Bobby Gillenwater works with professionals whose finances have grown more complex, helping them simplify decisions, make tax‑aware investment choices, and feel confident they’re not overlooking something important. His focus is on bringing clarity and structure to financial planning and investment decisions as careers, income, and responsibilities evolve.
Before becoming a financial advisor, Bobby spent more than 20 years in U.S. Navy Special Operations as an Explosive Ordnance Disposal (EOD) officer. His career included deep‑sea dives to identify a WWII submarine, disarming IEDs in Iraq, and leading large‑scale global exercises involving senior military leadership. That experience shaped how he approaches complex situations today—staying calm under pressure, organizing complexity, and making sound decisions when there are many moving parts.
As a Financial Advisor with Raymond James, serving clients through the Waterfront Advisory Group, Bobby takes a planning‑first, long‑term approach. He helps clients coordinate investments, tax strategy, and broader financial decisions within a disciplined, cohesive plan—so choices are intentional rather than reactive and aligned with long‑term priorities.
Bobby is known for helping clients move from uncertainty to clarity by creating structure around their financial lives. Through ongoing planning, professionally managed investments, and regular reviews, his goal is to help clients remain focused on their careers, businesses, and families while knowing their financial strategy is being actively and thoughtfully managed.
Bobby earned his undergraduate degree in international business and naval science from Jacksonville University and holds an MBA from Florida International University. He has lived in the Hampton Roads region since 2009 and currently resides in Chesapeake, Virginia, with his wife, Stefani, and their two daughters. Outside of work, he enjoys church involvement, coaching and playing softball, golfing, snowboarding, and spending time outdoors with his family.
