We use a 'PEO' (ambrosegroup.com). Essentially, they are the 'employer' for all the employees, and provide payroll, medical, dental, 401k, travel accounts, etc - and bill us for the total (plus something for them) every two weeks.

For a small startup, it makes a lot of sense - no time is taken up with 'HR' issues. And (from my initial research) the group medical rates that they can get more than make up for their administration cost. Making the payroll, etc, all a free bonus...

The ever popular, spouse whose employer provides healthcare.

However, three years ago we had private family coverage through BC/BS Alabama. Because BC/BS has ~90% of the private insurance market in the State [Alabama essentially has a single payer system] our premiums were very low compared to much of the rest of the country. They were even lower than the similar coverage offered through the BC/BS plan at my former employer.

This is a question I would love more clarity on. Especially pre-employee - what do bootstrapped founders typically do for their own healthcare? Do most roll the dice and go without? If so, do you stop going to regular dentist check-ups, etc.?

If you live in MA, you can purchase health insurance using the state exchange over the web. Minimal prices for a family of two are about $550/month (or were last I checked). Prices/availability can only vary based on age/gender/location so you don't have to worry about being denied coverage for a preexisting condition. You can cancel with one-month's notice.

https://www.mahealthconnector.org/portal/site/connector/