This story appeared in the May 19, 2014, issue of Sports Illustrated. Subscribe to the magazine here.
With the sun beating on his head, Cal Ripken Jr. leans on the fence along the third base line, watching the game and absently spitting sunflower seeds. He turns 54 later this summer but still looks like a ballplayer -- 6'4" with an easy grace and the thick build of a cleanup hitter. On this warm March day Ripken, clad in a T-shirt, basketball shorts and cleats (all Under Armour), has come to Port St. Lucie, Fla., to watch his son, Ryan, a 6'6" redshirt-freshman first baseman at Indian River State College. When Ryan steps up to the plate, Cal mutters, "C'mon, bubba. Big hit. Hit it hard."
And then Cal steps away ... to take a business call.
Ripken played 21 seasons for the Orioles, making the All-Star team in all but two, before being inducted into the Hall of Fame in 2007. He won a World Series ring, two MVP Awards and a pair of Gold Gloves at shortstop. He is best known, of course, for his unparalleled record of going to the ballpark for almost 17 years without missing a day, a streak encompassing 2,632 consecutive games. It was a feat of professionalism and durability that earned him the nickname Iron Man.
Not surprisingly, Ripken's industriousness wasn't limited to baseball. Long before he was down to his last few at bats in the majors, in 2001, he was planning for Career 2.0. "Right around 30 years old you start to think about how to prepare for the next phase of your life," recalls Ripken, who made roughly $70 million during his career, hardly chump change but nothing next to today's superstars, who make in excess of $20 million a season. "When you're playing, you're making contacts, you're meeting people all over the place. So I always thought, Take advantage of those contacts to set up for your postcareer."
Ripken says that the day after his retirement in Baltimore, he went on another streak of sorts. "I had to take the baseball uniform off, put a suit on and go to work," he says. Thirteen years later Ripken resists a one-word description for his job -- he's no longer a ballplayer or an Oriole -- but he can do it in four. "The business of Cal," he says. "I've invested mostly in myself. If you're going to put your money someplace, put it behind you."
His privately held company, Ripken Baseball, operates two youth-oriented complexes, each called The Ripken Experience. One, in Aberdeen, Md., puts on weekend kids' tournaments and longer camps on fields modeled after classic current parks such as Fenway and Wrigley. The other, in Myrtle Beach, S.C., offers weeklong tournaments on fields that mimic bygone venues such as Ebbets Field.
The Ripken Experience in Aberdeen is populated with kids every weekend from March though Thanksgiving. (Ripken has a small equity stake in a Marriott property on the site.) And the complex at Myrtle Beach has been a lure to family vacationers. Both are growing fast enough that Ripken's next planned step is to duplicate the facilities across the U.S.
Despite this success Ripken is quick to admit that he hasn't batted 1.000 in business. At first he focused on owning minor league franchises. In the fall of 2001, before he had even retired, Ripken was approached about helping set up a new baseball facility in Aberdeen, his hometown. Using his clout and reputation, Ripken helped negotiate a public-private partnership for a $21 million stadium project. He then purchased the Utica (N.Y.) Blue Sox, a short-season Class A team, for $3 million and moved it to Aberdeen, renaming it the IronBirds.
In 2005 he purchased the Class A Augusta GreenJackets and in '08 the Class A Charlotte Stone Crabs. He sold the GreenJackets in 2012 for a reported $7.5 million (a slight profit) because the team didn't have enough success to justify a new stadium, which was considered a long-term necessity. "We kind of got caught by the politics of it," he says. "We had immediate success [with the IronBirds], and I assumed that success could be applied everywhere. But I think in hindsight, we got diverted toward minor league teams. The future growth for us now is in youth complexes and tournaments."
Having learned from the experience, Ripken has moved the business of Cal in other directions. Ripken is still an endorser, for brands such as Kellogg's, NewDay USA, Chevy, Northern Safety and Baltimore-based Under Armour, likely earning in the single-digit millions per year for each. He is a part-time TBS baseball broadcaster and takes on speaking engagements that can fetch $50,000 a pop. He has a six-book deal with Disney to cowrite a kids' series about sports. (He just put out the fourth, Squeeze Play.) He's a vice chairman of the charity named for his dad, the Cal Ripken Sr. Foundation. And he sits on the board of ZeniMax Media, a private, Maryland-based company worth more than $1 billion that mostly produces role-playing video games and is working on a baseball product.
But the youth baseball complexes are both the core business and the growth sector. "We run tournaments very well, and we're selling tournaments very well," Ripken says. "As that starts to grow, the model doesn't have to have me in the equation." As his younger brother, onetime teammate and business partner, Bill Ripken, puts it, "He's always going to be that guy—the Iron Man. But 50 years from now, when that guy might be gone, the complexes will still be running strong."
If he's freed from Ripken Baseball, what else might Cal do? Last year his name popped up in the search for a new Nationals skipper. "It was fun to be spoken of in a manager position," he says, but "it never got to a formal stage." Still, he adds, "As I go forward, I do think about things like that. Where do I want to spend my time? Is the window open still, or is it closed? Where could I come back?" Whatever he decides to pursue, rest assured he'll work hard at it. Every day.