Jennifer Fleiss is an entrepreneur who has founded and scaled two digitally native businesses from scratch: Rent the Runway and Jetblack.

Rent the Runway was co-founded in 2009 by Fleiss and Jenn Hyman. In 2009, they disrupted the trillion-dollar fashion industry and changed how women get dressed forever by pioneering the ‘Closet in the Cloud’: a dream closet filled with an infinite selection of designer styles to rent, wear and return. 

In this episode from May 2020, we explored the earliest days of Jenny's career, starting in financial services, the subsequent journey which resulted in co-founding her businesses as well as her time spent with Torch Capital, a brand-focused venture fund, where she advises early-stage companies.