Andrew Mason

Andrew Mason
Mason in 2011
Andrew Mason
Born	1981
Birthplace	Pittsburgh, Pennsylvania, U.S.
Nationality	American
Occupation	Entrepreneur, software executive
Known for	Founder and former CEO of Groupon; founder and CEO of Descript
Education	Bachelor of Arts in Music (2003)
Spouse(s)	Jenny Gillespie

Andrew D. Mason (born 1981) is an American entrepreneur and technology executive who founded Groupon, the Chicago-based e-commerce platform that became one of the fastest-growing companies in Internet history. Born in Pittsburgh, Pennsylvania, Mason built Groupon from a side project into a global daily-deals giant that famously turned down a reported $6 billion acquisition offer from Google in 2010 before going public in 2011. Mason served as Groupon's CEO until his ouster in February 2013, after which he pursued ventures in music, audio tour technology, and audio/video editing software. He is the founder and CEO of Descript, a software company that develops audio and video editing tools powered by machine learning.

Early Life

Andrew D. Mason was born in 1981 in Pittsburgh, Pennsylvania. Details about his parents and upbringing in Pittsburgh remain largely private, though Mason has been described in profiles as having shown an early interest in both technology and music. He grew up in the Pittsburgh area before relocating to the Chicago metropolitan region to attend college at Northwestern University.

Mason's formative years in Pittsburgh coincided with the rise of the early Internet era in the 1990s, which would later inform his interest in web-based businesses. His dual interests in creative pursuits and technology became a defining theme throughout his career, shaping the unconventional leadership style he would later bring to Groupon and his subsequent ventures.

Education

Mason attended the Bienen School of Music at Northwestern University in Evanston, Illinois, where he earned a Bachelor of Arts degree in Music in 2003. His music education background distinguished him from the typical profile of a technology startup founder and later informed several of his post-Groupon creative endeavors, including a motivational music album released in 2013.

After completing his undergraduate studies, Mason remained in the Chicago area. He later enrolled in a public policy program at the University of Chicago but did not complete a graduate degree, choosing instead to focus on his emerging entrepreneurial projects.

Career

The Point and the Genesis of Groupon

Before founding Groupon, Mason created a web platform called The Point, a social activism and collective-action website that allowed users to organize campaigns around shared goals. The Point operated on a "tipping point" model in which campaigns would only activate once a critical mass of participants had committed. The concept of collective buying power that underpinned The Point would become the foundational idea behind Groupon.

The pivot from The Point to Groupon emerged when Mason and his team noticed that collective buying—groups of people pooling together to unlock a discount from a local merchant—was one of the most popular uses of the platform. This observation led to the creation of Groupon, a portmanteau of "group" and "coupon," in November 2008. The site offered one deal per day in a single city, Chicago, with the deal activating only if a minimum number of buyers committed—a direct application of The Point's tipping-point mechanism.

Groupon's Rapid Growth

Groupon experienced extraordinarily rapid expansion following its founding. The company's model—offering deep discounts on restaurants, spas, entertainment, and other local services in exchange for guaranteed customer volume to merchants—resonated with consumers during the economic downturn of the late 2000s. Within two years, Groupon expanded from a single-city operation to a presence in hundreds of markets across North America and internationally.

The company's growth attracted significant attention from both investors and potential acquirers. In late 2010, Google reportedly offered approximately $6 billion to acquire Groupon, which would have been one of the largest acquisitions in Internet history at the time. Mason and the Groupon board rejected the offer, a decision that generated substantial debate in the technology and business press. Some observers viewed the rejection as a bold bet on the company's continued growth trajectory, while others questioned whether the decision was sound given the company's unproven long-term business model.

Mason served as the public face of Groupon during this period, cultivating an image that was notably more informal and irreverent than the typical Silicon Valley CEO. Profiles described his management style as unconventional, blending humor and an anti-corporate ethos into the company's culture and marketing.

Groupon IPO and Public Company Challenges

Groupon filed for an initial public offering in June 2011 and began trading on the NASDAQ stock exchange on November 4, 2011. The IPO was one of the most closely watched technology offerings since Google's own public debut in 2004. The company was valued at approximately $12.7 billion at its IPO, making it one of the largest Internet IPOs at the time.

However, Groupon's tenure as a public company proved turbulent. The company faced criticism over its accounting practices, particularly its use of a non-standard metric called "adjusted consolidated segment operating income" (ACSOI), which excluded certain costs that traditional accounting methods would include. The company was required to restate its fourth-quarter 2011 results due to a "material weakness" in its internal controls, further eroding investor confidence.

Mason's salary during his time as CEO drew media attention for being unusually modest by Silicon Valley standards. Reports indicated his annual salary was $756.72, a figure widely noted for its apparent quirkiness. While Mason held significant equity in the company, the nominal salary figure underscored his unconventional approach to corporate leadership.

Groupon's stock price declined significantly from its IPO highs as the company struggled to demonstrate sustainable profitability and fend off competition from rivals including LivingSocial and Amazon's local deals service. The daily deals market, which had boomed in 2010 and 2011, began showing signs of saturation, and merchants increasingly questioned whether the deep discounts offered through Groupon generated loyal repeat customers or merely attracted one-time bargain seekers.

Departure from Groupon

On February 28, 2013, Groupon's board of directors removed Mason from his position as CEO. The dismissal came after a prolonged period of declining stock prices and missed revenue expectations. Mason's departure was notable for the candid and self-deprecating letter he sent to Groupon employees, which became widely circulated in the media. In the letter, he acknowledged that he had been "fired" rather than employing the corporate euphemism of "stepping down," and took responsibility for the company's disappointing performance as a public company.

The ouster left Groupon searching for a new chief executive to chart a sustainable path to profitability. Executive Chairman Eric Lefkofsky, who had been an early backer and co-founder of the company, stepped in as interim leader. Mason's departure marked the end of an era for one of the most talked-about Internet companies of the early 2010s.

Motivational Music Album

In a move that surprised observers in both the technology and entertainment industries, Mason released a motivational music album titled Hardly Workin' in July 2013, just months after his departure from Groupon. The album featured seven tracks of motivational rock songs with titles focused on business and self-improvement themes. Mason described the project as a genuine creative effort rather than a joke, though media coverage frequently noted its eccentricity.

The album drew attention in part because of Mason's educational background in music from Northwestern University's Bienen School of Music, lending the project a degree of credibility that a typical tech executive's musical foray might not possess. Reviews and media reactions were mixed, with many outlets treating the release as a curiosity rather than a serious musical endeavor, though some commentators praised Mason's willingness to pursue an unconventional post-CEO path.

Detour

Following his departure from Groupon and the release of his music album, Mason founded Detour, a startup focused on location-based audio walking tours. Detour offered immersive, GPS-triggered audio experiences that guided users through cities with narrated stories about neighborhoods, landmarks, and local culture. The app represented a departure from the e-commerce and daily deals space, drawing instead on Mason's interests in storytelling, technology, and urban exploration.

In April 2018, Bose Corporation acquired Detour. The acquisition was seen as part of Bose's broader interest in augmented audio experiences and wearable technology. The sale of Detour to Bose provided a successful exit for the venture and allowed Mason to turn his attention to his next project.

Descript

In 2017, Mason founded Descript, a software company developing audio and video editing tools powered by machine learning and artificial intelligence. Descript's flagship product allows users to edit audio and video by editing a text transcript—a novel approach that makes media editing more accessible to users without professional editing experience. The software uses speech recognition and AI to generate transcripts of audio and video files, enabling users to cut, rearrange, and modify content by manipulating text rather than navigating traditional timeline-based editing interfaces.

Mason has served as CEO of Descript since its founding. The company has attracted attention in the podcasting, journalism, and content creation communities for its innovative approach to editing workflows. Descript represents Mason's continued interest in building technology products that simplify complex processes, a thread that connects back to his work at Groupon in making local commerce more accessible to consumers.

Personal Life

Mason is married to Jenny Gillespie, a musician and singer-songwriter based in Chicago. Gillespie has maintained her own independent musical career alongside Mason's entrepreneurial activities. The couple has largely kept the details of their personal life private.

Mason has been based in the Chicago area for much of his adult life, having settled there after attending Northwestern University. His personal interests, as reflected in his career choices and public statements, span music, technology, urban exploration, and creative media production.

Recognition

Mason's founding of Groupon brought him significant public attention during the company's peak growth period from 2009 to 2012. He was featured in numerous national and international media profiles as the face of the daily deals phenomenon, with outlets including Chicago Magazine, Time Out Chicago, The New York Times, Bloomberg News, and Business Insider covering his career and leadership style.

Groupon's rejection of Google's reported $6 billion acquisition offer in 2010 and its subsequent IPO placed Mason among the most discussed technology entrepreneurs of the early 2010s. His candid firing letter in 2013, in which he openly acknowledged his dismissal and took responsibility for Groupon's underperformance, was widely circulated and praised for its honesty in an industry where executive departures are typically announced with carefully worded press releases about "pursuing other opportunities."

Mason's post-Groupon ventures, including Detour's acquisition by Bose and the founding of Descript, have demonstrated his continued relevance in the technology industry beyond the daily deals era.

Legacy

Andrew Mason's career is most closely associated with the rise and subsequent challenges of the daily deals industry. Groupon, under his leadership, popularized the concept of group buying and daily discount offers, creating an entirely new category of e-commerce that at its peak attracted hundreds of imitators worldwide. The company's trajectory—from a small Chicago startup to a multi-billion-dollar public company facing questions about its long-term viability—became a frequently cited case study in the technology industry about the risks of rapid scaling, the challenges of transitioning from startup to public company, and the sustainability of business models built on deep discounting.

Mason's rejection of Google's acquisition offer remains one of the most debated decisions in recent technology business history. While the decision was criticized in hindsight as Groupon's stock price fell below its IPO price, it also reflected the confidence—and the risk appetite—that characterized the era's most ambitious technology founders.

His post-Groupon career has demonstrated a pattern of pursuing ventures at the intersection of technology and creative media. From the audio walking tours of Detour to the AI-powered editing tools of Descript, Mason has consistently sought to build products that use technology to make creative and experiential activities more accessible. His willingness to pivot between industries and his comfort with public failure—exemplified by his candid firing letter and his unconventional motivational music album—have made him a distinctive figure among American technology entrepreneurs.