And there is the problem I was referencing. It is a pretty big ask for everyone to just work for free for months and it is something only a privileged few can do. Plus a site like Deadspin isn't a small site. I'm not sure of the exact headcount, but it looks like roughly 10 writers have left recently. That isn't counting any tech people, any sales folks, or any other operational people. The idea that "content is cheap" is basically the exact problem that caused this whole debacle in the first place.
Your first paragraph says that content-based websites are easy even for poor people; your second says it's hard and that you have to work for free for months. I'm confused. How are poor people supposed to work for free for a few months and then have enough to pay themselves reasonable salaries with health care/insurance and retirement and PTO?
The reason they don't do this is because running a content-based business is much harder than they claim it to be, and it's easy to claim things when you don't have skin in the game: when the venture-capital owned company goes under, they'll just get another job, while if they start their own business, pool up some initial capital and work for free for a few months until they make enough revenue to pay themselves reasonable salaries, they're risking much more.