Andrew Mason's Departure Letter Was A Bad Career Move
You don't see many letters like his because most departing execs want to work again in relative short order. Unless you have the financial comfort that lets you take a few years off, you tend to avoid making Battletoads references after being fired from the public company you helped build from a startup. Mason didn't even attempt to keep it private, immediately publishing the memo publicly.
Mason could either be ready for a break after what had to have been a trying couple of years, or alternatively, he could have made a poorly considered decision on what had to be an emotional day.
Leslie Kwoh at The Wall Street Journal spoke to talent executive Kathy Gersch, who argues that Mason could get away with it:
“Andrew Mason is an entrepreneur. He is not looking to be politically correct and position himself for the next big corporate job,"
His frankness, she adds, might appeal to an employer who is “looking for a leader not afraid to break the rules.”
That seems overly optimistic. Few companies are going to be willing to take that gamble. Breaking the rules is fine in a CEO, but Mason's track record at the top of Groupon speaks for itself. His candidness and honesty don't change the numbers.
Groupon's financial troubles won't help. If the company recovers in his absence, it's evidence that Mason was a major part of the problem. If it doesn't, he rapidly scaled a fundamentally flawed business, which could hurt a lot of investors.
Writing this kind of resignation letter is the kind of luxury you only have when you're 32 and have a fortune that, while likely diminished, is still considerable. Mason may very well start another company, but he'll have to prove he's grown up first before most people would consider funding or hiring him.