Flip Flops and Pearls, LLC

Reggie Fairchild, CFP®, is the founder of Flip Flops and Pearls, a fee-only financial planning firm in Charleston. With a background in high-growth technology, entrepreneurship, and real estate, Reggie brings a thoughtful, creative approach to helping professionals make confident financial decisions aligned with their values. After leaving the fast pace of Washington, D.C. for Charleston in 2003, Reggie reshaped his own definition of success—an experience that continues to inform his planning philosophy of enjoying life today while preparing intentionally for the future. Flip Flops and Pearls serves high-achieving professionals, business owners, and families who want their money to support a life well lived, not just a balance sheet. Our clients are busy, thoughtful people navigating complex financial decisions and life transitions, from retirement and investments to taxes and long-term planning. As a fee-only firm, we work exclusively for our clients and do not earn commissions or sell products. Our comprehensive approach goes beyond portfolios, helping clients prioritize their time, energy, and resources so their wealth supports both their ambitions and their lifestyle. Life brings change, opportunity, and complexity. Our role is to act as a steady guide—bringing clarity, structure, and calm—so clients can move forward with confidence and enjoy the journey along the way.