Phantom Interview with Groupon CEO Andrew Mason on His Resignation Letter

Andrew Mason’s resignation letter last week reflected the best of storytelling in business communications.

With this in mind, I tried to track down Mr. Mason to take us behind the curtain in how the letter came about.

Unfortunately, he proved elusive.

If Mason had agreed to an interview, I suspect the exchange would have gone something like this:

Lou: First, let me say I loved the letter. Finally, a CEO who actually shared what was on his mind. But aren’t you worried that the self-criticism will come to haunt you, and you’ll never work this town again?

Andrew: Fortunately, Chicago isn’t the only town in the country.

Lou: You know what I mean.

Andrew: What did I write that wasn’t public knowledge? The stock tanked after our IPO. There’s no recovery in sight. We’ve lost our way.

Lou: How do you respond to the people who say you never belonged in the CEO role to being with?

Andrew: You mean running the Bagel Express in high school didn’t prepare me for leading a public company with a billion-plus market cap?

Lou: Basically.

Andrew: All I can say is you don’t know until you try. The Board gave me leeway to scale the business. I didn’t hit the metrics. They fired me.

Lou: The dreaded F word. The opener in your letter about spending time with your family, then counter-punching with those four words, “I was fired today,” was fresh. How did you come up with that?

Andrew: Why does business always have to be so serious? I failed as CEO of Groupon, but it wasn’t because I lacked a sense of humor. It’s such a joke that every time a Board fires its CEO, the decision gets rationalized with things like wanting to spend time with the wife and kids. C’mon. People aren’t stupid. They fired the dude.

Lou: Given that part of the Groupon experience comes from the clever copywriting, I thought your letter to the troops carried a fitting narrative.

Andrew: Thank you. No one picked up on that nuance.

Lou: Have you considered writing a book?

Andrew: Absolutely. I already have the title, “Good to Funny.” I checked, and Collins hasn’t trademarked the title.

Lou: Nice. I do want to come back to this theme of business always being so serious. Your letter to shareholders wasn’t exactly a knee-slapper.

Andrew: I’m not following.

Lou: The same humanity and levity that made your farewell letter so great is MIA in the shareholder letter.

Andrew: Let me ask you a question.

Lou: Go for it.

Andrew: Have you ever been involved in drafting the CEO letter for an annual report?

Lou: No.

Andrew: Sausage-making is a prettier process. That shareholder letter went through more than 20 revisions, and that was just the attorneys. They squeezed the life out of that letter until it rang vanilla. I had to fight to use the phrase “bumpy road” instead “volatile market conditions.” And the idea of writing that “consumers love Groupon,” you would have thought I was suggesting a sequel to Lolita.

Lou: The attorneys didn’t get to look at your final letter.

Andrew: You serious?

Lou: Thankfully, not.

As I shared in The New York Times, the amount of attention heaped on Mr. Mason’s farewell letter says something about the state of executive communications.

Simply being candid with a touch of levity not only differentiated Mason’s letter, but probably put it in the CEO Letter Hall of Fame.

I’m not holding my breath that this starts a trend. Years of muscle memory are tough to change.