The team sitting around the table at Groupon’s Chicago headquarters in the early spring of 2011 were some of the brightest minds in technology and business. Marc Andreessen, the man who created the modern web browser and Silicon Valley’s hottest venture capitalist. Mary Meeker, Wall Street’s internet oracle. Howard Schultz, the chairman and CEO of Starbucks. And of course, the team from Groupon: the precocious chief executive Andrew Mason, its hard-driving chairman Eric Lefkofsky, and its European czar, Oliver Samwer.

At issue was whether or not the company should file to go public. Andreessen, Meeker, and Schultz recommended against it. The company still needed to mature, to perfect its core offerings. The mantra at Groupon was that it was building the operating system for local commerce, but the technology at that point, according to sources*, was still largely aspirational. Groupon's developers and engineers were too busy putting out fires to build out a great platform. What was really driving the company forward was its ever-growing sales force, which had a total headcount of 126 at the start of 2010 but had grown to over 5,000 by April of 2011.

Mason was on the fence. He wanted Groupon to be a big success, and styled himself as a product visionary, a young Jeff Bezos. But he also wanted to protect the quirky culture he had built at the company and retain the independence that was the hallmark of his character.