What he means is that he likes being short vega on longer dated options. Implied vol is usually higher on longer dates, so you are selling more expensive vol this way. Obviously, the draw back is that if you are protecting yourself by buying shorted dated options, you going to decay.
If anything, he'd make money if the curve inverts (if I am reading him correctly, he's short the far end and long the front). What would hurt him is a massive bullish steepening of the term structure.
that makes sense.. and in what case would that typically happen .. and what would one do to hedge against that?