TaxLotPilot

TaxLotPilot is a mobile + web AI-assisted investing companion that shows the real after-tax outcome of selling any position before you place the trade. Users connect broker accounts (or upload CSVs) and the app maps holdings into tax lots, cost basis methods, wash-sale risk, and short/long-term capital gains. It then simulates “sell X shares” scenarios and recommends the most tax-efficient lot selection (or warns when you can’t control lots at your broker). It also flags when harvesting a loss will likely be disallowed due to recent purchases across accounts, and generates a clean summary you can hand to your CPA. This is not a robo-advisor and doesn’t pick stocks; it prevents expensive, avoidable tax mistakes for DIY investors. The product is only as good as the data connections and rules engine—so the MVP should focus on a few major brokers and rock-solid calculations.