In 1981, following his move to Chicago, John founded the Gatewood Group, a comprehensive financial planning services firm. In 1984, the company relocated to St. Louis. Under John’s leadership, it experienced consistent growth and transformation, culminating in what is now known as Gatewood Wealth Solutions. Today, the company is known as a well-regarded financial planning firm, as recognized by Barron’s.

In a significant transition in 2021, John confidently entrusted the company’s future to a team of highly skilled internal advisors by selling his business. Although he has stepped back from ownership, John remains actively involved as Director of Advisor Development, focusing on elevating advisor expertise and confidence. His efforts support the firm's vision of providing experienced, relationally driven, enduring care by equipping advisors with the knowledge, tools, and confidence for exceptional client experiences.

John, a native of Washington, D.C., grew up as one of thirteen children. Demonstrating leadership and talent early on, he excelled as a member of Northwestern University's soccer team and pursued his passion for music by performing in nightclubs around the D.C. area. Fluent in Spanish from his time studying in Mexico, John now resides in Naples, Florida, with his dear friend, Judy Smart. He honors the memory of his late wife, Annie, and is immensely proud of both of his children. His daughter, Sophia, is married to Nick Shealy, and the couple resides in Washington, D.C. A fluent Arabic speaker who spent two years in Jordan, Sophia previously served with the U.S. State Department and founded Gatewood Defense Solutions in Washington, D.C. She now serves as Director of International Ventures and Government Affairs at Keystone International Ventures. His son, Anthony, a former lacrosse scholarship athlete at Tusculum University, lives in Sarasota, Florida with his fiancée, Josey Powell. Anthony successfully established Quality Window Wipers, which he continues to expand in Florida, and is currently studying for his medical sales certification.