Oct 19, 2015 ยท 6 minutes

I’ve been following Jack Dorsey’s recent career moves with the rapt, but fleeting, attention one might pay to an escaped helium balloon.

I’ve read some of the coverage, including here on Pando, suggesting that Dorsey’s decision to split his time between Twitter and Square could harm both companies. And of course, like you, I’m far beyond sighing point at the comparisons being drawn between Dorsey and Steve Jobs. By now the only person not tired of those comparisons is Dorsey himself — even Jobs has stopped spinning in his grave.

Here’s what I haven’t read, or heard: A single person at Square bemoaning Dorsey’s half-departure from his job there. When Jobs announced, due to declining health, that he’d have to reduce his role at Apple, the streets were filled with weeping, tooth-gnashing Apple employees. “How can we go on without Steve?!” “Won’t somebody please think of the children!” Certainly, had Apple been planning an IPO at the time of the announcement, those plans would likely be scrapped or certainly delayed.

At Square: Silence. No weeping or wailing and certainly no signs that the company is changing any of its plans to reflect the fact that their boss’ attentions are occupied elsewhere. Quite the opposite, in fact. This past week, Square filed its S-1, ahead of an IPO. The prospectus contained only the briefest acknowledgment — one single sentence, buried below many, many other risk factors — that the company was lacking half a captain.  

Jack Dorsey, our co-founder, President, and Chief Executive Officer, also serves as Chief Executive Officer of Twitter. This may at times adversely affect his ability to devote time, attention, and effort to Square.

“...may at times...”

To my admittedly untrained ear, this screams something loud and clear: Jack Dorsey wasn’t really doing much of value at Square. That for all its cute rounded hardware, dot commy name and statements about “creating more inclusion and greater equality in the global economy [by] empower[ing] people with beautifully simple tools”, it is ultimately a boring old financial services company that’s pivoting into an equally dull small business software company. In fact, it’s the flashy Jack ideas -- that weird wallet app, the Starbucks partnership -- that have failed most dramatically.

Square’s day-to-day focus doesn’t need a soi-disant “product visionary” like Jack Dorsey. It needs someone capable, but dull as ditchwater -- think Stanley Friesen in Hart to Hart -- who gets a kick out of the mundanity of reducing fraud by a fraction of a percentage every year or “onboarding” new merchants as quickly and painlessly as possible. In fact, one might argue, Dorsey’s Steve Jobs parody could be a royal pain in the ass to folks trying to dot the I’s and cross the T’s ahead of an IPO.

Certainly Dorsey is happy to project the image of a man with plenty of time on his hands. Despite apparently running Square, and sitting on the board of Disney, he has somehow found the time to lobby for the Twitter job (during which lobbying campaign he must have convinced the board that he has plenty of free time). Steve Jobs famously explained that his turtleneck and jeans uniform ensured he didn’t have to waste time deciding what to wear. Dorsey is almost as famous for his image changes as he is for his business activities. Today Jack has a long beard! Today he’s shaved his head! Today he looks like a Bond villain who’s lost his cat! Hours after Dorsey was confirmed as Twitter’s new CEO, Business Insider published what, to them, constitutes a deep-dive into… Jackie D’s latest makeover.

"The famous facial hair was trimmed back to the point where it was difficult to determine whether it could best be described as a small beard or simple stubble. For a coiffure, Dorsey went with an elegant yet versatile fade."

“An elegant yet versatile fade.” Remember that one, future Dorsey headline writers.

If you can judge how busy a professional writer is by how much time he spends updating his own website (daily personal blogging = poverty line), surely we can also infer how vital Dorsey is to Square’s operations by how much time he spends reimagining his hair and clothes.

For Square, none of this bodes ill. If Dorsey is no longer vital to the company’s long-term success, then there’s no reason to think his shift to part time status will have any meaningful impact. That would explain the lack of distress shown by staff or senior management when he returned to Twitter.

For the board, shareholders and staff of Twitter, however, that silence should worry them greatly. If Square will be fine with or without Jack Dorsey, then it raises the question: What exactly is his value-add? Aside from a few breathless headlines, the disappointing launch of “Moments,” and a stock price that continues to drag along the ocean floor? Are we seriously supposed to believe that the guy who was fired from Twitter before going on to be utterly dispensable at Square is going to suddenly come into his element the second time around? Or, forget Steve Jobs returning to Apple, is this more like Pete Best returning to save the Beatles?

There’s one person to whom no one has compared Jack Dorsey, and that’s Mark Zuckerberg. This despite the fact that Twitter today has much more in common with Facebook than it does with a hardware company from a previous era. Ignore the obvious reasons that there’s no comparison – a less obvious one is Dorsey’s track record with acquisitions, compared to Zuckerberg’s.

According to press reports, it was Dorsey who let Zuckerberg steal Instagram out from under Twitter. Meanwhile, the deals Dorsey did champion – chiefly Vine and Periscope – have been interesting but haven’t come close to saving, or even changing, the company. And let’s just draw a veil over Frontback and pretend it didn’t happen.  

Therein lies the difference between a “product genius” at a small company, and the same role at a large public company. Imagine if Facebook’s acquisition strategy hadn’t been so successful. For one thing, teen users would be long gone. And forget all those eyeballs fixed on four of the five largest mobile messaging apps. Investors would still be spending sleepless nights worrying about the company’s mobile strategy.

And yet we’re really to believe that Dorsey – half of Jack Dorsey, to be precise – is really the guy to pull off a miracle at Twitter. This time. That he’ll finally find his focus, his reason to be, and – let’s be blunt – his competence.  

I guess more unlikely things have happened in Silicon Valley (probably, I imagine). But a word of advice for Twitter employees and shareholders: If, between now and Christmas, you see Dorsey heading for a fancy hair salon, you might want to run for the exit.