Job security can push it back in the other direction though, if I'm at a start up with say 6 months cash in the bank I can't be to certain that I'll still have

Job security can push it back in the other direction though, if I'm at a start up with say 6 months cash in the bank I can't be to certain that I'll still have a job there for me after that. If anything the salary should be market rate on the equity for the extra responsibility/ effort of being in a small team. As much as some startups advertise a good work/ life balance I'm sure it's not going to fly working your normal hours if overnight or over the weekend the service has a major problem.