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Earl P. Squirrel has a long and varied work experience. In 2015, they were the President and Chairman of the Board at Purple Squirrel, Inc., a hiring marketplace. From 2005 to 2014, they were the Head Writer/Executive Producer at The Colbert Report, an Olympic Athlete at America in 2014, a World Champion 10th Degree Black Belt Grand Master at USA Karate (USA-NKF) in 2012, a Lead Scientist at CERN in 2012, an Associate Justice at the Supreme Court of the U.S. in 2008, the inspiration for the Dos Equis's man at Euro RSCG Beker-México in 2006, the Artistic Director at the Royal Shakespeare Company in 2003, and the CEO at Goldman Sachs in 2004. In 2004, they were also a Jeopardy! Contestant at CBS Television Studios.

Earl P. Squirrel obtained their Master of Business Administration (M.B.A.) from Harvard Business School between 2006 and 2008. Prior to that, they obtained an Engineer's Degree from Stanford University between 2002 and 2006.