Travel back in time with me to October, 2010. Stanford. Startup School.
Andrew Mason has been talking, sharing the origin story of Groupon, the lessons learned about entrepreneurship, the pitfalls, the joys. He is fun and engaging. You wanna like him, you wanna see Groupon succeed.
We get to the part of the talk where questions are asked and answered. He answers some early softballs. Then one brave soul stood up with a real query that only Mason could answer.
Is Groupon a sustainable business, given what we'd been hearing from merchants online?
It was as if a mask had dropped. Where once there was cheer and energy, there was now a sullenness. The man seemed affronted at the notion that his business would be challenged in this way. Despite the fact the opportunity to ask just such a question was one of the great values of a venue of this sort. Despite the fact that Groupon's sustainability had been the elephant in the room the whole time. This was right after some of the first stories from distressed Groupon merchants had been trickling out.
Petulant, absent all of his previous ebullience, Mason asserted the business was sustainable, offered no supporting details, and demanded the next question.
A good leader has the intellectual honesty to recognize their missteps and explain them, along with the remedies explored. The expectation for that is even more acute when you've been elevated to the role of mentor.
It was in that moment, his phoniness laid bare, that I decided Groupon was likely melting puppies in its basement, Mason knew it, and didn't know how to reverse the operation.