#268: Jack Raines – Meeting His Heroes, Losing $150,000 (In A Day), & Internet Dopamine

So I'm ready to get started if you are.

Yeah, let's go.

Yeah, I mean, we're basically into it. Yeah. Jack, thank you so much for coming on the podcast. I'm so grateful for you and I want to just acknowledge you for a second because you're somebody who I've seen slowly rise up the ranks in terms of newsletter writing, Twitter. And I feel like in the past 6 months you've really started to find your voice, find who you're trying to be. And I'm excited to dive into your whole journey to hopefully inspire people to do the same.

Well, dude, I appreciate you inviting me to come on your show because I feel like we are very much in like a similar spot. Like we've got trajectory, got momentum. It's like I'm not where I want to be yet. And I know you're not where you want to be yet, but it's cool seeing like both of us on the rise. Hell yeah. So yeah, I'm really happy to be here.

Hell yeah. So let's start with the humble beginnings when you had 900 Twitter followers, 400 email subscribers, a plane ticket to Barcelona, and no writing routine whatsoever. Take me through what it felt like then and then contrast it to where we are today.

So I guess for a little bit of context, because that's a pretty like out there, out there humble beginning. I graduated from college in December of 2019, had majored in finance and Spanish, got a job working in finance, but I had gotten accepted to business school at Columbia University. But it was contingent on me working 2 to 5 years beforehand. So my plan the whole time from when I graduated in 2019 was work a few years and then travel for like 2 or 3 months that summer before school starts. COVID hits right when I start working. I had a very fortunate run on the stock market, like a lot of people did during COVID where I made a couple hundred grand and we hit August of 2021. And I know I'm going to Columbia for business school in a year. And I was getting called back into the office for my job, and I honestly just didn't need the money before starting school. And I'd been, you know, sitting there in an apartment for 18 months, and you're just stir crazy. And I really leaned into the idea of going and having as many fun experiences as possible. And then I gave myself 1 year to do that, knowing that I would go to business school after that. And get my life together in New York in 2022. So I found a plane ticket to Barcelona a little over a year ago for $300 and just quit my job and hopped on the plane. And I was just going to write a travel blog about everything that I was doing in Europe or South America or wherever else I went. But I also wanted to make some money while I was traveling. And while I had been trading stocks during COVID I also started writing occasional articles on Seeking Alpha, a finance kind of stock picking site, and I was making maybe $120, $150 per article based on clicks. So I applied for a lot of writing jobs with like Morning Brew, with a couple of VC firms who were looking to bring on some written content, and nobody would hire me because I didn't really have experience. You know, like 10 articles about why you should buy the SPAC when it was a horrible thing to buy. Really wasn't enough to get like an actual like full-time gig. So that's how I started my blog, which has gotten pretty big now, Young Money.

When did that start?

I started that in July of 2021, I think. And the intention was write this for 3 months, get a portfolio of maybe 30 articles, and then reapply for like a full-time writing job and then do that for a year before business school. Like the entire thing was just going to be a gap between when I quit my regular job and when I start grad school. So yeah. And then now we're here where I'm really planning on making the writing thing like a full-time career. I've got— I went from like 200 readers on my first article to 22,000 now. So it's, you know, one year later, it's pretty interesting.

It's insane. It's insane growth in almost basically a year and a half. And it's like you started from the place of like just having an interest and inclination If you were to go back and go back to July of 2021, what would you have done differently to get to this place faster or to enjoy what you were building?

I honestly don't think that I would do anything differently because so many random small things happened between then and now that kind of brought it to here. Like there's been so many just you know, you have a random Twitter conversation with somebody and then you share a piece of your work and then they share it and that like gives you 200 new subscribers in a day. Or the most random one that's paid the biggest dividends was I messaged Liquidity, which I'm repping my Liquidity hat right now.

For those watching.

Yeah, for those watching. But for those who don't know, Liquidity is a big finance meme page with like 300,000 followers on Twitter and 800,000 on Instagram, something like that. But he had this finance newsletter called ExecSum that had, I think, 90,000 or 80,000 readers at that point. And I just messaged him. It was about a month after I'd started my blog and maybe 3 weeks before I was flying to Barcelona. And I just said, "Hey, I like your content. I saw you have this newsletter that you put out every day. If you need help with it, I write a finance blog. I'm pretty I know how kind of this whole digital writing media thing works. Here's some of my articles. If you like my content, let's chat. So we get on the phone and he tells me that he is basically, he ran the meme page and then he realized the newsletter would be a good way to monetize it, watches the newsletter and the meme page is a really good top funnel to get newsletter subscribers. And he had quit like a private equity job to essentially run this meme page. So I started helping out with the newsletter and I still edit the newsletter now. But again, that was one of those just random kind of serendipitous things that just happened because of a Twitter message. And that played a big part in showing me like what you can do with a newsletter, like how you can actually make it a sustainable like business. And a lot of stuff that I've done since then have kind of stemmed from that. So again, I wouldn't change any one thing because that probably changes something else down the road that might end up with me not being here right now.

Who were the early inspirations for the newsletter and building it into a writing career?

So there's two that really stand out to me. Um, Tim Urban, he writes the Wait But Why blog, and then Morgan Housel, uh, finance author and partner at Collaborative Fund, who wrote— he wrote, I think it was the best-selling finance book of last year, The Psychology of Money. But I really like both of their writing styles. They're a little bit different. Tim's a little bit more sarcastic. He draws a lot of little animated pictures and all of his stuff. But he just started writing a blog about stuff that interested him. And like, why do we procrastinate? Like, how long is the human life actually? Like, should you cryogenically freeze yourself so you don't technically die? Just, you know, very random things that might be a fleeting thought for the normal person. He would just dive into it and write 4,000 words about it. And he has like 600,000 readers. And then Morgan, like finance is such a, such a normally very boring topic to write about. And Morgan was one of the few people who took a very qualitative, almost sometimes philosophical approach to a normally quantitative boring field. And he would relate like the concept of risk in financial markets to how two of his friends when he was a kid died in a skiing accident, and that could have easily been him.

One of my favorite articles of all time, by the way. I'll link it below.

Yeah, it's, it's a phenomenal piece. Um, but those two were two writers that I really liked. So when I was starting my blog, again, I didn't know if I was going to write about like personal finance stuff, such as should you use a Roth IRA, should you rent or buy a home, or go into more content like that, like more abstract stuff. And it hit me that I really liked reading Morgan's stuff and Tim's stuff and, you know, just random pieces from random people on the internet that were more just opinionated, but they had that personal touch to them. So it hit me that if this is what I like reading, this is probably what I should write. And I think that whatever you're doing, whether you're a writer, a podcaster, an athlete, the best way to get good at it is try to emulate somebody really good and then inject your own personality or touch or whatever to that. You can see it in sports like Kobe Bryant, like almost carbon copy of Michael Jordan, but it's a little bit different. Like that idea of copying the greats and then tweaking it to fit yourself is, I think that's the best way to go about getting better at anything.

What's it like then to go and have lunch with Morgan Housel?

So that was pretty wild. I always thought for the last year that Morgan was, he was kind of the guy that I thought has the coolest job in the world. Like he wrote a book, He writes a blog. He's a partner for a VC firm, but his entire job duties are to just write stuff. And then he gives speaking engagements at conferences and for different companies. But we followed each other on Twitter for about a year now. And after I moved to New York, I just basically messaged him on Twitter and said, hey, if you're ever in New York, I live here now. Would love to grab coffee or grab a drink. And he was in town to speak at— he was speaking at Citadel Securities. And he was free one morning and he said, hey, you can just come by our office, let's grab coffee and chat. And they always say, you know, you never want to meet your heroes because they might underwhelm you. But he was a very cool, down-to-earth dude. Like, we talked about writing for maybe 20 minutes and then we just talked about random life stuff, funny stuff, stuff that we saw on Twitter. I just asked him a little bit about kind of what he did like day to day, but You know, when you only know somebody through a Twitter lens and then you meet them in person, it's just, it's very interesting now seeing them through that lens of knowing them in real life.

Yeah, it's so true. And also from my own experience, never meeting your heroes has been completely false as well. Like the people that I look up to and I admire have all been great people and I've been so honored. Have you met Tim Urban yet or any other of your heroes or mentors or people who have surprised you in terms of kindness?

So I've never met Tim. I did email Tim and Andrew is his, like the basically kind of the business partner of his or who he's behind kind of the business side of Wait But Why. And I saw that they return a lot of emails, so I just emailed them and I saw that either one of them or both of them had done like a trip to Australia for a year or two after college. And just said basically I was doing this whole Europe trip. I thought what they were doing with Wait But Why was super cool and just kind of wanted to share what I was doing. And Andrew just basically sent back like, good for you for going out and doing it. You're never going to get this chance again. Cool that you're also doing the writing thing. So never talked in person, but it was still cool exchanging an email. And I've done that with a few people like Derek Sivers, Rolf Potts, who wrote Vagabonding, like a lot of people. Will email you back if you just say, hey, I really like your stuff. I'm doing something sort of similar. Just wanted to share. And as long as you don't come off like you're wanting them to promote your stuff, if you're just being like friendly and amicable, people tend to be very receptive to that.

What other tactics could somebody use to help get in the inbox or get a response from somebody they really admire?

So I actually talked to Morgan about this a little bit because I used to send him a good bit of my stuff when I was getting started. but my biggest fear was coming off as like begging or wanting a retweet or a like or a promotion. I would always say, hey, you wrote about XYZ, or I saw you talking about this. I recently wrote a piece about it. Or if I quoted him in one of my pieces, I would say, hey, I wrote this and like mention your piece cuz it relates to that. Thought you would find it interesting. And as long as you are genuinely just trying to share something that you think is interesting, and you find a point where it's also relevant to them by you quoting them or relating their stuff, that's fine. It's when you send somebody something and ask them to retweet it or to like help promote it. Like, I've gotten to the point now that I have a bigger audience, people send me stuff and I'd say it's like 20%, hey, this is interesting, I think you'll like it. And that's good because like I might not have seen it otherwise, but the other 80% is kind of like Hey, would you promote this or plug this in your newsletter? It's like, if you send it to me and I like it, I'll probably include it. I've included one of your podcast episodes. You never asked me to do that. I just liked it and I linked it. But the second that you ask me to promote something, or for me, when I was getting started, if I ask somebody a lot bigger to promote it, it turns that relationship into a transactional thing. There's an underlying, you want something out of this, not you want to connect as people. So yeah, maybe they will retweet it one time, but you're sacrificing a long-term relationship for a very short-term, like a little bit more engagement on Twitter or something. That's, that's not worth it.

Yeah. When I was doing research for this, I heard you say in a different podcast that you would send people things and then when you sent them it, you'd be like, I'm not looking for you to retweet this. I just thought you might find this interesting. Yeah. And what a useful way to let people know, like, Hey, like, I just found this cool. I wrote this, I found it cool. I think it might be helpful for you, but I don't want your engagement or I don't want you retweeting. And then oftentimes I'm sure people did retweet it because you weren't seeking that.

Okay, so you have done your research. That was a very specific anecdote, but Packy McCormick and Nick Majuli were two people where that happened. With Nick, Nick's actually a good friend of mine now. I got dinner with him last week, but he's a finance blogger. An author, and he works for Ritholtz Wealth Management, and he had a pretty big Twitter following, and he writes a lot about how to invest, not actively picking stocks. And he put out a piece about basically the dangers of stock picking and how it's such a— the risk return just doesn't make sense for most people. And I had recently written a piece about blowing $150,000 in a day by actively picking stocks, specifically picking one stock, buying like $300,000 worth of it, and then they had a horrible earnings report. So I linked that piece and I said, yeah, here's my personal story with it. This sucks. And then I messaged him and just said, hey, I'm not trying to promote my stuff, but I thought you would find this interesting. And he sent back, this is fucking nuts. Do you care if I share it? And I was like, dude, go ahead. So he shares it and I get like 200 readers. And then we were just chatting about it and he followed me back. And then we just kind of talked about writing, investing, and he said he really liked my stuff. And to me, it kind of hit me at that point that there is a sweet spot where people that are much bigger than you will genuinely like your content if they can discover it. You just have to be very careful about how you promote it. So then Packy McCormick, another pretty well-known writer in that tech finance space, He writes this newsletter called Not Boring where he highlights tech trends, like Web3, crypto stuff, startup scene. And one of his buddies, like a year and a half ago or a year ago, texted him and said, "We should have just bought really dumb stuff this year and we would've made so much money, like NFTs, GameStop, like all that stuff." So I was writing something else and deleted it and just wrote the 5 dumbest ways you could have made money in 2021. And made this fictional scenario where if you put, I think, $20,000 in Dogecoin, GameStop, an NFT of a rock, Donald Trump's SPAC, and one other thing, you would've made $250,000 or $300,000, or no, it was in the millions. You would've made millions total. Oh my God. And I just replied and said, I thought this was a really funny scenario, so I wanted to write about it. And He said, this is hysterical. And then he shared it. And I was in London at this point. This was like last November. And he shares it. I go to visit one of my high school friends. She's doing her PhD program at Oxford. And I don't check my phone most of the day and then look and I have like 500 new readers, which was like, I had 600, 700 readers total at the time. That was absurd in a day. And MarketWatch had picked it up. Because a podcast, one of the, I think it was the Animal Spirits podcast that the Ritholtz guys do. They had picked it up because Paki tweeted it. So it was like Paki tweeted it, Michael Batnick and these guys saw it, and then somebody from MarketWatch saw it, and then they reposted it on MarketWatch to millions of people. And that was when it hit me, like, this is how distribution works. You just have to get your content in front of the right people without coming off as overly promotional. So just there's no perfect way to do it, but just write good stuff and then make sure people that you want to see it would actually like it and it fits when you introduce it. Yeah.

It's incredible how you've used that network to win the great online game, as Packy McCormick tweets and talks about. But I want to talk about, you mentioned you just, you lost $150,000 in a day. I know you've gone into the story, But first of all, how do you gain all that money? And then how do you go about losing some portion of it? And then how do you go about deciding you were going to stop? Because I'm sure a lot of people are hearing this like, I made hundreds of thousands of dollars in a short period of time and then I lost a bunch. I know you've spoke about in other places, but we got to go into this. What exactly was that feeling like from your perspective?

So the way that I made the money was, um, a lot of people made and lost a lot of money during the COVID stuff. And it's like, a lot of people were stuck in their apartments, financial markets are crazy, so everybody's trading stocks, crypto, NFTs, whatever. And right when the market crashed, I had been reading WallStreetBets like everybody. I was bored. I was applying for jobs in January of 2020. I missed that initial Tesla bubble and stuff like that, but I saw people online making a ton of money. And as a 22, 23-year-old kid, I was like,, oh, that could totally be me. It can't be that hard. This idiot on Reddit just made generational wealth off of hitting a button on his phone. So I get hired by UPS as a financial analyst in Atlanta, Georgia, and I start my job, and then I see all this COVID stuff in the news, and I just put $10,000, which is all the money I had, in SPY puts. And for a brief primer, puts are options that make a lot of money if a stock drops. Calls or options to make a lot of money if a stock rises. I was gambling. I was playing roulette with the stock market, and the market did drop, and I made $30 grand. So then I put all of that money in more put options on the day that the market bottomed. So I lost all of that in 4 days and went back to $10,000. So I basically round-tripped. No harm, no foul. I'm an idiot. Let's stop. So I put $6,000 in a Roth IRA retirement account with the intention of buying blue chip stocks like Apple or index funds like the S&P 500. And then I hear about this thing called a SPAC. I don't want to get too technical with this, but basically companies usually go public by hiring a bank to help them price their IPO or initial public offering, and then they sell some shares to investors and then they're publicly traded. Some new investors buy those shares, the company raises that money, and then they trade on the stock market. A SPAC is— it's a special purpose acquisition company. It's essentially a bank account that's on the stock market where if they raise, say, $300 million, they'll sell 30 million shares at $10 a share, and then that SPAC is worth $300 million, and they'll go out and find a company. In this case, DraftKings was the first one I heard about where DraftKings was going public through a SPAC. The SPAC called Desert Eagle Acquisition was giving DraftKings, I don't know the exact numbers, but say $400 million to take them public at a $4 billion valuation. So if you bought this Desert Eagle stock, once the deal closed, you would own DraftKings. Cool. So it seemed interesting. So I watched it, the merger happens, and I noticed that there were these things called warrants that were also attached to the SPAC, and warrants were like call options. They were a leveraged bet where Stock goes up, the warrants probably go up by a lot more, but regular options expire in a week, a month, a year, depending on which one you buy. Warrants don't expire for 5 years. So it hit me that if I found a SPAC that I thought was going to go up a lot, I could buy a ton of warrants and I didn't have to worry about them running out of time before the stock price went up. So it was a lower risk way to get a very leveraged bet. Then SPACs ended up being a bubble where all these electric vehicle SPACs were going crazy and sports betting SPACs and all this stuff. So I knew it was kind of dumb, but the other thing was with SPACs, if you bought the shares, you could redeem your shares for $10 cash until the merger closes. So the warrants were a little bit riskier, but the shares, if you got in cheap enough, you could know exactly how much money you were risking on any trade. So long story short, I bought a bunch of warrants in like 6 different SPACs in a row. Nikola Motors, trash company. I knew it, but it was an electric vehicle startup and they were hot. I made like $15,000. Then I did another electric vehicle startup and then another one and then something else. And then I had like, in 6 months I had turned $6,000 into $150,000 in my retirement account. So I was worried about like blowing it at that point. So I started buying shares. Instead of the warrants because I could calculate how much money I was risking on any trade. So I would go all in on some shares at like $11 a share if I could get in early where I'd only be risking a 10% loss. If it would get to $15 or $16, sell all of it and then reload it. So I got all the way up to $400 grand in about 9 months. So my dad calls me because I told him what I was doing. He said, "All right, you have got to take some chips off the table. You just made—" $400,000 hitting buttons on your phone as a 23-year-old. This isn't normal. You won. Your retirement's set. You could cash out $100,000 to go do whatever you want and put $300,000 in your savings. And I told him that, well, Dad, I'm up 6,000% right now. If I go up another 150%, I'm a millionaire. So I don't think that that'll be that hard to do. And I should have known right when I said that, That was just an obvious peak. So the way I lost the money was the SPAC bubble tanks. I don't lose that much initially because again, I knew how much money I was risking on every trade. But when you go from making $20,000 a day to being flat every day for like 3 months, you start taking on more and more risks. And I ended up putting a lot of money into a company that used to be a SPAC. It was no longer a SPAC because the merger had closed. So there was no floor. I could lose all of my money if it went to zero, hypothetically. And naturally I put all my money in it because I thought I knew the company so well. They had a terrible earnings report and I lost $150,000 in a day because, well, that, that was just a possibility at that point. And I thought I was smarter than that.

And so you lose 150 grand in a day. And when I heard you speak about it on another podcast, you said it actually wasn't that bad in that sense of like you dealt with the situation in front of you and then you just had the greatest 3-hour workout. Afterwards. Correct. Take me through that day and what it feels like and how you're able to reprogram your mind into, oh, okay, this happened and now we got to go to the next thing.

Yeah. So it was last August and at this point I had already planned on traveling Europe and stuff and was planning on probably cashing out of stocks around that time anyway. But it was very hard to make myself do that because I was so plugged into that game. I'd been trading pretty much every day for the last 14, 15 months. So I'm in Pittsburgh visiting two of my buddies and I wake up that morning, the earnings report had just come out and I was in the red bad, down $100,000 before the market opened. And I knew it was going to be a free-for-all as soon as it opened and there were more traders could trade. So it hit me right then that, all right, I'm still up a lot. I'm still up over $100,000 from this initial buy., and that's still a ridiculous return. I did the math in my head, say the market has average returns from there for the next 40 years. I'm going to have a tax-free $2.5, $3 million in my Roth if I stop right here. Yeah, it would've been $10 million if I would've gotten out at $400,000, but whatever. If I keep trading and I know that I don't have an edge anymore, obviously, because I just lost $150 grand, sure, I could maybe make the money back,, but I want to go to Europe in 2 weeks. And if I'm worrying about the stock market, I won't be able to enjoy my trip. And there's a distinct possibility that I could actually blow all the money and go back to zero, which would make this whole thing a waste of a year and a half. And it just hit me. It was like, you have money, like it, it sunk cost fallacy, right? It just hit me that I can't think about what I used to have and try to make it back. I have this money, I have no edge in the market anymore. I need to just stop. Throw it in an index fund and not think about it anymore. So all that went through my head in about 5 minutes before the market opened, and I just put in an order to sell all of it at about the price it was at, order filled immediately. And then I just went to the gym and probably had the best workout of my life, 2.5 hours, came back, told my buddies I wasn't trading stocks ever again. And I think we went to a Pirates game that night or something and then went out afterwards. That was it. That was just It was done. Started planning my trip and ended up writing a blog post about that like 2 weeks later because I had started Young Money maybe a month before that.

Wow. What I find so amazing about it is the ability to regroup and recalibrate because that 5 minutes where you said you flipped your entire perspective could have been 5 years for some people.

So I think it was in the back of my head. I always knew, like, or I had known for the last 6 or 7 months that I needed to stop. Like even when I made all the money, it would be like a brief dopamine hit of, holy cow, you made all this money today. But then it turned into, because I was doing it so much, all of my, I was obsessed with it. Like all my conversations would go back to the stock market. I would wake up in the middle of the night and check futures. Like it was the only thing I could think about. But while I was making money, it was just so like, it was like a drug. It was like ecstatic. Like I couldn't, get away from it. So when I lost the money, it was like the pain from that was enough to like make me like, like as Eminem says, snap back to reality. But actually, and it was like, dude, you're being a dumbass. Like, like you're just gambling. This is— you haven't been able to fully appreciate any other aspect of your life. Like, like me and my girlfriend had broken up before this, but like we were— there was like a 9-month period while we were still dating and I was like all my conversations with her were stock stuff, with my friends, with my family. I hadn't fully engaged in any part of my life for the last year, and it's because this was such a big distraction. I made a lot of money, but it was probably a net negative for me as a person. So losing the money was actually kind of cool because it gave me a way to— it was a really good way to just get out of the market for good.

Yeah, that makes sense. And it's funny now because you're dealing with dopamine hits in a different way now, which we can get into where it's like before it was about the money and now you've had two viral threads that have been crazy bonkers, millions of impressions just for your satirical writing on Twitter and LinkedIn. Yeah. What's the similarity between the dopamine hits you're getting from the Twitter writing versus the dopamine hits from making all the money?

So it's, I think it's different because I think money has such a strong grip on us as people. It's like our lives are almost, especially in America, it's like, like money's this big game that you're trying to win. Right. And when you're making that money really quick, it's like winning the best game ever made because like you're making a lot of money, putting forth minimal effort. And for, I was good at it for just long enough that like it was seducing me. I put out a couple of Twitter and LinkedIn, like you said, satirical pieces that have done well. But for me, it's just kind of funny. It's a game in a good way where it's like, wow, this piece is blowing up because I made— so for reference, I posted a piece on LinkedIn essentially saying a personal finance hack is to go to random hotels and walk in and pretend that you're a guest and eat free breakfast and free lunch and then sign off on a random room number and leave., and it's obviously a joke, but it's just real enough. And some people are just bad enough at understanding satire, especially online, that people who think it's funny like it. People who think it— I'm just a thief, comment on it, repost it, say this guy should go to jail. Somebody tagged the police, 3 hotel chains, and Columbia Business School where I'm a student, basically saying that I should go to prison. And when they do that, their entire audience sees that, oh, this is a funny joke. And it's even funnier because this person didn't get it. So it becomes this flywheel of funny satire. And like, I engage in it a little bit too much, but also it's because with the stock market, if I'm not constantly watching it and something happens, I could lose money. Like, I haven't felt the need to check my phone while we're in this interview. I'll look at it when I'm out and it might have like another 500,000 impressions, but it's just like a funny joke to see how it's blowing up. But I'm not risking money from this. It's just like, wow, look at how dumb this is on the internet. So the dopamine feels good, but I don't risk any loss, so I don't feel compelled to be checking it as much. Yeah, that's interesting.

And you mentioned you have some systems in place that you, you use to make sure that the dopamine doesn't hit you because I'm sure a lot of people listening are, are gonna deal with some viral moment in their life. So like what have you learned to pass on?

So I've realized that when I'm sitting down to write something or work on anything on my computer or phone, I can't stop myself from checking Twitter. Or occasionally other stuff, mainly Twitter. So I found this app called Freedom, which you can get on your computer and on your phone, and you can put websites and apps that you want to block for a specific amount of time. And then you can't— I have it set where I can't unblock it. Even if I reset my phone or laptop, it stays blocked. So if I need to work on something for 3 hours, I block everything except for Spotify, maybe a few other sites for research purposes, but Reddit, Twitter, LinkedIn, Instagram, Snapchat, TikTok, all of that's blocked until afterwards. Or if I'm out with friends and don't wanna be checking my phone or not be engaged, just block everything for like 8 hours. And it's been a huge life hack for me. The fact that I'm paying somebody money because I don't have the willpower to stop checking my phone is a really funny concept, but I think a lot of people can relate to that because we live in such a digital world. So for anybody who is stuck just doom scrolling on their phone. It's called Freedom and it's great. I love it.

Was there any significant moment for you when you went from being somebody who was consuming all this content to eventually creating it?

Yeah, it just hit me one day that I'm addicted to the internet, which means there's probably billions of people addicted to the internet and somebody's winning this addiction. And it hit me that what if I just monetize my own dopamine addiction? So like the Twitter and LinkedIn thing, yeah, I'm getting dopamine hits from that, but I've also gotten thousands of new followers and about 400 new newsletter readers by plugging that stuff at the end of it. Nice. So it's like, yeah, it's, it's not great, but also I'm net benefiting from this by getting more readers, which will help me make more money because my audience is bigger. So I'm essentially leaning into the fact that I love those dopamine hits, and producing content that will hopefully go viral. So like, instead of just getting dopamine hits from reading stuff, I'm the one creating it.

Wait, so how many— I want to break down the numbers here for one second. How many impressions did the viral tweet get of the LinkedIn post?

On, on Twitter specifically, I think it's hit probably 7 or 8 million impressions now.

And you only got 400 new newsletter subscribers from that 7 to 8 million impressions. Yeah.

So, so that's like, that's a terrible conversion rate, right? It is. It is. But it also, it also took me maybe 5 minutes to write the whole thing. So I look at the conversion rate based on time input, not total impressions. But yeah, true. As I figured out that if I write a thread or a post on LinkedIn that's like about financial markets or career stuff or whatever, and then I say, I wrote more about this here, and link an article that I wrote, even if it gets maybe 20,000 impressions, that itself could drive 100 new subscribers. But when you post like satire and then you say, here's a blog, some people check it out because they think you're funny enough and they want to see what else you wrote. But most people, there's no connection between blog and that. So I'll usually link my blog on stuff just to have more endpoints, but I don't expect that to drive like 5,000 new subscribers in a day.

That's fascinating. 'Cause what you're saying is that the informational post, the educational posts do better in terms of actually gaining subscribers than a satirical post that gets way more viewership.

Yeah. And that, that brings up a good, just general point for social media stuff that people don't get. Everybody's obsessed with audience building and getting a lot of followers and stuff like that. And you'll see it on Twitter, on LinkedIn, on TikTok, on everything. There's certain trends that pop off, like On TikTok, it's whatever dance video or dance routine is hot, people implement it and make their own touches. On Twitter, it's writing a thread about different Google Chrome extension hacks or productivity hacks or whatever. And people will do these things that I consider them to be very kind of low IQ moves in that you're just copy pasting something that you saw work. Because you know it'll work for you for a little while. But when you do that and then you try to funnel that engagement and you might get more Twitter followers from that and try to funnel that to your product or your course or your service or your newsletter or your podcast, if there's no correlation between what drove the engagement and your main product that you want to funnel it to, it's not gonna work. Or you might get people to sign up for your blog initially, but then they won't keep reading it because they followed you for these life hacks and now you're writing about finance or travel. Like, why would, why would they stick around for that? That's not why they followed you. So a lot of people have these massive social media audiences that are kind of worthless because they can't, they can't do anything with it. And I think people miss that because you can build an audience really fast with these hacks, but it's a terrible audience to build because it doesn't— like, they don't actually care about what you want to show.

Yeah. And I think you've done a great job by focusing on your creativity. Yeah. And really asking deep questions of yourself and writing something that only you could write. And it's shown because people really resonate with your message at a deep level. You have like 26,000 Twitter followers, but 21,000, 22,000 newsletter readers. Yeah. That's an interesting insight because you would expect it to be a lot less than newsletter readers to the conversion. But you've done interesting things on the side. You've you've helped your subscriber growth in different ways that aren't obvious at the surface. And you've built a, a real audience of people who care about what you have to say. And I think it's, it's a credit and a testament to your own internal look at what can I write? Yeah. And what is important to me? And then reflecting on that and asking questions.

Yeah. Like I, I don't want my niche to be any like, oh, just personal finance or just this. Like I want my niche to just be me as a person. Yeah. So, When I tweet stuff, like the sarcastic stuff, I kind of alternate as a person between I can be very sarcastic or very thoughtful just depending on the scenario. So what I write about will sometimes be a complete joke, like I'm obviously messing with people, or it'll be something in depth. But my online persona, it might be a little bit more amplified, but it's the exact same version of me as you're getting right here. It's just I'm not going to try to appear to be something online that I'm not. And even though you build your brand slower, like you said, the size difference between my online following, like social media following and newsletter, is almost 1 to 1. And it's because you're getting the same stuff on both of them. So that conversion rate is going to be pretty high from if you want to follow me versus if you want to read more of my stuff. Hell yeah.

So I want to talk and dive into some of the writing because I mean, some of the stuff I'm sending you last night, texting you and being like, yo, this is amazing. I've never thought about this like this before. And I think it'll be very valuable for people who are listening as well. So this is from Jack's piece called The Case for Traveling More, and I'll link it down below. And this is a quote from Jack: In his 20s, Steve Jobs spent months seeking spiritual enlightenment in India. After college, Jim Simmons tried to ride a moped from Boston to Buenos Aires, though he only made it to Bogotá. At age 25, Phil Knight embarked on a year-long trip around the world. How unfortunate that Jobs, Simmons, and Knight decided to spend time traveling in their youth. That must be why none of them achieved meaningful success. Taking a few months to see the world won't hinder your career, but never taking the time to explore will starve your soul. In an era where travel is both cheap and convenient, a refusal to venture beyond your geographic boundaries is a declaration that you believe What you are currently doing is more valuable and enriching than engaging with the experiences and perspectives of approximately 8 billion other people. I've never heard it like that. I've never heard travel in that way. And so how does that statement land on you today after all your 26 countries that you've traveled to and your widespread writing?

So first of all, I think I need to get you to start narrating all my pieces because that sounded way more profound when you read it than when I read it in my own head. But yeah, for me, I think travel is a very, very important thing. But my travel could be a different thing for different people. It could be starting your own business, learning a new language, just taking any kind of risk that goes counterculture to what is normal. But I think the problem is we were kind of trained this way from high school and from college. Like every single step you take in the early part of your life, is to get this stable job and do this and do that, right? And we keep telling ourselves, well, once I make this money, or once I get secured financially, then I'll do that thing. And then we keep finding some reason to push off that thing that we want to do because the timing isn't right. So everybody, I think pretty much every young person has at least a little bit of wanderlust where they would like to go out and see the world or rent a van and travel around the US with their friends or just go do something a little bit different, but they just keep telling themselves they can't do it. And I think I might have quoted in the same piece, it's from Rolf Potts' Vagabonding. There's this little story about these desert monks who aren't allowed to leave their monastery, but they want to go travel. So they just tell themselves in the summer that they'll go in the winter, in the winter, they'll go in the summer, and they do that 40 years until they die. And I think we're guilty of that, where we have these dreams and aspirations and we just tell ourselves the timing isn't right and push it off into some abstract, indefinite part of the future. And we think that we'll do it later. But the two issues with that— well, there's three issues with that. One, the future isn't guaranteed at all. Not to be nihilistic, you have to FOMO into everything now,. But if you keep pushing something off indefinitely, you could die. Or on a lower level, once you have a spouse and kids, and if you have a mortgage, like at 24, I didn't have any of those things. If I lost all of my money, I could come back to Atlanta, drive for DoorDash for like 4 months, go to business school, and then get a job. The floor when you're young, before you have those responsibilities, is you can just figure it out. It's not going to set you back that far. Once you get those other responsibilities, it actually gets harder and harder to do that. So, you know, there's just— we— I think people don't realize that there's only a certain amount of time to take certain opportunities. And the other thing is there's a lot of like fun, reckless, interesting stuff that could be perceived as riskier, whether that's starting your own business or living abroad for 6 months or whatever. That you can do now and find a real sense of enjoyment, like, like hostel hopping in Europe, or like, like crashing on different friends' couches in different cities around the US, or sleeping under the stars for a few nights. It's an adventure in your 20s, but if you're in your mid-50s, like, you don't want to go hostel hopping or like go out clubbing, or you might not be able to take that financial risk of starting your own business because you have a family relying on you. And you can't retroactively capture that thrill from your youth later by doing those same things. Because just because you have the same objective amount of time, 3 months or 6 months, the experience or satisfaction you get from how you use that time is very age dependent. Like when I'm older, I want to enjoy a lot of experiences with my family and doing stuff like that. When I'm younger, I want to have a lot of fun stories to talk about around the campfire. Like when I'm with my friends, when we're in our 50s, you know, when you get that order backwards, that's what I think causes a lot of like anxiety and regret.

Yeah, I remember hearing Rogan talk about how when he was at— people admire him now for the risk that he took when he was younger. And someone who's 50 trying to be a comedian is a lot different than somebody who's 20 just doing their best to make it happen. And it just made me think about how we often don't think about the importance of starting things when we're young. And a lot of people who listen to this podcast are 18 to 35 and they're in the beginning stages of their life. What advice do you have to that person to get them over the hump of doing something that they know they should be doing?

I think that in general, whenever there's that thing that like Steven Pressfield's wrote about this a little bit, written about this a little bit, but the more pushback you feel, like the more risk you feel from something, the more hesitant you are to do it. That's the thing that you need to do because it's very easy to get locked into your routine of just going about day to day because it's easier, it's inertia. But that thing that you feel compelled to do, but you keep telling yourself you can't, it varies from person to person, but that's usually a very good sign or inclination that you just have to go do it. And I don't really have any advice on how to get about doing it. You literally just have to dive in. I played football in college and we had to take ice baths a lot and that sucked. And there's no way to mentally hype yourself up into getting in a cold tub of water for 8 minutes. You just get in and then you're there and then it's good. It's the same thing with this. You just have to dive in and take the risk. What's the worst that's going to happen? Tim Ferriss wrote about this a little bit before he went on his trip down to Argentina. But if you really draw out what's the worst case scenario, I quit my job, I go try to start this business, or I go to travel, and then I run out of all my money. I could go work at a hostel for a little while. I could bartend. I could go back and get a regular job because I still have the skillset in data analytics or whatever that makes me employable. So when you realize that your worst case scenario very likely is just going back to where you are right now, but just 6 months from now, but with 6 months of good memories, then you realize you're actually kind of already living out the worst case scenario. So you should probably try to do the other thing that has more upside. But you have to really think that through. And I think most people just kind of, they think it's too risky to take that shot when the real risk is never taking it and then never having an opportunity to take it. So you just have to jump in. That's the advice. Just go do that thing.

I love it. Well, you certainly jumped into the writing career and I want to talk about how you write. That's an article you sent me that you'd love to discuss. And here's a quote from you, another one. The two most important inputs for any writer are the things you read, especially books, but interviews and articles are useful too, and the experiences you have. I can't emphasize this enough. Every single thing that I have written has been inspired by a life experience or a piece of content that I've read. Yeah.

So there's— I think that that's probably the most important takeaway I have on the creative process is that you can't just conjure up all of these original ideas in your head. Especially maybe a fiction writer can, but if you're writing opinions and trying to write nonfiction stuff, if you have a blog or a podcast or anything like that, you have to have good inputs to pull from. Because if you're just doing the same day-to-day routine forever and you're not doing anything new, you're gonna quickly run out of content to pull from. Like how many times can you rehash something like, say that for example, I was a financial analyst. Say I just did that and then went out with my friends on the weekends and did the same thing, went to college football games, went to Atlanta Braves games, and that was it for 3 years. Those experiences are pretty homogeneous. Like, there's not that much I can pull from. Um, but as soon as you start reading more books, listening to more podcasts, consuming more information from that was created by other people then you can kind of pull from their stuff and it combines with your experiences. So then you have new experiences where you travel to new places, you work different jobs, you meet new people and engage with new people, you learn new skills. Like whenever I'll just get on this idea of I need to know how to do something, like I'm a terrible dancer. I took swing dancing lessons for 2 months in Atlanta. I took salsa lessons before I went to Argentina. I've been taking like, been doing online Spanish chats a lot to try to improve my Spanish. And you start gaining just random inputs from those things. And then when you least expect it, you could be at the gym, you could be walking around town, you could be eating dinner. Something that you read will combine with something that you worked on will combine with something else. And all of a sudden you have this idea for new content. And that's where all my ideas come from. Like, I never have brainstorming sessions or anything like that. I have like a backlog of 120 writing ideas. That I have saved on my computer of just random things that all hit and maybe they tie in with some current event and boom, there's a blog post idea. For example, when I was flying back to New York, my mom got married this weekend. So mom, if you're listening to this, congrats, you and Chad. Congratulations. But my mom got married on Saturday and I had a pretty turbulent flight back into New York from Atlanta yesterday and it was just like chop suey basically from being over DC for that last hour to New New York, and it hit me that this sucks. You're just stuck on this plane. It's turbulent. I hate turbulence. As someone who travels a lot, I just absolutely despise it, which sucks. But I was thinking about that and then thinking about financial markets, and it hit me that rationally, I know that this plane isn't going to crash. Rationally, I knew that my market outperformance wouldn't last forever. But when you're in that heat of the moment, your emotions don't give a shit about logic and rationality. You're so caught up in that euphoria or that fear that overrides everything. And that's actually what I'm working on for my piece tomorrow is using that as an analogy for investor behavior. But again, if I wasn't on that plane, that idea doesn't hit.

Yeah. It's like there's so many moments that go on throughout our day-to-day life. And this is what's been so fun about writing my newsletter as well is I get to capture those moments with little stories and little ideas that can then be out there for other people to grasp onto as well. And so that's the beautiful thing about being a writer is like you can take these stories and help other people. And I think that one of the best signs of a good piece of creation is that it helps somebody else create something as well, right? Like if you just think about like basic YouTube tutorials, you create a YouTube video and from that the person can then learn something new or create something from that place. But it happens with your writing too, I'm sure, where people will read it and then want to create their own blog or they'll create their own post or build. And I love when people take this podcast and create something from it. So yeah, I mean, I just, I think the most beautiful sign of something being created well is that it helps someone else create something as well.

I would, I would say in addition to that, if it makes somebody take action on something. So I've had people that have emailed me saying that They read this and also like, I'm not advocating for everybody to quit their job and just go backpack Europe. That might not be responsible, but I've had a lot of people that have emailed me and they were in a dead-end job and they took this risk with going to work for a startup or for going to take a trip that they wanted to, or for just taking that risk or doing that thing that they have either procrastinated on or hesitated to do. And they took action because of something that I wrote. So that's like the other side of that is just making people do something, whether it's create something or make a decision or make a change, is I think a sign of good writing.

100%. What's it feel like when Tim Ferriss mentions you in his newsletter to over a million or 2 million people?

Yeah, that was pretty wild. So I had been trying to get better at learning Spanish. I studied Spanish in college. I was okay at speaking it. Majored in it, but I didn't speak it at all during COVID just because I just didn't. You're caught up in COVID, you don't really do anything. So when I was in Spain last fall, I quickly realized my Spanish sucked because I went to get dinner with the family that I lived with when I studied abroad, and I was communicating with them at probably a poorer level than their 2-year-old grandchild. So I was looking through resources on how to learn foreign languages. And Tim Ferriss had written several blog posts on how to do it, and he learned German from scratch in 3.5 months to the level that he gave a pretty good speech or hosted some event for a book signing for his book tour, and it blew my mind. And he had methodically broken down most effective ways to learn it. So I just wrote a blog post pulling from what he wrote, a few other sources, and my own experience on just a very detailed, like, hey, if you want to actually learn a foreign language to get to the conversational level in say 4 to 6 months, here's how to do it. And I tweeted about it. I wrote a Twitter thread on it and wrote a blog post about it. And I just tagged, like, hat tip to Tim Ferriss for the inspiration on some of this. And he retweeted it, which was cool. But then yeah, in his Five Bullet Point Friday newsletter, I was in Vegas on a bachelor party with some buddies and woke up and saw that I had like 1,000 new subscribers overnight and didn't know what happened. And 2 people texted me and said, yo, Tim Ferriss shouted you out. This is crazy. Like, dude, you're in the Tim Ferriss newsletter. So that was up to that point, especially that was the like coolest moment of fame ever. And the fact that he didn't even link my newsletter, he linked a thread that indirectly linked to my newsletter and it still drove that many subscribers was just nuts.

You've done such a great job of getting the attention of people in, in the high-up places and people who have the audiences and leveraging their audiences for your own gain. I mean, I haven't seen an example of anyone doing it better. And we spoke about some of the ways in which you've gone out, gone about doing that. What else comes to mind in terms of getting on the radar of the biggest names in your space as possible?

You can never predict, like you can never really know when somebody that's a big name is gonna share your stuff. But what you can do is constantly be in their ballpark or in their area where like if you write something that mentions somebody else, just tag them in it. Yeah. If you write something, like I said earlier, that you think is relevant to somebody else or that they would like, you can send it to them. And just keep sharing as much of your stuff as possible on whatever medium you use. As a writer, Twitter and LinkedIn are the best, but like YouTube and YouTube Shorts or Spotify or TikTok, like there's different platforms that work depending on what your content is, but you honestly just have to put a ton of stuff out there and just keep proactively putting it out there. Um, that's it. There's not— you can't really— it's just part of the game, right? You can't really growth hack any of this. Like, I've been writing this blog for 16 months now, and the first 6 months I was just shouting into a void and nobody heard it. I know you've had like similar experiences with a podcast. Like, you just have to do something for a really, really, really long time, and then one day it just clicks. Um, so again, the biggest thing to me is you don't want to sacrifice authenticity for short-term growth. Like, it's, it's good and it's okay to tag people and mention people, but you don't want to like come off as desperate. It's like, it's like as a dude when you're trying to like, like if you're interested in a girl, you don't want to come off like, yeah, you have to like initiate action, but if you're sitting there just like blowing up her phone or coming off as needy, it's not going to work. It's the same thing with trying to get attention online. If people view you as somebody who's just desperately attention-seeking, they won't care about your stuff. So like you have to be proactive, but you also have to be smart about not just begging for attention.

When you were first starting out, what were some of the metrics or the things that you needed to hit every week, the actions that you needed to take yourself every week where you're like, okay, I'm going to publish blog posts this time, this time I'm going to tweet this amount of time. Did you have anything like that where people could use that to inform their own journey right now?

For me, it was just, I need to put out 2 pieces on Young Money every week. And I didn't hit that every single week while I was traveling, but there were probably 2 weeks out of the last 15 months where I only got one out in a week. So I put two out every week. And then I had that separate travel blog where I literally documented, I've documented everything I did abroad for the last 15 months, but every 5 or 6 days I wanted one of those to go out. Sometimes there'd be a bore. In Argentina, I was in the same country for 2 months and there were some weeks where I was riding full-time at that point where I just didn't do that much interesting stuff. So I might summarize an entire week in a shorter thing, but like at least once a week put out a travel blog piece, twice a week Young Money stuff, and then share all of it on Twitter and LinkedIn. And that was it. And then there were other derivatives that came off of that. Like I didn't have like a metric that I was tracking, but just proactively talking to people on Twitter or whatever that I think might be interested in my stuff. But the biggest thing was just keep producing stuff. And I also wanted to try to read a book every week, which I was pretty good at for a while, just to keep new inputs flowing on stuff.

Yeah, that's certainly helpful. And when you look back at those books that you read, what were some of the most impactful or what made the biggest impact on your own creations as well?

Vagabonding by Rolf Potts was a big one. That was the book that led to me quitting my job and just traveling. It was probably one of the few books that actually led to a— I've had a lot of books that have made me rethink how I do stuff. It was the only one that made to me actually taking action on a pretty drastic life decision. But that was a big one. Greenlights by Matthew McConaughey was a very big one on just kind of like— he's probably one of the most interesting individuals of the last 50 or 60 years just in general, and both his outlook on life and his ability to almost lean into that fear or to just go take what he wants was pretty inspiring. Those were two big ones. And Man's Search for Meaning by Viktor Frankl. So Viktor Frankl was an Austrian psychologist or doctor who— he was a Jew and he ended up getting thrown in Auschwitz concentration camp. And his entire family died in the Holocaust, but he lived. And he wrote a book that was broken down where half of it documented his experience in the Holocaust and half of it was about man being able to find meaning or purpose despite his circumstances, hence the name. And I read that book about 3 days before I went to visit Auschwitz because I wanted to see— like, you can't retroactively experience somebody else's true experiences. But reading a history book is a lot different from reading somebody's actual personal account of what happened. So I wouldn't say that book caused me to take action on anything, but as far as a book that emotionally moved me, nothing else comes close.

How do you want to be remembered?

That's a good question. I don't really think that much about how I want to be remembered. I think the idea of a legacy or all of that is kind of fickle because At some point we all die and we don't exist anymore. And I think if you live your life trying to build a legacy that you get remembered by, that's a really good way to not actually fully enjoy the life that you're living. I don't know. It just seems like, why would I focus on how people think of me when I don't exist anymore? But I guess if I did try to say how I want to be remembered or how I want my legacy to be, just someone who pursued what he wanted in life in general. I think that's probably a— yeah, just as someone who had goals, had stuff that they want to do and went out and did it. And somebody who didn't live their life in accordance to somebody else.

Well, you're certainly living that right now. And before we come to a close, this hour's absolutely flown by, but I'd love to ask about a challenge you could leave people with to help them in their own life. A lot of times we focus on creating the content, but we don't think about the person listening and them taking some action. So is there a challenge that comes to mind where you could help people in any way?

Yeah, I think, I think just do something that scares you. Um, it could be taking a trip, it could be like trying to learn a new skill, it could be speaking in public, but just if something scares you, if you're terrified to do it, to me, that's a very good sign that it's something that you need to do. So whatever that thing is that you keep finding reasons to put off, just do it. Like, as soon as you have an opportunity to do it, do it. And once you do it once, it gets easier to do again and again. But yeah, I think that's the best tip I have, best challenge I have for anybody.

Jack Raines, YoungMoney.co, @jack_raines, @jack_raines, excuse me, with the underscore. We'll link that below. Thank you so much for taking the time. You're the man. I appreciate you.

Hopefully the first of many. Yeah, of course. I'll have to come visit Austin sometime. Hell yeah. Thank you, Jack.