Reggie Fairchild, CFP®

Charleston Based Financial Planner for Entrepreneurs & Professionals

Connect Cancel

Wealthtender Community Connect helps people discover the best financial advisors for their individual needs through their favorite blogs and podcasts.

Click Here to Learn More
Contact Me
Flip Flops and Pearls Reggie Fairchild, CFP®
Mount Pleasant, SC

Serving Clients Nationwide

Charleston Based Financial Planner for Entrepreneurs & Professionals

Areas of Focus

  • Estate Planning
  • Financial Life Planning
  • Investment Management
  • Owning a Business
  • Retirement Planning
  • Taxes

About Reggie Fairchild, CFP®

I’m Reggie Fairchild, CFP®, founder of Flip Flops and Pearls, a Charleston-based financial planning firm dedicated to helping high-achieving professionals align their wealth with what matters most.

Before becoming a financial advisor, I followed my passion and curiosity through a range of entrepreneurial adventures and high-growth companies. In the early days of the internet, I helped lead some of AOL’s (America Online’s) most innovative and successful product launches. Later, I built a web design business, co-founded a real estate firm, and had the chance to support a number of startups and nonprofits along the way. Whether serving on a board or in an advisory role, I bring thoughtful strategy and genuine enthusiasm to every venture.

In 2003, I left the D.C. pace behind and moved to Charleston to enjoy the Lowcountry’s natural beauty, welcoming community, and amazing outdoor lifestyle. That decision reshaped how I thought about time, values, and opportunities.

Today, I bring that same energy and creativity to my work as a financial advisor. I’m passionate about helping clients find clarity and confidence in their financial lives—whether it’s through long-term retirement planning, tax optimization, or simply figuring out how to live more fully right now. My planning philosophy revolves around enjoying life today and while preparing confidently for tomorrow. Financial planning is not about sacrifice, it’s about possibility.

Outside of work, I’m a husband and father of three, with a deep appreciation for the simple, meaningful moments I’ve shared with my family—often outdoors, surrounded by the beauty of the Lowcountry and the world. I’m also an avid sailor and continue to race sailboats around the Southeast.

I hold the CERTIFIED FINANCIAL PLANNER™ designation, an MBA from Cornell University, and a BA in Mathematics from DePauw University.

Professional Designations

  • CERTIFIED FINANCIAL PLANNER ®

Affiliations

  • 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 complimentary first conversation. We’ll take time to get to know each other, talk through what’s on your mind, and explore how we might support your financial life—on your terms and timeline. No pressure. Just a thoughtful starting point. And if we’re not the right fit? We’ll do our best to point you in the direction of someone who is. Looking forward to meeting you.

Offers Investment Management

Yes

About Flip Flops and Pearls

Flip Flops and Pearls is a fee-only financial planning firm dedicated to helping individuals and families maximize their time and wealth, all while living their best lives. We know that money isn’t just about numbers—it’s about making room for what matters most in your life.

We understand working professionals are busy people. We know you want to live your best life today while planning for tomorrow. We are here for you, we work only for you, and we don't take commissions for any solution we recommend.

At Flip Flops and Pearls, we focus on more than just financial strategy. Our comprehensive wealth management system equips you with the tools and guidance to confidently set, prioritize, and achieve your goals—while ensuring your time and energy are spent on the things you love: whether that’s family, work, or the lifestyle you’ve always dreamed of.

Life is full of opportunities and challenges. Our goal is to help you navigate those twists and turns with intention, clarity and confidence, so you can truly enjoy the ride.

Education

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
  • Photography
  • Sailing

Who We Serve

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

To make Wealthtender free for readers, we earn a nominal monthly fee from financial advisors and firms in exchange for marketing services (including being featured on this profile page), subject to terms of use. This compensation creates a natural conflict of interest when we favor their promotion over others. Wealthtender is not a client of these advisors or firms. Testimonials may not be representative of other clients’ experiences and do not guarantee future performance or success.