Anything is possible since we are not a party to what was offerred. What we do know is that he will pay taxes on $20k of income regardless of what the shares do. If they go up he has to pay income tax on $20k and a capital gains on any amount above $20k. If they go down he still pays income taxe on his $20k income and has a capital loss if he sales for under $20k.

If one is pessimestic about the share price and HAS to hold them for 4 months you don't want shares. If you are optimistic about the share price the hold period doesn't matter to you as much. This is the fourth time he has put his money into ZEN stock (3, 2000 share purchases in the fall and this one) so I read that as optimism.

... Been There