--- title: "Jack Dorsey Defends Wearing “Love” Hat While Firing 4,000 Employees in Pivot to AI" description: "Jack Dorsey addressed his choice to wear a hat that said \"LOVE\" while decimating the workforce of his company Block." date: "2026-03-08" modified: "2026-03-08" authors: - name: "Frank Landymore" job_title: "Contributing Writer" link: "https://futurism.com/authors/flandymore" url: "https://futurism.com/artificial-intelligence/jack-dorsey-love-hat-layoffs" categories: - "Artificial Intelligence" - "Ethics" --- # Jack Dorsey Defends Wearing “Love” Hat While Firing 4,000 Employees in Pivot to AI ![Jack Dorsey wearing a cap with the word "LOVE" spelled out on it and a dark shirt is shown against a bright yellow-green background. Behind him, there is a bed with white bedding and a black object on it, as well as a standing fan on a tripod near a window. The image has a digital distortion effect with horizontal lines and color shifts.]() *Illustration by Tag Hartman-Simkins / Futurism. Source: Paras Griffin / Getty Images* Twitter co-founder and Block (formerly Square) CEO Jack Dorsey ain't your typical corporate suit. For one, he doesn't always wear them. He [brings up]() "world peace" when endorsing his favorite tech like crypto. Nobody really knows where he lives. He meditates frequently and sports a longish beard. He comes off as more New Age guru than CEO. So perhaps it was very on brand that, when Dorsey [announced he was firing 4,000 employees at Block](), he was wearing a hat that said "LOVE" on it in prominent lettering. Was the "LOVE" hat was tone-deaf? That may seem a silly consideration compared to the broader concern of Dorsey eliminating around 40 percent of his company's workforce, especially given his explanation that AI motivated the cuts. But his sartorial choices evidently angered at least one employee at a company meeting after Dorsey announced the layoffs, leading [*Wired* to ask in an interview]() if a "compassionate layoff" was indeed possible. Dorsey, ever the romantic, argued that it was. In fact, he seemed to suggest, that's exactly what he was trying to do. "I don't think it's an impossible task," he told *Wired*. "I wanted to approach the whole situation with love." "We had an all-hands where they could show me all the emotion and give me the feedback," he continued. "I believe our settlement to be generous compared with the rest of the market. I wanted to do it from a position of strength, so that we're not offering a less interesting severance package for people when our backs are against the wall." You hear that? "LOVE" is kicking someone, or four thousand someones, to the curb — while making sure they don't land on the asphalt too hard, somehow. Asked about the massive layoffs his frenemy Elon Musk carried out after buying Twitter — with more than 6,000 culled, he claims — Dorsey seemed to approve. "Twitter was a public company becoming a private company, loaded up with a massive amount of debt," Dorsey told *Wired*. "Elon could dramatically change the business model, which it needed. I'm grateful for all that. I think Twitter should have been private for quite some time." Dorsey's layoffs [stoked fears that AI was beginning to eliminate white collar jobs](). In his announcement, Dorsey explained that "intelligence" tools were creating a "new way of working" with smaller teams. Under this new paradigm, he implied, you had to stay competitive by embracing AI and leaner organizations. Experts, [and a former employee](), however, have argued that AI's shiny promises are being used as cover for carrying out decisions that are motivated by other financial factors — like over-hiring during COVID. **More on AI:** [*AI Use at Work Is Causing “Brain Fry,” Researchers Find, Especially Among High Performers*]() ## Author At Futurism, my work has often centered on bringing a sense of clarity and insight to complex topics ranging from the regulation of emerging technologies to the esoteric ideologies of Silicon Valley executives, while striving not to lose the poetic sense of awe inspired by often-obscure fields like astrophysics and quantum computing. I broke the story of CNET using AI to produce articles that turned out to be riddled with factual errors and plagiarism — a dam-breaking inflection point, as I've reported, that's inspired copycats and endless discourse while beguiling stakeholders ranging from tech giants to purveyors of spam around the web. My work at Futurism has been cited by publications including CBS News, the Los Angeles Times, Vice, Gizmodo, Engadget, the Verge, and Vanity Fair. I grew up in locales ranging from India to China, and now live in the exotic suburbs of Virginia. In my free time, I'm an avid reader of weird sci-fi literature, an aficionado of East Asian cinema, and, regrettably, a relapsed gamer. Allegedly, I’m working on a debut novel, currently untitled. ### Author social links [Bluesky]()