Tax Planning
Forward-Looking Tax Planning for Retirees and High-Net-Worth Households
Tax planning at Compound Advisory is multi-year, IRMAA-aware, and integrated with retirement income, investment management, and estate decisions. We do not prepare returns — we plan around them.
Most households get tax advice at the wrong end of the year. By April, the only decisions left are the ones the IRS already lets you make. Real tax planning happens before December 31, ideally before October, and across a 10-to-20-year window — not one filing year at a time.
We coordinate Roth conversions, capital gain harvesting, charitable giving strategy, qualified charitable distributions (QCDs), Net Unrealized Appreciation (NUA) on company stock, business-exit structuring, and asset location across taxable, tax-deferred, and tax-free buckets. Each move is sized against your projected tax bracket, IRMAA exposure, RMD pressure, and estate plan.
What We Plan
- Roth conversion windows — how much, what year, at what marginal rate
- Capital gain harvesting and loss harvesting across tax years
- IRMAA bracket management (Medicare Part B & D premium planning)
- Qualified Charitable Distributions (QCDs) and Donor-Advised Funds (DAFs)
- Net Unrealized Appreciation (NUA) on employer stock
- Business owner exit structuring — installment sales, QSBS, asset vs. stock sales
- Asset location: which accounts hold which asset classes for maximum after-tax compounding
Coordination With Your CPA
We coordinate with your CPA or tax preparer. Most CPAs are excellent at preparing the return that already happened — our job is to plan the return that has not happened yet. The two roles complement each other and we encourage clients to keep both seats filled.
Each year we deliver a multi-year tax projection that lays out projected marginal brackets, IRMAA exposure two years ahead, Roth conversion capacity, and the recommended actions to take before year-end. We send the projection to your CPA in advance of fall planning meetings so the actual filing reflects the year that was planned, not just the year that was reported.
Why Multi-Year
Single-year tax decisions are the easy ones — and they leave most of the value on the table. The decisions that move the needle for retirees and high-net-worth households are 5-to-20-year decisions: how much Roth space to claim during low-income years before Social Security and RMDs, how much capital gain to realize before stepped-up basis dynamics shift, when to fund a Donor-Advised Fund to bunch deductions, and how to position assets across taxable, tax-deferred, and Roth buckets so the next decade of withdrawals lands in the most favorable place.
We model these decisions explicitly and we revisit the model every year. Tax law changes. Household income changes. Goals change. The plan changes with them.
Related Reading
Frequently Asked Questions
Do you prepare tax returns?
No. We are not a CPA firm. We plan around your tax situation across a multi-year window, and we coordinate the actual filing with your CPA or recommend one if you do not have a relationship.
What is IRMAA and why does it matter for retirees?
IRMAA is the Income-Related Monthly Adjustment Amount — the surcharge on Medicare Part B and Part D premiums when household income crosses certain thresholds. For 2026, the first threshold for single filers is around $109,000 of modified adjusted gross income. Crossing an IRMAA bracket by one dollar can cost thousands per person, per year, two years later. We plan around it explicitly.
When does a Roth conversion make sense?
When your current marginal tax rate is meaningfully lower than the rate you expect to pay (or your heirs expect to pay) on the same dollars later — and when you have non-IRA cash to pay the conversion tax. Early retirement years before Social Security and RMDs are often the best window. We size each conversion against your IRMAA bracket and your full multi-year plan.