Reggie Fairchild

Financial Advisor for entrepreneurs and professionals and their families.

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Flip Flops and Pearls Reggie Fairchild
Mount Pleasant, SC

Serving Clients Nationwide

Financial Advisor for entrepreneurs and professionals and their families.

Areas of Focus

  • Estate Planning
  • Financial Life Planning
  • Investment Management
  • Retirement Planning
  • Taxes

About Me

“Flip Flops and Pearls is bringing a methodology for helping people achieve lives of financial freedom, joy, and abundance to Charleston.”

Reggie Fairchild is a goal-driven entrepreneur with a passion for empowering others to achieve their own dreams. Reggie’s diverse experiences in innovation, finance and entrepreneurship led him to create Flip Flops and Pearls.

After leading several of America Online’s most successful product launches in the late 1990s, he relocated to Charleston in 2003 in order to campaign a sailboat. He raced in the 2005 Melges 24 World Champions and won the Corinthian National Championship in 2008.

Reggie went on to start up his own successful web design firm and co-found an innovative niche real estate company that became a top producer in its market. He has also served on the boards of several startups and non-profits. By combining these experiences with his strong commitment to client service, he’s able to provide exceptionally engaging financial guidance.

Reggie earned an MBA at Cornell University, and a BA in mathematics at Indiana’s DePauw University. He studied for his CERTIFIED FINANCIAL PLANNER™ certification at the University of Georgia Terry Business School. He is planning to sit for the exam later this year.

Married with three children, Reggie is a water sport aficionado. He continues to actively race sailboats. Together, he and his wife also work to protect the ocean and seashore environment. They champion sea turtles as well as helping to rescue other seashore animals. In 2019, Reggie was named the environmental steward of the year by Dewees Island.


  • Financial Planning Association
  • National Association of Personal Financial Advisors
  • XY Planning Network

Primary Location

1007 Johnnie Dodds Boulevard, Suite 135 Mount Pleasant, SC 29464

Meeting Options

  • Video Conference
  • In-Person
  • Phone

Compensation Methods

  • Fee Only

What to expect in the first meeting

Click the 'Book Intro Call' button above to schedule a free introductory call. We'll get to know each other and I'll listen to understand your unique circumstances so we can determine the best way to proceed. I look forward to speaking with you.

Offers Investment Management


About our Firm

Flip Flops and Pearls is a creative wealth management firm providing fee-only financial planning strategies to people who want to focus on maximizing their time and money. We can free up your time to focus on what matters to you, helping you prepare for the opportunities and challenges that will come your way.

We cater to entrepreneurs, consultants, and professionals from their working years up through retirement.

Our comprehensive wealth management system gives you a wide variety of tools you can use to set and prioritize your goals. We want to help you make your dreams a reality so you can spend your energy enjoying your life, your work, and your family.

Life has many twists and turns. Get ready for a great ride.


Cornell Johnson Graduate School of Management, Master of Business Administration (MBA) | DePauw University B.A., Mathematics, Physics (minor), Computer Science (minor)

Hobbies and Interests

  • Beach
  • Family
  • Sailing

Who We Serve

  • Baby Boomers
  • Business Owners
  • Corporate Executives
  • Dual Income Family
  • Entrepreneurs
  • Gen X
  • Living in Retirement

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