I would scope out his servers. Try to find an exploit... get in and totally just ruin his stuff.
I'm not telling you to do it, just saying that's what I'd do.
By far more effective than email. I'm sure you could easily cover your $500 that way.. and then some.
Wardriving is your friend. Just carry a laptop/PDA with you as you drive around neighborhoods looking for unsecure wireless access points (and believe me, there are a TON).