I've had multiple friends in that bracket explain to me how they saved tens of thousands through "tax optimization strategies" involving crypto wash trades or f

I've had multiple friends in that bracket explain to me how they saved tens of thousands through "tax optimization strategies" involving crypto wash trades or fraudulent home office deductions. If you've ever gotten options from a startup, you've probably benefitted from the 409a valuation process, which is quite a lot better than the "make up a number" process it replaced but still provides a lot of wiggle room (except at the end of a fundraising round) to produce an artificially low valuation.