Caleb Williams’s Investing Approach: ‘No Vices’

Chicago Bears quarterback Caleb Williams has only played two NFL seasons, but he’s already eyeing team ownership in addition to Super Bowls.

The 24-year-old former USC standout is just over three years removed from winning the Heisman Trophy. But he’s setting himself up for life after football through 888 Midas, an investment firm he launched just a few months after being selected first overall by the Bears in the 2024 NFL Draft.

“We’re here to complete a goal by the end of each year, and that’s to win Super Bowls,” Williams tells Front Office Sports. “That’s always first, that’s always second, that’s always third.”

But he recognizes the unique position he’s found himself in. As a starting NFL quarterback, Williams says he is, “not a part of the 1%, you’re part of the .0001%.”

The 888 portfolio is diverse. Sports investments include just-debuted NWSL expansion team Boston Legacy FC and Monarch Collective, an investment firm that has stakes in three NWSL teams and a German Bundesliga Women’s club, and recently joined the investment group for the WNBA’s upcoming Cleveland expansion team. 888 also invests in tech and health, with examples including Elon Musk’s artificial intelligence company xAI, robotics business Zipline, berry brand Fruitist, and Gwyneth Paltrow’s clean-eating company Goop Kitchen.

“Our main thing is no vices,” Williams tells FOS. “So it’s wellness, it’s tech, and it’s sports. Those three buckets have been the heavy hitters for us.”

Williams points to Fruitist, in which 888 invested late last year, as an example of an investment that has already produced results. He declined to share how much 888 put in—“a good amount”—but Fruitist has grown from $50 million in revenue in 2021 to $400 million while expanding into more than 40 countries, according to a company representative. 888 has an equity stake. 

Williams has long envisioned a life where he’s an owner, not just a player.

“My goal started off as winning the Super Bowl, being one of the greatest to ever walk the planet playing football,” he says. “Then it turned into, when I’m done with all that… to go own a football team. That was one of my first goals growing up as a kid.”

He’d also like to get into Formula One, which he’s “become a really big fan of.”

Partners and Role Models

Williams credits the moves 888 has made to his partners. “They’ve been monumental,” Williams says.

That list includes former Lew Wolff, a real estate investor and former Oakland Athletics owner; John Terzian, a former walk-on football player at USC who cofounded a hospitality firm; Ross Walker, another real estate investor who was also involved in A’s ownership; and Sherif Guirgis, who worked in private equity at Apollo Global Management and Main Street Advisors.

The group met through the USC connection with Terzian, who introduced Williams to the others. 

Williams also credits his business interest to his father Carl, who works in commercial real estate and gym ownership through a company called Athletic Republic Capitol Region. “He showed me hard work and what it takes,” Williams says. 

And as for successful athlete-investors he’s watched for notes, Williams points to Michael Jordan, Magic Johnson, Kobe Bryant, Steph Curry, Saquon Barkley, Joe Montana, and Steve Young.

Thanks to them, Williams says he’s seen the importance of looking to the future, despite being so early in his NFL career: “Creating momentum that way is important to me.”