There are very few cases where Medicaid would be available to would-be entrepreneurs, especially older ones. In most states, Medicaid has a maximum asset level of $2,000, which would disqualify most potential older founders, who presumably would want to save at least a few thousand dollars as a cushion before quitting their job to do a startup (in some cases money in retirement accounts can also count towards the threshold, which would disqualify others). So they really do need to try to buy private health insurance in the non-group market. Medicaid's basically only a program for completely broke people living paycheck-to-paycheck.