Hatching Twitter: A True Story of Money, Power, Friendship, and Betrayal

I think the core, critical sin was choosing the advertising model to begin with. Brand advertising is not like direct advertisement, which is more programmatic. It requires something like a Disney to essentially give you a favor, because the only players that matter to them are Google and Facebook. Snapchat, Twitter, everything else did not matter.... See more

In the process, though, Mr. Dorsey said he now believes that he made a critical mistake: not hiring experts to help him understand the potentially far-reaching importance of apparently small design choices.

This may just be a nicer way of phrasing Zuckerberg’s clown car comment. Twitter happened upon a once-in-a-generation shift: the Internet was changing everything about the flow of information. Twitter stumbled into such a massive opportunity that it couldn’t evolve quickly enough to ride the wave.

Santos and Nathan argued about how to use the infusion of cash. Santos wanted much of it to go to marketing; Nathan thought it should go to coders to strengthen the back end. But within six months of the funding announcement, the arguing stopped — Nathan left.