Should You Vest Only at a Liquidity Event?

Alicia worked for a great entrepreneurial company. As a promising young marketing staffer, she was excited to get non-qualified stock options that she hoped could be worth a lot of money not too far down the road. The options had a six-year vesting rule, by which time she would have the choice to use after-tax dollars to exercise the awards and get the options, paying income tax on the spread. But Kevin, the owner, assured her that by that time, the company would go public or, more likely, be sold to a well-heeled buyer, so she’d never actually be out of pocket. But things didn’t go as planned.