Phantom Interview with Groupon ...

Groupon CEO Andrew Mason

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.


  • Frank Strong

    Awesome post, Lou!

  • hoffman

    Now that’s a compliment.


    I don’t know if I captured Mason’ voice, but he did cut his entrepreneurial chops on bagels.

  • Aejin

    Nice. Enjoyed reading it!

  • hoffman


    After writing real Q&As and phantom Q&As, I find the fiction is easier.

  • Gini Dietrich (@ginidietrich)

    I love this…and you! You always make me laugh with your writing. I can actually hear Mason answering this way so you done good!

  • hoffman

    I figure I get to channel Vladimir Nabokov once every three years so he’s now back in my tickler file for a post in 2016 (though I don’t read Russian so that limits the potential fodder).

    And thanks for taking a shot at tracking down Master Mason. It all worked out.

    The coup de grâce would be if he weighed in with a posted comment. To borrow from another book, that would cross the chasm and land in the Huffington Post.

  • Janet Reiter

    Read your post. Beautifully said! You always did have a way with words. Janet

  • hoffman

    Aren’t you kind a soul.

    Now here’s a part that I didn’t share.

    Master Mason grew up in Mt. Lebanon where he started his Bagel Express business.

    I don’t know if you knew my Dad’s cousin Lenny Hoffman who’s family lived in Mt. Lebanon but I have this hunch they made a purchase or two from the Bagel Express.

  • Six Creative Ideas for Blog Posts | Sword and the Script

    […] 6. Phantom Interview with Groupon CEO Andrew Mason on His Resignation Letter by Lou Hoffman:  Of the lot here, this is my personal favorite.  When Andrew Mason resigned there was intense competition for commentary — newsjacking — and Lou took a really interesting approach. It’s an idea I’m hoping to copy sometime soon. Moreover, amid the clutter of opinions, Lou’s post ranked well in search and he was able to write about that as well. […]


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