Cancel Me If You Can

Both trace how a relentlessly difficult founder turned a scrappy idea into a cultural juggernaut — and made powerful enemies along the way.

If you liked Cancel Me If You Can by Dave Portnoy and want another book about a polarizing, hard-charging founder who built something massive from nothing, Steve Jobs by Walter Isaacson is the obvious next read. Both books pull back the curtain on the obsessive drive, messy relationships, and public controversies that come with building a company that reshapes an entire industry. Isaacson draws on hundreds of interviews to show Jobs at his most brilliant and his most brutal — a portrait that will feel familiar to anyone who followed Portnoy's own rise from Boston street corners to national media dominance. Readers searching for books like Cancel Me If You Can will find the same tension here: a visionary who refuses to apologize for who he is, even as institutions and rivals try to take him down.

A deep dive into how one ambitious outsider seized power, rewrote the rules, and became too big for his enemies to cancel.

Readers who finished Cancel Me If You Can by Dave Portnoy and were drawn to the theme of an outsider accumulating power faster than the establishment can contain him will find a rich parallel in Robert A. Caro's The Power Broker. Moses built an empire across New York City not with elected office but with relentless maneuvering, media savvy, and a willingness to bulldoze anyone in his path — literally and figuratively. Like Portnoy, Moses attracted fierce enemies who tried repeatedly to dismantle what he'd built, and like Barstool Sports, his legacy remains genuinely controversial. This is the book to reach for if you want to understand what Cancel Me If You Can looks like on a generational timescale. Anyone searching for what to read after Cancel Me If You Can will find Caro's epic both challenging and deeply rewarding.

A rock-star-voice memoir about building a legendary brand through chaos, excess, and sheer refusal to conform — told without a filter.

If you liked Cancel Me If You Can by Dave Portnoy because of its raw, unfiltered voice and its account of someone who built a loyal following by being unapologetically himself, Steven Tyler's memoir delivers the same energy. Tyler traces Aerosmith's rise from broke Boston-area kids to one of the biggest rock bands in history — navigating addiction, band implosions, industry politics, and a media that kept writing them off. The Boston connection alone is a nice bonus for Barstool faithful, but the real overlap is tonal: both Tyler and Portnoy write like they talk, with humor, bravado, and zero interest in softening the rough edges. Readers searching for books like Cancel Me If You Can by Dave Portnoy who want that same loud, candid energy will feel right at home here.

A memoir about refusing to shrink for public approval — different audience, same core defiance of what you're 'supposed' to be.

Cancel Me If You Can by Dave Portnoy and Untamed by Glennon Doyle don't share a demographic on the surface, but they share the same spine: a writer who decided to stop performing the version of themselves that other people found acceptable and paid a public price for it. Where Portnoy fights cancel culture from the right flank of media, Doyle navigates judgment from family, religion, and social expectation. Both books became massive bestsellers because readers — regardless of politics — recognize that specific hunger to see someone refuse to be reshaped by outside pressure. For readers who want to broaden their 'if you liked Cancel Me If You Can' list beyond sports and media, Untamed offers a genuinely different story told with the same stubborn refusal to apologize.