Bigger Than Big
Entrepreneur magazine|February 2019

Michael Strahan was a star NFL football player. Then he retired and faced the ultimate question: How do you redefine yourself in a world full of unknowns?

Mary Pilon
Bigger Than Big

Socks. It’s a Tuesday afternoon in October, and Michael Strahan is deep in thought about socks.

“We can do more of these non-solids in a solid,” says Douglas Raicek, president of the trouser division at Peerless Clothing, as Strahan contemplates a pair of gray socks in his hands. The two are at work developing Strahan’s upcoming men’s fashion line for JCPenney, reviewing a rainbow mountain of socks in a glass-walled Manhattan conference room. “I think that would be more fashion-forward,” Strahan says. “You can’t be too fashionable, because you still have to appeal to a mainstream customer,” Raicek replies, Strahan nodding.

Michael Strahan: the cheery man with a gap-toothed smile, known to the masses as a Good Morning America cohost, an analyst on Fox NFL Sunday, the $100,000 Pyramid emcee, and now also a fashion designer. Years ago, the whole thing would have been unimaginable. Strahan was a New York Giants football player then, full stop. It’s what he knew, and it’s what he was known for. But for all the money, glitz, and glamour of professional football—the Super Bowl ring, the Hall of Fame status, the healthy salary—Strahan the athlete was painfully aware that he didn’t control his own destiny. When he retired from the game a decade ago, he knew he needed to change that—to learn what it really means to take control and then fully own it. Or to put it in football terms, which Strahan is known to do constantly, he needed to go from defense to offense. “Everything that has come after that hasn’t necessarily been a plan to say, ‘This is step one, and this is step two, and this is step three,’ ” Strahan says, outside the socks meeting. “It’s just been taking advantage of opportunities and creating opportunities to expand and try new things, to try and challenge yourself.”

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