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I'm curious, for various locations and business scenarios, what the optimal choice is for getting paid help for your taxes.

E.g., when is a simple accountant worthwhile? How about one specializing in business taxes? When (if at all) should you switch to a full blown accounting firm? When should you hire a CFO to optimize these choices for you?

These all cost money, so I assume there's some break-even point on the investment. And other pros/cons for a company owner delegating this part of the business.



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.




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