> Everyone at Gumroad is paid very well and should be able to afford the same.

Have you looked at how much decent health insurance coverage costs on the individual market without income-based ACA subsidies?

It's absolutely insane, and even more insane if you want family coverage. For a similar, but nowhere near equivalent, of an employer provided healthcare plan, I'm looking at spending more than $9,000 in premiums each year, a $3,000 deductible, a $8,000 out-of-pocket maximum and co-pays for doctor visits and medication.

If I add a spouse and one kid, for a plan similar to an employer provided plan, premiums sky rocket to over $30,000 a year, with a $5,000 deductible, a $17,000 out-of-pocket maximum, co-pays etc.