A Private Briefing — Retired & Wealthy
The 7 Costly Tax Mistakes Wealthy Retirees Make —
And How to Avoid Every One of Them
A private briefing for financially successful individuals aged 50–70 with $500,000–$5,000,000+ in investable assets.
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Most wealthy retirees follow the same generic advice their broker gave them twenty years ago. That advice was not designed for someone with your level of assets — and in retirement, the cost of that mismatch compounds silently, year after year.
Required Minimum Distributions are not optional.
At 73, the IRS forces withdrawals from your tax-deferred accounts — pushing you into higher brackets and triggering Medicare surcharges you did not anticipate.
The window for Roth conversion is closing faster than you think.
The federal estate tax exemption is scheduled to drop sharply after 2025. Every year of inaction is a year of lost opportunity that cannot be recovered.
Your estate plan may be exposing your heirs to a 40% tax bill.
Assets you intend to pass on are quietly accumulating estate tax exposure. The tools to address this are legal, proven, and underused by anyone without a specialist advisor.
Inside the Guide
The RMD Bracket Trap
Why Required Minimum Distributions push high-asset retirees into tax brackets their working income never reached — and the precise strategies to reduce exposure before age 73.
The Roth Conversion Window
The specific income thresholds, timing conditions, and annual conversion amounts that maximise tax-free growth for your heirs without triggering IRMAA surcharges.
Social Security Taxation — The Hidden Formula
How provisional income quietly makes up to 85% of your Social Security benefit taxable — and the three income adjustments that change the calculation in your favour.
Capital Gains Timing Errors
Why selling the wrong assets in the wrong year can push long-term gains from 0% or 15% into 20% — plus the sequencing logic to avoid it.
The IRMAA Surcharge Blindspot
How a single large Roth conversion or asset sale triggers Medicare premium surcharges two years later — and the look-back mechanics most advisors fail to flag.
Estate Tax Exposure After 2025
The scheduled exemption drop, the structures that address it (GRATs, SLATs, FLPs), and the conditions under which each one is the correct tool.
The Step-Up Basis Mistake
Why gifting the wrong assets to heirs destroys one of the most valuable tax provisions in the code — and which assets should always be held until death.
You are between 50 and 70
The decade before and after retirement is when tax decisions have the highest leverage. The strategies in this guide require time — which you still have.
You have $500k–$5M+ in investable assets
Below this threshold, most of these issues do not apply. Above it, every year without a tax plan is a measurable and unnecessary loss.
You have been disappointed by generic advice
You have read the articles, attended the webinars, and received the boilerplate. This guide does not repeat that content. It starts where that content ends.
You intend to pass wealth to the next generation
Half of this guide addresses what happens to your assets after you. The decisions you make now determine whether your heirs inherit wealth — or a tax bill.
About the Writer
James R. Whitmore has spent over two decades advising financially successful individuals on the intersection of tax law and retirement strategy. His work has focused specifically on clients in the $500,000–$5,000,000+ asset range — the bracket where generic advice causes the most damage and specialist knowledge creates the most value.
He writes without the constraints of a broker-dealer compliance department or a firm with products to sell. What appears in his guides is what he has seen work — and what he has seen fail — across hundreds of real client situations over more than twenty years.
"The cost of a wrong decision at this level of wealth is not an abstract percentage. It is a number with commas in it."
Retired & Wealthy
25–40 pages. Private briefing format. Every strategy is specific, every mechanism explained, every condition stated. No padding. No generic advice. No free version of this exists.
$57
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