Before Jennifer Fleiss signedupwith the boards of Yale Ventures, high-end leviathan Lanvin and image service Shutterfly, she was a Harvard Business School graduate trying to start a business with schoolmate Jennifer Hyman. The year was 2009, and the 2 intended to teach customers to lease designer clothes bymeansof memberships to a brand-new ecommerce business they called Rent the Runway.
Fleiss acknowledges the considerable psychological health obstacles she dealtwith throughout her period at the New York-based business’s helm, and states that the relationship she shares with cofounder Hyman was crucial to assisting her standfirm.
“The concept that you’re not in this alone because your cofounder implicitly cares simply as much as you do…that’s what kept me afloat in a extremely sane method inthemiddleof losing my mother and having 3 kids while being at Rent the Runway,” Fleiss stated Tuesday in discussion with Bonobos and Pie creator Andy Dunn at Fortune’s Brainstorm Tech conference.
Fleiss, who is now a partner at endeavor capital fund Initialized Capital and the cofounder of scooter travelsuitcase brandname Roll Rider (alongside her 3 kids), grew Rent the Runway into one of the most well-funded customer brandnames of 2010s. After introducing the business, which lets females lease attire, gowns, and formalwear made by high-fashion brandnames and have it provided to their door, Hyman and Fleiss raised almost $700 million in endeavor capital financing. They then grew the business to 1,000-plus staffmembers before a 2021 IPO, in which the business started trading at a $1.7 billion assessment.
The 2 cofounders carriedout 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 business at the time of its IPO, per Forbes, credits this structured responsibility for her success and the strength of her collaboration with CEO Hyman: “There was some difficult things that came up and some amusing things that came up.”
Though Fleiss transitioned to Rent the Runway’s board in 2017 and took a task as the CEO of Walmart personal shopping subsidiary JetBlack (which was shuttered in 2020), she states that she still talks with Hyman daily. Fleiss notes that some of this is business-related, however much of it is “life-related.”
“In the course of Rent the Runway, what I feel the most happy of is my relationship with Jen [Hyman],” stated Fleiss, acknowledging the troubles the company dealtwith amidst the Covid-19 pandemic, when need for official attire all however vanished. (Around this time the business reported web losses of more than $150 million for 2 successive years).
Fleiss