Technical debt is like debt, if you are borrowing it to expedite something and you actually pay it down later when you have the resources it can be a good thing. Sometimes though, it is just poor development practices or design. Here is a presentation I gave at the FirstRound Capital CTO conference a while ago, it was pretty well received and fun to talk about things people have seen in their own companies:

http://www.slideshare.net/spullara/managing-technical-debt-1...