Podcasts are a great way to gain understanding directly from people who work in the industry.  My favorite podcasts are from 5by5. My breakdown of the shows:

Back to Work – Merlin is crazy if you haven’t heard/read him before, but I definitely love every minute of it. Certainly a good place to hear the affirmation that it doesn’t count until you ship. The show is also super meta, which is definitely delightful to me as I love seeing how things work and seeing how things can be deconstructed.

Talk Show – as much as I like Gruber, I don’t really enjoy this show. Gruber comes off disinterested and grumpy compared to his more intellectual and thorough blog. I wonder if most nerds are really like that.

Build and Analyze – Marco has a lot to say and definitely carries that young tech entrepreneur feeling. The show gives a strong idea of his mindset, especially on more recent episodes where he talks about building a small content management system for his blog.

The Pipeline – Interviews aplenty. I high quality guests with a good hit rate and usually Dan keeps the questions coming. I have enjoyed listening to the back episodes of this show, especially the ones where he interviews someone who later becomes a cohost on other shows.

The Big Web Show – Generally the topics here are good and the guests are important, but sometimes the show sometimes slows to a crawl. Zeldman isn’t as good as Dan at keeping guests on topic. Sometimes Zeldman’s questions actually lead the guest into bigger tangents.

Critical Path – An amazingly insightful show about the mobile phone industry.  Super informative and educational, but seems to come out rarely.  I’d love more!

Hypercritical – Definitely my favorite show and the one most relevant to me. I read Siracusa’s giant OSX reviews before I even had a Mac and I appreciate his super thorough style. I’m hoping he can keep up the momentum. The recent programming episodes have given me hope.