Hey, they seem to be streaming full episodes on the TV Land website:
http://www.tvland.com/originals/ipitythefool/
All of Episodes 4 and 5 are currently available.
Most of T's shtick is just that--shtick. There's certainly very little real "learning" value in him giving platitudes and then editing footage to make it look like people are actually listening to his platitudes. Its transparently obvious that most of what you are seeing is a complete setup--they don't even try all that hard to hide it.
But its amusing as all heck. The deliberate way he speaks. The good natured way that he accepts that he's inherently cheesy. It's watchable, although you won't exactly want to go out of your way for it. Compare it to the "Celebreality" shows on VH1 instead of "Dr. Phil" and you may have a more honest impression of it, since those shows are kind of dreadful, and this one at least TRIES to be positive, even if like those shows it IS inherently just cheap-to-produce voyeuristic grade-D "celebrity" driven nonsense.
There ARE a few moments of sheer brilliance. For example, when Mr. T is faced, in Episode 4, with a dance class, their bickering stage moms, and their bitchy dance teacher, there's an absolutely hilarious moment where he quotes 17th century poet John Donne (after, without shame, stumbling over how to pronounce the poet's name). For that moment, at least, this is appointment T.V.