Jack Raines — The Authentic Path (EP.170)

Hi, I'm Jim O'Shaughnessy, and welcome to Infinite Loops. Sometimes we get caught up in what feel like infinite loops when trying to figure things out. Markets go up and down, research is presented and then refuted, and we find ourselves right back where we started. The goal of this podcast is to learn how we can reset our thinking on issues that hopefully leaves us with a better understanding as to why we think the way we think and how we might be able to change that to avoid going in infinite loops of thought. We hope to offer our listeners a fresh perspective on a variety of issues and look at them through a multifaceted lens, including history, philosophy, art, science, linguistics, and yes, also through quantitative analysis. And through these discussions, help you not only become a better investor, but also become a more nuanced thinker. With each episode, we hope to bring you along with us as we learn together. Thanks for joining us. Now please enjoy this episode of Infinite Loops.

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 Beehive, on all of the various things he does. 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, 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 is strong in this one.

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.

Yep.

I'm kidding.

No. Yeah, I know.

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 gonna talk about a little bit. But first, I wanna 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 in SPACs and other instruments. You took full advantage of the low interest rate regime. So kudos to you. You then lost a bunch of money and decided to have your first existential crisis at quite a young age, in which you quit your job and traveled around the world for more than a year. We're going to talk about all this. But first off, Jack, welcome. And 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 good consolation prize. And then I moved to Atlanta for 3 years, 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, so 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 and life. 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. 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. You contend that opportunity costs are literally at the core and center of every decision that we make. And yet many people— and 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 weird now because 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, who you date, who you marry, who you're friends with, everything you engage in. 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 see it a lot now, especially with young people trying to figure out what they want to do. There's this idea of 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 buying back the ability to 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 different phases in your life. They're like the right time to do different things. How you want to spend your time at 25 is probably going to be different from 35 or 45 or 55. For me personally, that decision to go travel a lot and see the world, I mean, part of it was, as you alluded to earlier, I made some money trading stocks so I could afford to, but there's a kind of hostel hopping, 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 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 in a 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 trade-off was. It's really easy to see how much stuff costs money-wise. It's very hard to see how much something costs on just the decision to do one thing over another thing. And because you can't really see those, like you'd see dollars in a bank account, I think people miss out on how important opportunity costs are until stuff's gone.

Invisible but very strong. The invisible threads that bind us as a society. Once you start examining them, you see that they're of spiderweb strength. And 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 the opportunities in your youth 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 City. 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 are the 5 things you still think about all the time that you learned on that 1-year trip around the world?

There's this idea that people have of going to Europe or whatever and finding yourself. 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. But 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— 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, 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 what stuff you did was actually stuff you wanted to do, or what stuff you valued. 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. I had this idea going into this trip with 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. It feels like a mistake immediately. And then my first roommate is this like staunch 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 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. And I probably have 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, like I have 4 friends in London that I only know because we were in a hostel together. So the first two were that one, it gives you a very good way to kind of evaluate 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. The speed at which you can make good friendships and how you can skip the whole bullshit surface level. In the US, there's like an appropriate level of you can't talk about really deep topics right away with new people because it looks like you're coming on too 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, it's just like a cheap way to travel. People think travel's this expensive thing, but I was spending like $20 a night staying in hostels. And a lot of times you're gonna have roommates and stuff, and that leads to a whole nother thing. Some people are snoring, coming in late, coming in early. 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— I think 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. It's much easier to adjust. So I guess the, the four things would be like you get a better sense of kind of who you are. It's incredibly easy to make pretty deep friendships. It's cheap and you're just a lot more adaptable than you would think. Those are kind of my big takeaways.

Mark Twain said, travel is fatal to prejudice, bigotry, and narrow-mindedness.

100%.

And I totally agree with that. And 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. 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 reading things that you normally wouldn't read, or even on social media, I, 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 really cool insights that I know I would not have had had I not done that. And it's kind of like the idea that you're always going to be better off rather than attacking a straw man, attack a steel man, create a steel man, know the other point of view so well that you can actually argue in its favor as opposed to against it. It just seems to me that the state of a lot of conversation, discussion, debate these days has really gotten dumbed down to simply people making assertions. Just, I assert this, I believe this. That's it. Do you have any proof for this? No, I know it's true. And so I think it's great to be able to 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. 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 being in, I think it was in Barcelona too, but when you see the cruise ships of tourists coming through and it was this whole, just a lot of senior citizens coming off and struggling to get through the cobblestone streets and 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, I don't know how much, too. And it's more of the Mediterranean. They can't actually do anything with it. They're very limited in the amount of satisfaction they can get from that money because their health limits their ability to do stuff. I'm very fortunate that all my grandparents are still alive, but it's something that I've taught to them as they've gotten older. My grandma's always loved to travel, but 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 she still can get around pretty well, but this might be one of the last big international trips she does. Talking to people who've been alive a lot longer than me and seeing how Stuff that they said, when you're young, you just have a lot more ability. When you're healthier, you have the energy and the ability to go do all this stuff. What I was saying about the ridiculous living situations, hostel hopping, part of the reason that that doesn't bug me is because I was 24 when I was doing that. You're healthier, easier to get around, more malleable. So I think part of it was just knowing 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, knock on wood, but you never know if you're going to get diagnosed with something or if an accident happens. 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 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 playing sports, doing active stuff, stuff that I think would be very enjoyable that I couldn't do later, and then also 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— you can extend it, but it's still a finite window. Like, you don't have peak health forever.

Memento mori, I think is a good practice. 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. Do I really want to die doing this?

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. No, I don't want to die doing this.

100%.

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, which was, you know, you work, work, work, delay everything until you've succeeded, and then you can enjoy life. In other words, it focused always on the outcome and not the journey. 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, I can't remember who's originator of the quote, but all young people are time billionaires. 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 concept of, dude, you're a time billionaire, you can use this time to like 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? I'm the deck guy or I'm the travel guy or whatever. Speak to me as an old who doesn't understand all that shit.

I think part of it is the 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. 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 the hustle culture stuff is that 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. I think the most successful people are people who do take— I do pick a lot of fun at it, but I take the work stuff that I do, if you call it work, seriously, but it's not all-consuming. And I think the people that I look up to and whose lives I want to emulate are very good at what they do, but they also do what they want. This idea that you have to sacrifice the first 15 years of your adult life in order to reach some abstract idea of financial freedom just isn't true. And I would push back even more and say that if you do have to sacrifice all other relational or fun or just outside 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. I think satire is a very good way to 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 gonna understand it, which also kind of adds to the joke. 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 cause you're getting that dopamine hit without actually doing the work. It's like actual success is like you've had a very successful career in a lot of endeavors and a lot of it was probably doing a lot of boring work that compounded. It over time. It wasn't this 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. I don't really have like a fully refined thesis on it. I just think the whole thing is obnoxious and just completely untrue. 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 think that if you really want to teach anyone anything, first off, you can't, you can be useful to them. But people learn what they want to learn. You're not going to take somebody aside and change them. In my opinion, you can't change another person. You can help them if they want to change. You can do all sorts of things to help them, but if not, it just doesn't matter. It seems to me that everyone's looking for the list. If I do these 10 things, then I will succeed. I think that is the biggest pile of horseshit I've ever heard in my life. I got so triggered one time 5 years ago reading one of these, but wait, there's more. It was beautifully crafted as sales copy. It was brilliant, but I was so triggered by it. I wrote a thread for Twitter and I know for some reason they're forbidden now. I still write 'em. I like 'em. So fuck everyone who doesn't like 'em.

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. You and Trung are pretty good friends. Trung writes really good 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. Shut up with all the prompt engineer bullshit. Like these guys were peddling Web3 tokens 3 months ago. I don't dislike threads. I think threads can be great.

I completely agree on the idea though. 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. And humor, I think, is one of the most misunderstood superpowers. If you can be consistently funny and make people laugh, because humor's all about the disconnect, it's all about the ooh, that's the whole classic setup of a joke. Did not see that coming. So let's shift gears now to something that you do that I, 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.

It's insane. They'll get like several million views. It's ridiculous. So for like some context, probably the last year now I've been shitposting on LinkedIn, which is posting stuff that's intentionally over-the-top ridiculous, just not true, but positioned as financial advice, 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 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 grow my social accounts too, since I'm running his newsletter. So it's like, if I'm stirring up a lot of attention on LinkedIn and getting more followers from it, then like it also indirectly sends more people to ExactSum. 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 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. Everybody's on LinkedIn and they're basically using it to congratulate coworkers on new jobs. And 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 authentic stuff because it's their business model. So one day it just kind of hit me. 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 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, but I didn't want to do what I would consider cringe stuff that wasn't my voice just to get a following on LinkedIn. So the only thing that made sense was to just make fun of hustle culture by being over the top. Last fall I wrote this LinkedIn post about how I hadn't spent any money on food in Manhattan in 4 months since I moved here by just stealing food from all these different hotels around Manhattan. I would walk in, go get the continental breakfast, sign off on a random room number and leave. I would go back for dinner, get a nice steak, sign off on the penthouse, leave, take girls out to dinner at the Intercontinental, leave. Obviously never did that, but I mean, people in the comments were going crazy, like, go fuck yourself, people are actually writing stuff like this on LinkedIn and you see like this person's a VP of Microsoft, they're telling some like 25-year-old kid, you're a piece of shit, you should go to prison. You can't post that. You're missing the joke. Your coworkers are gonna see your comment. 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 that 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 and I was like, "this has to be one of your more interesting student meetings, right?" 'Cause 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 gonna 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 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. I was like, yeah, I mean, that's in a nutshell. It's basically what I'm doing here. And she thought it was hysterical. I was like, do I need to remove Columbia from my LinkedIn? 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 all the classes at Columbia were divided into clusters in our first semester. We have a big competition. There's a soccer tournament. We have a big charity auction fundraise, a 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. 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 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 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 drinking beer and running a mile on the West Side Highway every morning for 4 months, went out there, smoked everybody, And I mean, the comments were insane. Like, this is misogynist. 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. Somebody from Goldman was like, this kid's pretending to be an intern and he posted this. But if they would've contacted me, I would've blown it up even more. It would've 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. That doesn't even make sense. But because it fits that, oh, like Goldman Sachs 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. It's my favorite thing that I do on the internet. It's so much fun.

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

You should. 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's not an athletic event I've done that's more tiring and just mentally difficult than a beer mile. I stand by that.

I'll tell you too, back to the power of travel. If you haven't been to Bhutan, I highly recommend you go there. Its formal name is the Dragon Kingdom of Bhutan, which shows you how badass they are.

That's awesome.

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 literally, they are staggering when they take the bow in hand. You just can't look away. And you're watching, and you're watching. And then 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? Do you think they're faking the being drunk? No, because we went early and we watched them drinking. It was beer. 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 the doubting Thomas aspect. But 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, 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?

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 as something that's valuable or entertaining beyond just, oh, this guy's like such an HR liability. I probably would be on that aspect with stuff like this. Anybody that I would potentially work with, something like this is gonna make enough noise that it makes me more likely to meet people like that. And it like has worked. I've met so many random people. I've posted some shit posts on Twitter about BlackRock owning everything and then me actually owning BlackRock. And I saw Gary Tan, CEO of Y Combinator, follow me on Twitter the next day, stuff like that. He's hysterical. I sent him a screenshot. I Googled who owns Y Combinator and DM'd him a screenshot of that and said, "You're next, Gary." And he just sent back the eyeball emoji. I love that. I know that he has a great sense of humor off the rip. It's both. 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 increases my likelihood of finding opportunities, potentially working with people, or just like meeting people and chatting with people that like I actually want to talk to. So it's a win-win. It works better on both fronts.

It's a great sorting mechanism too, 100%, as you point out. First, if they don't get the joke, they're an NPC to begin with, 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. You managed to sort all of 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. Listen, if you don't get the joke, it's kind of a great metaphor for what's happening right now. We're doing this series that is slow because I've got so many other things going on called The Great Reshuffle. 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 it also, for anyone who's looking, you can see the collusion of the handmaidens in the legacy media writing all the stories. Why don't you just announce bought and paid for by? One of the things that I always 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. So, you know, when they're walking into Congress, oh, here comes GE or BlackRock and oh, look, they're talking to Goldman. I wonder what they're going to talk about over there. It lays that bare in a really humorous way that people are just having a hard time figuring out. In terms of the man in the gray flannel suit just isn't going to cut it in this new world. 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 I think the kind of reason that it happened is we were talking at 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. I think there's a lot more spark when you're like with people in person. The idea that some stuff physically can't be done remote is bullshit. 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 power hierarchy 4 years ago view this shift as them losing that power. It just happens that people who were in those positions are probably 20+ years older than me that have already climbed that ladder. And to them, 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. Now there's other paths and might piss you off and feel like you've spent 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 there's a lot of that going on too.

You know, it's funny, I have a lot of friends in investment banking and from the point of view of a mostly entrepreneurial asset manager, I just did not understand the culture of investment banking. I would genuinely, no fucking around, I would like say, Why, why do you have such a toxic culture? I had a guy who worked for me, he was 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, after being in our culture, you're really, really going to hate it. And so we caught up. He was like, you were absolutely right. Because essentially his senior banker tortured him for his entire time training, and he finally had a conversation with the guy. He really confronted him. He is like, do you enjoy torturing people? I mean, does it give you pleasure to make me show up at 5:00 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 have to too. 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 goddammit, we had to go through it. Is there a cure? Do you think things like your over-the-top LinkedIn things will get people thinking a little differently?

I think one of the biggest things is people are starting to realize there's more opportunities. It used to be that, say you are— and I remember Matt Levine wrote a pretty good piece about this. He was talking about banking specifically, but how it was always a thing where you have somebody who's a very smart, driven kid who 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'll 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 still have a very lucrative career, but doing stuff that's actually more enjoyable. The idea that people don't like to work, like this whole quiet quitting, it's bullshit. 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, oh no, like the color code is like 110 of red off. I'm like, this part of the thing doesn't match the company. That's not work. That's actually, it's pretty heinous to put high achieving people doing very tedious tasks by 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 work 80 hours a week because it's not even work. It's like a stimulating thing. 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 something like that, or just like researching interesting stuff on quote banking hours. But 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. 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're doing a just ridiculous variety of tasks, or like people with PE firms, smaller niche teams that are just doing stuff that's not the standard bullshit. 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, cuz there's other options that are financially similar outcomes, why would you do the one that sucks? So I think that's gonna force a cultural change cuz top achievers are just gonna quit going to jobs that suck if they have another viable option.

Is that something that you're noticing? You have a successful newsletter, 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 was always in corporate speak. It was decided, passive language. It was decided by some nameless, faceless Borg. That this was going to be the way. And like, they're getting blown out of the water by people like Lulu Misurbi and others who are talking like actual human beings. I think that that's a trend that people are still underestimating. And your gags as LinkedIn's resident jester really underline how people don't yet really grok how Your average human, they see that as bullshit. Everybody does. 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. 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?

Well, it's funny right now because pretty much everybody started their internships within the last week or two. So you have like people in like every bank, consulting firm, whatever, all sorts of stuff. But yeah, no, there's definitely chatter of what did I get myself into, this and that from some people love it. It varies from person to person and it depends on what company they're with, what team they're on. 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. Again, I can't compare it to like how it was 10 years ago, cause I wasn't 26, 10 years ago. But it seems to me 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 being aware of if you don't really like it now, then you're looking at 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. 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. I think that's the most important part of it.

I see it percolating and I'm very hopeful because the unlock that we have today, first off, I think we are incredibly lucky to be alive at this moment in history. The people who think they're being romantic saying, oh, but I'd love to go back to the Rousseauian nature. 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. If you read about even a time when my own father was alive, 1921, he was born in '21, but Calvin Coolidge, who was president of the United States, his His son died from getting a sliver from a wood tennis racket because no antibiotics, went into sepsis, dead. And these people are like, oh, but 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. Do you think that having more choices is a deterrent? Or do you think that it is a good thing?

I think it's a good thing objectively, but I think our ability to deal with it's tough because like you said, 100 years ago, I've got like a great aunt that had polio. That's 2 generations back. Stuff like that was the norm. So we have medically and technologically advanced incredibly fast over the last, say, 50 or 60 years. But 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 our bodies like primitive machines and we have godlike technology or whatever. Us as humans haven't evolved at the rate that our technology has. So 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. The upside now is so much, 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 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 well equipped to deal with the amount of choice that we have. And it leads to like paralysis by analysis. It's just a lot.

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, which was basically he made all of his choices based on what perceived as which option would give him the biggest chance at luck. And you followed a similar idea. You call it increasing luck surface area. Talk to me about that and why that's important.

This is something I talked to Nick Majuli about. I think— 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 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. I was getting breakfast at 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 and Fred Wilson, who he was sitting with, and just talked to them for 45 minutes, literally about shitposting on LinkedIn. It was the stupidest conversation ever. And I ended up going to this, not financial advice, film premiere at Tribeca Festival. Howard got me a ticket to it just because I emailed him after. He kind of thought our conversation was funny. He's like, "Hey, you should come to this." But that's something that only happens in New York. That would've 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, But you want to make the right kind of noise. If you make the wrong kind of noise, you'll attract the wrong kind of people. I guess the wrong, like, 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 once you have, like on Twitter, for example, if I see people have certain followers, it's like a green light to me that Jim follows this person. That's a good sign that they follow Morgan Housel, follows this person or so-and-so. The internet just allows those 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. A good business school is another in-person example where it's objectively a very fun experience. 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 strong friendships with people doing interesting stuff is higher from where I went to business school. Luck plays a big role in stuff and you can't ever actually 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 Lindzon character though. He's really sketchy.

He is.

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's actually a true 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 a very low expectation. It was a solid movie.

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

Talk about that. I mean, I think it's all bullshit. 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 make— mean like buying those coins is going to be a good investment. It's going to go up over time. You're switching from my dollars to pesos in a matter of minutes. So that's my one exception to the whole thing. I think if it takes 10 years to find a use case for something, it's probably not that useful. Like AI had more use cases in 3 minutes than Bitcoin had in 11 years. Like Bitcoin's been around since the great financial crisis. It has its learner's permit right now and people are still debating use cases. Is it inflation hedge? I don't know. I think it's fine for people to buy the stuff to speculate with 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 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? It's going to be like taking up arms, getting a bunker and fighting for your life like an apocalypse. So nobody's going to give a shit that you have a decentralized currency. Computers probably won't work. I think it's one of those things where 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. They have 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 people are putting money in to have Filipino workers 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. There's no value actually being created. It's just wild to me that it's the one thing. 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 in crypto, the fact that Coinbase is kind of the airbringer of We're the best in crypto because we're the only ones who haven't actively committed a fraud 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 can actually improve people's lives. The only crypto companies are just exchanges to trade cryptocurrencies that have value because people are throwing money at them. It's entertaining. The use case is entertainment value. It's hysterical watching people get levered up 500x to trade cum rocket corn or something like that. Like there is a lot of entertainment value in that. But yeah, I don't know. I think it's all bullshit. That's my spill on it. I'm very like loud about that. 'Cause crypto people get really offended really easily too. So it's a fun group to chart for sure.

You had the remark that stocks are based on the real economy, whereas crypto is based on vibes and narratives and stories. I'm trying to remain open-minded to things like use cases for Ethereum and blockchain might be really useful actually in AI in keeping versions straight, in keeping what was in the model back then with version 1.1 versus version 1.7, because a lot of people are worried that people are gonna tamper with the models and actually remove stuff that was very useful. So I think something like a blockchain permanent record would be interesting, but in terms of the crypto trading, I couldn't figure that out. 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. 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.

It's a joke. Robinhood's a casino, but like you get free stocks by doing a virtual scratch-off lottery ticket. Like, come on. That analogy is just very obvious.

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

It's incredible.

No clocks, beautiful people serving free drinks, slot machines that are 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 yet it is like the saddest thing in the world to me because these are people gambling money they don't have. And they're gambling, surrendering it to the house. People don't understand the basic odds of these things, and 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, holy shit, that's a really bad bet. And I could definitely see that as something you could even commercialize and make some money on. You also talk a lot about risk, which I'm happy to see as well. Several things I noted down that you've written in or said in the past. When trying to quantify risk. And you say things like the worst thing is that you can have an early success because then you think that you are 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 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 how you try to help people understand it better.

I mean, honestly, just because I was an idiot when I was like 23/24. So going back to the trading thing, I won't get into the intricacies of what I was doing, but basically SPACs were a bubble and SPAC warrants, which were like call options, the 5-year expiration date, were also the bubble within that bubble. And long story short, I just got really good at figuring out which ones are going to pop off before they did, just from like being on the internet too much. And it was easy. So I turned $6,000 into $400,000. And after I got to about $150,000, I stopped trading warrants because they were like, they could go to zero. Warrants have no floor price. SPAC shares before the merger actually happens, there's a floor. You can actually calculate how much you can lose on any trade because you can redeem that SPAC for $10 and change. I get up to $400,000 where I'm being meticulous about never having a trade that I could lose more than 5% on. Once the price went up 25 or 30%, I would sell. 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. 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'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. And he was like, you're a fucking idiot if you don't sell at least half of that. 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 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. I can get a couple that work well. In hindsight, that was just the stupidest, like, that's an unbelievable sentence to say. And I felt completely fine saying that because again, I did have a method that was like, even in hindsight, like 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 it's 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. 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 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 a year and a half. So I knew in the back of my head that there was technically risk there, but I didn't think they were going to miss earnings by 30% on their first earnings report as a publicly traded company. Completely blew it. And then I cashed out and just took a week and just left that money in cash, my brokerage account. And then I ended up putting it in a couple of 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 human psychology, 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. 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 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 separate from it, it was absolutely insane to be that young and risk that much money on something stupid. I didn't need to. I had so much money I could put and 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. 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 a million or $2 million, because I probably never would've started writing. I would've been insufferable and thought I was better than everybody because I traded stocks better than everybody. I would've gotten absolutely wrecked at some point. Maybe not financially, but something would've happened that would've fucked me up at some point after that because the hubris I had from that. So losing $150 grand isn't great, but I'd consider that it was a price worth paying compared to like how much worse it could have been. 'Cause 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. Whenever stuff's going good now, I'm always thinking about how could this fuck up. How do I keep that from happening? I'm better because of it.

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.

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 long-only quant algorithmic investing going into the crash of 1987. 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.

Oh wow. What would you have made if you kept the position on for another day?

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, it was the best thing that could have ever happened to me because I would've been insufferable.

For sure. Oh, for sure.

I would've been just a complete ass because I would've thought, look, I made this fortune because all you idiots didn't understand the market was going to crash. 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. Fear, greed, hope, and ignorance are the Four Horsemen of the Investment Apocalypse. Man, everybody falls for them, me included. And one of the things that that experience really cemented in my mind was I am not immune, 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. 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 in travel. 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, 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. 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 I spent the first leg of that trip 4 months in Europe and 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. Southern Spain has notoriously difficult Spanish to understand. People from Colombia and Mexico struggle and Lufthansa, 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. 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. That was the number one spot. Argentina was phenomenal. The people were great, the food was great. Because it was one place that I actually kind of lived for a little while, I actually got to like experience 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. Argentina was freaking awesome. It's very weird because Buenos Aires is a, especially in the better parts of the city, is super nice. 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 Colombia or some other places, but their economy sucks. So they're 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, well-known place for like $12 with a bottle of wine. It was crazy. I guess I spent like maybe $3,000 in 2 months and I was balling out down there, but it was just cool. 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. 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 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. It didn't even look like the same planet. 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 a Viking descendant. Like, it looked 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 phrase to use. But as far as just seeing different people and just a completely different place, Tromsø, Norway, and then Japan. I went to Japan for the first time this past spring. It was just cool, like sumo wrestling tournaments. The food was phenomenal. It was the most culturally different place. 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. You don't have to speak Spanish to get around down there. Japan was a different world. So Japan, Tromso, and then Argentina would be the three.

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

It's nuts.

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

Oh, of course.

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, cuz it's such a like refined culture, but in a couple ways it's not. They don't talk about it, but it's completely normal for people to just get 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 buttoned down people. And nobody talks about it. That blew my mind. I don't know, that 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 yeah, the lack of English over there shocked me. But the language is like learning Spanish from English. It takes about 600 hours of concentrated study. Japanese is like 2,200 hours, 3.5 times, 4 times more difficult than like a typical romance language. So It makes sense, but super cool place.

I love Japan and I love the Japanese. And again, it speaks to the more you travel, the better, because the more you can learn and the more you can learn how even places like, say, Tokyo, which seem like a different world, you do not only notice the differences, but the commonalities that we human beings share, regardless if we can't speak to each other or Our cultures are very different. Well, this has been a blast, Jack. 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 Beehive?

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

I had him on the podcast.

He's the man. He's so funny. 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 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 Denk, 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 we're doing a business deep dive, a Packy McCormick style one on Beehive when they were 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 seems like a better product plan. And then knowing how he'd basically scaled, he was kind of the main guy behind Morning Brew's growth from 50 or 100,000 to a couple 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, 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 everything from cross-recommendations to all the landing page customization 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 going to hit everything they said and they've crushed it. Awesome.

All your stuff is over there. Young Money. And on Twitter, what's your handle on Twitter?

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 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 that is that we're gonna play a game and we're gonna make you the emperor of the world for a day. You can't kill anyone, you can't put anyone in a reeducation camp. But we are gonna hand you a magical microphone that you get to speak into and you get to say two things into the microphone. And what's gonna happen is whenever the 8 billion plus people that occupy this particular rock wake up in the morning, they're gonna think that the two things that you said were their own ideas and they're gonna immediately act on them and start doing them. So you're gonna incept them. What two things are you going to incept in the world's population?

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

I like it. Well, Jack, this has been a lot of fun. Really enjoyed it, and best of luck to you.

Thanks, Jim. Appreciate it.