I’ve recently been doing researches on failed open source project or relationship between an open source community and a business that went in different direction. I’ve heard about the Cloudmap and OpenStreetMap story but I haven’t been able to find all the pieces in one place. Here is my two cents to group keys elements together with link to each resources for more details.
Cloudmap was initially providing tiles for Openstreetmap. In 2010 a couple of month after their second round of funding, the CEO left the company. In 2014 the company pivot to be a content aggregator for anyone who need geo data and later decided to focus on larger account only. OpenStreetMap is not their main source of information anymore and Cloudmap team seem to not contribute actively to the development of OpenStreetMap.
This can be seen more as a failure for the OpenStreetMap community as they lost a major contributing member. From my own opinion this can be due to different long term vision between the company and the community. This case is a kind of happy ending since both actors are still kicking and alive today. However this can also be a risk if the community reject the company and the latter is not strong enough to survive by itself (the opposite can also be true).