Our Leaders

Doug Annakin

Partner | President – Evansville

Douglas Woody Annakin, 54, of Evansville, passed away Friday, May 22, 2020 at his home after a courageous battle with cancer. For 27 years he was the beloved husband of Peggy (Likens) Annakin and proud father to his daughter, Berkley and son, Baxter Annakin. Born January 25, 1966 in Indianapolis, IN to Jane (Bardwell) Annakin and the late Joseph Woody Annakin, “Doug” graduated from Bosse High School and The College of William & Mary where he was a member of the nationally ranked Tribe soccer team.


Doug spent 30 years in the insurance industry and was currently Partner and President- Evansville Operations at Shepherd Insurance & Financial Services. Doug served as a past President of the local chapter of the Independent Insurance Agents and was named President of the Independent Insurance Agents of Indiana “Big I” in 2007. He served as President of the Evansville Country Club in 2013 and was a member of their Board of Directors 2011-2014. Doug was active in the community and an integral part of the YMCA. He was currently serving as secretary of the YMCA Board of Directors and was a Metro board member for the past 12 years. He was also past Chairperson for YMCA Annual Campaign, Chairman of Branch Board Managers for the Dunigan Family YMCA 2009-2010, and chaired the YMCA triathlon for 6 years. He loved and lived life to the fullest. He particularly loved to spend time with his family, friends, playing golf, and watching high school and college wrestling. Doug acquired many close friendships in his lifetime including his college soccer teammates who called him “Guido”.


To know Doug was to love and trust Doug. He was an honest, ethical, and a moral man of high integrity. As a result, Doug had a long list of close friends and business associates in his community. He was a kind, fun, funny, and caring person. Had a way of making everyone feel important and appreciated. Doug never forgot a name. These are attributes that are used to describe many people, but with Doug, they are true in every sense. He will be truly missed by all who knew him.

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