Before Derek Jeter took the stage at the Westchester Marriott Tuesday night for a Q&A hosted by The Business Council of Westchester, a series of his highlights in a 20-year career with the Yankees played on a big screen.
Many of the big plays have become iconic enough they can be described in only a few words: The Flip, the “Mr. November” World Series home run, the home run for his 3,000th hit and the walk-off single that ended his career at Yankee Stadium. And for about 20 minutes on stage, Jeter answered questions about his storied career, which 
included five World Series titles, 14 All Star game appearances and, announced shortly before the event, will end with his No. 2 retired by the Yankees. He answered questions about his favorite World Series title, saying, like children, he can’t choose. He discussed the different managerial styles of Joe Torre and Joe Girardi, the only two managers he ever played full seasons under, and why it was important for him to play his entire career as a Yankee.
But, as moderator Jeremy Schaap reminded Jeter and the crowd, “I would be more than happy to talk old baseball stuff for the whole time, but we’re supposed to talk business as well.”
Schaap, an eight-time Emmy award winner for work at ESPN, said Jeter had “embraced this next phase of life.” The former Yankee Captain has continued to run his Turn 2 Foundation, which motivates young people away from drugs and alcohol and to healthy lifestyles. He runs a book publishing imprint through Simon& Schuster that prints adult nonfiction titles, children”™s picture books and fiction aimed at middle-grade students.
Jeter also quickly launched the Players’ Tribune online publishing platform after retiring. Created to provide “athletes with a platform to connect directly with their fans, in their own words,” according to a description on the site, the site has quickly become a major force in sports journalism. It publishes all first-person accounts written by athletes, from megastars like Jeter to lesser-known NFL journeymen. The site broke one of the biggest sports stories of 2016: The decision of NBA MVP Kevin Durant to sign with the Golden State Warriors in July, which Durant announced himself through an article on the site.
Jeter said the site has already recruited more than 1,000 athletes to contribute articles.
“A lot of time athletes get a bad rap, because people say they don’t want to speak up, they don’t want to share their thoughts; I heard it about myself all the time,” Jeter said. “My job was to limit distractions for my team and I knew what some members of the media were looking for, they’re looking for headlines. And a lot of athletes do want to speak up, they have interests, things that are on their mind. So we wanted to provide them with that platform and the tools to do it an effective way.”
He added that he “took a lot of heat” from journalists who viewed the site as a threat, but he said he views the site more as a complement to traditional sports journalism.
“It’s been great, because when athletes are speaking to a trusted source, it’s amazing what stories come out,” Jeter said.
Schaap asked Jeter what he learned about leadership from being around business leaders such as George Steinbrenner. Jeter said he likes to ask any leader about the biggest mistake they’ve made.
“The one thing I’m always leery of is when you meet someone who thinks they know everything about everything,” Jeter said. “I’m very good at knowing what I don’t know, and in order to learn I try to surround myself with people who are much smarter.”
Schaap ended the discussion with Jeter by asking what he plans next. Jeter was quick to point toward his goal of owning a team, which he has been open about since retiring. The crowd erupted with cheers at his announcement of ownership aspirations.
“All of you clapping and hooting and hollering, do you guys got some money?” Jeter said in response.
Gesturing to the crowd of Westchester business leaders at the $290-per-ticket event, Schaap joked, “Actually, these guys do.”
Jeter, however, was more tight-lipped on what big league franchise in particular he was interested in.
“Unfortunately you don’t pick and choose where you own a team, a lot of these are generational, so they don’t come up all the time,” he said. “But that’s the next move.”
