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Dan Woolsey has a diverse work experience, starting in 2002 as a Shooter at DV Depot. Dan then worked as a Director of Photography at The History Channel from 2005 to 2007. In 2003, they became the Owner of Official Pictures while still making movies and TV. From 2008 to 2010, they owned Three Part Media, specializing in marketing and business strategy. In 2010, Dan joined NBC News as the VP of Operations for theGrio.com, overseeing budget, operations, and growth strategy. From 2014 to 2016, they owned and served as the VP of Operations at D2M2 LLC. In 2016, Dan joined Entertainment Studios as the VP of Operations and Editorial Management for TheGrio.com. Dan played a significant role in transforming theGrio.com into a premier NBC News digital property. In 2018, they joined Grand Street Media as a Business Development Specialist, and in 2019, they returned to Entertainment Studios as the VP of Operations for TheGrio.

Dan Woolsey attended Colorado College from 1994 to 1998, where they earned a Bachelor of Arts (BA) degree in Anthropology.