Andrew Mason: Bringing Together Groupon

February 20, 2024
minutes to read
Ben Winford
Table of Contents

Few stories in the history of online commerce weave as boldly as that of Andrew Mason, the visionary founder of Groupon. From the nascent days of Bagel Express to the meteoric rise and unexpected twists at Groupon, join us on a compelling journey through the life and ventures of this American businessman. Uncover the untold chapters, from his musical detour to the creation of Descript, as we navigate the triumphs, challenges, and multifaceted layers of Andrew Mason's remarkable career.

Early Childhood

Andrew D. Mason, born in 1981 into a Jewish family in Mount Lebanon, Pennsylvania, embarked on a journey that would significantly impact the tech landscape. His formative years unfolded against the backdrop of Mount Lebanon, a suburb of Pittsburgh. A standout entrepreneur even in his teens, Mason founded "Bagel Express," a Saturday morning delivery service, at the tender age of 15. Mason's academic pursuits led him to Northwestern University, where he graduated in 2003 with a degree in music. The convergence of creative inclination and entrepreneurial spirit defined his early years.

Stepping into the World of Entrepreneurship

Post-graduation, Mason immersed himself in web design, working under the guidance of Chicago entrepreneur Eric Lefkofsky. However, the quest for knowledge prompted him to enrol in the University of Chicago's Harris School of Public Policy, fueled by a scholarship.

Despite his initial academic pursuit, Mason's passion for entrepreneurship proved stronger. After a brief stint, he departed from his master's degree program, choosing the path of practical experience over formal education. During this period, Mason interned at Electrical Audio, a prestigious Chicago recording studio under the tutelage of recording engineer Steve Albini, whose influence shaped Mason's work ethic.

The Evolution: From The Point to Groupon

Andrew Mason's foray into the tech landscape gained momentum when he joined InnerWorkings, a company founded by Eric Lefkofsky in 2006. Lefkofsky's investment of $1 million served as "seed money" for Mason's first internet entrepreneurial venture, "The Point."

Initially conceived as a social initiatives platform inspired by Malcolm Gladwell's "The Tipping Point," The Point underwent a transformative journey. Recognising the abstract nature of the platform, Mason streamlined the concept, giving rise to Groupon. The platform, offering localized deals to users, took flight in November 2008.

Groupon's exponential growth was undeniable. By late 2010, the platform's annual revenue reached an impressive $800 million. The success prompted Google to extend a substantial $6 billion acquisition bid in December 2010, which Groupon declined.

Rollercoaster Leadership and Public Offering

As Groupon continued its ascent, Andrew Mason's leadership style and unconventional antics became a subject of scrutiny. Despite facing challenges in 2012, including missing sales targets, Groupon went public in November, marking a significant milestone.

The year 2012 concluded with Mason being dubbed "Worst CEO of the Year" by Herb Greenberg of CNBC. The critique pointed to Mason's leadership style, which, though charismatic, seemed at odds with the challenges faced by Groupon. The company's stock price hovered significantly below its listing price.

The turning point arrived on 28 February 2013, when Mason was ousted as Groupon's CEO. The decision came from the company's failure to meet analysts' expectations for sales and profitability.

Mason exhibited a blend of humour and accountability in a candid letter to Groupon employees on the day of his dismissal. Acknowledging the company's tumultuous journey, he cited various challenges, from controversial metrics to missed expectations, ultimately taking responsibility for the company's performance.

Unconventional Ventures Post-Groupon

Andrew Mason's journey didn't conclude with his departure from Groupon. In an unexpected move, he released a motivational rock album titled "Hardly Workin'" in July 2013, available on iTunes and Spotify. Produced by Don Gehman, known for his work with R.E.M. and John Mellencamp, the album added a musical twist to Mason's diverse portfolio.

Describing the album as motivational business music, Mason noted that it aimed to guide individuals entering the workforce. Despite its unconventional nature, the album showcased Mason's willingness to explore unique avenues.

Additionally, Mason ventured into audio tours by creating the Detour app in February 2015. Offering unconventional audio tours of major cities, the app provided users a distinctive way to explore urban landscapes. In 2018, Detour found a new home as it was acquired by Bose, aligning with the company's plans for an Augmented Reality platform.

Lessons from the Groupon Odyssey

Reflecting on his tenure at Groupon, Mason emphasised the need for essential business wisdom. Managing a workforce of over 12,000, predominantly under 25, revealed the gaps in fundamental knowledge among new entrants.

The Groupon saga, marked by highs and lows, served as a testament to the unpredictable nature of the tech industry. Despite the controversies and challenges, Mason's resilience and creativity paved the way for a diverse post-Groupon portfolio, blending music, technology, and unconventional ventures.

Personal Life and Beyond

Beyond the tech world, Andrew Mason found harmony in his personal life by being married to pop/folk singer Jenny Gillespie. The intersection of his professional and personal spheres added another layer to the enigmatic persona of Andrew Mason.

Key Takeaways

In the complex story of Andrew Mason, the highs of Groupon's success and the lows of its challenges shaped a unique entrepreneurial tale. His journey, marked by creativity and resilience, serves as a lesson in the unpredictable landscape of the tech industry. Whether orchestrating deals on Groupon or composing motivational business music, Mason's ventures continue to reflect his penchant for the unconventional.

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