Barry is a certified financial planner and the retired founder of Freedman Financial Associates, Inc. He served on the National Board of Certified Financial Planners as Chairman and President of the Greater Boston Chapter of the International Association for Financial Planning. From 2015 to 2018, he served on the Board of Governors of the Estero Country Club. He also served as the Membership Director of the Estero Council of Community Leaders and on the Village of Estero Design Review Board.