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 out an organization with fellow student Jennifer Hyman. The yr was 2009, and the 2 desired to teach consumers to rent designer clothes via subscriptions from a brand new e-commerce company they called Rent the Runway.
Aware that she struggled with significant mental health issues during her time on 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’s now a partner at enterprise capital fund Initialized Capital and co-founder of scooter luggage brand Roll Rider (along together with her three children), built Rent the Runway into one in all the best-funded consumer brands of the 2010s. After founding the corporate, 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 enterprise capital. They then built the corporate to over 1,000 employees before going public in 2021, where the corporate went public with a market value of $1.7 billion. Evaluation.
The two co-founders held bi-weekly check-ins with one another, during which they were “forced to sit down” and speak about their relationship – whether or not they “had anything to talk about or not.” Fleiss, who owned a $12 million stake in the corporate on 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 day by day. Fleiss notes that a few of it’s business, but much of it’s “life-related.”
“What I am most proud of at Rent the Runway is my relationship with Jen [Hyman],” Fleiss said, acknowledging the difficulties the corporate faced through the Covid-19 pandemic, when demand for formal wear virtually stopped. (Around that point, the corporate was reported net losses of greater than $150 million in two consecutive years).
Fleiss looks back on the 16 years she spent constructing 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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