What he saying is this: he knows a grand total of 0 people whose accounts have been hacked because their password was too simple. It's almost always something else. Yet password management only seems to become more complex and cumbersome over time.
And it's not even debatable that major apps, sites, and operating systems ranging from Google Maps to Firefox to iOS have grown suckier and suckier over the last few years. This isn't old-man-yelling-at-cloud stuff -- it would easily show up in usability studies, if the companies involved actually ran valid usability studies. When I encounter the same daily frustrations as my non-computer-geek friends, something's wrong. That never used to happen.