Before Jennifer Fleiss joined the boards of Yale Ventures, luxury giant Lanvin and photo service Shutterfly, she was a Harvard Business School graduate trying to start a company with fellow student Jennifer Hyman. The year was 2009, and the two wanted to teach consumers to rent designer clothes via subscriptions from a new e-commerce company they called Rent the Runway.
Aware that she struggled with significant mental health issues during her time at the helm of the New York-based company, Fleiss says her relationship with co-founder Hyman was critical to her perseverance.
“The idea that you’re not alone because your co-founder cares about you as much as you do… that kept me afloat in a very reasonable way, even though I lost my mother and had three children while I was at Rent the Runway,” Fleiss said Tuesday in a conversation with Bonobos and Pie founder Andy Dunn at Assets‘s Brainstorm Tech Conference.
Fleiss, who is now a partner at venture capital fund Initialized Capital and co-founded the scooter luggage brand Roll Rider (along with her three children), built Rent the Runway into one of the best-funded consumer brands of the 2010s. After founding the company, which lets women rent outfits, dresses and evening wear from high-fashion brands and have them delivered to their homes, Hyman and Fleiss raised nearly $700 million in venture capital. They then built the company to over 1,000 employees before an IPO in 2021where the company started trading at a price of 1.7 billion US dollars Evaluation.
The two co-founders held bi-weekly check-ins with each other, during which they were “forced to sit down” and talk about their relationship – whether they “had anything to talk about or not.” Fleiss, who owned a $12 million stake in the company at the time of the IPO, said Forbesattributes her success to this structured accountability and the strength of her partnership with CEO Hyman: “Some difficult things and some funny things have come to light.”
Although Fleiss joined Rent the Runway’s board in 2017 and took a job as CEO of Walmart’s personal shopping subsidiary JetBlack (which closed in 2020), she says she still speaks with Hyman daily. Fleiss notes that some of it is business, but much of it is “life-related.”
“What I am most proud of at Rent the Runway is my relationship with Jen [Hyman],” Fleiss said, acknowledging the difficulties the company faced during the Covid-19 pandemic, when demand for formal wear virtually disappeared. (Around that time, the company was reported net losses of more than $150 million in two consecutive years).
Fleiss looks back on the 16 years she spent building Rent the Runway with Hyman: “There were so many difficult and special moments. Like a spouse – no one experiences it the same way as you.”
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