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Reggie James began their career in 2016 as a Partner and Penn Founder at Rough Draft Ventures, where they worked on roughdraft.vc and was available for contact at reggie@roughdraft.vc. In 2017, they founded SUSHI. In 2018, they became the PM at Dreams Media, Inc., the Founder & CEO of Eternal, and the Strategy & Planning at JUMP Bikes, which was later acquired by Uber. At Eternal, they were working to power artists and was hiring. At JUMP Bikes, they were working on special projects, product, expansion, and strategic ops.

Reggie James attended The Wharton School from 2013 to 2017, where they earned a Bachelor of Science (BS) in Strategy and Behavior in Context.