Redefining Finance Media with Jack Raines

Welcome to Innovation and Leadership. I'm Jess Larson. On this episode, back on my mini-series with my friend and co-host Ted Merz. If you don't know Ted, you should, uh, spent 32 years at Bloomberg. He was the bureau chief for news for out of New York for the Americas, and then spent the second half of his career rising to the top of all global news product for Bloomberg. Uh, these days he runs a great company called Principles that helps CEOs and executives with their online writing, whether that's LinkedIn or other things, and has big companies as comms clients, and lucky for me, he's willing to co-host this miniseries and talk about how business communications and the business media world is changing and evolving and has found us a pretty great guest for this week. Ted, why don't you do the intro?

Okay, I'm delighted to have Jack Raines. Hello, Jack. Jack was probably the first person who— you taught me more about the financial online ecosystem than anyone when we first met a year ago, and you continue to blaze a trail there. Why don't you tell us, just introduce yourself briefly. You're, I think, 26. You're at Columbia doing an MBA, but tell us a little bit about your content journey, where you started and where you are now.

Sure. So, Ted, one, thanks for reaching out and inviting me on the show. For a little context, I actually met Ted because we connected on LinkedIn. It sounds like this is a common ground, Ted meeting people on LinkedIn. We connected on LinkedIn last year when I was in my first year at Columbia Business School. I'm enrolled in the full-time MBA program there. And anyway, Ted reached out to me. We just chatted about like LinkedIn content, this and that. He was telling me about his career at Bloomberg. I was telling him about how I'd been basically just building up my blog and kind of internet following over the last few years. But basically over the last 4 years, I started writing a finance blog, Young Money, back in 2021. Um, the whole point of that was I just wanted a space to kind of blog for fun. And I'd applied for a couple of staff writer jobs in that, uh, last year before I started business school and nobody would hire me because I didn't have that much writing experience. So I figured if I can prove that I could put out decent content for 3 or 4 months in a row, then I could reapply to Morning Brew and some of these other firms I'd applied to. Um, And I just kind of kept writing the blog and it's grown from 0 to about 50,000 readers. Along the way, I reached out to an anonymous finance meme page on Twitter and Instagram called Litquidity, who had a pretty big successful finance newsletter called Exact Sum. I reached out to him about helping with that. He was actually looking to bring somebody on to help with like daily operations and some of the editing work. So I've been serving as editor-in-chief of Exact Sum for the last 2 years. And I actually recently accepted a job offer to join a new financial media company as an editor and contributor there. So I'll start full-time with them here in a few months.

I think it's interesting because when we first met, initially your goal had been to go to Wall Street. And then I think you started to do some work in the financial arena and you decided your passion was much more about writing about it. And that's when you started the newsletter. But tell, give us a little bit of sense of like the, 'cause you were early, but you tell us a little bit of how that started, how you started to get traction and a little bit of the dynamics of like creating a newsletter in the financial space.

Sure. So going back like to how I even got involved in the finance kind of social media sphere in the first place, there's a pretty niche community on Twitter That's like a lot of people talking about markets, stocks, macroeconomics, whatever. And it's almost like, um, it's like water cooler talk, but on the internet. And during the pandemic, I was trading stocks a lot. Specifically, I was trading SPACs a lot, and I found myself spending more and more time on Reddit, on Twitter. So I started seeing like just people talking about this stuff. And so I just started joining in the comment section. Chatting back and forth with people. This is probably, I guess, late 2020, early 2021. By summer of 2021, I'd basically stopped like trading stocks mainly because the SPAC bubble had popped. I'd made a decent amount of money on it, quickly realized that I wasn't going to make the same amount of money trading anything else because I'd gotten lucky as much as I've been skillful with it. But in the meantime, I'd started writing like contributor articles for Seeking Alpha and a couple of other sites just like in free time because I was working remote.. And then between those articles and then some of the connections I made on Twitter and Reddit, um, I figured that I might as well start writing my own blog. I tried to apply for a staff writer job at Morning Brew around July or August of 2021. Didn't have enough like real journalist or writing experience to get hired. So I realized this was like right when Substack was starting to gain some traction. I, I just launched my own Substack, figured that instead of just putting everything on Seeking Alpha or Medium or something like that, I should at least like own my own platform. So the goal at that point was really, I knew that I just, at this point I'd quit my job. I was working in corporate finance and I knew I was moving to New York and business school for a year. So I figured, well, like I had a decent amount of money saved up from like some of the stock trading the year before. And I wanted to travel a lot before school started, but I also figured it would probably be good to have like an income stream of some, some sort. And in my head, like, a staff writing job at Morning Brew would be the perfect kind of one-year thing to do before school started. When they didn't hire me, I figured that I would just start writing a blog and kind of use that as a portfolio of work to reapply. That didn't end up happening. I didn't end up reapplying, but that was the—

but that's an amazing thing because, um, I mean, I think one of the things people don't realize, and you know, when I got into journalism, you had to go work for a publication to get examples of your work. And so like you're basically just creating that on your own. I mean, that's what, when you start your own blog, you're like showing what you know and showing what you can do. I mean, that's, you know, that's a really incredible, I guess, point. I also thought it was interesting that you said you wanted to own your own platform or you wanted to, you know, own your, I guess, distribution by having your own Substack.

Right.

Why is that, why is that bad so much?

One of the biggest issues you see now is like content creators on any site from Twitter to Facebook to LinkedIn to YouTube run the risk of, I mean, the existential risk is getting deplatformed either for content policy violation or the appearance of a content policy violation. But beyond that, like Even a small tweak in like an algorithm on what type of content is getting pushed the most could screw up your ability to get in front of eyeballs. And if you're working for like a bigger publication, if all of your content is just with them, then you don't own any of that IP either. You don't own the email addresses. So like if you're at, I don't know, Wall Street Journal and you're a journalist or columnist there, then you want to do your own thing. Even if you have like a known reputable name, outside of your social media, like how are you going to tell people what you're doing? You have to start your audience over from scratch, basically market it from zero. So for me, once I kind of realized like how, especially with a newsletter blog, if you're having those email addresses, it doesn't matter what platform you're on. Like I started on Substack, I moved to Beehive. I just downloaded my email addresses and moved them to the other platform. And then at the end of every month, I just download like a CSV file. Of like my entire reader list, but it's become a good asset for me because like regardless of what I was doing for work or anything else, I would always have like that group of now 50,000 readers I can bring with me.

So like— That's amazing.

That's what I think a lot of—

No, when it thinks—

That's what—

Yeah. Yeah.

I guess a lot of people don't seem to realize the value of that. Um, you know, I was struck by that.

You don't think about it until you're— I was going to say you don't think about it until you're in a spot when you need it. You can build up a 20-year career and have a lot of work to show for it, but no monetizable asset that you can bring with you or it just puts you in a bad spot. You lose your communication channel and your reader list.

That's worth pausing because one of the things you probably noticed, Jack and Jess, but there were a lot of media layoffs this week. There were a bunch of people laid off from the Wall Street Journal, from other places. And sometimes there'll be a list of the people who were laid off on Twitter or something. So I went in and I looked them all up and it was interesting how some of them were people who had a lot of experience in journalism, but they had almost no connections on social media. And in some cases, no posts on social media. So to your point, I mean, it's, you, the community is there. You can't get it when you need it, you know, you have to build it along the way. So, and then, and that's basically, I mean, how did you do that with the content? Like what did you find what content was most effective or most, you know, helpful for you?

I mean, for me, I was just like the very, very early pieces. I thought that it was almost gonna be a like, not necessarily like a stock picking blog, but like writing about like more, like literally my thoughts on different individual stocks that lasted for a total of like 2 blog posts. Quickly realized one, you can't have like a strong actionable opinion on a different stock, like once or twice a week, you're either going to be putting fluff pieces out there that aren't like that detailed or like, or you're just going to be making stuff up. And like, I didn't even really like writing about individual stocks that much. I like Morgan Housel's stuff a lot. He was somebody who I've tried to like somewhat mimic their writing style a little bit, but more than the style itself, I like how like he wrote about almost like human behavior and human condition through a finance lens. And I think it's more fun to write about like how people handle their money or what they do with their money or how they think about money than writing about like which stock is trading at a lower than normal P/E multiple, or do we think that the revenue growth for Meta is going to slow this year? Depending on AI demand, stuff like that. And those more like, I don't know, philosophical pieces tended to hit it like just res— like, I don't know, people seem to really enjoy those pieces more. Like I can look at how many, like I can look at how many views or reads different pieces have and like my stuff about why I think people should travel more when they're young or like find out, like I have a piece called Infinite Games about finding stuff that you like doing for the sake of doing it. They have like 100,000+ views versus some other stuff I've written that's more market-focused is like 20 or 30,000. So, it was kind of the— I started writing the stuff that I like to read and that seemed to resonate with people.

And that's probably a good thing. I think that's actually how we connected initially was your piece about the importance of traveling while you're young, which if I paraphrase it, it sort of like says, don't wait till you're old and you can barely walk to travel. It's the—

that was not a piece of it.

But you also said, which really struck me, was the incremental value of traveling when you're young and learning all these things that can compound over time is unappreciated. People tend to wait, and whereas if you're traveling now at a younger age, you can really use that for the rest of your life. I think there were some other things there that were really, really interesting. But I saw that piece and I sent it to my son and it really resonated with me. And I think that's what— that was how we first connected. I sent you a message or something like that. Yeah. Yeah. I mean, how is your writing— how's that evolved over the past year? And I'm curious if you find yourself changing along with trends. Like, are there trends you see in online writing of what works? I mean, just sort of generally. Are you writing shorter, longer? What's happening as you— that's working for you?

I don't think the blog and newsletter stuff changes that much because once you kind of find your voice, if people like reading your stuff, they're more inclined to keep reading it. I do think that Twitter, X, I still call it Twitter.

I think most people still call it Twitter.

Yeah, you have to.

You have to.

Yeah. Twitter is like, that's the platform where you see different stuff perform better over time. Like 2 years ago, it used to be, um, people would put a clickbaity title, like 10 personal finance hacks that you have to know. And then they would just list 10 things. And at the bottom, they would say, if you enjoyed this, like sign up for my newsletter, this or that, that type of stuff worked a lot. Or just like in general, plugging your newsletter at the bottom of stuff worked a lot. I think Twitter's still very useful for like fostering connections. I don't think it's the best platform for newsletter growth. Like I think LinkedIn is a lot more useful for finding new readers at this point. And I've noticed like I can track reader analytics and click data and open rate data like on Beehive. And my average open rate for somebody who signs up from LinkedIn is like 59%. And then from Twitter, it's like 45%. So there's a noticeable uptick.

Do you think that's about the community or the type of people on the two platforms, or what's that driven by?

Maybe. I think that Twitter is a lot more dopamine-driven than LinkedIn is. So if you're writing long-form stuff, like you can scroll through Twitter and see a million different things in like 2 minutes. LinkedIn is a little bit slower and more like, it just feels more professional. So I think somebody who takes the time to read through a LinkedIn post, is like, we'll have a much higher conversion rate of like actually reading through like a 2,000-word blog versus on Twitter, somebody can read a little snippet that they like, click the sign up for my newsletter link, but not want to take 6 or 7 minutes to read a long piece when they're used to seeing like 280 characters.

It's interesting you mentioned that, but your pieces do tend to be long. I mean, you write pretty long for blog. What's it? Is it 2,000 words or what's typical?

Probably 1,500, but usually 1,500, but it'll creep up to the 2,000 range a lot.

I mean, I've had the feeling that that is somewhat of a signal of your seriousness, the depth. I feel like people are looking for that longer piece rather than something really short because that's, again, it signals more of a TikTok, Twitter kind point of view, a very, very short piece that's not very profound or deep, you know?

You know, one thing I would love to chime in about that is you think about the marketing value, right? Like, it's one thing to come at this from the media side, but the other side is like the, the corporate value of a fund of people in finance looking at the skillset, you know, hiring somebody like you for their team. Like you think about the straight out marketing value of like, if they can be putting 1,500-word messages in front of people that attract to say like, do you like the way our fund thinks? Do you like the way our firm thinks? Yep. As you think about people who maybe didn't come from this era, or if they did, but just have maybe not fully appreciated what a huge arbitrage it is to be able to get like this much of your personality and this much of your thinking in front of your ideal customers without having to pay exorbitant advertising fees. Um, what are some of your advice for first steps? Like, actually, just quickly before you answer that, how, how big is Liquidity and how big is ExecSum?

Yeah. So Liquidity, his total social media presence is probably, it's over a million followers. It's probably 1.3 million. And then ExecSum is about like 300,000. And he's been able to leverage his audience to like, he's, he's a venture scout. For Bain Capital's VC fund. He has gotten into some like venture investing on his own. He's working with like a, like health and wellness. I don't know if it's pronounced padel or paddle, but like the, one of the tennis offshoots that's better than pickleball. He's like working with a group that's like building several of those facilities around New York and Miami. But like he's been able to leverage his audience so well to turn into business opportunities. And that became like a blueprint for me. And frankly, That was like one of the big reasons why from seeing him and then a few other people like Packy McCormick landed a job as like an advisor with a16z and he turned his newsletter into a probably high six-figure business. Like I was seeing all these people do this stuff with the content. And then I was thinking about if I, because a lot of people go into banking and consulting recruiting, going into business school, if I was going to do one of those realistically, I would be more limited in the type of content I'd be able to write and the cadence I'd be able to put it out. So I went back and forth with it, but to me it made more sense to double down on the content stuff early and see what it could turn into before I graduated from business school. And then if it didn't hit like escape velocity in any way, look at pivoting into something else.

Well, I think about this, like, I know that we don't want to say live until you know you're allowed to, but like, you know, the firm that you're going to is one that 100% of people listening to this show would know is one of the biggest one of the biggest new names in finance in the last decade, right? And they obviously have seen the value in what you're doing to the point that they're hoping to bring you on and, and that you can attract these kind of eyes to them. My question for you is this. Let's say there's a fund manager listening today. I'm a fund manager. Like, I'm thinking about this for myself, right? Yeah. For those of us who either want to embark on writing and get serious about it, or who are looking to bring on the right people with this skillset. What are some of your thoughts about like rookie mistakes versus good first moves?

I think the biggest rookie mistake is not having your own distribution of some sort. Like whether you are a manager who's looking to put more content out or you're a writer who's looking at building their own portfolio. Obviously, like writing for a known reputable like media company is good and important and there's a, like, I, with my own journey, I look at the being in business school at Columbia as the prestige factor, but having your own blog or portfolio of work is something that like, you don't have to worry about being able to take that IP with you. Right? Like you can just immediately send examples of your stuff to anybody or everyone. And you can look through your email list if you have your own list and just look at some of the company email addresses and some of the names and see who's reading your stuff. Right? So not having your own distribution puts you so far behind. Like no matter what, whether you're literally a journalist or columnist or you are an investor, banker, lawyer, like CEO, whatever, who just wants to have somewhere to put their thoughts out, just put 'em on your own blog. If you want to publish on Medium too, you can do that. You can just copy and paste what you put on your own thing on Medium. You can tweet it, put LinkedIn posts, reformat the stuff however. But I think that everybody who wants to make content a more serious thing, should be doing something like that.

Yeah. Um, what's another first step? Okay. So own your distribution, you know, build your email list. Um, solid. What's, what's another one when you're thinking about specifically in finance, in investment funds, things like this?

What, as you're thinking about strategy, I mean, I think you need to, this sounds crazy, but just writing about the type of stuff that you want to write about is so important. Like with this job opportunity that I have, a big thing that stood out was my tone of voice and what I like writing about. Like it wasn't just another one of the like stock picking newsletters of this or that. Like I was writing a lot less quantitative stuff, but it was interesting and it resonates with people. But there's also a huge market for people who do get really quantitative talking about valuations, market trends, what we're seeing, who's raising funds. And if you're really interested in that, like people, people can, They can feel if you're interested in what you're writing about. And typically, if you're interested in that thing and you're good at it, you're going to attract the opportunities that you want, right? Like a lot of VC firms now are launching their own media arms where they're bringing on writers. Um, like First Round Ventures, I think they have 4 full-time writers and an editor. They put out like a weekly newsletter. So it's becoming a more and more valuable thing. So you want to be writing like in the finance space, you want your work to be compelling and interesting. And the only way to do that is like writing about the stuff that you're interested in. The worst thing you can do is write about stuff you're not interested in to get a job that you wouldn't want in the first place, because then you're just going to be miserable. Like, what's the, what's the point of that?

So I'm going to echo this advice for podcasting. So Ted and I's mutual friend, Mark, called me out one day. Mark Taylor, if you're listening to this, thank you. So we're talking, we're making a new show for him. And, um, he's like, hey, Jess, can I tell you something? I was like, yeah, what's up? He's like, I think your show is getting worse. I was like, oh yeah, Mark, why? He's like, I think you're bored. And I was like, he's right. I had been letting people on. I'd been letting guests onto the podcast too easy. And, and I, I would, I wasn't in, I wasn't enjoying it as much. And so I tightened it up and we got like 5 times as strict about who could make it onto the show. And so it was only like, it was only people that I really, really wanted to learn from who had genuinely done something special. That, you know, there wasn't just easy advice in the business books about, you know, and all of a sudden, like, I was enjoying my own show and then the guests can tell I'm enjoying it. So then they're enjoying it more. It's like if I'm having a good time and the guest is having a good time, then the reader, then the listener's having a good time. And like when we were starting this miniseries with Ted, he's like, well, should it be this or should it be that? And I was like, honestly, Ted, I think if we're having a good time because we're interviewing somebody you actually wanna learn from, that's kind of like the standard. Ted, anything you'd add to that?

No, I mean, I think that it's true. I had a client ask me recently what they should talk about or write about on LinkedIn, and they asked me like, what's hot? Like, what's working? And this, to your point, Jack, is I was like, no, you can't approach it that way at all. You have to approach about, you have to write about what you're really passionate about and you like and you're interested in. You can teach people. Because otherwise, it's going to come off as being phony. It's not going to work at all. So I think I'm echoing what you're saying. Find your own voice, write about what you know.

I get so frustrated seeing people when they obviously try to copy that blatant trend on Twitter or LinkedIn or whatever, because every single time there's a few people who pioneer a trend, And it's good. Like if you're the first person to really like start a trend, whether it's some sort of like formatting or type of thing you write about or whatever, and you're first, that's fine. But like people try to copy it because they see this one person do it and it succeeds and then they try it and then it usually doesn't work and they're miserable doing it. Like I've never had a content strategy per se on Twitter or LinkedIn other than like I'll plug my blog, like, subscribe link on a lot of stuff, which isn't really strategy. That's just kind of common sense to put it out there. Um, but like, when it goes to writing about stuff, half the stuff I post on LinkedIn has been just pure satire, making fun of people giving really, really lowbrow personal finance advice on LinkedIn. Like, that's— and it's— and people love it. Like, I've gotten up to 40,000 followers on LinkedIn just from being funny, from just like joking around, putting the type of stuff I would think is funny. Like, I was never try to be a thought leader on that. But on Twitter, I'm usually just riffing with people. And then if I stumble upon some just like insane thing, I'll write about it. Like one time I put this whole thing out about, it was when cryptocurrency markets had gone nuts in like 2021. And they had like gotten, I forgot what the timing of it was, but basically a lot of people have probably locked in capital gains by by selling crypto at high prices in September, October. Markets tanked right before end of year. And if they'd reinvested, they might owe capital gains taxes on stuff that's now down 70%. And effectively their whole portfolios could, they might have to pay them taxes. So I put this whole thread on Twitter just breaking out how like a lot of like former crypto millionaires are probably about to just pay everything capital gains taxes because it was a running joke that a lot of these, a lot of them were like 21-year-old kids probably hadn't accounted for capital gains. The thread blew up, it got like 20,000 likes, but it was just a random idea that I had that I thought was funny and wanted to write about it. So that's kind of been my like go-to north star for all of this is just whenever I have an idea that I'm interested in, I'll just chase down that rabbit hole and then like share my thoughts. 'Cause if I was interested enough to like think about this for a long time and then I can articulate it well for somebody else to understand, there's probably other people that'll feel the same way. So the guiding North Star really should be your personal interest. Obviously, if you want to use your blog as like a tool to help you move into finance, you should find that Venn diagram of what you're interested in that's also very relevant to like hedge fund managers or whatever. But it still needs to be something that you're interested in.

Yeah, 100%. Otherwise people, people know and it just sounds terrible. So I have a question for you, Jack. So one of the things, you know, I focus a lot on executives writing, and I think there's not that many you can cite. You know, most public company executives don't. There's a few people who are prominent. Sam Altman, of course, writes, and Rich Handler and Dan Loeb. There's a few people, but who do you, among that kind of group of people, who do you think's influential, interesting, creative, kind of, like, who do you read that's, among executives online writing who you find really trendsetting?

I think Josh Wolfe is one of the best. He was one of the founding partners of Lux Capital and he is on Twitter 24/7. And I met him in person for the first time a couple of years ago, but super interesting dude. I mean, he is like, it's like sci-fi nerd meets venture capital. And that's the type of companies they invest in. They're investing in all these defense tech, futuristic, this and that. And he is just constantly putting out tweets and data about like stuff that's trending in the markets they invest in. And it's cool. And he's like very opinionated. Like he'll get in arguments with people on Twitter sometimes, but he's got like 200,000 Twitter followers now. And it's because people like his voice. Matt Levine's obviously the low-hanging fruit. I feel like everybody reads money stuff. I think his stuff's great, but like out of people who aren't media people, but are like putting stuff out there all the time, Josh is, him. Gary Tan also, yeah, puts out a lot of content. Like, I think it's— I think venture capital specifically has more people posting than like any other facet of finance.

Yes, fair amount of tech venture. I know, I think in venture, you're right, Marc Andreessen writes, Paul Graham. Yeah, you know, they, they're pretty prominent. You know, it always struck me that there's more West Coast people than East Coast. I wondered if you noticed that and had any thoughts on that, or why is that? And is that going to change ever?

I think it's a tech thing. It's like East Coast is more Wall Street and West Coast is more venture capital. And it's just, yeah, like there's more, it's just more buttoned up, you know, like everything from compliance stuff to what can you put out there to just like, is it a little bit of an immature vibe constantly being on Twitter or whatever? I think that you're going to start seeing a bigger and bigger shift with how and this is a broader media thing in general. Like for example, um, Brian Chesky, Airbnb's founder, like whenever they do a, like any sort of PR, like press release, it's just his Twitter account, like new products, whatever. He's just tweeting it out because it gets much better distribution than going through like, like Business Wire or whatever. And I think people are going to start seeing that there is from a branding and marketing point, way more value in having your own Like I still think newsletters and blogs are the, are the best if you have email distribution, because it's the most stable and secure, but just having your own personal LinkedIn or Twitter or whatever media platforms you use, YouTube, like it doesn't really matter which one you're on, but having a big following where you can like control the conversation there is huge. And I think investing, that's going to matter more and more. Like it will go slow. Venture capital goes first because the companies are smaller, they move faster, this and that. But when you have a generation of people in their 20s now that are in their like 40s, 50s, and 60s decision makers who grew up being fairly active on social media sites, I don't think they're going to just stop once they get to those higher levels. So I think like, I think that's why the West Coast people are doing it more though, because it is more of the VC startup scene. Like it's, there aren't, there's not, it's not taboo, you know.

You know, I'm interested. Do you consume Gary Tan's YouTube stuff as well or just his Text.

So no, I actually didn't know that he was big on YouTube until he was on David Perel's How I Write podcast and he was talking about it. I had no idea, but I watch basically zero YouTube unless I'm looking for something specifically. Like I spend the majority of my content diet probably comes from Twitter.

Okay. How many hours a day are you on Twitter?

The screen time thing will probably say like 3 hours. I have no idea. Like it can't, it can't be healthy.

So, um, I'm interested, you know, cuz I look at, at my age group, kind of the youngest Gen Xers, oldest millennials, and like it is much more common to just be dropping YouTube references in the middle of business conversations with my friends, you know? And like I was, I wanna say I was like 16 in like '96 when our high school library got internet, right? And I'm begging my parents to get it and they wouldn't. And then like in '98, '97, I like moved away for grade 12. And so my family got it immediately so my mom could email me all the time. Right. And, uh, yeah, like, uh, there is this shift, right? There's this interesting thing. And so it's kind of fun for me. Like you look at this episode of like, here we go. Like Ted, who reached like the top of the top of the business media world, but who is interested in the innovations that you've done. And then he's reformatting the things he learns from people like you into the way that he's shaping like the generation that's in charge right now who come to him for advice of like, you know, these CEOs, these top executives are coming to Ted going like, oh, hey, the world changed. I don't know what to do about it, Ted. What do I do? And so it's interesting, this interplay across, across generations, across platforms, across, across social norms.

I feel like the internet has just flattened everything, right? Like when I was, like when Ted and I met, if we had met at any other point in history, like 20 years ago, we wouldn't have met, right? Like I would've been like an incoming MBA candidate at Columbia who didn't, who hadn't really done much in their career yet, this or that. Like I wouldn't have had a blog because blogs wouldn't have existed. But the internet gives everybody like a medium for putting their thoughts out there where you can literally be judged by the merit of like your thoughts and your opinion and your ability to write regardless of the pedigree attached to that. So you could see one of my blog posts, think, oh wow, this is really good without knowing anything about me and just find the writing versus there was no way to just find somebody's thoughts other than that. So you almost were forced to rely on the social signaling of where they went to school, where they worked, like what publication they worked for, but now that's starting to flatten. And if you have a following, that's an asset in itself, both from like direct monetization of, if you have a big enough following, you could monetize something with ads to like the ability to market yourself. Like my network from all of my content stuff is probably more valuable than my network from Columbia, but then the combination of the two, they like feed off each other. It's like, okay, I've got this big network I've built from Twitter and LinkedIn and my newsletter. I've also got the like social green checkmark of I went to a really good business school and they just kind of validate each other. But the internet has opened up a lot more opportunities for people who are willing to actually put their thoughts out there and go look for them because you don't have to spend 10 years trying to scale a ladder to get to the point that people listen to you. If your stuff's good and you're putting it out there and people see it, like people just like reading people's stuff. It's good.

I mean, one of the things I just say though, Jess, is when I met Jack, I mean, my kind of analysis of it was that Gen X grew up in a period where you had to be certified to do things. Like you had to have, whether it's Series 7 to trade securities, but like you went to journalism school or you did this, you got certified by some kind of experience to do a job. And I remember when I first met you, Jack, I was like, who allowed you to publish a newsletter about finance? Because I'm coming from a point of view, a lot of people older are like, you know, you need permission to do that. And you're like, no, there was nothing there. I just wrote it. I went for it. And I think that's, there's a bit of that generational gap, but unquestionably it's going to be more the case where it changes, you know?

Well, I think that we're going to see more and more media going that way where So for example, I think in pretty much any market, if you have people that have like worked in that field and then start writing about it, like Matt Levine's an easy example, but he was an attorney and then he worked for Goldman Sachs and now he writes a newsletter from Bloomberg. But like he was never, I don't think he was ever formally trained. Like I don't think he went to journalism school. He studied whatever in undergrad, then went to law school. And part of the reason he writes so well is he wasn't trained to write a certain way. So if you have people who grew up blogging or doing their own thing or journaling and putting their thoughts out, like when everybody goes to the same, like Columbia has one of the best journalism schools, if not the best in the US, but when everybody's getting the same curriculum on how to write, that's going to come out in what they write about. When you take people who've built an independent following on their own that didn't go through that traditional channel, they probably have a different perspective or tone or way of writing that's interesting. So you're going to see people who've like, I think there's going to be more examples over the next decade of people like me who didn't go, like, who didn't study journalism undergrad, who didn't go through, like, who didn't get a master's in journalism. And then they get job offers to work in media because their content's good and it's different from everybody else. It's like, you're not like, I'm not competing in the same pile of dozens or hundreds of applicants who went through the same, like, exact same process. It's completely differentiated.

What do you think about that, Jess? The way content's going to change in tone. I think he's right. I think Jack, you're 100% right.

So look, you and I, Ted, were, I don't know his last name, we were trading texts about Christopher Lockhead and the Category Pirate guys who wrote and, you know, that book Play Bigger, right? And to me, this idea of like, I don't know. Nobody buys a Mercedes because of how much it's like a BMW, right? Otherwise they would've bought the BMW. Like they buy it for the reasons it's different, you know? And this idea of like, can you, you know, can you follow the rules better than the last journalist is not, is not a way to strong profitability. It's like, can you create something different and valuable? And, and quite frankly, that has a bit of a moat around it because it's your voice. And quite hard for anybody to copy. And if they do try to copy, they're gonna sound like a second-class you. You know, think about how many, like, um, in the, let's talk like the social media or YouTube world, like, uh, look at these, look at these guys like a Gary Vaynerchuk or a, you know, Alex Hormozi is big these days, stuff like this. Um, and all the copycats cannot duplicate their success. It's like, you know, MrBeast. I mean, how many MrBeast copycat channels are there out there? Nobody posting numbers even close to his because they can't out MrBeast MrBeast. Right. And it's like he, like, you know, Warren Buffett and Charlie Munger always talking about like the, the financial advantages of owning an unregulated monopoly. You think about like yourself, like if you can create different and valuable content, whether it's written, like we're talking about video. Podcasting, whatever, if you can create different and valuable content, like the ability to have a monopoly on your voice can be highly, highly valuable. And I mean, I loved your example, Jack. I didn't know that Airbnb had switched their news releases to just putting them on Brian's Twitter, but like you think about, um, how much more humans like stories and they like the stories from a human, not from a logo, right? Like I, I wanna say like. Virgin has like 3 million social media followers, but, or 4 million social media followers, but Richard Branson has 12 million, you know, Apple, like the ultimate fanboys of all time have 7 million social media followers. Tim Cook has 14 million. Like the objective truth says people would rather listen from, listen to a human than a logo. And especially if there's some story, if there's some human relatability, like Jack, I loved your point about like. Understanding human nature through a finance lens, right? Like that's something that is pretty evergreen material because humans are predictably irrational and like the next generation, like Jack, your kids are going to make a whole bunch of same mistakes that Ted's dad made about underestimating risk and not checking the capital gains and doing like, there's certain things that, that, uh, if history doesn't repeat itself, at least rhymes, right? So.

Yeah.

Yeah. I think with, with what you're saying about like the Hormozi and the MrBeast, like when people are trying to like copy them, people aren't copying right either. Like you can't copy somebody's shtick, like whatever their voice, their thing is, but you can copy a lot of the process stuff. Like MrBeast being really meticulous about editing his thumbnails. Everybody should be doing that. You just shouldn't be making the same video MrBeast is making. Like a lot of the, from like having the LinkedIn premium subscription so I can have the button on my account, the like links back to my blog. That's like, there's a good conversion rate from that. That makes sense. Having like your own domain at youngmoney.co instead of youngmoney.beehive or.substack matters. It looks cleaner. But you can't copy somebody else's like style and content. So like people, Basically all the, to me, all the operational stuff that the best people are doing is what should get copied every single time with independent content creators. But like, if you're just trying to use somebody else's, like, to your point, you're not going to be the next Wormozy or MrBeast. You're not going to be better than them at being them. But you can speedrun the first early, like the earliest 3 or 4 years of what they were doing on YouTube or with their own businesses by getting the processes right quicker and then just working on developing your own voice.

Yes, steal the principles and the thinking, not the tactics.

How do you think of, Jack, how do you think of your voice? How do you in your own head describe what you do?

I think I don't even really know how to describe my voice. I think I write the same way that I talk. I don't know. I'm a 26-year-old guy who's pretty curious about stuff, who's a little bit sarcastic, but typically knows what he's talking about and admits when he doesn't. Like my, like if you read my stuff and then you talk to me in person, there's not really going to be a disconnect between the content and the human. I think a lot of people screw that up where their online persona isn't them. And it can be really tough to keep up a facade. Like a lot of the people who are big right now, I'll be shocked if they don't exist with social media in 5 years because you just can't keep doing a bit forever. And I think a lot of people think they can, or they get a huge following off of this one thing and they're stuck doing that thing. Like I've been pretty careful to like try to stay like true to what I actually think about stuff and my tone and this and that. He's like, I don't want to, I probably could have built a bigger following quicker if I'd really leaned into trying to be a character, but then what's the fun in that? Like you get famous for being somebody that you're not. I don't know. That's just, that's not a trade-off I'd be willing to make.

One of the things about your writing though that I think is important to mention if people haven't read it is, you know, there's some big influencers on LinkedIn where you could basically cut and paste their text and, you know, put it in your feed and no one would know. And I mean, I think in your writing, that's 100% not the case, obviously, right? You're writing individual stories about experience you've you've had opinions, you've had people you've met. So you know what I mean? That notion that people ask me what's good and I oftentimes just say, it can't be anything that can be cut and paste into someone else's feed when people wouldn't know. It's got to be uniquely you to that level.

Yeah. A really good heuristic is, could ChatGPT copy your entire content strategy if you fed it 15 of your pieces? I've actually tried that with mine. I've copy and pasted 15 random blogs and say, Okay, now write a blog about this topic in that voice and it's just terrible. But like, I'm not going to name anybody that I've done this like as an example of, but I have taken like a few people I've seen on Twitter or LinkedIn or their newsletters and copied their stuff. And it can honestly, like ChatGPT can publish stuff that's pretty in line with what they write. Right. So I think that's a good way of testing if your stuff's unique or not.

Where do you think you're going to go from here in your writing? Like what's, from where your head is right now versus a year ago, like where do you think, what's, where are you headed? You know, what, what, how's your writing changing?

I think one of the bigger changes is honestly the whole, like the business model behind it because at the end of the day, like you do still, especially living in New York City, have to make a certain amount of money to survive. Um, like a little over a year ago, my plan was, oh, like, just keep writing the blog, sell ads on it. And then it turns out the ad markets are volatile and it's also really annoying, like selling ads on a blog over and over again. So part of the reason that I took a second look at like some more traditional jobs, like salaried income, is that it frees me up to be a lot more creative with my blog without actually having to worry about the monetization and growth aspects of it. So like I can just like, I have my job that's, I make a living from, I'm still going to have ads and stuff on my blog, but like, I don't, it just frees up me from having to even think about that side of it. So I can write about whatever. So a couple of years ago, I really thought it would just be a big enough blog that like, that would just be the only thing I was doing forever. I think that there is a lot of value in having something that you still enjoy doing that like pays you so you can free up your passion project to be whatever you want. So like longer term, I'm thinking like keeping the blog going, writing books. I actually like the idea of being like a columnist and editor for a more established company while still having my own blog on the side. Like it was important for me to be able to do both where like I can put just more of my own like personal thoughts about whatever on the blog. And then when it's like more market-focused commentary, do it through like a more like actual publication. So I guess like the biggest change has been probably segmenting my blog to make it more and more personal stuff and then keeping the more like professional slash current events market news stuff with like a more established company.

That makes sense.

So, um, I know we're kind of winding down on time here. Um, I'm going to go back to kind of the theme I was on before of like advice for CEOs, fund managers who are wanting to take this serious. You know, we heard own your distribution, don't be yourself, don't try to be a character. Um, you know, have some sort of Venn diagram of what you're interested in talking about that, that the people you're trying to reach are probably interested in. Um, what's another principle you'd add to those ones?

Specifically for like fund managers, if you don't want to do the, like, if you want to do the content thing, but you don't have time to do it, it makes way more sense to hire somebody full-time that's going to be able to dedicate like a lot of time to it than like, there's a, like, there's a lot of, there's too many, frankly, I think there's a lot of agencies that are just spray and praying stuff. Ted, this doesn't apply to you, but there are a lot of agencies that are like, they overpromise and underdeliver on stuff just because it's so hard to really get in someone's voice. So like, you need to have— like, Chobani Yogurt hired a full-time ghostwriter paying them like $250,000 to run everything for their CEO, to do like speech writing. You almost need that level of commitment from somebody, especially if you're in a position of power and you have the money that you can afford to like pay somebody to come on full-time. Like, if it's going to be your voice, either needs to be you or needs to be somebody who's like compensated to the point that they can be you for all intents and purposes on your accounts. Because if it's like, if you're underpaying like an agency to put out like 2 posts a week or whatever, the content's probably, it's going to be flat. It's going to be stale because they can't get in your head unless they're like studying you. Like when Michael Lewis writes a book or like Walter Isaacson writes a book and it's a profile of a person, they're basically literally living with them for a year or two, getting all the notes they can. You need somebody who can have like a very high level of commitment if you want the content to be authentic and like pull from your life lessons and your voice and this and that. And then if you want to hire somebody to come write or hire somebody, like, so that's on the, like the executive side. If you're somebody who wants to like work for somebody like that, it's really just putting out as much content out there as possible about the stuff that you like because the Your ability to network or write the, or meet the right person through your writing is completely dependent on like your ability to put your writing out there as much as possible. Like the whole reason I'm on this podcast right now is because Ted saw something I wrote on LinkedIn. That's how this whole thing works. Like there's no, there's no sure secret code to getting like discovered, right? You just have to keep putting your stuff out there and talking about it.

Yeah, it's funny. I see that like I have friends who own agencies that will write books for CEOs who are like, man, they've got a great book in them. Yeah. But they spent the last 25, 30 years learning how to be an entrepreneur, not learning how to be a writer. And so like the CEO talks, his team records it, and then they make it sound like a book. Like my podcast agency, right? We're for like busy CEOs who don't have time to email and reschedule and reschedule and reschedule with these premium guests. They're like, I got 1 hour to do, to talk to somebody and I, I don't wanna be part of the editing or cutting social media. Like I don't, I can't do any of that stuff. I just wanna do like the, the, the only thing that only I can do, which is the interview. Everybody else can do everything else. You know, you look at, at TED or principles and it's like the CEO who spent 30 years or senior executive spent 30 years to have this certain insight. Right. But yeah, they, they wanna have the professionalism of a Bloomberg or Wall Street Journal level, you know, kind of it, it's their image. It's what people are gonna think of them. It's, it's positioning yourself in the marketplace. And, um, I, I actually don't hear this advice enough, so I was happy that you brought it up before I could, of this idea of like that senior executive, that CEO, like they've done the hard work to have the insight. And if you're, if you don't have the time, if you don't have the time to then put in the hard work for the format that's gonna work for consumption, hire it and you're gonna get what you pay for.

Yeah.

Right. 100%. Ted, what do you want to do for a final question here?

What do you want to do? No, I think Jack's right. I think it's going to be, I mean, I guess my take on that is I think that younger people are going to be more likely to write online. They get the dynamic of it. And so as they rise into this executive offices, you're going to see more and more of that. But I also think writing online is a kind of communication like speaking, which public speaking has become a much bigger deal for CEOs. It's become a much more crucial element than it was 20, 30 years ago. I think public speaking or public writing is going to follow a similar trajectory. So not today, tomorrow, but over time, people are going to be writing. And I think Jack Raines nailed all these points about it's got to be authentic, it's got to be what they care about. They can get some help, but it's got to really resonate that it's their ideas.

I know I used to take—

Go ahead, Jack.

I was about to say, I had a question for you real quick before we wrap up to go back to something you touched on at the very beginning. Where do you see the value add for good writing for, say you're a fund manager and you're looking to hire somebody for something, and the reason that you hire them is because they're a good writer? Like, why would you hire somebody who's a good writer? Like, what role would they be filling in, like, your puzzle?

Yeah. Um, well, I, I think this podcast is actually really good evidence, right? I consume basically nothing except audiobooks and YouTube and, and LinkedIn, uh, a bit. And even LinkedIn, I'm a skimmer. Like, I'm not a reader, right? Um, I'm like an audiobooks and YouTube guy and like the, some podcasts, right? I'm like such an audio-driven consumer. Like I listen to like 2 to 4 books a week. Right. And I mean, on an annual basis, like hundreds and hundreds of hours of somebody's keynote speech on YouTube sped up to 3.5x speed. Right. Um, and so, uh, like Twitter, Twitter's not going to get to me. Okay. Well, no matter what, how, no matter how good my YouTube channel was, it wasn't going to get to you because you're not, you're not a YouTube guy. You're intelligent. You're going places in your career. Uh, you're getting hired by some of the biggest names in all of finance media, right? You know, in, in finance. Uh, and you're not watching my YouTube, right? And so unless I'm willing to do what it takes to be a good writer, because just me writing, like, I'm probably not gonna get your attention. I probably like, you know, I wasn't necessarily gonna get Ted's attention as like, oh man, that Jess guy's a good writer. Like Ted and I connected on LinkedIn for other reasons, not because of Jess's eloquence. You know what I mean?

Right.

And so to me, like, I do look at the, the status upgrade of writing a book specifically, right? And you think about, Testing, like some of the best books that come out are people who tested the thoughts on their social for like a year or two on their way to writing the book. Yeah. And see what was resonate. And so like the idea of like, look, we brought up Gary Vaynerchuk, love him or hate him. The guy has written multiple bestselling books except that he's dyslexic and didn't write any of the books. Right. His job was to know what goes in the book and then bring on people who are really good so it can be written so well the rest of us actually want to read it, right? Richard Branson, major bestselling books, dyslexic, did not write them, right? And so I'm a yapper. I am a, I'm a yapper. Um, I, I actually enjoy writing. I just get the feedback from everybody like, oh, Jess, you really need help because this just sounds like how you talk, right? I'm not a sophisticated writer. If I want to influence, you know, ultra high net worth investors who want to, who are potentially considering being an LP in my fund, who are readers, my YouTube channel isn't going to cut it. My podcast isn't going to cut it. And so, um, overcoming my natural deficiencies or hiring them, one of those is a lot more efficient, right? And that's assuming that I could ever get good enough at writing to get that super intellectual person who is a, who is a text only reader. Right. So that, that's my initial thought.

No, it makes a ton of sense. I was, I'd never thought about like anything like that on the bridging the, basically it's almost like there's an entire different world from like the audio and video to the text. That makes sense though.

It's cool. Listen, my buddy did interviews. His name's Josh Steinle. He did interviews called Chief Marketing Officers at Work and it's a book. Okay. And he just talked to like cool CMOs from like Spotify and 20 of these companies, right? And having that published got him invited to Richard Branson's Island to go hang out with Richard Branson and a bunch of top CMOs.

Really?

Yeah. And all he did is a bunch of interviews and then transcribed them. And he actually is a good writer. Okay. So, so he turned into a good book, but like the supremacy of a book, books are hard and a good book is really hard. Yeah. There's so many conferences that the prerequisite to being considered as a Speaker is book. Do you have a published book? No published book, they don't even consider you, right? But what if you do, if you're me, who is not known for being an eloquent writer? Well, yeah, I can either struggle or hire, right?

Yeah, I think you're going to see a lot more just the value of communications. I really do. You know, people, people are more focused on the quality of the, of the, the level of communication, to which in part is of writing better, but just communicating better.

So, so I wanna, I wanna bring, I know this whole time all I've done is like everything you've said, I've related it back to me, but I'm still gonna do it again anyways. Okay. So what you said on the, on the idea of like, be yourself because it's harder to cape up being a character, right? I was so anxious starting my podcast cuz I'm interested in so many different things. I'm like, ah, everybody, everybody's gonna think I'm schizophrenic. There's gonna be nothing to tie this together, like what, like, you know, like I'm gonna lose the audience 'cause I put the wrong people on it. And, and like, um, it has ended up being my advantage. Like I guarantee if I had done the CEO show and I'd only put CEOs on, I probably would've grown faster, but I would've been bored. Right now that we do these like private event parties, um, I have like, you know, I had a really famous movie producer take me aside. Yeah. He, he produced a Will Smith movie that made $750 million. He produced, he was a producer on Dark Knight Batman movie. He was, you know, his Christian Bale movie he was on got nominated for 10 Oscars. Like this is a legit Hollywood guy, right? And at the end of this party, he takes me aside. He's like, hey, first, you know, a friend invited him to my, my, my party. I sat myself beside him because I wanted to meet him. And at the end, he's like, I want to tell you, you've really got something here. I go to, we were in Beverly Hills, this fancy house, this guy lent us. And, um, he's like, I go to a lot, I go to the fanciest parties in Hollywood. Um, but you know what? I see the same people there. I have never been to an event like this. You got, you got pro athletes and billionaires and AI guys and journalists. And like, this is such an interesting group. I've never been to a party like this. Like, you got to keep this up. This is so unique. Our very next party, I had a billionaire take me aside and he goes, hey, this, you know, it's like almost word for word except instead of I go to the fanciest Hollywood parties, it's like I go to the, they're just like my crazy schizophrenia of having like the women's, um, the women's kickboxing, national kickboxing champion on. And like, you know, I did an interview an hour ago before we hopped on here with you guys and it was like, This woman who for 20 years has been helping orphans and, uh, let's see, 23 years she's been helping orphans and 15 years in she realized they were like doing it all wrong and that 80% of orphans around the world actually have a living parent who's just too poor to take care of them. And it's actually 80% cheaper to fund the parent than to fund the orphanage. And they're like, they go out and like help these families start a small business so they can have. Their kid back. And, and like, you know, last week I had the CEO of $123 billion Booking.com on the show, right? It's like, and then we got 26-year-old, uh, you know, 26-year-old finance writer. Like, yeah, this— does this sound like the same show to anyone else, right? Those are all within a week of each other. But it, it's— and it, it like— and it has hurt my growth up front to do all these things But 900 and something episodes later, the people who like me really like me. And, and that's not this huge, huge number. Like I've had a few million downloads, but there's, there's people who get a few million downloads per episode. Right. But the people who like me really like me and like, good luck trying to, good luck trying to duplicate the variance of my guests over 900 episodes. You know what I mean?

Yeah.

So.

That sounds like a good, uh, good note to end it on, Jess.

No, I wanna talk about you, Ted. I love your Bloomberg stories like this, the, your one about Bloomberg AI that came out on LinkedIn the other day. But then you've like, you've got all this stuff with your dad and people really resonate with this like family connection that you're not just a business guy, that you're like a real human in there, you know? And, uh, that's not like, that's not easily duplicated.

I think that's right. But I think it goes back to what Jack was saying. I mean, in my sense, I just write about whatever I'm thinking about that I find interesting. And if I feel like it's going to be better if I'm interested in it, and that's it. You know, you just have to let that go. Yeah. And you see where it takes you.

Okay, Jack, where can people go to sign up for your newsletter, read your blog, What's your Twitter handle? Where are all the places?

Yeah. So if you go to youngmoney.co, the .com was already taken by Lil Wayne's record label, so I'm using the .co domain. So youngmoney.co, that's my blog. Youngmoney.co/subscribe pulls up the subscribe landing page. You can just go to youngmoney.co and sign up there. You can find me on Twitter or the site formerly known as Twitter at Jack_Raines. And on LinkedIn at Jack-Raines. So yeah, just Jack Raines, everything.

Well, this is great. I feel like I learned a lot from you today. Um, Ted, do you want to say anything?

No, I hope to see you soon, Jack. I saw you, what did we say, a month ago or so? Somewhere we're at an event.

Yeah, we'll be speaking again soon.

But I'll see you soon.

Jack, what do you want to leave everybody with today?

I don't know. I just think you need to explore your interests. Like for everybody out there that's writing or wants to write or whatever, like start a blog. I've had 3 friends from business school in the last week saying they want to start writing stuff more. What should they do? I'm like, start a blog. And they're like, that sounds hard. And I'm saying, no, it's not. You just, it takes 5 minutes to sign up for it and start writing stuff. Even if you don't know what you're going to do with it, if you want to put your thoughts somewhere to share with other people, start a blog, write about what you're interested in because you don't really know where it's going to take you, but it could go somewhere cool.

Absolutely. Okay, folks, thanks for doing this.