Jack Dorsey says his biggest regret is that Twitter was a company at all

Jack Dorsey might be out of the picture at Twitter these days, but he's still waxing philosophical about the company. In a reply to a tweet asking about his biggest regrets (paired with, sigh, anecdotal claims about political bias on the platform) the company's co-founder and former CEO offered the grand observation that he wishes the company had never existed at all.

"The biggest issue and my biggest regret is that it became a company," Dorsey tweeted.

If you've not heard Dorsey on one before, the idea that Twitter should never have been a company might sound strange. But he doesn't really mean that the project should have never existed, more that if he could rewrite history he would have (supposedly) steered Twitter toward being a protocol, not a company. "[I] don’t believe any individual or institutions should own social media, or more generally media companies," Dorsey tweeted back in April. "It should be an open and verifiable protocol. Everything is a step toward that."

Of course, Dorsey made absolute bank when Twitter went public in 2013, but tech billionaires always do seem to have these hypothetical regrets, don't they? (To Dorsey's credit, at least he's doing something worthwhile with a big chunk of that cash.)

Replying to a more reasonable follow-up question from Jane Manchun Wong, Dorsey reiterated that he wishes Twitter had become an open protocol, not a company. The company has certainly struggled to please investors, chart a growth course and even offer a definition of what exactly its mission is over the years, in spite of becoming a real-time utility for disseminating information that many people, world leaders among them, deem essential.

Is it Monday morning quarterbacking if you're criticizing your own decisions, years after making a fortune from those same decisions? Whatever it is probably isn't very productive, but nonetheless Twitter's beardy esoteric guru continues to tweet through it, even as everybody else left at Twitter navigates the company's most tumultuous phase yet.

Dorsey's dream isn't dead though, it's just more likely to be realized through a project parallel to Twitter proper. Even with the little blue bird stuck on Elon Musk's self-driving rollercoaster, Twitter's open source spinoff Bluesky is still working toward the dream of decentralization, and its plans for a totally open social networking protocol appear to remain intact amidst the chaos.

In spite of his lofty ideals, Dorsey threw his weight behind Musk's acquisition bid earlier this year. But if @jack values transparency and an open environment for the social platform he co-created above all, a tech executive infamous for making misleading claims, concealing company data and flinging NDAs around is a strange person to buddy up with, to say the least. Of course, Dorsey stands to make many hundreds of millions from the deal if it closes, though all of that is very much up in the air as Musk and Twitter head to court in October.