Always great to read Tim's thoughts on the future of science and publishing. It's not mentioned in the article, but he's also invested in PeerJ (https://peerj.com/), a new open access journal that's pioneering a 'pay once for life' membership model.
More details on the O'Reilly investment here: http://blog.peerj.com/post/91251985913/exciting-times-peerj-...
(I'm not involved with PeerJ directly, but I should say that we're working with them on opening up science; I'm one of the founders of Overleaf (https://www.overleaf.com), the collaborative writing and publishing platform that grew out of writeLaTeX. Send me a message if you'd like more info.)