Did not watch the presentation but IMO the primary mistake was not declaring EOL for 2.x sooner. Other languages had similarly breaking changes and they simply gave short time before legacy version was declared EOL and developers ported their applications to the new version.

In Python it took 10 years, and even now you can't get companies to migrate, because why make developers do the work when application still can be used. Many places will probably start the migration in 2020, which shows that giving 10 years head start was a mistake and all it did was create FUD and division in the community.

The Python 3 immediately picked up for new projects after announcement that 2.7 will no longer have new feature and only bugfixes in 2015. Industry will wait for the last moment when all support for 2.7 will be ceased in 2020.