Jack Dorsey's AI layoff theater and a tale of what Square could have been

Happy Tuesday.

I’m bringing you a bonus issue of The Aisle today because, as my wife has learned the hard way, sometimes I just have something to say. (The regular weekly edition will still be coming to your inbox tomorrow.)

Earlier in my career, I covered Square and its cofounder and CEO Jack Dorsey closely for six or seven years. So when I read Dorsey’s announcement on X last week that his company—now called Block—would be cutting around 40% of its staff or 4,000 employees, and the stock shot up 24%, I put my old Square beat reporter hat back on.

And especially because Dorsey’s reasoning was largely about AI, explaining that “we’re already seeing that the intelligence tools we're creating and using, paired with smaller and flatter teams, are enabling a new way of working.”

“i had two options,” Dorsey added in his capital-letter-averse post on X. “cut gradually over months or years as this shift plays out, or be honest about where we are and act on it now. i chose the latter. repeated rounds of cuts are destructive to morale, to focus, and to the trust that customers and shareholders place in our ability to lead.”

He insisted the business was on strong footing.

I had some thoughts.

But with a couple more days of reflection, I realized I had more to say. So on to the good stuff…

Back in 2015, I worked on an award-winning series about Jack Dorsey’s return to Twitter as CEO while he was also leading Square, the payments company he co-founded that revolutionized how easily small merchants could accept credit cards.

The centerpiece of the article package was a profile I co-wrote with former colleague Kurt Wagner. Dorsey didn’t speak to us for the piece, but many who worked with him did. And the quote he later told me he appreciated most came from a former employee:

“A lot of people work at Square because they really believe in him and the ethics of the company. … They choose to stay because Jack is the kind of CEO who was tweeting from Ferguson.”

The reference was to Dorsey flying to Ferguson, Missouri, near where he grew up, during the unrest following the police shooting of Michael Brown. Some at Square were frustrated at the time because the company was already navigating a negative press cycle about the company’s financial footing that Dorsey arguably made worse by pushing for the company to publish a post busting myths about Square’s business, as I reported at the time. Then employees watched their CEO show up on the ground in Ferguson.

But some of the employees understood him and his choices. And that clearly mattered for Dorsey.

Dorsey has always been a CEO who wants to be present in the cultural moment, and seen as empathetic, principled, and definitely ahead of the curve.

Which brings us to last week.