Jack Dorsey, Charlie Chaplin of Technologists

I love this Wall Street Journal profile of Jack Dorsey, co-founder of Twitter and Square. The Journal likens him to Charlie Chaplin of technologists, and based on what I’ve read about him, the analogy seems apt:

[Jack Dorsey] works standing up at an immaculate, clutter-free table in the center of the wide-open office, typing alone on his iPad, easily accessible to colleagues who can informally sidle up and ask him questions. His daily uniform includes dainty Repetto shoes from France (because, as he recently tweeted, they are “light” and “graceful”) and special open-collared shirts, the provenance of which he refuses to identify (“halfway between a Nehru and a priest’s collar,” as he describes them). This allows him to convey enough formality for meetings, yet frees him from the constriction of wearing ties. He encourages midday strolls outside Square’s offices as a means of inspiration. He leads groups of employees on exploratory excursions to museums or across the Golden Gate Bridge.

A man of widely varied interests, Dorsey is a genuine eccentric—not a mere collector of affectations. He treats his obsessions more as callings than as hobbies. When young, he studied botanical illustration under the tutelage of a master at the Missouri Botanical Garden, gazing for hours at the contours of gingko leaves. He later became fascinated by bespoke denim and enrolled in fashion design classes. Perhaps most bizarrely, he devoted himself for a solid year to the art of massage therapy, after dealing with sore wrists from too much coding. “I was ready to do massage for the rest of my life,” he says. “I tried to convince a nightclub owner in St. Louis to let me give people chair massages at the edge of the dance floor, wearing all white clothes and white clogs. He thought it was a terrible idea, so I went back to programming.” To protect his wrists, he trained himself to type in Dvorak—a keyboard alignment that is ergonomically superior to Qwerty.

Dorsey delves deeply and intensely into whatever piques his curiosity, on the theory that innovation happens when disparate thoughts mesh. “It’s important to demystify the term. Innovation is just reinvention and rethinking. I don’t think there’s anything truly, organically new in this world. It’s just mash-ups of all these things that provide different perspectives—that allow you to think in a completely different way, which allows you to work in a different way.”

One of the most fascinating men in Tech, I appreciate Dorsey’s curatorial ability:

Thus he carefully curates the cultural intake of his employees, in hopes that unfamiliar concepts might be distilled into something new. It’s why he screens films: Modern Times for its economy of expression; Bullitt for its stark, empty compositions; Willy Wonka & the Chocolate Factory for its depiction of a company that packages delight and surprise.

In a prominent spot near Square’s welcome lobby stands a communal bookshelf where employees place reading material for their colleagues to peruse and borrow. Most titles lining the shelves cover subjects you might expect at a high-flying tech startup: inspirational CEO biographies, trend-gazing futurist tomes and guides to effective management technique. And then there are books placed on the shelf by Dorsey. He offers up Wabi-Sabi for Artists, Designers, Poets & Philosophers—an explication of the Japanese concept of serendipitous beauty. He suggests Ernest Hemingway’s The Old Man and the Sea for its concision. (Papa Hemingway might have thrived under Twitter’s 140-character constraint.)

Read the whole thing.

Jack Dorsey

Having redefined the communications and payments industries, Dorsey wants to tackle health next. I can’t wait to see what he comes up with. It’s bound to be brilliant.

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