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Groupon's Biggest Deal Ever

Groupon's Biggest Deal Ever

The Inside Story of How One Insane Gamble, Tons of Unbelievable Hype, and Millions of Wild Deals Made Billions for One Ballsy Joker

Frank Sennett

St. Martin's Press



The inside story of the meteoric rise of Groupon from startup to $30 billion online giant and the audacious genius behind it, founder Andrew Mason

In late 2010, Groupon made an incredible gamble. Rather than take Google's $6 billion buyout offer, founder Andrew Mason turned the search giant down and decided to go it alone. The experts thought he was insane. Groupon was little more than two years old and staffed from top to bottom with twenty-somethings. The wild ride couldn't last, but Mason thought otherwise, and with knowledge of a possible IPO he liked his odds.

A discount service that offers a deal a day at local merchants in countless cities in more than forty-three countries, Groupon is the fastest-growing company in Internet history and is as committed to innovating a new model for commerce as it is to creating an office culture and editorial voice based on radical transparency and absurd humor.

Groupon's Biggest Deal Ever is the exclusive and unparalleled account of the incredible rise of discount giant Groupon and the compelling story of its offbeat founder Andrew Mason as he created a juggernaut of online commerce and ignited a consumer revolution.


Praise for Groupon's Biggest Deal Ever

“Perfect for would-be entrepreneurs with a dollar and a dream.... Mr. Sennett had an enviable level of access during his reporting, and it pays off in a highly readable series of vignettes that demonstrate just how much personality plays in high-stakes Silicon Valley deal-making.... For students of start-ups, there is much to enjoy in this breezy retelling of three tumultuous years with hundreds of millions of dollars on the line.” —The Wall Street Journal

“Fresh, fun, and exciting! A great inside business story wonderfully told.” —Tony Hsieh, New York Times bestselling author of Delivering Happiness and CEO of, Inc.

“The 'insane gamble' referred to in the subtitle is the one in which Andrew Mason, the founder of the Internet coupon site Groupon, turned down a $6 billion buyout offer from Google.... Told with an appealingly jaunty prose style (imagine Ben Mezrich but with even more enthusiasm), the story portrays Mason as a plucky entrepreneur, a laidback and politically incorrect school prankster who, on the other hand, is a sharp-as-a-tack computer programmer and a guy who's savvy enough to know a good idea when he has it.... Is there a movie here, too, following in the wake of The Social Network? Well, there are no Winklevoss twins in the story, but don't bet against it.” —Booklist (Starred Review, Top 10 Business Book of 2012)

“By the end of the first chapter, Sennett's nuggets of detail swell into full-blown revelations. The Time Out Chicago editor in chief quickly plunges readers into Groupon's boardroom, providing one of the most detailed accounts of how close the founders came in late 2010 to accepting a $5.75 billion buyout offer from Google and why they ultimately rejected it.... The cover of Sennett's book promises "the inside story" of the Chicago-based daily deal company that went from tech startup to multibillion-dollar initial public offering in less than four years, and that's what it delivers. Even the closest of Groupon observers will learn a lot. And they'll also hear from company insiders who rarely grant interviews.... Through numerous anecdotes and observations, Sennett also captures all 360 degrees of Mason's personality, from his stubbornness and immaturity to his talent, dedication and loyalty.... Sennett has provided us with a well-written and revealing first draft of the company's start.” —Chicago Tribune

“[Groupon's Biggest Deal Ever] is the first comprehensive examination of Chicago's overnight Internet star; it takes readers from the company's start, through its almost-sale to Google Inc. in late 2010 to its IPO last fall.” —Crain’s Chicago Business

“A fast-and-furious account of how Groupon and its young founder bucked acquisition trends by rejecting a $6 billion buyout offer from web titan Google.... A justifiably dramatic look at the machinations of a resoundingly successful startup and its 'Andy Kaufman of CEOs.” —Kirkus Reviews

“Groupon CEO Andrew Mason takes center stage in this story about the company's founding, development, and explosive assent.... It's refreshing and enjoyable to read Sennett's likable portrait of Mason ("the inexperienced CEO hiding a brilliant analytical mind behind a goofball demeanor") and Lefkofsky (nicknamed "Punchable" by Mason for his hard-edged, "alpha dog" attitude). Sennett succeeds in presenting a balanced view of the company, complete with bad press and "damaging controversy.” —Publishers Weekly

“From the fast-paced opening pages, where we learn why Groupon rejected Google's $6 billion offer, Frank Sennett takes us on the wild journey of founder Andrew Mason's unlikely success and how it could just as easily have never happened at all.” —William D. Cohan, New York Times bestselling author of Money and Power and House of Cards

“More Social Network than Barbarians at the Gate, this is an entertaining tale where the geeks meet money and power, and the skinny guys run away with the cash, only may be they don't.” —Paco Underhill, author of Why We Buy, Call of the Mall, and What Women Want

“Ever wonder why you aren't one mouse click away from becoming a billionaire? Groupon's Biggest Deal Ever gives you a funny, compelling, blow-by-blow account of what stands between a clever idea and an internet fortune. You may never launch into cyberspace like the book's zany and tenacious heroes, but you will gain a new perspective on how ideas blossom and mega-deals get made, and you'll have fun along the way.” —Jerry A. Webman, Chief Economist Oppenheimer Funds and author of MoneyShift: How to Prosper from What You Can't Control

“So what's a three-year-old company--one that's never made a profit, burns cash like there's no tomorrow and has an easily duplicable business model--actually worth? If the company's name is Groupon, the sky's the limit. Frank Sennett tells the gripping story of entrepreneur/carnival-barker Andrew Mason's gutsy decision to turn down a $6 billion buyout offer from Silicon Valley's 600-pound gorilla (Google) and plunge ahead with an IPO that valued Andy's excellent adventure at close to $16.7 billion. Groupon's Biggest Deal Ever proves that, on Wall Street, truth really is stranger than fiction.” —Peter Passell, Editor of the Milken Institute Review and author of Where to Put Your Money Now

In the Press

Read the Kirkus Review of GROUPON'S BIGGEST DEAL EVER The Inside Story of How One Insane Gamble, Tons of Unbelievable Hype, and Millions of Wild Deals Made Billions for One Ballsy Joker. A fast-and-furious account of how Groupon and its young founder bucked acquisition trends by rejecting a $6 billion buyout offer from web titan Google. - Kirkus Reviews

Reviews from Goodreads

About the author

Frank Sennett

FRANK SENNETT is the Editor-in-Chief of Time Out Chicago. He is a graduate of Northwestern University's School of Journalism, earned an MFA from the University of Montana, and has published seven previous books.

Frank Sennett

Martha Williams

Frank Sennett

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