Ask HN: When do you take some off the table?

Ok, I know it appears bad to ask, but at what point do founders of VC backed companies take a little off the table to ensure they are well cared for? I am not saying they become wealthy or anything, but when have you/do you do it?

I have no backing in the VC world, so it is truly just an academic learning exercise for me. But I personally haven't seen it addressed, and you can only live on a thread for so long before your productivity and capability wane (e.g. you need to afford a reasonable vacation etc). Obviously the focus should be on the business not on cashing out, but you have to eat and pay bills.