Derek Jeter Talks About Using The Lessons Of Baseball In Business

For many baseball fans it definitely does not seem like the better part of a decade ago that Derek Jeter retired as a player.

After his final appearance for the New York Yankees on September 28, 2014, the Yankees lifer and five-time World Series winner later became part owner and CEO of the National League’s Miami Marlins franchise, in 2017, and after that was duly inducted into the Baseball Hall of Fame in 2020.

And despite not being seen glove-in-hand on nightly national broadcasts—for nearly eight years now—it seems like Jeter is always ever-present.

Jeter has been seen on TV commercials for Gatorade, NikeNKE
and Michael Jordan’s Jumpman brands, Gillette, Subway, Skippy peanut butter and Discover Card. The right-handed shortstop and 14-time MLB All-Star has also been featured in a number of documentaries and TV specials about the Bronx Bombers. But that’s not all.

He’s even been part of a few comedy movies, playing small roles in both Anger Management, the 2003 films starring Adam Sandler and Jack Nicholson; and 2010’a The Other Guys, starring Mark Wahlberg and Will Ferrell. Right after his retirement from baseball, Jeter also joined NFL mega star Peyton Manning on TV, in February 2015, to celebrate Saturday Night Live’s 40th Anniversary.

Jeter’s business interests include not just lucrative endorsements in and outside the U.S. In addition to his investment with and management of the Marlins, Jeter’s been involved with publisher Simon & Schuster, as well as a handful of few investment, food and tech-related ventures.

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And now, you could say, Jeter has gotten into the fashion business. Earlier in 2022, Jeter teamed up with UNTUCKit founder and serial entrepreneur Chris Riccobono to build a completely new performance apparel brand called Greatness Wins. Also on board of the new brand’s founding team are NHL legend Wayne Gretzky and ballet and dance icon Misty Copeland.

In founding UNTUCKit, Riccobono scaled the shirt and apparel brand to include 86 stores across the US, Canada, and Great Britain, and also fashioned UNTUCKit to become one of the most successful e-commerce businesses of the past decade. Adding to Riccobono’s entrepreneurial edge and Jeter’s large organization management expertise, Copeland brings several years of knowledge gained from her previous experience helping to develop her own athletic wear venture.

Launched in June 2022, the Greatness Wins brand offers lines of high-performance workout and comfort wear for men, women and kids.

In late June, I was able to connect with Greatness Wins and Jeter, to ask him a few questions about the new endeavor, as well as how baseball translates to life in the business world.

Andy Frye: A lot of sports legends such as Tom Brady and Lindsey Vonn have gotten into the business of fashion apparel. What was your motivation for creating Greatness Wins?

Derek Jeter: Much of my life has revolved around being active, training, and challenging myself to compete. I’ve worn a lot of different types of athletic wear throughout the years, so I have strong opinions on how the product needs to function. When Chris Riccobono and I started discussing this concept, we focused on key areas we thought would improve this space, including elevating the fabrics used, focusing on quality and sustainability and perfecting the fit of the products available.

The experience Chris brings from having run UNTUCKit for over 10 years is so valuable as we build out Greatness Wins alongside Misty Copeland and Wayne Gretzky. The four of us coming together also highlights something that is important to all of us – there’s no one definition of “athlete” and no one path to being an athlete. What unites us is a competitive motivation and a shared desire to be the best we possibly can be in everything we undertake.

AF: What lessons have you learned from baseball that are transferable to ventures like this?

Jeter: I’ve always understood the importance of having a great team and surrounding yourself with experts, and that’s no different than the approach I take with entrepreneurial ventures. I also understand the importance of fully committing yourself to the goal at hand, which is something I think all successful athletes share.

AF: Obviously your name is valuable to any business partnership, but what other attributes of your personality and skill set have you brought to Greatness Wins?

Jeter: I was really looking for a true partnership when creating Greatness Wins, not just an endorsement deal. I’m learning a lot throughout this process and hopefully bringing a lot to the table as well.

I am very involved in all aspects of the brand, and I wouldn’t want it any other way. I work with Chris and our design team on the vision for each season’s line, on our marketing plans, on creating our customer strategy, and on how to keep advancing our goals and keep building. I like doing my research and paying attention to the details.

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AF: The Yankees are having an impressive 2022. What do you miss most about your days on the field?

Jeter: I know I retired at absolutely the right time for me, because I don’t miss playing itself. What I do miss are the friends in the locker room and the moments of adrenaline that big games provided.

Read Frye’s interviews with Tom Brady and Tracy McGrady.

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