http://www.media.mit.edu/events/2012/04/18/media-lab-conversations-series-tim-oreilly
Ask him about remaining a private concern. I know this was a big, um, "concern" for him (stay private vs. go public), and his perspective on the matter might be very interesting.
Also, looking in from the outside and rather superficially, his personal focus vis à vis O'Reilly Publishing seems to have shifted more to the conferences. Is this an accurate perception?
More recently, I've encountered a few less than satisfying titles in the O'Reilly lineup, particularly around the latter half or the end of the last decade. Has this been noted within the organization, and if so, are they addressing it?
As for big data, his son in law is in renewable energy. What has Tim been learning from and about that sector WRT data collection, analysis, and application?
Do you think programming should be a basic element in education i.e. reading, writing, arithmetic, programming.