How to Write a Winning Newsletter With Jack Raines

Welcome to The Marketing Millennials, the no BS marketing podcast. I'm Daniel Murray, and join me for unfiltered conversations with the brains behind marketing's coolest companies. The one request I tell our guests: stories or it didn't happen. Get ready to turn the fuck up. Growing a newsletter is hard. There's no clear-cut playbook on how to do it and how to make money doing it. Today I chat with Jack Raines, the creator of Young Money newsletter and blog, and also a writer for Liquidity. We talk about the steps it takes to start a newsletter, why cross-promotion is so important, and why having a social media present is key to growth. Look forward to all of you hearing this episode. What's up, Jack? Welcome to the podcast.

What's going on, Daniel? Thank you for having me.

Yeah, I'm super excited. I want to get started and ask, how did you get into creating newsletters and marketing?

I graduated from college in December 2019 and then started working in a finance role in Atlanta. In March of 2020, which is probably the worst time possible to start working a new job. So we go remote like 4 days after I'm in the office, right? And my job was pretty boring, just finance spreadsheet stuff. And in August of 2022, I was supposed to start business school up in New York City. So I'm working remote for a year and a half, right? We get to the summer of 2021 and I'm like, okay, I wanna go travel for a year before I start business school. I have some money saved up. So I started applying for all of these writing gigs with the Morning Brew, um, with all these different either finance newsletters, publications, nobody would hire me. So in my head, I figured I would just start my own blog or newsletter on Substack, write for a month or two, and then have like a portfolio that I could pitch when I wanted to apply for one of these companies. So the whole origin of me writing was just trying to build a portfolio that I could use as like, a resume or evidence to get like a remote writing job with Morning Brew or really any company that was hiring.

I mean, that's great advice for anybody starting out too. If you want a job, especially like coming out of college or starting in a new role, if you can create a side hustle to prove that you've already done the role that they're looking for, it's so much better on, on the resume.

Oh yeah, 100%.

So you're really passionate about finance and newsletters. How did you go about starting your newsletter? And then how did that end up getting you your first writing gig with Lead Capital?

Yeah. So I was, uh, the whole time during the pandemic, I started trading stocks heavily, like pretty much every other 20-something-year-old guy that was stuck working at home. And I made a pretty significant sum of money pretty quickly. And then I blew about half of it, but I managed to cash out and keep some of it. But I was like, okay, like probably should stop trading. This isn't really a healthy use of my time. And it's a little bit addicting. But while I was doing that, I'd started writing these stock articles about different companies on Seeking Alpha. I saw that they would pay like $100 an article. So that was kind of my intro into writing. And I was like, okay, like I've developed a way to kind of paint a story about these different companies. And a lot of people kind of knew me as a finance stock investing guy just because I wasn't exactly quiet about my trading and stuff like that. So it just kind of made sense. The natural transition was to just start writing a blog about finance and stocks, and I didn't really know where I was going to go with it. My early articles cover everything from my thoughts on cryptocurrencies to whether you should rent or own a house to how investors behave in bear markets. But it really all started because I was writing like articles on Seeking Alpha, right? And then I start my blog and then I see in July or August that Liquidity has a newsletter called Exec Sum. And it's kind of similar to the Morning Brew where it's like a, it's a curation of like we have, or they had earnings recaps for different companies, news about what companies are raising like venture capital funding, who's acquiring who. It was very much a curated list that was useful for people working in finance to just keep an eye on what's going on. So I DM'd him on Twitter and said, hey, I love your memes. I also love your newsletter. Um, I've been writing a finance blog for a couple of months now. Here's some of my stuff. I would like to come write for you if you're interested in kind of growing out your content. So he liked my stuff and we got on the phone. And then we just kind of started talking about different ideas. And that was the first time I realized you can actually make money from writing online, like not being a staff writer with a company, but just having your own thing. Cause he was telling me about like how the ad revenue side of it works. And it just really opened my eyes to what you could do with that. That was kind of the moment where the gears started churning in my head, like, okay, you can actually make a significant amount of money writing online if you have a good audience.

Yeah. What are some things you've, you've learned as you've built your newsletter? Like how did, from day one starting it, how has it changed over time and how have you acquired new subscribers?

So I guess I'll take a step back. So like my newsletter, which I would probably call a blog, cause it's not really that much news stuff. I know the two words are kind of thrown around interchangeably, but it's called Young Money. And I put out an article every Monday or Thursday about something money or career related. It's the general, like, theme is pretty broad, but I've found that the first few months was very much just trying to find my voice, like trying to figure out what articles you're going to write about, what tone you're going to take. Are you going to be informative? Are you going to be casual and conversational? Is it going to be current events or more timeless stuff? Is it going to be about specific stocks or like the psychology of investment behavior? So I was really just throwing a lot of stuff at the wall and throwing it on Twitter. And right when I started my newsletter, I got about 200 subscribers immediately from Twitter, Instagram, and LinkedIn, just because people thought that I knew a decent amount about money. But from there, it was seeing which articles people commented on the most, which ones got shared the most on Twitter, and I was just aggressively promoting everything I was writing on social media. But the real inflection point came about 4 months in. I had written an article a month earlier about how I lost like $100,000 in a day from day trading stocks. I, I had at one point made several hundred thousand dollars, and then I ended up blowing a lot of it in one day. And one of my favorite finance writers, this guy named Nick Maggiulli, he works for, uh, Ritholtz Wealth Management, and he recently published his first book, Just Keep Buying, about really investor behavior and how the market goes up over time. It's a good book. But Nick had written a post about the dangers of actively investing versus passively investing your money, and I just commented under his tweet and said, yeah, I have a personal anecdote about this. Like, I was actively trading SPACs for a while and I lost about $100,000. Jack Raines, and he read my post and loved it, and then he shared it with his audience, and he had like 90,000 Twitter followers. So like my number of subscribers jumped by 50% in a day just from him sharing on Twitter. And that was the moment where it hit me that it was like, until my audience gets really big, the number one way to grow it is finding ways to integrate my work into people with bigger audiences' conversations. And there's, there's a fine line there. You don't want to just comment, be a reply guy under Nick's tweets or Liquidity's tweets or Morgan Housel's tweets, replying everything. But if you've written something that's very valuable and very relevant to what they're talking about at the time, it is completely okay to DM them and say, hey, I really liked what you were saying. I wrote something about this, or to reply and put it in the conversation. And that was my first— I don't want to say growth hack, but my first tactic that really started to click, like just looking for opportunities to integrate my work. With bigger people's or bigger audiences.

I think the great part you said that I think it's like relevant threadjacking or relevant threadjacking of like bigger audiences. I think the part that people miss out on is that the relevant part of it and staying and commenting something that is valuable to that person who's tweeting that will actually create a conversation instead of being self-promotional, which a lot of people just try to be self-promotional.

Yeah, 100%.

So I think, I think you did that right and you, you pick and chose your moments to do that. One question I have is what are some challenges you see of growing online, growing a newsletter, content creation? What are some, whether that is a technical challenge, a resource challenge, a business challenge, what do you see?

I think one of the hardest things is that with most career paths, there's kind of a blueprint on how to do it. If you work in investment banking, you come in as an entry-level analyst, and then you get your reps in. After 2 years, you get a promotion. You can jump to private equity if you want to. You go get your MBA. Or if you're in consulting, you do this, this, and this. If you go to law school, there's a very specific path to make partner, right? Like most of these traditional white-collar career paths, there's a defined path to get from beginning to endpoint. With creating online, there's, there's no blueprint on how to do it. People have taken a million different paths. Like you guys at Workweek are pulling a lot of creators together to like, like operate your own individual content under one brand. Nobody has really done what you guys are doing. Morning Brew was kind of the first company to revolutionize the email newsletter and obviously they're killing it. Liquidity turned a meme page into a business, which That sentence literally wouldn't make sense 5 years ago, right? Like, he managed to monetize an audience through a finance email newsletter, merchandise sales, and he's killing it. And like, there's all these different ways to do it, and no two creators are going to be able to do the exact same thing to make money from their audiences, right? Like, in a very, very broad scope, there's three ways to make money as a creator. You either monetize through ad revenue on free content. Your readers pay a subscription to read your content, or somebody likes your content enough that they'll pay you to write for them, whether that's Bloomberg paying you to be a writer, or in Morgan Housel's case, Collaborative Fund hired him to write his blog and his essays like under their brand on his website. But essentially they are paying him because the association with his work is good marketing for them. Right. So you have those 3 very broad pods for monetizing work, but it's how do you figure out which path to go down? Like, how do you build the audience the best? It's the hardest part is there's just no defined track for, all right, this is how you make $100,000 every year writing online. There's no guaranteed way to do it down any of them.

I love that. I think there's not— there isn't a great path, and I think it also is very creator-based. I think Some people don't want to do ads because it's not their brand. Some people don't want to do subscription because they believe in the free model. Some people just are using it as a tool to get leads for something else. Right. Like, that's why I think like the creators sometimes who have like agencies or stuff like that and use it as like a lead gen— not a lead gen model, but really a way to build brand and get people in organically to your business, which you wouldn't have before. That's another way to do it that's not directly tied to you monetizing your work, but your work is helping you get reach to monetize and grow revenue for a side hustle as well. Yeah. What's like a, a marketing hill that you would die on that you right now? I mean, obviously it could change in a year, but what is something that you— a statement or something that you do as a creator that you would die on today?

I think I have two. I think one, people worry too much about growth hacking or marketing strategies, but at the end of the day, the best marketing strategy is producing phenomenal content. If you write an article that people like, they're going to share it. If you have a useful newsletter that provides a lot of value, people are gonna tell their friends about it. If your content isn't really good, it doesn't matter if you do paid ads, if you do cross-promotions, you can do whatever you want. Your growth isn't gonna be great and your engagement rate's gonna be low because the content is low quality. So if the content isn't just A+, nothing else in marketing matters. Like the content is effectively the most important marketing strategy. The other thing, and this might, like, you might disagree, different creators might disagree with this, but I think the most effective way for growing, like expanding your audience, especially in written content, like newsletters and blogs, is finding ways either through cross-promotions or just having websites that would like to share your content because they find it interesting, but finding ways to leverage other people's audiences. For example, ZeroHedge, which is a very kind of libertarian right-wing, like finance economics site. They post, like, they post a lot of stuff and they have articles going out all the time. But they have a massive reader base. Like millions of people are checking out their site every month. And I wrote this piece called "Fuck You Money," which was based on an Nassim Taleb quote about like the optimal amount of wealth and how it's not like a high end of a spectrum. It's a mid-range. Like you can effectively have too much or too little money where it lowers your quality of life. And Zero Hedge, I guess one of their editors had read it and they loved it. And they asked me if they could share the piece on their site. And I said, sure, like, yeah, that would be great because it's going to get a lot of traction. And if any of their readers like it, they'll subscribe to my stuff. Hedgeye, a big finance group, they same thing. They have me like basically cross-posting one of my old pieces on their site every week. And these are websites that get hundreds of thousands to millions of views. So I don't have to pay for the marketing because it's a win-win for them. It's more quality content to put on their site that they don't have to create. And they don't pay me for. And for me, they have a massive audience and I attract some of that audience onto my email list every time I publish. So I think that's the best marketing strategy I have, is just integrating my work into these bigger audiences and then pulling some of those readers onto my mailing list.

I don't think the Marketing Millennials, like, I don't think if you, if you see like the root of the Marketing Millennials, it's supporting other creators' work. And I think that is kind of what you're doing with that, sharing your work as a creator. I, I see myself more as a— I love creating, but I also like love curating. So I see myself as a curator. And I think a lot of the time it's like I'm not forcefully like— I don't— I'm not trying to piggyback off this audience, their audiences. But a lot of times when you give reciprocity off the audience, they end up sharing it to their audience. Like, so what you're kind of doing, I'm just like sharing, hyping them up. So we both have a win-win. They get a win-win because I'm sharing their content. And then when they like it, they share it to their audience. So it's kind of what you're doing, but in a different model. So I totally agree.

When it's with other individuals, like other people that are writing their own newsletter or blog, I think very similarly, even if it's sharing it on Twitter. Like I have over 11,000 Twitter followers, which is a decent-sized audience. And if I see an article that somebody wrote that's great, like I'm sharing it on my feed. I'll occasionally link if there's something, just a phenomenal piece that I read or podcast that I listen to, I'll link it at the top or bottom of, uh, one of my blog posts. So I agree 100%. It's, it's, it's 100% a win-win because yeah, creators should support each other. Like, we're all out here trying to accomplish the same goals. But if you have a bigger, like, institutional site like, uh, a Hedgeye Zero Hedge, or even like a Bloomberg or Huffington Post. If you could like have like an opinion piece that you submit, like those massive groups, they don't really need cross-promotion because they have millions of readers already. But if they're willing to share your stuff on their sites as an individual creator, it's just massive exposure that you can't get anywhere else.

Yeah, I love that. I, I see that all the time with people producing on Forbes and like marketing sites and stuff like that in the marketing side. I totally agree. I think it's a— if you're a good writer and can produce good content, and what you said before, like, if it's not A+ content, don't submit it, because otherwise it's just gonna make you hurt your reputation. But if you're doing what you're doing, I, I 100% support that strategy. So I know this is— the world's tough to predict right now, but What's one marketing trend you're seeing right now that marketers should jump on?

I think there's a bigger and bigger movement towards like, and I don't know if this would be a marketing trend or just kind of a content trend in general, but like the empowerment of the individual creator, which obviously you guys are right in the middle of that with Workweek. But like, like Trung Phan is a great example. Like that guy wears a million different hats, but he's kind of a solo entrepreneur running his courses. He's working with you guys. You write some Bloomberg. And if you're a marketer, being able to sign like either sponsorships or partnerships with individuals who are plugged in across like a number of different fields that give exposure, I think is one of the best trends to watch because I think it's a healthier partnership. It comes off as a lot more authentic than just looking like, oh, like I paid somebody to— like, you'll just see sometimes where you— it's like, oh, like they paid this company to tweet about this or this or that. Um, I think it's moving a lot away from the, the Bloombergs or the Forbes or the CNNs or the Foxes, like the bigger brands, where the individuals are kind of becoming their own brands. And I personally think that individuals have more engaged audiences because it feels more personable. Like if you're reading a specific person's content, it feels more like, you know, the writer, than if you're reading general Bloomberg content, for example. So establishing like business relationships with up-and-coming creators is probably going to be a very good return on investment like for marketers over the next few years.

I love that. I think the, the keyword like business relationships, I think don't treat them— not treating them like billboards and actually treating them like business entities. I think that's where a lot of companies miss. It's like, oh, they're just a billboard for my marketing campaign instead of Instead of like what they've been doing for years, partnering with other companies to do stuff or co-marketing, they, it's the same exact thing, but for, for a person. Moving to another type of section of the podcast, who are some newsletter writers or creators that are inspiring you right now?

A couple of my favorites are, so Kyla Scanlon, she's awesome and she's all over Twitter, all over TikTok. She writes a newsletter where she just breaks down everything from inflation to like, is Musk actually gonna buy Twitter? And her way of creating content where it's both incredibly informative and easy to digest, but also very funny, whether it's integrating memes or current references from pop culture, it's just such a, it's almost like a very conversational, like watering hole. Version of stuff that you would see in like the notes from a transcript from a Federal Reserve conversation, if that makes sense. Like she's managed to take just like these almost very boring, tedious finance and macroeconomic topics and make them just dynamic, interesting, and funny. And for me, it's both easier to digest and easier to remember watching her content. So like she's, she's one of my favorites right now. Outside of that, like there's, there's a few different ones. I'm a huge fan of what Trung has been doing with his Satposts. Cause he just has like another funny story coming out. Like it's always something random, you know, by not, it's almost like by not putting himself in a box of I'm going to just write about finance or this or that. He just finds interesting stories and puts them out there from the business of Red Bull to writing about his own television script that he put out last, last Saturday. So I'm a huge fan of both of their stuff.

I love that. I think in the trend of both of them is they, they know how to storytell and what— and they know how to simplify content for people. I think a lot of people, that's where they miss is— and that's why you're saying like these institutions, like news is hard to digest. Journalistic articles are great for society, but they're also harder to digest because you can't get a human personality out of it. It's more like reporting on something that's happening. I think journalists that add personality to their work really separate themselves. What is something if you were starting out right now, you would tell someone that they would thank you 5 years later? Like, what would you— someone starting a newsletter right now, what would you tell them? Or someone becoming a creator right now that they would probably thank you 5 years later down the road?

I would probably have 3 things, and some of them are very, very just practical, like get this set up now so you don't have to do it later. And then some of them are more about like the actual content creation. But the first one is think really hard about like the name or the brand that you want. And then stick with it. And then go ahead, if you're gonna have a newsletter or a blog, purchase a domain for it. So like, I went with a Young Money name and I love it. Like, I'm glad— I like— I'm a big fan of the name that I kind of went with because it's funny, sort of a play on words with, with, uh, Lil Wayne's like record label. But my mistake was I didn't have my own domain to start with, and I used to write on Substack, so it was Somebody already owned a Young Money Substack, so I had to edit it a little bit. So it was youngmoneyweekly.substack.com, because if you don't own your domain, you just get an auto Substack domain. So I got to probably 2,500 readers, and then I bought the youngmoney.co domain. And owning your own domain just looks a lot more official when there's not the .substack or .whatever newsletter platform you're on. It works a lot better with SEO when people are looking up in Google, it's like, oh, that's Jack's website. So I switched to Beehive, and I'm a huge Beehive fan. Anybody that's looking at starting a newsletter or blog, I would highly recommend using Beehive. Their team is great. But I bought my own domain and then set it up on Beehive. So now it's just— it's youngmoney.co. It's running on the Beehive platform, but it just looks like my website. But it took several months for my new site to become the top, like, search result over the old one, just because of the old links. I got so many clicks and it probably set back like my reach and my engagement by a few months just because it took a while for that to kind of filter through. Now, now it's kind of running again. If you search any of my articles, I've re-imported them to Beehive so they come through on the right site. But by getting that set up early and never having to change it, you just give yourself way more momentum as you start building. And then the, the other thing is when you're getting started, it's very hard to know like what direction you want to go in, because audience feedback plays such an important role in what you do. Like, we all say that we want to write whatever we want to write, but at the end of the day, it's about the audience. You have to engage them, so their opinions and feedback matters. So early on, kind of throwing a lot of different stuff at the wall and seeing what sticks. You have to decide at the beginning, are you going to be a curator? Are you going to be a creator? Or will you be somewhere in the middle? And you run with that. Like, I'm very much a creator. I write long-form essays, but Exact Sum, Liquidity's newsletter, is about 95%— or so. I'm a creator, but Liquidity's newsletter is straight up like curation. We have links to different sites. We put all of the important information that finance people would want in one place for them to find and act with as they want. So figuring out which way you want to go in the curation versus creation, And then when you go down that path, start throwing stuff at the wall. Like you might write about finance, but you'll throw a curveball in and mix it up a little bit and see, is it getting more engagement, less engagement? And then are people replying more to your email? Are they commenting more? Is it like getting more engagement on Twitter? And if it is, you double down on that. So the first 4 months is very much A/B testing what content is the most well-received.. And once you get about 6 months in, to me, that's when the ball gets rolling. Like, you have now gathered enough data to, uh, know which direction to go in with your content. And I guess one more thing while I'm thinking about it, gathering data on your audience the whole time makes it way easier to market your newsletter or blog to advertisers if you want to do sponsorships. So on my signup email, I have a very short 8-question survey that just asks like where you live, what your job is, what your income is, age, gender, whatever. I have 7,500 subscribers and I've had 1,000 people answer the survey. So that's a very good sample size of my total audience. So when I'm talking to different brands about potentially partnering with them, I can say my average reader is a late 20s, early 30s male that probably lives in the United States and works in finance or tech. And that's a relatively lucrative audience base, and I can charge more for sponsorships because of that. So to summarize, like picking your brand and getting a domain early, picking the curation versus creation path, and then just throwing a lot of stuff at the wall to get feedback, and then an audience survey. So, you know what your average reader looks like at any given time. If you do all of that and then just keep putting out good content, um, the ball will start rolling. Like the momentum will get going.

I like how you broke that down because I think, I think both of us just listening to you like fell into doing those two things. I think Mark, like Marketing Millennials, I didn't— was not thinking about ever writing anything. It was just a podcast. And but the name has helped so much in the long tail of things of like branding and stuff that I like— it's helped me down the road. And what you just said about getting that feedback, I'm glad I started on social media, so I have a good sample size on social of like who follows me. So it was easy when I was doing a newsletter to kind of gauge getting those answers, who is coming on my newsletter, who are the raving fans, who are not. So I think like a lot of it fell into me, but I, I like how you broke it down because I think those are such crucial points of—

sorry.

And the name is so underrated. I think a lot of people just name things and then realize later that the name doesn't hit. And I got lucky with that. But my first name that I came up with, if I went with that, I would have pigeonholed myself so badly. So I'm glad I—

what, uh, what was the original name?

It was just something in, in SaaS, and I was just going to be like a SaaS marketing thing. And then I was like, you know what, I want to talk more about like broader marketing because I just love talking about marketing. So, and I don't want to pigeonhole and just get SaaS marketers on my podcast. So I went with the Marketing Millennials, but it was just a SaaS play. But now growing Marketing Millennials, I can go back to the SaaS play because I can, I have this bigger audience and now I can capture a smaller audience in that. But I'm glad I started more broad and then went down because it also, what you said, it allowed me to test what content worked and what content didn't. If I niched myself very quickly, I wouldn't be able to test my audience like you're testing your audience. Yeah. The last bit of this, I just want to give you time to let people find you. Where, how are they going to subscribe to your newsletter? How could they find you on Twitter. This just give your time to promote yourself.

Yeah, sweet. So on Twitter, it's just Jack_Raines, so J-A-C-K_R-A-I-N-E-S. And then, uh, my blog is youngmoney, just spelled normally, .co. One other thing that I've been doing with my blog is I have a referral program set up where if you refer 15 people to my blog, I'll buy you and ship you one of my 15 favorite books, which has worked pretty well. I've sent 2 book copies to Lagos, Nigeria. Have a couple of readers in Africa. But if you do sign up and like my stuff, there's a link at the bottom of all my posts for your personal referral link. And once you refer 15 people, I'll email you a link to a Google Doc with a list of like my current 15 favorite books. So a little bit of an incentive. If you like my stuff, definitely tell your friends about it. But yeah, Twitter, Jack_Raines, and then youngmoney.co for my, uh, my website.

Cool. I love that. I love the 15-book thing. I think that's super smart. Yeah, I'm gonna have to check out what your 15 books are.

That's— yeah, yeah, I can, uh, I can, I can, I can just send you the list, and then if you want any of the books, you can, uh, Refer 15 people.

Refer 15 people. Yeah, exactly. Cool. Well, thank you so much for being on. This was awesome. I think really tactical way of starting a newsletter, becoming a creator, finding— I think I, I like how you're approaching it of finding ways to enter in conversations, whether it's with institutions or with personal brands. I think it's super smart.

I think a lot of people either do one or the other.

Um, so that's great.

Yeah, yeah, man. Uh, Daniel, thanks for having me on here. This has been a blast.