1. I made the biggest career mistake of my life by staying at one company from 1999-2008. I missed out on so much of state of the art technology that I spent the next 8 years trying to get caught up.
A lot of the things I was just learning in 2009 were already common place for years before then.
2. As much as people say "technologies change fast", a lot of the higher level fundamental concepts they discussed 10 years ago are still relevant today.
Now back on topic...
A daily podcast that lasts an hour? It's remarkable that he can keep up that pace. Could he make just as much money from having fewer podcasts? would the scarcity make the podcast more valuable to advertisers?
I think John Grubers talk show podcast charges about $7500 per spot with 3 spots during an average 2 hour show per week. There have to be more software developers who would want a high quality podcast than people willing to hear Gruber's ramblings (no offense - I listen to his podcast every week).