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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

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Groupon’s Biggest Deal Ever is the exclusive, behind-the-scenes account of the incredible rise of discount coupon 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 that is disrupting how people shop all over the world. Love him for saving you 50 percent on last night’s Groupon’s Biggest Deal Ever is the exclusive, behind-the-scenes account of the incredible rise of discount coupon 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 that is disrupting how people shop all over the world. Love him for saving you 50 percent on last night’s Indian dinner or hate him for cashing in big when he could be losing millions for merchants and investors alike, Mason---Groupon’s thirtysomething founder and CEO---made an incredible gamble when he turned down Google’s $6 billion buyout offer 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 twentysomethings. The wild ride couldn’t last, but Mason thought otherwise, and with dreams of a potential IPO that could be massive, he liked his odds. But did he make the right decision, or did he blow a chance to continue to grow “the fastest growing company in history”? Is Mason an Internet genius, or is he sitting on another bubble that could burst at any moment? While everyone has an opinion on Groupon, Frank Sennett has written the only inside account. With exclusive access, interviews, and documents that no one outside of the company has seen or been able to report on, Groupon’s Biggest Deal Ever has every twist and turn from start-up to IPO and is the real story of Mason’s audacious gamble and the meteoric rise of Groupon from start-up to $13 billion online giant.


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Groupon’s Biggest Deal Ever is the exclusive, behind-the-scenes account of the incredible rise of discount coupon 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 that is disrupting how people shop all over the world. Love him for saving you 50 percent on last night’s Groupon’s Biggest Deal Ever is the exclusive, behind-the-scenes account of the incredible rise of discount coupon 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 that is disrupting how people shop all over the world. Love him for saving you 50 percent on last night’s Indian dinner or hate him for cashing in big when he could be losing millions for merchants and investors alike, Mason---Groupon’s thirtysomething founder and CEO---made an incredible gamble when he turned down Google’s $6 billion buyout offer 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 twentysomethings. The wild ride couldn’t last, but Mason thought otherwise, and with dreams of a potential IPO that could be massive, he liked his odds. But did he make the right decision, or did he blow a chance to continue to grow “the fastest growing company in history”? Is Mason an Internet genius, or is he sitting on another bubble that could burst at any moment? While everyone has an opinion on Groupon, Frank Sennett has written the only inside account. With exclusive access, interviews, and documents that no one outside of the company has seen or been able to report on, Groupon’s Biggest Deal Ever has every twist and turn from start-up to IPO and is the real story of Mason’s audacious gamble and the meteoric rise of Groupon from start-up to $13 billion online giant.

30 review for 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

  1. 4 out of 5

    Douglas

    Now I know more about Groupon than I need. I'm a fan of well written business books. I've read great ones about Enron's failures and Texaco's 4 billion dollar lawsuit. Of course, like fiction, the more interesting ones are about failures and evil. Groupon doesn't have any scandals so this becomes sort of a fans look at the business. The author is a Chicago business writer, and obviously there is no payoff for him to alienate the largest internet company in Chicago. He hangs out with this crowd. But Now I know more about Groupon than I need. I'm a fan of well written business books. I've read great ones about Enron's failures and Texaco's 4 billion dollar lawsuit. Of course, like fiction, the more interesting ones are about failures and evil. Groupon doesn't have any scandals so this becomes sort of a fans look at the business. The author is a Chicago business writer, and obviously there is no payoff for him to alienate the largest internet company in Chicago. He hangs out with this crowd. But he could have given me more. Maybe cause I'm not signed up with Groupon, I'm the rarity, but I want to know how they do business. Maybe follow a deal from the original cold call all the way to the final accounting? And instead of just mentioning the long days of programming, let us know what problems they were trying to solve. Were they developing the user interface, were they deciding how to store the data? Give us a peek into how a company scales up and rents and buys servers as they grow from nothing to billions in sales.

  2. 5 out of 5

    Simon Yoong

    Fairly good read without going into too indepth. But does not cover the sacking of Andrew Mason as the book was released just prior to that.

  3. 4 out of 5

    Bartosz Majewski

    I have developed a strange affection towards biographies of founders, CEO's and books about specific companies that managed to have an impact on the universe. Whenever i heard a misinterpretation of significant events in life of some company i started to dig to hear the real story. That passion led me to read stories of Jeff Bezos, Elon Musk, Steve Jobs, Felix Denniss, Tony Hsieh or - with this book Andrew Mason, Eric Lefkowvsky and the Samwer brothers. This is a great story - from humble beginn I have developed a strange affection towards biographies of founders, CEO's and books about specific companies that managed to have an impact on the universe. Whenever i heard a misinterpretation of significant events in life of some company i started to dig to hear the real story. That passion led me to read stories of Jeff Bezos, Elon Musk, Steve Jobs, Felix Denniss, Tony Hsieh or - with this book Andrew Mason, Eric Lefkowvsky and the Samwer brothers. This is a great story - from humble beginnings as a charity fundraising site up until couple of months after their IPO. It's definitly not a book that is worth to recommend to anyone however if you like to nerd out on startups, e-commerce and like to know how did they managed to get from startup to IPO in 4 years - it's for you. If you are a nerd about this stuff then i don't even need to add that they did that by ramping up a salesforce that at it's peak had 2.000 sales people globally. The book form sometimes is sometimes lacking but in total it's a good piece of reading if you are into this kind of stuff.

  4. 4 out of 5

    Adriel Lubarsky

    Crazy story, fun characters, decent writing. Not a game changing business book, but an easy read and a good look into fastest growing startup ever. Would love the sequel of “why didn’t they love up to their hype”

  5. 5 out of 5

    Breakingviews

    By Megan Miller Few companies have grown from an idea to a nearly $17 billion company as swiftly as Groupon, the daily deals website. Frank Sennett’s new book, “Groupon’s Biggest Deal Ever,” gives a blow-by-blow account of the startup’s rapid ascent, including its founder’s audacious rejection of a $6 billion takeover bid by Google two years ago. What Sennett’s book fails to deliver, however, is an insight into how Groupon can sustain its position. To investors today, of course, that’s the fundam By Megan Miller Few companies have grown from an idea to a nearly $17 billion company as swiftly as Groupon, the daily deals website. Frank Sennett’s new book, “Groupon’s Biggest Deal Ever,” gives a blow-by-blow account of the startup’s rapid ascent, including its founder’s audacious rejection of a $6 billion takeover bid by Google two years ago. What Sennett’s book fails to deliver, however, is an insight into how Groupon can sustain its position. To investors today, of course, that’s the fundamental question. Since its debut in November, the stock has plummeted, trading this week below the valuation Google put on the company a few years earlier. While Sennett does not explain how durable the firm Andrew Mason built may be, he does effectively draw first-hand accounts of the inner workings of the firm and its executives. In its earlier days, Groupon’s harshest critic appears to have been the CEO himself. He chose to display his Forbes cover bearing his picture with the headline “The Next Web Phenom” at the very entrance of Groupon headquarters in Chicago. But what looks a pretty arrogant move, upon closer inspection, is one of self-effacement. The cover is surrounded by other magazines lauding other doomed tech startups that came and went before Groupon, including Netscape, Napster and MySpace. This wall of shame served as a stark reminder to employees of how quickly the tide can turn for even the most brilliant of ideas. Measured solely by monetary gain, Groupon was an unbelievable success, as Sennett dutifully calculates. It was the quickest firm to achieve $1 billion in sales and the second quickest (behind Yahoo) to gain a $1 billion valuation. And the company itself grew exponentially from catering to merchants and customers in Chicago to being active in 46 countries accounting for 90 percent of the world’s GDP. Its headcount went from two hundred to 9,000 in three years. Groupon faced massive scrutiny leading up to its November 2011 IPO, including a Securities and Exchange Commission investigation into both the company’s books and CEO Andrew Mason’s notoriously frank communication, which included company emails that used humor to deflect media skepticism. In one such email that piqued the SEC, Mason urges his staff to prepare to birth an IPO baby - a breed for which there are no epidurals. Mason’s quirks aside, Sennett argues throughout the book that the founder is a genius with a business sense so astute he alone led Groupon to greatness through a singular vision and dogged work ethic. Despite Mason’s “aww shucks” interview demeanor and self-deprecating jokes, Sennett describes his moves throughout the process of taking the company public and fending off billion-dollar offers as calculated and measured. In this respect, the book is more a hagiography than a company profile. While Sennett, who is a Chicago native and editor of Time Out Chicago, has an obvious soft spot for the Chicago-based business and its chief, he can muster some skepticism. For instance, he notes the staying power of the company depends on maintaining strong, long-term relationships with local merchants and customers. He also highlights the challenge the company faces in forging a customer base largely drawn from local merchants. Beyond Groupon’s ability to expand into such diverse categories as travel while continuing to acquire potential rivals, the company’s fate really depends on future consumer preferences. At the moment, the $6 billion rejection of Google looks to have been a mistake. If Sennett’s optimism for his subject is not misplaced, investors today could look at Groupon shares as something of, well, a coupon.

  6. 5 out of 5

    David

    Very tedious, wordy account of a year or so in the life of Groupon. Tries to hook you in with a promise of a dramatic incident re trying to decide whether to accept a big buyout from Google vs. hold on to ownership until going public, but that ends up not being very central to the story and not that gripping anyhow -- might have been wise to hold out for more, might have been a mistake. I guess if you were completely unfamiliar with the business model (daily deals can be good for a retailer if th Very tedious, wordy account of a year or so in the life of Groupon. Tries to hook you in with a promise of a dramatic incident re trying to decide whether to accept a big buyout from Google vs. hold on to ownership until going public, but that ends up not being very central to the story and not that gripping anyhow -- might have been wise to hold out for more, might have been a mistake. I guess if you were completely unfamiliar with the business model (daily deals can be good for a retailer if they lure in new consumers who go on to buy stuff at regular price, but can be bad if you get overwhelmed by one-time-only demand on which you're making little if any profit b/c Groupon itself is taking a big cut) or with standard reporting on tech companies (by about page 50 I wanted to reach through the pages, grab the author by the arm and scream "I am aware that young guys who work for themselves and have gotten rich tend to dress informally; you do not need to set any more scenes for me by mentioning CEO Andrew Mason's untucked shirt!"), some of this might come as news, but otherwise not much. Other negatives in my reading...... (a) over-reliance on cliches -- someone is always being "brought in to be the adult in the room", everybody "works hard and plays hard" etc. (b) unctuous, flattering perspective on the main Groupon executives. Internal emails presenting their view on one or another controversy are quoted across multiple pages; people who object to being treated like dirt by their bosses are written off as losers; violations of SEC regulations on quiet period before an IPO are a funny quirk....... All told, it reminded me of what Mickey Kaus always refers to as "beat sweeteners", the admiring profiles reporters write of people from whom they want future access. Unfortunately, author didn't do a great job of hiding this purpose, esp. in the long, breathless, gloating account of how his rival from Business Week (at the top of Groupon "shit list" for writing negative stories about the company) got shut out of the pre-IPO company party and got all mad about it! Ha! That will teach her -- next time, say nice things about the fellas, type up their points of view on conflicts, and you too can be invited to the party and given full access!

  7. 5 out of 5

    Andrey Kuznetsov

    Написано предвзято, поэтому невысокая оценка. Но книга акцентирует внимание на следующем: 1. Переход от 0 к 1 (от идеи к продукту, если выражаться терминологией Питера Тиля) наиболее сложный. 2. Далее, если продукт хорошо масштабируется (переход от 1 к N), легко создавать клоны и они растут как на дрожжах. 3. Продукт создаёт новый рынок, клоны увеличивают конкуренцию на нём. 4. С конкурентами можно бороться двумя способами - совершенствовать свой продукт и поглощать их, объединяться. Таким образом об Написано предвзято, поэтому невысокая оценка. Но книга акцентирует внимание на следующем: 1. Переход от 0 к 1 (от идеи к продукту, если выражаться терминологией Питера Тиля) наиболее сложный. 2. Далее, если продукт хорошо масштабируется (переход от 1 к N), легко создавать клоны и они растут как на дрожжах. 3. Продукт создаёт новый рынок, клоны увеличивают конкуренцию на нём. 4. С конкурентами можно бороться двумя способами - совершенствовать свой продукт и поглощать их, объединяться. Таким образом обеспечивается рост. 5. Если идея сильная, рост бизнеса - экспоненциальный. 6. Здесь уже важны процессы, финансовый результат. 7. Немцы - великолепные управленцы, американцы - изобретатели. Фабрика клонов от братьев Самвер, где ключевые ценности - качественное управление и интенсивный рост, - один из великолепных способов ведения бизнеса.

  8. 5 out of 5

    Scott

    The book fell short, so very short. All I wanted was a good story about a high-tech start-up. From Andrew Mason's professional beginnings on through Groupon's hyper-growth phase.... the story remained poorly told. Or a poor story to be told. The events in the book appear disconnected, with limited transitions. Many chapters appeared completely disconnected and contribute little to the overall story. I cared less and less as the chapters went on. If you want a good book on the struggles of inventi The book fell short, so very short. All I wanted was a good story about a high-tech start-up. From Andrew Mason's professional beginnings on through Groupon's hyper-growth phase.... the story remained poorly told. Or a poor story to be told. The events in the book appear disconnected, with limited transitions. Many chapters appeared completely disconnected and contribute little to the overall story. I cared less and less as the chapters went on. If you want a good book on the struggles of invention I recommended instead: The Soul of a New Machine by Tracy Kidder. Written in 1981 it is a well told story and applies as much today as it did 30 years ago.

  9. 5 out of 5

    Stephy

    I admit when I saw this book on my Kindle list of things that Amazon recommended I didn't really read the description. Heck even when I picked it up from the library I didn't really read what the book was about. I started reading and realized it was a nonfictional piece about the history of Groupon. And for a fairly new company it was an intense short history. It was an interesting read, but something that people who are in the business industry or have a bunch of money to invest would find more I admit when I saw this book on my Kindle list of things that Amazon recommended I didn't really read the description. Heck even when I picked it up from the library I didn't really read what the book was about. I started reading and realized it was a nonfictional piece about the history of Groupon. And for a fairly new company it was an intense short history. It was an interesting read, but something that people who are in the business industry or have a bunch of money to invest would find more interesting than your average person. But it was written in a way that was accessible to me which means it was NOT written in buiness lingo. Thank goodness for that.

  10. 5 out of 5

    Erika

    I am not a fan of Groupon. I read this book to see if it would/could change my opinion of it. I admit it was an interesting read. Yet it really actually shows how this business model may not be self sustaining for a long time. I do give Mr. Mason credit on his idea & how he treats his employees & friends. But I will still not be using groupon myself.

  11. 4 out of 5

    Gateacre

    A thoroughly unengaging and one-sided account of the rise of Groupon. The author is a local journalist and clearly a big fan of Groupon - hard questions are avoided, critics happily dismissed. The chapters feel more like separate articles than part of a coherent whole. Okay if you are a big fan of Groupon but there's little serious business insight if that's what you are looking for. A thoroughly unengaging and one-sided account of the rise of Groupon. The author is a local journalist and clearly a big fan of Groupon - hard questions are avoided, critics happily dismissed. The chapters feel more like separate articles than part of a coherent whole. Okay if you are a big fan of Groupon but there's little serious business insight if that's what you are looking for.

  12. 5 out of 5

    Kathleen

    This book had so much potential. The author had great access, but what it turned into reads a little more like a number of disconnected magazine pieces. It was particularly interesting to read accounts of the high-flying IPO after the initial price has fallen by 80 percent.

  13. 5 out of 5

    Andy Chu

    Stumbled upon this in the library... It gave me a completely different perspective on Groupon, which I'd only heard about from its pre-IPO bashing, so I give it a good review. Not sure why this book has such low ratings. It's sort of thin but it reads well. Stumbled upon this in the library... It gave me a completely different perspective on Groupon, which I'd only heard about from its pre-IPO bashing, so I give it a good review. Not sure why this book has such low ratings. It's sort of thin but it reads well.

  14. 5 out of 5

    David

    Great story of a internet start up. Especially like the description of how Groupon's concept evolved and translated into a growing business. Refused to sell out to Google for $6 Bil. Truly ballsy move. I think the jury is still out whether the business can survive the clones. Great story of a internet start up. Especially like the description of how Groupon's concept evolved and translated into a growing business. Refused to sell out to Google for $6 Bil. Truly ballsy move. I think the jury is still out whether the business can survive the clones.

  15. 5 out of 5

    Lawrence Lam

    Easy read, except with some inside baseball. Makes me interested to follow this company closer.

  16. 4 out of 5

    Jean

    it was ok . . .

  17. 5 out of 5

    Lori Grant

    A should-read company profile for knowledge workers, managers, directors, C-levels, and entrepreneurs.

  18. 4 out of 5

    Ed

  19. 4 out of 5

    Ray

  20. 4 out of 5

    Dan Lynn

  21. 4 out of 5

    Christopher Turney

  22. 5 out of 5

    Stephanie

  23. 5 out of 5

    John

  24. 5 out of 5

    Ed

  25. 5 out of 5

    Cassie Forsythe

  26. 4 out of 5

    Pauline

  27. 5 out of 5

    Emily

  28. 4 out of 5

    Rodrigo

  29. 4 out of 5

    Yessica Rusli

  30. 5 out of 5

    Matt Colangelo

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