The episode I would like to point out is the one on which Jason Kottke joined as a guest. John invited him to celebrate the 20th anniversary of kottke.org.
I am not a big kottke.org reader but nevertheless I found his story and the history of the site very interesting. I am always fascinated with these type of project where one person runs a successful business by just relentlessly publishing on the internet in a very focused way.
Check out The Talk Show episode in question right here.