David Lee Gaylor

David Lee Gaylor, 59, passed away at home on December 13, 2024. David was born on December 27, 1964 to the late Thelma (McKinney) Baseore. His godparents, Troy and Joyce Monday, also played a significant role in his upbringing. 

 David was a hard worker and an accomplished entrepreneur, starting several successful businesses throughout his lifetime. He was the founder of Tradewinds Financial Group and True North Collective, and also founded 3-Mentors with his best friend, Gary Reed. He developed a retirement distribution theory called Income Allocation, and self published a book detailing his process. He traveled the country for many years to share his knowledge through speaking engagements and teaching seminars. 

 David’s family meant the world to him, and he loved nothing more than to spend time with them each year in Hilton Head Island, SC. Spoiling his grandchildren was something he took great pride in doing, and they all adored their G-Pa. He enjoyed golfing with his son, Brady. He was a passionate sprint car and baseball fan, and loved attending races and games around the country. You could always find David in a Tommy Bahama shirt with a smile on his face, and his contagious laugh filled every room with joy. David never met a baby he couldn’t make laugh, or a dog he couldn’t drive crazy. He touched many lives throughout the course of his own, and he will be dearly missed.

 David is survived by his beloved wife, Sandra Gaylor. He was the loving father of Aubrey (Joey) Stutz, Abigail (Britton) Morris, and Brady (Courtney) Gaylor. He was a wonderful “Daddy David” to Braden and Addy Montiglio. He was a proud and doting G-Pa to Leia, Lincoln, Alba, Maren, Emma, River, and Raegan. He is also survived by brother Ken (Jeanie) Gaylor, and sisters Darlene (Dan) Davis, and Bobbie Jo (Dave) Stewart. 

 A Celebration of Life will be held on Saturday, January 11 from 2-5PM at Flanner Buchanan - Washington Park North, located at 2706 Kessler Blvd W. Dr. Indianapolis, IN 46228.