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Jon Epstein has a long and varied work experience. Jon began their career in 2007 as Owner and Founder of Purple Gang Clothing. In 2008, they worked as a Manufacturing Facility Operator/Adjuster at AJM Packaging. In 2009, they moved to AJM Packaging Corporation as Accounts Payable. From 2012 to 2015, they worked at THiNKnrg as Business Development, and at The Surnow Company as Assistant Property Manager. In 2016, they joined Lutz Real Estate Investments as Vice President of Acquisitions and Associate. In 2019, they became Owner of Equo Investments and in 2021, they co-founded Rollzi.

Jon Epstein completed their Bachelor of Science (BS) in Economics from Michigan State University between 2009 and 2012. Jon then attended Indiana University Bloomington from 2007 to 2009. In 2016, they earned their Master of Business Administration (MBA) from the University of Florida Warrington College of Business. Jon also attended The London School of Economics and Political Science (LSE), although no degree was earned.