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Tommy Flaim began their work experience as a Summer Intern at Ayco, a Goldman Sachs Company, in 2013. The following year, they interned at Lutetium Capital. In 2015, Tommy worked as an Investment Banking Summer Analyst at Citi. Tommy then joined Citi as an Investment Banking Analyst in 2016 and stayed there until 2018. In 2018, Tommy worked as a Category Analyst at Jet.com. From 2019 to 2020, they served as the Manager of M&A Corporate Development at Viacom. In 2020, Tommy founded their own company, Fox & Robin.

Tommy Flaim attended the University of Notre Dame from 2012 to 2016, but did not obtain a degree or specialize in any particular field of study.