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Rent The Runway Co-Founder Jenny Fleiss Shares Business Advice

Jenny Fleiss, co-founder of Rent the Runway, explained what she calls the “high heel principle,” arguing that young women should take risks and pitch their billion dollar ideas. 

“It’s the idea that whatever you do, you’ve got to bring the confidence to that moment,” she said. “You got to be pitching the billion dollar idea. That’s what [designers] want. And women too often, I think, suffer from this lack of confidence.”

The event, hosted by the Council for Women of Boston College, took place on Oct. 12 night in the Yawkey Center. Beyond her involvement with Rent the Runway, Fleiss is also a venture partner at Volition Capital.

Fleiss said she and her classmate Jennifer Hyman created Rent the Runway while at Harvard Business School. Their idea was to create a business that allows women to rent designer clothing for short periods of time at a much cheaper cost than retail prices. 

“We related to this idea that you often have a lot of events to go to, and yet it doesn’t really make sense to spend money on every outfit,” Fleiss said. “So without any technology or fashion background … we were like, ‘this feels like an opportunity and problem to be solved.’”

Fleiss explained her process of thinking creatively and not relying on strict business plans. Instead, she said, listening to the customer with an open mind is crucial.

“We were always thinking in new ways because we hadn’t run retail stores before. Sometimes you can do it a better way because you have this fresh set of eyes,” she said. “Honestly … being naive can give you this ammo to just charge.”

Fleiss also spoke about how her focus on customer experience sets her business apart. Her goal was not just to sell a dress, she said, but to sell an entire outfit that made people feel special.

“Let’s hope that they view it as something that makes them feel special versus something that was from like a thrift store or something they don’t want to talk about,” she said. “People felt more proud about the fact that they were getting a good deal.”

According to Fleiss, social media also plays an important role in her brand, not only as a marketing tool, but also as a way to cultivate diversity. Social media posts and clothing reviews on the brand’s website allow a wide variety of women to identify with and relate to other women, she said.

“Seeing this woman means I relate to her body type or she looks like she’s living a similar life,” Fleiss said. “People would give us their height, their weight, their bust size, and the story of how they wore it and how they felt in it, and that’s the trusted answer customers are looking for.”

Fleiss also said she has two children, sharing how motherhood empowers her to strive to solidify women’s roles in the workplace.

“Every moment I also really tried to incorporate my kids,” she said. “I think that this was empowering to a group of largely female employees that I constantly had, who would see me bring my child into the office. I was the first one who had a baby there so other people would be like ‘I can bring my child’ … and it led to this nice dynamic in the office.”

Fleiss concluded the lecture by telling a story about turning down another job to develop Rent the Runway. She then urged the crowd to become more comfortable with taking career risks and striving toward goals.

“Someone said to me at one point, ‘You’re actually not taking that big of a risk because you’re betting on yourself’ … Branding it in that way is important,” she said.    

October 21, 2022

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