The beginnings of media empires are seldom smooth. The Free Press began on Substack, when Bari and Nellie created an account using crappy airplane Wi-Fi. But after that, it was like we were News Corp. Just kidding: There was endless confusion about everything from incorporating (hello, Delaware!) to office kitchen-cleaning politics (ceramic coffee cups are a privilege, people!) to office leases on both coasts (thank you, Craigslist!).
Dave Portnoy knows all about what I’m talking about. He started Barstool Sports, the bro-tainment juggernaut that pumps out sports articles, gambling picks, podcasts, and fodder for internet drama at an industrial scale. People, especially young men, just can’t seem to get enough of Barstool and of Portnoy, a brash-talking Boston kid who, somehow, became the Rupert Murdoch of people who spend weekends shotgunning beer.
Below, in an exclusive excerpt from his upcoming memoir, “Cancel Me If You Can,” Portnoy lays out exactly what the beginning of Barstool Sports looked like: broken-down vans, drunk contractors, Hooters ads, and all. Portnoy was a recent Michigan grad (Go Blue!) with a deadening sales job and a hunch about what guys really wanted to read, and the gambling companies that might take an interest on the ad side.
There was chaos, but it worked, and Barstool grew and grew. Portnoy eventually sold a stake of his company, which netted him millions. But what didn’t change was his commitment to Barstool, then a print newspaper, having “the tone of a real sports fan.” From the first edition of the paper: “The people at Barstool Sports are a bunch of average Joes, who like most guys, love sports, gambling, golfing, and chasing short skirts.”
Read about Barstool’s humble beginnings from the man himself, below. And long live the bro. —Suzy Weiss
For as long as I can remember, I’ve wanted to work for myself. To try my own thing. The motivation was simple: I didn’t want to wake up every day and dread going to work. If I could have found a job that I enjoyed doing more than working for myself, it wouldn’t have mattered; in fact, Barstool Sports probably wouldn’t exist. But I couldn’t find that dream job.
It didn’t help that the only two things I liked were sports and gambling—not exactly the easiest fields to break into. By the time I was looking for jobs, after graduating from college in Michigan in 1999, I was essentially like every other white middle-class dude in the world with a liberal arts degree. I had no real skills. So I did what everybody else like me does: I took a sales job.
It was the height of the dot-com boom, the economy was firing on all cylinders, and any idiot could get a job selling anything. So I moved back to Boston, where I grew up, and landed at a technology research and consulting firm called Yankee Group. Every day I woke up and dragged myself to this job that I was good at but didn’t care about. I was making $80,000 a year, which seemed like an ungodly amount of money at the time. But I was bored out of my mind.
