There's something charming about Andrew Mason's goofiness. "I feel like clout is something that builds up on your teeth," the Groupon CEO once told Today in response to a question about his influence. But with two top lieutenants out the door in as many weeks, you have to wonder if the antics are starting to grate.

First went Groupon's sales chief, who was replaced amid chatter that the company had a weak cash position. Now comes word that Mason has lost his head of PR, reportedly over frustration at how Mason flouted SEC "quiet period" rules by circulating a lengthy, defensive internal memo addressing the cash chatter.

In it, Mason said Groupon's sales, which "rapidly decelerated" in the last quarter, are up so far in August; that the company has long planned to reduce its marketing expenses to move toward profitability; and that Groupon is not alone in having payables that exceed cash — Amazon and Wal Mart do, too.


Of course, Amazon and Wal Mart are also profitable companies with hard assets like warehouses, stores and inventory, all of which Groupon lacks. But set that aside. What they also have are thick skinned CEOs who can hold their tongues when need be like, in Amazon's case, during its own tech IPO quiet period.

Mason is supposed to be staying quiet, too, and there's no loophole in SEC rules for "internal memos" that are conveniently leaked to the press. Or at least that's what Mason's own PR chief apparently thought.

Yes, it's somewhat endearing that Mason has self deprecatingly referred to Groupon as "like the N-Sync of websites... It's not like we're the best thing ever," or "kind of stupid. Like, I've had way better ideas, way cooler ideas." And it doesn't seem particularly harmful when he makes underwear yoga videos (above), descends imaginary stairs or a jokes about running a monkey rental business. But as The Wall Street Journal has written, investors see these antics and yearn for reassurance that Mason actually takes Groupon seriously as a business. Especially when he's diverted so much of Groupon's capital into his own bank account so early in the game.

In that jittery context, Mason's memo leak lends the appearance that his irrepressible side is perhaps turning into a reckless streak. When you want people to trust you about money, how you say something is as important as the actual words. Mason said his piece, but he said it wrong.