Dan O'Dowd Circles The Bases

The Boca Grande Resident And Former MLB General Manager Talks Executive Decisions And His New Tech Startup: WIN Reality

Dan O’Dowd is a humble guy who has no real right to be one. After all, just look at what he has accomplished. The son of a New Jersey dairy farmer, Dan’s 40-year career in Major League Baseball saw him make the 2007 World Series as General Manager of the Colorado Rockies, the 1995 and 1997 World Series as Assistant General Manager of the Cleveland Indians, and win the 1983 World Series with the Baltimore Orioles as a young executive. In 2009, he was named MLB’s General Manager/Executive of the Year. Over the past seven years, he’s been a regular analyst on MLB Network. And he’s recently launched a tech start-up—WIN Reality—with his eldest son, Chris. 

By the time he was six-years-old, Dan knew baseball would be his life. Recruited to play at Florida’s Rollins College, he quickly recognized he wasn’t the most talented player on the field. He decided that even if he wasn’t going to be a professional MLB player, he could aspire to be a MLB executive. He was accepted into MLB’s Executive Development program, a coveted national internship that only took on two young people per year. His first mentor, Bill Murray, gambled on Dan, and so did his next, the Orioles' Hank Peters.

“They saw something in me,” Dan explains. “Those were the guys who really gave me a chance.”

His ensuing career in Major League Baseball is storied. For more than three decades, he spent 200 days per year on the road while raising three children with his wife of 32 years, Jackie. “If I could do anything over,” Dan says, “it would be to have better work-life balance. Everything I’ve achieved is due to Jackie. She saw my passion for my career, and she supported me in every way. She raised our three kids—Chris, 31, a Dartmouth graduate, Lexie, 27, a Vanderbilt graduate who was just married in February at Boca Grande’s Gasparilla Inn, and Jack, 20, a sophomore baseball player at the University of Texas—to be the wonderful people that they are. That they are such great kids is absolutely due to her.”

For her part, Jackie has a slightly different take. “While I appreciate Dan giving me all the credit,” Jackie says, “if you ask our kids, they’ll tell you they felt Dan’s presence all the time. He’d call us throughout the day to check in with us when he was on the road. He was an amazing father. Yes, there were many evenings that I packed the kids up and drove them to the stadium so they could see him, but they didn’t mind because they loved getting to do that and see a ballgame!”

And now Dan gets to work with his kids. Based on an idea he had around 2016, and starting in earnest when his son Chris retired from his own six-year minor league baseball career in 2018, Dan and Chris launched WIN Reality, a VR program focused on improving baseball players’ hitting. Chris leads all the company’s operations as CEO. Daughter Lexie now handles the company’s social media. The company has grown under Chris’s leadership to include more than 50 employees, and with their Oculus-based hitting program now being used by most MLB teams and over 200 colleges and major success in sight, Dan will likely have to learn how to be humble all over again.

“There are two types of people in sports,” Dan says and laughs. “Those who are humble, and those who are about to be. In my career as a general manager, I really learned what it was like to live alone on an island. I was responsible for 150 people and I got a grade every single day in the form of a win or a loss. It teaches you resiliency. Our company name comes from something I used in player development—‘What’s Important Now’. I’d tell my players, ‘Worry about what you can work on in the present, and the future will take care of itself.’  I learned that though I was ultimately responsible for the losses, I was really responsible for developing all the players and staff into being their best versions of themselves. Working with my children now is utterly wonderful. I fully believe that Chris will be recognized as one of the nation’s best CEOs under 40 based on the work he’s done with WIN Reality and the success that we are having.”

A true tech startup, Win Reality is based in Austin, Texas, where many virtual reality developers are located. The company began in a simple 1,000 sq. ft. office with Chris putting in countless hours of work.  

“Now we have really grown,” Dan explains. “It has the feeling of one of those tech ‘unicorns.’ Hitting is all about timing. It’s nearly impossible to approximate game-speed pitching and hitting outside of playing the actual game. WIN Reality’s software allows the user to experience game-speed pitching in virtual reality. We offer a variety of different drills to allow the user to see where their hitting measures in an average of players in their age group. It’s amazing where Chris has taken the company as CEO. And we have only penetrated 15-20% of the available market!”

PULL QUOTE: "I have noticed three qualities that all good executives possess," says MLB Network analyst and WIN Reality founder Dan O'Dowd. "First, they process thought quickly. Second, they are creative thinkers. And third, they are world class problem solvers."


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