LossPilot

LossPilot is a web + mobile app (traditional + AI) that connects to brokerages and continuously scans taxable accounts for realistic tax-loss harvesting opportunities while actively minimizing wash-sale risk across accounts and household members. It flags lots with meaningful unrealized losses, estimates federal/state tax impact, and proposes compliant replacement baskets (e.g., correlated-but-not-substantially-identical ETFs) with a clear audit trail. The AI layer explains recommendations in plain English, highlights edge cases (dividend reinvestments, partial lots, options, multiple brokers), and generates a CPA-friendly report for Schedule D/8949 support. The app is blunt about when harvesting is not worth it (small losses, high trading costs, short holding periods, or low tax rates). It’s not a robo-advisor; it’s a decision and documentation tool that helps DIY investors and tax pros execute confidently.