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You cannot avoid the 20% company tax on distributed dividends... This is company tax not personal tax. For you personal tax the best if you have an Estonian company would be Estonia obviously (no personal income tax on dividends received).

How would they find out?

If he uses his Estonian company to invest then there is no taxes as long as it is not distributed... good to compound money...

As you have your company in Estonia, why don't you get residency there? Estonia as no personal income tax on dividends received and as long you stay in the Estonian population register you are considered resident (and tax resident) from day of arrival... To be in the population register you just...