On Aug. 27, 2003, @stoolpresidente and @barstoolsports released the company’s first newspaper issue.

Seventeen years later, Barstool is valued at $450M after Penn National acquired 36% for $163 million in cash/stock in '20.

A thread on the media, betting and comedy biz...

1/ In 2003, Dave Portnoy had a crummy sales job and wanted to start a free newspaper business.

A sum of money from his parents -- which would’ve been graduate school money -- helped him buy about a 100 newspaper racks and spread them throughout various Boston metro stations.

2/ He and a small group of writers, incl. current blogger @jerrythornton1, wrote for free, though they had other jobs.

Wrote about fantasy sports and gambling under fake names to make the operation seem bigger.

“It was supposed to be a gambling newspaper. Gambling and picks.”

3/ According to a local photographer, “The whole city [of Boston] knew what Barstool Sports was because of this newspaper.”

In a beat up Astro Van, Portnoy initially delivered the newspapers. Later, he started working with local models to hand them out.

4/ Though he remained confident in the early days, there were those people around Portnoy, like friend and ESPN analyst @McShay13 who thought differently.

Said McShay: “I legitimately thought he was going to go bankrupt. I was worried about him. He just kept grinding.”

5/ In the mid-2000s, Barstool started appearing on local Boston radio and diversifying revenue beyond ads, including selling t-shirts, staging events and parties and bringing their audience to Boston bars.

"If you could drive traffic to a bar, you could get money,” said Portnoy.

6/ Chicago native @BarstoolBigCat joined in 2008, becoming one of the company’s key figures.

Also, @devlinbarstool and @FeitsBarstool were among the early employees, both of whom still remain at the company.

In early 2010s, Barstool's biz stretched to hosting college parties.

7/ The 'Blackout Tour,' as it was called, gained notoriety in the northeast, for good/bad reasons. Hospitalizations, overdoses and debauchery led to their elimination.

Portnoy: “It was a party you did in your house, but it was in a professional venue. … It just had no rules.”

8/ Meanwhile, expansion continued, but Barstool still centered around a site.

@Kmarkobarstool and @KFCBarstool joined w/ launch of NY. Philly was a key market with @SmittyBarstool while @BarstoolNate headed up DMV. @BarstoolTrent, an Iowan, joined to cover more of the Midwest.

9/ In May ‘15, Portnoy and a group ft. @stoolsalesguy, @FeitsBarstool and @hen_ease all gained more publicity for the brand after the quartet was arrested at NFL headquarters.

The group handcuffed themselves together and held a sit-in as a Deflategate protest.

10/ In Jan. ‘16, Chernin Group invested <$20M to acquire 51% at $10M-$15M valuation. That came with a move to NY.

Meanwhile, ‘Saturdays are for the boys’ was also born in ‘16, thx to @FeitsBarstool. @PFTCommenter was hired in March that same year to team up w/ @BarstoolBigCat.

11/ Barstool hired digital media executive @EKANardini as its CEO in July ‘16.

At the time, Barstool had fewer than 15 people. Nardini, a Colby College alumna who previously spent time at AOL and Microsoft, among other orgs, beat out 74 male candidates for the top biz role.

12/ Nardini, already a fan of Barstool, walked into a company that had a history of racist, sexist and misogynistic behavior and content.

They’re issues that continue to plague the company to this day. Some in the media and even close friends questioned her move to the company.

13/ Her mandate was to bring structure and biz acumen to a company that never truly had a CEO as well as grow revenues, diversify the portfolio and broaden the brand.

In '17, distribution across digital/TV were key areas of experimentation while e-commerce also became a focus.

14/ Leading into the Super Bowl that year, the company’s regular ‘Rundown’ show aired live from Houston on Comedy Central.

Later that fall, Barstool and Facebook partnered around a live on-campus college football show, though both mutually agreed to part ways after 6 eps.

15/ In Oct. around that same time, Barstool partnered with ESPN for ‘Barstool Van Talk,’ an adaptation of the podcast Pardon My Take.

The show was cancelled after 1 episode when then President John Skipper said ESPN couldn’t distance itself from Barstool, its content and past.

16/ Both the Facebook and ESPN relationships were important learnings in Nardini’s early tenure. They, in part, showed what was possible on linear/digital with 3rd party orgs but also, reinforced a mindset and focus around creating owned IP that could be directly monetized.

17/ Under her leadership, in Nov. 2017, Barstool also acquired @RoughNRowdy, an amateur boxing contest started in the backwoods of West Virginia.

Months later in January, the company launched its own channel on SiriusXM, a deal that legitimized the company even more.

18/ In past 2 years, Barstool has reverted back to its gambling roots, hiring likes of @BWalkerSEC and @Marty_Mush. New podcasts, videos, franchises, original programming & out-of-the-box ideas -- like the creation of @CoachDuggs in '20 -- has been at the core of Barstool's DNA.

19/ Barstool’s currently at ~250 people. Its Sportsbook app will launch in Sept. Big name talent like @PatMcAfeeShow, @MichaelRapaport and @Jenna_Marbles, among others, have come and gone over the years. Yet, the core, to a large extent, has remained over the past decade-plus.

20/ Podcasts @CallHerDaddy, @PardonMyTake, @ChicksInTheOff, @SpittinChiclets and @ForePlayPod are among the most popular. Barstool’s added @alexandracooper and @GillieDaKid/@Wallo26 and recently @DeionSanders.

21/ At the time of Penn’s investment, its stock was <$30. Now, it’s >$55.

Said Chernin's @mkerns on firm’s Barstool investment: "We had a low end and a high end of what would happen. It’s already blown past every scenario of the high end. It’s a once in a lifetime investment."