Kevin Ohashi dives into the hosting recommendations from both Drupal and WordPress, calling them out as false and with little-disclosed intentions.
Kevin conflates Automattic and WordPress, but given only Matt Mullenweg holds the keys to the WordPress.org hosting recommendations, in this case I actually don't blame him. He brings this very interesting bit from EIG's financial reports (they own Bluehost and are the largest host in the world):
Need more math? Take a look at Endurance International Group (parent company of BlueHost and many other brands)’s 10-K filing with the SEC. “During the year ended December 31, 2014, the Company made a strategic investment of $15.0 million in Automattic, Inc. (“Automattic”), an entity that provides content management systems associated with WordPress. The investment represents less than 5% of the outstanding shares of Automattic and better aligns the Company with an important partner.”
How important is that relationship? “In addition to word-of mouth, PPC and reseller and referral channels, we have also entered into strategic partnerships, such as our partnership with Google through the “Get Your Business Online” initiative in the United States, India, Africa and Southeast Asia and our strategic alliance with WordPress, which help us reach additional subscribers.” It’s mentioned as one of two partnerships that they called out specifically by name at the top of their filing. Pretty damn important.
The EIG investment into Automattic was known. Their explicit statement in their SEC filing is what's interesting: obviously they seem to have conflated WordPress and Automattic as well, and they see the “strategic alliance” as significant enough to be labeled right along side one with Google.
By most accounts I know, nobody other than Matt Mullenweg knows the deal for getting on the WordPress recommended host list. However, there has seemed to be a pattern between recommended hosts and multi-WordCamp sponsors. That said, the verbiage and openness of these deals is inconclusive at best.
I don't think Matt is personally directly profiting from the hosting page. However, some decision making process is beyond the recommendations, and they are very valuable recommendations for the hosting companies. That decision making process is totally opaque, and it should not be so.