TL;DR The founder of Gumroad fired all his employees and replaced some with and rehired some on contract. Gumroad does not provide benefits like healthcare. Your hourly rate gets cut cut in half after you work more than 20 hours a week. The article is a nice way of saying that the founder largely just collects rent while putting minimal resources into the business.
Yeah, hard pass. If I'm gonna be a 1099 contractor my rate will need to be very high (roughly $500/hr). Otherwise I'm sticking with my FTE job. And I'd need to be able to pick up more than the 20 hours per week than this guy will give me too, so I'd need multiple clients.
And on 1099 you can have as many clients as you want.
I can understand why someone would pass, but within its own context it doesn’t sound like a bad deal to me, particularly for people who for whatever reason don’t need to bill that high.