Cancel Me If You Can Key Takeaways

by Dave Portnoy

5 Main Takeaways from Cancel Me If You Can

Launch before you're ready, then fix fast

Portnoy started with a logo that couldn't print and a distribution plan that failed immediately. Instead of waiting for perfection, he launched and corrected course—switching from homeless distributors to attractive models to solve pickup rates, then turning a failed shirt experiment into the core T-shirt business that kept Barstool alive for years.

Build a tribe that fights for you

Barstool’s fanbase—the Stoolies—became an unpaid army of reporters, defenders, and evangelists. From reporting on the Boston Marathon bombing faster than traditional media to rallying during Deflategate, Portnoy shows that transparent, sometimes controversial engagement creates loyalty that no marketing budget can buy.

Hire the obsessed, not the qualified

Portnoy hired people who were already doing the job for free—writers like Kevin, who turned his misery as a CDO auditor into killer content, and local bloggers who kept their own revenue. Credentials mattered less than consistency, volume, and a voice that resonated with the audience.

Speed and volume beat perfection every time

Twelve blogs a day, seven days a week was the baseline. Barstool outpaced traditional media by 30 minutes on breaking news, grew Twitter followers from 30K to 100K in one day, and sustained multiple massive audiences during COVID by sheer hustle. In a world of polished content, raw speed wins.

Never negotiate with those trying to cancel you

From protesters to corporate overseers, Portnoy’s consistent stance is to stand his ground. He refused to fire Mintzy over a sex tape because it would betray the brand’s identity, and he turned attacks from Business Insider and Deadspin into fuel for fan loyalty. Adversity breeds fierce loyalty—and paradoxically fuels growth.

Executive Analysis

These five takeaways form Portnoy’s central thesis: Barstool’s success came from defying conventional business wisdom at every turn. He launched raw, hired for passion over credentials, outran competitors with pure speed, and weaponized controversy to deepen fan loyalty. Each insight reinforces the others—imperfect launches build authentic tribes, speed attracts obsessive talent, and adversarial pressure forges unbreakable bonds. The book argues that in the modern attention economy, being untamed and unpredictable is a competitive advantage, not a liability.

This book matters because it offers a rare, unfiltered case study of a media entrepreneur who built a $450M company by breaking every rule. Unlike sanitized business memoirs, Portnoy shows the messy, sometimes ugly reality of growth—family fights, public feuds, and near-cancellations. It sits at the intersection of startup lore, media criticism, and pop-culture history. For readers, the practical impact is clear: stop waiting for permission, embrace the chaos, and bet on the people who care more than the ones who just look good on paper.

Chapter-by-Chapter Key Takeaways

The Beginning (Chapter 1)

Start before you’re ready: Portnoy launched with a logo that couldn’t print and a distribution plan that failed immediately, but he corrected course fast.
Understand human behavior: Switching from homeless distributors to attractive models solved the fundamental problem of getting people to pick up the paper.
Turn mistakes into revenue: The Ugly Shirts, born from a failed experiment, became a core business line that kept the company alive for years.
Grit over glamour: Behind every successful launch are dirty newsracks, late nights, and doing the jobs no one else will do.

Try this: Launch immediately with a minimal viable product, then obsessively fix each failure within days—your first version only needs to be good enough to start learning.

Internet 1.0 (Chapter 2)

Print was a trap: More readers meant more costs, not more profit—a fundamental scaling problem.
Blogging changed the rules: Speed and volume trumped depth; content became cheap to produce and distribute.
Early Barstool filled a void: Pre-Instagram/TikTok, it was the only place for user-generated, guys-at-a-bar-style videos and jokes.
The original crew had to leave: After years of unpaid passion, the website's arrival signaled a natural (and necessary) exit for those who couldn't commit full-time.
Success felt accidental: Growth came organically from sharing, not marketing—and the creator himself was surprised by it.

Try this: Swap complex marketing strategies for a single human-behavior hack: make your product easy to pick up, share, and talk about, just as Portnoy used attractive models to solve newspaper pickup.

The Lessons of the Newspaper (Chapter 3)

T-shirt revenue proved the business model could scale, but financial success brought messy personal conflicts (e.g., family fights over retirement savings).
Viral moments can come from unexpected places—Jenna’s makeup tutorial showed that video content could amplify Barstool’s reach far beyond written blogs.
Hiring for voice over résumé paid off: Kevin’s misery as a CDO auditor translated into relatable, fatalistic writing that resonated with readers.
Early growth meant making hard choices with limited resources—choosing between two talented candidates with only one salary to offer.

Try this: When hiring, prioritize a unique voice and demonstrated obsession over polished résumés—people who already do the work for free will outwork anyone who needs a salary to start.

Stoolapalooza (Chapter 4)

The tour validated that Barstool’s fanbase was real, passionate, and deeply connected to the brand.
Being transparent—even when it meant exposing conflict—built trust and loyalty with readers.
Sometimes saying yes to random people (like Dante) leads to the biggest breakthroughs.
The UNH SCOPE incident taught me that public accountability works better than private negotiation.
Stoolapalooza marked the moment Barstool stopped being a side hustle and became a permanent mission.

Try this: Plan one public, transparent event that proves your community is real—use it to create shared stories and inside jokes that bond your audience tighter than any ad campaign.

Finding Talent (Chapter 5)

Hire people who are already doing the job for free—consistency and volume matter more than credentials.
Pay was terrible, but the bet was on the future. Taking it personally when people hesitated reflected my own faith in the company.
The franchise model of city blogs worked: local writers kept local revenue, corporate kept national. It scaled naturally.
Controversy is inevitable when you push boundaries. The Howitzergate firestorm taught me that few will defend you, but those who do become lifelong allies.
If you miss a blog day, you better be in jail.

Try this: Recruit your most passionate unpaid contributors as formal employees, but keep the bar low for entry and high for output—miss one deadline and you're out.

The Blackout Tour (Chapter 6)

The Blackout Tour pivoted from dead-end college shows to a lucrative live-event franchise when a well-equipped Iowa bar + a viral video unlocked frat demand.
Live Nation paid $250,000 just to book Barstool at Bamboozle, revealing how out-of-touch big promoters were with the grassroots party market.
At peak, the tour generated nearly $200,000 per night in pure profit—fueling early retirement fantasies.
The Boston run, specifically the Northeastern show, triggered a media firestorm that permanently shaped Barstool's public reputation.

Try this: Pivot your live events toward the path of least resistance: when college shows flop, find a bar with the right equipment and let viral videos from students drive the next tour.

KO Barstool (Chapter 7)

Portnoy’s attempt to directly address protesters backfired when he was recognized, showing the limits of personal engagement in highly charged environments.
The “Angel of Barstool” embodies the unpredictable humanity that exists even within opposition—a protester who later helped Portnoy with pants and a ride home.
The second Blackout Tour was plagued by logistical failures, over-hyped media coverage, and under-prepared venues, all because of the original controversy.
Portnoy’s refusal to capitulate to protesters (“don’t negotiate with terrorists”) shaped his approach, but also escalated the operational difficulties.

Try this: When protests escalate, refuse to negotiate directly in public—instead, let the controversy play out on your own terms, and use the chaos to test your operations and team resilience.

Go Pres Go (Chapter 8)

Pace is a weapon. Twelve blogs a day, seven days a week was the baseline. Falling short meant getting crushed.
Pick your fights. Quitting the hot dog contest wasn’t weakness—it was clarity. Winning only matters if you care about the prize.
Culture is physical. The NFL combine wasn’t a gimmick; it was a test of who would commit fully to the team’s insane standards.
Attachment can be dangerous. Loving the company so much made every small failure feel existential, but it also fueled the drive that kept the fire burning.

Try this: Set an insane pace benchmark (like 12 blogs a day) and enforce it ruthlessly; then, when you need to slow down, pick only battles where winning actually matters to your long-term vision.

Boston Marathon Bombing (Chapter 9)

The bombing accelerated Barstool’s growth, with Portnoy’s Twitter following exploding from 30,000 to over 100,000 in one day.
The Stoolie community proved to be a powerful, decentralized reporting network, especially in high-density areas like Watertown.
Barstool’s willingness to publish unvetted information allowed it to consistently outpace traditional media by thirty minutes or more.
This event cemented Barstool’s role as a cultural force in Boston, blurring the lines between sports blog, entertainment, and breaking news.

Try this: Leverage your community as a decentralized reporting network by encouraging them to send raw, unverified tips—speed beats accuracy in breaking news, and you can correct later.

The Brady Four (Chapter 10)

Deflategate was perceived as a witch hunt against Tom Brady, and the sit-in was a direct, theatrical response from a media personality who didn’t seek conflict but would not ignore injustice.
The protest was meticulously staged—costumes, signs, press conferences—but the arrest and jail time were real and unglamorous.
The real win came after: the Patriots organization, though publicly silent, privately embraced the protest as a powerful act of solidarity.
Jail taught a lesson in patience and perspective. When you’re stripped of everything, the message you carried inside still matters.

Try this: Stage a theatrical protest that aligns with your audience's core beliefs, but be prepared to face real consequences—jail time or fines—because authenticity demands skin in the game.

Chernin’ and Burnin’ (Chapter 11)

Barstool was already profitable and successful before the Chernin investment—the idea that the deal “saved” the company is false.
The $7.5 million opening offer was embarrassingly low, but the final deal ($15M for 49%) came with the infrastructure needed for growth, even if I left money on the table.
Moving everyone to New York was a strategic necessity, not a betrayal of Boston—the skepticism faded once fans saw the results.
Erika Nardini’s instinct to defend the brand fiercely, including the “cashmere, bitch” retort, proved she was the right CEO to weather the constant controversies.

Try this: Before taking outside investment, ensure your company is already profitable—use the deal to buy infrastructure and talent, not survival, and negotiate hard even if it means leaving money on the table.

Mudgills (Chapter 12)

The "Big J News Cycle" is predictable: attack, defense, then the attacker playing victim.
Deadspin’s pivot from moral nihilism to moral crusade is seen as pure opportunism.
Fabricated stories, like the Sasha Goodfriend incident, still get printed without verification.
The High Noon renegotiation shows that standing your ground can lead to profitable partnerships.
Adversity breeds fierce loyalty—every attack makes Barstool’s fans fight harder, which paradoxically fuels growth.

Try this: When media attacks come, do not defend yourself in their terms—instead, expose their biases and let your fans fight for you; every attack that fails strengthens your brand's immunity.

Pardon My Take (Chapter 13)

PMT’s success created an identity crisis at Barstool, with fans who loved the show but hated the parent company.
Agent Michael Klein’s aggressive tactics deepened the divide between Portnoy and his own talent, especially Dan and PFT.
The Sam Ponder feud, born from a throwaway joke, escalated into a full-scale campaign that killed the ESPN deal.
A face-to-face confrontation with Ponder unexpectedly mended fences and earned Portnoy’s respect.
External conflict with a powerful media adversary ultimately brought Barstool’s fractured team closer together.

Try this: If your biggest hit creates internal identity conflict, let the talent own their success and separate from the parent brand when needed—external enemies will reunite you faster than any internal fix.

Grudgement Day (Chapter 14)

Grudgement Day is a cornerstone of Barstool lore, born from Dave's reckless period as "Club Dave" in 2016.
Stoolies' loyalty has a dark side: they demand access to personal lives, and Dave accepts that as the price of his success.
The Loud Sean basketball grudge match exemplified Barstool's chaotic, confrontational culture.
The JHammy breakup played out publicly when Dave discovered unexplained Uber charges, leading to an explosive on-air confrontation.
Dave's infamous quote about the "guy building a 100-million-dollar empire" proved prophetic, though he misjudged the final scale.

Try this: Accept that loyalty has a dark side: your most devoted fans will demand access to your personal life—set boundaries early, but know that transparency is the price of their devotion.

Building Superstars (Chapter 15)

Partnership models create alignment—and resentment. Splitting revenue 50/50 sounds fair, but perceived favoritism can poison trust even when the math is neutral.
Growth changes dynamics. As a company scales, the chaos that worked in the early days becomes a liability. People who thrived in the Wild West may sabotage structure instead of adapting.
Trust, once broken, rarely fully returns. Louis’s betrayal wasn’t just launching a side business—it was using proprietary code and turning a star against the company. That’s a bullet you can’t un-fire.
Stars can be saved by their own integrity. Pat’s willingness to disavow the stolen code and walk away cleanly preserved a relationship that outlasted the chaos. Character matters more than any contract.

Try this: When a partner steals proprietary assets, cut ties immediately but preserve relationships with those who show integrity—character matters more than any contract clause.

‘Call Her Daddy’s’ Daddy (Chapter 16)

Alex Cooper was a self-starter who learned editing on her own; her success was intentional and calculated.
Sofia Franklyn was essentially a tag-along; Portnoy’s primary relationship was always with Alex.
The duo’s demands escalated quickly—from office absenteeism to hiring Muj Fricke to demanding Barstool-level promotion.
Portnoy views the contract dispute as an attempted extortion: the threat of sexual harassment allegations was leverage to walk away with the IP.
The “I fuck” TikTok was a bizarre promotional accident that went viral and complicated the story.
Scooter Braun’s involvement signals that bigger forces were circling the show, adding a layer of industry intrigue.

Try this: If a talent threatens to walk with intellectual property, call their bluff publicly and prepare to burn the bridge—never hand over the golden goose to someone who tries to extort you.

The Art of the Deal (Chapter 17)

The Supreme Court’s 2018 sports-gambling ruling was the catalyst that transformed Barstool from a liability into a gold mine.
Penn’s $450M offer was structured as a long-term earnout with vesting stock—no instant payday, but a massive deferred payout tied to continued work.
Portnoy’s ability to empathize with Big Cat’s position and secure a bonus for him was the critical move that prevented the deal from collapsing.
The deal was not just financial victory but a personal vindication against every critic and enemy who had fought to destroy the brand.

Try this: When negotiating a multi-hundred-million-dollar exit, structure the deal to protect your key team members first—empathizing with their position can be the linchpin that keeps the whole deal alive.

The King of COVID (Chapter 18)

Spite can be a powerful HR tool: hiring Brandon Walker from MyBookie turned a viral tantrum into a long-term asset.
Disrupting finance isn’t just about money—it’s about making the old guard mad while letting regular people in on the game.
A bad product can still sell millions if the brand is strong enough, but integrity matters more than the launch numbers.
COVID-era content marathons proved that Portnoy could sustain multiple massive audiences simultaneously with sheer hustle.
The BFF fund showed that even a provocateur can pivot to genuine philanthropy and actually move the needle for real people.

Try this: Use spite as a hiring tool: convert a viral tantrum into a full-time employee whose passion proves they care more about your mission than any polished candidate ever could.

Politics (Chapter 19)

Portnoy’s 2016 Trump support was about disruption, not ideology—he wanted to break the system, not endorse specific policies.
The Trump interview revealed a rare moment of vulnerability from a candidate who usually never admits mistakes.
Political polarization has made all-or-nothing judgments the norm; any association with Trump defines you completely, regardless of your actual record.
Portnoy sees himself as an outlier who hates extremism on both sides, but acknowledges that his Trump interview locked him into a public identity he can’t escape.

Try this: Separate your personal political identity from your brand's commercial needs—support causes disruptively, not ideologically, and be ready to live with the permanent labels that follow.

Business Insider (Chapter 20)

Portnoy believes the Business Insider article was a calculated attack driven by Sofia Franklyn and the producer Muj, both of whom had personal vendettas.
The article’s star witness was Muj’s girlfriend, who later became an OnlyFans performer and admitted to pathological lying—facts Portnoy uses to discredit the story.
Mina Kimes’s rapid retweeting of the articles without engaging with his defense intensifies Portnoy’s anger; he confronts her personally but ultimately holds back the video.
Portnoy openly embraces his vindictive, confrontational nature as a core part of his identity, rejecting any notion that he should have acted more diplomatically.

Try this: When hit with a personal attack article, gather every piece of contradictory evidence and consider releasing a full rebuttal—but sometimes holding back the most damaging video preserves your strategic leverage.

Under New Management (Chapter 21)

The sex tape and the N-word incident were separate but cumulative crises—each tested Penn’s tolerance for Barstool’s “anything goes” culture.
Portnoy refused to fire Mintzy, arguing that doing so would betray the company’s core identity and the loyalty he owed his employees.
The ESPN offer forced a reckoning: Portnoy could either leave quietly or fight to keep Barstool intact. He chose to fight, knowing most of his staff would lose their jobs otherwise.
This chapter marks a turning point where Portnoy realized Barstool and corporate oversight were fundamentally incompatible.

Try this: Refuse to fire loyal employees for corporate-mandated 'culture cleanses' even if it means exiting a lucrative partnership—your brand's identity is worth more than any single deal.

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