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Why former Groupon CEO Andrew Mason regrets telling everyone he was fired

Mason’s latest startup, Descript, is a “word processor for audio” aimed at making it dead simple to edit podcasts and other spoken-word recordings.

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Descript CEO Andrew Mason
Descript CEO Andrew Mason
Courtesy Andrew Mason

When he was at Groupon, Andrew Mason was known for being more honest and blunt than other tech CEOs — a trait that extended to 2013, when the company he co-founded fired him. Four years later, he’s not so sure it was a good idea to transparently announce that to the world.

“The only thing I’m doing in my mind at the time, by pretending I wasn’t fired, is deluding myself,” Mason said on the latest episode of Recode Decode. “But here’s the reason it makes sense [to lie]: Now, every time anybody writes about me, it was always like, ‘ousted Groupon CEO starts a new company.’”

The “ousted” entrepreneur told Recode’s Kara Swisher and The Verge’s Casey Newton that he is no longer working on his first post-Groupon company, Detour, although he declined to go into specifics about its future. But an internal audio-transcribing project at Detour spun off into his latest venture, the “audio word processor” Descript, which publicly debuted this week with $5 million in funding from Andreessen Horowitz.

You can listen to Recode Decode on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.

On the new podcast, Mason told stories about his “surreal” time at Groupon, including the time he tried to dress an employee up as a terrorist and almost surprised Michael Bloomberg with the gift of a horse. He also reflected on why his persona was so consciously different from his peers in the late-2000s tech scene.

“The fact of the matter is, there’s an incredible amount of luck,” Mason said. “There’s a lot of entrepreneurs out there who are way smarter and more capable than I am, that have never had the kind of success of Groupon.”

“I was never comfortable with the amount of adulation, all of that, on the way up,” he added. “I responded to that aggressively, by going out of my way to seem stupid.”

But his shoot-from-the-hip style didn’t please Wall Street as much as it pleased the Silicon Valley press. After what happened at Groupon, he has no interest in running a public company again, he said.

“What I wasn’t prepared for was the degree to which you enter the big leagues and it’s an entirely different game once you’re a public company,” he said. “I just had this incredibly naive attitude: ‘Oh, I’ll just be myself and I’ll keep doing what I’ve been doing and it’ll be fine!’ The world and the markets were like, ‘No. This is mincemeat.’”

If you like this show, you should also sample our other podcasts:

  • Recode Media with Peter Kafka features no-nonsense conversations with the smartest and most interesting people in the media world, with new episodes every Thursday. Use these links to subscribe on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.
  • Too Embarrassed to Ask, hosted by Kara Swisher and The Verge’s Lauren Goode, answers the tech questions sent in by our readers and listeners. You can hear new episodes every Friday on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.
  • And Recode Replay has all the audio from our live events, including the Code Conference, Code Media and the Code Commerce Series. Subscribe today on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.

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