Henry Supinski, ChFC®
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4 min read
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April 2026
The Social Security Decision Most People Get Wrong, and How It Costs Them $100,000
When to claim Social Security is one of the most consequential financial decisions you'll make in retirement. Yet most people spend less than an hour on it. Here's what the research actually says, and why waiting usually wins.
Read Article →The Roth Conversion Window: Why the Years Before 73 Are So Valuable
The gap between retirement and your first RMD may be the greatest tax planning opportunity of your life.
Henry Supinski · April 2026 · 4 min read
Your RSUs Are Vesting. Here's What to Do Next.
Most tech employees have no plan for their vesting RSUs. Here's a simple framework, before the tax bill arrives.
Henry Supinski · April 2026 · 4 min read
What "Fee-Only" and "Fiduciary" Actually Mean, and Why It Matters
These are two of the most important (and most misunderstood) terms in financial services. Here's the plain-English version.
Henry Supinski · April 2026 · 4 min read
Downsizing in Retirement: The Money Side and the Home Side
Selling the family home is two projects at once. Written with home transition specialist Lois Volta.
Henry Supinski with Lois Volta · August 2026 · 9 min read
Does Delaware Have an Inheritance Tax? No. Here Is What That Actually Means
Delaware has no inheritance tax and no estate tax.
Henry Supinski · August 2026 · 4 min read
Pennsylvania Inheritance Tax: What Your Kids Actually Pay on the IRA, the House, and the Life Insurance
Pennsylvania taxes inheritances from the first dollar, but not every asset is treated the same.
Henry Supinski · August 2026 · 5 min read
You Inherited an IRA. Here Is the 10-Year Rule, and the Mistake That Costs the Most.
Most non-spouse heirs must empty an inherited IRA within ten years, and since 2025 many must also take annual withdrawals along the way.
Henry Supinski · August 2026 · 5 min read
Net Unrealized Appreciation: The 401(k) Company Stock Move Most People Miss
If you hold company stock inside your 401(k), rolling it into an IRA at retirement can be a costly default.
Henry Supinski · August 2026 · 5 min read
Turning 65 and Still Working: What to Do About Medicare When You Have Employer Coverage
You can delay Medicare Part B without penalty if you have coverage from a current employer with 20 or more employees.
Henry Supinski · August 2026 · 5 min read
Deferred Compensation: The Payout Election to Find Before You Leave Your Job
Nonqualified deferred compensation pays out on a schedule you chose years ago, and separation from service usually triggers it whether you are ready or not.
Henry Supinski · August 2026 · 5 min read
How IRMAA Quietly Increases Retirement Costs
Medicare surcharges can be a costly surprise for high earners. Most people don't see it coming.
Henry Supinski · April 2026 · 4 min read
Sequence of Returns Risk: The Retirement Danger No One Talks About
One bad year early in retirement can permanently alter your financial trajectory. Here's how to think about it.
Ron Madey · April 2026 · 4 min read
The Hidden Cost of Uncoordinated Financial Advice
When your investment manager, tax advisor, and planner aren't talking to each other, the gaps between them cost you.
Henry Supinski · April 2026 · 4 min read
Beneficiary Designations vs. Your Will: Which One Actually Wins?
Your IRA, 401(k), and life insurance pass outside of probate. Beneficiary designations often override what your will says.
Henry Supinski · April 2026 · 5 min read
Retiring in Delaware: What the State Does and Doesn't Tax
No sales tax, no inheritance tax, untaxed Social Security, and a $12,500 exclusion. Here's how the pieces fit together.
Henry Supinski · July 2026 · 4 min read
Retiring in Delaware vs. Pennsylvania: Where the Taxes Actually Differ
PA generally exempts qualifying retirement income. DE has no sales, estate, or inheritance tax. Which side of the line fits your retirement?
Henry Supinski · July 2026 · 5 min read
How to Change Your Domicile from Pennsylvania to Delaware
Domicile is a fact pattern, not a mailing address. The checklist that holds up in a residency audit, and the mistakes that unwind it.
Henry Supinski · July 2026 · 5 min read
You Vested a Fortune in One Stock. Now What?
Concentration builds one vest at a time. Here's how to think about reducing it without a rushed, tax-inefficient sale.
Henry Supinski · July 2026 · 4 min read
10b5-1 Plans: Selling Company Stock Without Second-Guessing Yourself
A pre-set trading plan removes the timing anxiety from selling concentrated stock. Here's how they work, and who actually needs one.
Henry Supinski · July 2026 · 4 min read
ISOs, NSOs, and RSUs: The Tax Rules Nobody Explains Clearly
Three types of equity compensation, three completely different tax treatments. The plain-English breakdown, including the ISO/AMT trap.
Henry Supinski · July 2026 · 4 min read
You Got a Severance Package. Here's Your First 90 Days.
A first-90-days plan for health coverage, cash flow, and the equity deadlines that sneak up faster than you'd expect.
Henry Supinski · July 2026 · 4 min read
The Backdoor Roth: What It Is and Who Actually Needs One
Roth IRA income limits shut most high earners out. Here's the legal workaround, and the pro-rata rule that trips people up.
Henry Supinski · July 2026 · 4 min read
Why Your RSU Tax Withholding Is Probably Wrong
The flat withholding rate on vesting RSUs is rarely your real tax rate. Here's why that gap becomes a surprise bill in April.
Henry Supinski · July 2026 · 4 min read
Delaware or Pennsylvania: Which State Treats Your Estate Better?
PA taxes inheritances based on who receives them. DE taxes neither estates nor inheritances. How the two states actually compare.
Henry Supinski · July 2026 · 4 min read
Divorce and Equity Compensation: What Gets Split, and How
Unvested RSUs and options don't follow the usual rules. What counts as marital property, and why a QDRO doesn't apply.
Henry Supinski · July 2026 · 4 min read