logo
episode-header-image
Sep 2024
1h 11m

Groupon and Descript: Andrew Mason

Guy Raz | Wondery
About this episode

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.

Up next
Today
Advice Line with Michael Dubin of Dollar Shave Club
Dollar Shave Club founder Michael Dubin joins Guy on the Advice Line to answer questions from three early-stage founders. Plus, Michael shares his latest career pivot into the screenwriting world.First, Benita from New Jersey asks how to create a “guerilla-style” marketing campai ... Show More
53m 54s
Oct 6
Pressbox and Tide Cleaners: Vijen Patel. The $1.99 Gamble That Built a National Brand
What if the best startup isn’t sexy at all? In 2013, Vijen Patel left private equity to pursue “the least-worst idea”: dry cleaning. No patents. No app wizardry. Just laundry lockers in high-rises, ruthless unit economics, and a $1.99-a-shirt price that was seared into America’s ... Show More
1h 6m
Oct 2
Advice Line with Tony Xu of Doordash
Tony Xu, founder of DoorDash, joins Guy on the Advice Line to answer questions from three early-stage entrepreneurs. Plus, Tony updates Guy on his latest ventures: expanding into grocery and retail delivery - and taking on international markets.First, we hear from Ron in Portland ... Show More
49m 13s
Recommended Episodes
Oct 2019
The Founder of Groupon’s New Thing!
Andrew Mason is the founder and former CEO of Groupon… who had a VERY public firing. Today, I’m talking to Andrew about what he learned getting fired from the company he helped create, how he dusted himself off to start a new business, and more.   Full show notes at https://okdor ... Show More
40m 9s
Jul 2016
Acquired Episode 15: ExactTarget (acquired by Salesforce) with Scott Dorsey
Ben and David return to make their first foray into enterprise software, covering Salesforce’s $2.5B acquisition of ExactTarget in 2013 with the help of special guest and ExactTarget cofounder & CEO, Scott Dorsey.   Technical note: due to an issue we didn’t catch during recording ... Show More
1h 16m
Oct 2024
Shut It Down or Double Down: Nathan Barry’s Road to $45M with Kit (ConvertKit)
Nathan Barry, the creator behind ConvertKit (now rebranded as Kit) came to visit my Inner Circle and gave a very special presentation. Nathan’s journey from a designer to building a software empire fascinated me. He originally tried to solve his frustrations with MailChimp and, i ... Show More
1h 2m
May 2025
Episode 769: Digital CEO Weekly Win: A Voice Actor Turns His Passion Into a 6-Figure Business & Grows His Revenue +177% Doing What He LOVES in a SMALL Niche - Paul Schmidt's BBD Success Story
Each day this week we’ve been highlighting Business By Design members who are doing incredible things in their businesses, and today is no exception! Jenni sits down with Paul Schmidt, a voice actor turned Digital CEO, as he pulls back the curtain and shares the big lessons and i ... Show More
58m 2s
Apr 2025
How An Online Marketer Raised $100M For His Business | Brian Moran
In this episode of The Wealthy Way podcast, I sit down with Brian Moran, the founder of SamCart, an eCommerce platform that helps business owners sell products, maximize profits, and build long-term customer relationships. We dive into Brian's journey, the birth of SamCart, ... Show More
1h 37m
Feb 2025
"I Fast-Forwarded My Life 10 Years”: How Geo-Arbitrage 3X’d My Wealth and Changed My Life
What if you could fast-forward your financial goals by ten years just by moving abroad? That’s exactly what entrepreneur Rob Hoffman did when he relocated to Colombia, where his $3M net worth stretches as if it’s $9M. Rob, a member of the Hampton community, shares how he built a ... Show More
32m 6s
Jan 2025
Mike Maples on 100-Baggers, David Swensen & the AI Revolution | #568
Today’s guest is Mike Maples Jr. a partner at Floodgate, a pre-seed and seed-stage venture capital firm that’s invested in companies like Twitter, Lyft, Twitch, Okta. He’s also the author of Pattern Breakers: Why Some Start-Ups Change the Future. In today’s episode, Mike shares h ... Show More
1h 11m
Mar 2025
How Tommy Mello Became a Billionaire Painting Garage Doors (And How He Shares the Wealth)
What does it take to turn a blue-collar business into a billion-dollar empire?For Tommy Mello, the answer is simple: relentless competition, strategic investing, and an unwavering commitment to winning. From painting garage doors to building A1 Garage Doors into a massive industr ... Show More
30m 47s
Mar 2025
The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic)
Matt Mullenweg is the co-founder of WordPress, the open source platform powering a staggering 43% of the internet. He also serves as CEO of Automattic—the parent company of brands like WordPress.com, WooCommerce, and Tumblr—which is worth over $7 billion, with over 1,700 employee ... Show More
1h 34m