🍺🗞Barstool Sports

How Barstool Sports survived its first four years as a free newspaper to serve its thousands of early adopters in Boston?

They go by many names

Whether you know Barstool from their infamous "Call Her Daddy" Podcast, the day trading sessions with their outspoken founder Dave Portnoy @Elpresidente on Twitter or their news website, they are a force to be reckoned with in Media. In a "dying" industry, Dave has managed to found a media empire in 2003 that has netted him over $100m. Something he loves to remind us of every other Tuesday.

How it all started

Dave loved Gambling, but the gambling industry wasn't too fond of him. He couldn't land a marketing gig at an offshore Casino. Instead, he tried to salvage the interview by pitching his gambling newspaper idea and got some positive perception from the Casino. If he were to build a newspaper focusing on gambling and fantasy football, he could land some big $$ from offshore sportsbooks companies.💡

How to get started with 0$

Well, almost 0$. Dave squeezed a few Gs from his mom and pop to get started. It's not your typical 5m pre-product pre-seed dev tool round but still worth mentioning. That was enough to buy him around 100 news racks and place them outside the T train station all across the Boston Metropolitan Area. After deploying all the money he had on news racks and a really really really old van to drive around to deliver the paper, he still needed staff to write, edit, and publish the issues. That's where your friends, friends of friends, girlfriend, and parents come in. Here is a (non-comprehensive) list of Barstool employees during the first two-three years (None of them was getting paid btw)


  • Erin Boyce (Friend of Friend). Published the newspaper. A veteran of the industry


Each writer wrote under three names, at least, to make the paper seems much more significant than it was.

  • Jamie Chisholm (Friend ) 

  • Jerry Thorton (Friend)

  • Pete Manzo(Friend)

  • Dave Portnoy (Founder)

Sales - Events (more on that later)

  • Paul Gluczynksi (friend of his girlfriend)


  • Eric Levin (Cold outreach to Dave to do free work to break into the industry)


  • Mom & Dad. Used to manage all the parking fines he got and made sure they were paid on time.

Turning your cost centers into revenue streams

Giving people, on early train commutes, a free sports and gambling newspaper may seem easy to do. Who doesn't want free stuff? Answer: More people than you think. In the beginning, Dave hired a company (Labour Ready) that would help the less fortunate land a blue-collar job, in that case distributing the paper. When didn't work out, Dave Portnoy pulled the most Dave Portnoy move: he hired a modeling agency to use models to distribute his paper instead.

This was a lot more expensive, and given that the ad business had yet to pick up, Dave needed a way to pay for it. So used that immense burden and turned it into a cash-generating machine.

  • Dave would pay the models to distribute his paper which put the paper into the hands of orders of magnitude more people

  • Eric- the photographer- suggested turning the homepage into a full-blown ad featuring one model every issue. Every burgeoning model wants to be on a cover. Even if its Barstool.

  • He pitched his access to "pretty girls" and "hardcore fans" (thanks to Eric 😉) to bars and started sponsoring parties. A shit load of them

  • More parties. More fans. More Models. More Issues Distributed. Bigger Parties, and so on. 

Getting the sweet dollars

Things don't always go according to plan. Barstool started as a fantasy football/sports newspaper and today is probably best known for a top-grossing sex podcast. That has always been the case. For the lifetime of the paper (pre-Website), advertisers never "knock(ed) on the door," asking to sponsor their content. So Dave and the team had to get a little bit creative in making money early on. Here is what they did

  • Look a lot bigger than you are.

Barstool would stick the logos of different local restaurants, bars..etc. All over the newspaper as if they were paid ads. They would then make sure a few issues would land in the hands of the competitors, call them up, and create a lot of FOMO. 

  • Merch..Merch...Merch

They had a special section in the newspaper for the number of "Ugly T-shirts" sold that was updated every week. While merchandise of sale for a media company is table-stakes now, back in 2003, it was novel. and FOMO.

  • Monetize your community

Dave said in an interview, "If you can drive enough people to a bar, you can make money out that." When ads weren't just making it for the company, Dave went all-in on events. Because he has built a loyal readership in Boston, all he had to do was get them all in one place, and then there are tons of ways to make money off of them. Revenue share with the bar, selling merchandise, partnership with beer and liquor companies..etc...etc

The Barstool we know today is very different than the newspaper back in the day. It took sheer will and various shots on goal to get to where it is today. Dave when describing the company back in the newspaper days had one thing to say

It Sucked! It really did!!

This is the story of how Barstool managed to survive its first four years as a free newspaper to serve its thousands of early adopters in Boston.

See you next Saturday 😉,