The history of the United States is one filled with founders — visionaries who created businesses, even whole industries, and helped this amazing country continue towards its goal of becoming a more perfect union. We’ve been so good at this that we’re almost victims of our own success. There are still innovators out there, but the world we’ve helped create is a different place. Coding AI into existence isn’t the same as scrapping and saving for years based on the improbable belief that one is building something durable. But before the complete technological overhaul of society and the dominance of a few mega corporations, there was still some room for idiot degenerates who were too cocky to understand that their analog ideas were idiotic and degenerate, particularly for a world that was going digital. This is the space that Dave Portnoy, El Presidente of “Barstool Sports,” worked to his benefit, taking a printed newspaper about sports, gambling, and Boston from a local publication that needed $3,400 a week to stay afloat to a multimillion-dollar enterprise. And now he’s written a book about his journey, at least his journey so far, for if there is one thing that founders rarely do, it’s retire. “Cancel Me If You Can” hit stores — or for those of us who pre-ordered from Amazon, doorsteps — June 30th. None of it is shocking. It’s not even particularly new information, especially if you’ve paid attention to Portnoy. It is a testament to the American spirit, though, and one that is welcome, given certain attitudes about the American dream in 2026. After college, Portnoy went into a white-collar sales job earning $80,000 a year, not exactly a shabby salary for a recent grad. He couldn’t stand the work, though, and after five years, he started Barstool Sports in 2003, a Boston newspaper he published twice per month. His sales experience helped him sell advertising space. His hustle helped him get it into people’s hands. His degeneracy pushed people to actually read it and look forward to the next edition, for he initially hired models to hand out copies before landing on the novel idea that sex sells. Thus, Barstool’s “Smokeshow of the Week” was born. Fun fact from the book: Portnoy coined the term “smokeshow.” He loved how the Miami Hurricanes entered the field through a cloud of smoke and imagined hot girls doing the same thing, ergo “smokeshow.” In terms of those early papers, they were just girls who consented to have their social media photos used on the cover. In terms of differentiating the paper from other things that crazy people handed out, having hot girls on the cover was a way to attract eyeballs. Dumb luck combined with hard work describes much of Portnoy’s ascent from fat guy living with his parents to multimillionaire media mogul. There was the fan who built and maintained barstoolsports.com for years, pushing Portnoy into the blogging space when blogging was in its infancy. There were writers who worked for free. Dan Katz, aka Big Kat, worked for peanuts for years. So did Kevin “KFC” Clancy. Both would become owners in the company when finance came calling, though it wasn’t pure magnanimity on Portnoy’s part. He was already making seven figures, and they wanted in on the action, considering their foundational roles. Given his brash and confrontational approach to social media and public fights, including with his employees, it would seem that he truly is a giant megalomaniacal narcissist who only cares about himself — and his current lady friends and rescue dogs — but the sections when he laments on those who should have gotten a stake in the company or how he should’ve made people wealthy earlier paint a different picture of El Pres. Sure, it’s his book, but his genuine concern for his people is evident in how he describes them. And he puts up with quite a lot, despite public excoriation. Without giving away details, because the book is worth a read, suffice it to say that the Barstool pirate ship operates exactly as one imagines it would; think Pirate King Archer, but with actual remuneration for the crew. He’s sold the ship twice and bought it back both times. He helped countless small businesses with the Barstool Fund during COVID, preventing them from going under. He had a line of frozen pizza, One Bite, that sold in Walmart, and he now admits was completely terrible. (For starters, it had Parmesan on it, and the R&D person who decided to put Parm on a Barstool pizza is a moron.) Now, he spends most of his time hanging out in his luxury estates in Florida and on Martha’s Vineyard with his dogs, Peaches and Pete. He’s still running the ship, though, making sure content keeps coming out and people get paid. There are always expansions into other areas and ideas, despite the fact that Portnoy is extremely polarizing, something I’ve avoided until this point. Because, yes, the book is titled “Cancel Me If You Can” for a reason. Business Insider, The New York Times, protestors, and randos have gone after Portnoy for his antics. He emerges from the fights victorious every time, mostly because he’s good at documenting events and preventing misinformation from overtaking the story. But also, it’s a fight for everyone around him, because if he goes down with the ship, so do they. That’s something he cannot let happen because, contra the Godfather, for El Presidente, business is personal and the nuts who work at Barstool aren’t just the crew, they’re his family. And Barstool is more than just a Boston paper now. It’s an enterprise, a way of life, a fundraising machine, a place where it’s basically impossible to get fired, even if you get blackout drunk and try to put cocaine in your eyes. And with “Cancel Me If You Can,” we get not just stories about how it came to be that way, but a look behind the hat and eyepatch and into the mind of the man named Dave who made being a degenerate gambler into an empire that makes the world a better place. Viva! *** Rich Cromwell is a writer living in Northwest Arkansas. He produces the Cookin’ Up a Story podcast, which you can listen to here. You can also follow him on X: @rcromwell4