shit, all these jobs actually can be done remote. And like, I actually prefer in-person stuff. Like, I love— like, I think there's a lot more spark when you're like with people in person. But like, the idea that some stuff physically can't be done remote is bullshit. Like, people should be able to like— yeah, you might want them in the office, but like, if they're like taking a trip or something, they should be able to do— any white-collar job can be done remote, at least to some extent. But it's kind of like a power thing. Like when everybody's in person or whatever, like you can kind of control people's time more. When stuff's remote, people have a lot more autonomy. So it's not even as much an age thing as it is people who were very much in power or the top of the, like, the power hierarchy 4 years ago view this shift as them losing that power. It just happens that, like, people who were in those positions are like probably like 20, 20-plus years older than me that have already climbed that ladder. And so then it's kind of like maybe almost bullshit that other people don't have to go through the same grind or same process they did to get where they are. Like now there's other paths and might piss you off and feel like you spent like age 25 to 45 going through a lot of shit to get where you are. And then you see this like 26-year-old kid who realizes he doesn't really have to. I think, I think there's a lot of that going on too.

Yeah. You know, it's funny, I have a lot of friends in investment banking and like, from the point of view of a mostly entrepreneurial asset manager, I just did not understand the culture of investment banking. Like, no, it— and so like, I would genuinely, no fucking around, I would like say, why? Why do you have such a toxic culture? Yeah, I had a guy who worked for me, super charismatic. He was the president of his fraternity at UConn. He worked for me at O'Shaughnessy Capital, which was the first version of O'Shaughnessy Asset Management. And he went into investment banking and I'm like, dude, you really, I, after being in our culture, you're really, really going to hate it. And so we caught up and like, he was, he was like, you were absolutely right. And because essentially his senior banker tortured him for his entire time training. And, and he, he finally had a conversation with the guy saying, like, do you enjoy— like, he really confronted her. He's like, yeah, you do enjoy torturing people. I mean, does it give you pleasure to make me show up at 5 AM to do the PowerPoint and shit like that? And the guy looked at him and in all sincerity said, You know, no, but I had to go through it, so fucking A, you, you have to too. And it's, it's this, it's such a weird mentality. In other words, we have this toxic culture that we hate it and that we inflict on the people behind us because goddamn it, we had to go through it. I, I mean, do you think, is there a cure? Do you think things like your over-the-top LinkedIn things will, will, will like get people thinking a little differently?

I think, I think one of the biggest things is like people are starting to realize there's more opportunities. Like it used to be that, say you are— and I remember Matt Levine wrote a pretty good piece about this, but just saying how he was talking about banking specifically, but how like it was always a thing where you have somebody who's a very smart, driven kid who like has the capacity to do a lot of good things, has no idea what they want to do. Investment banking just sounds right. It has prestige. You're going to make a lot of money. You have optionality out of it. You know, it's going to suck going into it. But they take those type of kids and have them grind for a few years because those type of kids, that's the default thing you're going to go into when you know that you can do big things and have no idea what you want that big thing to be. I think the thing that's breaking the mold a little bit is there's just more opportunities now and it's easier to find those opportunities now to like still have a very lucrative career, but doing stuff that's actually more enjoyable. Like the idea that people don't like to work, like this whole quiet quitting, it's bullshit. Like people like working really hard when it's stuff worth working on. But yeah, grinding like 80 hours a week because you're going through making sure every font is right on a PowerPoint, or it's like, like, oh no, like the color code is like one tenth of a rad off, and like this part of the thing doesn't match the company. Like, that's not work. That's actually, it's pretty heinous to put like high achieving people doing very tedious tasks like that, especially just because it's always been done that way. You put those people in something where they actually get to do strategic thinking or be creative or whatever, people will work 80 hours a week because it's not even work. It's like, uh, it's like a stimulating thing. Like I've, I don't know, like with my own stuff, I've had several times where I'm like finishing up a blog at like 4 in the morning or like working on some newsletter stuff or just like something like that. Or just like researching interesting stuff. On quote banking hours. It doesn't feel like working. It's just like what I wanted to do. And I think there's a lot more opportunities for one, people to do their own thing and make money through it, or there's a lot more jobs in finance, in tech, in whatever, where you can make decent money doing stuff that's actually fun. Like a lot of my, like there's a lot of people obviously doing banking and consulting at Columbia now, but I have a lot of friends also like interning for different VC firms where they are doing like a just ridiculous variety of tasks or like people with like PE firms, smaller niche teams that are just doing stuff that's not the standard like bullshit. So I mean, I feel like with business school, I've had a good sample of seeing a lot of people doing dozens of different things. And I feel like compared to 5 or 10 years ago, people are waking up to the idea that there's more opportunities. And when you start seeing that you don't actually have to do something that sucks because there's other options that are like financially similar outcomes, why wouldn't you do the one that sucks? So I think that's going to force a cultural change because like top achievers are just going to quit going to jobs that suck if they have another viable option.

Yeah. And is that something that you're noticing? Like you have a successful newsletter, right? Young Money. And one of your maxims, which I heartily agree with, is you need to be authentic. You need to be distinctive. The minute you're speaking in an inauthentic voice, it's like the old comms, the old PR models, right? Was always in corporate speak. Yeah. It was decided and passive, passive language.

Yeah.

It was decided by some nameless, faceless Borg that this was gonna be the way. And like they're getting blown outta the water by people like Lulu Masserbi and others who are, you know, talking like actual human beings. Yeah, I think that, uh, I think that that's a trend that people are still underestimating.

Yeah, yeah, 100%.

I think that people don't really— and, and your gags, uh, as, as LinkedIn's resident jester, uh, really underline how people don't yet really grok how your average human, like, they see that as bullshit from everybody, 100%, right? And, and yet, why are you seeing a change among your peers, like at Columbia? So Columbia is a great example, elite Ivy League business school. Probably a lot of the colleagues that you have there are going to go into iBanking or going to go into McKinsey or whatever. Uh, are you seeing a palpable thing that you can notice and measure with people saying, you know what, no, fuck that, I'm not going to do that. I'm going to go try this over here.

Yeah, it's— well, it's funny right now because pretty much everybody started their internships within the last week or two. So you have like the— and like people are in like every bank, consulting firm, whatever, all sorts of stuff. But yeah, there's definitely chatter of like, what did I get myself into? This and that from some people. Some people love it. And again, there are like varies from person to person and it depends on like, like what company they're with, what team they're on. Like the people that you're working with can kind of make or break like it being a fun, long work to like a torturous experience like you were talking about with that other guy. But yeah, people are definitely like, again, I can't compare it to like how it was 10 years ago because I wasn't like 26, 10 years ago. But it seems to me like there is very much like people are very cognizant of Okay, this might not be it. I'm open to something else, which is good. Like, I think people are like really seriously thinking about this. And then also like being aware of like, if you don't really like it now, then you're looking at like your MD or the VP that's ahead of you or whatever. And it's like, if they're like 37 and not happy and I'm 27 and don't like it, like what's the outcome? You're going to spend 10 years doing something that is going to probably make you not happy like that guy. Like people are like aware of that. So yeah. I think like most people my age are at least asking those questions. And that's, I mean, I think that's the most important part of it.

Yeah. And you know, I see it percolating and I'm very hopeful because, you know, the unlock that we have today, first off, I think we are incredibly lucky to be alive at this moment in history.

Oh, 100%.

And the, you know, the people who think they're being romantic saying, oh, but I'd love to go back to, you know, the Rousseauian nature, uh, no, you don't. Nature killed you often and was really, really dangerous. And Tennyson's Nature is red in tooth and claw— he was not overstating it. Like, if you read about even a time when my own father was alive, right, 1921— he was born in '21, right? But like Calvin Coolidge, who was president of the United States, His son died from getting a sliver from a wood tennis racket because no antibiotics, went into sepsis, dead.

Yeah.

And, and, and like, these people are like, oh, but so, you know, the world is so much with us, late and soon getting and spending, we lay waste our power. Yeah, but that was fucking dangerous. We have all these really cool tools that allow people more choice, not less. Yeah. Do you think, do you think that having more choices is a deterrent or do you think that it, it is a, a good thing?

I think, I think it's a good thing like objectively, but I think our ability to deal with it's tough because it's like, I don't know, like, like you said, like 100 years ago, like, like I've got like a great aunt that had polio, right? Like that's like, that's 2 generations back. Like that was like stuff like that was the norm. So we have like medically and technologically advanced. Increased incredibly fast over the last, say, 50 or 60 years. But, you know, like evolution is a thing that takes hundreds of thousands of years. So essentially, like there's, I don't even remember the origin of the quote, but we have like, like our bodies, like what, like primitive machines and we have godlike technology or whatever. Like we aren't, we like us as humans haven't evolved at the rate that our technology has. So, Yeah, like we get overwhelmed by choice. It used to be everything was driven by scarcity and now it's the complete opposite. So I still think it's a good thing, but I think it's very hard for people to like work through that. But if you can work through that, it's better. Like the upside now is so much like the, I don't know, it's better, but you can't compare what your experience is now to the human experience 200 years ago. So you didn't live it. All we can do is read about it, learn about it. But like, yeah, people get overwhelmed with choice now. I agree with you. This is the best time ever to be alive in human history. But I don't think we are by default like, well equipped to deal with the amount of choice that we have. And it leads to like, and that like paralysis by analysis. It's just a lot.

Yeah, I think that's a good segue to your notion about luck. I also had a guest on, George Mack was his name, and he had what he called Luck Razor. Jack Raines, which was basically he made all of his choices based on what he perceived as which option would give him the biggest chance at luck. Yeah. And you followed a similar idea with, you call it increasing luck surface area. Talk to me about that and why that's important.

Well, this is something I talked to Nick Majuli about. I think he quoted— I'm going to— I don't remember the direct quote, but it was an idea that you had talking about New York specifically just being a place that, like, there's a lot more chances to make those almost like accidental, incidental connections because it's so many people doing interesting things in a small area. Everybody knows everybody. But yeah, like New York geographically is a place that kind of increases your luck surface area. Like you just have more potential chances to make contact with the right person at the right time through complete incident. Like, I was at— I was getting breakfast in Balthazar like a month ago, and I just ran into Howard Lindzon at breakfast, and it was a complete fluke thing. We'd like interact on Twitter before, but I'd never met him. And then I ended up chatting with him, Fred Wilson, who he was sitting with, and just talked to them for like 45 minutes, literally about shitposting on LinkedIn. It was the stupidest conversation ever. And I ended up going to this, like, not financial advice film premiere at Tribeca Festival. Like, Howard got me a ticket to it just because, like, I emailed him after. He kind of thought our conversation was funny. He's like, hey, you should come to this. And ended up like, but that's something that only happens in New York. Like I had to be in, like that would have never happened when I was living in Atlanta. I think the internet is the ultimate luck surface area thing where if you can make some noise, again, like, but you want to make the right kind of noise. Like if you make the wrong kind of noise, you'll attract the wrong kind of people. Like the, I guess the wrong luck surface area. But if you're actively putting the type of stuff out there that would attract people that you want to meet, people start to find you and vice versa. And then like, once like you have like on Twitter, for example, I see people have certain followers. It's like a green light to me that like, oh, like Jim follows this person. Like, that's a good sign that they follow him. Or Morgan Housel follows this person or so-and-so. The internet just allows those like connections to happen at exponentially higher rate because you can connect with people all over the world. So yeah, I mean, I think it's especially early in your career, putting yourself in a spot where you can make as many of those connections as possible within what you're trying to do. Like a good business school is another impersonal example where like most, like it's objectively a very fun experience. Like I have a ton of just like my friend group in business school is a phenomenal group of people. I also know the odds of a good proportion of them going on to be very successful in a lot of different industries is high just because of where we are. That's a luck surface area thing. Like the odds of having a social group that start like having strong friendships with people doing interesting stuff is higher from where I went to business school. So yeah, luck plays a big role in stuff and you can't ever actually like predict how big that is. But yeah, I agree that you can put yourself in situations where luck is more likely to work in your favor. So like New York and the internet are the two biggest luck surface area increasers out there, I think.

Yeah, I agree. I don't know about that Howard Lindson character though. He's really sketchy.

Yes, he is.

I wouldn't spend much time with him if I were you. He tried to get me to go to that movie, but I was like, fuck that Howard. I just watched it anyway because the director sent me a copy of it.

I'll tell you what, it was a good story. It was funnier than I thought it was going to be. He asked me what I thought afterwards. I was like, I actually thought this was going to suck going into it. And I was like thoroughly entertained. So I had very low expectations. It was a solid movie.

Yeah, no, in fairness and joking aside, I really wanted to go, but I had an unexpected trip to California come up. And so I did get a chance to see the whole movie and I had the same reaction.

Yeah.

And I love Howard, so him joking about him being a degenerate, even though it's true, I still love him despite his degeneracy. But the movie, and he was the executive producer of that movie.

Yeah.

Uh, is really great. Um, I was really honestly kind of surprised, uh, because I went in kind of expecting it to, you know, like, how am I going to thread this needle, right? Because we don't want to give away the plot too much, but yeah, it's, it's, it's about, um, the misadventures of people— what, in what we're going to talk about next, uh, in, in crypto, specifically in our friend Elon Musk's Dogecoin. Let's, let's pivot to crypto because you, you are, you have an unusual attitude about crypto, uh, for one so young, in that you are like, uh, how to put it politely, you, you are a real crypto skeptic.

Talk about that. Yeah, that's, I mean, I think it's all bullshit. From like, I don't know, the, the only thing that I've seen that kind of makes sense with it, and it's really because there's not a better legal established way to do it, is like the moving money country to country and using crypto as a brief intermediary. I have a lot of buddies from Argentina. I get that. Like, that one makes sense because it's just faster and more efficient. It still doesn't mean like buying those coins is going to be a good investment. It's going to go up over time. You're switching from like dollars to pesos in a matter of minutes. So that's my one exception to the whole thing. But yeah, I mean, I don't know. I think if it takes 10 years to find a use case for something, it's probably not that useful. Like, I had more use cases in 3 minutes than Bitcoin had in 11 years. Like, Bitcoin's been around since the great financial crisis. Like, it has its learner's permit right now and people are still debating use cases. Like, is it inflation hedge? Like, I don't know. I think it's fine for people to buy the stuff to speculate with. This idea that it's like when the bull case for that working is the current financial system collapsing. One, that's a shitty bull case to have. And then two, if the current like system does collapse, like you're predicting, why is anybody going to give a shit about this like orange internet coin? Like, what are you going to do with that? Like, it's going to be like taking up arms, getting a bunker and fighting for your life like an apocalypse. Like, nobody's going to give a shit that you have a decentralized currency. The computers probably won't work. So I, I think it's one of those things where That there's no, like, and you might completely disagree with me on a lot of this, but I don't really think there's any value creating anywhere. Like you see with Axie Infinity was a thing that like, I've been blocked by Chris Dixon on Twitter for probably a year and a half now for chirping him about Axie Infinity being a Ponzi scheme because it was. But all these Filipino, all these people were putting money in, so I'll have Filipino workers like grind away on some game to earn an in-game currency that can be exchanged for real money. But all the money's coming in from somewhere. Like there's no value actually being created. I don't know, it's just wild to me that it's like the one thing, like the pushback is always, oh, there's fraud in traditional finance too. Lehman Brothers, this and that, there's bad stuff. Yeah, there is. But like in crypto, the fact that like Coinbase is kind of the like airbringer of like, oh, like we're the best in crypto because we're the only ones who haven't actively committed a fraud. Like when fraud is the norm and not the exception, I don't know, that's probably a red flag. Yeah, I mean, I think the whole thing's bullshit. I think the worst part about it is there's talented people going to be software engineers for companies like that instead of building technology that could actually improve people's lives. Like, let's find, like the only crypto companies are just exchanges to trade cryptocurrencies that have value because people are throwing money at them. It's entertaining. I think there is, the use case is entertainment value. It's hysterical watching people like, like get levered up like 500x to trade CumRocketCoin or something like that. Like there is a lot of entertainment value in that. But yeah, like, I don't know, I think it's all bullshit. That's, that's my, that's my spiel on it. I'm very like loud about that because crypto people get really offended really easily too. So it's a fun group to chart for sure.

Well, you had the, you had the remark that, you know, stocks are based on, you know, the real economy. Uh, whereas crypto is based on vibes and narratives and stories.

Yeah.

Uh, I, I, I think that, uh, I'm, I, I'm trying to remain open-minded to things like use cases for— like, Ethereum might be a really inter— and blockchain might be really useful actually in AI, uh, in keeping versions straight, in keeping, you know, what was in the model back than with version 1.1 versus version 1.7, because a lot of people are worried that people are going to tamper with the models and actually remove stuff that was very useful. So I think, you know, something like, uh, you know, a blockchain permanent record would be interesting.

Yeah.

Uh, but, uh, in terms of the, the crypto trading, yeah, I I couldn't figure that out. And it was like, I just saw it as really harmful, especially to young people, especially to people who were not well-versed in investing and whatnot. It's a bit like Robinhood, right? Like, I loved the idea when I heard it first, and then when I saw the app, I was dismayed because the app looks like online gambling, right?

Yeah, it's a joke. Robinhood's a casino. But like, I mean, You get free stocks by doing a virtual scratch-off lottery ticket. Like, come on, that's like that, uh, that, that analogy is very obvious.

Uh, yeah, so it's, it's like I, I'm really open-minded to anything that I hope can get younger people to invest sooner. And I, and I, and I mean invest, I don't mean gamble, I don't mean scratch-off tickets or lotto or, uh, you know, Dogecoin. I mean actual investing. Um, and, and so I, I do believe that gamification can help, uh, in learning, uh, but it can also hurt, obviously, because you wanna— if you wanna understand who understands human psychology and Human OS really, really well, look at game— video game designers and casinos, man. Like, casinos, I The— I have like an anthropological interest in casinos because every single hack on human OS is in display in a casino.

That's incredible.

No clocks, beautiful people serving free drinks, um, you know, slot machines that are, are, uh, weighted to pay the most at the entrance to the casino so that you have all of the people screaming, I won, I won! And, and yet it is like the saddest thing in the world to me because like, these are people gambling money they don't have and, you know, they're, they're gambling, surrendering it to the house, right? Like, people don't understand the basic odds of these things. And like, I don't want to sound like a scold, it would be cool if you could come up with a gamified way for people to understand like Holy shit, that's a really bad bet, right? Yeah. And, and I could definitely see that as, as something that, you know, you could even commercialize and, and make, make some, some money on. You also talk a lot about risk, which I'm happy to see as well. And several things I noted down that, that you've written in or said in the past. You know, when trying to quantify risk and you say things like, you know, the worst thing is that you can have an early success because then you think that you are like the God's gift to whatever you're doing. And that fucks with your mind. And you also say risk is the highest when everything seems perfect. And most significant risks can't be forecast but appear obvious in hindsight. So like, risk fascinates me because it pushes every button of human OS, especially that last one where you can't forecast the significant risk, but it seems so incredibly obvious in hindsight. Talk about what got you off on thinking and writing about risk and and how you try to help people understand it better?

I mean, honestly, just 'cause I was an idiot when I was like 23/24. So going back to the trading thing, right? I turned, I won't get in like the intricacies of what I was doing, but basically SPACs were a bubble and SPAC warrants, which were like call options with a 5-year expiration date, were also a very, like the bubble within that bubble. And long story short, I just got really good at figuring out which ones are gonna pop off before they did. Just from like being on the internet too much. And it was easy. So I'd turn $6 grand into $400 grand. And after I got like to about $150 grand, I stopped trading warrants 'cause they were like, they could go to zero. Like warrants have no floor price. SPAC shares before the merger actually happens, there's a floor. Like you can actually calculate how much you could lose on any trade 'cause you can redeem that SPAC for $10 and change. So I get up to like $400,000 where I'm being meticulous about never having a trade that I could lose more than like 5% on. And once it, like, once the price went up 25 or 30%, I would sell. I like, I was very methodical, but the SPAC bubble was a bubble. When there's a bubble, everybody gets in on it. And once everybody had launched a SPAC from Shaquille O'Neal to Speaker of the House Paul Ryan, there wasn't enough money to like bubble the SPACs anymore. There were too many. It got diluted. So I'm sitting there with like $400,000 and the SPAC bubble pops. Now I don't like, I lose like $10K on that. Like, I barely get touched by it. I'm talking to my dad and he knows what I'm doing. I've been— I was like, I'm, I'm like 23. I just made like 6 times my salary. So I called him and I was like, yeah, like, this really isn't working anymore. But also, like, I've got like $400 grand. He was like, you're a fucking idiot if you don't sell at least half of that. And just like, he's like, you can throw that in the S&P. It'll be like $6 million when you're retirement age. I was like, yeah, but also I'm up 4,000 or I'm up 6,000%. If I make another 150%, I'm a millionaire at 23. That's like 3 more trades and that won't be that hard. Like, I can get a couple that work well. In hindsight, that was just the stupid— like, I— that's an unbelievable sentence to say. And I felt completely fine saying that because again, like, I did have a method that was like, even in hindsight, looking back on it now, what I was doing worked. I knew it worked. I knew exactly how much risk I was putting on. But as soon as that bubble popped, I naively assumed that, oh, I can find another trend that I can make a lot of money on. And I didn't. I played one trend really well for 9 months and it was gone and I should have just cashed out. And then I kept trading and I tried to trade. I put way too much money in a former SPAC that was a buy now, pay later company that was looking at the financials they projected for the next year, really undervalued versus like Afterpay and Affirm. And interest rates were still zero. So buy now, pay later was a viable business. I'm like, now and I put like all my money in that and then they completely missed their earnings projections and I lose half my portfolio in a day. And it was the definition of everything had literally gone right for me for like a year and a half. So I knew in the back of my head that there was technically risk there, but I didn't actually think that bad thing was going to happen. I didn't think they were going to miss earnings about 30% on their first earnings report as a publicly traded company. So completely blew it. And then I cashed out and just like took a week and just left that money in cash, my brokerage account. And then I ended up putting it in like a couple index funds. And then I was sitting there just kind of thinking back my entire thought process of the 18 months that led me to that point. And it was like a whole rollercoaster of the entire like human psychology, like every single emotion, greed, fear, luck, risk, whatever. But yeah, that was kind of the defining moment that made me think of that. And that's what I see in the, especially in the trading side of the crypto bubble and NFTs, like They're different assets, but I haven't gone all the way through the up and down and kind of back to the middle on that. I just see that all the time in financial markets now with like any kind of bubble or whatever. And that was what really kicked off that thought about risk for me because it was like looking at it now, like separate from it, it was absolutely insane to be that young and risk that much money on something stupid. Like I didn't need to, like I had so much money I could put in, invest. I could have cashed out like $100K and just blown it over 2 years and had $300K that I left invested. That's a phenomenal way to, like, do it as a 24-year-old. Instead, I just blew it on something stupid and had way less money to, like, do stuff with after it. So that was the— that was like— that was the moment that really solidified, or at least kicked off how I started thinking about this stuff. But the thing about the worst thing that can happen is winning big early. The best thing that happened to me was losing that money versus making $1 million or $2 million. Because I probably never would have started writing. I would have been insufferable and thought I was better than everybody because I traded stocks better than everybody. I would have gotten absolutely wrecked at some point, like maybe not financially, but something would have happened that would have fucked me up at some point after that because the hubris I had from that. So I don't know. I mean, losing $150 grand isn't great, but I'd consider that like a— it was a price worth paying compared to like how much worse it could have been. Because the higher you go before you fall, the worse it gets. And once you get hit once, you never really forget it. Like, that stays with you. Whatever stuff's going good now, I'm always thinking about how could this fuck up? How do I keep that from happening? And it's— yeah, it's—

it's—

I'm better because of it.

Yeah. Cormac McCarthy, who just died, unfortunately, one of my favorite writers, had a great quote, which is, you'll never know what worse luck your bad luck has kept you from.

Yeah. And 100%, that's real.

But the inverse is I had an experience very much like yours, which was I was trading a particular type of system which was very different than what I did with, you know, long-only quant algorithmic investing going into the crash of 1987. And I had amassed the biggest put position I ever had. In my young career. I was 27 years old and I sold it all to basically break even the day before the crash. And oh wow.

What would you have made if you kept the position on for another year?

Millions. Millions of dollars. And much like you, at first I was devastated. But as I thought about it more and more, and now as I look back, was the best thing that could have ever happened to me because I would've been insufferable, for sure. Oh, for sure. Right? Like I would've been just like a complete ass, right? Because I would've thought, look, I made this fortune because all you idiots didn't understand the market was going to crash. And then I would've, it would've been horrible. But the other thing it did was it finally pushed me over into being a total quant. Because it demonstrated to me that I was not exempt from human OS, that I was just as likely, maybe even more likely, to fall into all of the traps. You know, fear, greed, hope, and ignorance are the Four Horsemen of the Investment Apocalypse. Yeah, man, like everybody falls for them, me included. And, and one of the things that that experience really cemented in my mind was I am not a mutant and therefore I've got to build a process around the way I make these investments or I'm going to fuck up just like everybody else. Yeah. So I think the, you were very astute to see that maybe that was one of the best things that could have ever happened to you because it doesn't feel like that at the time, but it's certainly in my experience it was. And so I'm, delighted to hear that you took that away. That also led to your wanderings and travel. And you know, what were your 3 favorite places in your entire year of traveling around the world? What were the 3 places that were either your favorite or where you felt like you learned the most by being there?

Well, also going into that, I booked that trip before that trade happened, so it was a very good, like, all right, you're about to go to Europe now. You don't have to worry about the stock market. This is what you get for trying to do both. But 3 favorite places. So I, Argentina was the place I spent the most time in. I was living in Buenos Aires for 2 months and it was literally because I'd majored in Spanish and finance in undergrad. And then on, well, like I spent the first leg of that trip 4 months in Europe. I went back to Sevilla, Spain and got dinner with a family I lived with when I studied abroad there like 3 years earlier. Couldn't understand anything they were saying. Like, southern Spain has notoriously difficult Spanish to understand. Like, people from Colombia and Mexico struggle, and like, Andalucía. But as someone who hadn't spoken it since graduating, I was like, damn, my Spanish is trash. And it kind of pissed me off because that was something I was like, I would like to be bilingual. So I just went to Argentina with this guy that I met at a hostel in Lagos, Portugal, 3 months earlier. We just got an Airbnb in Buenos Aires. And that was the, that was the number one spot. Argentina was phenomenal. The people were great. The food was great. It was because it was one place that I actually kind of lived for a little while. I actually got to, like, experience, like, just being in, like, a neighborhood for a couple of months, like, meeting the guy who owned the gym, like, some of the local restaurant owners. It was— Argentina was freaking awesome. And it was just like, it's very weird because Buenos Aires is a, like, especially like in the better parts of the city is super nice. Like, it feels like It's literally picked up out of like, like it should be in Spain. Like it feels like a European city, but it happens to be in Latin America. It's much more European than like being in like Colombia or some other places, but their economy like sucks. So they're in hyperinflation. Their currency's awful. The quoted exchange rate when I was there was 100 pesos to the dollar. You could get 200 to the dollar on a black market. So I'm like, Getting a steak dinner, like at a nice, like, well-known place for like $12 with a bottle of wine. It was crazy. So we were, I guess, spent like maybe $3,000 in 2 months and I was balling out down there. But it was just cool. Like it was, it was funny. Me and my buddy Mike had a rule where like we would have to go on a date with a girl who doesn't speak any English once a week. Just to like force us to speak Spanish in the most high-pressure situation possible and then report back. On every awkward, funny interaction we had. Like, I— the verb coger in Spain, where I studied abroad, means to get. Like, I could say, like, quiero coger un agua, I want to get a water. In Argentina, coger means to have sex with, and I didn't know that. So, like, I'm in a restaurant, I, like, straight up told this girl I wanted to fuck a beer. Yeah, like, there was a lot of that. So Argentina was the most, like, I don't know, constructive part because I actually had to get used to kind of living in a spot like that, and it was beyond just doing the touristy stuff. Tromsø, Norway, Northern Lights. It's like 200 miles north of the Arctic Circle. As far as just a place that's completely different, I was there in late November. The sun was up for like 22 minutes a day while I was there, and it was just— it didn't even look like the same planet. And the people that I met were super cool. It was mainly some other travelers. The hostel owner's name was Robin. Super nice guy. Like, lived in the States for a little bit, but we were at a bar one night and met this guy who was literally like, a Viking descendant, like, looks like he'd been out of a time machine. He was hammered drunk and asked us if we wanted to go fetch women that night, which is a ridiculous, like, phrase to use. But as far as just seeing, like, different people and just a completely different place, Tromsø, Norway, and then Japan. Japan was just like— I went to Japan for the first time this past spring, and it was like, it was just cool. Like, sumo wrestling tournaments. The food was phenomenal. It was the most culturally different place. Like, I've never been to a place that's so different from the West. It was just night and day because even in Latin America, like, they're listening to the same music. Like, it's like you don't have to speak Spanish to get around down there. Japan was like a different world. So Japan, Tromso, and then Argentina would be the three.

Yeah, I've never been to Argentina, but Japan, it's— it is a— you are a foreigner in a foreign place.

It's nuts.

And like, I remember, like, you can't even figure out how to use a payphone, uh, back when I was there the first time in the late '90s. And like, literally, I was helpless. I was trying to like make a phone call from the hotel, and it was like I, I couldn't even, I couldn't even articulate. And she did— the woman who was the operator spoke no English.

Oh, of course.

And, and, and so, but what a great experience, and what a great place to go. So I highly recommend Japan.

There's a lot of funny things about it too, because it's such a refined culture, but in a couple of ways it's not. Like, there's like this kind of like— they don't talk about it, but it's completely normal for people to just get like blitzed during the week, pass out on the sidewalk, and then go to work and shower the next day. But in every other aspect, they're the most well-put-together, like button-down people, and nobody talks about it. Like that blew my mind. I thought like, I, I don't know. That's just, wasn't something I expected. And because it's so developed, I like made the mistake of kind of assuming because it's really developed and the US is really developed, it would almost be more accommodating to English speakers. But like, yeah, the lack of English over there shocked me, but the languages are like, like, like learning Spanish from English. It takes about 600 hours of concentrated study. Japanese is like 2,200 hours. It's like, 3.5 times, 4 times more difficult than like a typical romance language. So it makes sense, but super cool place.

Yeah, I, I love Japan and I love the Japanese. And again, it speaks to the more you travel, the, the better, because the more you can learn and the more you can learn how even places like, uh, let's say Tokyo, which seem like a different world, you, you do not only notice the differences but the commonalities that we human beings share regardless if we can't like speak to each other or our cultures are very different. Well, this has been a blast, Jack Raines. First off, tell everyone where they can find you, where they can find your letter. Oh, and a last question. Why did you leave Substack and go to BeHive?

It was honestly a logistic thing at first. So I like, I write my own newsletter blog. I don't really know which one to classify it as called Young Money. Um, but there's this popular finance meme page called Liquidity.

And when I was like, I had him on the podcast.

He's the man. He's so funny. Yeah. He, um, but yeah, I just DM'd him on Twitter about seeing if he wanted help with his newsletter because I was just trying to find something to do while I was traveling. And he was like, actually, yeah, like I'll pay you to basically edit it, help put it together every day. And I was like, I'm just hostel hopping in Europe. I was like, that's, that's, that's a deal. Like, that easily pays for my lifestyle right now. But he was in the process of moving to Beehive because he knew Tyler Dick, who was the CEO of Beehive, previously been one of the first employees of Morning Brew. So I was on Substack and then Lit moves to Beehive. And then I have like, we're doing like a business deep dive, like a Patrick McCormick style one on Beehive when they were kind of like launching out of the beta phase., and Tyler was just walking through all the stuff they were rolling out and I was like, this just like seems like a better like product plan. And then knowing how he'd basically scaled, like he was kind of the main guy behind Morning Brew's growth from like 50 or 100,000 to a couple of million. It made sense. And then also just logistically, if I was going to be doing liquidity stuff on Beehive, I just wanted all my stuff in one spot. I'm biased, like I guess because I use Beehive a lot now, but it was initially a logistic thing and I trusted that they were going to deliver on the roadmap with like Everything from cross-recommendations to all the landing page customizations, to just everything. And they've like exceeded my expectations. So I've been really happy with it. So it was like a logistic thing and seeing if they were gonna hit everything they said and they've crushed it.

Awesome. And so you're, you're, all your stuff is over there, Young Money. Yeah. And on Twitter, what's your handle on Twitter?

Yeah, so Twitter handle is Jack_Raines. LinkedIn, you can just look me up as Jack Raines. My job title is curator of vibes. It's my LinkedIn account. It'll be pretty easy to find. And then yeah, my newsletter blog is youngmoney.co. I have a little like cartoon stick figure art on all my thumbnails. So that's kind of my style for that. But yeah, subscribe to that. Find me on Twitter, on LinkedIn. I'm more likely to respond to like DMs and stuff on Twitter. My LinkedIn DMs are a shit show.

But yeah, I can only imagine. All right, well, as a listener of the podcast, you probably know what this final question that I have for you is, and, and that is that, uh, we're going to play a game and we're going to make you the emperor of the world for a day. Uh, you can't kill anyone, you can't put anyone in a reeducation camp, but we are going to hand you a magical microphone that you get to speak into, and you get to say two things into the microphone. And what's going to happen is whenever the 8 billion-plus people that occupy this particular rock, uh, wake up in the morning, they're going to think that the two things that you said were their own ideas, and they're going to immediately act on them and start doing them. So you're going to incept them. What two things are you going to incept in the world's population?

Um, Shoot, that's good. I think the first one would be telling people, and this might be biased just being in the US, but telling people like, you don't actually have to do whatever default path you think you're on. Just like essentially try to trigger that wake-up moment. And I don't know, don't take life so seriously. You know, just like have fun. That's, I mean, that's the biggest advice I have for anybody. So yeah, you don't have to do what you think you have to do and have fun.

That's it. I like it. I like it. Well, Jack, this has been a lot of fun. Uh, really enjoyed it, and best of luck to you.

Thanks, Jim. Appreciate it.