Yes. Again, he will have the exact same amount of money in both cases at the end of the day. Somehow you envision that finding opportunities to return 10.000x on investment are a tax loophole. If have such “loopholes” available simply let me know and I will fund them on a pre- or post-tax basis. Perhaps society should allow more people the freedom to find these lottery tickets on their own and grow instead of demanding the funds and investing them in things like abandoned military equipment in foreign countries.