The IPO Illusion: When a Stock Windfall Leaves You More Exposed, Not Less
An initial public offering is supposed to be the payoff moment — the day years of below-market salary and illiquid paper equity finally convert into something real. But for many employees, IPO day marks the start of a different problem: a portfolio balance that looks enormous on screen while remaining stubbornly hard to actually rebalance. The stock is suddenly “real,” the tax bill is suddenly due, and the ability to sell is often the last thing to arrive. That sequencing — value first, liquidity last — is what turns an IPO from a tax-planning puzzle into a concentration-risk problem.