PlanGrid has (or had?) "unlimited" vacation time. Unlike some places they really encouraged people to use it. There was no issue with liabilities on the books since you weren't banking vacation days; it didn't make any financial difference to PlanGrid if you took 0 vacation days or 5 weeks.

Ryan was trying to make sure I wasn't over-working myself and I appreciated the thought (it just so happens I was waiting to take a long Christmas vacation).