These people are the same people who complain about being unemployed but fail to apply for jobs. They also are the people who turn down a job flipping burgers because they think it's beneath their dignity. Instead, they opt to be leeches.
I listen to all of your Anarchist podcasts, and you've done well as dispelling the myth that in order to be successful, one must have "exactly what Jeff Berwick has." One think that struck me the most was when you discussed a woman who moved out of the US, made $20,000/year working online. She had a high standard of living and was exceptionally happy. That's success.