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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 [Kindle Edition]

Frank Sennett
3.0 out of 5 stars  See all reviews (16 customer reviews)

Kindle Price: $7.59
Sold by: Macmillan

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Book Description

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.

Editorial Reviews


Praise for Groupon's Biggest Deal Ever
Top 10 Business Book of 2012*

“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

About the Author

FRANK SENNETT is the editor-in-chief and president of Time Out Chicago. A graduate of Northwestern University’s Medill School of Journalism, he earned an MFA in creative writing from the University of Montana and has published seven previous books. He lives with his wife and two children in Chicago, Illinois.

Product Details

  • File Size: 427 KB
  • Print Length: 321 pages
  • Page Numbers Source ISBN: 125000084X
  • Publisher: St. Martin's Press (June 5, 2012)
  • Sold by: Macmillan
  • Language: English
  • ASIN: B00779MV8G
  • Text-to-Speech: Enabled
  • X-Ray:
  • Word Wise: Not Enabled
  • Lending: Not Enabled
  • Amazon Best Sellers Rank: #577,476 Paid in Kindle Store (See Top 100 Paid in Kindle Store)
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Customer Reviews

Most Helpful Customer Reviews
2 of 2 people found the following review helpful
3.0 out of 5 stars Great book, but March 2, 2013
Format:Hardcover|Verified Purchase
the Groupon story is unfolding so fast. I wish the book covered the firing of Andy Mason. Frank, go forward in time a year, interview everyone, write an update to your book and send it back in time to us. Please!!!
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4 of 5 people found the following review helpful
4.0 out of 5 stars No need for 50% off to make THIS worthwhile... July 9, 2012
I had heard a lot of stories about Groupon and its goofball, eccentric founder, but there are plenty of things I didn't know in this breezy, thorough look at Groupon's founding, growing pains, and eventual status as belle of the ball in the world of IPOs (after turning down an enormous offer from Google). How Groupon wound up differentiating itself from the pack in the Web 2.0 dot-com universe is a fascinating story, well told by writer Frank Sennett (editor-in-chief of TIME OUT in Chicago, the city where Groupon was born).

My only quibbles are small ones: the lack of an index, and the slightly uneven tone that makes the story significantly more lively and engaging in the later chapters where presumably Sennett was actually covering the events of Groupon as they were happening, rather than playing catch-up from other people's accounts.

Where Groupon will end up in the future is obviously unknown, but regardless, GROUPON'S BIGGEST DEAL EVER will stand as an excellent snapshot of an era where Google, Apple, and Microsoft are working very hard -- and spending unfathomable amounts of money -- to snap up every bit of innovation that comes along.
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6 of 8 people found the following review helpful
By ChgoBiz
Frank Sennett's GROUPON'S BIGGEST DEAL EVER is a great piece on a young company that has experienced so much in such a short amount of time. Although Groupon seems like it has been around forever, Mr. Sennett does a great job of bringing you through the steps of what put them at the forefront of daily deals.

You will read many inside stories that have never been published before. As someone that lives in Chicago, it is hard to go a day without reading about Groupon. Mr. Sennett digs up these stories with his remarkable access to the important players in the Groupon story.

Purchase this book. You will be happy that you did -- and you will know all that goes into your daily deal emails.
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2 of 3 people found the following review helpful
5.0 out of 5 stars Entertaining read! October 10, 2012
By New Mom
For someone who does not particularly find IPOs and start-ups interesting, this book was surprisingly entertaining. I was curious about the company that I purchase many deals from and read this book on a whim because I have enjoyed this author in the past. It was fast paced and made me actually care about the fate of this company. I look forward to reading other books by Mr. Sennett.
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2 of 3 people found the following review helpful
5.0 out of 5 stars Fast Paced & Great Book! July 23, 2012
Frank Sennett is one of the most talented writers today. He has written another fantastic book. If you are looking for a dry business book, you have come to the wrong place. Sennett places us into the high stakes and fast paced world of one of the leading new businesses to hit the scene in years. This is a must read for anyone who would like to learn more about how new companies hit the big time.
Sennett masterfully weaves together insider emails and discussions with how the media portrayed key events at the time. You get a real sense of the motivations of key players in Groupon's rise to astronomical heights. I couldn't put the book down! Can hardly wait for what Sennett has in store for his fans next.
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2 of 3 people found the following review helpful
4.0 out of 5 stars A business book with broad appeal July 3, 2012
It's a mighty challenge to say something lasting about a company as fast-growing as Groupon, but Sennett succeeds admirably. By the end of the book, we understand how Groupon grew, how it works, and have a strong sense of the personality of founder and CEO Andrew Mason. It's a fast-paced account that mimics the breathlessness of the company's rapid rise to market dominance.

My favorite parts were about Oliver and Marc Samwer, the German entrepreneurs who cloned Groupon's business model for the European market, then sold it back before ultimately becoming part of the company itself. If Sennett's planning a follow-up, I would be very interested in something along the lines of "Attack of the Clones"....

I don't use daily-deal sites and, frankly, had no interest in Groupon before reading this book. While reading it, however, I came to root for the company somewhat--after all, where Amazon is much more about a remote and centralized business model, Groupon ultimately helps local businesses find new customers (while making a whopping profit for the principals, naturally). Some industry observers may feel the book could have been more balanced, which is a fair criticism, but as a brisk read for the general or business-inclined reader, it's extremely effective.
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1.0 out of 5 stars shallow December 25, 2013
Format:Kindle Edition|Verified Purchase
i did not think this book offered a lot of meaningful insight and was written in a manner that made me struggle to continue reading
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3.0 out of 5 stars good book, on how NOT to create or run a company February 28, 2013
Groupon's share price went from $20 at IPO to currently around $4.00
I would suggest the austute reader do completely the opposite of what Groupon did in the book.
So from that angle the book is definitely worth reading.
I predict Groupon will pretty much be gone in 5 years, or will be bought out for a lot less than Googles $6B offering.

Groupon is a testament to:
1) the stupidity & greed of investors
2) the deceptive practices of the financial companies which managed the IPO. "Unbelievable hype" is right.

News just in - the CEO has been fired by the board: [...]
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More About the Author

Frank Sennett is a graduate of Northwestern University's Medill School of Journalism, and earned an MFA in creative writing from the University of Montana. His most recent book is 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 (St. Martin's Press).


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