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University of California, Berkeley, BA

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Rob Solomon

Rob Solomon is President of Groupon, a social commerce startup based in Chicago.

Previously, he was a Partner at Technology Crossover Ventures, which he joined in October 2008. Before that he served as CEO of Sidestep, a travel search site that was bought by Kayak. During his time at SideStep, Mr. Solomon strengthened the management team, added distribution partnerships, and executed a successful growth strategy that included a number of accretive acquisitions. His efforts led to the merger of SideStep with in December 2007, creating the fifth largest Internet travel brand worldwide.

Prior to SideStep, Mr. Solomon spent six years at Yahoo where he was Senior Vice President of Commerce & Vice President and General Manager of the Yahoo! Shopping Group (YHOO) and was instrumental in building one of the largest commerce destinations on the Internet. Earlier in his career Mr. Solomon worked in various roles at Electronic Arts and Cendant Corporation. He is a graduate of the University of California, Berkeley.

Recent Milestones


Company Date Round Size Participants
Trippy 11/2011Venture Round$1.75M4
Tiny Speck 1/2009Seed$1.5M5



  1. Disrupt Alum Trippy Raises $1.75 Million Thanks to Ribs and Fried Chicken ( [edit]
  2. [edit]
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