The response to Andrew Mason's resignation note has been generally positive, it's been described as honest, charming, and funny. It was all of those things, but it will also likely ensure that Mason won't be CEO anywhere for some time.
Mason was regarded as smart, often charming, but somewhat immature, and possibly not up to leading a business as large as post-IPO Groupon. Mason's departing letter serves to confirm much of that.
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. The fact that he was candid and honest doesn't change the numbers.
The fact that Groupon is a business that's in a huge amount of trouble won't help. If it 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.
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