If your startup has a chance at an exit in the >$5M range, then you should definitely have a personal accountant analyze your situation. Capital gains taxes start to crush your dreams when you are into that realm, and structuring things more intelligently can save you millions of dollars. In terms of income, I think anything below $400K or so can be handled without an accountant. Above that level, use an accountant simply to provide a backstop in case you get audited, because you’re now in the realm where the tax authorities can make some real money by finding things you did incorrectly.