There's a really interesting write up comparing the success of Microsoft in the Windows-dominant era versus Apple in the mobile era called The Funnel Framework. It's really on point at the moment, and also mentions some other examples you'll recognise. I also was inclined to draw links with WordPress' current progress and increasing marketshare (now powering over 24% of the top 10 million websites as ranked by Alexa).
I have a lot of thoughts about the ideas raised in this article. I particularly liked this highlight:
What is interesting, though, is the impact on platforms and ecosystems of a user-first approach. iOS has maintained a platform lead, just as Windows did, but unlike Windows said lead is not based on owning the ecosystem (and thus distribution);2 rather, iOS owns the best customers, i.e. the customers who are most willing to pay. This is hardly a revelation, but I think there is a larger lesson to be drawn: success no longer depends on platforms or ecosystems; rather, platforms and ecosystems themselves depend on access to desirable customers. By extension, the companies who own that access — who own the funnel, to use a marketing term — are the ones who gain outsized influence and, in the long run, outsized profits.
Several views that could be taken here, in relation to WordPress' position with consumers and enterprise customers. You could consider WordPress in the role of Windows and Drupal as iOS when it comes to Enterprise. There's also the impact that the impending WP REST API could have on these scenarios by helping to grow the WordPress ecosystem.