In the book, you quote Tumblr’s CEO, who in 2010 proclaimed, “No advertising ever!” By 2013 he was openly courting advertisers.
This may ultimately be the problem with having all these current companies being venture-backed, which is that you then you have venture capitalists expecting huge returns. So these companies have to scale-up really big, and the main way to do that is to be free and to collect lots of user data. And even the most idealistic of them, and Tumblr was idealistic in its own way, they eventually say, “Well now, we have to satisfy our investors, and we have to make money, so advertising it is.”
Imagine if Tumblr weren’t so huge, but still were a similar kind of space, with similar capabilities, and a similar sort of culture—and people paid ten bucks a year. It wouldn’t be this massive company that we all talk about. But it would have a much better chance to preserve its identity, and really just to be more true and more open to its users.