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👋 Talent is the new union — just like Dave Portnoy proved when his former Barstool employees walked away with $200 million in deals. While other media companies fight unionization, Portnoy's "athletic team" model turns departures into recruiting ads.

Read time: 4 minutes | 875 words

STORY 

🍺 Dave Portnoy: From Street Corner Hustler to Media Mogul

Dave Portnoy's empire started in 2003 as a four-page sports newspaper he literally handed out on Boston subway platforms. "I started a business from scratch and really didn't get any help, moved home, worked, didn't take a vacation day for 10 years and grinded my ass off," he later said.

What set Barstool apart wasn't sophisticated content—it was Portnoy's unfiltered voice that spoke directly to young male sports fans. By 2023, Penn Entertainment had bought Barstool for $388 million, but the real story isn't the money—it's the model.

The Anti-Union, Talent-First Philosophy

When media companies dealt with unionization, Portnoy took a radically different approach. "You know what our union is? Talent," he declared, rejecting traditional collective bargaining for something revolutionary.

"We use a model — I look at us like an athletic team. If you are a great player, and we sign you to a two-year contract, at the end, you'll have the option. You can go get more money, because we can't pay you, or you stay with us, and we pay you. But talent, for us, we're in a talent business. So, talent pays."

The Success Stories Prove It Works

The numbers speak for themselves:

• Alex Cooper: Left Barstool, made $70 million from Spotify

• Pat McAfee: Got $100 million at ESPN

• Bussin' with the Boys: Just signed $30 million over three years with FanDuel

What makes this revolutionary is how Portnoy treats departures. Unlike traditional media companies that view talent leaving as betrayal, Portnoy celebrates it as validation. "The Bussin' guys just got $30 million from FanDuel, that's more than we can do. So good luck, great relationship, I'm happy for them."

This creates a virtuous cycle: Barstool becomes a talent incubator where leaving with massive deals proves the system works. In a world where media companies struggle to retain talent, Portnoy built a system where letting talent go becomes proof of success—a model that turns traditional employment on its head and mints millionaires along the way.

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INSIGHT

🧠 The Farm Team: Why Smart Leaders Build People to Leave

Most business owners have it backwards. They hire talent and immediately start building walls to keep them trapped—golden handcuffs, non-competes, guilt trips about "loyalty." Dave Portnoy took the opposite approach: he built Barstool as a finishing school for media talent, knowing full well his best people would eventually graduate.

• The Psychology of Ambitious Talent: High performers don't want jobs—they want launching pads. When you position your company as a place where careers are made, not where careers go to die, you attract a completely different caliber of person.

• The Paradox of Retention: Here's what Portnoy figured out: the more openly you prepare people to leave, the harder they'll work while they're with you. When employees know you're actively helping them become more valuable—even to competitors—they'll give you their absolute best effort.

• Creating a Reputation Machine: Every successful graduate becomes a walking advertisement for your business. When Pat McAfee signs a $100 million deal with ESPN, he doesn't bash Barstool—he credits them for his success. That's worth more than any recruiting campaign you could buy.

• The Compound Effect: The farm team model creates exponential returns. Your first wave of successful alumni attracts even better talent in wave two. Soon, you're not competing on salary—you're competing on track record. "We've launched three millionaires in two years" is a much stronger pitch than "we offer competitive benefits."

The farm team mentality isn't about losing people—it's about building an ecosystem where everyone wins by helping everyone else win bigger.

ACTION

🎯 Action Steps for Real Businesses

Implement the "Farm Team" Mentality:

• Actively promote your people's personal brands — Gary Vaynerchuk at VaynerMedia encourages employees to build their own social media presence and speak at industry events on company time. Several have become recognized thought leaders, and when they eventually leave, they credit VaynerMedia for their development.

• Create "graduation ceremonies" for departing talent — When employees leave HubSpot for bigger roles, the company posts congratulatory LinkedIn announcements celebrating their "graduation." They treat departures like alumni success stories, which has helped them become known as a launching pad for marketing careers.

• Offer skills training beyond their current role — Salesforce famously trains customer service reps in data analysis and project management through their Trailhead platform, even though these skills make them qualified for higher-paying jobs elsewhere.

• Build an alumni network — McKinsey & Company maintains one of the most powerful alumni networks in business. Former consultants regularly refer new clients back to McKinsey and often hire the firm when they become executives elsewhere.

• Hire for potential over experience — Google's Associate Product Manager program specifically hires recent college graduates with no product experience but high potential. Many eventually leave for senior roles at startups, but they maintain loyalty to Google and often become partners or acquisition targets, creating a pipeline of future business relationships.

MEME

Dave’s most recent pizza review: