Episode 43 of Retirement Tax Matters addresses the technical and psychological hurdles that high-net-worth retirees between $2M-$8M face when managing highly appreciated, taxable brokerage accounts. Learn how to think through a systematic, multi-year transition strategy to diversify away from concentrated stock risk without triggering a tax surprise the following April.

Episode 40 of Retirement Tax Matters breaks down the mechanics of using a Donor-Advised Fund to help lessen capital gains taxes and the 3.8% Net Investment Income Tax on highly appreciated brokerage assets. Transferring low-basis stock directly into a DAF allows savers within the $2M–$8M range to claim a charitable deduction while legally erasing some of the embedded tax debt.