# Why a Multi-Year Optimizer, Not a Chatbot, for Equity-Comp Math | OptionsAhoy | OptionsAhoy > Multi-year equity-comp scheduling is a constrained optimization problem. The candidate space is larger than is practical to work through in-context. A benchmark of five frontier LLMs overstated the after-tax result of their own proposed schedules by 2x to 20x. The optimizer at OptionsAhoy returns the optimal schedule across its full candidate space, computed against the relevant federal plus 50-state plus DC tax code. Markdown twin of https://optionsahoy.com/why-deterministic (canonical). More for agents: https://optionsahoy.com/llms.txt For agents and the curious # Why a multi-year optimizer, not a chatbot, for equity-comp math Multi-year equity-comp scheduling is a constrained optimization problem with a huge candidate space and a single provable optimum across that space for any given input. Large language models (LLMs) sample plausible answers; optimizers search the full space and return the best one. For five-figure-and-up equity decisions, the difference between "plausible" and "best" is real money. ## The benchmark Five frontier large language models were asked the same Incentive Stock Option (ISO) exercise problem: 50,000 vested shares, $4 strike, $90 fair market value, four-year horizon, California resident, single filer, 5% cash return. Each model got three independent runs. Fifteen trials in total. Every one of the 15 trials overshot reality by 2x to 20x on the after-tax outcome it claimed for its proposed schedule. None recovered the optimal plan the optimizer finds across its full candidate space in under a second. Live benchmark, updated for the latest models: [optionsahoy.com/benchmark](https://optionsahoy.com/benchmark). Full write-up: [HackerNoon: But can it do taxes though?](https://hackernoon.com/but-can-it-do-taxes-though-why-you-shouldnt-trust-chatbots-with-tax-optimization-math) Also on Medium: [Should we implicitly trust AI with our optimization problems?](https://medium.com/@akorytko/should-we-implicitly-trust-ai-with-our-optimization-problems-like-taxes-1085167055f9) ## What the optimizer does Three properties, all simultaneously: 1. Searched, not guessed. The engine searches its full candidate space of share-per-year combinations, scoring each against the tax cost across your horizon, then refines the winner share by share. On a published tractable case the result matches a brute-force maximum to the cent. 2. Tax-code coverage. Federal (ordinary brackets, long-term capital gains, AMT with credit recovery, FICA, Net Investment Income Tax) plus all 50 states and DC (state ordinary brackets and LTCG treatment; state AMT modeled for CA, CO, CT, MN ). No state-skipping, no bracket approximation. 3. Verifiable. Same inputs always return the same schedule, so the recommendation is reproducible. Re-running the tax math end-to-end on the chosen plan reproduces the headline outcome to the cent. ## What OptionsAhoy does The free calculators on this site compute against current-year tax authorities, not learned approximations: - Tax brackets sourced from IRS Rev. Proc. 2025-32 and the One Big Beautiful Bill Act (OBBBA) for tax year 2026, and asserted against those published figures by an automated conformance test. - Per-state ordinary brackets and long-term capital gains (LTCG) treatment for all 50 states plus DC, with explicit AMT modeling for CA, CO, CT, and MN . - Validated against 870+ unit tests covering bracket walks, AMT credit recovery across years, state conformity, and the optimizer's search path. - Multi-year ISO schedule optimization returns the optimal exercise plan across the search space, not a sampled candidate. Full math sourcing and known scope gaps: [/methodology](https://optionsahoy.com/methodology). ## Try the calculators - [Multi-Year ISO Exercise Schedule Calculator Plan a multi-year ISO exercise schedule that minimizes AMT — federal and state, with credit recovery and grant-expiration timing.](https://optionsahoy.com/tools/amt-iso) - [NSO Exercise Calculator Calculate the after-tax payout on a non-qualified stock option exercise (federal, state, FICA), then compare selling now vs. holding for long-term capital gains across your chosen horizon.](https://optionsahoy.com/tools/nso) - [RSU Sell-vs-Hold Calculator After your RSUs vest, should you sell at vest or hold? Compare after-tax payout — federal, state, FICA, plus the short-term-vs-LTCG cliff at 12 months — and see exactly what holding actually costs.](https://optionsahoy.com/tools/rsu-sell-vs-hold) - [Stock Concentration Calculator See how concentrated your single-stock position is, what a 30/50/70% drawdown costs, and the trade-off between selling down and hedging — with multi-year tax math.](https://optionsahoy.com/tools/concentration) - [Protect Your Stock Calculator Price a zero-cost collar, protective put, or put spread on a single-stock position. See annual cost, max loss, upside cap, bad-year coverage, and which structure suits your floor.](https://optionsahoy.com/tools/protective-put) - [QSBS Qualification Checker Does your founder or employee stock qualify for the Section 1202 QSBS exclusion? Check six of the eight tests from your facts, see your exclusion percentage, federal tax saved, and state conformity, all instant.](https://optionsahoy.com/tools/qsbs) - [Equity Funding Plan Calculator Need to net a specific amount of after-tax cash by a date — for a down payment, tuition, sabbatical, surgery, or business buy-in? See the minimum-tax sell schedule from your existing stock lots: federal LTCG, state, and NIIT, with bracket-aware splits across calendar years.](https://optionsahoy.com/tools/equity-funding) - [RSU Lot Order Calculator Diversifying company stock? See which of your vested RSU lots to sell first, on which dates, and the year-by-year tax — versus what selling oldest-first (FIFO) costs you. Specific-lot identification, long-term deferral, and multi-year bracket spreading.](https://optionsahoy.com/tools/rsu-lot-order) ## For developers and AI agents If you build agents that help users with equity compensation, [/for-agents](https://optionsahoy.com/for-agents) has the integration surface: REST API at /api/v1, Model Context Protocol (MCP) server at /mcp, OpenAPI 3.1 spec, schema.org JSON-LD on every tool page, and a public [/llms.txt](https://optionsahoy.com/llms.txt) capability index. ## Plan your whole equity portfolio The free calculators each solve one decision. OptionsAhoy's full optimizer jointly schedules ISO and NSO exercises, RSU vests, hedges, and sales across bullish, neutral, and bearish scenarios for the same horizon. Beta is free.