As a senior sysadmin who has frequently been in the role of CTO because businesses often don't even have a CTO... my number one pain was always when the technic

As a senior sysadmin who has frequently been in the role of CTO because businesses often don't even have a CTO... my number one pain was always when the technical debt requires more personnel in order to manage properly but upper-management refuses to hire more people for the role. I know your question seems more oriented towards the SV-startup/dev cycle, so my answer is more for general business (even ones without programmers). My pet peeve though has always been structured cabling. I don't know if yall understand just how bad the cabling situation is is many businesses, but it's bad and for some reason they really don't like spending money on that particular thing even though it's one of the most important things for keeping a business up with the times (and the data rates that match). So, in general, it has been a frustration with the communication gap between the technical team and the C-level and the board. Too often you either get a CTO who wants to "program with you" or one who is too much MBA and not enough tech. As a sysadmin I have realized my number one failure was not working on my MBA-side more and thinking purely technical proposals and solutions would win the day. AKA I should have spent more time golfing and going to lunch so I had more power with the Cs.