The Computomatix Times

Jack Dorsey is a man of contradictions.
He is the only founder to have two companies - Twitter and Block - join the S&P 500. This is an unbelievable accomplishment, surely one of the most impressive in business history.

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Twitter is a real-time broadcast from your pocket to the world. It is the global nervous system for news, politics and culture. It remains that way today despite new ownership (a true testament to the power of the idea and the network).
Square took the $1,000 payment terminal and compressed it into a $10 piece of plastic that revolutionized small business commerce.
He was CEO of both companies simultaneously. During this period Twitter was famously described by Mark Zuckerberg as a “clown car” while Block let Toast, Stripe, and Shopify steal its lunch right out from under its nose. Both companies became bloated, sprawling fiefdoms and were eventually gutted (Twitter, famously by Elon Musk, and Block/Square/XYZ by his own hand). The divided focus did not work.
It’s become fashionable over the last few years to use Jack’s track record of executional missteps to dismiss him, and his ideas, entirely.
And to be fair, it hasn’t been the prettiest few years:
He bought Afterpay at an announced price of $29B (at least he used stock for the acquisition). Block’s market cap four years later? $38B.
He bought Tidal. Tidal! I think there was a reason besides being friends with Jay-Z but I can’t remember it.
Elon cut 80% of Twitter and the team ships faster today than they ever did during the Dorsey Era.
Oh, and we can’t forget the time he turned himself into a literal blockhead.

People struggle to hold these two Jacks in their heads at the same time. And after the last few years, they focus on the execution missteps and dismiss the innovator who is able to see the future, pull it forward, and put it in your pocket before people even realize the world has changed.
What they don’t realize is that these two sides of Jack Dorsey are two sides of the same trait.
The Jack who can’t sit still long enough to rigorously run a mature organization is the same Jack looking out five years, realizing the world will be radically different, and taking the knife to his own company. The Jack that lets his companies get way too big is the same Jack who can recognize the structure is now a noose in the AI era, and cut 40% in one go while his peers cut 10% each year and call it performance management.
Introducing: Dorsey Mode
Given Jack’s track record, I listened with real interest to his recent appearance on @bhalligan Long Strange Trip, where he and Roelof Botha deconstructed what Halligan is now cheekily calling Dorsey Mode, Jack’s radical new approach to management in the AI era.
youtube.com/watch?v=YTVSwOY19Qs
I’ll be honest. When Block announced the 40% layoff, I dismissed it. You can read what I said on Twitter right after the news dropped. I indexed way too hard on “unfocused” Jack without considering “visionary Jack.”
I said it had nothing to do with AI. I was wrong.
After listening to the full conversation, I’ve updated my position. Jack is pulling forward the future again and rebuilding his company for where AI is going to be.
He’s done this a few times now, and people always laugh at him. But more often than not, he’s right. Hell, the fact that his ideas keep working despite his execution probably means the ideas are twice as powerful as we give them credit for.
So here’s my updated read on Dorsey Mode, the four parts of his thesis that I think actually matter, and why I think Jack is early and right. Again.
The Four Big Ideas Behind Dorsey Mode
1. Cut 40% now
Brian Halligan: You laid off 40 percent of your employees. You know, Ruth Porat’s got this good line—if you’re gonna eat a shit sandwich, don’t nibble.
Jack Dorsey: We’d been making changes on the edge, like going from a GM structure to a functional structure to reduce—like, putting a cap on our layers to four—me plus four—and all these small things. But if we were to really reboot and rebuild the company, would we end up where we look today? And the answer was uniformly no.And I think generally I wanted to make sure that we—if we knew that this was what our company was going to be in the future, I didn’t want to have to do it with our backs against the wall. We’re a public company, and there’s various challenges there. And other companies will probably get to this realization at some point. I don’t want to react to that.I want to be ahead of it, because then we can do it with a lot more integrity. We can do it with a lot more generosity for the people that we’re asking to leave, and even for the people that we’re asking to stay. And we’re not just reacting into something mediocre. We’re acting towards excellence. And that’s just the tone t… continue on X ↗