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Evan Bailyn began their career in 2005 as the CEO and Founder of Cartoon Doll Emporium, a successful kids website that reached nearly 75 million unique visitors. After its acquisition by Driver Media in 2009, Bailyn moved on to become the CEO of First Page Sage in the same year. In 2017, Bailyn took on the role of Lecturer at Stanford University.

Evan Bailyn graduated with a Bachelor of Arts in English, with a focus on Creative Writing, from Columbia University in 2003. Before their time at Columbia, no specific education information is provided, but it is known that they attended Great Neck South.