Earlier quoted context omitted.
This is typically not the case. The lock-up specifically prohibits trading options, pledging shares as collateral for debt, selling shares, or gifting shares to charities. It also usually a catch all for benefiting directly or indirectly (through a trust or foundation) Source: I founded GrubHub and wrote the article referenced here.
Thanks for information - I wasn't aware this applied to non-insiders or ex-employees too for derivatives that expire after the lock-up. I guess no amount of financial engineering can unscrew the little guy. :) BTW, love your company and use it often, thank you!
I don't know how they'd enforce this, however. Seems like you'd have to have a big mouth, and they'd have to be willing to fire you for it.