If I was starting a new company I would without a doubt push towards doing frequent deployments all day long.

That said, I would would never push for it at my previous company. At this company it's something they've been doing since day 1. It's always been built into our process, culture, and hiring practices. At my previous company the "agile" process was just a shortened waterfall process. Though many of the engineers were very talented, and responsible... there was more than a handful that I would never trust to "self test" their code, or to monitor it as it deploys.

I definitely like that the more I think about it. We try to do deployments every couple months, but changes are so big and risky we end up pushing off deployments to the next release just because nobody wants to risk it.