In my mind I've been thinking of over writing, or unbalanced covered calls... Say, having 300 shares @ 15 and write 5 20 calls, so you're short by 200 shares. You've got time to react by either buying more shares if the underlying starts to move up, or take other action. Folly? Too dangerous? Thank you.
You got to have some cash available to sell those 2 contracts naked. Suppose they discover the cure for old age, and the stock gaps to a thousand dollars a share. How you going to hand over the other 200 shares you've obligated yourself to?