Financial Decisions That Deserve Tax Planning First

ISO vs NSO, AMT exposure, cash needed for taxes, holding period to qualify for capital gains — all of it has to be modeled before you exercise, not after.

Section 121 exclusion ($250K single / $500K joint) requires meeting use and ownership tests. Timing the sale around qualifying can save six figures.

Asset vs. stock sale, allocation of purchase price, installment sale, QSBS exclusion eligibility — each lever can shift the tax bill by hundreds of thousands. Diligence is too late to optimize them.

Inherited assets generally get a basis step-up to date-of-death FMV. Selling immediately uses the step-up; gifting before death does not. The right answer depends on the asset, the holding period, and the recipient's situation.

Size, timing, source of tax payment, and multi-year planning all matter. A poorly sized conversion can cost more than it saves over a lifetime.

Cash, appreciated stock, donor-advised funds, charitable remainder trusts — each produces different deductions and different long-term outcomes. The vehicle matters as much as the amount.