Over the past 20 years, Barstool Sports has attracted a big audience of young men with its Bro culture edginess.

In 2017, along came The Water Coolest, a free daily newsletter with a similar edge but a different topic: money and investing.

By 2021, the two companies saw an opportunity to make a deal. But in an unexpected twist, by 2023, the founder bought the site back.

How voice played into The Water Coolest’s growth

Satirical in tone and shy of neither profanity nor controversy, Barstool has been described as  “the Bible of Bro culture.

The Water Coolest, founded in 2017, has a similar frat house-friendly voice, which founder Tyler Morin credits in large part for the newsletter’s success.

“One of the weird/unique/cool things about The Water Coolest is that it is very much my voice (love it or hate it),” Morin wrote earlier this year on LinkedIn, adding “staying true to my voice is probably why I ended up at Barstool.”

Readers responded to his light-hearted, boundary-pushing style. The newsletter went  to more than 50,000 subscribers by 2020, Morin told Simon Owens’s Media Newsletter. “I was a finance guy who knew nothing about media,” Morin told They Got Acquired. “I overcame it by making every mistake in the book.”

Savvy social media marketing also helped propel the bootstrapped business. “One of the biggest things we did was work with a lot of Instagram influencers right off the bat,” Morin explained in the newsletter. He noted that he reached out to several popular finance meme accounts when The Water Coolest was just starting.

“They were really great and helpful about getting the word out about us,” Morin said. “They were pretty cheap compared to what you’d be paying for Facebook and Instagram ads to reach the same number of subscribers.”

By the time he sold the newsletter in 2021, with just Morin and a few contractors working on the business, the newsletter had 100,000 subscribers.

How Barstool and The Water Coolest connected

Meanwhile, Barstool had hired a single writer, Michael McCarthy (known as “Large” on the site), to expand into the finance space in 2018. With its growing audience, similar tone and newsletter-focused business model, The Water Coolest grabbed the attention of McCarthy and Barstool, which was looking to increase its finance coverage, Benzinga reported.

“Tyler has the uncanny ability to make people smarter without putting them to sleep,” McCarthy said of Morin, calling The Water Coolest “more engaging and more honest than the others out there.”

Morin was also a fan of Barstool. Selling had crossed his mind, but he wasn’t serious about it, he told They Got Acquired. But the approach from Barstool made him think harder about a potential sale. “Barstool was the only place I wanted to sell to,” Morin said.

Morin first appeared in several pieces of Barstool video content with McCarthy. Then, in 2021, Barstool acquired the business for an undisclosed amount. No terms of the deal were made public, but Morin told us “it was a crash course in negotiation.”

A twist in the tale of The Water Coolest acquisition

After the sale, Morin stayed on at Barstool, where he continued working on The Water Coolest and contributing to the site’s finance offerings. “I was afraid to give up editorial control. Luckily with Barstool I had 100% autonomy,” Morin told us.

Then in August 2023, Barstool’s controversial founder, Dave Portnoy, bought the business back from then owner, Penn Entertainment, and laid off staff shortly after, the NY Post reported. He said taking the company private again would allow the business more freedom of expression free from regulatory scrutiny.

“For the first time in forever, we don’t have to watch what we say, how we talk, what we do,” Portnoy said. “It’s back to the pirate ship.”

That opened an opportunity for Morin and The Water Coolest. In October 2023, Morin struck a deal to buy his business back from Barstool for undisclosed terms. He announced the change on Twitter:

“After nearly two years at Barstool, The Water Coolest is going independent (again). And I’ll be in the driver’s seat, which means not a damn thing is going to change,” Morin wrote.