Bob Cunningham


Bob Cunningham is a lifelong entrepreneur. His early career was managing and teaching Dale Carnegie Training in Virginia where he attained the position of Regional Manager. After investing in and leading several start-ups, Bob founded Persys Technology, Inc., a multi-million dollar company fueled by wanting to improve our nation’s healthcare system. Persys successfully developed integration software that enabled interoperability across disparate IT systems , paving the way for improved data sharing in the United States. Bob sold Persys in 2004.

Bob is a graduate of the University of Richmond, served on the Board of Directors for Sales and Marketing Executives International, Inc. and served as the International Chairman. Bob also served on the BOD and as Chairman of The Academy of Achievement, an organization that recognizes notable life time contributions to the free enterprise system.

Bob, and his wife Shirley, have been Snowbirds since 2014, and full time Florida residents since 2018. They enjoyed spending 6-7 months a year blue water boating for 10 years, logging 34,000 nautical miles in addition to 30 years sailing the Chesapeake Bay. While Bob’s passion remains being on the water, the Admiral said “enough”. He enjoys golfing, traveling, reading and most importantly, family . Bob and Shirley have two daughters and two granddaughters who are known to wake the neighborhood before sunrise in the pool when they come to visit.

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