Who Doesn’t Know Jack About Squaring Off With Twitter?

While the blogosphere and Wall Street have been cyberventilating the last couple of weeks over Jack Dorsey taking back the reins of Twitter, little has been said about the CEO’s other company, Square.

With Twitter’s current share price dipping below its opening IPO trade two years ago of $45.10, the last thing any one suspected was for Dorsey to go public with yet another company, while he struggles to bring Twitter out of the red. But such is the case. . . and to boot, he'll assume the role of CEO at both companies.

What’s a Square?

For those who haven't gravitated to mobile payment systems (e.g. Paypal) yet, Square was Dorsey’s invention to hit that proverbial nail square on its head. Square Register allows individuals and merchants in the United States, Canada, and Japan to accept offline debit and credit cards on their iOS or Android smartphones or tablets.

The software app supports manually entering the card details or swiping the card through the Square Reader, a small plastic device that plugs into the audio jack of a supported smartphone or tablet and reads the magnetic stripe. On the iPad version of the Square Register app, the interface resembles a traditional cash register.

Not letting any grass grow beneath his feet, on October 14 this year, Dorsey filed documents to go public with Square. Since Square generates the vast majority of its revenue by charging brick-and-mortar businesses a transaction fee which is typically 2.75 percent every time a customer pays with credit or debit card, the upside of Dorsey’s new company could be exponential over the next few years.

Is Twitter Fixable?

So with Square moving at ram speed, and Dorsey re-accepting his CEO role at Twitter -- one has to wonder if there will be enough “Jack Time” to go around, or will Twitter not get the much needed attention its shareholders are clamoring for?

Well, the jury is out on that one. Twitter will report earnings on October 27, but it may be too soon to see any changes aside from the confidence factor the financial industry holds in Dorsey. That coupled with the fact that as soon as Dorsey took back his old chair, he did announce company-wide layoffs to tune of over 300+ employees.

Based on the early reports, Dorsey’s Silicon Valley colleagues think he can do it - it does seem he's headed in the right direction.

According to Kurt Wagner at re/code, “so far he seems to be making it work . . . but as with all companies, there will be challenges, and if that happens with both companies at the same time, we’ll see which one is not getting enough ‘Jack time.’”

From Where I Sit . . .

From my vantage point, however, I’m rooting for this double-threat CEO to knock it out of the park. While I’m not a financial wizard, I did know enough to sell my Twitter stock at $59 (when things went south earlier in the year) . . . but now that Dorsey is back at the held, today (just before writing this blog,) I purchased shares at $30 . . . and will also consider purchasing some Square, when it goes public.

It’s a gamble — for sure — but from where I sit - I’m reminded of Steve Jobs doing something similar back in the late 1990s with Apple . . . so while not a sure bet, it’s a gamble I’d like to square off with.

Will keep you updated in future posts, whether or not I also hit the nail on its proverbially head with this one. Your thoughts, readers . . . are you considering taking shares in both companies as well, or do you think Dorsey bit off more than he could chew?