#96 - The Business & Tactics Of Building A Personal Newsletter Company - Jack Raines

I'm 23, 24 years old, have like $400 grand. I ended up losing like $150K of that in a day. And I was like, all right, I have enough money. I don't have to work for a year. Like I know I'll be able to get a job after business school. So I figured I'll just start my own blog.

You're listening to the Next Generation Podcast, weekly interviews with the most interesting and successful 20-somethings out there.

All right, everyone, on today's episode, we have Jack Raines, the author of Young Money. Jack, what's going on, brother?

What's up, Connor? Thanks for having me.

So, uh, let's kind of kick things off and kind of get a better understanding in terms of your background when it comes to writing specifically. And so, um, I think I found your first post back like July 2021 on Young Money. I think it was something around like writing about Bitcoin back then. And I think your content— and just imagining after writing for well over a year at this point, you've kind of probably shaped it a little bit more towards like the stuff that maybe you want to engage more. You're not just going as traditional finance In the sense of like, that's what you're writing about. I think it was like something around like Bitcoin and crypto in general. Now I'm getting emails from you around like, hey, like what's fuck you money and what is like FOMO investing and all this stuff. And for me, like, I like, I love the voice that you write in. I think it's really, really relatable. So you want to maybe go and kind of let people know what Young Money is and kind of how you got into the newsletter business in general?

Yeah, for sure. So Young Money is, I call it a finance blog, but I say it's like, Tim Urban and Morgan Housel had a baby. I draw a lot of stick figures, do my own art, but I also try to write, I guess, with a more qualitative voice. Finance is a very quantitative numbers field, and honestly, most finance stuff is boring. People don't care that the Dow went up 100 points or went down 100 points yesterday. Nobody really gives a shit about, for the most part, about what earnings multiple Apple is trading at. But what is very interesting is like Bill Wang blowing $20 billion in 2 days, or seeing how like super rich people handle their money, or just basically how people interact with money in their lives. So the human side of finance. And to me, I noticed about a year ago, really a little bit after I started writing it, that, um, like Morgan Housel was probably my favorite finance writer because he's so good at writing, it doesn't really feel like he's writing about finance. He writes about— Yeah, yeah. Great book. He writes about life through the lens of finance. And because I really liked reading his stuff more than probably anybody else's, it hit me that I should probably write more similar to him because if I like reading it, I would obviously enjoy writing about it more. And I kind of, as you said, the first piece was about Bitcoin. For the people listening, it was called Bitcoin or Bitcon, and basically explaining why I do think that Bitcoin is pretty much a Ponzi scheme. I still feel pretty strongly about that. So it was not a pro-Bitcoin article, but I have gotten a little bit away from analyzing individual securities or doing stuff like Roth IRA, rent versus buying a house, to stuff that's a little more philosophical in nature, like, should we really define wealth as just a money thing, or what about wealth of time and knowledge and experiences? So yeah, over the Over the last year, I've kind of gone from that very by-the-book finance to writing about honestly whatever's on my mind, but usually tying it back to finance or career stuff somehow.

And I think when Connor first sent me one of your articles or something, I think his comparison was kind of like a more interesting version of Planet Money, which is a podcast I've been listening to. Yeah, I think that was kind of a good a good explanation, especially with all the visuals. And what was the desire in the beginning? Did you know you wanted to start a newsletter or did you kind of come in and say, hey, I'm gonna start creating content, I enjoy finance, I'm gonna just start writing whatever and then figure out a medium and platform to start the distribution there? Or did you sit down and say, hey, I wanna, I wanna definitely start growing a big newsletter and reverse engineer it out of what you thought people would find interesting?

So I, I never really planned on this thing turning into The fact that 18,000+ people read it right now is pretty wild. My whole initial plan was literally write this blog for a few months to get some writing experience to then apply for a job with like Morning Brew or one of these financial media companies. So for a little bit of context, I got into Columbia Business School in 2019 when I was a senior in college, and it was through a deferred enrollment thing, which basically meant You get in in 2019, after you graduate, you work 2 to 5 years and then you go to business school. Typically it's you work for a few years, then apply. Basically, I already knew I was going to a good business school when I graduated. Like any 22-year-old, I had no idea what I wanted to do, but I figured I'll just work in finance for a few years, go to Columbia, and then like go work for McKinsey or Goldman and make a shit ton of money. So I start working in good quantity, by the way. Yeah, yeah, thank you. Um, so I start working right before COVID hits in February 2020, and, uh, corporate finance job in Atlanta. We go remote like a week after I start working, and then I'm very bored working from home, start trading stocks, and I turned $6,000 into about $400,000 in 9 months, just like hitting buttons on my phone basically.

Um, trading before— oh, actually, you might have just been about to get into it. I would just love to know specifically what you did. I don't even think we have to say this, but I'm going to say it too, just so I don't get a lawsuit, not investment advice. Just—

Yeah, no, this is probably the opposite of investment advice. I was trading SPACs. It's funny now. Chamath Palihapitiya was the king of SPACs back in the day. I just saw on Bloomberg that he's winding down his last two SPACs and returning money to shareholders. That bubble's dead. Like, it's— that's not happening again. Um, but it was a bubble. I knew it was a bubble, but I got very good at playing that bubble, I guess. And, um, like, I actually— I wrote a piece about exactly how I did it. It's literally called How I Lost $150,000 in a Day, because that's how the story ends. But if you want, like, details on, like, the actual intricacies of what I traded, that's in there. Um, but anyway, make a lot of money way faster than I should have. So then I'm 23, 24 years old, have like $400 grand. I end up losing half of it in about a month, um, and like $150K of that in a day. So I cash out and I still have like a good sum of money. And I knew that I was going to business school this August, so now we're in July of 2021, and I was like, all right, I have enough money, I don't have to work for a year. Like, I know I'll be able to get a job after business school. So why don't I just quit my job because I'm bored and just go travel and just do a bunch of fun stuff? So I bought a one-way ticket to Barcelona, quit my job, and I was in Europe from like August to Christmas. But I wanted to make some money while I was traveling, which is where the writing stuff comes in. And I had written some stock articles here and there on Seeking Alpha. They would pay like $100, $150 an article. So I actually applied to Morning Brew. I DM their CEO Austin Reef on Twitter, like sent him a bunch of stuff and he actually replied to me. But I didn't get the job. I applied to 10 different jobs. So I figured I'll just start my own blog and write for 3 or 4 months and then reapply around Christmas time and then see if I can land one of these jobs and do it maybe until starting grad school, maybe while I'm in grad school, whatever. Like I like writing. I thought it was fun. So that was the initial plan. I saw that— this is where it gets weird— Liquidity, the finance meme page. So I saw that he had a big newsletter with like 90,000 readers, and I just messaged him on Twitter and said, yo, I like your stuff. I write a finance blog. If you need help with your newsletter or you're looking at adding some content, let me know. So we get on the phone and he told me how he was doing this full-time because he was making like close to $1 million in ad revenue from newsletter. And I was— I had no idea. Yeah, yeah, yeah. And it— I was mind-blown that that was like a viable business thing. So like I started— like I edit Exact Sum every day now and do some other stuff on there. But that was the first time I saw that you could actually make a lot of money on this thing, um, if you build a big enough audience. So That shifted my mindset from, oh, like write a blog until you can go write for somebody, to write a blog until you don't have to work for anybody ever again. Because with a big enough audience like that, that is a business. You can sell ads, you can have paid content. There's just so much you can do with an audience once you hit a critical mass. So that really shifted my perspective on what this thing could turn into.

All right. I have so many things, I have so many things that I want to unpack out of that. Um, let's go, let's go one at a time because we just went from everything from making six figures in the stock market to Morning Brew to the, the power of newsletters. And I think I'm gonna save the how much money individuals can make off of newsletters as a later point in this conversation, um, because I think that's really interesting. But I would love to, because I think this is a topic you'd like to jam on as well, like What time period did you go from $6,000 to $400,000 via the SPAC investments?

Um, it was around probably from May of 2020 to February of 2021, so like 9 months. Okay, basically like one, one pregnancy.

So one, one cycle. Awesome. Um, and as you were doing that, what was going through your minds, um, like trading-wise and over that 9 months, months Um, I, I was definitely like—

keep in mind, I was, which I'm still, I would say, young at 25, but I was 23, like, he just turned 23. So I just thought I was like hot shit, right? Like somewhere between like Warren Buffett, Michael Burry, um, like Stanley Druckenmiller. Like, I was, I was killing it.

Michael Jordan, Kobe, toss them all in.

Tom Brady, like, yeah, all of it combined. Well, it's like, you know, I have a job I was paying like $60K a year, and there were a couple times where I made close to $60K in like a week just trading SPACs. So I didn't take my job seriously at all. Um, I, I remember, I distinctly remember in February when I was like hitting my peak, and I knew it wasn't sustainable, but I also knew exactly how much I was risking on every trade. So even if it imploded, like, I wasn't going to lose more than $10,000 or $15,000 on any one trade, which is true. The reason why I actually lost the money was I changed my strategy because the SPAC bubble popped and I thought I could make another 150% and get to $1 million, but like what I was doing was working and it wasn't gonna blow up on me. Like it would eventually quit working whenever the stock market got too saturated. But my dad, in February when I was around $400K, like he knew what I was doing. He thought it was kind of funny, but he was like, dude, you need to cash out at least half of it. Like you realize that you literally just made 8 times your salary by fucking around on your phone. And I was like, yeah, but if you made 6,000% in 9 months, you only have to make another 150% and you're a millionaire. And I was like, you know what's cooler than having $400,000 as a 23-year-old? Having a million dollars as a 23-year-old. He was like, you're an idiot. He was right, I was an idiot. I should have, uh, I should have cashed out. Like, but I think that's also the The crazy part there is too, right?

Like the fact that you even walked away with anything I think is a bit insane, right? Your, your whole article on house money and when you make money that quickly, so many people get caught up in, all right, I made, I made $60 grand now, maybe I can make $80 tomorrow. And now, all right, I made $400. What stopped me from making $4 million?

Yeah.

And then 90% of the time you just end up either right where you started, back to zero, or, you know, maybe owe someone money on options or something.

It's because whenever you lose, you make a lot of money and then you lose money, your first inclination is to try to make the money back the same way that you lost it. But if the market was the same in August when I lost it, it wasn't February when I made it, that might work. But the one thing that saved me was after I lost the money, I realized that I lost it largely because the market had shifted, my strategy wasn't working, And like, I didn't have any alpha anymore. There was nothing that I was going to do that like gave me a competitive edge in the market. And if I tried to trade my way back, it would have been gambling and I either would have hit a lottery ticket or I would have lost it all. And that just, that, that was a horrible idea. So I cashed out and just threw it all in index funds. Um, so I was, I was glad that I realized that that was the one, I guess, like little bit of wisdom I had in this whole process was being cognizant of the fact that like, I had fun playing. My game was over. Go find something else.

Yeah, I think there's some crazy stats around there too that like in the long term 95% of day traders lose money, something like along those lines. Like it's definitely a tough business to be in. Um, but when you lost that $150,000, that was over the course of what, a week, a day?

Uh, about 7 minutes.

Dope.

Yeah, it was— I was about to say it was literally this company that used to be a SPAC, which is why I thought I knew it well. I thought it was undervalued and I had all my money in it and they bombed their earnings in August. So that was right before the market opened, that started to tank. And there was just no— I couldn't sell my stuff because there was no trading volume. So I knew I just put in a limit sell around 5% below what the open price was just to get out of all of it. And Like, it worked. I got out with, I guess, a manageable loss because it could have gotten worse if I would have held that day. But yeah, it was— yeah, that was, that was bad.

We're gonna move on to some more of the, like, business actual side of, like, growing a newsletter. But, like, talk me through, I guess, that 7 minutes in that day, because I would imagine it's just probably the most severe form of depression of just being like, this really fucking sucked.

So I was, um, I was living in Atlanta at the time, but I was in Pittsburgh visiting two of my best friends who'd moved up there. And I woke up at like 8:30, saw the earnings report, and my first thought was, oh man, I'm fucked. And I'm like watching the line go down, and my buddy Tucker, like, he was trading too, so he walked out. He was like, he wanted to make sure I wasn't like hanging from the ceiling fan or something because he knew how much money I had on it. He was like, you good? And I was like, yeah, I mean, I like, I did this myself. It's not like this is some major surprise. He's like, what are you going to do? I was like, when the market opens, I'm just going to sell all of it, buy probably an S&P 500 ETF, and going to go to the gym for like 3 hours. Just like, don't talk to me until I get back. So I'd probably have the best workout of my life. And, um, it was kind of like, in hindsight, not nearly as traumatic as I thought it would be because I just looked at it like, well, like, we're done now, we're not doing that again. Um, so yeah, honestly, not, not as bad as you would think.

So many people in our generation, I think, are going to be somewhat desensitized to wild swings of money because they're either playing with cryptos or they're day trading SPACs or I think it's so difficult to, I think if you put yourself in anyone's position 100 years ago, there's no way anyone's ever experienced making this or losing this much money in, you know, a couple hour or minute time span. I think it'll be interesting to see what happens in the next 30 years when we're all older and—

Well, on that point too, I think the other thing that nobody talks about that it's probably worth, just 'cause we have like a younger audience in terms of like how to go make money, There's some fundamental connection between the 3 of us and a lot of people that might listen to this show where they're like, "Everyone just wants to make a lot of money." And that's just the nature of these business podcasts. But because you see people making so much money out of such little money from these outlandish returns on investments, there's this belief that you can start getting crazy reliably rich through investments alone. And I think That's certainly true in some degree. There's angel investments and there's like, sometimes you'll get really lucky and just pick the right thing and it'll go outperform everyone. But historically, typically the way people get rich is you build a business that cash flows and builds up equity, and then you can eventually go and sell something like that. And then you can go and use investments as more of a way to go and compound and annualize those gains versus, hey, You can reliably go throw some money on something that's called cumcoin or some shit like that and go and grow 6,000% in one year. That has worked weirdly enough over the last 3 to 4 years with people buying digital rocks and monkeys. But it's not— I don't know, maybe I'm wrong about this. I don't think it's a good strategy in the next 10 to 20 years.

Jack Raines: No, it's definitely not. I mean, a lot of what you saw was a byproduct of interest rates being zero, so money was very cheap, just like from corporations, like, taking out loans all the way down to, like, kids buying cum rocket coin. So you have that, you have people who are bored because there's a pandemic, they can't go anywhere, then they get stimulus checks, and then everybody's on the internet and it's just so easy to start trading that, like, it became a source of entertainment and there was a lot of free money floating around. Like, I personally think a lot of the crypto space is very much just a byproduct of people just wanting something to trade, and it gave them something to trade. Like, it was just like almost an entertainment venue. Um, and people come up with like narratives like after the fact to support what was going on. But that's— I mean, that's my, my take on it. But yeah, it's like world's going back to normal. You actually, if you want to make money, like have to get a job or do something that provides value. You can't just like press buttons on your phone and become a millionaire. There was, there was a 2-year period to do that. If you did it, great. If you didn't, not going to happen again for at least a decade, so you missed it.

And Connor, I think back to your point too, the odds of A, first making the money in the first place, and then B, selling and cashing out profitably, I think are so low. Even most of the people you've seen that made tons of money in the meme stocks or anything probably have just lost most of it at this point. I think to have the confidence or the balls to finally sell and cash out whatever you want is extremely difficult. But transitioning to kind of maybe that, that actual sustainable business model and, you know, ways to consistently make money rather than betting on the markets, maybe we could chat about kind of the growth of the newsletter and maybe how that the first couple months of A, coming up with we're going to start publishing it, you know, you went from 500 to 2,000 to 3,000 subscribers. Wait, wait, I think you're right.

Well, just let me cut you off. Let's, let's like break down the exact dates of these because this is really interesting. And this is what I think I tweeted.

Sure. I think exactly what we should talk about. But, you know, kind of maybe starting in the beginning, it looks like the growth was somewhat exponential towards the end. So, yeah, I would love to kind of chat about those first couple of months when you only had a couple hundred subscribers and what you're really doing then.

Yeah. So The one benefit of the trading besides making money from trading was people kind of knew me as like a stock finance investing guy. So I put on like Twitter, Instagram, and LinkedIn that I'm going to start a finance blog. People were at least curious enough to see what I would write about. So I got— I started off with about 200 readers, which is going from zero to that without writing anything is like relative to I think most people probably a really good head start because I had some sort of audience that was reading. Um, but the first 2 months kind of sucked because like you might spend 5 or 6 hours writing something and nobody says anything about it, or you can even lose subscribers, right? Like you'll publish and then you'll see like 3 people unsubscribed and now you have 197 readers and you're like, damn, did this suck? And a lot of times it didn't necessarily suck, it's just the people reading it just aren't that interested in this type of stuff. But You don't know why somebody unsubscribes. Like, you don't know if they just— if your writing sucks, if they just aren't interested in this topic at all. I mean, you could be the greatest finance writer of all time, but if somebody doesn't care about finance, it won't matter. Um, so it was like a lot of just throwing, literally just like throwing stuff at the wall and seeing what sticks. Um, but I kind of found my voice probably 2 or 3 months in where it was like getting— like, I just didn't want to be like a personal finance guy that telling people how to use a Roth IRA or if they should rent or buy a home. So I started leaning away from that and tried to do more almost storytelling, either personal anecdotes or stuff from history, and then relating that back to just stuff that's going on. But the one thing that really was kind of the moment where the switch flipped was I had written a piece that kind of covered how I lost all that money., and this guy Nick Majuli, he has like 100,000 followers on Twitter, finance writer, and he put out a thing about, um, a piece on not actively trading stocks and basically like all the risk involved with the act of investing, like how it's just hard to know if you're even good in the first place. And I replied to his tweet and said, yeah, like I've been through this, I actually lost, you know, $150K in a day a few months ago, and I sent him the piece.. And he was like, this is insane. Can I share it? He has 100,000 followers. Like, yeah, you could share it. Please, like, please share it.

He writes the whole like Of Dollars and Data stuff, right?

Yeah. Yeah. Yeah. That's him. So he, he shared it and I got like 100 new subscribers that day and I had maybe 500 readers total. So that was like a 20% jump in a day. So it hit me that I've gotten to the point that I had maybe 20 or 25 pieces written. And there were going to be different times that I could basically integrate or plug something I wrote into a conversation with somebody who was like already pretty successful in this field and basically leverage their audience. The key was you don't obviously want to just spam people like, hey, read this, but when you do see an opportunity to like introduce yourself to a conversation with some of your content when it fits, like do that. So I started kind of keeping an eye out for stuff like that. And you do that enough and then your work starts circulating, and then people like Nick start sharing it. And like, he's somebody that a lot of people trust as a finance writer. So it just, it just compounds. It gets easier and easier to, uh, like get on people's radar.

Yeah, well, I was gonna say, I didn't realize this at all until I hit you up because I started— I don't know how I found your stuff, is probably through some Young Money, whatever. But I was gonna say, you even sent me a cool piece on the dopamine stuff that you did back in like February, and it was like very not— you literally said, here's this piece, you probably find it really cool based on what you just tweeted, uh, don't promote it or anything like that. I just thought you'd find it relatable. And like, from my standpoint, I was like, that's the perfect way to go and start sharing your stuff and like building up an audience in the right way. Um, that makes like a ton of sense to me. And I think the, the piece too that Gio was kind of mentioning before in terms of like, I wish if anyone's— this will go on YouTube as well, but like, I wish we almost had like visuals here. Like, 2 months in, 500 subs, 5 months in, 2,000 subs, 7 months in, 3,000 subs, 9 months in, 5,000 subs. That's like a 66% jump in that 2 months. It took a year to get to 10,000. And then 1 year and 1 month in, you got to 15,000, which is kind of insane. Like that, was there just a crazy promotion in that last, like last month?

So it was this guy, we're like pretty good Twitter friends now, Alex Banks. He put out some thread of like, basically newsletters that he liked, and it just went nuclear. Like, it was one of those where for some reason it just got hot with the algo, and mine was like the third one on there, and I got 2,000 subs in 2 days from that, which was just absurd.

That's amazing.

Um, like, me and him ended up getting on a Zoom call later. Like, he's, he's a cool guy. He's like from London, just got his master's in finance, and he was like, yeah, like, I just wanted to put out a thread of newsletters that I liked, and then it just blew up. And he's got like 70,000 followers on Twitter, but, um, he's a cool dude, but it was, that was, that was pretty unexpected, but it definitely added a lot. But there's been like, there's been a lot of things like that that were unplanned, but just a byproduct of like people reading my stuff and then like leaking a piece on their newsletter. Or if you put out enough content and you talk to enough people and your content is good and people like it, they're likely to share it with their audience. And if they like it. Some people in their audience are probably gonna like it. So like a lot of the growth is really just a byproduct of like putting stuff out there and just sharing it as much as possible. Um, but going back to what you said about like the piece I sent you, I'm very careful not to like spam people with shit because people at this point, like, it's not like I'm a Tim Ferriss or Morgan Housel, but I do have a decent-sized audience now and people know that. So I'll straight up have people like hit me with stuff and ask me to like retweet it or share it. And there's like nothing that makes me wanna read your stuff less than if you tell me to promote it. Like if you send me something and say, hey, I think you would like this, I'll probably read it. If you say, hey, can you retweet this? Like, no, I'm that, that's not like, I didn't get any free clout. You're definitely not getting free clout. Like, and that almost, it almost dilutes like As someone who runs my own account, like, I don't want to just be out here, like, pay for play retweeting people's stuff just because they DM it to me. Like, if you write really quality stuff and you share it, like, it'll work, you know? If you're having to constantly beg people to share your stuff, then the problem isn't the distribution. It's just your content isn't good enough, and people don't realize that. Um, so that's the— anyway, I know that you have to get your stuff in front of people, but I usually like what I did with you. I'm very like Hey, like, I'm not asking for retweet, I just think you would find this interesting because of something that you posted. And that was kind of my— it, yeah, it might be a little bit slower growth, but you're going to make a lot more friends that way, and you're not going to come off as spammy, which, like, in the long game is way more important than getting— like, okay, somebody might pity retweet you, but then you're kind of on their shit list, like, oh, this guy's just, like, begging for retweets, right?

And in, in the end, it doesn't matter how good your distribution or marketing is if the product or content isn't high quality. And I think it also probably forces you to actually find your voice, right? Like had you gotten a ton of growth right in the beginning with some of those maybe more boring articles and content, you probably might have stuck on that route and not really differentiated yourself. And then you don't see that accelerated growth in the end, whereas it just forced you to make a better, you know, better content. On the actual note of making interesting content and getting good content. I'm assuming you, you probably subscribe to a ton of other newsletters, blogs, and you're probably reading and watching and just consuming a lot of content. Do you have a specific strategy now on how you are, you know, looking for interesting things? Is it just part of your daily habit or what are you actually doing on a day-to-day basis to, I don't know, consume and then regurgitate some of this stuff?

It's funny that you say that because I've almost gotten to a point now where I think I've probably written a piece that answers like a lot of these questions at some point. I wrote one literally called How I Write, and I, I hit on that a little bit, kind of how I come up with ideas. But I don't like actively go looking for content to inspire me with stuff. I think that the, the best content is created as like a, um, almost like eureka moments that are byproducts of like the content that you consume and the experiences that you have. So for me, it's It's just like, you know, reading interesting stuff, listening to interesting podcasts, and then just going out and doing stuff and meeting people. Like, a lot of the stuff that I write about just pulls from stuff that goes on in my life. Like, the FOMO piece I put out today, that's because I've been dealing with like an existential sense of FOMO for the last 3 weeks. Like, it was just like I needed to put the thoughts into words. Um, so at that point, it's, it's really just being able to turn the stuff in your head into written content that people would like. And there's not really a magic formula for that other than when you publish like 2 pieces a week every week for like 15 months, you just kind of get— it's like playing a sport. You just get better at it because you've been doing it for a while.

How many hours are you actually spending a week writing or coming up with content?

I have no idea. I literally, because between like writing and then getting distracted on Twitter and then like working on other stuff, I— and then like doing research for it or editing, I can't quantify it because honestly, I don't know. I tried to track it a couple of weeks ago and it just— sometimes I can write a piece in an hour and a half. Sometimes it takes like 7 hours. It really just varies.

You recently came out with a course called The Business of Newsletters, which looks really interesting, especially as people probably listen to this more. And I think towards the end of this, we'll probably talk about the questions of how big can these newsletters get from a financial standpoint and some of the maybe non-financial benefits. Um, but real quick, do you want to just talk about the course? What inspired you to come up with it? And then also maybe what the structure looks like and a few like gems out of it that maybe people wouldn't have expected.

Yeah, for sure. So I, I used to be very wary of courses because I think it's just getting rubbed the wrong way by the amount of guys trying to do like forex or crypto trading courses that you see promoted on Instagram. Um, but David Perel has this course called The Rite of Passage on online writing. And a lot of people that I really respect, like Packy McCormick, have either taken it or have like talked about it and were raving about it. And then I'm friends with Dickie Bush and he has the show 30 for 30 that he does with Nicholas Cole. And a lot of people love that. So it hit me that if you actually like provide value and like both of them are good riders, so they kind of have like the pedigree that backs up their ability to be teaching riding stuff. I think it can be a really valuable thing. And, um, Nathan Ball, he's the guy that I'm doing it with. We actually met in person in Spain when I was there over the summer, and he was living in Madrid. And we had both gotten to the point that we were making money writing online, and we were like hanging out at a cafe and just talking about how there's no real blueprint on how to actually turn on the monetization engine. Like, there's ads, subscriptions, like you can use it to upsell your own product or course or service, but there's just there's nothing that tells people, hey, like, if you have this idea or this, like, content stream, how do you actually go about turning that into a way to make money? So there's a lot of courses out there on how to write, how to get started writing, how to, like, find inspiration for your ideas, but there's nothing really out there that says, okay, like, you have that, now how do we actually make money from it? And so we started brainstorming and put together, like, 70 words in a Google Doc of information on everything from negotiating with sponsors, like how to go about cross-collaborating or promoting with other creators to grow your audience faster, um, like best practices, worst practices for sustainable growth. And then everything from like, like what ad rate you should charge, how to like better negotiate deals, like how to use this to leverage a product or your own business, or how to use your content to like go find work. Like for example, I've had people that have either like paid me to do contract stuff for them or offered me full-time jobs based off of what I wrote. So we want it to be a blueprint of if you want to put content online, here's how you can use it to make money. And it's not going to be like a, like a, like you'll have to put the work in. Like it could take a good year before you start making money from it. But if you follow this and you do put the work in, you're going to be able to make money from how you write. So we almost want to take what all these other guys are doing, with getting people writing and showing them how to actually like make some money from it.

What's one of the examples of the best practices that maybe people wouldn't have expected when it comes to actually creating good content? And I don't know if you have an answer off the top of your head here, but I'm curious if there's like something that people wouldn't think of when it comes time to that.

So a lot of people either go too far one way or too far the other way on the distribution versus the content. It's if you have to have good content or people won't read it, but if you have really good content and don't know how to promote it, people find it. So what people miss a lot of times is people get very good at growth hacking social media like Twitter, LinkedIn. There's templates that work, but if you just follow blindly, follow different growth hacks on there and they aren't related to your work at all— like if you're— you guys are on Twitter, so if you see the people doing the Excel tips or Google Chrome hacks, cool. But if you're doing that and you write about like long-form finance blog, or you write a travel blog or anything that's not related to that, there's gonna be no conversion from like what you're doing on social media to that. So you start building a social media audience completely detached from the like content audience you're trying to get. And that's just like you, you're putting all this work in to build this massive audience that's entirely worthless to you and almost like dilutes your stuff, right? Um, so I think that's one thing, like actually knowing how to build up your social media following, like with your newsletter, your blog, whatever, by making the content completely aligned. Even if it's slower, it's just a lot stickier. Like people are in such a, like such a rush to just get the numbers up as much as possible. They lose sight of like, what's actually going to give me staying power where this is sustainable. Yeah. So that's like when we're talking about marketing, that's one of the biggest things. Like, strategy that actually has staying power.

Yeah, I completely agree. I think you also might've tweeted out your newsletter advertising deck a couple weeks back and I got a chance to skim through that. What's interesting is what audience you're trying to build totally depends on what it is that you're trying to do and how you're trying to monetize things. And so for instance, if you're a real estate private equity guy, you really don't care if a lot of moms from the Midwest follow you, but if somebody who has access to a huge trust fund or like inheritance or like a place like, or just sold a business and they want to go and invest a lot of that capital. Um, like those are the high net worth people that like you really care about relating to. And candidly, they don't give a fuck about like your Chrome tips, right? Like, that's just not why they're like, that's not the content you should be putting out. The content you should be putting out is probably a lot more of like, hey, here's the returns we've gotten investors in the past. Here's our track record. Here's our team, that kind of stuff. What's interesting with you is that like, as you kind of read through like your advertising, um, Deck is like, you're in the finance space, which traditionally charges like a pretty high CPM. I don't know off the top of my head, if I had to guess like $50 to $80 or $40 to $70, something in that ballpark. Um, and so what's cool about that is like, what you care about is you don't necessarily need the ultra high net worth people, but you kind of need the people who are making like six figures and above to like really go and engage with that. Because then you can go and turn around, say to any advertiser, hey, 30% of the people that are on my list make over $100,000 a year. Here's the big, you know, big 4 companies that they work for, etc. And now you can go and charge a higher CPM because it's a more valuable audience.

Yeah. Yeah. And the other thing with me is, and I think it's just a benefit to writing long-form stuff versus like curated stuff. There's obviously there's a market for both, right? Like Morning Brew is a lot of their stuff is curated and it's probably worth over $100 million now. But with long-form stuff, the content circulates more on the web. So I'll have some pieces that hit like 15,000 web views and they get like 9,000 email views. And those web views also drive a lot of clicks. So you can either like do a combo deal where it's maybe $500 flat plus a generous affiliate fee. That way if it pops off on the web, it's a win-win for you and the sponsor. If it doesn't, they don't get hurt by it. Or you can just charge a slightly higher flat rate. Like if you're gonna charge $1,000, maybe you could charge $1,250. And then if it doesn't blow up on the web, you could say, hey, we'll like run another one at a discounted rate. But having that extra web views gives you, it gives you some leverage as a creator too.

And what does your actual tech stack look like between publishing on the web, getting the newsletter out? Is it just kind of, I think what you're on, you're on Beehive.

Yeah.

Is that pretty much it? Are you also kind of working on SEO in the background and doing anything funky with pop-ups and analytics, etc.?

No, my whole SEO strategy is just write good stuff and hope people share it. I'm not like a tech wizard, so it's been working pretty well so far. I think if you're doing, especially if you're trying to like, if your blog or newsletter is related directly to like a service or business you're trying to promote, SEO makes a ton of sense. If you're just literally writing a newsletter for the newsletter, you should really just be worried about the content itself. Um, like, it should be very easy to share. Like, I have, like, subscribe and share links all over my stuff, but I'm not, like, trying to SEO optimize my titles and my words. Like, I just want to write what I think is interesting. Um, but I think Beehive is a no-brainer, best tech stack any creator can use. Like, they just rolled out— which, Substack's had this for a couple of months— but they just added a cross-recommendation feature where you can cross-rec other newsletters on Beehive. So if somebody signs up for Exec Sum, they'll see, you might also like Young Money by Jack Raines. And the difference between Substack and Beehive is on Substack, you're opted in by default and you have to opt out. On Beehive, you're opted out by default and have to opt in. So even though you'll get slightly less subscribers through the recommendation off the bat, it's people who actually want to read it versus people who get default opted in. It goes to their spam folder and bounces. So, but Beehive is— the audience analytics are also great. Like, I can see the acquisition source. Like, I see where every subscriber comes from, like Twitter, they found it direct through Google, an exact same referral, Nathan's newsletter. I get referrals from that. It's, it's just I think it's the best platform for somebody who's not tech savvy or not an SEO wizard like me to be able to track everything. And then it's also just super easy to ride on. So I'm a huge fan. They've been rolling stuff out very quickly, but it's— Beehive's great. I use it for everything.

Yeah, the product is great. I've been messing around with the newsletter myself just to kind of like understand the space a little bit better. And I switched it all over to Beehive and it's been so easy to use. We actually also have the CEO Tyler's coming on the show sometime early next month to jam on that. I'm excited for that. All right. I know we've got like 15 minutes left and I have way too much stuff that I wanna ask. And so one more nitty-gritty question on like how you think about this. And then I wanna kind of jump a little bit more into like the financial side, but how do you think about the difference between like personal branding a newsletter, right? Like I think right now you, You basically market it as Young Money by Jack, or I don't know if it's by Jack Raines maybe, versus just calling it— I know my buddy Alex has one called Marketing Examined, and he doesn't really promote himself a lot in it. Is that something that you've ever spent time thinking about or try to be strategic about? Or I'd love to get your two cents between the two.

Do you know who Jack Butcher is? Visualize Value? Yeah. So he actually wrote a very good piece a few days ago or last week that got into that. But I think about it very similarly to him. A personal brand is very useful in that it gives you a lot of leverage. The audience feels very connected to you, the writer, because it's like they're getting stuff from Jack, not from Young Money. But the downside is, like, I can't sell my blog like a business. Like, it can get acquired, but then I have to keep writing it because, like, I am the value prop versus, um, say, exact sum, like Liquidity's newsletter that I write. Like, that's a Liquidity newsletter. But— and it does have its tone a little bit, but it's also a very valuable resource for like finding financial news. So somebody could acquire that and take it over, and it still probably retains 85% of its value if he's not running it, assuming they can keep growing it. So when it's— when you're promoting yourself, it puts you at the center of it, which gives you a lot of personal leverage, but you also can't really just cash out of it. But you do get a lot of opportunities from it. Like, like people want me to write for them or help them with the newsletter or this or that, but I kind of have to keep running the newsletter or blog until I just don't want to anymore. And there's no real way from a business standpoint to just liquidate that versus the curated one or the like branded one. Um, you can, but then you also don't get as much of the benefit of like having a personal recognition. So it's, it's a trade-off. I mean, depending on what your goals are, both of them can be good.

Yeah, it's more of an almost funnel versus like an equity play too. I guess that maybe I should have said it differently.

What's the ultimate kind of goal here in terms of, you know, you're self-branding it to some extent, but then you're, I guess, not self-branding it as a Young Money one. Do you want to keep pushing that out and then, you know, just kind of make some cash flow on that right now? Where do you view that in terms of what do you think is actually feasible in the end from, from ads? You know, do you want to start other businesses down the road, focus on the content? How do you kind of view this from a longer-term perspective?

It's— I have a very simple view. All I want to do is write, and I want as many people to read my stuff as possible. So I don't want to paywall anything, which means ads make sense. And then the course thing, if it goes well, I like the idea of kind of showing other people how to do this just because for the first 6 months, I really didn't know what the hell I was doing. And it would have been good for me to have had like a blueprint that would kind of show me like what I'm doing wrong, what I'm doing right. Um, but I, I just want to write. And this, like, the bigger your audiences, obviously the more money you can make from ads, but more so for me, it's just, it's cool having 18,000 people that are interested in what I have to say. And I would also like to publish a book or 2 or 3 at some point. And the bigger your mailing list is, the easier it is to convince a publisher to take a chance on you. I've actually been talking to Harriman House. They're the group that actually published Psychology of Money and then Nick Majewski's book, Just Keep Buying. So I've been talking to one of their editors a little bit about potentially doing a book pitch. And I didn't know this at the time, but for them, it's more important to have an audience that's receptive to your book than just being a good writer itself, because it just helps sell books. Yeah, exactly. If you have 20,000 subscribers, one, it signals that, okay, he has to be a decent writer, this many people are reading his stuff. But two, it's like there's a free marketing channel, and if other people who are big in the space interact with you, that's good promotional material too. So yeah, I mean, I, I— it's really just, I don't ever want to have a regular job again. Like, I just want to write stuff and then activities that come from that, like the course, or if somebody wants to pay me a consulting fee to help them scale a newsletter, sure. But I want to keep it simple. It's easy to get over stretched out trying to do a million things.

So on the publisher side, yeah, there's a reason someone like Ryan Holiday is coming out with a new book every single 6 to 12 months. The guy's just pumping them out at this point. But it's interesting. I'll leave some names out of what I'm about to say right now just for the sake of privacy. I will mention one because I think it's interesting. But like one year ago today, like I really didn't, I wouldn't have known at all how big these newsletter businesses can be. And I think it was sometime around last May, I was getting coffee with someone in the space who you definitely know. And he brought up, you know, the Sahil Bloom guy? Yeah. So he brought up his newsletter, just talking about it in general. Like, and what that guy basically does is he just writes about things that are interesting to him, which is like kind of everyone's dream job, I would imagine to some degree. The guy, these are rumors. So like, I don't want to have it totally based on that, but like, um, I was told he makes like half a million a year off of that alone. And I was like, holy shit. Okay. That like changed my perspective on it. And earlier this year I was talking to another friend who I think a lot of people listening to this would probably know, big on Twitter and does a bunch of other content stuff. But like they basically dabble in like every single type of business, like between e-commerce, media, software, like some real estate stuff. Like they're pretty, They do a lot of angel investing too, but they basically brought up that for them, when you look at overall strategy of how to grow personal wealth or grow personal businesses, their whole thing is like, it all starts with content. If I can go and build up my brand big enough, that'll go and do everything for me from bringing me deal flow from new investments, helping me go and hire better, helping me go and get distribution for products when I want to go and launch something new. And so I definitely think that overall, as you see more attention shift from like less traditional media to more like individuals and like individual newsletters and social profiles and all that kind of stuff, that it becomes this like new form of leverage to launch a bunch of other stuff and monetize things in a way that like traditionally you couldn't have done 5 to 10 years ago.

Yeah, no, I'm, I'm, I'm all over that. It's, and I've kind of figured that out almost on accident, just seeing like how my opportunities have grown and just having more and more ideas now of like where I can take this as it gets bigger. But yeah, if, if you have a big following and especially a big mailing list, what people miss is people keep getting caught on the next hot thing like TikTok, Instagram Reels, whatever. The, the two things that are undefeated are a YouTube channel and a newsletter because those are just way stickier subs. And think about it, YouTube has been around since like early to mid-2000s and it just won't die. Like every other social media has died or stagnated at some point. Like TikTok won't be around forever. And those kind of algo-based or feed-based platforms like TikTok Reels, it's, it's a very passive audience. They just see your stuff while they're scrolling. Email has been around for like 40 years. It will literally never die. It's older than any of us. And that's a more intimate connection because like people go out of their way to subscribe. You're in their inbox. Like That's just such a valuable venue and people completely miss that. But yeah, once you have that, like, you can, like, you have an audience to sell stuff to. You can, like, promote anything. It, like, if you can build a mailing list or, like, a big YouTube following, you literally can't lose. Like, you've, you've won the game. It's just defining what game you want to win at that point.

So let's talk about, like, what the next 12 months looks like for you to some degree, just because Okay, we kind of read out like your growth numbers earlier on and it seems like roughly you can get to this point now where like you're adding between 4,000 to 5,000 new subscribers every month. At least you have been for the last 2 months now at this point. And so like if you can go and continue that, and I would imagine maybe even grow that on a monthly basis, like 9, 10, 11 months from now, you're, you're probably gonna be listening. If anyone's listening to this in September of 2023, what's up? But also you'll probably have 100,000 subscribers on this email list at that point. And so you can make some serious money, you'd be making hundreds of thousands of dollars a year just based on the CPM in your space. I guess what I'm curious about from your perspective now is similar to how you were making hundreds of thousands of dollars day trading and working a $60,000 job, why get an MBA right now? Why are you at Columbia versus just going around and talking to a bunch of other newsletter creators and kind of like making this your full-time thing?

So I don't know that I would have applied to Columbia now had I not gotten in 2019, but part of it was I was already in. So I don't want to say it was a complete sunk cost, but like the momentum was all ready to go. That was the whole plan. And I had to put in my intention to matriculate last December, and I didn't have— I was not making much money from writing at that point. So like It was honestly, I needed to at that point, but I still think there's a benefit to it in that for like, we're kind of in the new age internet, but there's a lot of people who aren't, who when they see like people, especially like 35 or 40 plus, they see MBA from Columbia, it signals, okay, this guy knows what he's talking about. So you see the MBA from Columbia writing a finance blog. It's, it just looks a little bit more relevant or significant than random guy who was backpacking South America. Writing a finance blog. When you're trying to write a book, when you have like Jack Raines, MBA from Columbia, like it's easier to market that book through the Columbia network. It's easier to like, it looks more official for the publisher. So there's a lot of brand appeal to both having an MBA from Columbia and being pretty internet savvy in that I can essentially lean into the like, like suit and tie side of finance or the degenerate Twitter side of finance and play both sides. And honestly, dude, business school's fun. Like, it's me and a bunch of people in their mid to late 20s just like, like hanging out, kicking it. But also half of them are gonna be making like millions of dollars a year in the next 10 years. So I don't know where else you're gonna get, like, I think Twitter's a very valuable networking tool. It might at this point be more valuable than my MBA, but getting this many people that have such a high chance of success all in the same place at the same time. And meeting in person every day, you just can't really put a dollar value on that. So I still think it makes sense even if you don't want like a normal job.

The fun side definitely should not be undervalued. Um, the only thing I would say is the only thing that sounds better than Columbia business student is Columbia business student dropout. That might just be a nice, like, fun element to add to it, just as a joke. Um, yeah, no, I just feel like, I feel like every Silicon Valley, uh, uh, like Founders like Harvard dropout, Harvard dropout. It's like you get the same credibility of being like, I went there, uh, then it's like, but we went all in on this other thing. Yeah. Um, all right, cool, man. I know we got like 2 minutes left. Last thing I want to wrap up with is nothing finance related at all. It is, uh, best travel story from the last 8 months in 60 to 120 seconds. What you got?

Um, I got deported from Norway. So how does that— the nicest, nicest people in the world. It's a horrible country to get deported from. Um, so November 2021, me and one of my best friends were planning on going to Norway to like see the Northern Lights, go dog sledding. It's this town called Tromsø, Norway, like 200 miles north of the Arctic Circle. Look it up, T-R-O-M-S-O. It is the most beautiful place on Earth. Um, Norway had a weird COVID rule where they only accepted European Union and British COVID vaccine passes, and they didn't accept the US one. I happen to have a European one. When I was in Switzerland, I had to go to a pharmacy to get some like cold medicine a month earlier, and I like, I asked them if I could get a Swiss vaccine pass because I've gotten denied at a bar the night before my US one. And they were like, yeah, like we can actually just get like email you a QR code if we have your passport and your card. So I didn't, I never thought anything of it. My buddy flies into London, meets me in London, We fly to Oslo, Norway. I have a QR code. He has the paper card. They're like, yeah, like, you have to get the fuck out. You're a health threat. And he's like, you guys aren't even wearing masks. Like, you don't care. Um, so they sent us back to England. So we just go to Scotland for a week and a half, and then when my friend leaves, I fly back to Norway. And I still go see the Northern Lights and stuff, but we did technically get deported from Norway. Um, which was— it's, it's a funny story to tell, especially like if you know anybody from Norway. Very nice people. It was just a really weird law they had last November.

That's too funny. Traveling during COVID or around that timeframe has probably been some of the most like craziest stories I think from other people. And in person, I know Connor and I have a bunch too. It's a wild time to travel.

Jack, it is.

Where, where can people find you online? Follow what you're doing and stay up to date.

Follow me on Twitter @Jack_Raines and then Check out my blog, Young Money. It's youngmoney.co. Um, my DMs are open on Twitter. If you're listening to this, have any questions, want to tell me that I suck, literally anything, hit me with it. I love it. Appreciate it, guys.

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