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".