Before Jennifer Fleiss joined the boards of Yale Ventures, luxury behemoth Lanvin and photo service Shutterfly, she was a Harvard Business School graduate attempting to start a company with classmate Jennifer Hyman. The year was 2009, and the two aimed to teach consumers to rent designer clothing via subscriptions to a new ecommerce company they called Rent the Runway.
Fleiss acknowledges the significant mental health hurdles she faced throughout her tenure at the New York-based company’s helm, and says that the relationship she shares with cofounder Hyman was vital to helping her persevere.
“The idea that you’re not in this alone because your cofounder implicitly cares just as much as you do…that’s what kept me afloat in a very sane way amidst losing my mom and having three kids while being at Rent the Runway,” Fleiss said Tuesday in conversation with Bonobos and Pie founder Andy Dunn at Fortune’s Brainstorm Tech conference.
Fleiss, who is now a partner at venture capital fund Initialized Capital and the cofounder of scooter suitcase brand Roll Rider (alongside her three children), grew Rent the Runway into one of the most well-funded consumer brands of 2010s. After launching the company, which lets women rent outfits, dresses, and formalwear made by high-fashion brands and have it delivered to their door, Hyman and Fleiss raised nearly $700 million in venture capital funding. They then grew the company to 1,000-plus employees before a 2021 IPO, in which the company began trading at a $1.7 billion valuation.
The two cofounders implemented biweekly check-ins with each other, where they were “forced to sit down” and chat about their relationship–whether they “had something to talk about or not.” Fleiss, who had a $12 million stake in the company at the time of its IPO, per Forbes, credits this structured accountability for her success and the strength of her partnership with CEO Hyman: “There was some hard stuff that came up and some funny stuff that came up.”
Though Fleiss transitioned to Rent the Runway’s board in 2017 and took a job as the CEO of Walmart private shopping subsidiary JetBlack (which was shuttered in 2020), she says that she still talks with Hyman daily. Fleiss notes that some of this is business-related, but much of it is “life-related.”
“In the course of Rent the Runway, what I feel the most proud of is my relationship with Jen [Hyman],” said Fleiss, acknowledging the difficulties the business faced amid the Covid-19 pandemic, when demand for formal outfits all but disappeared. (Around this time the company reported net losses of more than $150 million for two consecutive years).
Fleiss reflects on her 16 years building Rent the Runway with Hyman: “There were so many hard and special moments. Like a spouse–no one lives through that with you in the same way.”
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