Hi, I'm Dre Griggs, CFP®
Founder of Obsidian Wisdom · Author of Wealthy Retirement Wisdom.
I help pre-retirees and business owners 45+ make tax-smart retirement decisions on purpose — using a seven-stage framework that places you exactly where you are, so you know what to focus on next.
- CERTIFIED FINANCIAL PLANNER™
- Economics Professor at St Johns River State College
- Author of Wealthy Retirement Wisdom — the foundation of how I think about retirement
- Host of Wealthy Retirement w/ Dre Griggs on YouTube
- Fee-only fiduciary — Florida Registered Investment Advisor
We ran through our savings. We racked up credit card debt. Eventually, we had to sell our home to make ends meet.
That experience taught me something most financial advisors learn from textbooks: the difference between knowing the math and living it.
I rebuilt. I went deep into financial planning. I earned my CFP® designation. I studied how the most resilient families actually accumulate, protect, and transfer wealth across generations. In 2024, I published Wealthy Retirement Wisdom — the book that captured the framework I had built up to that point: the three pillars of financial security, healthcare, and lifestyle.
But working with hundreds of pre-retirees taught me something the book couldn't capture by itself: most pre-retirees aren't failing because they lack a framework. They're failing because the tax code is designed to be confusing — and almost no one is teaching them how to navigate it deliberately.
The seven-stage framework Obsidian Wisdom is built around today is the answer to that gap. It evolved from the foundation in the book, but it's sharper, more actionable, and more diagnostic. Each stage has its own time-sensitive opportunities and its own costly mistakes. The whole point is to take retirement tax planning out of the dark and put it on a map.
That's the gap Obsidian Wisdom fills now.
THE PROBLEM
The retirement crisis is real, and it's not what most people think.
STRESS ABOUT MONEY
RETIRE W/out ENOUGH SAVED
LIVE PAYCHECK TO PAYCHECK
THE FRAMEWORK
The Seven Retirement Stages.
After years of working with pre-retirees, business owners, and retirees in every stage of life, I built the framework Obsidian Wisdom is now organized around. It's based on a simple observation: every pre-retiree is somewhere on a seven-stage journey, whether they know it or not.
Each stage has its own decisions, its own time-sensitive opportunities, and its own costly mistakes. The framework's whole purpose is to take the confusion of retirement tax planning and give you a place to stand.
Where you are determines what you should focus on.
Stage 1 (Build) requires different decisions than Stage 4 (Harvest). A Stage 6 retiree managing RMDs has nothing in common with a Stage 2 sheltering-stage builder.
The seven-stage framework is how we make the right work happen at the right time.
BUILD → SHELTER → CONVERT → HARVEST → COORDINATE → PROTECT → TRANSFER
Most clients enter our world by taking the Tax-Smart Retirement Stage Assessment. It takes less than 5 minutes. It places them precisely. From there, the right next step becomes obvious. Whether that's joining Portfolio Wisdom, booking a 1-Hour Financial Health Check, or engaging a full Wealthy Retirement Plan.
CREDENTIALS & BACKGROUND
Why I'm qualified to do this work.
CERTIFICATION
CERTIFIED FINANCIAL PLANNER™
The CFP® designation requires comprehensive education, a rigorous exam, multi-year experience requirements, and ongoing continuing education. It's the gold standard for fiduciary financial planning.
EDUCATION
Master's Degree in Economics
Graduate-level training in macroeconomic theory, monetary policy, and applied economic analysis. The analytical foundation behind tax-smart retirement strategy.
EXPERIENCE
Banking & Investment Management
Prior senior roles at Deutsche Bank (financial analysis), Wells Fargo (credit and budget analysis), and New York Life. The institutional experience that informs how I evaluate financial products and structures today.
REGULATORY
Registered Investment Advisor
Obsidian Wisdom is a state-registered fee-only RIA in Florida. As a fiduciary, I'm legally required to act in your best interest 100% of the time. No commissions, no product sales, no conflicts.
Where the work began.
PUBLISHED 2024 · AVAILABLE ON AMAZON
Wealthy Retirement Wisdom
My first book and the foundation of the work I do today. It introduces the Wealthy Retirement System. The three pillars of financial security, healthcare, and lifestyle that every retirement plan needs to address.
The seven-stage framework I now teach is the evolution of the work that started here. If you want to understand how I think about retirement before working with us, the book is the right place to start.
HOW I WORK
Three principles that guide every client engagement.
Clarity Before Strategy
Every engagement starts with knowing exactly where you are in the seven stages. Strategy without clarity is just guessing. And guessing wrong is expensive.
Fiduciary, Always
No commissions. No products designed by other firms. No conflicts. Your interests are legally required to come first, on every recommendation.
Honest About Limits
Some clients are well-served by self-managed approaches. Some don't need the highest tier. I'd rather tell you that than sell you something you don't need.
Beyond the work.
I'm a husband and father of four. I live in Fleming Island, Florida. The work I do at Obsidian Wisdom isn't separate from my life — it's directly connected to it. Everything I teach clients about wealth, time, and family came from rebuilding my own foundation after that first hard lesson.
When I'm not working with clients, you'll find me with my family, running our community, recording for the YouTube channel, or thinking through the next chapter of how this firm helps people retire well.
YOUTUBE
Wealthy Retirement w/ Dre Griggs
Weekly long-form content on tax-smart retirement, organized around the seven-stage framework. If you'd rather get to know how I think before reaching out, this is the best place to start.
Ready to find your stage?
The fastest way to know where you are is the assessment. Less than 5 minutes. Free. No commitment.
Copyright 2026 Obsidian Wisdom, LLC · Registered Investment Adviser in the state of Florida