Audience Bridge Insights #7 - From Barstool to Leverage Letter — Voice, Scale, & Originality Tips

Foreign.

Welcome back to another episode of Audience Bridge Insights. I'm here today with Tyler Moran of the Leverage Letter and founder of the Water Coolest. I guess you're the founder of both of those. How are you doing today?

Good, man. I appreciate you having me.

Nice. So why don't you go ahead and share with the audience? Walk us through. Let's start back in the beginning, when you started the Water Coolest. That came. The idea came about, and then, you know what it's become since then.

Yeah, yeah, absolutely. So apologies to everyone. I've. I've shared the story probably a few times, but I'll. I'll give you the quick version. So I founded the Water coolest back in 2017, so it just became eight years old. I think my math is correct there, which is kind of crazy. So I was actually working, like, no media background. I was like, to tell the story of, like, I went to UConn. I loved writing. I always wanted to be a journalist. My parents told me that was a really stupid idea and that I should go be a finance major. I listened to them and I became a finance major. And, you know, lo and behold, I absolutely hated it. So I was always doing, like, these weird little writing projects. You know, as I was working, I was working in financial services consulting. And so the Water Coolest came about basically because I was reading about the banks and all my clients every day, you know, kind of required reading to keep up on the industry. And I was reading the Wall Street Journal, Bloomberg, and I was just like, this stuff sucks, right? Like, it's. It's super boring. It's, you know, it's written by old white dudes. And so I was like, why isn't there something where I can read this, where it's, you know, written like, I talk to my buddies while we're at the bar, right? And so started having this idea, you know, for a while and didn't really do too much with it. And so at the same time, I had been doing some blogging. The blogging really wasn't going anywhere. I didn't know how to get, you know, SEO, how to get anybody to actually read my blog. And so these kind of two ideas came together because I started sending out the blog via email, and I was like, oh, wow. Like, this whole email thing is. Is pretty interesting. At the same time, this was like 2016, like, the skim the brew, right? Like, some of these kind of. Let's call it, like, Newsletter 2.0. And so I started sending out just, like, these. These Kind of blogs via email, which is I, I still kind of how I look at, you know, the water. Cool. This is almost like a blog. And just started writing about like stuff that was going on in the news that that mattered to me. Stuff about, you know, markets, what banks were doing, all that stuff. But I was just like writing about it super irreverent, you know, I was cursing having fun with it. And it, you know, I started to send it to a couple hundred people, just like everybody does, you know, you scrape your, your Gmail, sent it to a couple hundred people, they started to like it and they started to send it around. And then I would say kind of got my kind of quote, unquote lucky break, which I think, you know, everyone, everyone kind of needs to have. And I basically started asking some of these finance influencers, you know, that I was finding, like on Instagram they started to become big, right? Like finance Twitter started blowing up and, and I was like, oh man, like maybe I could pay these guys to talk about this, right? Because they're talking about banking and finance. Kind of like I'm talking about it in a newsletter. At the time, none of them had newsletters. So I was paying these guys like 50 bucks. And I was getting 200 subscriptions or 200 signups. And they were at JP Morgan emails, at Goldman Sachs emails. I was like, oh, this is pretty awesome. So it actually started to take on a little bit of a life of its own, which was really cool. And that's like how we first, you know, got. Call it the first, you know, thousand fans or a thousand subscribers. And it really started kind of growing from there. Started doing all the, you know, the referral programs, stuff like that. So at this time I was still basically doing, you know, my finance consulting job. This was off the side of my desk, which was crazy that I was writing, you know, a daily newsletter and still working like, you know, 12, 15 hour consulting days. I was coming home and writing this thing. But I think it just goes back to like the passion I had for like, I just love writing. And now that I had some traction, like it was even cooler because no one read my blog. But now people were reading the newsletter. So fast forward a little bit. Basically got to a point where I was making enough money with the water. Coolest. We started selling some ads, you know, around like 20, 30,000 subscribers. And I was like, man, like this is a real business. At the time, newsletter CPMs were still like 40, 50 bucks. Um, you know, you could make a lot of money, a lot of people wanted to go direct sale. And so I was like, fuck it. Like, I'm. I'm leaving, you know, my consulting gig and went in all in on it full time. That was 2019. Between, you know, 2019, 2021, it grew like crazy. Uh, you know, I like to say it was because I was so good, but quite frankly, like, everything that happened with financial markets and the people I was talking to was absolutely perfect timing, Right? This is when, like, GameStop happened. Crypto was going crazy. NFTs, I guess, were a little bit later, but all this stuff kind of came together and there was just such hype and demand for this stuff. And I had already been kind of honing it and developing it, and of course, a lot of other newsletters came along, but, you know, I'd been around for a while and, you know, so I had kind of this head start. So, interestingly, I actually got in touch with some folks in 2021 over at Barstool Sports. I knew Large over there. He was a reader of the Water Coolist. I'd gone on some of his podcasts, just explained things like, what's a short squeeze? What, you know, what's happening at GameStop, all this stuff. So he actually posted after we did a podcast together in a Barstool blog about the Water coolest. I woke up the next day and we had, like, 5,000 new signups. And they were. I watched over the next couple weeks. They're crazy engaged. They're reading, they're sharing, they're writing me about how awesome this is. I was like, holy shit. Like, I need to be spending. Why am I spending money with Mark Zuckerberg and growing the newsletter that way? Like, I should be giving my money to Jay Portnoy and growing it that way. So I sent an email to adsuppartoolsports.com I said like, hey, you know, in dollars to spend. Which, you know, they probably laughed at me because they work with Bud Light and gm. And so I almost, like, immediately, probably like an hour later, I got a phone call and it was like. It was like, hey, I want to talk to you. I'm from Barstool. And I was like, what? Like, why? Why are you calling me so soon? Like, why are you so excited about, you know, newsletter? So as we're talking about the newsletter, I'm like, who is this guy? And, like, why is he asking so many questions about, like, my business model and what. I see the future of newsletters and, you know, what I want to do, you know, where I See this thing in a couple of years, like, what's next in media? I'm like, this is a weird question for an ad sales guy. So I literally look him up while I'm on the call with him. It ends up being the COO at the time of Barstool. So this stuff came. This came across his desk. Someone had sent it to him. They happened to be looking to get into the finance space a lot more at the time. Dave Portnoy was doing Davey Day Trader. That was blowing up. Obviously, all. All the sports betting was shut down, so they were looking to go into other. Other verticals. One of them was finance. The COO at the time, he loved newsletters. He had a background, like, he worked at Street Business Insider, and so he loved the business of newsletters. We started talking basically that day. We talked for like six months straight, actually. After a couple back and forths, Barstool ended up acquiring the water coolest in 2021, which was wild because literally, when I set out, there was probably only like two places that I actually wanted to sell to. And one of them was Barstool. One was Stocktwits. And I ended up kind of talking to both of them at that time, which was really awesome. And so ended up going to Barstool, was head of newsletter operations. Ended up launching a podcast there, which was really cool and fun. Probably could have gone better, but it was a fun, interesting experience. Large is one of the coolest guys on earth. And so it was really fun to do that. And basically, eventually, Dave famously kind of ended up buying Barstool back. A lot of things changed kind of in the, you know, between like 21 and 23. And so when Dave bought the company back, he was basically like, listen, I'm not super interested in newsletters. I'm not super interested in finance because, you know, sports gambling had come back. He wanted to, I think, you know, I can't speak for him, but I think he wanted to get back to the core of. Of Barstool. And so, right, you know, I'm sitting there, I'm the head of newsletter operations, which he doesn't care about, and I'm the finance guy, which he doesn't care about. And so I kind of saw the. We saw the writing on the wall, so we basically negotiated an exit, and luckily they were cool enough to let me, you know, end up taking the Water Coolest back. I don't know what would have happened to it if I, you know, left it there, but I ended up taking the Water Coolest back. So in 2023, after two years of barstool, I rolled out, you know, with the water coolest again, you know, which was. Which was really cool. Had no idea what I was going to do, right? Because there I had, like, a sales team and, you know, operations team, you know, a full media company, and here it was just me again. So it's a little bit scary. And so that actually is the reason why I ended up launching Leverage Letter, which is a newsletter consultancy. Because out of that, you know, a lot of people, when I announced that I was leaving a barstool, people reached out and were like, hey, would you want to come run newsletters here? Would you want to, you know, work on this project with me? I was like, no, no, no. Like, I want to just kind of figure out what I want to do. And eventually, like, people were. Kept asking me, and I was like, why don't I just, like, charge for this? Right? So it started with some, like, I'll call them coaching calls or, like, advice calls. And then people are like, well, can you just help me do it? And, you know, at the same time, like, I feel like it was weird. Like, newsletters obviously had this kind of renaissance in, like, you know, maybe like, 2017, 2018, 2019. And then they started to kind of have this other moment, which I think we're still in. And there was just this huge demand for newsletter consulting and people who are kind of experts in the space, as I'm sure, you know. And so that business has just kind of taken off. So, you know, I. I kind of formalized it, made this company called Leverage Letter. And the way we look at it is, you know, we're basically fractional chief newsletter officers. So we'll come in to typically, you know, a media company or a brand who's looking to stand up, you know, a newsletter. And we'll kind of do everything from, you know, creating content for you to helping you grow the newsletter. And it's been a really interesting experience. And now that business is actually not much bigger, but it is bigger than the water coolest, which I kind of never expected, but super exciting. So I know I said that was going to be short, but that's, you know, that's kind of my story over the past eight years.

I mean, you just knocked out my first five questions on that, the entire story. So don't worry about it.

Okay, perfect. Yeah. Podcast over.

So just going back to that time at Barstool, and you're obviously with the big, you know, pretty big media company. What did you learn there. What things did you maybe take away from there that you were able to bring back to the water coolers when you're doing it on your own, as well as. As you're participating in all these other newsletters for people and consulting and helping them out? Like, what did you maybe learn on. As a big media brand that you can bring to smaller brands that you're helping out?

Yeah, so I think there's like two big takeaways and there's. This was something like, you know, and I thought it was. It's funny because everyone, like, always asks, you know, about Barstool, like, oh, what's Dave like? And like, what's, you know, what's. What's Frank the Tank? Like, you know, that's like, always the first question when people hear I worked at Barstool and, like, the thing I always say is that everyone is like, exactly what you see on camera. Like, nobody's acting at barstool, right? Like, everyone's just like, their true selves and they've assembled a bunch of, like, super interesting characters and, like, that's truly their ethos and they lean into it. Like, it's not. Not just something like an act they're putting on for the camera. So, like, when I, When I sat down with Erica, who was still the CEO at the time, on my first day, like, she didn't have much to say. She was like, you know, Tyler, it's fairly entrepreneurial. Like, go kind of do what you think is going to be best for the company. And she's like, above all else, like, be yourself. And I thought that was just like, super interesting. Right? Coming from, like, a corporate finance or, like, you know, corporate background, it's like, oh, you have to, you know, you have to be part of the system and a cog in the wheel. And so my biggest takeaway there was, like, she didn't want my content to change. Like, it wasn't going to be barstooled. It was, like, still going to be the water coolest. And so I, I think that's a big takeaway for, you know, what I bring to clients now. And, you know, I, I tell a lot of them, like, I think newsletters, like, in 2025 really need to be, like, strongly, like, personality driven. Right. And I think that goes to just, like, really being yourself, whether that's more of a brand or, like, truly a creator. I think you just need to, you know, be able to show your, you know, your kind of true self is as cheesy as that sounds. But I think that there's just so much AI slop out there and it's so easy to produce like very generic content that the only way you're going to stand out in 2025 is like producing something that no one else can create. And the one advantage every single person has is literally like what's in your brain, right? Like nobody else can have your thoughts. I'm sure at some point neuralink will. But, you know, for now, no one else can have your thoughts, which is a huge moat. And I think that's what any creator or anyone building a newsletter, like I tell them, is like, we need to think about like what you can produce that nobody else can. And then I think the, the second biggest thing that I learned, and this was more on the business side is like my, my boss, who's a CEO at the time, like my biggest takeaway was like, he was just like, you need to like, think bigger about everything. And like that, yeah, sure, that's easy to say when you're at barstool because they have bigger budgets and like, you know, they have bigger reach and all of this stuff. But I think it's, it's really true. Like I, I came at it from such like when I was building the water coolest, like so risk averse, like I was thinking about, you know, on a subscriber by subscriber basis. But I think it, you know, kind of showed me, taught me to like, just take a lot bigger bets. And I think, you know, that's where even like leaning into, onto this consulting business, right? Like maybe I wouldn't have done that before. Like, maybe I would have stuck with the tried and true, which is, you know, the, the water coolest. So I think that was my, you know, kind of second biggest thing was like truly just kind of like think bigger about everything. It's like, okay, like if you're going to do this, you know, one kind of growth, you know, growth item or, you know, a growth tactic or something. It's like, how can you throw gasoline on that to make it, you know, next bigger? Like, can you go out and you know, work with some, some influencers to make it, you know, bigger or you know, I don't know, there's, there's a million different things you can do. But it's like always just like everything I look at and it's like when I talk to clients too, it's like, okay, that's cool. But yeah, that's gonna get us our next 5,000 clients. But like, how do we Think about getting our next 50,000 clients. So just like, I guess like thinking bigger and like thinking towards that, that next.

A lot of scale, scalability of things.

Exactly.

Got it. And as far as content goes, you kind of explained on the personality, edginess, you know, whatever you have going, how do you balance that with somewhat professionalism or providing good content that's valuable versus just entertainment as a finance newsletter. I mean, obviously people want to read to be entertained, but I mean, if the finance loser. You're hoping that they're going to get some value and help them make some sort of decision or reinforce whatever they're thinking.

Yeah, yeah, it's. It's something that I still, like eight years later, I still struggle with every day. Right. Is like that balance between, you know, I, I certainly lead with entertainment. Like, that's, that's the goal of the newsletter. And I struggled with that for a long time to being like, you know, because I think everyone talks about like all the gurus and stuff. It's like, well, what's the value of your newsletter? What's your value prop? And like, you have to get someone to read it. And it's like it was a struggle for me to not want to give somebody not investment advice, but like, something that could help them actually make money and commit to saying, hey, you know, you can get that. You will get some value here as far as, you know, true business news and financial advice, all that stuff. But like, the, the core reason you're coming to this every day is entertainment. So it's still something I struggle with, but I think one of the biggest things was like, putting some parameters around it and like building a voice guide that I, I'm really like, strict about. And anytime, you know, I brought in a few. It's mostly just me writing now, which makes it easier. But like, I brought in a few other writers to help out and there's just little things that, you know, I think force your hand and I would recommend, and I recommend this to all my consulting clients is like, get serious about like a voice guide and a brand guide. And like, one of the things I do is I'm no joke, as I, as I like to say, or like, no entertaining piece should be more than like two sentences of just pure entertainment. Right? So, like, I can talk about, you know, the Fed, but I can't just go off on this long rant like trying to build to a joke or something like that. It's like I need to tie in something that's like factual or helpful or valuable. In at least like the next sentence, right? So little things like that have kind of like forced my hand and trained me and like, I've trained my brain to, to do it. But, you know, the balance is like, is always difficult. And some days it's, you know, I reread the newsletter. I'm like, okay, this is like a pretty, like, value add, you know, commentary, but it's like commentary on the markets and like, my thoughts on the markets. And then some days it's, you know, truly kind of just what I would call more of like barstool blogging content where it's like, I'm clearly just kind of having fun. And I think it's, you know, it's just a matter, you know, it's definitely a delicate balance that, you know, I, I kind of think about every day still.

Outside of the water coolers and the clients you're working with, have you thought about or, or have you already started creating another newsletter that might be outside of finance, that another something you love to do or, you know, passion of yours just to launch something else?

So I actually have to. I stopped myself probably twice a week from launching a local newsletter. And you guys can probably hear the.

Hot thing these days.

I know, I know in my, my town it's like, you know, it's Fairfield, Connecticut, right? Like, they, there's not a great, There actually is no, like, great local newsletter now. I know 6am cities probably going to come in and do this, but it's like an affluent town.

Brian, do not go in there, please.

I know, I know. Don't, don't screw me over. But it's, it's one of those things like, I always want to do. Like, selfishly, I think it would be kind of cool too because I look at like all the other people who do it and like, I feel like you get connected to the community more like, I don't know, I'm like, maybe I'll get some free, you know, some free meals out of this at restaurants, stuff like that. I just think it would be, it'd be kind of fun to do. So, yeah, it's. That's definitely something I think about. But I have, you know, I have ideas every day and this is an idea actually Louis and I talked about in our podcast, which, you know, I'll plug Letter Land podcasts as well. One of the, one of the things I talked about probably a few months ago was like, there's no major newsletter that I knew of in the prediction market space. So like Kalshi Poly Market so like who's, who's building the, the morning brew of, you know, Kalshi Poly Market, prediction markets. And I don't know exactly what that looks like, whether it's more of like a gambling newsletter where it tells you like what the best picks or if it gives you news on the events that are happening. So you have, you know, you're informed to make the decision. But I think there's like a huge opportunity there and like I've had to stop myself again from not doing that. I think there's. Yeah, those are kind of the. Sorry, drop my phone. There's, there's a couple of things there that I would love to do but you know, I'm kind of telling myself like, hey, I'm helping clients build their newsletters and like that's where my focus needs to be.

I just feel like go big or.

Go home was that. I know it's, it's not thinking very big of me, but I, the way I look at that right is you know, I'm, I'm building a big business there hopefully. And that's, you know, that's where I'm kind of putting all of my, my efforts and that business has grown. I just actually a couple of weeks ago brought on my first full time employee, have a couple of part time employees. So hoping to grow that business, you know, quite a bit in, in 2026 and like really scale it beyond just me kind of being the core expert where we can have a bunch of people that are helping build out in different verticals. Awesome.

Let's switch gears now and let's get more into like the content ops or the operations of running the newsletter and kind of how people can get more efficient and you know, what you recommend to your clients or things that you're following. Especially you're busy with all your clients and trying to expand that and then you still have to manage your own newsletter. So how do you structure your content? How often are you, are you. One week, Once a week guy, Daily guy. You know, what do you recommend to your clients? Like that, you know, are you curating stuff? What kind of insights can you give people on. On that?

Yeah. So I would say on the, on the growth side, just as far as like my, my recommendations and I think I like to look at it as like the water Coolest is kind of a client of leverage letter. Right. So I look at it as like we're managing another newsletter and maybe, maybe this was a leading question for you, but like to, I like to outsource you know, a lot of the, the growth stuff. So I always tell my clients, right, like everything I do is fo, like strictly, not strictly is mostly focused on content first, like organic content, right. So, you know, I focus a lot on making sure their newsletter is great. And then the growth stuff is mostly around organic type stuff, right? So whether that's, you know, social posts, like the pre and post call to action that everybody talks about, lead magnets, you know, thing things like that, other social posts on Twitter. And so what I like to do is like, there's a lot of great people out there who are killers at growing newsletters, right? Whether that's, you know, a paid ad agency, you know, what you guys are doing, you know, Sparkloop or like the Beehive Network. And so, you know, I kind of bring a, you know, an approach to, to my clients. And even the water coolest is like, okay, like let's do the basic blocking and tackling which is the organic growth. But that's never going to get you the scale. Like think bigger. And then I think it's kind of introducing, you know, myself, right, looking at myself as a client or my clients to, to the people in the industry who are doing really cool stuff that are, you know, able to grow newsletters. And the obvious one is like, you're always going to be able to grow on, you know, Facebook, right? Like that's probably like the first checkbox, like go use Facebook. But then I think it's like different things work for different types of newsletters, right? It's like, you know, like I wouldn't recommend, you know, the morning brew of, you know, Kalshi goes and tries to grow on LinkedIn, right. But it might make sense for them to work with you guys at that an audience at audience bridge on a handful, you know, using a bunch of your different products or you know, telling them to go try Sparkloop. Like Sparkloop might work, but they don't have success on the, on the Beehive, you know, network. So I think it's like finding for me it's, you know, finding the right partners kind of doing like all the basic blocking and tackling, which is like talk about your stuff on social media, that's probably not going to get you to scale. But then going out and partnering with the people who are experts at, at these things and you know, making sure that you're testing all of them out and really the numbers are going to tell you and you're going to get feedback from, from your audience that these are the, these are the right folks you want on your list to. To be growing and getting to the next level.

Are you actually writing the content for your clients or are you just going to coach them on how to get the first piece the greatest and then they go from there? I mean, obviously you help them along the way, but. Or you guys out, you know, are they outsourcing the content as well to you?

Yeah, so we, we kind of work on a, you know, it's like scales. You know, we kind of have a. We've taken like a weird approach because I think most people in the newsletter space, right, they're. They're like super laser focused on, you know, kind of growth or, you know, sales. Right. There's agencies and they're like, very specific of what they do. And what we found is like, again, there's. There's a lot of people who are just kind of like, I call them like newsletter curious. They're kind of like, oh, we want to build a newsletter, but like, generally we don't need know where to start. And so they're probably like, not going to come to, you know, audience bridge or go to like Astra, right, Because they don't have like, anything to sell yet or they don't have anything to grow yet. So the way I look at it is like, let me be their Sherpa to kind of help them build that newsletter in that core and then, you know, go hand them off to, you know, experts like you guys. And so I, to answer your question, we do kind of, we will do kind of everything. So we'll take it in house. And they say, like, hey, go run our newsletter. And we just want a, you know, a report once a month. Like, we've done that for clients, but it's usually somewhere in between where it's kind of like coaching. And they have, you know, their, their experts in house and like, you know, media team in house where they can write their own newsletters. And we're just going in and helping them audit it and saying like, hey, like, you should really think about this hook. Like, let's think about these sections, like, what are the dividers look like? And we can kind of do a full audit and all of that stuff. But yeah, it, it really ranges based on the client and kind of, I would say, their level of sophistication and how big their team is.

You're working with both B2B and B2C or you just focus on one vertical.

So I mean, I love B2B for a lot of reasons. Typically they, they have more money to spend. But yeah, we, we, we definitely work with, with both, I would say our, our core, we definitely lean more, more B2B. I've just kind of. And it's probably more so just because, like, I've carved out a bit of a niche there. Like, I started with a couple of B2B newsletters and then they kind of recommended me to other ones. And so we've gotten some, like, really good systems and we know what works there. So we've, we've leaned into it. But what I find is that a lot of the, you know, a lot of the same ideas work across B2B and B2C. And I actually probably take. It's probably better that my background is in B2C, because what I do is I find that like, B2B tends to be this super boring old, you know, and so, like, if you can take and like, layer the types of content on top of B2B content, like, you could just polish it a little bit and your, you know, your engagement is going to explode and people are super excited to read it and open it. And that's just because the bar is so low for B2B content. In most cases. It's like these boring white papers and like, I look at it the same re, you know, same way when I started the water coolest, it was like, you know, written by, you know, old dudes in, at the Wall Street Journal or Financial Times in really boring language. It's like, okay, well, let's just take, you know, the, you know, the, the farmers, you know, B2B guide, right, that's been written by the same dude for the trade association. And like, yeah, and like, let's make it exciting and people actually want to open it. And it's awesome because the advertisers are willing to pay a ton of money to reach that audience because it's super, super valuable to them. So, yeah, there's. There's just so much money sitting on the sidelines, you know, in, in B2B, you know, not just in newsletters, but media in general. Like, it just is in the midst of an overhaul. And I think right now, like, tech and AI are, you know, leading that in the B2B space. But hopefully it's going to kind of spread its tentacles to, you know, all the kind of boring, you know, industries.

Are there any tools you're using to help you write? Are you using an AI to help come up with stuff? Is it helping you write the content? Is this for ideation? Is it For, Yeah, editing.

It's funny. Right now I'm like pretty much raw dogging it. I'm just a. I would say, like I'm a content purist. Again, like, that's why I got into this thing is like, I just love getting into content, like sentence structure. Like, I could just nerd out about that all day. Like, I, I would love to not have to think about anything else but just write content. I'd be a good, you know, substack writer, but unfortunately I'd like to make more money than that. So, you know, I've kind of built this business, but like, that's, that's kind of my obsession. That said, it's actually an interesting time because I actually just brought on like an AI consultant which I didn't even know existed until, you know, like six months ago. And they're actually helping me build out more of a research tool. So it's not actually going to write the water coolest or any client work, at least for now on the client side, but the goal is like to basically do the things on either side of me writing. So, you know, it's going to be a tool that helps me go through and say, like, okay, you know, Tesla earnings, right? It's like goes and gathers a bunch of sources, like, what are the most interesting quotes about it? You know, did Elon say anything crazy on the earnings call, all that stuff. So it's going to kind of create the research for me. So when I go to write, it's not like I'm just like reading a couple of Wall Street Journal articles, CNBC article, and then coming up with something. And then on the other side, it's like once I write it, it's going to help me basically inject or you know, create some, what I like to call like Easter eggs or like these little like jokes or something that I've. I've implemented or used in the past, right? Because like I've been writing about Elon Musk for eight years. Like, I probably said a ton of hilarious stuff about him and made fun of him in a bunch of different ways, but I can only think of those things that like, if they just happen to come into my mind, right? So my idea is like, I have all this great content and it doesn't even need to be a joke, but like, it could just be like a reference or like a pop culture reference that I use. And it's like, why am I not reusing this stuff, right? Like, I have this huge library of content and you don't Even need, you know, eight years, like you could have a couple months of content library. And so basically, you know, after I do that, it's going to feed it through and be like, hey, have you thought about, you know, inserting this or referencing this or making light of this situation and just kind of looking back at like the stuff I've done in the past? So yeah, I think about it kind of in like two ways. Like the sandwich of like helping me research the piece, me writing the piece personally, and then kind of like helping feather in some of that stuff that, you know, kind of makes the water coolest, the water coolest list. And I think at the end of the day, like, it will always be be me and my voice and me writing it. But I could definitely see a future where, you know, this AI tool, you know, that, that is like a, a chat gbt, you know, custom GPT or something, you know, is helping me write client content where, you know, I'm, I'm doing something similar where it's like I'm taking their, their ideas or transcript I have with them. You know, it's helping me kind of write it, I'm going over it, or someone in my team is going over it, and then we're going through the editorial process.

Have you fed it all your content already and you're still working on it? Have you tested it or still.

So I'm actually, I'm waiting patiently. Probably by the time this, this podcast drops, I will be testing it. So I will, I will follow up with you on, on how it looks. So we're actually like doing all the feeding.

I, I, I feed mine all, all my stuff. So it helps me write my newsletters. I just tell it like we're going to give it all the information I want to talk about and then it'll boom. And I've given me at least my base structure and then I'll go ahead and edit and do things.

Are you, what are you using for it? Chat GPT?

I just use Chat GPT.

Yeah, nice.

Just to create a custom model person or whatever. If you put it on my articles, told them about me, my writing style, I import all these podcasts. I just keep on training it on all the stuff that I push out and then I use it for whatever as well as like client stuff, putting client information, client case studies, whatever we're doing. So it just keeps on learning. I'll even prompt it or I'll ask you, like, when the client has an issue, what have we done here before to help solve this or whatever, just output information. Like you see with how much writing you've done, you know, it should be able to write pretty damn close to, to the way you like to write. Just to like give it an idea and have it do that. And then you go and you fine tune it and you change whatever words you are or tweak it. But I could just see it. I mean, it's getting crazy out there.

So how, how close would you say you feel it gets to your final version? Like, is it 70%, 95%? Like where, where does, where's a lie for you?

I would say something that would normally have taken me like two hours, takes me like 30 minutes. So, you know, I already know in my head like what the base topic I'm going to talk about, what I'm going to write about. So, you know, I just write that out and that might take me five minutes to give it all the details and then it'll just boom and knows my format. Everything I want it was output in. And I'll go each section just making sure it's got what it needs to have. And then I'll. If there's sections that need, I think I need more information, I'll go add more information or I'll tell it to pull something. But I mean, it's just so much faster. I am by far a content truest. I can barely fucking write. You know, my grammar's horrible. I guess grammar's not even that big these days with the way people write newsletters. But you know, I got Grammarly always on updating my, my stuff, so I, I couldn't be able, I wouldn't be able to write a newsletter efficiently and, and continuously if I didn't have help of AI because it would just take too long and have a lot of other crap I have to deal with. Yes, yes, but I understand the whole content true as far. But I just feel like for people that are that good at content with AI, it could just be like another love.

Yeah, yeah. I mean that's the, that's, that's. Hopefully the goal is that it just kind of can take everything to the next level.

You said you're doing it just the aggregating of everything, so you have it there. So when we talk about, you know, how do you balance your, your voice with like professional or like true stuff? I mean, it's able to give you like now you have like six things that might come from a piece you're trying to write about that you can kind of plug in there as factoids or whatever or make fun of, you know, in a funny way, but where you might only got a chance of one or two because there's only so much you consume at one time.

Right.

So that'll, I'm sure gonna make it a lot better. You kind of talk about when I get into like growing your list, what's worked best? Kind of already went over it in the beginning. You did the influencers and did your Gmail scraping when you first started. Anything else you're. You're doing for or you recommend to your clients for list growth or are you trying, trying to focus more on like organic on Twitter? I mean, I guess on the LinkedIn would be probably the primary.

Yeah, I mean, I, I think the, the truth of matter is it's hard to grow a newsletter organically in, in 2025, right? Like, it's, there's a lot of noise out there. The social networks don't necessarily, you know, help you out. Like one of the, the interesting ways, probably one of the. And I haven't really done this for the water coolest. I've done it for some clients to varying degrees of success is using substack as a growth channel. And I know, you know, some people kind of swear by this and it's, you know, it works. But they have a, they obviously have a pretty good system and like algorithm. But I think, you know, the way I look at that is like it's just another social network, right? So like you're just basically growing on somebody else's channel. So I would kind of lump that in with social. But truthfully, like all I would say most of the water coolest growth right now, besides the people who just find out about it or you know, the handful of people who, you know, are sending it to their friends, almost all of it is coming from paid, you know, and that comes from working with you guys. I have Sparkloop turned on, you know, running, running Facebook ads pretty regularly. So, you know, most of that and, and quite frankly that just comes down to. It's a numbers game, right? It's like, you know, if you're, if you're losing a certain percentage of your list, there's just almost no way you're gonna make that up, you know, once your list is big enough. So I think after a certain level, like, yes, it's always good to be, be out there and have organic stuff turned on. But you know, if you want to get to any sort of scale in, in 2025, you know, unless you have some crazy, insane, you know, Unfair advantage. It's almost impossible, I would say, to be able to grow a list organically. And I actually say that knowing like a very huge celebrity's list, like has not grown super quickly organically despite, you know, his social posts and stuff like that. So like, I have some insight into the back end there. And so that's actually, you know, kind of reassures me that, you know, I don't know if it reassures me, but it tells me that it's like, it's not super easy for anyone to just like grow, grow a newsletter overnight, you know, like you like. I think a lot of people think they can.

Yeah. Yeah. I mean, you got, you said once you get to a certain size doesn't matter. There's never going to be enough organic growth to keep you to where you're at. If you want to keep scaling or keep it even, keep the same size. At some point you have to do paid marketing, right? Want to grow fast, you're paid. There's no, there's no options to it because of that. Do you have any? Since it's so bad at social networks and all the noise, do you have any tips of converting those people into followers, those followers into subscribers?

I mean, this isn't sound kind of cliche, like, I don't know, just provide, provide value for people on, on social, right? And I think, I think a lot of people use social as like, I don't know, they, they kind of get mixed up between like organic and just like advertising. So I think a lot of people just go on there and post call to actions, go sign up for my newsletter. But I mean, truly like the best way you're ever going to be able to do it is providing people a ton of value. And like the two ways that work really well right now are. Well, one of them works really well is kind of like the LinkedIn lead magnet, right, that you see every single person doing. It's like, you know, go, go comment, you know, TWC if you want to have my 10 latest stock picks, right? And like, and then so they automatically send it to you in your DMs. But you know, they, you sign up for their newsletter to get access to it. So I mean that, that works really well. That's why everybody's doing it. And then I would also say, like, it's not as good, but I've seen it work for some people recently and I think the algorithm is shifting a little bit, is on Twitter, you know, kind of like almost doing an auto post. Right. So I think Just posting stuff that's like, valuable or whatever you are, if you're funny on there, like doing whatever it is. And then there's a couple of tools out there, right, that'll like, auto post, so if it hits, you know, 20 likes or something, then it'll post a comment, you know, or reply to your tweet and say, like, by the way, I have this newsletter, you know, go sign up here. And so like, it's worth paying the $5 a month to have that tool just in case you, you know, you do kind of hit. Hit it big with a. A tweet. And especially if you're pretty active on Twitter, I've seen that work pretty well. And I think Nikita was talking about the, you know, Twitter is getting back to its roots of like, just go on and provide a ton of value, no matter how big of a, you know, how big of a following you have and you're going to get reach. And so I think there is, you know, real opportunity to go on there. But I would say, like, don't just focus on asking people to join your newsletter. Just like, provide a ton of value. And I see that in the B2B space, it's like, people are going to find out the other stuff you're doing if you're just constantly providing them value. And I know that kind of sucks and it's kind of boring, but it's a thing that works. And like, you know, in most newsletters, especially in B2B, it's like you'd rather have, you know, 10 people that truly trust you and like, actually want to read your newsletter than, you know, a hundred people that just kind of like randomly signed up and don't really give a shit. Uh, there's a couple I have to. I can, I can get in. We can drop in the link, but. Or in the bio. I'm blanking on it, but there's a couple of them out there.

Cool. Um, as you're growing your list the first time, and obviously what you're working on now, how did you manage or think about deliverability or list quality during that time so that, you know, it's easy to get a bunch of subscribers grow a list, but you can easily lose the livability and blow it up with a bunch of bad bills.

Yeah. So I think my thinking has shifted on this over times. I think when I was building the list, it was kind of like there were milestones and those were like. And this is going back before Apple kind of changed the game. Right? Because now you don't really know if an open is an open, but like going back to like 20, 19, 2020 right there. Only thing I cared about was like in, in all of this, right? It's only because it's what the advertisers care about. And like that was my business model. So you know, you would go to them and say, you know, you have a hundred thousand person list and I feel like the magic number was a hundred thousand and it used to open doors. Now a hundred thousand is like that's table stakes, right, for a consumer newsletter. And because it's so easy to grow and people are growing in sketchy ways, all this stuff. So I don't think you know, a hundred thousand matters all that much. Like truly, I think the, the big number for consumer newsletter is probably like a million subscribers or like 500,000 at least, right? Where it's like, okay, like now you're, you're a big boy. But I would say the, it was probably less important to me before about cleaning aggressively because people cared about how many people were on your list. Now I think I'm super insane about it, like super diligent about it and I do it all manually. Like I literally just have a time on my calendar and that's mostly because I don't trust ESPs and their automations and I've seen some things that are like, you know, people are getting killed out of my list. And then they're like, yeah, but they've, they've been opening, you know, in the past 60, 90 days. Like what's going on here? So I typically do it manually and I recommend that to a lot of people. I think it's like a, it's kind of like an eye opening experience to get like hands on with your list and be like, oh shit, like there's a lot of people who aren't opening like what, what am I doing wrong here? Right? It's just kind of like a, a bit of a look in the mirror. So I do that. But now I'm like, I'm super diligent about it and I think, you know, when I came on board with, with audience bridge, like I was super clear. I was like, I don't care about growing my list. Like I care about growing engagement and getting people who, you know, click on ads and you know, take action and reply to my newsletter. Because I truly think that's all that matters now if you're going to have an ad driven, you know, ad supported newsletter is, is what action people are taking, right? Like, and I Think a lot of people are going to try to say, well there's like engage, you know, or there's views and like opens and like all this stuff. Like at the end of the day advertisers don't care about that. Right. So if you're like, if you're building a consumer facing newsletter, the only thing that matters is the outcome for, you know, for, for advertisers or whoever your client is. And I'm not even saying like clicks like what it's going to come down to is like what's their, you know, their roas basically. So yeah, I just care about building the most engaged list possible. But I guess, you know, it's also fair to, to be fair, I also have like 100,000 plus people on my list, right. So like maybe I think there's like a fine balance. If you're like growing still and you're at 20,000, right? Like yeah, maybe you should be, you know, instead of killing people out who haven't opened in the past, you know, 60 days, you stretch up to 90 days so you can grow the list a little faster. So I think it's like a moving target. There's not ever like a perfect answer. You know, it's. I kind of look at it like, you know, when you're a VC backed company, right. Like it's kind of scale at all costs at some point and then you have to sit back and be like, okay, now we need to focus on profitability. I think that's the way I look at it, you know, kind of for, for newsletter growth. So there's no like one right answer. But you know, cleaning your list is very important in 2025.

Agree. And you talked about the engagement stuff. What's your subscriber reader like feedback loop look like as far as like they're, are they commenting, you replying to them? Are you using any of that stuff to help you produce your content for your next newsletter featuring any of the comments that you get know how are you using that, that feedback to help you improve the newsletter?

Yeah. So this is something I want to do more of and I recommend to my clients do more of. So I try to have at least a handful of touch points in my newsletter where people can either like reply, interact and like it's a very clear call to action to them. So like one of the things I've started doing, which I've had quite a bit of success with is because basically the, the referral program was not working whatsoever, right. So I was like, okay, you Know like referral programs are generally kind of dead unless you're doing something kind of one off or something really, really novel. So what I started doing was in the top of my email. I set up a new email address that's fwd the watercoolist.com and so I basically say every day in a. P.S. you know, love this newsletter. Forward it to someone who like X, Y, Z. And it typically has something to do with what's happening in the newsletter, right? So if I'm talking about EA Sports, it's like forward this to someone that will never beat you in Madden, right? Something like that. So it kind of has like this tie to like, it's almost like the, the memes or the gifts you want to send your friend sort of deal. Like that's, that's the idea that I'm trying to create. So basically it says forward this to your email, CC me in it and I'm gonna give you guys both something and I don't tell them what it is. And so I set up a different inbox and basically what I do is go in. If they've sent it and forward copied me, I'll go back. I have an EA that goes in and says, hey, do you guys live near each other? I'd love to buy you guys both your first round of drinks. When you meet up, you know, you guys should go grab a drink or a coffee on me. Like the, you know that's going to cost me, let's call it 20 bucks or something if I send it to them. But the amount of people who done that and either said like, don't send me the money, right? Like you don't need to Venmo me. Granted I have like a higher, you know, net income kind of audience and so they don't care or they're like, oh, we don't live near each other. But like, you know, I just wanted to share this anyways. Like the, it's probably less than a dollar per sub that I'm, you know, getting. It's not like a, it's not like a crazy high number of subs that I'm getting. But this is like one of my ways of like again like building that engagement with people. Like I'm trying to do something cool with them. I also asked them like, hey, if you guys do grab a drink, can you send me a picture of both of you guys so I can share it in the newsletter? And so again, it's just like these little, little engagement things. So like that's one of the touch points. I put a lot of questions. Every day I do a question that's actually become, like, one of my. One of the favorites in the newsletter. I used to do something that would be more so like, oh, do you think Tesla's going to beat earnings or miss, you know, earnings expectation? Like, that would always get, like, a couple hundred, you know, people answering it. And then I use beehives kind of built in, you know, collection so people can actually write comments on it. But then probably like, six months ago, I started doing these, like, ridiculous hypothetical questions because I got obsessed with, like, the Reddit Reddit hypothetical question. And so it'd be like, you know, would you rather get $500 a day or punch your mom in the face every day? Like, just these, like, really stupid things that I kind of equate to be, like, the things you would talk about at the bar. Just, like, kind of, like, jokingly, you're sitting around with your buddies talking. And probably, like, overnight, definitely overnight, the engagement, like, tripled on how many people were doing these. And I would get these big, long paragraphs of people explaining, you know, what they think about this stuff. Like, yesterday I did one of. It was like, a scenario of, like, when you should leave for the airport. So it was like, Your flight's at 11:30. You live a half hour away. You. You board at 10:40. What time would you leave? And people were writing, like, these huge, long things about, like, well, I want to get an airport beer, so I have to come in at, like, this time. And, like, I like to go to the lounge. So it's just little things like that. It was like this little switch. And it was like, the same mechanism, but it created so much more engagement. And now people, like, I actually launched a survey this week. Just, like, check in. I do one quarterly. And a lot of people are saying, you know, that's their favorite part of the newsletter, which I don't know if that's good or not, but it's. It's like one of those things where I was like, that's awesome that people are coming back every day because they want to get these random hypothetical. Like, I was on a. I was on a bachelor party a couple weeks ago. Two people asked me about the water coolest, and the first thing they brought up was like, where do you come up with the hypothetical questions? Right? So it's one of those things. And then I'm always just asking random questions throughout. Like, again, going back to. If I'm talking about Tesla earnings, it'll just be like, you know, what's the next crazy thing, you know, you think Elon's going to say? And it's like, just reply, you know, to this thread. And so I'm trying to get like, you know, three or four touch points in every newsletter where you can reply to me or talk to me. And again, that's like, I just want to build that relationship and I just want that engagement. It also helps with, you know, deliverability of people, you know, sending the right message to, to Google and aol.

And yes, that's really sweet. Way, way more strategic than I would do. But I'm gonna steal some of those ideas. We've been going on it for a while here, so just give you a couple more questions here and then we'll wrap it up. What's your thought on the competitive landscape newsletters right now? You know, everyone doing it. Then you know, you have self stacked, you got Beehive, you have ConvertKit, like making it like a mainstream thing. So you have tens of thousands. I mean I think I saw somewhere like one has like 60,000 users, another one 30,000 or 25,000. I know not everyone is probably using it, but there's a hundred thousand people writing newsletters. What, what gives? What's going to happen?

Yeah, I mean I think the good news is, and I actually just made a, I wrote about this on LinkedIn today. It was like, I think you just have to like give a damn about what you're writing about or like what you're creating. Because like you basically my, my philosophy is like if you're just starting a personal newsletter or something that's like a consumer facing newsletter, I would say you basically have to commit to like, I'm going to write this thing ever, you know, every week or you know, twice a week, once, once a day for like six months and expect literally nothing in return, right? Like there might not even be like people who, who want to read this thing. So my general philosophy and like, yeah, whatever, there's a million newsletters in this world, right? It's like, it's probably like that podcast stat that you, you hear, right? It's like only, you know, 2% of podcasts get past episode, you know, 10, right? Congratulations, by the way. I think you're past episode 10. And so I think it's the same way with newsletters. There's probably like so many dead newsletters or zombie newsletters out there that like people started over a weekend, you know, they were, they were like me and wanted to start their local newsletter and just Kind of gave up on it. So, uh, I think the where it all lands is a lot of people are just going to get kind of wiped out or just get tired of it because there's not enough money in it. And the more newsletters there is, right? It's like simple economics. There's a lot more supply of newsletters. So the CPM goes down and so it just becomes harder to actually make money off of a newsletter. And so I, I think at the end of the day it's like going to, going to kind of even out. And I think the exciting part for me and some other people that I talk to in the space is like the, the thing I love is like somebody who goes and builds like a 5000 person finance newsletter and they like work their ass off and they make a lot of great content and then they're like, this sucks, I don't want to do this anymore. And they want to sell it for, you know, a thousand bucks or something and I can come in and swoop that up or scoop that up. And so I think that's like really exciting for me or for people who are serious if you can build those relationships. And I know there's a couple of people out there who are doing it with, you know, varying degrees of success because it really depends on how people built their list. But I think that's actually like a really cool opportunity. So it's kind of weird to say, but yeah, there's gonna be like consolidation in the newsletter space. So either people are just gonna forget about it and those, you know, that's just gonna kind of go away or you know, in, in theory, some of those smaller newsletters are just going to get kind of gobbled up by the, by the big guys.

Yeah, no, I agree and I've already seen it. I've seen a lot of people getting, you know, list of 15,000, 5,000 great engagement. They just don't know that you want to monetize it. So I think this is a good one that we can end on. What's one thing newsletter operators get wrong when trying to be funny or edgy?

I think the, well, I guess there's a couple things I think the. It's probably using. What pisses me off the most is people using like ChatGPT dad humor. Right? Like if you go and ask ChatGPT to be funny, like it's not very good at getting like the nuance of humor. So I see that a lot. And then this is actually one of my biggest pet peeves in, in the world is all the newsletters who say they're like the entertaining version of xyz, right? So it's like, you know, like, even I don't think the morning brew leans into it anymore because I think they've, like, realize what they are. But like, they used to be like, oh, we're the irreverent and like, funny. I was like, not really. Right? It's like, yes, you are. You're less vanilla than the Wall Street Journal or cnbc. But, like, you're not. You're not funny. Like, I'm not laughing out loud. And I get. Maybe some people were. But I think the, the thing I hate the most is people who just are like, oh, I can just be the entertaining, you know, XYZ newsletter. And they use that as like the marketing tool. And then they don't deliver on that because they're not actually, like, funny or know how to be edgy in a newsletter. So I would say, like, just be honest about what you're going to deliver because you're going to make a lot of people angry. If they're expecting, like a hilarious newsletter about, you know, farmers in the Midwest and you just give them this, like, super boring, you know, newsletter, they're going to unsubscribe real quick. So I don't know if that answers your question, but yeah.

I'm gonna go get rid of my. My tagline on my newsletter.

Yeah, yeah, absolutely. Hilarious newsletter. Stop doing it, guys. Some of us out there are really trying to be funny.

That's funny. Where can people go to subscribe to your newsletters, learn more about you, reach out to you? If they wanna get some help with their newsletter, start a newsletter. I know I just sent someone your way the other day. Where, where can they reach out to you?

Sure. So the water coolest is just the watercoolist.com interested in working with me kind of on a consulting basis? Probably the best way is just email Tyler leverageletter co. And then I also have a podcast, which, Chris, I hope you'll. You'll come on and return the favor. It's called Letterland and I do that with Louis Nichols, who's the founder of Sparkloop. We do usually like twice a week, you know, just kind of talking about all the fun topics that, you know, come to our head about newsletters. And you can find that basically just search for Letterland anywhere. You get podcasts, YouTube, Spotify, all that stuff.

Awesome. We'll put that in the descriptions below so it's easy to find. Great chat. Look forward to talking again here soon.

Cool, man. I appreciate it. All right.

Hey, I hope you enjoyed that episode of Audience Bridge Insights. If you did, go ahead and do me a solid. Click the subscribe button right around here. You can also subscribe to the newsletter. I have a link down in the description below. Now, we have a lot of amazing guests lined up, but until then, keep sending smart.