Solo founder for years, but eventually grew to the point where I hired a small team that can handle 95% of issues. I was at the point where I had to or I'd lose my mind with the control it had over my personal life. Hiring yourself out of that role is a journey in itself.

Anyway, yes, you're the one wearing all the hats, so it's on you. There is no real break, because even if you had someone watching the shop, many times the thing that breaks is the thing only you have deep insight into.

I've been on cross country drives, woken in the middle of the night, at family parties, hanging out with friends when I've gotten paged - and immediately stop what I'm doing to fix the issue, even if it takes a while and ruins said occaision. My platform is ad related, so every second of downtime is pissing off a lot of people because it's directly linked to their revenue. Thankfully that never happened while I was on a plane. I did have to buy a ridiculously expense WiFi package on a cruise ship twice to monitor things.

I've mitigated most potential issues with better infrastructure, tests, and early warnings, but the occasional unexpected item slips in, maybe once or twice yearly. Luckily I have a staffer with deep knowledge of the platform to handle that now. It took a while to get to that point.