Hello listeners and welcome to the latest episode of the AdQuick Advertising Podcast, a podcast that explores the intersection of content, creativity, culture—all of the things that you care about. Today we have a special guest. We have Jack Raines. He is a rising star in the world of finance and blogging. He writes at Young Money. You've probably seen his posts with the fun cartoons on all sorts of subjects, from financial to career advice to humor and just life insights. Jack is a smart, incisive human. We really like him. And Jack, thanks for spending the time to talk with us and our users today.
Happy to be here. Thanks for the invite, Adam.
And so, Jack, you've had some big life changes coming up. I think it would be fun to like get a level set and go through a little bit of what you're up to, because you know you're such a successful blogger. For people who know Jack, he has like 65,000 subs, he's just crushing it on the writing front, but I believe you just moved to San Francisco and joined a venture firm.
Yeah, so I'm actually—I'm still in New York right now. I'm moving to SF for like three months at the end of February and then coming back to New York for like a month or two basically to get all my stuff together and then moving out there for at least a year in the middle of the summer. But yeah, I was—it's the—there's a thing in venture capital where like a lot of venture capitalists decide they want to be like a Twitter influencer. I actually reversed the order on that where I was a Twitter influencer and then realized I actually would rather do venture capital than work for a media company. So yeah, I applied for a job in New York, I met with one of the partners in SF, he was like, 'You should move out here and work for me for a little bit,' and I was like, 'Yeah, that seems like a pretty good deal,' so I guess I'll just do that. So yeah, moving to San Francisco in three weeks.
What neighborhood are you moving to?
I have a sublet set up in the Marina District and I'll probably end up signing a lease either there or Pac Heights after.
Seems like the Marina is your vibe. You will have a really good time there. Go to a place called—it has to still be there—a place called Balboa Cafe. And yeah, there's an interesting scene there to say the least. It's almost like out of a reality TV show. You will see—you see some things there. Just go to the bar. You should go to the bar and order a drink and just watch.
If listeners who have been to San Francisco know what's going to happen next, we won't ruin it for Jack.
Cool, but it's a fun spot. Now I have something to look forward to, so that's going to be first stop when I get there.
So Jack, I'm going to back up even further because Jack is not a marketer by trade but does such excellent marketing online, and I really love guests who sort of figure out marketing from first principles because they approach it differently than a lot of us who were trained in it classically. And a lot of times they find these, you know, cool hacks or ways to do things that traditional marketers might not think through. And so I think that's awesome when we can—in any field where you get people who aren't classically trained in it have a different perspective and we can learn from them. So Jack, you grew your blog from nothing to over, you know, 64,000 subscribers. I'd love to hear some of the things that along the way you learned of building a successful media brand, especially because a lot of media brands are struggling right now. And you sort of did this without any external help, on your own, bootstrapped.
Yeah, so like for context, I graduated from business school this past May, so like May 2024. And before that slash during that, my kind of job was I was working for this finance meme page called Liquidity. So I used to work in corporate finance out of undergrad—it was boring, I hated it. I got into business school and then decided to quit my job and travel for a little bit before school. But I thought that this meme page guy was interesting. He built up like—probably had 700,000 followers across Instagram and Twitter and he had a newsletter with like 100,000 readers. So I just hit him up and asked if he needed help running the newsletter, and he for some reason replied and then said yes. And I convinced him to pay me like 500 bucks a week just to like edit his newsletter while I was hostel hopping in Spain. It was a sick deal. It was like a 24-year-old's dream. But what blew my mind was he was making like really, really good money from literally running a newsletter—just newsletter ads. So it was like that was my first time seeing how you could directly monetize attention and distribution. Like nothing like this computed in my head as something you could do for a living until I was working for somebody who was doing it. And I started thinking about like, how do I do that? And I'd been writing a blog on Substack called Young Money that had like, I don't know, like 300 subscribers. And I just figured, well, like everybody that is in this kind of finance bubble is pretty active on Twitter, so I probably just need to be tweeting a lot.
I mean, that's how we met. We literally were probably just in each other's replies on Twitter like three years ago.
But yeah, I was just tweeting a lot. Like anything that I thought that was relatively interesting in financial markets or just like as a young person going through life, I was just blasting my thoughts out there. If I agreed or disagreed with somebody on Twitter, especially if they had a big following, I would let them know what I thought in the replies. And you just do that over time and people start following you. But like three years ago, it was really easy to grow a newsletter on Twitter. Like in my head, I was looking at how Liquidity's newsletter functioned as a business and I was like, okay, if I could get to like 50,000 subscribers, I could probably just like sell ads on a weekly newsletter and make a couple hundred thousand a year just from that as a side thing. I didn't realize at the time that one, the ad market was very inflated in like 2021, and two, it was really easy to grow a newsletter on social media and it's just harder now. But anytime I had a tweet go—I got very good at making tweets go viral. Like I just got good at Twitter, like writing stuff that people like reading. And anytime a tweet hit like a thousand likes, I would just put a reply at the bottom like, 'If you want to read my best thoughts, they're on my newsletter,' blah blah blah. And it worked. Like anytime a tweet blew up, plug the newsletter, I would get like 300 subs. It was literally easy money. And then Elon Musk bought Twitter and it became hard to grow a newsletter on Twitter and that sucked. So I really missed the peak 2021 days of Twitter. It was a better website then. It was just more fun to be on Twitter like three years ago than it is now.
Well, the trend of suppressing hyperlinks is one that for sure predates Elon. Zuck has been throttling our links for a while. And you know, LinkedIn also—ironically it's called LinkedIn, but they absolutely hate our hyperlinks. And I actually have written on this a few times. I think it's missing the value of being the place you go that is the signal of the entire internet, which I think, you know, if Twitter frees its links, you know, it's a blue ocean for them to be that again. In addition to, you know, they're still the zeitgeist of what's happening in finance and politics and business and all these places. The people who left obviously don't think that, but you know, it definitely—if you look at how the country just voted, right, there's these disparate population groups who think, 'Oh, my bubble is right, my bubble is right.' But I would like to see all of these social platforms free their hyperlinks. I think it increases their value. If you send people to somewhere that is interesting from your source, it just elevates their value. So yeah. And then you also have kind of a cool stick in that you make these cool lo-fi cartoons with a lot of your posts.
And so I think that's one of the more creative things I've seen someone do. And I think especially in finance, like no one—I've never seen anyone do that before. Like I've seen this guy, Wait But Why, do it with philosophy, and I thought that was a small stroke of brilliance that you were doing these comics for finance.
Yeah, so I actually copied Tim Urban, who writes the Wait But Why blog. Like I always—there were two people when I was like in my early 20s who like basically bloggers that I really liked. It was Tim Urban and then Morgan Housel. And I liked how both of them wrote. I really liked how Morgan Housel was like very conversational and almost casual in how he wrote. Then he was writing about like kind of a mixture of financial markets and like personal philosophy, like behavioral finance basically. And then Tim Urban would write about anything from like how gravity works to like cryogenic freezing, but he would always have stick figures in his work and it made me remember it. And I was like, I've always been a little bit artistically inclined but never like an incredible painter or anything like that. I figured I could draw. I have this like really janky art program on my laptop called FireAlpaca and I just started drawing like stick figure thumbnails for all my pieces. Then people liked them so I kept doing it. But yeah, it was a stylistic theme because if you just post the article, it'll just have whatever your website thumbnail is. And then everybody else is either doing like AI-generated thumbnails or like pictures from the internet. Like that doesn't stand out. But like AI is some level of like really good, but it all looks like the same type of good. Like if you saw AI pictures now four years ago, you'd be like, 'That's incredible.' But now that everybody can generate it, it's not. And when it's not novel, it's commoditized. And if you draw objectively like low-quality but kind of funny like cartoon figures, people appreciate it.
Yeah, there's something to that. It's unmistakably human, and we are drawn to things that are imperfect and human, and that's something that AI can't really do like you can, right? Even if it's trained on you, it still lacks that je ne sais quoi of doing something with imperfections. I wrote a whole post on this and I actually talked about how, you know, the difference between like humans and chimp DNA is like 2%, and yeah, there's like a world of difference. Well, if the difference between us and the machines, even if it's better by a few percent, it's just going to be different, and that few percent actually matters a lot more than people think.
Yeah, yeah, I agree. Well, it's also like there's some level of people just like knowing stuff is human. It's like we don't watch robots beat each other in chess even though chess has been solved as a game. We've been able to beat any human in chess with a computer for decades now, but people like watching people play chess. I think that there's like—if people saw the same piece of art and then you told them that AI made one and that a human made another one, they're going to like the human one more just because it feels real. And the more tedious and abstract the task, the less the people care, but the more that it's in their face, the more they like knowing there's a human behind it. It's just like—it's weird otherwise. It doesn't feel impressive or real. Like you don't connect to stuff as well that wasn't made by another version of you.
Yeah, and also it's notable that people at the absolute top of their game choose not to use AI for things. So an example of that is in the movie Tenet, Christopher Nolan crashed a real 747 on site. And he uses some CGI in his movies, but he used a real plane for that. And I think the reason isn't just because he likes doing that—the reason is he knows the final product is just still better, right? And that's not to say he wouldn't use it in the future, but I think it's telling when people at the absolute top of their game—they know when to apply things. And I think that that's the difference between any armchair pundit talking about AI and someone who's actually in the arena. They'll decide. And you want them to decide, right? It's not like, 'Oh, AI is going to do everything,' or, you know, 'Oh, humans are going to do everything.' It's like the actual craftsman is going to decide what to use. Yeah. So let's talk about more human affairs—a subject you like to cover a lot, and that seems like it won't get out of the zeitgeist—is like young people and hustle culture. And so you probably have—you've written thoughts on this, but I'm curious your thoughts here. You know, in your 20s, is it the time to just grind it out, try and save all you can and build up this, you know, small amount of wealth to protect your individual sovereignty? Or is it a time to say, you know what, I'm just going to live on a shoestring budget, travel the world? Is there a balance between these things? And I'll ask that question with—I was kind of a weird person and did both. Like I lived like a wild 20s, but I also like grinded and saved money. So like I can't answer this question because I did both things. So how do you talk to young people about this?
So I also would say that I've done a little bit of both, and I actually think like my typical advice to young people is do a mixture of both. There's this—it's a thought that I've had more and more and more where there's two extremes, right? There's the like incredibly frugal, like high earner that goes into banking, law, whatever, where they're making by age like 26 $200,000 plus a year where they're crushing it, but like the last four years of their life from undergrad basically, like their life is controlled by their job or law school or whatever to go into that. Like you can do that, but there's a pretty big opportunity cost of that where there's like a lot of fun memories you could have made when you were younger. There's the flip side of that where you decide to go be a ski bum, operate ski lifts, like hostel hop around Europe. Like I met some people who had been doing the hostel thing in Europe. I did it for like on and off for about a year just traveling, and I knew that there was like a set endpoint when I was going to business school where like I would kind of take myself a little bit more seriously. But you meet people who are like 31 that have been doing that, had just kind of been floating around for years, and that's fun for a year or two, gets old. The way that I look at it is you shouldn't worry too much about your savings rate in your 20s, assuming that you're either like legitimately investing in your career and that you're going to school, or you're taking a low pay—like you could be if you're in Los Angeles and you want to be a talent agent, you're taking a low-paying job working at like UTA to like put yourself on a track. Like if you're like in an apprenticeship role, fine, like don't worry about money that much. Or if you're legitimately investing in fun experiences, whether that's travel or like joining a startup with friends where the pay's like trash, you're going to learn a lot from it. Like there's anything that just feels like it'll be valuable on a personal or professional level is way more important in your 20s than saving money. And the way that I put it is I think a very poor use of cash when you're 23 or 24 is putting away as much money as possible that you can spend when you're 70 or 80, right? Like the actual value you're going to get from that money is much higher now. But you want to set yourself up in a spot where you're pretty confident that you have high earnings potential as you get in your late 20s and then your 30s. Like when I was in business school, I was making like some money working for Liquidity and then doing a bunch of side stuff, but I didn't save any money at all for about two years. Like I was spending every dollar I made—made sure I had enough to like cover my bills, pay taxes, but there was like no leftover money after taxes at all for two years. It was fine. Like I make decent money now, I'm not spending as much now that I'm like a normal working human, and I had way more fun during that two-year period than I would otherwise. So like it, you know, it's important to set your career up where you're on the right trajectory, but like I wouldn't—I don't think people should be counting the dollars as much as a lot of people do when they're like 25 or 26. The trajectory is a lot more important than the actual number your first few years.
Yeah, and we have a lot of creative industry people listening to this podcast, and one thing that I'll say is like the crazy trips that I took and concerts I went to and, you know, adventures that I went on in my 20s—all of that is like an infinite well of inspiration in your 30s that you can draw back on those experiences. Especially if you're in a culture industry, if you're in media, if you're in marketing, like you kind of have to see how people really live. And when I say really live, I mean, you know, the ski resort is like this, you know, great place—like see humanity outside of a cubicle or a trading room floor. See, you know, go visit different cultures. Like those experiences are worth—like you can't get those later. And if you're in a creative field, if you're not just jockeying spreadsheets all day, that those stories are things that you can draw upon, pattern match, build upon forever to create your own, you know, scripts, your own fiction, your own, you know, ads and movies, anything else that you work on in a creative field. Like you kind of have to live a little. And when I say live a little, I mean like risk. I mean like do some things you shouldn't. You know, don't kill anyone, of course, or anything crazy like that. But maybe like, you know, when you're traveling somewhere, go across a, you know, that sign that says 'Do Not Enter' here and like go check out abandoned buildings or do something, get into trouble.
Well, dude, it's not even just people in the creative industry. I mean, I'm like—I'm technically in finance now, like I'm an investor as of three weeks ago, and there's a lot of benefit. Like pretty much any job that isn't a pure like tedious, just button-pushing job where you have to have like independent thinking and critical thinking, having exposure to a lot of different inputs at a young age is valuable. I mean, I remember reading about Jim Simons, who started Renaissance Technologies and made like however many billions of dollars before he died. He attempted a ride on like a moped from Boston to Buenos Aires, and him and his friend ended up getting arrested in Mexico, like southern Mexico on the way down. And the mayor of the town happened to have like gone to school in Boston and like thought it was funny they were from Boston. They ended up getting bailed out. But like he was a quant trader, like he was the most quantitative finance—everything. He still had those experiences too, right? Like there's a lot of venues for like creative outputs that aren't necessarily in creative industries. Where like your ability to have a different perspective on an investment opportunity could literally just come from having different inputs when you were younger. If you went to the same schools, had the same kind of training, jobs, and like investment banking, private equity, hedge fund as everybody else that did those same things, you're just not going to have that like differentiated of a perspective. So I think like those risk-on different experiences are almost more and more valuable the more like structured of a career path you end up going down because you can just like—you have new thoughts that other people probably won't have going into that.
