Bobby O’s Journey to the City Commission

(Photo by Judy Watson Tracy)

Robert "Bobby" Olszewski '01MA was accustomed to throwing out pitches. As a ruddy-faced boy running around the little league field in his Dr. Phillips neighborhood, he dreamed of growing up to become a professional baseball player. As his adolescent years waned and high school was only memory, Olszewski hung-up his leather mitt and started pitching sports news updates on three different Tampa Bay radio stations, setting his sights on becoming a sports broadcaster. Over fifteen-years later, he was throwing pitches of his own.

“For those of you who don’t know me, my name is Bobby Olszewski and with a last name like Olszewski, you can see why my friends just call me Bobby O,” said Olszewski to any audience that would listen. “I am here because I am running for the Winter Garden Commission in District 3 and I need your support.”

After completing three grueling months earlier this year on the campaign trail, Olszewski has the satisfied smile of a victor who triumphed with 70 percent of the vote, winning the three-way race against the two-term incumbent and a fellow challenger.

“I personally walked Winter Garden neighborhoods three out of every five weekdays and all day on Saturday and Sunday,” Olszewski said, his reddened brow evidence of time spent under the unforgiving Florida sun. “I knocked on every voter’s door at least twice, sometimes even three or four times. I was honored that I was able to resonate with the people and I look forward to serving the people of Winter Garden as long as they will have me.”

So how did the media relations professional turned executive marketing and management consultant become a public servant?

“I’m a firm believer in being flexible, always looking for opportunities, and recognizing how to capitalize on them once they are identified,” Olszewski said

Olszewski also credits his strong educational background as a fundamental component to the development of his career and his success as a community leader. After earning a bachelor’s degree in radio/television and organizational communication at the University of Central Florida, Olszewski enrolled in the Hamilton Holt School’s graduate program.

“I definitely value my Rollins education,” Olszewski said. “It was such a different dynamic to go from a major research university to Rollins. It was a wonderful experience from the standpoint that I really felt I had one-on-one learning not only with my professors but also with my fellow students.”

After completing his master’s degree in corporate communication and technology, Olszewski became an adjunct professor at the Hamilton Holt School, creating the popular course Sports and Entertainment Communication, while also earning a second master’s degree in management from Embry-Riddle Aeronautical University and a Ph.D. in business administration from Northcentral University.

“You have to be a lifelong learner; as that’s one thing that was constantly ingrained in us at Rollins,” Olszewski said. “You have to continually grow. It doesn’t matter what field you are in—you have to be ready to better yourself, to work harder, to provide a better service, to do better for your organization, your family, and your community.

This optimistic mentality and dedicated work ethic may be what convinced Winter Garden voters to elect “Bobby O” as their Commissioner.

“I think the political world is changing,” Olszewski said. “People respect the fact that someone can be self-made—that someone has real-world experience and knows what it’s like to have to sacrifice and struggle. Most people think that campaigning is the only part of politics that matters. At the end of the day, you can be a great people person and connect with the voters, but you also have to be an analytical thinker and strategist. You have to realize what you are voting on and how you are impacting all of the people you are elected to serve.”

By Brittany Fornof

Office of Marketing & Communications
For more information, contact news@rollins.edu