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Good Plans. Great Adventures.

Work With Us

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FAQ

Book a Call

Your Future is Waiting.

Q: What’s the difference between financial planning, investment design, and wealth management?

Financial planning connects your goals, cash flow, taxes, retirement, risk, and estate decisions into one plan. Investment management focuses on building and maintaining your portfolio. Wealth management often combines both, plus coordination with your CPA and attorney when life is more complex.

Q: How do I know if I’m on track financially for my goals?

We translate your goals into real numbers and test your plan under a few realistic scenarios. If you’re close but not quite there, we’ll show clear, practical steps to strengthen it. You’re on track when you can enjoy today and still feel confident about the future.

Q: How should I pay myself as a business owner—salary, distributions, or both?

The right mix depends on your business structure, cash flow, and tax considerations. We coordinate with your CPA to create a strategy that supports both your personal plan and business health.

Q: How do I balance saving for the future with enjoying life today?

Pay yourself, and your future self, first by automating the essentials like retirement savings and key goals. Once that’s done, you can spend the rest in whatever way you choose with far less guilt or second-guessing. The plan gives you permission to enjoy life.

Q: What does a typical first meeting look like?

Your first meeting is an introductory conversation. We’ll get to know your situation at a high level, what you’re looking for, and what feels most important right now. We’ll also explain how we work, how our fees work, and we’ll both assess whether it’s a good fit. If you decide to move forward, the next step is a deeper planning meeting where we gather documents, ask more detailed questions, and start building the plan.

Q: How often should I review or update my financial plan?

At least annually, and anytime life changes: a new role, equity event, move, business milestone, inheritance, or retirement decision. Small updates along the way prevent big surprises later.

Q: What retirement plan options are available for small business owners?

SEP IRAs, SIMPLE IRAs, and Solo 401(k)s are common options with different rules and contribution limits. The right choice depends on income, employees, and flexibility needs. We’ll match the plan to your goals and coordinate with your CPA.

Let's Get to Work.

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How We Work

5

Years in Business

5

Years in Business

5

Years in Business

100%

Fee Only Planning

100%

Fee Only Planning

100%

Fee Only Planning

1.7M+

Typical Client Networth

1.7M+

Typical Client Networth

1.7M+

Typical Client Networth

40%

Clients Served Remotely

40%

Clients Served Remotely

40%

Clients Served Remotely

You're Ready. Let's build the plan.

See if We Are a Fit

Learn what working together looks like and if it’s right for you.

You've already done the hard part.

Our role is to help bring order to the moving pieces, protect what you’ve earned, and shape a plan that fits your life.

You’re not starting from scratch. You’re leveling up.

Would highly recommend Flip Flops and Pearls Financial Planning. Great people to have supporting you with your future.

The testimonials presented on this website were provided by current clients of Flip Flops and Pearls, LLC at the time of the testimonial. Clients did not receive compensation for their testimonials, and we are not aware of any material conflicts of interest related to these statements. These reviews may be truncated for display purposes. All full client testimonials are publicly available on Wealthtender.com.

Our path to your plan.

Step Lightly. Live Well.™

Process

Explore Meeting

A relaxed first call to understand your goals and see if we’re a fit.

Book Intro Call

Get Started

You decide to work with us. We formalize the relationship and get started.

Initial Review

We look at your current financial picture and identify where we can help.

Planning

We take a deep dive into your income, taxes, investments, risks and goals.

Activation

Your plan moves into action—we help coordinate across all areas.

Ongoing Partnership

We continue refining your plan as life evolves, with regular check-ins.

A close-up of a person’s hand gripping the throttle of a motorboat at sunrise, with calm water and a distant boat softly blurred in the background.

Explore Meeting

A relaxed first call to understand your goals and see if we’re a fit.

Book Intro Call

Get Started

You decide to work with us. We formalize the relationship and get started.

Initial Review

We look at your current financial picture and identify where we can help.

Planning

We take a deep dive into your income, taxes, investments, risks and goals.

Activation

Your plan moves into action—we help coordinate across all areas.

Ongoing Partnership

We continue refining your plan as life evolves, with regular check-ins.

Explore Meeting

A relaxed first call to understand your goals and see if we’re a fit.

Book Intro Call

Get Started

You decide to work with us. We formalize the relationship and get started.

Initial Review

We look at your current financial picture and identify where we can help.

Planning

We take a deep dive into your income, taxes, investments, risks and goals.

Activation

Your plan moves into action—we help coordinate across all areas.

Ongoing Partnership

We continue refining your plan as life evolves, with regular check-ins.

A Thoughtful Partner for What’s Next

You’ve built a lot. We'll help you protect it and plan ahead with confidence.

Get Started Today

A Thoughtful Partner for What’s Next

You’ve built a lot. We'll help you protect it and plan ahead with confidence.

Get Started Today

Why Choose Us?

Financial planning that’s simple, human, and designed to align your money with the life you want to live.

Advice Tailored to You

Your plan starts with your life—not a template. We build around your goals, values, and the way you actually work and live, then help you follow through as things change.

Advice Tailored to You

Your plan starts with your life—not a template. We build around your goals, values, and the way you actually work and live, then help you follow through as things change.

Advice Tailored to You

Your plan starts with your life—not a template. We build around your goals, values, and the way you actually work and live, then help you follow through as things change.

Real-World Perspective

We help with the big moments—career growth, business decisions, family changes, and retirement. The goal: enjoy life today and build a plan for the Charleston lifestyle you love.

Real-World Perspective

We help with the big moments—career growth, business decisions, family changes, and retirement. The goal: enjoy life today and build a plan for the Charleston lifestyle you love.

Real-World Perspective

We help with the big moments—career growth, business decisions, family changes, and retirement. The goal: enjoy life today and build a plan for the Charleston lifestyle you love.

A Partner You Can Trust

Long-term relationships, not transactions. You pay us directly, so our advice stays plan-driven and straightforward. When life changes, you’ll have a steady partner to talk it through.

A Partner You Can Trust

Long-term relationships, not transactions. You pay us directly, so our advice stays plan-driven and straightforward. When life changes, you’ll have a steady partner to talk it through.

A Partner You Can Trust

Long-term relationships, not transactions. You pay us directly, so our advice stays plan-driven and straightforward. When life changes, you’ll have a steady partner to talk it through.

Wealth Strategy
Wealth Strategy
Wealth Strategy
Tax Aware Planning
Tax Aware Planning
Tax Aware Planning
Liquidity Strategy
Liquidity Strategy
Liquidity Strategy
Portfolio Management
Portfolio Management
Portfolio Management

Equity Compensation
Equity Compensation
Equity Compensation
Estate Strategy
Estate Strategy
Estate Strategy
Cash-Flow Strategy
Cash-Flow Strategy
Cash-Flow Strategy
Retirement Optimization
Retirement Optimization
Retirement Optimization

Meet Your Lead Advisor

Reggie Fairchild, CFP®

President / Chief Advisor

I help Charleston professionals and business owners make thoughtful financial decisions without unnecessary stress.

You’ll get clear, practical guidance and proactive follow-through—built around how you actually work and live.

Charleston has been home for nearly 23 years, and I’ve built deep community roots and local know-how across the Coastal Southeast. Many clients work with me remotely, too, with the same goal: plans that support life here and the adventures ahead.

Meet With Reggie