I started working at SpiderOak back before we had an HR department or many formal company policies. Most of us were contractors. Since we didn’t have other benefits, we had “unlimited time off.” (This was pretty popular in the startup world back then.) The idea is great; take as much time as you need! The thing the company values is you getting your work done, not counting your hours at work. In practice I found that to be true. I was almost never asked to track hours or account for my time. As far as taking time off, I was also never told I could not take time off. But no one ever took much time off.