Bob Bloebaum was born and raised in the Midwest. He moved from Vincennes, Indiana to Winter Garden, Florida in 1961. In 1968, Bob graduated from the University of Florida. He served several terms on the church council and was President of the congregation at the Shephard of the Hills Lutheran Church in Clermont. 

He was the co-owner of Dal-Don Produce Inc (brokerage and shipping) in Clermont, Florida, which was founded in 1966 by Bob's father (Don Bloebaum.) and Dallas Jones, and operated for over 40 years. The company shipped more than 3,000 truckloads of watermelon during its peak years. Dal-Don handled products from about 2,500 acres in several states in the south and the Midwest.

Bob served on the Executive Committee of the National Watermelon Association.