Cancel Me If You Can Review: Unapologetic

Dave Portnoy's Cancel Me If You Can is a memoir that doesn't apologize for existing, much like Portnoy himself. This isn't a carefully curated corporate autobiography—it's a raw, conversational account of how a Boston kid turned a four-page sports broadsheet into a nine-figure media empire while becoming one of the internet's most polarizing figures. The real question isn't whether this book is worth reading; it's whether you can handle 300+ pages of unfiltered Portnoy without flinching.

Quick Verdict

Cancel Me If You Can delivers exactly what it promises: an honest, often hilarious account of Portnoy's rise from 2004 blogger to media mogul. The audiobook, narrated by Portnoy himself, is genuinely entertaining. However, the narrative meanders, personal details feel thin, and the title—admittedly awkward—suggests a different book than what you're getting. If you're a devoted Barstool Sports fan or someone fascinated by media empire-building, this is essential reading. If you're hoping for a polished business memoir or deep psychological portrait, you'll find gaps.

What This Book Actually Is

Portnoy frames Cancel Me If You Can as neither pure memoir nor business book, but rather "another bet on himself." That positioning matters. This isn't Shoe Dog by Phil Knight or Crushing It by Gary Vaynerchuk—those are strategic business manifestos designed to teach principles. Instead, Portnoy's memoir is a chronological ramble through his career, complete with tangents about pizza reviews, his rescue dog Miss Peaches, and feuds with internet personalities.

The book traces Barstool's evolution from 2004 Boston broadsheet to digital media powerhouse with over 300 employees and 150 active brands. Portnoy details the company's various near-death experiences, corporate partnerships (Chernin Group, Penn Entertainment), and the infamous Business Insider hit piece that nearly destroyed everything. He doesn't shy away from his failures—public divorces from his brand, the Call Her Daddy podcast drama, conflicts with employees like Nate—and frames each setback as a learning experience.

What makes this different from typical startup memoirs is Portnoy's refusal to sanitize his journey. He's not positioning himself as a visionary who always knew the path forward. Instead, he's a gambler who repeatedly bet on himself, lost spectacularly, and came back swinging.

The Audiobook Advantage

Readers consistently praise the audiobook version, narrated by Portnoy himself. There's a reason: his voice is his brand. Hearing Portnoy deliver his own story—complete with the Boston accent, the self-deprecating humor, and the conversational rhythm—transforms what might be a standard business memoir into something closer to a long podcast episode with a friend.

The written version, by contrast, captures that conversational tone on the page but sometimes feels clunky. Reviewers note the "chunky" writing style, where you can sense someone writing rather than speaking. For Portnoy's brand, this actually works—it feels authentic, like his blog posts. But it also means the prose occasionally lacks the polish you'd find in more traditionally edited memoirs.

What Works Brilliantly

Portnoy's honesty is the book's greatest strength. He doesn't paint himself as a hero or martyr. He acknowledges being "a mean, arrogant, petty and insufferable jackass" at times, yet he also highlights genuine moments of character: buying back Barstool for $1 to protect his employees, launching the Barstool Fund to save small businesses during COVID, and maintaining loyalty to his core team despite lucrative exit opportunities.

The behind-the-scenes details are genuinely compelling. Portnoy walks through the Business Insider takedown attempt, the various corporate partnerships that nearly swallowed Barstool's independence, and internal drama that shaped the company's culture. These aren't sanitized corporate anecdotes—they're messy, human, and often funny.

The book also succeeds in explaining why Barstool resonates with its audience. Portnoy understood something major media outlets missed: fans wanted "local, raw, and unapologetic" sports content in the same language and tone you'd hear at a bar, not the polished SportsCenter delivery. This insight—delivered in the early 2000s when digital media was still finding its voice—was genuinely revolutionary.

Where It Falls Short

The most legitimate criticism is structural. Cancel Me If You Can doesn't follow a clear narrative arc. It meanders through Portnoy's career in roughly chronological order, but jumps between different storylines without always connecting them. Readers who wanted a more focused business narrative or deeper exploration of his personal life will find themselves frustrated.

Portnoy's childhood and family background receive minimal attention. He mentions his immediate family in passing but doesn't explore how his upbringing shaped his risk-taking mentality or his relationship with his ex-wife Renee gets more coverage than his parents. For a memoir, this feels like a missed opportunity to understand the man behind the brand.

The title and cover art are objectively awkward—several reviewers mention embarrassment buying the book. The title feels clickbait-y in a way that doesn't match the book's actual content, which is less about "cancellation" and more about building an empire despite controversy. This mismatch suggests Portnoy may have pushed back against his editors' suggestions, which tracks with his brand but undermines the book's marketing.

Who Should Read This

Perfect for: Devoted Barstool Sports fans, media entrepreneurs interested in digital empire-building, people fascinated by internet culture, anyone who appreciates unfiltered storytelling, sports fans who value authenticity over polish.

Will likely hate it: Readers seeking polished business advice, people offended by Portnoy's brand of humor, those expecting deep psychological insight, anyone looking for a traditionally structured memoir with careful narrative arcs.

The middle ground: People curious about Portnoy but not deeply invested in Barstool will find this entertaining but occasionally indulgent. You'll get the story you came for, but you might wish for tighter editing and more personal depth.

The Bigger Picture

Cancel Me If You Can arrives during a fascinating moment in media criticism. The book's central argument—that Portnoy refuses to bend to "cancel culture" and maintains his brand authenticity regardless of controversy—feels almost quaint in 2024. The internet's appetite for outrage has evolved, and Portnoy's particular brand of brash Boston sports commentary is no longer shocking.

Yet the book succeeds in documenting how someone built genuine cultural relevance without following traditional media gatekeepers' rules. That's genuinely valuable, especially for aspiring digital media entrepreneurs.

Final Verdict

7.5/10 — An entertaining, honest account of media empire-building that delivers on personality but sacrifices narrative structure and personal depth.

Cancel Me If You Can is absolutely worth reading if you're interested in how digital media empires actually get built, or if you're already part of Portnoy's audience. The audiobook is the superior format—Portnoy's voice makes the rambling narrative feel like a conversation rather than a disorganized book.

But this isn't a masterclass in business strategy or a profound personal memoir. It's Portnoy doing what he does best: telling his story in his voice, unfiltered and unapologetic. Whether that's enough depends entirely on whether you find Dave Portnoy interesting. If you do, you'll devour this. If you don't, no amount of narrative polish will change your mind.