Imagine the day the wire finally hits your account. You have spent a decade or more building your company, grinding through late nights, navigating making payroll, and eventually executing a successful exit. You are likely prepared for the immediate capital gains tax hit. But while you are celebrating the liquidity event, the IRS is waiting for a second cut. Without smart planning, capital gains, estate taxes, and income taxes can swallow 30–50% of your business sale. Most fo