Solutions
How we solve specific wealth problems.
A solution is a domain-specific bundle: a diagnostic that puts a number on the problem, a written plan, and the tax architecture required to execute it. Each one is built to answer one decision cleanly — not to be a general financial advisor.
Concentrated Stock
Diagnose a single-stock position in 2 minutes
Run the numbers on your concentrated equity, see the true tax cost of selling outright, and compare five strategies that defer or eliminate parts of the bill.
Open the diagnostic
Self-Employed Retirement
Shelter six figures a year as your own employer
When you own the business, you also control the retirement plan. Compare the SEP IRA, Solo 401(k), SIMPLE, and cash balance plans — and see how much each one shelters at your income.
Compare the plans
Equity & compensation guides
The tax mechanics behind RSUs, options, and employee stock — worked through with real numbers.
- Concentrated stock overviewThe whole problem in one place: risk, tax cost, and the five ways out.
- Stock-based compensationHow RSUs, ISOs, NSOs, and ESPP each create a different tax problem.
- RSU tax guideFederal, state, NIIT, and the supplemental-withholding gap, line by line.
- RSU sell vs. holdWhen holding vested RSUs is a concentrated bet you didn't mean to make.
- RSU withholding gapWhy 22% withholding leaves a balance due — and how to size the shortfall.
- RSUs in CaliforniaState sourcing, the 10.3%+ rate stack, and moves before you exercise or sell.
- ISO vs. NSOWhich option type triggers AMT vs. ordinary income, and when each is worth it.
- ESPP taxQualifying vs. disqualifying dispositions and the discount that gets taxed twice.
- ESPP disqualifying dispositionWhat an early sale costs and when it's still the right call.
- Career arc guideSequencing 83(b), ISOs, and QSBS across the stages of a tech career.
- QSBS (Section 1202)Up to $10M (or 10×) of gain excluded — the holding-period and eligibility rules.
Tax strategies
The vehicles that defer, offset, or eliminate the gain on a concentrated position.
- Section 351 ETF exchangeContribute low-basis stock into a new ETF — diversify without a sale.
- Exchange fundsSection 721 partnerships: immediate diversification with a seven-year lockup.
- Direct indexingRebuild the index directly and harvest losses to offset future gains.
- Long/shortA 130/30-style sleeve that builds a loss reservoir against your sale.
- Charitable remainder trustTax-free sale inside a Section 664 trust, with income spread over decades.
- 10b5-1 plansThe pre-set sale schedule insiders use to trade through blackout windows.
- Strategy comparisonSide by side: cost, lockup, harvested-loss capacity, and charitable fit.
Self-employed retirement
Picking and stacking the right plan when you're both the employer and the employee.
- SEP IRA vs. Solo 401(k)Same $72,000 ceiling, very different paths to it — and why the Solo 401(k) usually wins.
- SEP IRA vs. SIMPLE IRALower-cost SIMPLE vs. higher-ceiling SEP, sorted by income and headcount.
- SIMPLE IRA vs. safe-harbor 401(k)When a SIMPLE caps out and a safe-harbor 401(k) is worth the extra admin.
- Solo 401(k) contribution limitsThe 2026 employee, employer, and catch-up limits for a one-person 401(k).
- Cash balance plansThe defined-benefit plan that lets a high earner shelter $200k+ a year.
- Cash balance plan + 401(k)Stacking a cash balance plan on a 401(k) for a combined deduction.
- Retirement plan for S-corp ownersHow an S-corp owner's W-2 salary sets the contribution math.
Case studies
How the pieces fit together for a real situation.
Who we work with
Most of the book is senior tech operators and founders.
More solutions in development. If you have a wealth problem that isn't listed here, email Sumeet directly.