De-Risking Chonky Stock Positions with Tax-Loss Harvesting, Exchange Funds, CRUTs, and Section 351 Conversion

Andre and Brent walk through the thorny problem of concentrated stock. They cover the plain option (just sell and pay the tax) then unpack alternatives: tax-loss harvesting over time, tax-aware long/short strategies using leverage, exchange funds, and CRUTs. They even touch on seeding new ETFs in-kind using Section 351 conversions. Along the way, Costco avocados and breakfast choices make a cameo.