Ryan Woolsey brings over 15 years of experience in finance and wealth management, combining a deep understanding of money’s purpose with a passion for helping clients build meaningful, lasting wealth. A graduate of the University of North Texas with a BBA in Business Economics, Ryan began his financial career while still in college at a community bank, where he developed a strong foundation in client relationships and banking fundamentals.
Over the years, Ryan’s career has spanned mortgage servicing, relationship management, and private banking. He served as Vice President and Relationship Manager for a high-net-worth private client bank in Highland Park, TX, before taking on the role of CFO for a private family office specializing in private equity and venture capital investments in Dallas. His breadth of experience—from institutional finance to personal financial strategy—gives him a unique perspective on how to balance opportunity, stewardship, and long-term vision.
Ryan also spent time as a high school business and finance teacher, where he sponsored the DECA team and inspired the next generation of future entrepreneurs and financial leaders. Today, as a Financial Representative with Rethink Wealth, he draws on his diverse background to help clients view money not as the goal itself, but as the tool that enables the life they truly want to build.
Outside of work, Ryan’s greatest joy comes from spending time with his two boys, ages 10 and 7. Together, they enjoy hockey—whether playing, coaching, or officiating—along with soccer, fishing, puzzles, Legos, movies, and walks with their Beagle. Ryan also enjoys turning wrenches, tackling home improvement projects, and taking time to unwind with a good book—one with real pages to turn.
Financial Representative of The Guardian Life Insurance Company of America® (Guardian), New York, NY.