I'd get him to lift the lid on DrownedInSound. Ask the difficult, previously unanswered questions like:
What happened with the Sky funding?
How many hundreds of thousands of pounds did he make from his release of The Kaiser Chiefs debút single?
What is the REAL story behind the stripping of TheoGB's mod privileges?
Why does the site keep logging me out?
I'd also ask him to answer accusations about his messiah complex and the REAL reason why he hypes Paramore so much.
Trying to canvas for any interest here. Interested?