I'd say the most annoying part (of so many annoying parts) was when he says:

"The hard part is defining what your brand is and what it aims to become."

And then somehow supports that with the opposite:

"Is Yahoo “whimsical, yet sophisticated. Modern and fresh […] human, personal […] proud”? Currently, Yahoo is not associated with being whimsical or sophisticated, rather it is mostly boring and dull. It doesn’t portray modernity or freshness, it feels obsolete and dated."

Apparently had he been hired, he'd have designed a logo to what he believes are Yahoo's current brand - dullness and obsolescence instead of what he suggested at the outset which is what you want your brand to be.