What are good book club discussion questions for Cancel Me If You Can?

Spoiler-free questions to get the conversation going: Grab a warm mug and settle in: what is a scrappy little project or side hustle you once poured your heart into, and how did it make you feel?; Before we dig in, share a moment in the book that made you smile, laugh, or feel a spark of I get that; The book is all about building something from almost nothing. Which part of that underdog journey warmed you or rooted you on the most, and why?; So much of the story is about loyalty to the people who showed up early. Who in your own life has been that kind of ride-or-die, and did the book bring them to mind?; When the author faces criticism or pushback, how did that land for you emotionally? Did it comfort you, unsettle you, or remind you of a time you were doubted?.

What food and drinks should I serve at a Cancel Me If You Can book club?

Food: Loaded stadium nachos, Slow-cooker buffalo chicken sliders, and Warm soft pretzels with beer-cheese dip. Drinks: Spiked hot cider, Local craft lager, and Warm spiced apple cider (non-alcoholic).

Cozy night

Cancel Me If You CanBook club questions, food & host guide

Dave Portnoy

A cozy book club night for Cancel Me If You Can by Dave Portnoy. Includes 8 spoiler-free discussion questions, food and drink pairings, a playlist, and a host guide, ready to print and share.

A relaxed club that loves real-life stories, strong personalities, and cozy debate over comfort food

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A candid, self-made founder's story of building Barstool Sports from a scrappy four-page newspaper into a digital media empire, told with unfiltered hustle and humor. It is an easy, conversational read that sparks warm talk about grit, loyalty, and chasing a dream.

Why it works for clubs

A rags-to-empire origin story that almost everyone has an opinion on
Big questions about ambition, criticism, and staying true to yourself
Plenty of personality, so quiet members find something to react to
Relatable themes of side hustles, risk, and betting on yourself

Themes & mood

hustle underdog media candid ambition

Reading level

Easy

Warm-up questions

1 Grab a warm mug and settle in: what is a scrappy little project or side hustle you once poured your heart into, and how did it make you feel?
2 Before we dig in, share a moment in the book that made you smile, laugh, or feel a spark of I get that.

Digging in

1 The book is all about building something from almost nothing. Which part of that underdog journey warmed you or rooted you on the most, and why?
2 So much of the story is about loyalty to the people who showed up early. Who in your own life has been that kind of ride-or-die, and did the book bring them to mind?
3 When the author faces criticism or pushback, how did that land for you emotionally? Did it comfort you, unsettle you, or remind you of a time you were doubted?
4 There is a real thread of stubborn belief in yourself here. When have you had to trust your gut even when it felt risky, and how did it feel reading someone else do the same?

Going deep

1 Without giving anything away, what did the arc of this story leave you feeling by the end, hopeful, tired, inspired, conflicted, and did it sit warmly with you?
2 Looking at the whole journey, what did this book gently teach you about ambition and the cost of chasing a dream, and would you pay that price?

On the table

Loaded stadium nachos

A nod to Barstool's sports-bar roots, warm and shareable for a low-pressure night

Slow-cooker buffalo chicken sliders

Homey game-day comfort food that feeds a crowd with easy, doable effort

Warm soft pretzels with beer-cheese dip

Cozy pub-style snacking that fits the scrappy, blue-collar hustle of the story

To sip

Spiked hot cider

A warm, indulgent mug that keeps the gathering relaxed and toasty

Local craft lager

An easygoing nod to the sports-bar spirit at the heart of the book

Warm spiced apple cider (non-alcoholic) No alcohol

A nurturing, comforting pour so everyone has a cozy mug in hand

Feel-good, hometown-underdog energy kept soft and warm in the background

Tap a track to play it. Full songs play when you're signed into Spotify.

You're invited

Cozy Night In: Cancel Me If You Can

Pull up a comfy chair for warm cider, loaded nachos, and easygoing talk about one wild underdog hustle. Come as you are, finished the book or not.

Trivia

1

What company did Dave Portnoy found?

Answer: Barstool Sports
2

In what U.S. city did Barstool Sports get its start?

Answer: Boston (the Boston area)
3

How did Barstool Sports originally begin, according to its origin story?

Answer: As a printed newspaper handed out for free
4

Roughly how many pages was that original Barstool print product?

Answer: Four pages
5

What nickname is Dave Portnoy widely known by?

Answer: El Presidente (or Davey Day Trader)
6

What broad industry did Barstool Sports grow into?

Answer: Digital media and sports/entertainment content
7

What food-focused review series is Portnoy famous for?

Answer: One Bite pizza reviews