I was scrolling through a friend’s bookshelf, looking for something light. She pulled out this bright orange cover with a cartoon Portnoy holding a giant stack of cash. I groaned. Honestly, I’m not a Barstool fan. I find the whole bro culture exhausting. But she said something that stuck with me: “Just read the first ten pages. He’s not who you think.”
So I sat on her couch, expecting to hate it. Ten pages turned into fifty. I kept waiting for the moment where he’d crack, where the armor would slip and I’d see the vulnerable businessman beneath. It never came. And that’s the thing that bothered me for days afterward. Is total refusal to apologize a form of strength? Or is it just a really good brand?
The Protagonist Who Refuses to Evolve
Dave Portnoy starts his story in 2004, printing a four-page broadsheet newspaper in Boston. He writes about sports the way people actually talk about sports at a bar. Crass, loud, full of inside jokes. The book tracks his rise from that single sheet to a nine-figure media empire with 300 employees.
Here’s what surprised me. Portnoy is genuinely good at telling his own story. The chapter where his first delivery van breaks down thirty feet from the dealership? That’s funny. The part where he hires homeless guys to distribute newspapers? That’s scrappy. And the Call Her Daddy drama with Sofia Franklyn and Alex Cooper? I’ll admit, I stayed up late for that chapter.
But the book has a strange problem. Portnoy never really changes. He doesn’t have a redemption arc. He doesn’t learn a lesson and become a better person. The whole point of the book seems to be: I was a loud, obnoxious jerk twenty years ago, and I’m still a loud, obnoxious jerk today. And you know what? It worked.
That’s the question the book forces you to sit with. What if the thing everyone tells you to fix about yourself is actually the engine of your success?
The Cage You Build by Never Apologizing
The core theme here isn’t business. It’s identity. Portnoy’s refusal to apologize or change has become his entire brand. He doesn’t just tell you he’s authentic. He makes authenticity the only move he has left.
I kept thinking about the Business Insider controversy. They published leaked videos of him using a racial slur and a crude joke about women. Most executives would hire a crisis PR team, write an apology, donate to a charity, and disappear for six months. Portnoy did none of that. He went on his own show, said “I’m not apologizing,” and challenged them to cancel him.
The imagery that stuck with me is from the early days. Portnoy talks about shoveling shit out of newspaper racks. Not metaphorically. Literal dog shit that people left in the racks. He had to clean it out with his own hands before stuffing in his papers. That image stayed with me. Because it’s not heroic. It’s embarrassing and stupid and real.
But here’s the uncomfortable truth. That same refusal to clean up his act, to smooth the edges, is what made the company worth nine figures. The very thing that makes him hateful to half the internet is the thing that makes him beloved to the other half.
What This Book Does and Doesn’t Do for You
I finished Cancel Me If You Can feeling unsettled. Not because it’s a bad book. It’s actually a compelling read if you’re curious about media entrepreneurship. Portnoy is funny in the way a loud friend at a bar is funny. He has good stories. The writing is raw and unpolished, which works for his voice.
But here’s the problem. The book never addresses the real question: what happens when “staying true to yourself” means hurting other people? Portnoy talks about his ex-wife Renee with genuine affection. He talks about the Barstool Fund, which raised millions for small businesses during COVID. He talks about buying the company back for one dollar to protect his employees. These are real, good things.
But he also talks about the people he’s burned, the bridges he torched, the public feuds he started. And he never once says, “Maybe I went too far.” There’s no introspection. Just momentum.
So who should read this book? If you’re a stoolie, you’ll love it. It’s like a long podcast episode with your favorite host. If you’re curious about how to build a media company from nothing, there’s real insight here. If you hate Dave Portnoy, you might find this book infuriating. But you might also find yourself grudgingly respecting his hustle.
Who should skip it? Anyone looking for vulnerability or growth. Anyone who needs their protagonists to have a moral arc. This book won’t give you that.
The real question Portnoy leaves you with isn’t about him at all. It’s about us. Why do we reward people who refuse to change? Why do we call it authenticity when a man says “I’m not sorry” and call it arrogance when anyone else says the same thing? I don’t have an answer. But I haven’t stopped thinking about it.
