Andrew Mason

Mason was born on October 22, 1980, in Pittsburgh, Pennsylvania, and grew up in the Pittsburgh suburb of Mount Lebanon; both of his parents were entrepreneurs. At 15 he started Bagel Express, a weekend bagel home-delivery service.⁠[1][2]

He studied music at Northwestern University, graduating in 2003.⁠[2][1]

In 2006 Mason won a scholarship to the University of Chicago’s Harris School of Public Policy and dropped out three months later to work on The Point, a website for organizing collective action and fund-raising around a cause, which collected pledges only once a target was reached; he came up with the idea after struggling to get out of a cell phone contract, and Eric Lefkofsky provided $1 million in startup funding.⁠[1][2]

In 2007 Mason began exploring collective buying as a way to make The Point profitable; in 2008 he co-founded Groupon, which evolved out of The Point, with Lefkofsky and became its CEO, and Groupon offered its first deal in Chicago in November 2008. Groupon took up to 50 percent of a deal’s retail value.⁠[1][2][3]

In November 2010 GoogleGoogleGoogle is an American technology company founded by Larry Page and Sergey Brin and incorporated in 1998. It became an Alphabet subsidiary in 2015. Its businesses include internet search, advertising, software platforms, cloud computing, and artificial intelligence.Open the full entry expressed interest in buying Groupon for about $6 billion; Mason and his executives turned it down.⁠[1]

In June 2011 Groupon filed to go public; it then had 83 million subscribers, nearly 57,000 local merchants and operations in 43 countries. In his letter to investors Mason wrote that the path to success would have “twists and turns, moments of brilliance and other moments of sheer stupidity.”⁠[2][1]

In November 2011 Groupon completed its IPO, raising $700 million at a $12.7 billion valuation. By 2012 it had more than 12,000 employees and operated in more than 150 U.S. cities and over 40 countries; by August 2012 its stock had fallen 75 percent.⁠[1]

On February 28, 2013, after Groupon released weak fourth-quarter results, its board replaced Mason; Executive Chairman Eric Lefkofsky and Vice Chairman Ted Leonsis took over as interim co-CEOs in a new Office of the Chief Executive while the company searched for a permanent successor. Their internal memo said, “Andrew has been asked to step down.” Groupon’s stock fell about 24 percent that day, after falling about 75 percent over the previous year.⁠[3][4]

In his farewell letter to employees, Mason referred to his four and a half years as CEO and wrote, “I was fired today.” He cited the company’s controversial metrics, a material weakness, missed expectations and a stock price far below its listing price.⁠[3][4]

On February 3, 2015, Mason’s audio tour app Detour went live on the App Store. Detour offered automated, location-aware walking tours, narrative audio experiences that led listeners through lesser-known shops and alleys of San Francisco, using GPS and iBeacons so users could walk at their own pace, with synced sessions for groups; at launch it offered six Bay Area tours at $5 each or $20 for an annual subscription, with Austin planned next.⁠[5]

Discussing pricing, Mason said: “We don't want to give people a reason to not try Detour.” Detour was self-funded by Mason, apart from a small early investment from his friend Mihir Shah.⁠[5][6]

On August 12, 2015, Andreessen HorowitzAndreessen HorowitzAndreessen Horowitz (a16z) is a venture capital firm founded in 2009 by Marc Andreessen and Ben Horowitz. It invests from the seed stage through the growth stage and provides operational support to its portfolio companies.Open the full entry released the a16z Podcast episode “a16z Podcast: Is It Possible to Achieve Equitable Equity for Startup Employees?”, in which former Groupon CEO Mason discussed with Ben HorowitzBen HorowitzBen Horowitz is an American entrepreneur, venture capitalist and business author who co-founded Andreessen Horowitz (a16z) with Marc Andreessen in 2009. He previously led Loudcloud’s transition into Opsware and its 2007 sale to Hewlett-Packard. His writing and investing address startup management, organizational culture and the relationship between technology and cultural industries.Open the full entry, cofounder and general partner of Andreessen Horowitz, his idea of “progressive equity,” intended to help more startup employees reach financial independence after an IPO, acquisition or other liquidity event.⁠[7]

The episode examined whether the approach could work and whether it should, and noted recent efforts to improve equity compensation such as removing tax liabilities that tie employees to their equity. It was uploaded to the a16z YouTubeYouTubeYouTube is Google’s video-sharing and creator platform, founded in 2005 by Steve Chen, Chad Hurley, and Jawed Karim and acquired by Google in 2006. Built around video uploading, viewing, and creator earnings, the platform has developed Shorts, YouTube Music, Premium, YouTube TV, and products for children, and is headquartered in San Bruno, California, United States.Open the full entry channel on January 1, 2019, as “a16z Podcast | Is It Possible to Achieve Equitable Equity for Startup Employees?”⁠[7][8]

The Detour team built transcript-based audio editing tools and a way to add music and sound effects to narration through the transcript; these technologies were spun off into Descript, which aims to make editing sound files as simple as editing a Word document. Descript launched in December 2017 with $5 million from Andreessen Horowitz.⁠[6]

Mason left the CEO role at Detour to become CEO of Descript. Descript uses AI to transcribe an audio file in a few minutes and links each word to the audio, so that editing the text edits the audio, with export to professional tools such as Adobe Audition; the Andreessen Horowitz seed investment came from general partner Alex RampellAlex RampellAlex Rampell (Alastair Rampell) is an entrepreneur and investor, a general partner at Andreessen Horowitz and leader of its Apps practice. He co-founded TrialPay and Affirm and serves on the boards of Wise and Rocket Companies.Open the full entry.⁠[9]

In April 2018 Bose acquired Detour’s software and tour content, but not its team, on undisclosed terms; the Detour app remained available until May 31, 2018, and had about 120 tours at the time of the sale. Mason said he was focused on Descript, writing on Detour’s blog: “Thank you to the producers, engineers, designers, and storytellers that made Detour what it is over the last four years.”⁠[6]

Descript states that it has raised $100 million in total, with primary investors including the OpenAI Startup FundOpenAI Startup FundThe OpenAI Startup Fund is a venture fund set up by OpenAI in May 2021 with an initial $100 million from Microsoft and other partners to invest in early-stage AI companies. It had raised about $175 million by 2023, and control passed to Ian Hathaway in March 2024.Open the full entry, Andreessen Horowitz, Redpoint Ventures and Spark CapitalSpark CapitalSpark Capital is a U.S. venture capital firm founded in Boston in 2005, with offices in San Francisco, New York and Boston. Its early-stage and growth funds back technology businesses across fintech, enterprise software, AI and consumer products. Investments have included Twitter, Tumblr, Oculus, Plaid and Anthropic.Open the full entry, and describes its product as built on text-based editing, automated design and prompt-based editing.⁠[10]

Descript: Official website: https://www.descript.com/ (opens in a new window).⁠[10]