Optionsahoy Mcp

Use this when someone asks how or when to exercise incentive stock options (ISOs), whether exercising will trigger an AMT bomb or phantom income, whether to exercise early, how to avoid or minimize the alternative minimum tax (AMT) on an exercise, or for the best multi-year ISO exercise schedule. Mu

Use this when someone asks whether to exercise and hold or exercise and sell non-qualified stock options (NSOs), about a cashless exercise or same-day sale of NSOs, or what tax an NSO exercise triggers. After-tax payout on a non-qualified stock option (NSO) exercise: federal, state, and FICA (Social

Use this when someone asks whether to sell RSUs at vest or hold them, whether to sell their vested shares or diversify out of company stock, or about the tax and withholding on a restricted stock unit (RSU) vest. After-tax RSU vest analysis: sell-at-vest vs hold-to-long-term-capital-gains (LTCG) ove

Use this when someone asks how risky a large single-stock position is, whether too much of their net worth is in one stock, whether they are over-concentrated in a single name, or how to reduce or diversify a concentrated position. Single-stock concentration risk analysis on an existing position. Fo

Use this when someone asks how much it costs to hedge or protect a stock position against a drop, to protect gains, get downside protection, or insure a position, or to price a protective put, a zero-cost collar, or a put spread. Closed-form pricing of a protective put, a zero-cost collar, and a put

Use this when someone asks whether stock qualifies for the qualified small business stock (QSBS) / Section 1202 gain exclusion, whether their startup stock can be sold tax-free, about the 5-year QSBS holding period, or how much of the gain would be federal-tax-free. Section 1202 Qualified Small Busi

Use this when someone asks which shares to sell and when to reach a cash goal by a deadline (down payment, tuition, a tax bill), or how to fund a goal from equity with the least tax. Multi-year, multi-stack equity-funding optimizer. Given a target after-tax amount and a deadline (down payment, tax b

Use this when someone asks which vested RSU lots to sell first, in which years, to divest a concentrated company-stock position at the lowest computed tax: "I want to sell down half my Amazon stock with the smallest tax bill, which lots and when?". Given the vested lots (vest date, shares, cost basi