How to best protect your stock position?

Optimization. Prices a protective put, zero-cost collar, or put spread via Black-Scholes against implied volatility from a bundled option-market snapshot (a sector-typical volatility when the symbol is not covered); reports annual cost, max loss, upside cap, and bad-year coverage so you can pick the structure that fits your floor. For the put spread, the lower strike is solved so the chance of the stock ending below it over your expiration matches your chosen risk level (1 in 5 down to 1 in 100), using the implied volatility at that strike so the market’s own left-tail pricing sets the odds. The search is deterministic: the same inputs on the same date return the same answer, so the recommendation is verifiable.

Tax-code coverage. Relevant federal code (ordinary brackets, long-term capital gains, AMT with credit recovery, FICA, Net Investment Income Tax) plus all 50 states and DC for state ordinary brackets and LTCG treatment. State AMT modeled for CA, CO, CT, MN. Brackets reflect IRS Rev. Proc. 2025-32 and the One Big Beautiful Bill Act (OBBBA) provisions for tax year 2026. Validated against 870+ unit tests covering bracket math, AMT credit recovery, state conformity, and the optimizer's search path.

Why use an optimizer rather than asking an LLM to do the math: a benchmark of five frontier large language models on the same multi-year ISO problem found that all 15 trials overstated the after-tax result of their own proposed schedule by 2x to 20x (HackerNoon write-up).