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Holly Hager has a long and varied work history. Holly began their career in 1987 as a Legal Assistant (Paralegal) at Fried, Frank, Harris, Shriver, and Jacobson. Holly then moved to Shearson, Lehman Bros. in 1989 as a Senior Legal Assistant (Paralegal). In 1991, they began teaching at Fordham University as a Teaching Fellow and Adjunct Professor. In 1995, they became an Associate Investment/International Consultant at Buck Consultants/Buck Investment Services. In 2003, they were an Executive Assistant at LIZ CLAIBORNE INC. and in 2005, an Executive Assistant at Henri Bendel. From 2011 to 2020, they were the Founder of Curatious, where they developed entrepreneurial skill sets including how to scale an online business, product development, content marketing, financial reporting, sales, and analytics. Currently, they are the Principal & COO at House of Puff Inc., where they work with the founder in all aspects of the consumer products startup, with primary responsibility for operations, sales, SEO, finance, and legal. Holly is also heavily involved in content marketing, product development, growth strategy, and daily operations.

Holly Hager received their Bachelor of Arts in Philosophy from Alliance University in 1987. Holly then went on to pursue their Master of Arts in Medieval Studies from Fordham University in 1992. Lastly, they were an ABD (all but dissertation) for their PhD in Holly'story from Fordham University from 1992 to 1998.