Saturday, September 19, 2026

Caleb Williams Beyond the Gridiron

Caleb Williams is more than just the Bears quarterback: he’s also a serious investor with a firm called 888 Midas, built before he ever took an NFL snap. He joins Front Office Sports to explain how his portfolio has come together and how he balances his business endeavors with his full-time job with the Bears.

From a berry company with farms in Peru, to an NWSL team, to a stake in xAI — Caleb’s portfolio is more diverse than most people his age could imagine. Williams explains why he wants to own an NFL team someday, and the sports league he’s personally obsessed with investing in next.

Plus: he clears the air over his “Iceman” trademark battle with NBA legend George Gervin.

Matt Iseman takes viewers beyond the scoreboard, inside the deals, and face-to-face with the personalities shaping sports.

Find Your Local Channel
Up Next

Learfield CEO on $40M Football Rosters, Jersey Patch Boom and Changes in..

Learfield CEO Cole Gahagan on NIL spending, jersey patches and college sports…
September 18, 2026

Mike Tirico on Michael Jordan, Pat McAfee, and Sports Media Landscape

Mike Tirico discusses Michael Jordan’s one season on NBA on NBC.
September 17, 2026

How an MLB Lockout Could Benefit the Savannah Bananas

Jackson Olson talks about the money behind the Savannah Bananas.
September 17, 2026