It's clear from what he's saying that Automattic once OWNED the trademarks, but transferred those trademarks to the WordPress Foundation, and thus Automattic is NO LONGER THE OWNER of said trademarks.
What Automattic has is an exclusive license to use and sell the commercial licenses of the trademark.
Automattic: Owns the commercial right to use and sell the license
This is done because the WordPress Foundation is non-profit. The legal intricacies of this have been worked out a long time ago. You want to use the WordPress license? Then you'll have to buy it from Automattic.
What Automattic has is an exclusive license to use and sell the commercial licenses of the trademark.