Andrew Mason

Andrew Mason
Mason in 2011
Andrew Mason
Born	Template:Birth year and age
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 businessman and entrepreneur best known as the founder and former chief executive officer of Groupon, the Chicago-based daily deals platform that grew from a modest group-buying concept into one of the fastest-growing companies in Internet history. Born in Pittsburgh, Pennsylvania, and educated in music at Northwestern University, Mason built Groupon from its origins as a side project of his earlier venture, The Point, into a global commerce enterprise that famously turned down a reported $6 billion acquisition offer from Google in 2010. His tenure as CEO ended in February 2013, when the company's board removed him amid declining stock prices and questions about the firm's long-term business model. In the years following his departure from Groupon, Mason launched new ventures including Detour, a location-based audio walking tour startup later acquired by Bose Corporation, and Descript, an audio and video editing platform powered by machine learning. His career trajectory — from music student to billionaire-on-paper CEO to fired executive to startup founder once again — has made him one of the more distinctive figures in the American technology industry of the early 21st century.

Early Life

Andrew D. Mason was born in 1981 in Pittsburgh, Pennsylvania. Details about his parents and family background during his childhood years in Pittsburgh remain limited in published sources. Mason grew up in the Pittsburgh area before relocating to the Chicago metropolitan region to attend college. According to profiles published during his rise at Groupon, Mason displayed an early aptitude for technology and creative pursuits, interests that would eventually converge in his entrepreneurial career.

Mason's upbringing in Pittsburgh, a city with deep roots in industry and a growing technology sector, provided context for his later work in building Internet-based businesses. He moved to Evanston, Illinois, to attend Northwestern University, a decision that would place him in the broader Chicago ecosystem where he would eventually build Groupon into a major enterprise.

Education

Mason enrolled at Northwestern University's Bienen School of Music, where he studied music and earned a Bachelor of Arts degree in 2003. His academic background in music rather than business or computer science distinguished him from many of his peers in the technology startup world. Despite his formal training in the arts, Mason had developed skills in web development and technology that he would deploy in his post-college career.

After completing his undergraduate degree, Mason remained in the Chicago area. He later began graduate studies in public policy at the University of Chicago, though he did not complete the program, leaving to pursue entrepreneurial ventures full-time. This decision to abandon graduate school in favor of a startup would prove to be a pivotal turning point in his career.

Career

The Point and Early Ventures

Before founding Groupon, Mason worked in the Chicago technology scene. He conceived of a web platform called The Point, a social activism site built around the concept of collective action — users could rally around causes and pledge to act only once a tipping point of participation was reached. The Point was backed by Eric Lefkofsky, a Chicago-based entrepreneur and investor who would become a central figure in the Groupon story. The tipping-point mechanism of The Point — where an action would only be triggered once a sufficient number of people committed — became the conceptual foundation upon which Groupon was built.

The Point itself did not achieve significant commercial traction, but one particular use case stood out: users were leveraging the platform to organize group purchases, aggregating demand to negotiate bulk discounts from local businesses. This observation led Mason and his backers to pivot toward a dedicated group-buying platform, which launched in November 2008 as Groupon — a portmanteau of "group" and "coupon."

Founding and Growth of Groupon

Groupon launched in Chicago in November 2008 with a simple premise: the platform would offer a single daily deal from a local business — a restaurant, spa, retailer, or service provider — at a significant discount, typically 50 percent or more off the regular price. The deal would activate only if a minimum number of buyers committed, applying the tipping-point model from The Point. The business model proved extraordinarily popular. Groupon expanded rapidly from its Chicago base to other cities across the United States and then internationally.

Mason served as CEO during this period of explosive growth. Under his leadership, Groupon grew at a pace that drew comparisons to some of the fastest-growing Internet companies in history. The company's model was attractive to consumers, who received steep discounts, and to small businesses, which gained exposure to new customers, though the economics for merchants were the subject of ongoing debate.

By 2010, Groupon had expanded to hundreds of markets worldwide and employed thousands of people. The company's workforce included a large editorial team responsible for writing the humorous, irreverent descriptions that accompanied each deal — a feature that became part of the Groupon brand identity and reflected Mason's own sensibility.

Google Acquisition Offer

In late 2010, Groupon became the subject of one of the most talked-about acquisition offers in technology industry history. Google reportedly offered approximately $6 billion to acquire the company, which would have been one of the largest acquisitions in the Internet sector at the time. Mason and Groupon's board ultimately rejected the offer, a decision confirmed in early December 2010.

The decision to turn down Google's bid was one of the most scrutinized business decisions of the era. Supporters argued that Groupon's growth trajectory justified holding out for a higher valuation, while skeptics questioned whether the company's business model was sustainable enough to warrant such confidence. The rejection set the stage for Groupon's pursuit of an initial public offering.

Initial Public Offering

Groupon filed for its initial public offering in June 2011 and went public on the NASDAQ stock exchange in November 2011. The IPO valued the company at approximately $13 billion, making it one of the largest Internet IPOs since Google's own offering in 2004. Mason, as the founder and CEO of a publicly traded company, became one of the most prominent young executives in American business.

However, the IPO process was not without controversy. Groupon's financial disclosures drew scrutiny from regulators and analysts, particularly regarding the company's use of non-standard accounting metrics. The U.S. Securities and Exchange Commission raised questions about certain financial measures the company had presented in its prospectus.

Despite the successful IPO, Mason's salary as CEO was notable for its modesty relative to the company's valuation. Reports indicated that his annual salary was $756.72 — a figure that attracted attention for its unusually low amount, though he held substantial equity in the company.

Decline and Termination as CEO

Following the IPO, Groupon's stock price experienced a significant decline as investors grew concerned about the company's profitability, its competitive position, and the sustainability of the daily deals model. The stock fell substantially from its IPO price over the course of 2012, and the company faced increasing competition from rivals including LivingSocial and Amazon's entry into the local deals space.

On February 28, 2013, Groupon's board of directors removed Mason as CEO. Mason's response to his termination drew widespread attention for its unusual candor. Rather than issuing a standard corporate statement, he sent a memo to Groupon employees acknowledging his firing directly. In the memo, he took responsibility for the company's underperformance and wished his successor well.

The departure was widely covered in the business and technology press. Commentators noted that Mason's firing represented the end of a rapid and dramatic arc — from founding a startup to leading a company valued in the billions to being removed by the board in the span of roughly four years.

Post-Groupon: Music Album

In the months following his departure from Groupon, Mason took an unexpected creative detour. In July 2013, he released a motivational business music album titled Hardly Workin', which featured seven tracks with titles related to business and corporate life. The album, which Mason described in earnest terms, drew extensive media coverage for its novelty — a recently fired CEO of a multi-billion-dollar public company releasing a music album was, by any measure, an unusual career move.

Mason's background in music — he had earned his bachelor's degree in the subject from Northwestern — lent some context to the project, though most observers treated it as an eccentric post-firing diversion rather than a serious career pivot.

Detour

After his musical interlude, Mason returned to the technology sector. He founded Detour, a startup that produced location-based audio walking tours. The app used GPS technology to deliver narrated walking tours that adapted to a user's pace and location, offering immersive audio experiences in cities including San Francisco, New York City, Austin, and Chicago.

Detour represented a different approach from the mass-market scale of Groupon. The product was more niche, focused on the intersection of audio storytelling and geographic exploration. In April 2018, Bose Corporation, the audio equipment manufacturer, acquired Detour. The acquisition reflected Bose's interest in location-aware audio experiences and augmented reality audio technologies.

Descript

Mason's next venture, Descript, became his most significant post-Groupon project. Founded in 2017, Descript is an audio and video editing software platform that uses machine learning and artificial intelligence to enable users to edit media by manipulating text transcripts rather than traditional waveform or timeline editing.

The core innovation of Descript was its approach to editing: the software transcribes audio and video content into text, and users can edit the media by editing the transcript — deleting a word from the transcript deletes the corresponding audio or video, for instance. This approach represented a significant departure from conventional editing workflows and made audio and video editing more accessible to users without specialized technical skills.

Mason serves as the founder and CEO of Descript, which is based in San Francisco. The company has attracted attention from the technology industry for its application of AI to creative tools, positioning it within the broader trend of machine learning-powered productivity software.

Personal Life

Mason married Jenny Gillespie, a musician and singer-songwriter. Their relationship became a subject of public interest given Mason's profile as a technology executive. Gillespie has performed and recorded music independently of her husband's business career.

Mason has maintained a relatively low public profile compared to his Groupon-era visibility. His personal interests, including music — both through his formal education and his post-Groupon album — have been documented in various media profiles. He relocated from Chicago to the San Francisco Bay Area in connection with his post-Groupon ventures.

Recognition

Mason's career has generated extensive media coverage and analysis, primarily centered on his role at Groupon. During the company's peak growth period in 2010 and 2011, he was the subject of major profiles in publications including Chicago Magazine, Time Out Chicago, The Seattle Times, and numerous technology and business outlets.

The decision to reject Google's reported $6 billion acquisition offer in 2010 was one of the most discussed business decisions of that year, generating commentary across financial and technology media. The subsequent IPO and Mason's eventual firing further cemented his status as a figure of significant public interest in the technology business world.

Mason's candid farewell memo following his termination from Groupon attracted attention for its tone, which contrasted with the typical corporate communications associated with executive departures. The New York Times described the end of his Groupon tenure as a "long, strange trip," reflecting the unusual trajectory of his leadership of the company.

His post-Groupon ventures have also been covered in major technology publications, with particular interest in how a founder who experienced both rapid ascent and a public fall would approach subsequent entrepreneurial endeavors.

Legacy

Andrew Mason's career is most closely associated with the rise and fall of the daily deals industry. Groupon, under his leadership, popularized the concept of group buying and daily deals in a way that reshaped local commerce and digital marketing for small businesses in the early 2010s. At its peak, the company operated in hundreds of markets across dozens of countries and employed thousands of people, establishing a new category of e-commerce.

The rejection of Google's $6 billion offer and the subsequent decline in Groupon's stock price after its IPO became a case study in technology company valuations, startup governance, and the challenges of sustaining high-growth business models. Business schools and industry analysts have examined the Groupon story as an illustration of both the opportunities and risks inherent in rapid scaling of Internet-based businesses.

Mason's transition from Groupon to subsequent ventures — first the audio walking tour company Detour, then the AI-powered editing platform Descript — demonstrated a pattern of applying technology to media and consumer experiences. His career after Groupon illustrated the capacity of Silicon Valley's startup ecosystem to provide second acts for founders, even after high-profile setbacks.

His management of the Groupon page, from the founding through rapid growth, the rejection of Google's offer, the IPO, and eventual termination, remains one of the more dramatic narratives in the history of American Internet companies. The candor of his public response to being fired — unusual in a corporate culture that typically favors carefully managed messaging — contributed to his reputation as an unconventional executive.