I haven't listened to the full show, but by reading this article, they sound kinda whiny towards the end. As the market leader you need to lead by example and put out quality software or risk getting buried. You have the most users? So what. You also have the most money. Figure it out.
As they rightly mention, Apple has always been more disruptive when it comes to making changes that upset people. Most of us are used to that by now. We just want things to work well with minimal clutter. iOS 9 helped quite a bit with stability, although to be honest I've mostly only been using it on devices with 2GB of RAM which also helps reduce crashing. But I don't think it went far enough—especially on the Mac side of things. And they NEED to keep the Mac users happy because those are the users building the web, designing and/or coding their App Store apps, and often telling stories. You need to keep those people engaged and happy about what you're doing to keep them coming back and building stuff for your platform and not being vocal complainers online. As a web and app UI/UX designer myself, I know that we play a significant role in pushing the narrative online through social media, sites like Medium, forums and blogs as well as word of mouth recommendations to friends, family and colleagues who trust our technological judgement.
I can see the need to push out new features every year, but that was never the way Apple used to be. Are all of these new features nice and useful? Yeah. But Apple used to take their time to get things right, even if it meant falling behind temporarily in features. Even so they're still behind in some regards. But that's the nature of the tech space. Everyone is constantly filling in ever-expanding gaps every year. Maybe it's time for Apple to say they're not going to play that game. They need to strengthen their UX, services and underlying code base.
To borrow an analogy from my photography courses, my professors would always say we need to nail our exposure first before we worry about color balancing, dodging and burning, or any other fancy things we can do to improve our photograph. Same thing goes for software. Nail the underlying structure and code efficiency before you start bolting on all the fancy bits and bobs that most people won't use as a whole but look good on a spec sheet compared to Android. Things like custom keyboards are a prime example. They're still not that good, even after all this time. If your structure can't handle it, don't bolt it on and hope for the best!