Rent the Runway cofounder Jennifer Fleiss on why cofounder relationships are critical for mental wellness in the startup game
Before Jennifer Fleiss joined the boards of Yale Ventures, luxury fashion company Lanvin, and photo service Shutterfly, the Harvard Business School graduate was trying to start a company with fellow entrepreneur Jennifer Hyman. It was 2009, and the two wanted to teach consumers how to rent designer clothes through a new e-commerce subscription business they called Rent the Runway.
Fleiss acknowledges the significant mental health challenges she has faced throughout her time leading the New York-based company, and says her relationship with co-founder Heyman has been vital in helping her persevere.
“The idea that you’re not in this alone because your co-founder cares about you just as much as you do… that’s what kept me alive in a very sane way in the midst of losing my mother and having three kids while at Rent the Runway,” Fleiss said Tuesday in a conversation with Bonobos and Pie founder Andy Dunn at luckBrainstorm Tech Conference.
Fleiss, now a partner at venture capital fund Initialized Capital and co-founder of scooter bag brand Roll Rider (along with her three children), has built Rent the Runway into one of the most funded consumer brands of the 2010s. After launching the company, which lets women rent designer dresses, gowns, and formalwear from high-end fashion brands and have them delivered to their door, Heyman and Fleiss raised nearly $700 million in venture capital funding. They then grew the company to more than 1,000 employees before its 2021 IPO, when the company began trading at $1.7 billion. evaluation.
The co-founders held biweekly check-in sessions with each other, where they were “forced to sit down” and chat about their relationship — whether they had “something to talk about or not,” said Fleiss, who had a $12 million stake in the company at the time of its IPO. ForbesShe attributes her success and the strength of her partnership with CEO Heyman to this structured accountability: “I’ve faced some tough things and some funny things.”
Although Fleiss moved to Rent the Runway’s board in 2017 and took over as CEO of Walmart’s private shopping subsidiary JetBlack (which closed in 2020), she says she still talks to Heyman every day. Some of it is business-related, she says, but a lot of it is “life-related.”
“Throughout Rent the Runway’s history, what I’m most proud of is my relationship with Jen[Heyman],” Fleiss said, acknowledging the company’s struggles amid the COVID-19 pandemic, when demand for formalwear virtually disappeared. (Around this time, the company began selling formalwear at deeply discounted prices.) reported net losses (Over $150 million for two consecutive years).
Reflecting on her 16 years creating Rent the Runway with Heyman, Fleisch says, “There were some really tough and special moments. Like a husband — no one lives those moments with you the same way.”
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