Risky Business (2005)

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In this whip-smart romance, a woman desperate to keep her start-up afloat is forced to pose as her brother's assistant during a tech competition, hoping a male-led company will be taken more seriously, only to find her secret identity compromised when she has a hot one-night stand with the head of the competition's assistant. When tech founder Jess Cole is struggling to gain funding for her company, she begins to wonder if it's because she's a woman in the male-dominated tech industry—especially due to a former incident and subsequent NDA that's been following her for years. In an act of financial desperation, she applies to a competition for start-ups using her twin brother Spencer's name, pretending to be a man. To her surprise, it works! As though she's discovered the ultimate industry cheat code, Jess and Spencer are invited into the exclusive world of Tech Rumble, an annual innovation competition hosted on the world's stage by tech darling