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Your scenario seems unrealistic at best. If you artificially inflate the valuation of your company then possibly you might pay more taxes. So, don't do that. But I don't think Harris's proposed law would have led to you paying more taxes in this weird scenario in any case, as you need to have $100m or more in assets.

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It’s unrealistic but technically true. That’s a bad law.

No, it's a bad hypothetical.

No it isn’t. That’s exactly why taxing non realized gains isn’t common around the world.

As above, it is common. See: property taxes and mark to market. It is perceived as being administratively infeasible because the folks who would be paying the biggest bills want you to believe that.

I don’t think it’s technically true that your shares in your company would be worth a multiple of what someone else paid for their shares when your shares were valued as part of your overall wealth for tax purposes.

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