Groupon

Founded in 2008 by Andrew Mason, Eric Lefkofsky and Brad Keywell in a bid to bring discount-hungry consumers a trove of cut-rate adventures, Groupon burst onto the scene with all the subtlety of a fire sale. Known for turning everyday activities into half-off extravaganzas, the company's defining moment came in 2011 with its much-ballyhooed IPO, which saw it debut with a bang and a subsequent thud as it struggled to live up to its inflated expectations. Valuation wise, Groupon's worth has been a rollercoaster ride, from its initial $16 billion peak to its more sobering present-day valuation. Despite a slew of awards for innovation and a few triumphs like expanding internationally, Groupon's history is not without its share of pitfalls—executive shake-ups, market saturation, and a reputation for dubious deals have plagued the company. The revolving door of CEOs, with the likes of Mason and more recently Kedar Deshpande, has done little to steady the ship. With a mix of remarkable highs and spectacular lows, Groupon remains a testament to the fleeting nature of digital dalliances in the fickle world of consumer discounts.