Whether you're a former tech exec sitting on $5M of post-exit liquidity, a current SVP planning for a sabbatical-then-board-roles transition, or a founder who just took chips off the table — your highest-leverage tax-planning years aren't behind you. They're now. And they're invisible to the wirehouse advisor whose product menu doesn't include "do less stuff better."
This is the Good Deals playbook for executives who built it themselves and want to keep it that way.
The financial decisions that mattered during your career — 401(k) contribution rate, RSU vest schedule, IPO trading window — are mostly behind you. The decisions ahead are different. They're about structure, sequencing, and tax-character management. They compound just as silently as the earlier ones did, but in the opposite direction if you ignore them.
Most executives leave with single-stock concentration. Diversifying generates capital gains. Charitable giving via DAFs, exchange funds, and SLAT/GRAT structures can move concentrated positions out of your estate without triggering full gain recognition — but only if structured correctly and before liquidity events.
Between your last wage year and age 73, you sit in a much lower marginal bracket than you did at peak earnings — and lower than you'll face once RMDs force income at 73. Roth conversions during this window are the single highest-leverage move for most executives with $1M+ pre-tax balances.
The federal estate tax exemption sunsets in 2026 ($13.99M → ~$7M per person). Executives with $10M+ net worth who don't plan ahead will face 40% federal estate tax on every dollar above the new exemption. The planning window to lock in the higher exemption is now.
Six calculators that map the highest-leverage decisions for HNW executives in the post-accumulation decade. All free. All cite their sources to IRS / Cornell LII / SSA.
Project lifetime tax savings of converting Traditional → Roth strategically during the post-employment window. For $2M+ pre-tax balances the math is often six figures.
Run the calculator → NewMedicare premium surcharges quietly cost most HNW retirees $5K-$12K/yr. See your tier and the cliff distances. 2026 estimated.
Run the calculator → NewFor $3M+ Traditional balances, RMDs alone push you back into 32-37% bracket. See year-by-year through age 95 with IRS Uniform Lifetime Table.
Run the calculator → AuditThat "free" company 401(k)? Expense ratios + recordkeeping + advisory fees often run 0.5-1.2%. On a $3M balance over 20 years that's $500K+ in fee drag.
Run the calculator → Pre-exitWhile still working: most pre-exit executives in 32-37% benefit from Traditional today. Crossover happens once you can project your retirement window bracket below 24%.
Run the calculator → GovernanceInvestment Policy Statement — the document that governs how your money is managed. The constitution of your portfolio. Most executives don't have one. They should.
Build your IPS →Modeled examples, not historical client outcomes. The figures below are projections built from the same source-cited math the calculators run, applied to representative executive situations. Your numbers will differ based on your specific equity, basis, brackets, state, and timing.
A hypothetical tech VP retiring Q4 2024 after a sale. Post-tax proceeds: $4.8M cash + $3.6M in former-employer stock (taxable, low basis). Plus $2.1M in 401(k)/IRA balances.
A 4-track plan modeled here: (1) systematic concentration unwind over 6 years using charitable DAF for top-of-basis lots + tax-loss harvesting on the cash side to offset gains, (2) annual Roth conversions filling 24% bracket from 58-72, (3) deferred Social Security to 70 for the 8% delayed credit, (4) GST trust for the lower-basis portion to lock in the estate exemption pre-sunset.
A hypothetical software-engineering SVP at a public company, planning to leave Q3 2026 and relocate to Austin. Annual RSU vests of $850K at 37%+ effective federal in CA, 13.3% CA state tax on top — total marginal ~50%. Decision point: accelerate or defer the planned exit by 2 quarters?
The modeled residency timing: establishing TX residency before the Q4 2026 vest (the largest of the cycle) shifts ~$1.6M of taxable comp from CA-source to TX-source. State-tax savings on the timing alone: ~$210K. Combined with optimal exercise of NQSOs in the residency-transition year and a $250K mega-backdoor Roth via the company plan during 2026 plan year.
| Approach | Typical wirehouse / private bank | Robo / DIY | Good Deals |
|---|---|---|---|
| Source-cited modeling | "Trust me" + glossy brochure | FAQ articles + calculator widgets | Every claim links to IRS / Cornell LII / SSA. You can verify. |
| Compensation model | Commissions + AUM + product spreads | Self-serve fees | Flat-fee engagement + transparent AUM. No product commissions. |
| Custody | Proprietary platform with lockup risk | Proprietary platform | Altruist (modern independent) — you own the account, you can leave anytime |
| Tax-strategy depth | "Talk to your CPA" | None | CFA-grade modeling: Roth ladder, IRMAA, RMD, estate, concentration unwind |
| Account minimum | Typically $2M-$5M | $0 | $500 Foundation Review entry. No AUM minimum to engage. |
90 minutes with Andrew + a written report walking your specific situation against the full executive playbook. Roth Conversion Ladder, IRMAA management, RMD projection, concentration unwind, estate-tax exposure, charitable strategy, Social Security claiming.
The deal: If we don't surface at least $5,000 of structural annual or one-time savings during the session, your $500 is refunded in full and you keep the written report.
Book the Foundation Review →$500 · 90 minutes · Credited toward an engagement if we work together. Refunded if not a fit.
The Executive Tax + Estate Playbook PDF covers the full sequence: Roth Conversion Ladder math, IRMAA cliffs, RMD projection, concentration unwind via DAF and exchange funds, estate-tax exemption planning before the 2026 sunset, and Social Security claiming. Free. We email it.
Most executives don't need to leave their private bank — they need a second opinion from an advisor with no conflict of interest. The Foundation Review is structured exactly that way. An independent CFA Charterholder walks your situation, surfaces what's under-modeled or commission-driven in the existing setup, and gives you a written report. If your private bank is doing the math well, the report will reflect that. If there's $50K-$200K of tax-strategy savings being left on the table, you'll know it — with citations.
No. Three options: (1) $500 Foundation Review — one-time, paid upfront, $5K-savings guarantee. (2) $5K-$10K Engagement — flat fee for the full Financial Snapshot + Investment Policy Statement + FutureGuide + 90-day implementation support. (3) Ongoing Advisory at 100 bps of AUM, optional, only if you want us managing assets via Altruist. The flat-fee engagement stands alone — you don't need to put assets under management to work with us.
Yes — RSU vest schedules, NQSO/ISO exercise strategy, 10b5-1 plans, post-IPO trading windows, and concentration-unwind structures (DAF, exchange funds, charitable trusts) are core to the executive playbook. The math gets specific to the company, the position, and the proximity to liquidity events. The Foundation Review surfaces the most material decisions; engagement work executes them.
We coordinate but don't draft. The federal estate-tax exemption sunsets at end of 2025 (currently $13.99M / person; reverts to ~$7M unless Congress acts). For executives with $10M+ net worth, the planning window to lock in the higher exemption via SLAT, GST trust, or other structures is NOW. We model the trade-offs and project the savings; estate-attorney drafts the documents.
Currently registered as an Investment Adviser Representative in Texas. We can engage with clients in other states through the de minimis exemption (limited number of clients per state) and add registrations as engagements clarify which states matter. Compliance is real — we don't operate where we're not registered.
Most executives prefer to start with a brief no-pitch conversation. Free 15-minute Discovery Call — we talk through your situation, you ask the hard questions, and we decide together if the Foundation Review makes sense.
Book a free 15-min call →Good Deals is the planning workbook + advisory practice of Andrew Escher, based in Austin, TX. Independent stack: Altruist for investment custody, BackNine for insurance placement, Good Deals for the planning layer that ties them together. We work specifically with HNW executives, pre-retirees, and business owners on structural tax + estate planning. No product commissions, no proprietary funds, no hidden incentives.