I think Matt should go ahead and run because he is in no danger of getting Wally Pipp'd.
If he wins, his radio show can limp along for years before getting cancelled (like SNL and the KSR blog, it has a really good "parking spot" at this point).
By the time he loses or wants to quit and come back to reclaim his ambassadorship, the tech will have caught up to supporting his independence on the radio front, not just the blog/news.
You heard it here first, Matt and you have my blessing.
Obviously, you won't change anything, but Godspeed on attaining power House of Cards style. I can see how that will seem more fun than shilling for mattresses at a certain point.