Five gold stars followed by a green checkmark and text: 22 Certified Advisor Reviews.

Flat-Fee Financial Planner in Florida

Personalized financial strategies for the life you’ve earned

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2025 Wealthtender Voice of the Client Award™

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"Chris made financial planning feel approachable and personal for both me and my wife. He listened closely, understood what mattered most to us, and delivered a clear, customized roadmap we could follow. His flat-fee structure gave us peace of mind, and we always felt he was in our corner, not selling, just advising...."
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Common questions we help answer

Planning for retirement in Florida comes with unique moving parts, from taxes and healthcare to income planning and protecting your lifestyle. We help future and current retirees across Florida answer the financial questions that matter most so they can retire with more confidence and a plan built for long-term peace of mind.

We take a different approach to retirement

Spending answers, tax analysis, stress testing, Social Security optimization, and more

The Old Way
  • You have a 85% probability of success in retirement
  • This is how much you can spend based on the “4% Rule”
  • Delay your Social Security claiming until you are 70 years old
  • You need an annuity to protect your retirement income
  • Talk to your tax professional because we can’t provide tax advice
The Southshore Way
  • Here is your spending capacity on day one of retirement
  • Your plan factoring in your “go-go, slow-go, and no-go” phases
  • Here is your personalized Social Security claiming strategy
  • Backtest your plan against some of the worst times in history
  • Here are three ways to lower your lifetime tax bill
"...After researching several options, I chose Chris Shoup at Southshore Financial Planning largely because of his transparent and reasonable fee structure. Chris did an exceptionally thorough job analyzing my full financial picture. He uses a very organized, step-by-step planning process that includes a series of focused meetings, which allowed us to thoughtfully build a plan together..."
What We Don't Do
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Sell annuities or insurance products
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Act as a brokerage or bank company
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Require our clients to have us manage investments
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Require us to replace other financial professionals
Have minimum assets or account values
What We Do
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Help you create a plan for retirement
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Give advice without product sales or commissions
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Serve as your partner, not a brokerage platform
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Coordinate with your accountant & other trusted professionals
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Work with clients based on fit & goals, not assets

Our 7-Point Retirement System

Before looking at a single number, we focus entirely on the life you want to build. We help you map out your retirement "must-haves" alongside those big, exciting bucket-list dreams. Together, we use these personal aspirations to design a customized roadmap.

Common Questions We Answer:

How do I transition mentally from a lifetime of aggressive saving to suddenly relaxing and enjoying my life?
How do I balance my immediate bucket-list dreams with my long-term financial security?
How do I reconcile different retirement goals with my spouse?

Transitioning from saving money to spending it can be one of the most stressful phases of retirement. We help you build a reliable "retirement paycheck" that you are comfortable with. Our dynamic plan is structured to prevent both overspending and underspending, letting you confidently enjoy life to the fullest.

Common Questions We Answer:

Where exactly will my monthly income come from once my salary stops?
How will my income plan adapt if the stock market goes through a sudden downturn?
When is the most optimal and tax-efficient time for me to claim Social Security?

Taxes will likely represent one of your single largest expenses throughout your retirement years. Unlike traditional tax preparation that only looks backward at last year, our planning proactively focuses on forward-looking strategies. We look for smart opportunities to minimize your total lifetime tax liability so you keep more of your wealth.

Common Questions We Answer:

How can I lower the taxes I pay when withdrawing from my IRAs or 401(k)s?
Does it make sense for me to do Roth IRA conversions, and if so, when?
How will my retirement income level impact my Medicare premiums (IRMAA)?

Health care is often the single largest wildcard and a confusing aspect of retirement, which is why we model health care and long-term care expenses directly into your plan. We also have partners who can assist with bridging the pre-Medicare health insurance gap, enrolling in Medicare, or selecting optimal supplemental policies.

Common Questions We Answer:

What are my health insurance options if I want to retire before Medicare starts?
Will I be automatically enrolled in Medicare when I turn 65?
Is Long-Term Care Insurance (LTCI) actually worth the premiums, or is it better to self-insure?

We believe in designing evidence-based portfolios tailored to your financial goals. By educating you on how different market climates impact investments, we establish an asset mix that balances your personal risk tolerance with your retirement needs. From there, we manage or recommend investments across all your accounts to keep you aligned with your long-term plan.

Common Questions We Answer:

Is my current investment portfolio too risky—or too conservative—for retirement?
How do I transition my portfolio from a "growth" focus to a reliable "income" focus?
How do I protect my portfolio from Sequence of Returns Risk?

As a fee-only advisory firm, we do not sell insurance products or earn commissions from referrals. This independence allows us to provide an entirely unbiased, professional review of your existing insurance coverage. We identify potential gaps and give you a clear checklist to review with your agent.

Common Questions We Answer:

Am I currently overpaying for insurance coverage I no longer need in retirement?
Do I have any hidden gaps in my homeowners or auto policies?
Do I need an Umbrella Liability Policy in retirement?

A great estate plan ensures your wishes, your care, and your legacy are fully protected if you cannot make decisions yourself. We review your current wills, trusts, and power of attorney documents to ensure they align with your actual goals. If your plan needs to be created or updated, we connect you with trusted estate attorneys or services to complete the process.

Common Questions We Answer:

Who will handle my financial and medical decisions if I suddenly become incapacitated?
How do I prevent my heirs from going through the complex, costly, and public probate court process?
What happens to my Traditional and Roth IRAs when I leave them to my heirs?
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Don't live in Florida? Don't worry. We can still help.

While many of our clients (and myself) call Florida home, we work with families nationwide and have built a seamless virtual experience that makes it easy to get expert guidance wherever you are. Same advice, same attention, just delivered remotely.

Working Together

Our process is designed to simplify every aspect of your financial life, bringing your investments, taxes, cash flow, and long-term goals into one cohesive strategy. With everything aligned, you can make decisions with purpose and move forward knowing you have a clear plan and a trusted partner guiding you along the way. Have more questions? Check out our FAQ page here:

Step 1
Discovery Call

This 30-minute call is to discuss your goals and determine if our firm is a good fit. You'll learn about our financial planning process, how we manage investment portfolios, our fee structure, and get all your questions answered.

Step 2
Our Analysis

Once you’ve decided to move forward, we'll collect your data and begin to map every aspect of your financial life: investments, liabilities, cash flow, taxes, insurance, and estate planning.

Step 3
Implementation

We provide a comprehensive plan with specific recommendations on how to achieve your retirement goals. We'll also present a portfolio analysis with suggestions to better align your investments.

Step 4
Ongoing Partnership

Regular meeting and ongoing guidance. Strategy adjustments as life changes. Unlimited questions answered. All for a transparent annual fee that never increases with your wealth.

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January
Tax summary letter provided to your CPA
Spring Update Meeting
Tax planning (review prior year tax return and discuss opportunities for the current year) and focused investment portfolio review
Summer
Check-in as needed
Fall Update Meeting
Comprehensive financial plan update. Review tax planning opportunities before year-end