In this week’s meeting, Dan Benjamin of 5by5 works through step five by sharing his high expectations in being able to watch content whenever & wherever he wants, how he has the luxury to pay to remove annoyances with media consumption, why it spurs his growing attitude of entitlement, but admit that these are indeed privileged problems to have. In addition, we discuss the fears of updating iPhone apps right away, paranoia with products and services tracking your location, ad relevance versus intrusiveness, ad retargeting, and the podcasting "renaissance".