Before joining the boards of Yale Ventures, luxury goods giant Lanvin and photography service Shutterfly, Jennifer Fleiss was a Harvard Business School graduate trying to start a startup with classmate Jennifer Hyman company. The year was 2009, and the pair’s goal was to teach consumers to rent designer clothes through a subscription to a new e-commerce company called Rent the Runway.
Fleiss acknowledged that she faced significant mental health obstacles while at the helm of the New York-based company and said her relationship with co-founder Hyman was crucial in helping her persevere.
“You’re not alone because your co-founder implicitly cares as much as you do… That’s what allowed me to sustain myself in a very sane way despite losing my mother and raising three kids during Rent the Runway Why,” Fleiss said in a conversation with Bonobos and Pie founder Andy Dunn on Tuesday. wealthbrainstorming session.
Fleiss, now a partner at Initialized Capital and co-founder (along with her three children) of scooter and luggage brand Roll Rider, built Rent the Runway into one of the best-funded consumer brands of the 2010s. one. Hyman and Fleiss raised nearly $700 million in venture capital funding after launching the company that lets women rent clothing, dresses and formalwear made by high-fashion brands and have them delivered to their doors. They then grew the company to more than 1,000 employees ahead of its 2021 IPO, which began with a valuation of $1.7 billion.
The two co-founders check in with each other every two weeks, and they are “forced to sit down” and talk about their relationship – whether they “have something to say or not.” Fleiss held a $12 million stake in the company at the time of its IPO. Forbesattributes her success to this structured accountability and the strength of her partnership with CEO Hyman: “Some hard things have come up, and some interesting things have come up.”
Although Fleiss joined Rent the Runway’s board of directors in 2017 and served as CEO of Walmart’s personal shopping subsidiary JetBlack, which shuttered in 2020, she said she still talks to Hyman every day. Some of them are business-related, but most are “life-related,” Fleiss noted.
“Throughout the process of Rent the Runway, what I’m most proud of is my relationship with Jen. [Hyman]”, said Fleiss, who acknowledged the difficulties the company faced during the Covid-19 pandemic, when demand for formal wear all but disappeared. (Around this time, the company posted two consecutive years of net losses of more than $150 million).
Fleiss reflects on her 16 years of working with Hyman to build Rent the Runway: “There were a lot of hard and special moments. Just like a spouse—no one goes through it with you the same way.
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