Cooper Flagg Inc.
How the next generation of superstars will build billion-dollar brands through equity, global expansion, and direct fan engagement.
Right now, Cooper Flagg is the most talked-about young basketball player in the country. The Maine native is a projected No. 1 NBA Draft pick, an elite prospect with the potential to be the face of the league for the next generation. But in today’s sports world, the most successful athletes are also brands, investors, and media moguls.
For Cooper, his professional career isn’t just basketball—it’s how he thinks about himself as a business over the next 15 years. The modern player economy has evolved beyond endorsements and sneaker deals. Today’s stars are equity holders, entrepreneurs, and digital-first brands. The question is: How will Cooper Flagg navigate this new era, and what lessons can he take from the athletes who’ve come before him?
The New Playbook for Superstar Athletes
The biggest difference between this generation of players and past superstars is that the business of being an athlete now starts early. NIL (Name, Image, and Likeness) deals have already made Cooper one of the most marketable young athletes in the country. Before he plays a minute in the NBA, he’ll have millions in off-court earnings.
But the real opportunity lies in how he scales that over time—because the best athletes aren’t just signing endorsement deals, they’re building multi-billion-dollar enterprises.
1. The Shift to Equity and Ownership
Yesterday’s model: sign a sneaker deal, collect endorsement checks, invest in nothing until retirement.
Today’s model: own everything you can.
Michael Jordan’s initial $500K Nike deal turned into a $1B+ empire because he negotiated a percentage of sales, not just a flat endorsement fee.
Magic Johnson built one of the most successful post-playing business careers, turning early stakes in Starbucks, movie theaters, and real estate into a $1.2B portfolio, while also becoming a major sports team owner, including stakes in the Los Angeles Dodgers, LA Sparks, and Washington Commanders.
LeBron James has amassed a $1.2B fortune, launching SpringHill Company and taking equity in companies like Blaze Pizza, Beats by Dre, and Fenway Sports Group.
Serena Williams has built one of the most successful athlete-backed venture funds, investing in 60+ startups, including 14 unicorns (companies valued at over $1B).
The lesson? Equity matters. When Cooper signs his first major deals, he should be negotiating for ownership, revenue shares, and long-term upside, not just up-front cash.
2. The Business of Fandom: Building a Direct Relationship with Fans
In the past, players needed TV networks, sneaker companies, and leagues to control their image. Now? Athletes control their own distribution.
Cristiano Ronaldo earns $2.4M per Instagram post, making social media a revenue stream in itself—but more importantly, it enhances his leverage in brand deals.
NIL has changed the rules for young stars, letting them monetize their brand before they ever sign a pro contract. Olivia Dunne turned her gymnastics career into a $3M+ annual NIL business, while Angel Reese capitalized on her March Madness stardom to become one of the most marketable college athletes ever, seamlessly transitioning her NIL empire into professional opportunities. These athletes have proven that a strong personal brand built in college translates into long-term business success.
Engagement matters as much as followers—brands now prioritize high-engagement athletes over those with just big numbers, recognizing that deep fan connection drives real value.
For Cooper, this means treating social media as a business from Day 1. His audience will be his biggest asset—driving sponsorship value, direct-to-consumer opportunities, and lifetime fandom.
The smartest players think like content creators, offering fans behind-the-scenes access, training insights, and real-time interaction. The more authentic the connection, the bigger the business upside.
3. The Globalization of Sports = Bigger Business
The modern sports industry is no longer confined by national borders—athletes in every major sport are leveraging global markets to expand their brands and business empires. Soccer stars like Messi and Ronaldo have signed international revenue-sharing deals that extend their earnings far beyond club salaries, while Formula 1, the UFC, and golf’s LIV Tour have aggressively expanded into new regions to capture untapped audiences.
Basketball is a global sport and the NBA is building fans beyond its U.S. borders. Cooper will have a platform to position himself as a global star:
China and Africa remain massive growth markets, where top NBA players have already built significant business interests.
NBA Commissioner Adam Silver has hinted at a European expansion, with Paris, Madrid, and Berlin as potential NBA cities.
Maverick Carter, LeBron James' business manager, has been enlisted as an adviser by a group of investors seeking to raise $5 billion to form an international basketball league that would serve as a rival to the NBA.
For Cooper, this means expanding his brand internationally early—whether through overseas basketball camps, multilingual social media content, or partnerships with global companies. The next generation of superstars won’t just be U.S. icons—they’ll be global business leaders.
The Next 15 Years: Building a Billion-Dollar Brand
So what does the blueprint look like for Cooper—and players like him with the potential to become stars —over the next 15 years? It comes down to three key priorities:
1. Dominate the Core Business (Basketball & Endorsements)
NBA success still drives everything—on-court excellence will fuel all business opportunities.
Secure a major sneaker deal (which he’s done with New Balance).
Expand sponsorships beyond sportswear—into tech, media, and finance, where athlete endorsements can have outsized impact.
2. Reinvent the Brand (Media & Digital Growth)
Develop a personal media company—whether through YouTube, documentaries, or even streaming content.
Exploit social media distribution channels—direct-to-fan engagement will be the most valuable long-term asset.
Explore digital-first business models, including training platforms, interactive fan experiences, and even esports integrations.
3. Build Beyond Basketball (Investments & Entrepreneurship)
Take early stakes in high-growth businesses, just like LeBron did with Blaze Pizza or Kevin Durant with Thirty Five Ventures.
Develop a signature brand, whether in fashion, fitness, or media, that extends beyond his playing career.
Long-term, explore team ownership—because the biggest wins in sports business come from owning franchises, not just playing for them.
Our Take: Playing It Safe Is the Biggest Risk
Cooper Flagg is walking into a new era of athlete business—but the biggest mistake he could make is thinking small.
The most successful athletes of the next 15 years won’t just sign endorsement deals—they’ll own the platforms, build the businesses, and create direct fan ecosystems that drive value long after their playing careers end.
The challenge for Cooper isn’t just excelling on the court—it’s making sure his off-court decisions match his on-court potential.
That means:
✅ Thinking like an investor from Day 1—equity, revenue-sharing, and long-term upside should be non-negotiable.
✅ Owning his audience—social media and digital content aren’t side projects, they’re core business assets.
✅ Positioning globally—the NBA is expanding, and players who embrace international growth will win the biggest.
The next generation of athlete billionaires won’t get there by accident.
They’ll get there by playing the long game—and thinking beyond the game itself.
Solid synopsis fam! Also love the European recommendations to potentially get involved before that NBA overseas league materializes. I'm very aligned with everything you wrote except for the Reinvent the Brand (Media & Digital Growth) section. I understand the thought process and think its a viable route to go down, but if he doesn't bring in the right people and have a really interesting narrative to tell, I think that could potentially flop. I think Springhill, Paul George's award-winning podcast, and the Kelce Brothers are outliers. There are probably a few more that I'm not thinking of but I feel like it's a lot easier to just create partnerships with a Netflix, Amazon Video, or Apple TV since they're all diving incredibly deep into sports streaming and documentaries. That's an easy way to get them into a bidding war and come out the winner regardless of who gets the deal.