Always take them.
When I look back at the many mistakes I made as a 2x founder, both times with some degree of success in the end … and there were so many … one thing I am 100% glad I did was take vacations.
And I mean — normal, full vacations.
By that, I mean, a full week. In a normal place. And I only checked email once a day, once I had real VPs in place (before that, when I was the VPs, I still had to be on email all the time).
It’s tough to take any time off until you have a management team, at least a partial one. In the early days at EchoSign, I did the customer support shift from 11am-6am. That’s an anti-vacation, let me tell you.
But once you have a team you can trust, take the time off. You need it. And they will do fine.