The Post Game Podcast #87 - Jack Adler: The Future of NIL and Out2Win’s AI Data-Driven Approach
Jack Adler is the founder and CEO of Out2Win, a marketing platform that uses AI to match brands with athletes. He shares how he turned a passion for helping athletes into one of the most innovative companies in the NIL and creator economy space.
From raising money to partnering with top college teams and brands, Jack discusses what it takes to build something meaningful in the constantly evolving NIL landscape as a first-time founder.
He also dives into how Out2Win uses AI and data to rank athlete marketability, why posting consistency matters more than follower count, and the mindset that kept him from quitting along the way.
What You’ll Hear About:
- How Jack built Out2Win from the ground up
- Why Out2Win partners directly with brands
- Almost quitting and what kept him going
- Raising money as a 23-year-old with zero revenue
- Why one true supporter can change everything
- How athletes are becoming creators
- How Out2Win integrates AI and analytics into athlete rankings
- Why posting frequency matters more than follower count
- The most marketable teams in college sports
- How to navigate the unknown as a first-time entrepreneur
Timestamps:
(0:00) – Intro to Jack Adler
(3:00) – Jack’s upbringing and early drive
(4:20) – Launching his first fundraiser with his sister
(5:40) – Using social media for positive change
(8:45) – The real story behind Out2Win
(9:40) – What NIL really means today
(12:00) – Partnering directly with brands
(15:10) – Is social media essential for athletes?
(17:10) – The hidden struggles of entrepreneurship
(20:10) – Why the name “Out2Win”
(23:40) – Raising capital at 23 with no track record
(26:55) – Landing the first investors
(28:25) – How he was intentional with his fundraising
(30:40) – The tailwinds pushing college sports forward
(32:50) – How Out2Win uses AI and data
(34:30) – What goes into the Out2Win score
(37:40) – NFL QBs and athlete content creation
(40:20) – Deloitte’s role in NIL
(43:40) – Making sure brands are educated
(45:40) – Balancing athlete and brand interests
(47:40) – The most marketable team in college sport
(49:25) – Finding hidden gems in recruiting
(50:10) – Why Instagram and TikTok matter most
(52:10) – The $20.5M cap and its recruiting impact
(54:55) – Expanding into pro and high school sports
(57:10) – Competitors (and what sets them apart)
(58:30) – What excites him most about the future
(1:00:00) – Building Out2Win’s culture his way
(1:02:40) – Favorite Philly athlete
Links:
The Post Game Podcast:
https://postgamepodcast.beehiiv.com/
https://www.instagram.com/thepostgame_podcast/
https://x.com/JoePod24
https://www.linkedin.com/company/the-post-game-podcast/
Email me: joe.poduslenko@gmail.com