How does a company with no actual full time CEO, a history of losses (including a $6m loss due to a fraud scam) and a business goal of on-boarding one of the hardest markets to obtain, succeed in a new IPO? In the case of Square, the road to success is far from paved, but some believe that Jack Dorsey has what it takes to pull this off. As the market seems less keen to accept fintech IPOs, First Data being the most recent example, investors my enter this IPO with a continuous "grumpy mood".
Running a growing business is hard, especially when there are signs that the global economy you want to expand into is entering a frightening-looking slowdown. A CEO facing an unfriendly IPO market, a slowing economy, a rising tide of competition and a few recent, embarrassing snafus simply doubles down, works twice as hard. Right? What a CEO doesn't do in such a time is take a second job at another, even more challenged company. There is a good reason why Jeff Bezos didn't sign on as publisher of the Washington Post, opting instead to simply offer input and advice. Or why the more respected CEOs of tech companies – the ones that are actually making a sustainable profit – don't moonlight. Even Steve Jobs didn't run Pixar day-to-day when he held the title of CEO.