The 2000s Blog That Keeps Finding New Monetization Models

In 2003, Dave Portnoy began handing out a free four-page newspaper called Barstool Sports outside subway stations in Boston. It covered gambling and fantasy sports and relied on an advertising model, with businesses paying for space while the paper remained free to readers. The website launched in 2007. In the two decades since, the company has been sold to an investment firm, acquired by a casino operator in two stages for more than half a billion dollars, and then sold back to Portnoy for $1. Across those ownership changes, Barstool continued to add new revenue streams.

The print origins shaped the business. Portnoy sold advertising against a defined audience of young men who bet on sports, and the website extended that model with wider reach and lower costs. By the early 2010s, Barstool had grown into a network of city-focused blogs built around individual writers and recurring personalities.

That structure became the durable asset. Traditional publishers build value around the publication. Barstool also built individual personalities with audiences that followed them across formats, then gave those personalities more ways to operate inside the company through podcasts, video shows, merchandise lines, live events, and sponsorships. Writers became podcasters, podcast audiences supported merchandise, and personality-driven audiences attracted sponsors. Barstool was effectively creating several smaller media brands within one company.

In January 2016, The Chernin Group acquired a 51% stake in Barstool. Portnoy announced the deal and set the total valuation at $10-$15 million.  The company moved to New York, and in July 2016 Chernin recruited Erika Nardini, previously chief marketing officer at AOL, as chief executive. She ran the company for the next 7.5 years.

Under Chernin, Barstool became a developed media business. Pardon My Take launched in March 2016, hosted by Dan Katz with PFT Commenter, and became one of the most downloaded sports podcasts in the country. Merchandise grew from novelty T-shirts into a core revenue line. The company acquired the amateur boxing promotion Rough N Rowdy in November 2016 and turned it into a pay-per-view events business. In January 2018, Chernin invested another $15 million at a valuation above $100 million.

The model carried reputational risk, though. ESPN launched a Barstool television show in October 2017 and canceled it after one episode when past misogynistic comments by Portnoy resurfaced. Advertisers periodically distanced themselves. Even so, Barstool’s audience continued to grow, helped by the fact that many readers and listeners followed specific personalities.

In January 2020, Penn National Gaming bought a 36% stake for $161 million, valuing Barstool at a reported $450 million. Recode reported 2019 revenue between $90 million and $100 million, earned primarily from podcasts, merchandise, and gambling content. Penn received the exclusive right to use the Barstool brand for its sports betting products for up to 40 years and rebranded its app as Barstool Sportsbook. The thesis was that Barstool's audience would download the app on the strength of the brand alone, sparing Penn the promotional spending that DraftKings and FanDuel deployed at enormous scale.

In February 2023, Penn acquired the remaining 64% for roughly $388 million, a transaction CNBC reported valued Barstool at $606 million. Penn's announcement cited audience growth of 194% since 2020, 1.6 billion podcast downloads, and more than 5 million units of merchandise sold.

Full ownership lasted just under six months. Barstool lost $16 million in the first half of 2023, per Sportico, and its history of controversies complicated Penn's gaming licenses across multiple states. On August 8, 2023, Penn announced a ten-year, $1.5 billion licensing deal with ESPN to rebrand its sportsbook as ESPN Bet. The same day, Penn sold 100% of Barstool back to Portnoy for $1. Penn recorded a pre-tax non-cash loss of $800 to $850 million on the disposal. Chief executive Jay Snowden told analysts that a publicly traded, highly regulated gaming company had proven an unnatural owner for Barstool.

In February 2024, Barstool signed a multiyear marketing deal with DraftKings, reportedly worth a low eight-figure amount annually. Within months of independence, gambling revenue was back.

Nardini, who now goes by Erika Ayers Badan, departed in January 2024, and Portnoy resumed direct control. In July 2025, Fox Sports announced a wide-ranging collaboration. Portnoy joined Big Noon Kickoff as a regular contributor, and Barstool now produces a live two-hour weekday studio show for FS1, giving the company sustained national television distribution for the first time. In December 2025, Netflix signed a multiyear deal, reportedly worth eight figures annually per Front Office Sports, for exclusive video rights to Pardon My Take, Spittin' Chiclets, and The Ryen Russillo Podcast.

Barstool no longer needs to own a sportsbook or build a television network to participate in those markets. It can create the personalities and programming, keep the underlying audience, and charge larger companies for distribution, sponsorship, and access. For media operators, the lesson is that audience ownership becomes more valuable when it can support several products at once. Barstool did not rely on a single format, platform, or advertiser category. It repeatedly turned the same personalities and audiences into podcasts, merchandise, sponsorships, events, betting partnerships, and television distribution. 

Barstool’s history shows how much leverage a media company can gain from a single committed audience. Advertising expanded into podcasts, merchandise, events, betting partnerships, and television, with each new format opening another revenue channel around the same audience.

For media operators, the lesson is to build beyond a single product. A loyal audience can support multiple businesses over time when the personalities, shows, and formats are strong enough to move across platforms. Barstool kept changing how it monetized without having to rebuild demand from scratch. See you next week.

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