I get your point, but seriously, go read Nick Bilton's book about the early history or Twitter. From the time of Odeo to Jack coming back, none of the people in charge of this company or the board had a consistent idea of what they were building, an appropriate roadmap to get there, or how to monetize effectively relative to other social networks. This happened for years.
Square is amazing, but a B2B, modern Point-of-Sales for SMBs is an entirely different beast than a free, B2C social network. Jack can be great at one, and terrible at the other, at the same time. These are not related.
I'm not really sure what you're trying to argue here. The simple fact is the guy created two deca-corn companies. That basically completely invalidates any ex-post arguments by some author about the quality of his management. What I mean by that is that if a thing succeeds spectacularly, maybe you should question your premises before questioning its methodology. The process that appears to you to be disorganized and aimless produced Twitter. It obviously did something right.
I don't know what I'm talking about, but judging from the fact that Ev Williams founded or co-founded Blogger, Twitter, and Medium, perhaps he was the real visionary behind the idea. That's three different "write stuff online and share it" startups. He clearly understands social media and blogging and micro-blogging. Maybe Jack is more of the 'biz guy'?
My take on the founding of twitter is that you had a bunch of people and no clear leadership, and that different people had different opinions of what twitter should be. That ambiguity has undermined the platform from day one, no focus, no clear mission, no clear plan on how to spend their money.
Square is amazing, but a B2B, modern Point-of-Sales for SMBs is an entirely different beast than a free, B2C social network. Jack can be great at one, and terrible at the other, at the same time. These are not related.