By: Dipak Krishnan, Contributor


Jack Dorsey’s recent appointment as CEO of Twitter makes him a unique man in an area chock-full of them. Silicon Valley is notorious for housing all kinds of eccentric characters pursuing their own entrepreneurial dreams. But in the Valley, success is king. It’s hard enough to succeed with one company. Most companies fail for a whole host of reasons. But now, at a crucial moment in time for Square, Dorsey is CEO of Twitter AND Square.

In addition to the insane time requirements that running both companies will require, one need only look to history to see how difficult it is to run two successful companies. Elon Musk, who runs Tesla and SpaceX and sits on the board of SolarCity, and Steve Jobs, who ran Pixar as well as Apple, are two rare examples of men who were able to succeed at running two companies at full competency. (Jobs sold Pixar to Disney for around 7 billion dollars).

So where does Jack Dorsey see himself moving?

In one word: forward. If Dorsey is going to follow in the footsteps of entrepreneurial greats like Elon Musk, he’s going to be working a lot. Musk is notorious for his 100 hour work weeks in which he sleeps exactly 6 hours a night while juggling the demands of his companies. Dorsey doesn’t have a perfectly similar situation, but he’ll have to deal a good amount of time to a stagnating Twitter.

After Twitter’s IPO two years ago, the social network has fallen behind its competitors Facebook, Instagram, and Snapchat. Twitter still has 300 million users, but its user growth has hit a plateau. It is lagging behind Instagram and Snapchat in users, as both have over 1 billion users.

One can make the case that Facebook’s own social network has ossified, but the company’s astute purchases of WhatsApp and Instagram allow to keep its predominant position in the marketplace. Unlike Instagram, Twitter is struggling to turn its massive userbase into an effective space for companies to market their products.

Snapchat’s story feature allows companies and news-based services a tool to market their products to wide ranges of people. However, Twitter’s promoted ads don’t receive the same amount of clicks from Twitter users. To give an accurate picture of Twitter’s struggles, it’s stock price was around $44.26 per share at the end of its first day as a traded stock. Now, Twitter’s stock price is languishing at around $26. Dorsey is reinventing Twitter’s system by adding the ‘moments’ feature into the network in hopes to emulate Snapchat’s success with news-based advertising. But Dorsey needs to kickstart user growth and interest in Twitter again to push the company into new heights.

Twitter is at a precarious point in its timeline, but Square may be in an even more important juncture in time. The mobile payments company has an estimated 2 million users accepting credit cards through its encrypted payments service. Confidentially, Square filed its papers for an IPO later this year though the company has yet to confirm this publicly. Taking Square through its IPO and dealing with Twitter’s struggles could threaten to overwhelm Dorsey. However, Dorsey’s return to Twitter is one of the most talked about events of the year in Silicon Valley. Rarely does the Valley get excited as it does when a founder returns triumphantly to his brainchild to lead it into his idea of the future. In the end, I think Jack Dorsey is one of the few men capable of leading Square and Twitter to success simultaneously. Let’s see how he performs.