Groupon and Descript: Andrew Mason

Andrew Mason was a 27-year-old with a degree in music when he co-founded one of the fastest growing companies of all time: Groupon. Its deep discounts on everything from sushi rolls to plastic surgery soon became a ubiquitous part of life in cities across the world. In 2011, just three years after launching, Groupon had the largest internet IPO since Google, with a valuation of $12.7 billion. But people began to complain that Andrew was not up to the role of CEO: he was quirky and unpredictable, and unable to navigate the company’s rocket-ship growth and the surge of copycats that threatened it. Soon, Groupon’s revenue slumped, and Andrew was fired from the company he’d started. But like many of the best entrepreneurs, he learned from his failure. Today, Andrew runs a new startup, an audio and video editing platform called Descript. In fact, we use Descript to make this show!  This episode was produced by Chris Maccini with music by Ramtin Arablouei. Edited by Neva Grant, with research from Kathrine Sypher. Our audio engineers were Maggie Luthar and Robert Rodriguez. You can follow HIBT on X & Instagram, and email us at hibt@id.wondery.com. Sign up for Guy’s free newsletter at guyraz.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Guy Raz interviews the world’s best-known entrepreneurs to learn how they built their iconic brands. In each episode, founders reveal deep, intimate moments of doubt and failure, and share insights on their eventual success. How I Built This is a master-class on innovation, creativity, leadership and how to navigate challenges of all kinds.New episodes release on Mondays and Thursdays. Listen to How I Built This on the Wondery App or wherever you listen to your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/how-i-built-this now. Get your How I Built This merch at WonderyShop.com/HowIBuiltThis.