Um, yourself? I have an ACA plan. It handles all the catastrophic stuff, and has a very reasonable deductible. It costs me ~$360/mo. Certainly this is a different ball of wax with a family (figure more around $1100-1400/mo for a reasonable plan) that has dependents.
In my case I quit working eons ago. I bought health insurance via a state marketplace (RomneyCare). My total costs (business insurance, legal, marketing) were less than $10K. I was profitable at the end of month two. At the end of year one, even with expenses I was making 70% more than I could as an employee in most companies in Boston (and around what I could theoretically get at Google, if they would even give me the time of day). It's been 5 years, and I still question why I didn't do it earlier. Worst case I had two years of savings in the bank from average-paying software jobs.
You don't have to do crazy things that require millions of dollars. I'm working on a "big thing" (to me) now that will require ~3000 hours of development time to launch, but I'm doing it all myself, and my costs are $10-15K and learning some new skills. Though the very real potential is for it to easily replace business one, and put my income well above what even the Valley could ever pay me. I wouldn't of done that quitting a job though -- that's something I would build on the side and launch while still employed, and only quit when it's clear the revenue will cover expenses.