Unsolicited Advice for Jack Dorsey on His Rumored Re-Tweet, Courtesy of Himself

Mining clues from Jack Dorsey’s inner life, just as he seems poised to return in a larger capacity to the company he founded, Twitter.

Jack Dorsey


Several recent reports suggest Jack Dorsey, who helped spawn Twitter years ago, could be returning to a much larger role in the company. Dorsey had been ousted from his role as CEO, supplanted by Evan Williams, and Dorsey went on to pursue a new venture with Square, the mobile payment company. But now that Williams has stepped down as CEO, yielding that position to Dick Costolo, Dorsey has become more involved at Twitter–and might be coming on full-time as something like Chief Product Officer.

All of which makes Vanity Fair‘s April profile by David Kirkpatrick very timely. We studied Kirkpatrick’s profile, which you should read in its entirety here, for insights into why Chief Product Officer could be an ideal position for Dorsey–and why he might succeed or fail. If Dorsey wants to keep Twitter strong, the subject he might do best to study is himself. So we at Fast Company have taken the liberty of imagining ourselves to be Jack Dorsey’s therapist, spinning expert advice out of things the man himself has said:

1. Keep things simple.

Buried about a third of the way into the profile is what seems like the core of what has made Dorsey successful (very successful–he might be worth something like $300 million). “Making something simple is very difficult,” he says at one point, adding that he learned much from the precision and control in the work of his ex-girlfriend Sofiane Sylve, a ballet dancer. Twitter’s main virtue is its simplicity–its clean interface, its neat design, its constraints that enforce brevity. Which is why the notion that Twitter might need a “Chief Product Officer” to begin with makes us a tad nervous. The New York Times today makes the sound point that “mission creep” could be damaging to services like Readability and Instapaper, whose whole raison d’être is to keep things simple. Dorsey should avoid complicating things if he returns to Twitter.

2. And don’t get distracted.

Though Kirkpatrick writes that Dorsey devotes “most of his waking hours” to his two companies, and that he has a singular ability to stay focused, we also learn that Dorsey, in the past, has been all over the place. He gave up coding for a while to pursue a career as a botanical illustrator. He spent thousands of hours becoming a certified massage therapist, only to learn that San Francisco didn’t really need any more of those. To be well-rounded is a fine thing, to be sure, and a venture capitalist who invested in Square praised Dorsey’s “ability to blend ideas.” But there’s a fine line between being well-rounded and being unable to commit.


3. At the same time, follow your gut.

One thing that elevates Dorsey among his peers (his few, multi-millionaire, young-and-fabulous-tech-genius peers) is a strain of utopianism that appears to govern the way he views the world. Fundamentally, he sees both Twitter and Square as experiments in democracy. “Jack’s biggest insights have nothing to do with technology,” says one collaborator, Greg Kidd, in the Vanity Fair piece. “It’s always a democratization machine … Even the way he talks about Square is about social justice.” A philanthropist acquaintance says of Dorsey that “at the core of his being, he really wants to make the world a better place.” There’s a reason why what, on the face of it, is a stupid little website (what was your first reaction to Twitter?) has conquered the world. As long as a certain civic-mindedness always animates Dorsey’s work, he’s likely to remain good at what he does.

4. But don’t run for mayor of New York City yet, please.

The profile’s biggest revelation, perhaps, is Dorsey’s designs on the job currently held by Michael Bloomberg. Yes, that’s right, “his ultimate aspiration is to become mayor of New York.” He even got a meeting with Bloomberg to talk about it. Bloomberg advised him to make a lot of money. The idea to enter politics is all well and good, perhaps, and it would be exciting to have a mayor who once used to wear his hair in dreadlocks and has a giant tattoo of the integral symbol running the length of his forearm. But before rolling up his sleeves to tackle America’s most populous city, Dorsey–who is said not to have managed Twitter so well back in the early years–should try cutting his teeth a bit more managing one of the Internet’s most populous websites.

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[Image: Flickr user TCDisrupt]


About the author

David Zax is a contributing writer for Fast Company. His writing has appeared in many publications, including Smithsonian, Slate, Wired, and The Wall Street Journal.