#024: Jack Raines - How to Build a 100K+ Audience Leveraging Content

I still think it's really valuable because it just puts you all in the same place at the same time, right? Like, how many people can you actually meet in one-on-one sending out cold emails or outreach or this or that versus just being in a pod with 800 of them at once? You're speedrunning the entire networking process, and if you're good at networking, then that honestly gives you outsized benefits. You're going to make friends faster, make connections faster, and if you do want to do anything even remotely traditional work-wise, all those companies are there and they're like actively trying to target people at those schools. That's a very good fallback that opens a lot of doors. It validates you in a lot of people's eyes, and you can springboard from that into a lot of different niche stuff, but you're starting at a lot higher springboard point, if that makes sense.

Jack Raines is one of the fastest growing content creators on LinkedIn and X with a combined audience of over 100,000 across channels. Based in New York City, Jack recently finished his MBA at Columbia Business School and is a full-time editor and creator at Sherwood Media. In this episode, We dive deep on Jack's tactical lessons in audience growth, the outsized ROI on consistency and authenticity to break through the noise, and why he thinks business school is a contrarian bet in 2024. Welcome back to episode 24 of the Turning Pro Podcast. Today we have Jack Raines, who is the writer of the finance blog Young Money and a world-renowned LinkedIn shitposter.

Happy to be here. Thanks for having me, guys.

It's the best intro I think we've done since we started this pod.

All right. I want to start with B-School because when we think about contrarian moves in today's climate, you probably have the biggest one, which is going to B-School when everyone on Twitter that you hang out with—

That's business school for those listening.

Right. That's a good abbreviation.

I'm sure everyone on Twitter that you hang out with is like, what the hell are you doing? Because it's not very popular. So tell me more about the decision.

Well, it's funny that you say that because the Twitter world and the real world are like two almost completely different things, right? So everybody on Twitter and social media is very anti-traditional path, do your own thing, this and that. And then in the real world, everybody would be like, if you get into a good business school, why wouldn't you go? Um, the truth is I just got into Columbia out of undergrad. So Columbia offered like a deferred enrollment option where I applied when I was 22, got in, had to work 2 to 4 years before starting school. Uh, for context, for business school, most people work like 3 or 4 years before starting. So there wasn't really like a grand master plan going into it. It was just, I went to a pretty average school in the Southeast. I got into a really good business school in the Northeast. If you look at the earnings projections for people who go to Columbia Business School versus people whose terminal degree is a bachelor's degree from Mercer University, it's kind of night and day. So it was really, it would've been crazy not to go. Had I been like 26 or 27 considering applying, I don't know if I would have or not, but it made a lot of sense like coming outta undergrad. And frankly, looking back now, it's still been the best decision.

For people that hang out on Twitter or LinkedIn specifically, like circles within money Twitter that may not be big fans of B-School, can you walk people through what you've actually learned, why it actually matters, and like how it's benefited you?

I mean, the biggest— people, everybody's like, oh, you probably don't learn that, that much in business school. And yeah, like it's not like the, the curriculum rigor wouldn't be the same as med school or law school. Like there's other graduate degrees that are tougher. The biggest benefit is People say network, like it's become a big cliché, but it is true that like we have 800 people in my class. There aren't that many like mediums or venues for getting 800 people that are driven, intelligent, and have a very high likelihood of being overachievers in their chosen field than business school. Like some people are gonna go down more traditional paths like banking or consulting. Some people are founding startups. Some people are going to VC. Private equity. Some people are going into tech and media. So instead of like having a bunch of random one-off, two-off meeting people at parties and stuff, you just have like 800 people where a very big proportion of them are going to do cool stuff, right? So that's, that's kind of the biggest value add, right? Like the network that you get from that. And there is a lot of exposure to like very good faculty members, especially at Columbia. Like a lot of my professors, especially the ones who teach night classes, might have a day job where they're a partner at a bank or, um, like I had a marketing class last year where he was like one of the head marketers at Procter Gamble for years and now runs his own marketing consulting firm and was talking to us about all these projects he did in Europe and Africa. So you just get a lot of face time with a lot of people who otherwise, like it's people that people would pay a lot of money to get in front of and you get to be a student in their class. Um, and there is a big pedigree aspect to it, right? Like, at the end of the day, and this is something I've realized more since being at Columbia, people say, oh, like, is it actually that much? Like, like how valuable is, uh, like MBA at this point? Like, can't you learn all the material online?

Like, yeah, sure.

You probably could. You could say that for any degree. You could probably learn the actual knowledge part of literally any degree anywhere from the internet, but the social signaling of being in a good school still matters. And that's something that I think that the social media side misses. And it's something that I didn't really pick up on as much until I got here. Like Twitter's a pretty small bubble and the amount of people who actually have a following or use it regularly is, I don't know, let's say maybe, maybe 10 to 100,000 people total. And there's what, like 350 million people in the US alone? Like a lot more people are gonna know if you went to like Harvard Business School than if you have like a decently big but niche Twitter following, right? So for like just broader pedigree and appeal, it matters. Like there's— you can't really put a price tag on it because you can't— you can't fake that level of recognition when you're just meeting people.

So I want to— I want to dig in here.

Hit me.

I'm anti-business school.

Okay.

So I think it makes for a very good conversation. I just have a couple of questions for you. The first one is, if network is not your problem as an individual, like you, you have a way to like build relationships with people. And the second thing, so that's the first one I guess to unpack is do you think if you're someone who really understands the value of network that business school might become less valuable for you as an individual if that isn't your issue? And there's, there's multi steps to this question, but that's like part one.

Yeah. So I think like if you're like naturally a go-getter and good at networking, I still think it's really valuable because like it just puts you all in the same place at the same time, right? Like I would say that I'm in the top decile of networkers. Like I'm a social dude. I'm good at meeting people both in person and on Twitter. Like we met because I just, I think I just messaged you on Twitter randomly, right?

Yeah, man. Months ago.

So yeah. So that's like, I'm good at that, but it's still like, how many people can you actually meet in one-on-one sending out cold emails or outreach or this or that versus just being in a pod with 800 of them at once? Like, You're speedrunning the entire networking process. And if you're good at networking, then that honestly gives you like outsized benefits, right? You're gonna make friends faster, make connections faster. And if you do wanna do anything even like remotely traditional work-wise, all those companies are there and they're like actively trying to target like people at those schools. And I'd like, I would have a, I'm at the far end of the non-traditional, like path of people in business school. And I used to look at it like a black and white, like, oh, you have to go in one of these two or three super defined tracks or you have to do your own thing. But there's a lot of gray area. Um, like I was talking to our friend Liam about this today a little bit. Like he used to work at Goldman Sachs for a little while and now he's worked for a startup. He's worked for a media company. Like he's done a lot of different stuff, but he was saying how there's a lot of value in like, if you get in with one of those bigger traditional organizations and do good work, Like that opens, like that's a very good fallback that opens a lot of doors. It validates you in a lot of people's eyes and you can springboard from that into a lot of different niche stuff, but you're starting at a lot higher springboard point, if that makes sense. Like I think that Jack Raines, the finance blogger who's at Columbia Business School, who's met all these people, is more valuable at surface level than if I was the exact same skill level of a writer and had the exact same social skills, but I was just like, doing my own thing in Austin, Texas, or Buenos Aires, or Sydney, Australia, or whatever. So I think it's still like it— I think the social skills are almost like, uh, like a, like a coefficient that multiplies wherever you're at. And if you have the good social skills and you're at a good business school, like, you're gonna see outsized results from that.

So the second— I actually very much agree with what you just said. The second point that I'm going to bring up that I think matters more from my perspective is the one around the career path that you would like to take relative to going to business school. So when you speak to like the more traditional roles like banking, consulting, private equity, I fully understand it. Like I've— from what I've been told from my friends in that path, there's a lot of instances where you kind of cap out unless you go to business school and then you're able to like get into a higher role. I think I more have an issue with business school for people who are entrepreneurs who say they want to be founders. So they, they go to business school because they want to be entrepreneurs. My perspective on it always been like, do you trust the guy who reads about building businesses for 3 years or the guy who just put his hands in into it and started building them? And maybe there's nuances to this answer, but fundamentally I think I'm more anti-business school for people who like go to it knowing they want to be entrepreneurs instead of just like facing the reality that building a business is hard. Going to business school just prolongs the, the reality of like the rubber meets the road when you're starting from zero, whether it's today or 3 years from now.

So I've got two thoughts on that. First, like, do you know the average age of a successful startup founder? By successful, one that either gets acquired or gets to like a unicorn valuation.

My guess would probably be like 37.

Yeah, it's, it's, it is like late 30s to mid 40s, right? So like you increase the chance of, if you wanted to like be a founder and make a startup, you increase your chance of success if you have more work experience going into it. Like we kind of romanticize the Mark Zuckerbergs because they're cool. Like Everybody would love to found a multi-billion dollar company in the early 20s. That's not like reality for most people. So it's not that business school makes you a better founder, but it could get you in a lot more valuable jobs and roles where you get more experience that would make you a better founder. So no, I think that if you are dead set at like 27 and you have the startup idea you really want to do and you also want to go to business school, it probably makes sense to work on the startup. And then if, you see that it's not gonna work after a year or two, you can always go back. I don't think the two have to be mutually exclusive though. And there's also like, if you know you wanna make a company at some point, but you know that you aren't ready for it yet, using business school to accelerate your career with that still being the longer term goal makes sense. Also, I don't necessarily think that they're mutually exclusive. Like, yes, you're right. That like, if your plan is I'm gonna go to business school to learn more about how to do a startup to do it, that's not gonna help you. Like, you're not gonna get some, Holy grail of like company creating knowledge from taking a seminar on building a business. But if you do have, like, if you do want to found your startup, but you don't know exactly how you're gonna go about doing it yet, frankly, it does give you a 2-year professionally acceptable window to experiment and try different stuff where you could spend the first year like working on the startup while still having a safety net of if you see that like fundraising wasn't as easy as you thought, or like you're not getting the ARR that you thought you could. It's still much easier to pivot out of that into another job. So I think it on one side reduces the risk of if your startup fails, having good exit ops. And then also if you aren't ready to found a startup yet, it still benefits you from all the career stuff I said earlier where like a lot of people that are going down the like banking, PE, consulting route aren't gonna stay there for 20 years. They might stay there for 3. But if you like, say you go into banking and you're making $250,000, $300,000 outta school, then $400,000, then like $600,000. If you can build up over $1 million saved up before founding your startup, you have a lot more like margin for error, right? Like you have a lot bigger nest egg to fall back on where you don't need to be making money as soon.

That was— so this is my last question on the topic and then we can shift gears.

Yeah.

The concept of money. So what is your perspective on how expensive business school is now? Not everyone is a trust fund kid or was able to earn enough money on their own to be able to do it. So there's a lot of people who are probably putting themselves in debt coming out of it. What is your perspective in that regard? If it's like a cost-benefit analysis of like spending, I don't even know what it costs, say, but $300,000 to get an MBA versus taking that money elsewhere, just not spending that money and go getting a job.

No, that's, that's, so that's, I think the biggest pushback against that actually makes sense. And that is a, depends on the person. Um, there's a lot that goes into it though, right? Like if you're going, like if you say bank, like banking would probably be the highest earning job that a decent number of people out of a business school class are going to get. Like we have, in my class, 80 or 90 people going into banking where you're gonna make, unless like a really bad recession hits where it doesn't matter what you're doing, like everybody could get cut from anywhere. Any given year, you're gonna have a lot of people making a lot of money coming out of that. Where if you go say $200,000 into debt, but you know you're gonna be making like 270, 300, 400, 500, you can pay that off in about 5 years. Um, I don't think it makes sense. Say you're dead set on doing a startup and you don't know like what the cash flow's gonna look like, what the revenue's gonna look like. Going $200,000 into debt to launch a startup where you don't know like how much money you're gonna be able to pay yourself, you can be putting yourself in a bad spot where if you're having to pay, like now people have to pay student loans back now, they're not paused anymore. So if you have to pay a lot of money like in student loans and the interest is piling up and you can't make that much money from the startup, no, it doesn't make sense. So it's, it's one of those things you need to take into account, especially if you're someone who is gonna have to take out student loans. Again, some people, Like some people that are consultants have their company sponsor their MBA and then it's paid off. They go back to work 2 to 3 years. Some people either have like a big scholarship or they're getting like a merit-based scholarship, need-based scholarship. Some people just have a lot of family money. Like most people haven't saved up enough money by 27 to pay for business school. And then some people do have to take out loans. So it is a, it depends on your financial situation. Like if you're going to have to take out loans, it makes more sense to go into a career path. Where you'll be able to pay those off before trying your own thing, but you're still getting the network benefits and getting good career experience along the way.

I think the, I think the social signaling and the social proof benefit of having that on your resume or even in conversation like, hey, yeah, I went to Columbia B-School. Yeah, but I will say the thing that surprises me is friends that I went to school with or friends that went to like Yale or Harvard and then they went to McKinsey and then they went to IB and now they're at Wharton or Penn or somewhere else. That's what confuses me because I think from the conversations I've had even to this day, like when I'm talking to a lead or a customer that may work with us at Verbatim, to this day I still get the question like, where'd you go to college? Yeah, in almost every call, even though we're like a few years old now.

Really?

And yet to this day, and that hasn't stopped, that's always part of the conversation, especially with investors or folks in private equity or VC that always comes up. And so I think from a social proof lens, if you don't have that validation yet, you haven't worked in big tech, you haven't worked at McKinsey or Bain, you haven't gone to a good school, then I think B-school at a great school. Yeah, 100% worth it. Because for the next 40 years of your career, I'd guess at least half conversations they'll ask, where'd you go to school? Where'd you go to undergrad? Where'd you go to B-school?

Yeah, no, 100%. And so you were saying like the people who've hit all the like A+ spots, you're asking like, why are they going to school if they already have the social?

That's what confuses me.

I think it's two things. One, it's kind of what you're supposed to do if you've done all those things and you're trying to pivot into something else entirely. Business school becomes the kind of go-to pivot. And two, a lot of those are like pretty high-stress jobs where you're working long hours, and business school is like, it's fun. Like, that's like, I'm talking about all the career and professional and academic merit to it, but it is like a very fun way to spend two years. If you're 28 and you've been doing the banking to private equity grind or something like that, and you want to do something different, you have some money saved up and you need, you want to like take your foot off the gas a little bit and have some time to recalibrate. It's way, it both looks better and feels better to take 2 years of business school rather than just quit and like sabbatical for a year. Like most people don't want to do a year of just like pure sabbatical, not working this and that. Business school keeps you like. Intellectually stimulated. You're still doing stuff, but it takes your foot off the gas from like the corporate grind for a couple of years.

Yeah. I want to talk about your content for a minute, and I want to start with the fact that within the spectrum of people, especially founders and operators in the tech world that have been able to find their voice very quickly, on the other end of the spectrum is probably you and a couple of the writers, maybe like our mutual friend Tommy. Yeah, a handful of folks that the minute they start producing content— this may not be true, it seems like you've already found your voice and it's like you're talking naturally to people. Was that— is that just a skill set of yours that comes naturally? Because most founders I work with have tried for years and they can't seem to find their, their voice in social or in content.

I think, I think for me it's because I never tried to be a like thought leader or try to be a certain type of like, it's almost a joke on Twitter, all these guy accounts. Like there's, I don't know, like there's Real Estate Guy or Car Dealership Guy or Um, like Secret CFO, like, and a lot of these people are people that I'm Twitter friends with, but they have these like anonymous accounts that are branded around a certain type of thing. If you're trying to be a type of voice, it can get really, really, really tedious trying to just produce a specific type of content. Like I call my blog a finance blog cuz it's the easiest, simplest way to describe it, but it's not like I'm writing about like personal finance tips and like stock market stuff. It's just, Whenever I have something that's interesting that I would probably talk about with a friend, a lot of times I'll just go down that rabbit hole, either just writing out my thoughts, or if it's more like research-intensive piece, just like looking something up, going down like a Wikipedia rabbit hole and writing about it. But I never really thought about trying to find my voice. Like I do the only like active trying to figure out how I'm gonna write that I ever did was thinking pretty consciously that like, I wanna write stuff that I'd like to read. So I was never trying to like sound overly engaging or this or that, but the blogs and newsletters I liked reading or the Twitter content I liked, I tried to kind of mimic, not copy any particular person's voice, but stuff that I found engaging. I tried to incorporate into my stuff.

How much of that do you chalk up to just being unapologetically yourself? Because I think when you come, when it comes to this topic of finding your voice, I think the reason you didn't have to go find your voice is because you are yourself and it is your voice. Whereas I think there's oftentimes people online who try to be someone that they're not. To craft this persona of what they envision they should be versus what they actually are, which is why they never find the solution. So I'm curious for you, when you started being a content creator, were you kind of just like, I don't really give a shit what people think, I'm just gonna speak how I speak and be who I am, and you either like it or you don't, versus overthinking every single time you want to put something on the internet?

Oh yeah, no, that's, that's exactly it. I mean, the whole way I started writing or like doing anything in the first place was so like I was planning on starting business school in August 2022, which is when I ended up enrolling. And a year before that, I quit my job and I was just gonna travel for a little bit before school. Um, but I applied to like several remote writing jobs for like staff writer roles with Morning Brew and some other media companies. And I didn't, I mean, I'd written a few freelance finance articles on seekingalpha.com and like I didn't really have any actual like journalistic experience. So nobody would hire me and I just started blogging because I figured I just need to show that I can put out like interesting stuff on a regular basis, but that was it. So I was just like writing about kind of my observations on stuff. And to your point, it was that I didn't really give a shit about what people thought of me, but I didn't have a job. I was just traveling around. I knew I was going to a good business school. So it wasn't like there was any real career risks to what I was doing. Like if you're working for a large corporation that has a fairly restrictive, like social media policy, you have to be more careful about what you put out. I didn't really have any, like, like anybody watching over my shoulder on what I was doing. So it kind of gave me full rein to write whatever I wanted. Um, so yeah, I mean, I think that is a big part of it. People either try to be something they're not or they're scared to be themselves because of like career or social blowback.

What advice do you have for a founder out there? Maybe they just raised their seed round and they know they need to be more active on social and they decide, hey, we're not gonna go the ghostwriter route.

Yeah.

I really want to try to find my own voice. Voice, and I know it's going to be kind of awkward, what advice do you have for them very tactically? A, around even things like posting consistency, formats, what channels to focus on, and then B, just come to terms with trying to find your voice. Because for a lot of folks that haven't written content, it's a really awkward process.

I, one, I, and I'm gonna get some pushback from this on the Twitter people, I'm not a big fan of the whole ghostwriting thing because if you ever switch ghostwriters, you have someone else who's gonna have to find your voice. Like you're putting a lot of your brand value in the hands of somebody else. So it's better, like if you're a founder and you can run your own account, do it. Or you'll see some of the bigger companies, like there was, I think it was like Chobani Yogurt had hired, they paid a ghostwriter like a quarter million dollars to like do everything for one of their executives from speechwriting to ghostwriting. If you have like a full-time person who can do stuff like that, that's fine. Like that works too. Um, but you have to be really careful about outsourcing to ghostwriters. And if you're gonna do that, you have to be very meticulous about how you want everything crafted. Like there's more and more and more people who are doing like ghostwriting where they bring out a lot of clients. And a couple years ago, a lot of the very like cookie cutter templatey stuff worked, but people just, they can see shit. They can see shallow content now. Um, My 2 cents are like, if you're a founder, just posting regularly, like about what your company's doing, like Brian Chesky, Airbnb's founder, is masterclass of this. Like all of Airbnb's product announcements he does from his personal Twitter. Cause if they were doing them on the Airbnb account, maybe gets 100 likes when he puts stuff out there and then he is like engaging with people. Um, like I saw somebody share, I forgot it was like a product release they had like, or feature release they had a couple of months ago. His tweet got like 2.7 million impressions. Because he's actively engaging with people and it's coming from a face. Um, like people like people a lot more than they like brands. So if you're a founder and you can just like talk about what's going on and you're interested in it, that's literally the best thing to do. It takes like, you don't have to use a PR agency cuz nobody's reading like press releases anymore. You're not putting your content strategy in the hand of a ghostwriter who, if you have any kind of falling out with them on a contract, they're not gonna be there anymore. Like, you kind of control your own brand destiny.

Here's my question. Look, I have a ghostwriter and I, I'm not afraid to admit it, but I think my angle on it is different than others. And this is why I'm curious. When you think of a ghostwriter supporting someone building social, do you see it as like a binary thing where it's like either the ghostwriter's doing it or you're doing it?

No.

Because for me, just to give you context, like from my lens, I post on Twitter all the time. The ghostwriter value in my mind is like more technical, uh, posts that require a lot more time to put into them. That it's like an accountability threshold for me to ensure that like the most important parts are constantly getting out there. Like today, for example, today's been a shit show with like what I'm dealing with. If you told me go sit down for 30 minutes and write like a thread about a feature that you're— I would tell you, I would give you the middle finger and be like, I have way more high-impact things that are happening in my business today that I have to deal with. But that doesn't mean that I want to, like, do that at the expense of maintaining consistency. And so for me, like, I, I read everything that goes out and I would say maybe 20% of my content is from a ghostwriter. Yeah, but it's more to maintain that surface-level consistency on days where I just don't have the mindshare to be able to do it. Not because I want to delegate my personal brand to someone else. Does that make sense?

Yeah, no, that totally makes sense. I guess I was more—

and you're like, you're— by the way, you're allowed to be like, no, I disagree with you.

You're an asshole. No. No, I, I think that makes sense as long as you're still the one in control of it and it's more of a, you kind of hit your like breaking point on, okay, like I only have so much bandwidth to do this and if I can do a big part of it and then outsource some of it to make the overall content more consistent and fluid, sure. It's when companies or brands or like startup founders literally don't want anything to do with it and they're just like, this agency's gonna handle my whole growth for me. No, because at some point, like, there is always that risk of like they want to charge a rate that you can't afford or the content just isn't as good. In your case, like, you're so plugged into the process of what's going on because most of it's coming from you that like even if you fired the ghostwriter or all of a sudden there was a mismatch on pay or anything like that, like, you could take it back over and keep your Twitter presence going fine. People who try to outsource the entire thing are the ones who have the biggest risk. So as long as you're on top of the strategy and it's just a, I don't have time to do all this, but like, here's what I want done. It works. It should be a resource and not a replacement.

That's a really good point of being a resource, not a replacement. I think the second piece to it is what he's told me is I'm one of his favorite clients because I have too much content, right? Because I have a podcast. I like doing content things. I have a ton of ideas and it's just become a bandwidth thing. So I'm like, I need you to help me supplement, making sure I'm getting these out there. Versus people who want to build a personal brand, who have no unique thoughts and no original content, who are expecting a ghostwriter to be their brains and their execution versus just the execution.

Yeah.

Which I think is the big distinction for me at least.

Yeah, I know that. That's, that's a great point. Like, so you're ghost— like you basically have all the content and then the ghostwriter just comes in and helps repackage it in the stuff.

There's not a single thing they wrote that was original that wasn't my idea.

No, that's like— I see nothing wrong with that. Like, that makes sense. It's a lot of people literally do try to outsource the original thought creation to somebody else and you can't do that.

What do you think about company accounts on LinkedIn and Twitter? Are they even useful to do?

Yeah, but you have to do it right. Like there's— so Duolingo, their socials are insane. I mean, they're the one everybody points out, but they're really good. Not every company like Goldman Sachs couldn't come in and try to do that stuff. Or like when all these Bitcoin ETFs got launched, Franklin Templeton tried to do the whole like they put the laser eyes on the Benjamin Franklin emoji.

Really?

Yes.

I had no idea. It just looks so cringe because this is like a really old asset manager, right? Like like, it's, it's like the meme, how do you do, fellow kids? You know what I'm talking about? Um, so it just looks cringe. I think brand accounts can be super valuable if they're entertaining but informative. Like Duolingo's brand kind of fits their vibe. It's this little weird green owl that like pops up on the screen and they like, they're like, their social team is very plugged in with what people think about them. Like the memes about the owl, like being intimidating or it's gonna kill you if you don't do your Duolingo. Like they'll riff off of that. Ryanair does the same thing. They're a budget airline that knows they're a budget airline where they actively like kind of antagonize their customers that are like, oh, the window on my plane's so small, or these seats suck. And then Ryanair will tweet back, wow, like you're throwing shade from row 37 of a Ryanair flight. Like, what'd you expect? It was $14. That's funny. But Delta couldn't be saying something like that about somebody who was annoyed because their first class seat service wasn't good. So I think it, it's honestly way easier to do social media brand when you have either like a very funny personable account or something that's like not a luxury brand where you can riff a little bit. Um, but like McDonald's social team is great. Like they do very good social campaigns, very plugged in and it's not as immature or aggressive, but it's still very conversational. Um, honestly, like Morning Brew back with Toby. I don't know if either of you guys know Toby Doyle, but like he was very good on their socials after he left. Like their socials were getting less engagement. I have no idea who's doing it now, but like their socials are like good again. So it does matter because if the content's good, people are gonna engage with it more and it's more front of mind. But if you, you don't want to be like a tryhard brand who's like, it's such a feel thing. Like it's such a vibe thing. Like you can't really, there's no way to quantify a good formula for like good brand content. It's just when you see it, you know it. Brands that are really good at it are really good at it, but brands that are really bad at it, it's just cringe.

My perspective on it, even though I'm less qualified than you to give my two cents on this, is that if you, if you're not in a place as a brand to be able to push the boundaries on like what's considered normal, like humor comes from the fact that you're either like making fun of yourself or you're doing something that's unique. Most brands, to your point, like you JP Morgan is not going to go out there and just like start making memes that are going to compromise their broader professionalism as a business. So I think just the value of business accounts versus personal accounts is relative to the type of business you're building and where you stand on the spectrum of like high quality versus, you know, something that's more discount where you can be hilarious and make jokes about yourself.

Yeah, like with JP Morgan, I don't know, like Jamie Dimon would be the— for JP Morgan, like he kind of is their brand, right? But he's very good on television. He's like, anytime he's in a press conference, he's fantastic, well-spoken, well-respected. And then his clips circulate a lot on Twitter. So I hadn't really thought about it like that before, but it kind of makes sense how like the more, I guess like the more professional the company is or the more like buttoned up they have to be, the more their brand needs to be reflected by respective figures within that company, whether it's the CEO or the CMO, or for like anything finance related, it could be like, like with a lot of VCs, the brand for VCs are like the investors, right? Like Lux Capital, Josh Wolfe is one of the founding partners there, very active on Twitter, but he's not like sarcastic or like, like he's not doing like the Duolingo stuff. He's like putting stuff out there about this defense tech, this defense tech company they invested in, or like these cool developments in this biotech company. It's like this nerded out sci-fi thing, but that's their brand and that's like Lux invests in companies that are like pushing the boundaries on tech. So yeah, your, your brand, whether it's the company account or like figureheads within the company, it kind of needs to match what your company's vibe is. Like Josh Wolfe, sci-fi nerdy stuff, super cool, like real life Tony Stark type of stuff. That's what he's putting out there. That's what they invest in. Dueling is a social app with an animated green cartoon owl. They should be funnier and kind of like picking at their audience.

As someone who's definitely leaned into content more over the last 12 months than ever before in my life, I think a question I have for you as someone who has a legitimate audience, what would you say to people listening about consistency and maybe strategies that you've used to be able to maintain consistency and even ways where you maybe you get into creative ruts? Like how do you find your, your way out of that?

I think for the, for the consistency thing, it's like, you can't confuse outward results. By that I mean engagement, likes, retweets, follows, whatever, with like quality of content. Because when you have a smaller audience, a lot of your stuff won't get seen and it could be really good. Um, and even when you have a bigger audience, like I'll put out stuff that I think is good and it just doesn't get that much engagement. But with like a blog post, I repost old stuff all the time. and something I wrote a year ago may have gotten like 20 or 30 likes when I posted it, and then it'll get 300 now just because more people happen to see it for whatever reason. Um, so for consistency, it's like you'll, you can really get down on yourself if you feel like not enough people are seeing your stuff. I think especially like it's a little different with like TikTok and Instagram, cuz if you catch the viral algorithm, you can get a lot of views very quick. But if you're writing or even if you're doing like YouTube videos, I think it takes a little bit longer or a podcast. So you really shouldn't be that concerned with like engagement for the first 6 months. And that's if you're doing stuff every week. Like with my blog, I've got like 50,000 subscribers now, but when I started I had like 200 and it was people I knew and it took me 6 months to get to like 500. And then I went from 500 to 700 in a week just because a couple of people who had big followings read a piece I wrote and shared it on Twitter. So there's a lot of random, one-off tail events that drive a ton of subscriber growth, but you're not gonna have that many early on. Like you just have to keep putting stuff out there. As far as creative ruts, I don't, I've never really had an issue coming up with stuff to write about, but I think that's because I haven't overly niched myself down into a particular thing. Like I will write about anything that I think's interesting. I wrote a blog post about how, like when I was like, I'm still working on improving my Spanish, but when I kind of doubled down on Like, okay, I actually wanna get better at Spanish. I was looking all over the place at resources, best ways to do it. Tim Ferriss had written a lot of stuff about it. I found a website where you could find like somebody from Colombia to do one-on-one, like Spanish lessons with for $7 an hour. I compiled all that into a blog post for my finance blog. It was like how to more efficiently learn a language. It was just something that I was interested in that I thought people would find valuable. Tim Ferriss ended up seeing it and like sharing it in his newsletter and it gave me like 400 new subscribers. Like, But it's, if I was sitting there thinking, oh, I need to have like something very specific about what's going on in growth stocks today, wouldn't be able to do that. So I think if you over-niche yourself in a certain like corner and it's not something where there's constantly a million stories, it can be really hard to come up with content. So like you want people to kind of understand what your vibe in general content is, but you don't want it to be so specific that like you're going to run out of stuff to write about within a year.

Yeah. One of the things I like about your account, and I think why I was drawn to a lot of your content, it actually reminded me of old Tim Ferriss content because his old content, yours included, it's always talking about your first-person experience. And as a result, you can kind of talk about whatever you want, right? Because it's not how to learn Spanish in 10 steps. It's, hey, this was my experience. This is where I fucked up. This is where I learned some things. Maybe it'll be useful for you too. And so many of the founders that we work with with that verbatim, or that my friends are using ghostwriters for, or that they're trying to build their voice. They're trying to structure everything from the lens of, I am the expert here. Yeah, here's how to do this. And it doesn't resonate versus, hey, I'm trying and I'm learning and I'm failing. Maybe this is helpful for you too.

No, that's, that's a good point. And like, if you look at a lot of people who have kind of gotten big in the internet content phase, like Tim Ferriss, Mark Manson are probably two of the biggest ones. James Clear. People who've sold millions of copies of books in the last 15 years that were early on the blogging, most of their early blogs that resonated were stuff like that. Like Mark Manson was writing a dating blog and a lot of it was like his screw-ups, like approaching women or stuff that he learned from relationships and this and that. Tim Ferriss was talking about like how he almost killed himself because he was so burnt out from his company and his girlfriend left him. Or like a lot of stuff from like, he traveled for like a couple years after like All the basis for The 4-Hour Workweek. Yeah. He wasn't trying to make himself like the expert. It was all lessons learned. And people love anecdotes like that. Like they don't wanna be, they don't wanna be preached at like, I'm perfect. Here's what you're doing wrong. They want it to be relatable cuz every single person has issues that they're having with their companies. Like whenever there's an, I remember reading a profile on Elon Musk a few years ago and it was talking about how like he had to fly back from his brother's wedding early to like go to one of Tesla's factories cuz production was down. That personifies, like, that makes him real, right? He's not this multi-billionaire god. He's a very successful guy who has a lot of problems. Or when you read about like Warren Buffett, best investor ever, his family life is kind of a mess. People like reading real stuff. So I'm not saying that like every founder needs to go out there just writing about like failure after failure after failure, cuz you don't want your whole brand to be, hey, I'm always screwing up, but like overcoming failure or working through stuff or just personal anecdotes in general, people love, like you don't have to be the, Like I'm putting out a mental model every day. Like, I don't— like, I hate all the mental model, really vague, like, here's how you be more productive, this and that. Like, no, talk through, like, when you were struggling through job stuff or like what a big personal victory was, like when you closed your Series B. That's the stuff that people care about.

I think it'll also blow your mind when you start creating content, when your most viral piece of content was something that you wrote, like walking for 10 seconds on your way to, like, Subway. And you're like, wait, I sat for an hour trying to construct this long thread about X, Y, and Z. And it got 10 likes, and then I was just like shit, shitposting about something I was feeling that was authentic and true, and it went viral. And then you start to really get in your own mind about why is that the case? And it's because people want to know the person behind the screen. And yeah, like, share, you win, so people can learn, but authenticity is the most important thing. And the other thing I'll say too is that if you're not getting an immediate feedback loop, that doesn't mean that you're not impacting people out there. Like, I have, I don't know, 1,500 followers on Twitter. That's nothing, right? But my roommate yesterday was like, dude, I met this guy at an event he was at. He's like, yo, do you know Ben Sharf? Like, I love his content. I've been following it for a while. I'm like, wait, someone like reads these? I thought that was kind of like a joke. And the reason I say that is because I do think there are a lot of people out there that are consumers that don't necessarily engage through commenting and liking. And so that's all to say, if you're someone new in the ecosystem of content creation, don't quantify the amount of engagement you're getting to be the only metric for like progress you're making or impact you're having on people.

There's also something like that you'll see as like once people's audiences get bigger and bigger, stuff that was decent that maybe got 10 to 25 to 30 likes when you have like 1,000 followers, you can just reuse your own content. Like there's no rules against that. If I have a thread, obviously if it's super timely, time sensitive, you can't. But like if you write something interesting, like I've done, so there's one specific one I'm thinking of. I remember reading some blurb about how the Mormon Church had like a $120 billion investment arm. And I was like looking into it and it was insane. Like they had more money than the Catholic Church despite the Mormon Church having like, I don't know, a couple million members and the Catholic Church being like a billion. So I went on a really big rabbit hole and was just reading about like how they've invested their money since the '60s and like how they avoided paying taxes because they're a church and it's a nonprofit. Put this whole thing out there and it got like 5,000 likes on Twitter and I didn't have that big of a following the first time I did this. And I was like, the dopamine hits were insane. So a year later I posted the exact same thread and this time it got like 20,000 likes because it's one of those things that people, and I'll tweak it a little bit if there's new information, but like it's just a really interesting story that people, a lot of people don't know about. And okay, a few people are gonna see me tweet that and realize I've tweeted it before. Nobody cares. Like there's a lot more people who didn't see it the first time that'll appreciate it the second time. And anyone who liked it the first time isn't all of a sudden gonna like block you on Twitter because you reposted something.

Dude, if someone has enough free time in their day to be like, oh my God, he posted the same thing 8 months ago, like, right, that person needs to go talk to someone because that's crazy with the amount of velocity of content out there in the world.

Yeah, but it can feel like once you've written something, it's like, oh no, I can't copy myself and do that again. You're the only person who's going to realize how much you've written about one thing. So like, it makes sense to resurface and reuse stuff if it's good and engaging. Like, nobody has the creative bandwidth to just put out a banger every single week. So like, when you have something that really hits, it'd be insane not to reuse it a few months later.

Yeah. I'm curious in your journey so far, and one of the reasons we call this Turning Pro— have you read Steven Pressfield?

Yes. Okay. Fantastic.

All right. We gotta talk about it then. So you're prepped. So was there a part or was there a specific moment or like week span as you started publishing more of your own content and more of your own voice across socials? Was there a moment that it went from, oh, this is like a cool kind of side hobby, just something I nerd out about to this can lead to like real career opportunities, meeting really cool people in really impressive rooms. Was there a moment that you really started to take it seriously?

Yeah, there were. I think there were like 3 that were all really early on before I was actively making money from any of it, but I started to see the upside from it. Um, I wrote a blog post like this is probably a little over 2 years ago now about how like I'd lost a ton of money in one day trading stocks. So I tell the story a lot, but basically I turned like one Roth IRA contribution into like 8 times my like first job salary just trading SPACs. It was insane. Like it was way too much money to make as a 23-year-old hitting buttons on your phone. Like I was creating zero value and making so much money.

Was this early SPAC boom?

Yeah, it was like 2020 slash the first 2 months of 2021. Um, and then that bubble popped. I didn't lose much money on that, but I was so addicted to like trading stocks or whatever. That I was like, oh, I did so good on this, I'll just like start day trading random stuff. And it turns out that like, just because you have one edge and one niche does not mean you should extrapolate that to like everything. And I ended up, long story short, losing like $150,000 in a day, which didn't feel good because like it was so stupid. But anyway, I wrote a blog post on the whole thing and really like dove into the psychology behind like what was going on in my head, like both the actual mechanics of what I was trading, why I was trading, but also like how all those dopamine hits were messing with me. Like all I wanted was more money, more money, more money. And it was like, I don't know, it was just like, like injecting a little like mouse on a treadmill with like dopamine or something where they're just like addicted to it. And, um, so I wrote a blog post about the whole thing and Nick Maggiulli, who's the chief operating officer at Ritholtz Wealth Management, They're a big investment firm in New York. He's got like a finance blog and he also had like 100,000 followers on Twitter a couple years ago. And he tweeted something about how people shouldn't actively trade stocks because it's kind of like a fool's game. And I was, I just replied to it and said, yeah, like I thought I was smarter than everybody and then I lost $150,000 on one trade. Like I wrote a blog about it and he DM'd me and he was like, This is insane. Do you care if I share it? And I was like, go for it. And when he like tweeted it out, it blew up. And that was the first time that somebody who was somebody like big following verified on Twitter back when that actually meant something, has like a real job in finance. That's cool. Who was working on a book, shared something I liked. Um, a few months later, Morgan Housel, who's like a partner at Collaborative Fund, and he wrote the bestselling finance book of the last few years, The Psychology of Money. Follow me on Twitter.

That was literally— not to cut you off, I was about to bring that book up next as something you said. I just finished it.

Oh, it's great. Um, but yeah, he followed me on Twitter again, like, only a few months after that, I think because him and Nick were friends and he saw some of my stuff. And then Austin Reef from Morning Brew hit me up a few months after that saying he liked my stuff, this and that. So it was like 3 different people who are super, super successful kind of in the finance media field like my stuff. So that was the point that I realized, all right, these guys are way ahead of me, but they think I'm good. So there's probably some momentum here and I need to double down on that.

What actions did you take based on that? Like, I'm gonna post more, I'm gonna write more. Did you start taking it more seriously as a creative outlet?

Yeah. So I was at this point too, the ad market for newsletters is really good. So Packy McCormick, who writes a newsletter called Not Boring, was making like, I don't, I don't know what the numbers were, but like he had companies that were paying him to write sponsored deep dives where it was like a marketing thing where a company raised their funding, wanted a marketing campaign, and he would basically do a business breakdown, share it with his audience. And around this time I had started working with Litquidity, the popular finance meme page who has a big daily financial newsletter called Exec Sum. I'd hit him up on Twitter, just ask if he wanted help with it because I saw he had a big audience, big newsletter. I was reading it, I liked it, and he brought me on as like the editor for that. So that was the first time I was actually making money from any of this. Like I was just writing my blog for fun, but in the back of my head I was like, okay, I've got 2,000 readers. Once I get to maybe 15,000 readers, I can probably start selling ads on this. And I was at that point, I was thinking maybe like 10,000 readers, I can make $1,000 an ad. And then I just was multiplying that 50,000 readers, $5,000 an ad. This could get really lucrative. Because that's about what ad rates were at that point. So we would occasionally have startups that would like pitch us for marketing campaigns and we would say, hey, like we can do a regular ad campaign or we could do a sponsored deep dive where they'll pay us like X thousands of dollars and I would get a cut from the revenue from that. So like my first business venture in this was getting paid to edit Exact Sum. And then I would also write these deep dives, um, and get like a pretty healthy chunk from that. And then I was just writing my blog thinking in the back of my head, once I hit like X number of subscribers, I'll start running ads, which I did. So it was kind of like ExactSum was the first thing I was getting paid for while I was still writing weekly and publishing my own stuff, building my following. Like, so the, like the turning pro part was literally making money from ExactSum, but longer term I knew that my blog would get big enough. It could become its own business thing. What I screwed up was thinking that ad rates would stay at that elevated point forever. Obviously ad markets are volatile. And a lot of funding was raised in 2020, which a lot of companies were throwing at newsletter ads and this and that. And then funding cuts back and marketing spend is one of the first things that gets pulled. So, um, yeah, that changed how I looked at the business stuff a little bit. But yeah, initially it was like ExactSum is a business thing with the longer-term goal of like turning my blog into a monetizable asset.

Yeah. Can you catch us up on what's happening in the newsletter market quickly? Because I feel like there are waves of of Morning Brew got acquired, Hustle got acquired, Milk Road got acquired, Substack launched, raised a bunch of funding, and then I feel like there's a lull. And then all my friends are now launching newsletters again. Is it profitable? Is it worth doing?

Can I ask a clarifying question before you answer that? Is there— this might be a stupid question, but like, what's the distinction between saying blog versus newsletter? And like, why would you do one versus the other?

It's literally just a— there are some things that are literally newsletters. Like, Exact Sum is a newsletter. It's a daily compilation of earnings recaps, M&A news, VC funding news, bankruptcies headlines newsletter. I call mine a blog because I'm not really reporting on the news in my head. If it's like a truly, like you're talking about what's going on right now, it's a newsletter. If you're just sharing your thoughts with the internet, it's a blog, but blogs used to just be web only. And now that there's email distribution, which used to be a newsletter thing, it's kind of gotten mixed. Like I write a blog, but I send it to people every Thursday.

Okay. So they're, so just, they are interchangeable in the con— you're still fundamentally sending something into someone's inbox at a cadence.

Yeah. So I don't know, like I call it a blog because like I think a blog is just somebody like putting their thoughts out there, but this newsletter sounds more professional. So people just say that.

I'm gonna, I wanna tweet literally right now. You can answer the question. Like, can someone tell me the difference between a blog and a newsletter? Cuz I have a feeling that I don't know if that many people are gonna know the answer to that.

Yeah, I, I think blog, or I think newsletter sounds better. People think blog is like a casual pastime. Newsletter is like, oh, this is like an asset. It's a blog post.

Well, didn't used to be in like Tim Ferriss era when he first started blogging.

Right.

That was the thing.

Yeah. Well, that was like the, the original blogging was just having like a WordPress website where you were putting stuff out and maybe people had like an RSS feed where they were getting it. Um, but Beehive, Substack, ConvertKit, Mailchimp, they made it where you can just publish anything you want on a regular cadence and send it to email addresses that you have. So that was the big shift. But newsletter market specifically. So if you go back 10 years ago, newsletters weren't really a thing. Like Morning Brew was one of the first big pure newsletter plays and they had to build their entire tech stack from scratch. Like they had a referral system. They had to build that. Marketing channels, like nobody was allocating meaningful marketing budget newsletters. They had to go like their sales team, which was probably just like Austin, Alex, and a few of the other early employees were out there just pitching it to anybody. But they built an entire stack and they built like a massive, I think they sold for like $75 million to Business Insider. Like they, they crushed it. And then after Morning Brew launched, Substack hit the ground with Substack, I think was the first one out of this kind of newer newsletter thing where their business model was, we're gonna set up like a, like a payment processing thing where people can pay you directly to read some of your content. Because I think they were trying to get to where they're trying to help journalists be independent. Like if you have 20,000 readers and 2,000 of 'em are down to pay $5 to $10 a month, you can make good money from that. So a lot of people started launching newsletters or personal blogs on Substack because also you didn't have to like build a website and do all this. Like they just gave you all of that. Like I would've never wanted to build a website. I started off on Substack. It was great. I switched to Beehive because Exact Sum was like the first big newsletter going on Beehive.

I remember that.

And then for me it was just easier having both on the same platform early on. Substack was better. I think Beehive's better now. But because there's so many platforms that are like, like Beehive, Substack, ConvertKit that make it really easy to have a newsletter or a blog, everybody's launching one. I think that's a good thing. I think everybody should have on top of social media, like your own place to distribute your own thoughts where you can't get deplatformed. Like I like having a blog where I can put longer form, more nuanced stuff under my name. And I like having an email list that I own. I think as a business, the really big newsletters that have like hundreds of thousands of subscribers are still really good. I think the micro influencer, like 10 to 100,000 readers selling ads on that is just not a viable thing anymore because the cost per ad has gotten dropped so much. Like if you're a spot, if you're a company, that's sponsoring stuff. Beehive has an ad network. ConvertKit has an ad network. There's SparkLoop. There's all these things where companies can allocate $20,000 to the Beehive ad network, and then they give like a low, like a lowish cost per click to a lot of different newsletters where it's better for the company to do that. If you're an individual with like 30,000 subscribers, you don't have a lot of leverage to negotiate ads. I do think that for those smaller newsletters, there's a lot of upside of having like affiliate deals.

All right, boss. Also, we're at 50 minutes.

We got like another 5 or 10 minutes.

Finish this rant and then we can—

We're back.

Yeah, you said affiliate deals.

Yeah, there's— if you have like a smallish— like I have 50,000 readers, I would put that on the smallish side when you're talking about like business of newsletters, having affiliate deals that are higher paying where you might get 1 or 2 conversions, but you could get a couple of thousand dollars. For example, Rite of Passage is this online writing course that David Perel runs, and I love his podcast. He's fantastic. He has a very, like, good reputation as a writing coach, and it's a high-ticket course. Rite of Passage is $4,000 to $8,000. They have an affiliate deal that pays 30% on that. I'm writing a long-form blog, putting my thoughts out there. His whole thing is, like, teaching people how to write and build their voice and brand online. It's a very good overlap of, like, my content with his program. So I have an affiliate deal with them now where I get like a 30% conversion. Maybe 2 people click that link and convert, but that's like $4,000 in revenue and it's valuable for him. It's valuable for me. It's valuable for the reader versus I used to do broader, like ButcherBox, the meat delivery company. I use them for a while. Like it's a good product, but it's just not as lucrative for me to run an affiliate where I get $30 a pop if like 100 people or 50 people sign up. So Building out affiliates like that or having a paywalled newsletter that's a lot more niche. Like if you're writing about what's going on in a local, like geographic area, or you have a super, super detailed, like we were talking about the Bills earlier. If there's somebody who is everything Buffalo Bills and for like $8 a month, you can get injury report, draft rumors, trade rumors, whatever. You're going to have a couple of thousand diehard fans who would pay for that where it's lucrative. So you either have to get super niche and informative where people pay for that, or find either affiliate deals or your own products that you can market through it. But like the days of having a 30,000-person newsletter and making like $150K off of Athletic Greens ads just isn't really a thing anymore. Yeah.

I mean, I, I've learned so much from this. I, I think the, the, the thing that I've realized from what I'm hearing from you is that if you have a smaller audience, if it's very niche, there's opportunity there. But if it's like, if it's a smaller audience but it's broad, it's not, it's not as lucrative. And I'm also just interested to see what happens when like broader capital markets evolve, right? Like we obviously know right now money is not available the way that it was in 2020, 2021. So I imagine the newsletter market, the way every other market kind of goes up and down, will probably shift again. And so for those people who stay consistent like yourself, you're probably gonna to be able to benefit from that on the back end of it.

Well, there's one other benefit to like having a newsletter, or in this case like a personal blog that people don't think about as much. It's not just monetizing the content directly. It's like the stuff that comes off of that. Like I'm talking to a few companies about a few job opportunities now, and it's because people have been reading my stuff for a while and like it. There's speaking engagements, there's book deals, there's employment opportunities. Even if the like asset itself isn't that monetizable, it can open up a lot of doors that are very lucrative. Like people think I'm a good writer, even if I can't monetize my blog to the point that I thought I would've been able to 2 years ago. If people who think I'm skilled and wanna hire me to do stuff because they found my blog are willing to pay me good money, then that's like just as relevant, if not more than monetizing the content itself. So like one of the biggest upsides to that is like, even if you have 10,000 readers, if any of those readers are valuable and good for your network, it could be a very like lucrative and value-add thing regardless of if you ever monetize the newsletter itself.

100%. Well, man, thank you for coming on. I know you got a run ski trip. Talk to that camera. Tell people where they can find your newsletter.

Um, my newsletter is at youngmoney.co. The dot com is taken by Lil Wayne's record company, so that's youngmoney.co. You can find me on Twitter and LinkedIn at Jack Raines too.

Oh yeah. Thanks for coming.

Thanks for coming on, man.

Thanks for having me, guys.

Awesome stuff.

Cool.