Derek Jeter talks about using the lessons of baseball in business

For many baseball fans, it definitely doesn’t 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 franchise Miami Marlins in 2017, and on after being regularly inducted into the Baseball Hall of Fame in 2020.

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

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

He has even been a part of several comedy films, playing small roles in both Anger Management, the 2003 films starring Adam Sandler and Jack Nicholson; and 2010 The other guys, starring Mark Wahlberg and Will Ferrell. Shortly after his retirement from baseball, Jeter also joined NFL megastar Peyton Manning on TV in February 2015 to celebrate Saturday Night Live’s 40th anniversary.

Jeter’s business interests include not only lucrative endorsements inside and outside the U.S. In addition to his investment and management of the Marlins, Jeter has been involved with publisher Simon & Schuster, as well as a handful of investment, food, and technology ventures. .

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

In founding UNTUCK, Riccobono expanded the shirt and apparel brand to include 86 stores across the US, Canada and the UK, and also shaped UNTUCK to become one of the most successful e-commerce businesses of the decade the past. Adding to Riccobono’s entrepreneurial edge and Jeter’s deep organizational management expertise, Copeland brings several years of knowledge gained from her previous experience helping to develop her athletic apparel venture.

Launched in June 2022, the Greatness Wins brand offers lines of high-performance exercise and comfort apparel for men, women and children.

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

Andy Frye: Many sports legends such as Tom Brady AND Lindsey Vonn have entered the fashion clothing business. What was your motivation for creating Greatness Wins?

Derek Jeter: Most of my life has revolved around being active, working out, and challenging myself to compete. I’ve worn many different types of athletic wear over the years, so I have strong opinions about how the product should perform. When Chris Riccobono and I started discussing this concept, we focused on key areas that we thought would improve this space, including elevating the fabrics used, focusing on quality and durability, and perfecting the fit of the available products.

The experience Chris brings from running UNTUCK for over 10 years is so valuable as we build 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 is no single definition of “athlete” and no single path to being an athlete. What unites us is a competitive drive and a shared desire to be the best we can be in everything we undertake.

AF: What lessons have you learned from baseball that can be transferred 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 being fully committed to the goal at hand, which 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 do you bring to Greatness Wins?

Jeter: I was really looking for a true partnership when I created Greatness Wins, not just an endorsement deal. I am learning a lot through this process and hope to bring 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 how to continue to advance our goals and continue to build. I like to do my research and pay attention to detail.

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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 myself. What I miss are the friends in the dressing room and the adrenaline moments that the big games provided.

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


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