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Bobby Allen has held various roles in different companies throughout their work experience. Bobby started their career as a Studio Manager and 1st Photo Assistant at Tom Keller Photography in 2005. In 2008, they became the General Manager at Green Truck until 2010. Following that, Bobby co-owned Bobrad Premium Coffee and Barista Service from 2010 to 2014. In 2011, they worked as a Site Manager at Tact Event Management before becoming a Co-Owner of The Circle Craft in 2013. Currently, Bobby holds the position of Vice President at D. A. Surgical since 2014.

Bobby Allen's education history begins in 1998 when they attended Bowling Green State University. Bobby studied sculpture at this institution until 2001. Following this, from 2010 to 2012, Bobby attended Santa Monica College, focusing on pre-nursing. Later, they pursued a Bachelor of Arts (B.A.) degree at Cleveland State University from 2013 to 2014.