Yes and no. I agree with everything except #5. My marriage & kids are irreplaceable. So if you have everything else, which is a more rational bet: - Investin

Yes and no. I agree with everything except #5. My marriage & kids are irreplaceable. So if you have everything else, which is a more rational bet: - Investing in a low probability, massive payoff - Investing in a lower (yet still high) payoff with less variation in expected outcome. There are huge segments of the economy where you can buy a small business for at a 3 - 6 multiple of annual earnings. Many companies in this space are unsophisticated, so there is massive potential for operational improvement as well (introducing basic process, tech, and marketing strategies).