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.
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Underlord: Descript’s AI Video Editor, with CEO Andrew Mason
Nathan interviews Andrew Mason, CEO of Descript, about their AI-powered video editing platform. Learn how Descript is transforming content creation with features like AI transcription, custom voice overdubbing, and eye contact models. Discover the future of video editing and how AI is making it accessible to everyone in this insightful episode of The Cognitive Revolution.
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CHAPTERS:
(00:00:00) About the Show
(00:00:22) Sponsor: WorkOS
(00:05:18) Creating Descript
(00:06:53) Favorite Features
(00:10:41) Descript Workflow
(00:14:10) Product Strategy (Part 1)
(00:16:45) Sponsors: Oracle | Brave
(00:31:12) User Fine-Tuning (Part 1)
(00:32:24) Sponsors: Omneky | Squad
(00:34:10) User Fine-Tuning (Part 2)
(00:34:54) Content Creators
(00:42:20) Small Businesses and AI
(00:43:42) Hiring AI Engineers
(00:46:25) Outro
Pod Squad: Descript Uses AI to Make Managing Podcasts Quicker, Easier - Ep. 105
You can’t have an AI podcast and not interview someone using AI to make podcasts better. That’s why we reached out to serial entrepreneur Andrew Mason to talk to him about what he’s doing now. His company, Descript Podcast Studio, uses AI, natural language processing and automatic speech synthesis to make podcast editing easier and more collaborative.
The future of podcasting with Andrew Mason
On this episode Abadesi talks to Andrew Mason, founder and CEO of Descript. He was formerly founder of Detour, which Descript emerged within before it was spun out into its own company when Bose bought the technology behind Detour. Andrew was also founder of Groupon.
In this episode they talk about...
Descript’s origin as part of Detour, and how to know when it’s the right time to pivot from your original idea
“We would have been over-investing in Descript if all we were using it for was for Detour, but we knew there was a potential business there and were treating it like a kind of a backup plan when you’re pre-product-market fit, like we were. You’re staying open to different paths.”
Descript actually emerged as a part of Detour, the company Andrew founded to create local audio tours. The team built themselves a better workflow for editing audio and realized that the internal product they had created could be much larger than Detour itself. They also recognized that a confluence of factors in tech were going to allow them to create the next generation of audio editing tools. Andrew explains how he went through the process of figuring out when to “cut bait” on Detour. He previously had pivoted The Point into Groupon, so he has some insightful things to say about when and how to pivot.
“We tried every last possible approach that we could think of and eventually it was like, it’s not supposed to be this hard. Having been through this before, it felt like we were doing the most elaborate things to market the product and reach customers, and at some point it just clicked that it’s not supposed to be this hard and we should move on.”
Andrew’s advice on managing people and scaling a company
“In a lot of companies the way that people get into management is they'll be individual contributors who have great ideas and nobody wants to listen to their ideas because it's the people in management that get to have those conversations. So people say 'okay, I guess I'll become a manager' and then they become a manager for completely the wrong reasons — not because they care about people or unlocking the best possible incarnation of their teams, but because they care about having their ideas listened to.”
He gives a rundown of the history of the company and where they are at now, after having raised a large Series A round and made the acquisition of Lyrebird. He talks about what the next stage of growth will hold for them, and how he is managing the scaling process by putting into place processes and protocols that will provide structure for the company as it grows. He also talks about the importance of delegating the work that the founder has been doing in a growing company.
Personal development as a leader and helping your team grow
Andrew explains what a typical day looks like for the team at Descript. He explains how they manage internal tools and how he tries to create an environment where feedback can flow freely among the team members. He talks about some of the best ways to grow as a leader, including some of the events that he attends and why he reads a lot. He also says that they have created an internal podcast for the team, a cool idea which you might expect from the company given what Descript is typically used for!
Andrew also tells us about one of his favorite products that he uses to build tools for the team.
We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. 😸
Companies and Products Mentioned In This Episode
Retool — Customized internal tools in minutes.
Recode Decode: Andrew Mason, CEO, Descript
Andrew Mason, the founder and former CEO of Groupon, talks with Recode’s Kara Swisher and The Verge’s Casey Newton about his latest startup, Descript. The company bills itself as a “word processor for audio,” making podcasts and other spoken word recordings easy to edit for non-technical content creators. Mason also talks about the “surreal” rise and fall of his career at Groupon, why he regrets publicly announcing that he was fired as CEO and why he once brought a horse to Groupon’s office as a gift for Michael Bloomberg.
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