Here’s the TL;DR but if you want ALL detail, scroll down a bit (don’t say I didn’t warn you… it’s long)…
I’ve been building newsletters for nearly a decade. Long before it was cool, scalable, or called a “content moat.”It started in 2014 with a WordPress blog no one read (EntryRevel.com). I was a finance major with a consulting job, a creative itch, and no outlet. So I wrote (this was before every 25-year-old male had a podcast). A lot. Mostly into the void. But buried in that failure were a few lessons that changed everything:
Email beats algorithms
Business news doesn’t need to sound like a textbook
Voice matters more than polish
Consistency compounds
Those lessons became The Water Coolest, which I launched in 2017 by emailing ~300 people I basically begged to subscribe.No master plan. No funding. No idea what I was doing.Just reps.Over the next few years, TWC grew into one of the largest finance newsletters on the internet by doing a few things well:
Writing business & markets like you’d explain it at happy hour or in your group chat
Finding unfair growth advantages early
Treating newsletters like products, not posts
In 2021, that work led to Barstool Sports acquiring The Water Coolest, where I became Head of Newsletter Operations & Finance Content.
Eventually, priorities shifted. I exited Barstool and negotiated the reacquisition of The Water Coolest as part of that exit.Full circle.After that, I had two options:1. Go work for someone else again2. Bet on what I actually know worksI chose door #2.Today, in addition to The Water Coolest, I run Leverage Letter, a newsletter agency built for serious operators, creators, and media brands who want to build must-read newsletters.We work with businesses that understand one thing: content over everything.If you care about:-- Building real audience leverage-- Turning newsletters into durable businesses-- Writing with an actual point of viewYou’re in the right place.Always happy to talk newsletters or see how I can help out. Shoot me an email at [email protected] or a text at 860-833-1240.
The WHOLE story…
I’ll spare you the part between conception and roughly age 25…It really all started when I bought the EntryRevel.com domain sometime in 2014.EntryRevel was a blog. One you almost certainly never heard of. The subject matter? Whatever the f*ck I felt like talking about a 25 year old dude working a corporate gig (so, working, dating, sports, etc.). Whether I’d admit it or not at the time, it was a Barstool/BroBible/Postgrad Problems ripoff… just worse.But mostly it was a cry for help (maybe a quarter life crisis?). My therapist has heard this story… Way back in 2006 when I was graduating high school, I told my parents I wanted to major in journalism or creative writing. They laughed and told me to pick a real major, like finance. So I did (to be fair, it was the right call). And, yes I took the safe, but unbearable corporate consulting job (then another and another). But there was always a creative itch I was looking to scratch.So I did what every red-blooded American male did circa 2013: started a WordPress blog (podcasts weren’t as popular yet, or I’d probably have gone that route).Over the 3 or so years where Entry Revel was active, I posted hundreds of blogs myself, which were read by literally hundreds of fans (thanks mom). And I let pretty much anyone with a pulse and a laptop publish to the site.Alas, internet fame and fortune didn’t come.So, how did Entry Revel become The Water Coolest?(Some brief context: The Water Coolest is a daily business and markets newsletter that reaches about 100k people. I started it back in 2017 and still own and operate it. Some people call it snarky, I like to say it’s my unfiltered thoughts.)Failure mostly.I’m not entirely sure when I knew it was time to wind down EntryRevel but it probably had something to do with the piss poor traction. I was quite literally yelling into a void for 3 years. Readership barely cracked 4-figures monthly and there was no path to revenue. Like none.But for all the failures, there were a few takeaways that would shape The Water Coolest:
I realized it was a lot easier to get people to read a blog if I emailed it to them vs. posting on social or figuring out SEO. Turns out, when I started sending emails with blog links, they started getting read.
By the year of our lord 2017 most of my blogs were about stories in the finance and business realm. I was reading the WSJ and Bloomberg every damn day for my day job. And with every 2k word story that could have been a Tweet, I wondered, why isn’t anyone writing about this stuff like I talk to my colleagues at happy hour or friends at the bar?
Around the same time I stumbled upon something on Twitter. Morning Brew. These two recent college grads were looking for writers to help them with this newsletter project that had ~100k subs.A brief stop at Morning Brew. Literally.I saw a post by the Brew on Twitter seeking a writer/editor. I filled out a Google Form and included links to my EntryRevel content.Apparently my deep dive on the inner workings of blacking out on the night before Thanksgiving showed my grasp of the English language. Because I was in their office (and by that I mean an NYU incubator) within a few weeks.After an interview and a full “work day” with them, they made me an offer to be employee 4 or 5 (can’t remember who was full-time or contractor at that point).And after weeks of back and forth… I turned it down. For a few reasons:
The money: I was working in consulting and living in NYC… and their offer was exactly what you’d expect from a fledgling media startup. And before you go all “bUt ThE eQUiTy!”... I’ve run the (rough) numbers and I likely would have walked away with $14 and Morning Brew referral mug (the old logo). Things turned out ok (more on that later).
I’m not sure we ever saw eye to eye on content direction. At the time Alex and Austin were very much on the education train. Their goal was to help train the next generation of business leaders. That meant content that felt a little too PG for what I had been doing and where I wanted to go.
After a lot of thought and countless conversations with people much smarter and wiser than me, I came to the realization: joining Morning Brew was giving up (even if EntryRevel didn’t have a future). Being part of the Brew was helping someone else realize their dream
So, I told Alex no… in the lobby of my consulting job. I remember to this day the absolutely brutal elevator ride back up that soul-sucking corporate hellscape where dreams go to die.Ok, so how did this all lead to The Water Coolest?It was a bit of a perfect storm…
I had begun to seen the power of email at Entry Revel
My blogs were increasingly focusing on business and finance news
The stint at the stint at the Brew (should I add that to my LinkedIn?) showed me the true power of newsletters
From that moment on I was heads down building The Water Coolest.And before you ask… NO there isn’t a cool story about The Water Coolest name. I actually think my college roommate, who wrote about sports on EntryRevel, had created a recurring series called “Water Cooler Sports.” Turns out WaterCooler.com wasn’t available… and the rest is history.The Water Coolest wasn’t a one-man. I assembled a crew from across the internet and my personal network.AJ came over from Entry Revel. He was an early ER guy who randomly reached out on Twitter about writing blogs. Fun fact: his sister designed the original logo (which hasn’t changed that much).Ian went to high school with my wife. He did a bit of everything (writing, marketing, ops) until he took over our ad sales. Today he runs one of the leading newsletter ad agencies (shoutout Ad Astra). I still work with them.Nate is Ian’s co-founder at Ad Astra. He joined TWC as a college intern and turned into an absolute killer sales guy.Nick was a writer who joined courtesy of Post Grad Problems. I’m pretty sure I found him because he was doing a weekly business news roundup for them. He’s a hilarious dude who is crushing in the standup world now.During the summer of 2017 we started shipping newsletters that didn’t go to anyone. Just getting our reps in (which is exactly the approach I’d take with a launch today).Launch day was September 12, 2017. Why September 12th, you ask? To be honest, it just seemed weird to start something on 9/11.And how many people did we send to? About 300… which included the EntryRevel list and whatever emails we could scrape together from our Gmail address books.As for goals? There weren’t any (just one of the many reasons the Morning Brew became Morning Brew and The Water Coolest… well, didn’t). At least not any that we memorialized. My only hope was to have more success than ER (not a very high bar…).Interestingly enough, if you look at that first edition of The Water Coolest… and today’s… it wouldn’t look THAT much different. Same logo (almost) and bare bones design. Although I do miss the “Water Cooler Talking Points” (we’d give you unhinged stuff to rattle around the water cooler or at happy hour).A walk down memory lane…2017 was of the growing pains variety. We hit a few thousand subs through brute force (mostly begging people and posting about it any chance we could). If this was a LinkedIn post, I’d probably call this phase “building our first 1k true fans,” but that would imply 1) I had a plan 2) I knew what I was doing. And, truth be told, I didn’t and I’m still not sure I do.2018 and 2019 was where things got interesting. We started to stack some little wins… admittedly by copy pasting most of what Morning Brew and theSkimm were doing. Pretty much everything worked to varying degrees because this sort of stuff was still pretty novel. Think: referral programs where we gave away koozies and stickers, paying college students to ask their entire class to subscribe, and cross promos with other newsletters. Bring me back.But the biggest unlock of that time period was finding out about fintwit and finance Instagram influencers. You probably know a lot of these accounts. They’re f*cking huge. Some have built massive media brands in their own right. Welp, I was talking to some of them when they had a few thousand (crazy engaged) subs and before they realized they were sitting on goldmines. I could pay these guys a few hundred bucks and get thousands of subs in return. The strategy was simple: a swipe up story (remember those?) with a dank meme. Rinse and repeat. Excuse me for being dramatic, but I truly believe that one growth hack/stroke of luck changed the trajectory of the company (and my life). It gave us some much needed momentum and put TWC on the map. I still tell people to this day that when building your newsletter you need to find your unfair advantage early on. That could be a growth hack, a cheap ad channel, or a crazy monetization opportunity. It’s not easy to identify but I truly believe in a wildly competitive landscape like newsletters it’s still one of the only ways to separate yourself from the pack.I should probably mention that by this point we had a real business… mostly because the economics of an ad supported newsletter were infinitely better in 2019. That meant I was able to take the leap and go full time on TWC. But before you applaud my bravery for taking the entrepreneurial jump, it was mostly because my day job was getting fed up with my performance (or lack thereof). I was spending every waking minute (yes, that included writing on my phone in the bathroom at work) on The Water Coolest. So yeah, it was more of a get your sh*t together or GTFO. I chose GTFO.Then 2020 and 2021 hit.Turns out COVID changed my life… for the better. Which still feels weird to say. You see, a bunch of things were set in motion…
Everyone was sitting on their couch watching Tiger King, waiting for their sourdough to bake… and trading stocks with money from the government (read: stimmy checks)
That led to the GameStop short squeeze and a boom in retail investing. I vividly remember explaining Wall Street Bets and a short squeeze to my son’s 70+ year old babysitter. This felt like the first time investing mattered to a whole new group of people.
Dave Portnoy (Barstool Sports founder) launched Davey Day Trader Global because sports ceased to exist and he needed to scratch his gambling itch
Large (Barstool) launched a show called Mind Your Business. His idea was to showcase how small businesses were handling lockdowns and the economic sh*tstorm - and give them some free publicity via the Barstool platform
My journey to Barstool began with a simple decision to apply to be on Mind Your Business. Until that point Large had mostly interviewed mom and pop shops. Think: pizza parlors pivoting to “make your own pizza” kits and distilleries slinging hand sanitizer to stay afloat.But, YOLO. I knew that Large had worked on Wall Street and loved finance, so it was worth a shot.Within a few days Large got back to me and scheduled time to record. I was, umm, green on camera. And I’m pretty sure I had just given myself a haircut (the pandemic was a weird time, you guys). The podcast was fine but the real magic happened later. Large posted a blog with the podcast and links to TWC. Overnight we gained a few thousand super engaged subs. One of those little lightbulbs went off in my head: I should be giving my money to Dave Portnoy instead of Mark Zuckerberg. So I emailed [email protected].Within a few hours I got an email from someone at Barstool asking if I could get on a call. This seemed weird considering I had marked the checkbox for “Less than $10k” in ad spend.As the conversation went on with the “ad sales guy” it became clear he wasn’t just an ad sales guy. He was asking the sort of questions an investor asks. He wanted to know about my growth metrics and financials. So, I looked him up while we were on the call. Welp, it was Stu Hollenshead, Barstool’s COO at the time.Turns out he was asking all these questions because Barstool (owned by Penn National at the time) was making a big push into finance content. See: Davey Day Trader’s wild success and endelss fintech and crypto ad dollars (see: zero interest rate phenomenon). To remind you just how big of a deal DDTG was, Dave got some love in the GameStop movie.From that moment (in February of 2021) on, I was negotiating with Barstool. I walked away from an initial low ball offer (negotiating 101 on their part), but by the summer things were getting hot and heavy. Finally in November of 2021 the deal closed. Barstool owned TWC and I became Head of Newsletter Operations and Finance Content at Barstool Sports.To answer your next question, no, I can’t share the details of the deal. But it was the largest amount of money that has ever been in my checking account at one time by many magnitudes.This was a full circle moment. Literally a dream come true. When I started out there were only two places I saw as a viable landing spot for TWC: 1) Barstool [a big gap] 2) StockTwits. Fun fact: in between offer 1 and 2 from Barstool, I got an offer from StockTwits.The Barstool YearsThe first question I get about Barstool is “what is Dave like?” The answer is simple: everyone in content, including Dave, is 100% the person you see across social, podcasts etc. In fact, when I sat down with Erika Nardini on day 1, there was really only one mandate: “Be yourself, we hired you to be you.” That was unequivocally true. I was never told what I could or couldn’t write. For f*ck’s sake, I didn’t even have an editor for TWC. The only “no” I ever got was related tohaving Martin Shkreli aka Pharma Bro on the podcast I launched with Large (shoutout Family Office fans). Which, fair.I learned an incredible amount at Barstool. As a reminder, my media experience to that point was me just sort of making it up as I went (reminder: I was a finance guy).
Large is the man. Anyone who knows him will agree. He changed my life.
Authenticity always wins: this is Barstool’s unofficial mission statement and they live and breathe it every single second.
Think big. Now think bigger. The stuff I pitched at Barstool that DIDN’T get laughed at is truly mind-boggling. For example: I once engaged Virgin Galactic about booking a flight to space for Large. My boss was totally cool with it.
I’m probably (read: definitely) better at newsletters than podcast. That said, go like and subscribe to the Letterland pod.
Now the part you’ve all been waiting for: why I left Barstool…Unfortunately, it probably isn't as salacious/sexu of a story as you might be hoping for. Perhaps you remember Dave famously repurchased Barstool from Penn for $1. Well, unfortunately for me, he didn’t see finance content (well, the finance content I was doing) or newsletters as the future of Barstool. Since those were the two things I spent my day working on, there were pretty limited options on the table.What I can say is that based on the structure of my contract, I was able to negotiate the reacquisition of The Water Coolest as part of my exit package. It certainly wasn’t how I envisioned it all going/ending but the experience set me up for the next chapter.Speaking of the next episode…After I rolled out of Barstool, pretty much everything was on the table for TWC. I considered selling it again (I actually got pretty close to a deal in 2024). But I kept coming back to one thing: I didn’t want to work for anyone again (as you’ll see, a recurring theme is not wanting to help someone else achieve their dream). I wanted to control my own destiny (that’s what ultimately led to sale #2 falling apart).Just one problem in the near term: making money.You see, any TWC ad relationship was Barstool’s. I didn’t have a sales team or a pipeline. And I had shut down the paid newsletter soon after joining the pirate ship.At the same time I was starting to get some inbound about running newsletters at some pretty interesting places. That, of course, wasn’t super interesting to me (see: controlling my own destiny). But, what I did realize is that there is massive demand for newsletter know-how.And that, ladies and gentleman, is how Leverage Letter was born (… and has since become a bigger business than TWC).(Here’s the part where I shamelessly plug Leverage Letter…)My thesis has long been that the only way to win in the newsletter game is to put content over everything. Turns out that’s only become more important in a world where AI slop is ruining the internet one em dash at a time. Which is why I am building an agency for serious newsletter businesses and creators. Our goal is simple (but certainly not easy): build must-read newsletters that reach the right people.If you want to learn more about Leverage Letter, you can check out leverageletter.co or just shoot me an email at [email protected] or a text at 860-833-1240.