I don't think Doog expected to get paid (initially). If that was his motivation he would probably ask for the specific amount beforehand. My guess is that Dean got pissed off/felt back-stabbed after Doog publicly described the flaw (after it was fixed) which was somewhat damaging to the site's (if not Dean's) reputation. So if the subject of bounty came up after that - that's probably why he refused to pay. Again, that's just my guess.
Yeah I guess this is what I'm wondering. Doog feels that he's due money, which is probably fair (I have no clue what he did/what needed to be done, but assuming he helped fix a security leak it's fair to say that he should prob get compensated for that, especially if that is the precedent). Did he always feel that he was due this money, or did he adopt that attitude after Dean said he wouldn't pay him?
Seems like this all boils down to respect, and both sides feel they were disrespected by the other. Maybe if we get back to the original issue, both sides can start seeing things from the other one's point of view and see that it's pretty likely that no disrespect was originally intended from either.