On this episode of the Sports Business Leaders Podcast, we sit down with Jack Adler, founder and CEO of Out2Win — the AI-powered NIL marketplace reshaping how brands connect with athlete entrepreneurs.

Jack shares the journey from running a traditional athlete marketing agency to raising a $1.3M seed round and building Out2Win’s proprietary platform, which ranks over 250,000 athletes by off-field marketability. We explore how the Out2Win Score helps brands make smarter sponsorship decisions and why holistic metrics like social media engagement are key in today's NIL era.

The conversation also dives into the House vs NCAA settlement and its implications on college athletics. With revenue sharing on the horizon and schools preparing for major structural shifts, Jack offers insight into how this uncertainty is impacting brands, universities, and the broader NIL ecosystem.