Zooming out a bit, Automattic acquired Tumblr and like all those before it seems to be choking on it.
Competitors like Wix, Squarespace, WebFlow and Shopify are all nipping at WordPress' marketshare.
I don't know what WordPress.com's stats look like, but blogging is out of sytle. New cool kids want the new black. That is to be social media influencers. Along the same lines, the WordPress Community is "aging out". Events online or off there's too little "youth" engaged and excited about the product.
In shoet, the pie isn't what it once was. Matt looked around the room, saw deep pockets (i.e., WP Engine) and made a go for it. That was a poor decision. Seeing himself as a cult leader who would get unwavering support from his cult (aka The WordPress Community) was another mistake. People are fatigued and enough them have stopped drinking his Kool Aid. There are pockets of support but certainly not what it used to be. Many WP people are anxious to move on from the Mattopoly.