Can Jack Dorsey Lead Two Companies?

On Oct. 5, Twitter Inc. announced that Jack Dorsey, one of the microblogging service's co-founders who had been acting as its interim CEO, would stay on as permanent CEO. 

The move is largely unsurprising, if only for one other fact: Dorsey is also CEO of mobile payments company Square Inc.

Running two companies isn't easy. And although it's rare, it's been done before. Steve Jobs once ran both Apple Inc. and Pixar. Elon Musk is currently running both car maker Tesla Motors Inc. and SpaceX.

But is running two companies at the same time a good idea?

Dorsey is in an especially challenging spot, as both Twitter and Square have significant challenges and changes.

Twitter is challenged by increasing investor concern about new products driving stagnant user growth, while Square is gearing up to go public. Dorsey is expected to play a large role in Square's IPO roadshow to the public leading up to the offering  a big time commitment.

Thankfully, Square and Twitter headquarters are located a block away from one other, so Dorsey shouldn't have any trouble with the two-minute commute between jobs.

According to talent management and business experts cited in various news reports on the subject, the task of running two companies at the same time comes down to delegation and strong senior leadership support. But to some, the arrangement doesn't always work out in the long term.

"These are short-term solutions," David Yoffie, a Harvard Business School professor and an expert on corporate strategies, told the San Jose Mercury News. "They are only viable when you have very strong operating management in ideally both companies, but at least one of the companies, so that the CEO is able to step back and focus attention where attention is required."

"It takes the right person and the right backdrop [to be a CEO of two companies at once]," Brad Slingerlend, portfolio manager of Global Technology strategy at Janus Capital Group Inc., told The Wall Street Journal. "If both were moving in the right direction, it would be easier to row two boats. If one or both was more of a turnaround situation, investors might have more questions about that than about two companies on autopilot."

What do you think?