After Derek Jeter retired in 2014, the star shortstop waited two whole days before announcing his next venture: The Players' Tribune, a digital media company that lets athletes write directly to the fans.

Three years later, how does entrepreneurship compare with playing baseball on the world's biggest stage?

"When you're in baseball, if you fail 70 percent of the time you're considered great," Jeter, who had a .310 batting average during his career, said on Thursday. "Those numbers might be similar here," he said with a laugh.

The athlete-turned-entrepreneur, always careful to avoid controversy, made sure to clarify that he wasn't talking about the failure rate for The Players' Tribune--but for entrepreneurship in general.

Jeter spoke on stage in New York at the Fast Company Innovation Festival. Sitting alongside company CEO Jeff Levick, the Yankees great said that, fortunately, entrepreneurship offers the freedom to experiment outside of the public eye.

"In sports, your failures are seen by millions of people," he said. "We try a lot of different things behind the scenes [at The Players' Tribune]. Some are successful and some fail. Many of them, you'll never see or know about." 

For those unfamiliar, Jeter's company gives athletes a platform to deliver first-person stories or heartfelt messages. On Thursday, he said he began the company as a platform for athletes to communicate with fans directly, without fear of having their words twisted by publications looking for headlines and clicks.

Traditional media outlets need not panic yet: Currently, the site gets about 3 million unique visitors per month, according to Levick. By comparison, ESPN.com pulls in about 85 million.

During the talk, Jeter referred several times to the breakdown of trust between media outlets and athletes. He said that it was a topic players talked about often during his career, so he wasn't surprised when they embraced his business idea.

The Players' Tribune has run stories by more than 1,200 athletes in the three years since its founding. It's pulled in nearly $60 million in funding, and has started venturing into podcasts and video.

Jeter is part of a group that was approved to purchase the Miami Marlins in September, so he likely won't be bored during his so-called retirement. 

When asked his best advice for fellow founders and leaders, the five time World Series winner talked about what he's learned in his new role.

"Get to know the people you're leading," he said. "Don't treat everyone the same--treat everyone fairly." In both sports and business, he said, different leadership styles work for different people, so screaming probably isn't a universal motivator.

Not that the even-keeled lifetime Yankee probably does much yelling. "Earn everyone's respect," he said, "and find out what works for them."

Published on: Oct 26, 2017