Candidate Name
Robert “Bobby O” Olszewski
Profile Picture
Robert 'Bobby O' Olszewski

Robert ‘Bobby O’ Olszewski

Office And District
Orange County Commission Candidate District 1
Educational Background (limit 75 words)
Dr. Phillips High School (Orange County Public Schools Diploma)
University of Central Florida – Double Major in Radio/Television (B.A.) and Organizational Communication (B.A.)
Rollins College – Corporate Communication & Technology (M.A.)
Embry-Riddle Aeronautical University – Management (M.S.)
Northcentral University – Business Administration (Ph.D.)
Current Occupation
Commissioner-City of Winter Garden, Adjunct College Professor, Dental Laboratory Director
Civic Organizations (limit 75 words)
Orange County Community Action Board Chair, MetroPlan Orlando Municipal Advisory Committee Vice-Chair, MetroPlan Orlando Regional Leadership Council, Roper YMCA Family Center Board Chair, Roper YMCA Scholarship Campaign Chair, FL League of Cities (FLC), Vice Chair-Finance, Tax, and Personnel FLC Policy Committee, Growth Management and Economic Affairs FLC Policy Committee, Advanced Institute for Elected Municipal Officials (FLC) Graduate, West Orange Chamber of Commerce Board, Full Sail University Sports Marketing & Media Board, UCF Alumni Government Relations Committee Knights Advocate, Leadership West Orange Graduate, OCPS Leadership Orange Graduate, Winter Garden Citizen’s Police Academy Graduate, WG Rotary Club, and FL Citrus Sports.
What are the three top challenges facing the Orange County Commission? Briefly describe how you would address these challenges. (limit 150 words)
1) Orange County needs to become more proactive by investing in resources to keep our residents and community safe.

2) Orange County needs to be more transparent by putting “Residents and Community First” by avoiding cronyism and potential conflicts of interests to ensure smart and balanced growth.

3) Orange County needs a better working relationship with Orange County Public Schools for the school site selection process while ensuring a safe environment for our students to increase their future educational opportunities .

My family does not own any land in the district that needs to be developed, nor does my employer make a dime off of any vote that I have made or will take, as I truly will put “Residents and Community First.” It is critical that we maintain the unique feel and charm of our neighborhoods with smart and balanced growth, including protecting our green space. This is accomplished by investing in public safety by increasing community policing programs and ensuring law enforcement officers have the training and equipment they need to keep us safe. We need to be proactive rather than reactive by communicating with multiple local, state, and national agencies to remain vigilant. Our schools need to be a safe place to ensure future educational opportunities for success. Children traveling to school in construction zones on congested roads while eating lunch at 10AM is not the safe and ideal learning environment we want for our community.

What is your experience working with large budgets, revenue shortfalls, and oversight? (limit 150 words)
As a current Winter Garden Commissioner, I have a voice in managing a $31-million city budget. I have been elected twice by the people to serve as a Commissioner for a city of almost 40,000 residents, which is the third largest city in Orange County. Winter Garden has one of the strongest pension funds in the entire state of Florida in addition to having the highest property value growth in Orange County the last two years. I have two masters degrees in business disciplines as well as a Ph.D. in Business Administration. In my professional career, I have been personally responsible for managing budgets approaching $10-million as well as managing operations with 70 team members.
What are three things “going right” for Orange County? How will you continue forward progress? (limit 150 words)
Tourism, Regionalism, and the University of Central Florida.

As an Orange County Commissioner, I will ensure that our community maintains its spot as the top tourism destination in the world by working closely with our commission, other municipalities, and our theme parks in additional to our industry and community partners, attractions, and hotels. The greater Central Florida community is truly anchored around Orange County, as it is imperative that we work closely with our regional partners from around the state to ensure that our community will be one that everyone can live, work, and play. This is especially evident on our recent success with addressing the homelessness issue as we need to continue to assist our most vulnerable residents. Ensuring opportunity for our residents is hallmark as the University of Central Florida will provide a critical component to the future of Orange County’s success, particularly with its new downtown campus. As the United States’ second largest university, UCF provides training and education while attracting students who will invest in next century ideas, growth and opportunities for our workforce providing for increased economic opportunities for all members of our community.

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Campaign Telephone
(321) 217-8687