Jack Dorsey needs a drink, but that drink should probably be coffee, not a cocktail. Today, the board at Twitter tapped him to lead the company he co-founded and has led as interim CEO since June.

The news comes as no big surprise. Some investors have publicly supported Dorsey for the role he took on an interim basis after Dick Costolo stepped down in June. And he’s a popular choice both inside and outside the company. And yet, the board said in June that it would not name a CEO who could not make a “full-time commitment” to the job. Given that Dorsey also is the CEO of Square, you’d think that would have put him out of the running.


“We looked at many (many, many) other options. We weighed them seriously,” Twitter cofounder Ev Williams, who served on the board’s search committee, wrote on Medium. “We also discussed ad nauseam the challenges of Jack doing both his CEO jobs at once. I honestly didn’t think we’d land on Jack when we started unless he could step away from Square. But ultimately, we decided it was worth it.”

So Dorsey gets to keep both jobs. This is not completely unheard of in Silicon Valley; in fact, founders are seen in some ways as the person who can save their babies. Steve Jobs simultaneously led Apple and Pixar at one point. (“It was rough, really rough, the worst time in my life,” Jobs said of the time.) Elon Musk sits in the big chairs at both Tesla Motors and SpaceX. Looking beyond Silicon Valley—yes, there is a world beyond the Valley—Sir Richard Branson leads the hydra that is the Virgin Group.

But the question remains: Does he have what it takes? Dorsey, who was ousted as CEO for, among other things, poor leadership along with the cavalier attitude that saw little wrong with leaving work early to do yoga, will need to channel his inner Jobs. Or Musk. Or even Branson. As Re/code has written, Dorsey’s time at Square may have prepared him for the challenges at Twitter.

The problem is, that may not be enough. Both Twitter and Square need a lot of help. Dorsey must reinvent Twitter to make it something regular people need, understand, and use (à la Facebook), while simultaneously guiding Square through an IPO and ensuring that its products remains innovative and in high demand.

Two Companies, One Dorsey

As a business, neither Twitter nor Square is totally secure. For the past year, Twitter has struggled to expand its user base and increase ad revenue. In its last earnings call—over which Dorsey presided as interim CEO—the brass made it clear to Wall Street that it would take time to do this. Non-users still don’t get Twitter, they said. Twitter needs to make it clear why the product is both needed—and invaluable. Twitter needs to, for better or worse, recast itself—and it needs to do so while keeping its current powerusers happy and unwilling to leave.

Meanwhile, financial services startup Square has gone from serving up innovative payments processing products to, well, competing with tech giants and startups alike. Amazon released its own card reader last year. Apple has Apple Pay and Google has Google Wallet. Myriad financial services startups offer loans to individuals and small businesses and let users send or receive cash. Square reportedly has been planning to file an IPO since earlier this year, but has yet to do so. The company may need to go public if it is to continue growing, but it also must remain dominant in its field as others encroach on its turf. It needs a hell of a CEO to do so.

So… yeah. Dorsey has a lot on his plate. The way we see it, both Twitter and Square need a whole lot of love—and even more ingenuity. Can Dorsey do it? He seems to have shepherded several partnerships at Square and Twitter in just the past few months. Twitter, in particular, has been actively experimenting with new products, some of which could roll out soon. And, if all goes to plan, Square will file for an IPO by the end of the year.

Like Jobs and Musk, Dorsey might need a little bit of luck, hard work, and a whole lot of genius. Unlike the other two, he has at least one thing in his favor—Twitter and Square’s offices are only a block away from each other.

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Someone Buy Jack Dorsey a Coffee. He Has a Whole Lot to Do