I started out listening to Startups For the Rest of Us and it is definitely one of the best. However, I feel that more recently they seem to be running out of ideas for fresh topics, which is completely understandable when you've recorded 179 episodes.
More recently, I've really come to like Bootstrapped with Kids. As the article says, it's honest and funny. For someone who is still working 9-5 and hoping to make the jump to a bootstrapped existence, this podcast lets you hear from real people in a similar stage of the progression.
If you are interested in hacking systems you'll love this podcast. Things like geographical arbitrage while bootstapping (baseline expenses somewhere cheap, sell to customes where its expensive) and tax "loopholes" like the advantages of a Hond Kong corporation or the "Foreign Earned Income Exclusion" (internet businesses can get 95K completely tax free == 30-40K extra in the bank).
To top it off the two hosts, Dan and Ian, are just plain entertaining. One of their recent riffs about owning fork lift while still being location-independent made me choke on my lunch w/ laughter.
Here are my top 10 of the 225 episodes I've listened to:
I'm technically location independent from my job but not location independent family wise. I live vicariously though Dan and Ian for the time being.
Everyone's key to location independence or bootstrapped income is teaching everyone else about location independence or bootstrapped income.