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During her time at the University of Hawaiʻi at Mānoa, she was the managing editor of the university’s journalism organization. Working in sports felt like a natural move for Drew, as her dad played professionally, and sports are huge to many Pacific Islander people. Following her graduation, she struggled to find a job, as many graduates often do. She kept taking on different roles until there was an opening for the NFL. Although she didn't get the job she initially interviewed for, she was recommended for another role and hired a few months later. However, after only 10 months, she was fired in 2020. In a podcast, she told the host that she's able to laugh about it now, but at the time, it was devastating.