đź’° The NIL Bubble Is About to Pop - But What's Next?

The era of "pay-to-play" isn't over; it's just getting a reset.

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Happy Wednesday,

The NIL market is booming—and broken.

In just four years, it’s grown from $917 million to $1.67 billion and is expected to hit $2.55 billion by 2026. But 80% of that activity flows through collectives that operate more like payroll systems than marketing channels.

Most of this money isn’t going to the most marketable athletes. It’s going to the ones with the most TV time—and not always the best ROI.

Enter Jack Adler.

Jack founded Out2Win, a platform that helps brands find and evaluate athletes based on how they actually perform off the field—as content creators, influencers, and marketers. His company assigns each athlete a dynamic score based on follower growth, engagement rate, and historical sponsorship performance.

This week, Jake and I sat down with Jack to talk about the reality of NIL deals, how influencer athletes are beating five-star recruits, and why the system may not be sustainable—but still has a lot of upside.

Big investors are buying this “unlisted” stock

When the founder who sold his last company to Zillow for $120M starts a new venture, people notice. That’s why the same VCs behind Uber and eBay also backed Pacaso. They made $110M+ in gross profit to date. They even reserved the Nasdaq ticker PCSO. Now, you can join, too.

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5 Takeaways From Our Conversation With Jack Adler

Jack Adler, Founder of Out2Win

1. There are two NIL markets—and most people don’t realize it.

  • Real NIL = influencer marketing, brand partnerships, content creation.

  • “Fake” NIL = pay-to-play deals from booster collectives.

  • Out2Win plays in the real NIL space, helping brands find athletes who create actual marketing value—not just game highlights.

“It’s name, image, and likeness—but that’s not even what they’re getting paid for.”

Jack Adler, Founder of Out2Win

2. Most NIL money is being funneled through collectives—and that’s about to change.

  • In 2024–25, collectives accounted for 80–81% of all NIL compensation.

  • That’s starting to face regulatory pressure via the House v. NCAA settlement and the new College Sports Commission, which now requires proof of promotional value.

This shift could dramatically reduce collective dominance and bring NIL back to what it was intended to be: marketing.

3. Big names don’t always bring big results.

  • Arch Manning has a $6.8 million NIL valuation—but has posted on Instagram fewer than 20 times.

  • By contrast, athletes like Bryson Webb (yes, my brother) consistently create content that integrates brands more naturally and gets better performance.

“You can fit a brand into that type of content a whole lot easier than having Arch post for the 21st time.”

Jack Adler, Founder of Out2Win

4. The market is maturing—and brands are finally paying attention to ROI.

  • Brands no longer want to “spray and pray.” They want data, performance history, and real engagement.

  • Platforms like Out2Win help them discover lesser-known athletes who consistently outperform big names on social.

That’s where the opportunity lies: not in bigger checks, but in smarter ones.

5. This isn’t the end of NIL. It’s a reset.

  • Athlete compensation is expected to surpass $7M annually at top programs when NIL + scholarships + revenue sharing are combined.

  • But traditional $10K–$50K influencer deals? They’re no longer worth it for most big-name players.

“That money doesn’t disappear, it just shifts to athletes who actually create content. That’s where brands will go.”

Jack Adler, Founder of Out2Win

Why It Matters

NIL didn’t fail—it just got hijacked.

What was supposed to be about name, image, and likeness turned into pay-to-play. But with regulation tightening and ROI becoming a priority, the market is shifting back toward what it was designed to reward: performance off the field.

Jack and Out2Win are helping shape that next chapter. They’re giving brands the tools to make smarter decisions—and giving lesser-known athletes a shot at the spotlight.

📩 And don’t forget: Bottom of the Ninth is back this Friday with the top three stories in sports and business from the week.

See you then,
Tyler & Jake

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