The SilverStripe Core Committer team (as explained below) have held their first hangouts meeting (16th via hangouts overall) to youtube and you can watch and get some insight into the project and where it's going. Per the official post related to this video the SilverStripe team confirmed they post regular videos on their youtube channel which are announced via twitter and other social media platforms.

A couple of days ago we posted a video from the SilverStripe team (here: Upgrading to SilverStripe 4) which was recorded at a decent meetup, this second video is from the same talk which focuses on the new GraphQL module which can be found in SilverStripe 4 as a core feature. 

The SilverStripe website has posted a video covering the SilverStripe 4 upgrade process, unlike most upgrade videos this is actually from a recent meetup at the SilverStripe headquarters attended by SilverStripe users themselves. The talk was hosted by SilverStripe developer Robbie Averill