No one is born knowing it all. People learn along the way, people change, people get greedy for a moment then have more time to relax once they've arrived to a comfy state, then reflect and either get more greedy or have enough head space to realize what they've done and regret. Granted, Rare are those who regret and what to do better, but yes, I can give credence to such sentiment.

It’s strange that he has apparently felt this way a long time, started Twitter as a “protocol”, was at the helm of Twitter, but now that he’s a billionaire thinks it was all a mistake. He could have made what he describes or apparently believes in but at the cost of becoming a billionaire. It’s a little too convenient isn’t it? Sounds like a billionaire just wanting to be the smartest person in the room. This is a common pattern amongst all these billionaires.

I think there is evidence that Dorsey was bothered for a long time. Scott Galloway, shareholder in Twitter and public figure, has been calling him an absent CEO for 10 years. He was largely disengaged and the board had to drag him into the room to make decisions, which many times he did not do.

Bring back Costello. At least he appeared to give a shit. Dorsey seems to thrive on the image of being a tortured and begrudging de facto CEO, a genius saddled by his creation.

I wouldn't disagree with that. His "I'm going to work/live in Africa" stunt was astounding.

Twitter could be used from devices other than a desktop PC when it launched. This was genuinely novel and drove a lot of adoption.

Specifically I believe you could tweet via SMS which is where the character limit came from.

Correct - you could also get tweets via sms

It's possible to be both successful and remorseful. Maybe when he says "protocol," he means "stayed with an open API" so third party clients could have stuck around.

It's also easy to say in hindsight too.

Were there plenty of times/chances to see the writing on the wall? Sure... but I really do think when you're in that deep, the money isn't really a factor, its the "life." Twitter ran Jack more than Jack ran Twitter.

True, cheap talk from him now. I only meant to push back against the idea that "they are locked in their business/company/VC model and can’t get out of that", which is directly contradicted in the source we're discussing.