First company I worked for, built around 40 websites with Drupal 7...in only a year (don't know if it's a lot for today's standards, but I was one guy doing everything). Of course I didn't have the time to keep updating everything and I continually insisted to the boss that we need more people if we are going to expand. Of course he kept telling me to keep working harder and that I "got this". Well, after a year a couple of websites got defaced, you know the usual stuff if you've been around for some time. Felt pretty bad at the time, it was a similar feeling to having your car stolen or something.

Anyways, fast forward about 2 years, started working on another company, and well...this one was on another level. They had a total of around 40 websites, with about 10 of them being Joomla 1.5 installations (Dear Lord have mercy on my soul(the security vulnerabilities from these websites only, were greater than Spiderman's responsibilities)) and the others where WordPress websites, all that ON A SINGLE VPS, I mean, come on... Websites being defaced on the daily, pharma-hacks everywhere, server exploding from malware queing about 90k of spam emails on the outbox, server downtime for maintenance happening almost weekly, hosting company mailing me on the daily about the next malware detection adventure etc. Other than that, the guy that I was replacing, was not giving a single fuck. He was like, "dude it's all good here, everything works just fine and all you have to do is keep the clients happy and shit". Sometimes, I hate myself for being too caring and responsible back then.

I'm still having nightmares of that place. Both that office and that VPS.