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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.
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 cost or even thinking about them.
Because I was 24 and I was doing that.
You're healthier, easier to get around, more malleable, but it's still a thought out window.
Like you don't have peak health forever.
Memento mori, I think is a good practice, right? Think it's morbid.
I think it's quite liberating.
The like 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 by product of your environment, like where you fit in in the like 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.
Just like the essentially try 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 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, right? Beehive.
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. Ah. Thanks, Jim. I appreciate it.
are also a full-time MBA student at a little place I've never heard of, Alumbia.
Is that even an accredited business school or no?
Um, the business school is the undergrad had um, there was a little fiasco there.
I think the business school is still accredited though. Still accredited? Okay.
Well, so but you're doing MBA correspondence course, right? Yeah. Yeah. 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. Uh, I love your stuff.
Uh, I particularly love your LinkedIn jester mode, uh, 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 uh, the pandemic, you took 6,000 bucks and turned it into something like 400,000 trading uh, in SPACs and and other uh, instruments.
Uh, you you you 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 a 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 what's your origin story?
If we're if we're going to make sell this tomorrow, man, you better have a good one.
Um, 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.
Um, my origin story is that I'm from Tifton, Georgia.
Um, we're the reading capital of the world.
You can 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.
Um, small town, like 20,000 people in Southwest Georgia.
Um, I played football at Mercer University, small division one school about an hour south of Atlanta.
I always wanted to play the University of Georgia, wasn't big enough, fast enough, strong enough, or good enough to play there.
Mercer was a good consolation prize.
Um and then I moved to Atlanta for 3 years.
I worked in corporate finance for UPS there.
Um 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.
Um and yes, so I 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 um doing all of 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 uh uh color though if we're going to sell this bad Of course. All right.
Um so, let's let's let's go in on the color.
Uh you you write and say lots of really super interesting things that um I want to talk about today.
The first one is about opportunity costs.
And and you make the uh the you 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 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, um 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.
Um 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.
If 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 can 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 I mean 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 they're 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 and 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.
Um like in Bill Perkins' book Die with Zero he directly talks about his roommate doing a trip like that at 24.
But Bill didn't go on cuz 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 cuz he didn't realize what the trade-off was.
Cuz it's like it's really easy to see how much stuff cost 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.
Um and because you can't really see those like you can see dollars in the 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 spider web strength.
And 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 I've long maintained that anyone who can in their 20s, if they can live in New York City, they should live in New York City. Yeah.
Uh 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.
Yeah, places in Europe you can.
I talk a little bit about the hustle hopping though.
What what was give me like What what are the five things you still like think about all the time that you learned on that that one-year trip around the world?
I think there's this like there's this idea that people have out of like going to Europe or whatever and finding yourself and I I think that's a lot of [ __ ] I don't think you can go find yourself in like a like a nightclub in Budapest or anything like that.
But something that I did realize once you get out of your like home environment, for me being 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 you that were like a byproduct of your environment, like where you fit in in 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 to hostel hopping, but you do get a lot better idea of like the what stuff you did was actually stuff you wanted to do or what stuff you valued.
Um and then I think it's uh it's 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 my like I had this idea going into uh like in 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.
Um 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 and had 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.
Um 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.
And 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 like I have four friends in London that I only know because we're in a hostel together.
So the first tour that one it 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 in the hostel thing.
Um the like the speed at which you can make good friendships and how you can kind of skip the whole [ __ ] like surface level like the like in the US there's like an appropriate level of you can't talk about really deep topics right away with new people cuz 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 uh an interesting dynamic.
And it's also like it's 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 another thing.
Um like some people are snoring, coming in late, coming in early.
You'll have uh I had a French guy in a hostel room in Seville, Spain, that brought a girl back to this 10-person hostel, which is just a completely heinous thing to do. Um but I don't know.
It's it's cheap, and then you also the 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 little 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 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.
Um it's cheap, and you're just a lot more adaptable than you would think.
Those are the Those are kind of my big takeaways.
Yeah, Mark Twain said travel is fatal to prejudice, bigotry, and narrow-mindedness. 100%.
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.
Uh the author who I love, Robert Anton Wilson, talks about this quite a bit.
And one of one of the prescriptions that I agreed with when I was young, uh and agree with now even more so, is that if if you can successfully um through travel, through like reading uh things that you normally wouldn't read, or even on social media.
I I you know, if I was not lazy, I would have an alt that would uh subscribe to all of the people who I disagree with.
As it is now, what I'll do is I'll I'll go over and and spend a day in their world uh just to try to figure out what the [ __ ] is going on inside their head.
And sometimes I'm successful and sometimes I'm not, but often times 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 know 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, uh, discussion, debate these days is is 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 I know it's true, right?
And and so I think it's great to be able to, you know, build arguments based on data, things like that.
Um, and you know, where appropriate.
Um, one of the 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.
Uh, 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 lights were 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 and like they're on a very nice cruise ship spending like I don't know how much students were in the Mediterranean. They
They can't actually do anything with it.
Um 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.
Um and like it's something that I've talked like like I'm very fortunate that all my grandparents are still alive.
It's something that I've talked to them as they've gotten older just in 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 trip she does.
Um 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 have the like the energy and the ability to like go do all the stuff.
Like when 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 and I was doing that.
Like you just like you're healthier easier to get around more malleable.
Um so the 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.
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 like 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
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 have peak health forever.
So yeah, it's probably that.
And and memento mori I think is a good practice, right?
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 it helps you prioritize.
Like do I really want to die doing this?
Yeah, and no, that's real.
And and you'd be amazed I'm sure you've experienced it.
You'd be amazed at how much stuff that just eliminates from from even you considering doing it, right?
Like yeah, no, I don't want to die doing this.
I you know, and and it it also speaks to your attitude about grind culture.
Um talk to me cuz you've written a lot about it. I like what you write.
Um What is going on and that seems to be kind of a universal thing.
It it started as the Protestant work ethic, right?
Uh 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 and you seem to be far more inspired by the journey, by the experience, by doing things as you just said.
Uh things when you're young, take advantage of that.
The ability uh to to do that in good health.
Also things like, you know, I can't remember whose whose 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 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 billion.
You you you can you can use this time to like just do crazy stuff if you want.
Um talk about grind culture and and why is it so renowned?
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 [ __ ] I I think part of it is like there's I don't know.
It 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 trying to let them eyeballs so like people who are in money tight situations look at that like the opposite of what they have and therefore kind of like inclined to lean into it.
Um my my general take on like the hustle culture stuff is that like the idea that you have to choose here's 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.
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 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
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 truth 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 cuz 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 in a lot of in a lot of endeavors, and a lot of them is 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 and then a year later you'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.
Um 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 can 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.
If they want to change, you can you can do all sorts of things to help them, but like if if not, it just doesn't matter.
And and it seems to me that everyone's looking for the list, right?
Here here if I do these 10 things that I will succeed.
I think like that is the biggest pile of horse [ __ ] 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. Yeah.
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 [ __ ] 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 like you and Trung are pretty good friends.
Trung writes brilliant threads.
I think he's one of the best.
Um 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 problems and your [ __ ] Like these guys were peddling web 3 tokens 3 months ago.
Uh no, I like I I don't dislike threads.
I think threads can be great.
Um So uh I I completely agree on on the idea though that if you want to 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. Yeah.
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 is all about the disconnect, right?
It's all about about the ooh, I did you know, that's the whole classic setup of a joke. Yeah.
Uh you know, you did not see that coming.
So so let's shift gears now to to something that you do that I I really love and and I love I admire your balls for doing it.
And and that is the LinkedIn pranks.
Tell Tell Tell our listeners and viewers uh about some of your favorites and and what motivated you to actually begin these things because they are like fire and they also go viral, right? Oh, it's it's insane.
Yeah, like they've they'll get like several million views. It's ridiculous.
Um so for like some context for the last probably last year now, I've been like [ __ ] posting on LinkedIn, which is posting stuff that's intentionally over the top, like ridiculously just just not true, but positioned as financial advice, like hustle culture advice, entrepreneurial advice, money saving advice.
Um 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 Lit Lit Itty, 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 then 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 Sub.
Um 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 three 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.
And 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 meeting with HR.
So everybody's on LinkedIn, and they're basically using it to congratulate co-workers on new jobs, and the entire like every LinkedIn post looks like ChatGPT is trying to write a LinkedIn post.
That's 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 real 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 two weeks later.
So the half-life on a LinkedIn post is like 10 or 20 times longer than Twitter.
And three, 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. Um 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 four 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.
Um obviously never did that.
But I mean people in the comments were going going crazy like like go [ __ ] yourself.
Like people are actually writing stuff like this on LinkedIn.
And you see like this person's like a like a VP at Microsoft.
They're telling some like 25-year-old kids who literally like like you're a piece of [ __ ] you should go to prison.
Like how like you can't post that.
Like you're like you are you're missing the this is the joke.
Your coworkers are going to see your comment.
Like you're actually harming yourself professionally.
But then their network see 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 Shapses. She's the bomb. I love her. She's great.
Um but I get an email from her saying, "Hey Jack, this is Dean Shapses.
Um I got an email from a concerned third party about a LinkedIn post you put concerning your behavior.
Um can you come meet with me to talk about this cuz I really just had 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 like emailed back, "Yeah, like would love to come meet on Thursday.
Um just for context, in the last few weeks, I've also said that I got vaccinated a thousand times as a side hustle back when New York was paying people 100 bucks 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 want more student loan debt instead of forgiveness cuz 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?"
Cuz 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, "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 the rip."
And she actually knew exactly what was going on and 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 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 a tele chains.
He's just lying on the internet.'"
And I was like, "All right, that's completely fair."
Um 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 is in April.
We have this cluster cup where like all of the classes at Columbia were divided into clusters in our first semester.
We had a big competition.
Like there's a a soccer tournament.
We have a big like charity auction fundraiser, 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 four beers, four 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 made this ridiculous LinkedIn post about how like after David Solomon, Goldman CEO, has been doing this DJ tour cuz 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 him 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 Westside Highway every morning for four months.
Went out there, smoked everybody.
I mean the comments were insane. Like this is misogynist.
Like, "Oh, is there a woman beer mile, too?" There was.
We actually timed them differently.
So was a pretty DEI event.
Um Well, 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.
Um 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 that 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 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 been it's my favorite thing that I do on Reddit. It's so much fun.
For those who didn't hear me cackling, I think that these are hysterical.
You know, O'Shaughnessy Ventures might do a beer mile. I should.
I think I 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's 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 It's formal name is the Dragon Kingdom of Bhutan, which shows you how badass they are. That's That's awesome.
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 there.
But first, they get massively [ __ ] 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?
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're That's insane. 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 and the people we were traveling with, and I'm like, I Is this really happening?
Like, do you think they're faking the being drunk?
No, because we went early, and we watched them drinking.
And and like it was beer.
I would What our guide was with us, and he goes, "Yes, many of the clients that I take around actually insist on going and and taking a sip to make sure that To make sure they know.
Yeah, that it that it that it that it's really, you know, the doubting Thomas aspect.
But But so the the 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 to put on the the collar of a Wall Street job or an investment banking job or or whatnot."
Or was Was that not part of the thought process?
I think it's 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 or entertaining beyond just like, "Oh, this guy is 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 have like I've met so many random people.
I saw like like I posted some [ __ ] posts on Twitter about BlackRock owning everything and then me actually owning BlackRock.
and like I told Gary Tan see a white combinator follow me on Twitter the next day like stuff like that like he's just terrible. 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 me back the eyeball emoji. Like I love that.
Like okay, I know that he has a great sense of humor off the rip.
Um but yeah, like it's it's both.
It puts me in the 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 want to 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. Yeah.
Uh you know, uh so you get rid of all of those.
Then the people who might get that it's a joke, but they think it's inappropriate.
Uh also people stick up their ass, you probably aren't going to want to deal with them.
Uh so 100% you managed to like sort all of those those types out of the equation.
I love the fact that that you did it on Twitter and that Gary followed you.
It's just terrible, 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 I got so many other things going on called the great reshuffle, right?
And 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 and and it also for anyone who's looking, you can see the the of the handmaidens in the legacy media writing all the stories that like why don't she just announce bought and paid for by, right?
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, right?
So you know when they're walking into Congress, oh here comes GE or Blackrock and Yeah.
and oh look they're talking to Goldman.
I wonder what they're going to talk about over there. And Yeah.
and like it it it 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 the man in the gray flannel suit is just isn't going to cut it in this new world. Yeah.
And and I do you find that is there an age thing going on here?
Is it mostly old bucks like me who are getting all setting their hair on fire about it or or are young people too?
Um definitely old folks like you for the most part.
Um but no I I I think I think the kind of reason that it happened is like COVID kind of like like we were talking in the very beginning about how people kind of get so caught up in life and 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 [ __ ] 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 this stuff physically can't be done remote is [ __ ] 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.
Um but it's 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 subs are 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 [ __ ] that other people don't have to go through the same like grind or same process they did to get where they are.
Like now there's other paths and might piss you off if like you spent like age 25 to 45 going through a lot of [ __ ] to get where you are and then you see this like 26-year-old kid who realizes he doesn't really have to.
Um 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 uh from from the point of view of a mostly entrepreneurial asset manager, I just did not understand the culture of investment banking. Like No.
it it and and so like I would genuinely, no [ __ ] 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.
Uh 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'd really really get I hated it.
And so we caught up and like he was he he was like, "You were absolutely right."
And because essentially his senior uh banker tortured him for his entire time training.
And and he he finally had a uh conversation with the guy saying, "Like do you enjoy like do you really confront her?"
He's like, "You do you enjoy torturing people?
I mean, does it give you pleasure to make me show up at 5:00 a. m.
to do the PowerPoint and [ __ ] like that?
And the guy looked at him and in all sincerity said you know, no.
But I had to go through it, so [ __ ] 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 hated and that we inflict on the people behind us because goddammit, 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 a pretty good piece about this.
We're 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 and has no idea what they want to do.
That's when 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.
Um 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.
I mean, the idea that people don't like to work, like this whole quiet quitting, it's it's [ __ ] 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 file is right on a PowerPoint or it's like like oh no, like the color code is like 1/10 of red 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 work 80 hours a week cuz 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 4:00 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 or 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 and they are doing like a just ridiculous variety of tasks.
Where like people with like PE firms and smaller niche teams that are just doing stuff that's not the standard like [ __ ] Um, so I mean I I feel like with business school I've had a good sample of students and 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 like financially similar outcomes, why would you do the one that sucks? So I think
So I think that's going to force a cultural change cuz like top achievers are just going to quit going to jobs that suck if they have another viable option.
Yeah, and uh, is is that something that you're noticing?
Like you have a successful newsletter, right? Uh, Young Money.
Um, and and it one of one of your maxims which I heartily agree with is you you need to be authentic, you need to be distinctive. Yeah.
Uh, the minute you're speaking in an inauthentic voice, it's like the old comms, the old PR models, right?
It was always in corporate speak.
Uh it it was decided and passive 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 Masserburg 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.
And I think I think that people don't And And your gags uh as as LinkedIn's uh resident jester uh really underline how people don't yet really grok how your average human, like they see that as [ __ ] from everybody, right? Right?
And And yet why are you seeing a change among your peers like at Columbia?
So, Columbia's a great example.
Elite Ivy League business school.
Probably a lot of the colleagues that you have there are going to go into I banking 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, [ __ ] 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 well, like people are in like every bank, consulting firm, whatever, all sorts of stuff.
But yeah, there there's definitely chatter of like what did I get myself into, this and that.
Some people Some people love it.
It It And again, there are like it varies from person to person and it depends on like like what company they're with, what team they're on.
Like the the people that you're working with can kind of make or break like it being a fun long work to like the torturous experience like you were talking about with that other guy.
Um but yeah, people are definitely like Again, I can't compare it to how it was 10 years ago cuz 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 you're an 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 I 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 I see it percolating and I'm very hopeful because um you know, the the unlock that we have today.
First off, I think we are incredibly lucky to be alive at this moment in history. 100%.
Um and and the you know, the I the the the people who think they're being romantic saying, oh, but I'd love to go back to you know, the Rousseauian nature. Uh Uh no, you don't.
Nature killed you often and and was really really dangerous in 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 He was born in '21, right? Yeah.
But like Calvin Coolidge who was president of the United States, his son died from getting a sliver from a wood tra- tennis racket because it no antibiotics, went into sepsis, dead. Yeah.
And and and like these people are like, "Oh, but you know, the world is so much with us late and soon getting and spending we lay waste our power."
Yeah, but that was [ __ ] 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?
Um 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 two generations back.
Like that was like stuff like that was the norm.
So, we have like medically and technologically advanced incredibly fast over the last, say, 50 or 60 years.
Um 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 Like 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 the upside now is so much Like the I don't know.
It's 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 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- what to deal with the amount of choice that we have.
And it leads to like a now like paralysis by analysis. It's just a lot.
Yeah, uh 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 a buddy called luck raiser 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.
Um and and you followed a similar idea with with you call it the you you call it increasing luck's surface area.
Talk talk to me about that and 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 in place that like there's a lot more chances to make those almost like accidental incidental connections because there's so many people doing interesting things in a small area.
Everybody knows everybody.
Um but yeah, like New York geographically is a place that kind of increases your luck's 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 at Balthazar like a month ago and I just ran into Howard Lindzon at breakfast and it was a complete fluke thing.
We like interacted 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 [ __ ] posting on LinkedIn.
It was the stupidest conversation ever.
And I ended up going to this like uh not financial advice film premiere at Tribeca Festival.
Like Howard got me a ticket to it just cuz like I emailed him after and 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 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 will start to find you and vice versa.
And then like once like you have like on Twitter for example, if 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.
Um 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 in-person 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 being very successful in a lot of different industries is high just because of where we are.
Uh that's a luck surface area thing.
Like the odds of having a social group that's like having strong friendships with people doing interesting stuff is higher from where I went to business school.
So yeah, I 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 increases out there, I think. Yeah, I agree.
Uh 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 into that movie, but I was like, "Fuck that, Howard."
I just watched it anyway cuz the director sent me a copy of it.
I'll tell you what, it was it was funnier than I thought it was going to be.
He he me about I thought afterwards.
I was like, I actually thought this is going to suck going into it and I was like thoroughly entertained.
So, I had very low expectation.
It was It was a solid movie. Yeah, no.
In In fairness and joking aside, uh I really wanted to go, but I I had an uh unexpected trip to California come up.
Um and so I did get a chance to see the whole movie and I had the same reaction. Yeah.
I love Howard, so the talking about him being a degenerate, even though it's true, uh 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 are they going to thread this needle, right?
Because we don't want to give away the plot too much, but it's it's it's about um the misadventures of people within what we're going to talk about next uh in in crypto, specifically in our friend Elon Musk's Dogecoin.
Let Let Let's spin 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.
I mean, I think it's all [ __ ] I'm like I 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 my dollars to pesos in a matter of minutes.
Um 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 AI 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.
But 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 [ __ ] 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 in an apocalypse.
Like nobody's going to give a [ __ ] that you have a decentralized currency.
Like computers probably won't work.
So I I think it's one of those things where 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 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 Filipino all these people are putting money in to 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. Um I I don't know.
It it's just wild to me that it's like the one thing like the the pushback is always oh there's fraud in traditional finance too.
Lehman Brothers this and that was bad stuff. Yeah, there is.
But like in crypto the fact that like Coinbase is kind of the like air bringer 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 [ __ ] 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.
Like let's find like the only crypto companies that just exchange just to trade cryptocurrencies that have value these 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 500 X to trade cumrocket coin 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 [ __ ] That's that's my that's my spiel on it.
I'm very like loud about that.
I guess crypto people get really offended really easily too.
So it's a fun group to chirp for sure.
Well, you had the you had the remark that you know, stocks are based on, you know, the real economy whereas crypto is based on vibes and narratives and stories. Yeah.
I I I think that I'm I'm trying to remain open-minded to things like use cases for like Ethereum might be a really and blockchain might be really useful actually in AI.
In keeping versions straight, in keeping you know, 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 going to tamper with the models and actually remove stuff that was very useful.
So I think you know, something like you know, a blockchain permanent record would be interesting. Yeah.
But in terms of the the crypto trading, yeah, I 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 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 it's a it's a joke.
Robinhood's a casino, but like, I mean, you get free stocks by doing a virtual scratch-off lot- lottery ticket.
Like, come on, that's like that that that analogy was just very obvious.
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 mean invest. I don't mean gamble.
I don't mean scratch-off tickets or lotto or you know, Dogecoin.
I mean, actual investing.
Um, and and so I I do believe that gamification can help uh, in learning, but it can also hurt, obviously, because you want to if you want to 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. It's incredible.
No clocks, beautiful people serving free drinks.
Um, you know, slot machines that are 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 and yet it is like the saddest thing in the world to me because like the these are people gambling money they don't have, and you know, they're they're gambling, surrendering it to the house. Yeah.
Like, people don't understand the basic odds of these things, and like, I don't want to sound like a scold.
It It would be cool if you could come up with a gamified way for people to understand like, "Holy [ __ ] that's a really bad bet, right?" Yeah.
And And I could definitely see that as um as something that, you know, you could even commercialize and and make um make uh some some money on.
You also talk a lot about risk, which I'm happy to see as well.
Um and and several things I noted down that that you've written in or said in the past, uh you know, when when tried to quantify uh risk.
And And you say things like, you know, the the worst thing uh 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 And And that is that [ __ ] 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 is fascinates me because it 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.
Um talk about what got you off on on thinking and writing about risk and and and how you try to help people understand it better.
Um I mean, honestly, just because I was an idiot when I was like 23 / 24.
I So, going back to the trading thing, right?
I I turn I won't even get into 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 very like the bubble within that bubble.
And long story short, I just got really good at figuring out which ones were 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 like to about $150,000, I stopped trading warrants cuz 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 can lose on any trade cuz you can redeem that SPAC at $10 and change.
Um 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, um 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 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 six 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 [ __ ] idiot if you don't sell at least half of that and just like He's like, 'Dude, you can throw that in the S&P, and 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 three more trades.
Like that won't be that hard.
Like I can get a couple of 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 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 as soon as that bubble popped, I naively assumed that, "Oh, I can find another trend that then make a lot of money on." And I didn't.
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 unlike now and I put like all my money in that and then they completely missed their earnings projections and I would have lost half of my portfolio in a day. And it was the like definition of
And it was the like 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 I I didn't think they were going to miss earnings by 30% on their first earnings report as a publicly traded company.
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 roller coaster the entire like human psychology like every single emotion greed fear luck risk whatever um 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
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 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
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 could happen is winning big early.
The best thing that happened to me was losing that money versus making a million or 2 million cuz 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 [ __ ] me up at some point after that because of the hubris I had from that. So, I don't know.
I mean, losing 150 grand isn't great, but I'd consider that that like a It was a price worth paying compared to like how much worse it could have been cuz the 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 [ __ ] up?
How do I keep that from happening?
And it's Yeah, it's it's I'm 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 worst 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, uh which was um I I would was trading a particular type of system, which was very different than what I did uh with, you know, long only quant uh algorithmic investing um going into the crash of 1987.
And uh I had amassed the biggest put position I ever had uh in my young career. I was 27 years old.
And um I sold it all to basically break even the day before the crash. And Oh, wow.
What What would you have made if you had the position on for another billions millions of dollars.
And and much like you, um at first I was devastated.
Um but as 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 have been insufferable. Of course. Oh, for sure. Right?
Like I would have been just like in complete ass. Right?
Because I would have thought, "Ha ha look, I made this fortune cuz all you idiots didn't understand the market was going to crash."
And then I would have It would have been horrible.
But the other thing it did was it finally pushed me over into being a total [ __ ] because it demonstrated to me that I was not exempt from human OS. Yeah.
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.
And man, everybody falls for them, me included.
And and one of the things that that experience really cemented in my mind was I am not immune.
And and therefore I've got to build a process around the way I make these investments or I'm going to [ __ ] up just like everybody else. Yeah.
So, I think the your you were very astute to see that maybe that was one of the best things that could have ever happened to you uh because it 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 your wanderings and travel.
And you know, what were your three favorite places in your entire year of traveling around the world?
What were the three places that were your either your favorite or where you felt like you learned the most by being there?
Um well, also going into that, I'd 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.
Like, this is what you get for trying to do both.
Um but, my three favorite places, so I Argentina was the place I spent the most time in.
Um 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 Seville, Spain, and got dinner with the 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 in like Andalusia, 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 cuz I was and I was like, like, I would like to be bilingual.
Um 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.
Ar- 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 seeing 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 that 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.
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 the black market.
So, I'm like getting a steak dinner like at a nice like well-known place for like 12 bucks 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.
Um me and my buddy Mike had a a rule where like we would have to go on a date with a girl who doesn't speak any English once a week.
Um 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 cojer in Spain when I studied abroad means to get.
Like I can say like like quiero cojer un agua. I only get a water.
Um in Argentina, cojer means to have sex with and I didn't know that.
So, like I'm in a restaurant and I like straight up told this girl I wanted to [ __ ] a beer.
Um yeah, like there was a lot of that.
So, Argentina was the most like I don't know constructive for me as I actually had to get used to kind of living in a spot like that and it was beyond just doing touristy stuff.
Um 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.
Uh and the hostel owner's name was Robin, super nice guy, like lived in the States for a little bit.
But, we were in 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 in just a completely different place, Tromsø, Norway. Um 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 cuz 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 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.
Like I remember like you can't even figure out how to use a payphone back when I was there the first time in the late 90s and like literally I was helpless.
I was 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.
And and and so but what a great experience and what a great place to go.
So I highly recommend Japan's 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.
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 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 always 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 2200 hours.
It's like three and a half times four times more more than like a typical romance language.
so it makes sense, but super cool place.
Yeah, I I love Japan and I love the Japanese.
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 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.
Um first off, tell tell everyone where they can find you, where they can find your letter.
All and a last question, why did you leave Substack and go to Beehiiv?
Um 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 I 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 to help with his newsletter cuz 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 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 Beehiiv because he knew Tyler Denk, who was the CEO of Beehiiv, previously had been one of the first employees of Morning Brew.
Um so I was on Substack and then Lit moved to Beehiiv and then I have like we're doing like a business deep dive like the Packy McCormick style when I'm Beehiiv 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 basically scaled, but 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 Beehiiv, I just wanted all my stuff in one spot.
Um I'm I'm I'm biased like I guess because I use Beehiiv a lot now, but it was initially a logistic thing and I trusted that they were going to deliver on the road map with like everything from cross recommendations to all the landing page customizations or 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.
And so you're you're all your stuff is over there, Young Money. Uh Yeah.
And on Twitter, what's your handle on Twitter?
Yeah, so Twitter handle is Jack_Rains.
Um LinkedIn, you can just look me up as Jack Rains.
My job title is curator of vibes.
It's my LinkedIn account.
It'll be pretty easy to find.
And then yeah, um my newsletter blog is Young Money. co co.
Um 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.
Um I'm more likely to respond to like DMs and stuff on Twitter.
My LinkedIn DMs are a [ __ ] 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. Okay. 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 you're going to incept in the world's population? Um Shoot, that's good.
I think the I think the first one would be telling people This might be biased cuz being in like 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 uh essentially try to trigger that wake up moment.
Um and I don't know, don't take life so seriously.
You know, just like have fun.
That's the I mean that's the biggest advice I have for anybody. So, yeah.
You don't have to do anything 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.