Funny enough, I'm nearing the end of Scott Berkun's "The Year Without Pants: WordPress.com and the Future of Work"[1]. It is a great read. Highly recommended for a behind-the-scene view of WordPress and their company culture.
[1] http://www.amazon.com/gp/product/1118660633?ie=UTF8&camp=178...
https://www.amazon.com/Year-Without-Pants-WordPress-com-Futu...