[diN0bot]

I'm interested in this, too.

Also, it seems like there are still ways to receive some revenue from creating useful content that thousands of people are interested in. Not because the money is so important, but because there are parts of community engagement that are fun to do and feel rewarding, and there are other parts that can be contracted.

I didn't understand the "make a media company" or nothing aspect considering he is still podcasting as a fun hobby anyway.

[michaelt]

  I didn't understand the "make a
  media company" or nothing aspect

If I quit my BigCo job to bootstrap a business from my savings, I'd want to recognise if the business was failing well before it lead me to personal bankruptcy. So I'd have a deadline and success criteria.

Presumably his success criteria for the become-a-pro-podcaster experiment wasn't being met selling his ad inventory alone, and selling extra inventory to his existing sales prospects got him closer.