[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.