The Water Coolest: Sold to Barstool at 100K Subscribers, Bought Back Two Years Later — the Full Round Trip

There are plenty of stories about people who sold a business. There are far fewer about people who bought back the business they sold. Tyler Morin, founder of the US financial newsletter The Water Coolest, grew the publication to 100,000 subscribers and sold it to Barstool Sports in 2021, then, roughly two years later in October 2023, bought it back and returned it to independent operation. Neither the sale price nor the buyback price was disclosed, but the round trip makes clear exactly what a personal publication that started from zero subscribers actually had as an asset.

Seven years, laid out

Neither the sale nor the buyback amount has been disclosed. However, in an interview with Newsletter Circle, Morin said the Barstool valuation was based on “a multiple of revenue.” Even for a free newsletter, the price was set not directly by subscriber count but by applying a multiple to the revenue that count generated.

What it published, and who made it

The Water Coolest is a free daily newsletter covering business and market news on weekdays. What sets it apart isn’t the information itself but the voice. Morin has said, “One of the weird/unique/great things about The Water Coolest is that it’s very much just my voice (love it or hate it).” He came from finance, not media. “I’m a finance guy, I didn’t know anything about media,” is how he’s described himself.

The team has stayed small throughout. Even at the time of sale, it was the founder plus several contractors, and it’s still essentially a solo operation today, ad-slot sales are outsourced to an agency, and Morin himself doesn’t handle that directly. Revenue comes from two sources: sponsorships and a paid subscription tier (deeper-dive content for paying members).

The first 90 days: “borrowing” distribution

Morin points to a single decision as the reason it grew. One made right at launch.

“One of the biggest things I did early on was partner with a ton of Instagram influencers.”

He partnered from launch with financial meme accounts and edgy finance-humor accounts. The Twitter equivalent would be something like GSElevator. “They were super helpful and helped spread the word about us,” he’s said. Paid ads on Facebook and Instagram, co-marketing campaigns with brands, co-registration deals, a college-ambassador program, and a referral program all followed later, but influencer partnerships came first.

This is the turning point. There are, broadly, two ways to build an audience from zero: wait for search or word of mouth to kick in, or place yourself where an audience already exists. The Water Coolest chose the latter (and placed itself in front of a group that nearly perfectly overlapped with its own voice: “people laughing at finance memes.” Rather than buying free ad space, it got recommended by outlets whose readership already matched) and that match is what drove people to actually open the emails.

The second turning point: narrowing the buyer to one company

Barstool, which had been expanding into finance since 2018, noticed that The Water Coolest’s voice and audience overlapped with its own, and reached out through McCarthy. McCarthy described Morin as having “a strange ability to make you smarter without putting you to sleep,” calling him “more provocative and more honest” than other financial newsletters.

Morin’s decision was clear-cut.

“Barstool was the only place I wanted to sell to.”

He wasn’t actively shopping the business around. He’s described the negotiation itself as “a crash course in negotiating.” What he paid the most attention to wasn’t the price, but editorial control. “I was scared of giving up editorial control. Luckily, at Barstool I had 100% autonomy.” After the sale he stayed on as Head of Newsletter Ops, keeping editorial decisions for The Water Coolest in his own hands.

Then in August 2023, Portnoy bought Barstool back from Penn, and layoffs followed. On October 4 of that year, Morin announced that “after about two years at Barstool, The Water Coolest is (once again) independent,” adding, “nothing changes.”

Why the buyback was possible — a structural read

This part is our editorial interpretation. The buyback was possible because of the asset structure underlying this business. The core assets of The Water Coolest were the subscriber list and Morin’s voice itself. The former can be transferred, the latter cannot. As long as the buyer keeps employing him, the publication functions, but if he leaves, it can’t be replicated. That asymmetry left leverage in the seller’s hands even after the sale, creating room to say “then I’ll take it back” once the parent company’s direction changed.

The flip side is that this also reflects a limit the business never escaped: attachment to one individual. Even with 100,000 readers, the team stayed essentially solo, ad sales were outsourced, and the means of scaling were limited. A revenue-multiple valuation means the buyer was pricing existing revenue, not subscriber count, and that revenue, in the end, was tied to one writer’s continued output.

What didn’t work, and what isn’t documented

As far as the sources confirm, paid ads (Facebook/Instagram) were used as a tactic, but what Morin cited as “one of the biggest things” was influencer partnerships, not paid advertising. Since the buyback, he’s also changed which metrics he tracks, favoring “other forms of engagement, like click-through rate or replies” over vanity metrics like subscriber count. Today’s 130,000 subscribers represent growth of roughly 30,000 over just over two years since the sale, a slower pace than the growth from launch to the sale.

Neither the sale price nor the buyback price has been disclosed, and neither has actual revenue, sponsorship rates, or paid-subscriber count. We won’t speculate here.

How much of this is reproducible

What’s readily reproducible is the distribution design used at launch: get placed in front of an existing outlet whose readership perfectly matches your own, like a finance newsletter placed in front of finance-meme accounts. When voice and interest overlap, the referral carries more persuasive weight. Rather than crafting creative to manufacture interest the way paid ads do, this structure delivers content to a group that’s already interested, via a source they already trust.

Another reproducible element: deciding, before the price, what condition matters most in a sale negotiation. For Morin, that was editorial control, securing 100% autonomy ended up being the foundation for the eventual buyback too.

At the same time, some conditions clearly aren’t reproducible. 2017 was before the newsletter market got genuinely crowded, and the fact that Barstool happened to be building out its finance coverage from 2018 was close to a coincidence on the buyer’s side. And above all, the valuation premise here, that the buyer saw value in “voice”, only holds when a writer’s individuality is genuinely distinctive. For a publication written in a more measured, generic tone, neither this sale nor this buyback would likely have happened.

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