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My current job is extremely stable and I am very well compensated compared to my peers. I am, naturally, quite reluctant to take a leap of faith like this. I believe my compensation would be within %5 of my current salary, and my equity would be reasonable for my position and the stage that the startup is at.
My question is this: would the trajectory of my career be drastically changed by taking a CTO position for 3 - 5 years at a startup? Or would other companies in the future just look up this company and realize very quickly that it is a pretty small operation? I'm weighing best and worst case scenarios here...worst case is that the company goes bust and I have 3 - 4 years of experience as CTO of a startup.