Jennifer Fleiss on why Rent the Runway focused on empowerment instead of just fashion

For Jennifer Fleiss and cofounder Jennifer Hyman, seeing the way women felt when they put on a dress helped to see Rent the Runway’s viability. To test their idea of providing online designer dress rental, they bought dresses and held fittings. If it didn’t work, they figured they would at least have some amazing dresses.
“The first woman who came in and tried on a dress was totally transformed. She had more confidence. She had more posture, she had an extra bounce in her step,” Fleiss said. “That emotional transformation that women have when they wear an amazing dress is really what we built our business off of.”
A meeting with Diane von Furstenburg also helped. They got an unexpected response (in hot pink bubble letters) to a cold email, and ended up in a meeting with the legendary fashion designer. She wasn’t initially convinced of the idea, but von Furstenburg eventually ended up seeing the benefit. That taught Fleiss a key entrepreneurial lesson: “No doesn’t mean no, it just means not right now.”
Fleiss, who is now director of business development for the growing company with 5 million members and $125 million in VC, shared her experiences and a few tips to close out the TEDCO Entrepreneur Expo near BWI on Wednesday.

Jennifer fleiss of @RenttheRunway tell her entrepreneurial story #E2E15 pic.twitter.com/xid3lLL0HR

— Faith Davis (@faithannedavis) November 17, 2015

For all of the talk of Cinderella stories at the heart of Rent the Runway, Fleiss noted many of the less glamorous aspects of the business that have helped them succeed.
For instance, a key early hire was in data analytics. Helping to track what customers were renting, for how long and other stats helped them understand what they really wanted. When they went to raise money, they also had the data to provide to VCs.
Fleiss also noted that the company runs a “dry-cleaning empire” which is said to be the largest in the U.S. The company also opened a 150,000-square-foot fulfillment center to process orders because no others existed that could perform at the level they required. These seemed like barriers to growing the business, but Fleiss said they “turned them into a competitive advantage.”
Along with execution, timing had an impact.
Fleiss noted that the business started during the recession in 2008, which turned out to be a time when people were more willing to embrace efforts in both economizing and innovation. Graduating from Harvard Business School as the business was getting going, she said many of her classmates were founding startups rather than joining other businesses.

@RenttheRunway Jennifer Fleiss on being an #entrepreneur: "Listen. Learn. Pivot", "Confidence is king" #E2E15 pic.twitter.com/M6TgAJtqkR

— Arielle Newcombe (@ArielleNewcombe) November 18, 2015

As the business has grown, Fleiss said she still feels the same startup energy. That’s partly due to constant change within Rent the Runway. Instead of going into other verticals like men’s and children’s clothes, the company decided to double down on women’s clothes. Recently, it launched a subscription service that envisions the “closet of the future” being a mix of rotated rentals along with owned clothes.
“I think it’s really important to know yourself and to find ways to keep that energy alive, both for the sake of yourself and for the company,” she said.
Fleiss also stays in startup mode by helping other entrepreneurs. She has invested in some companies, but focuses mostly on advising other female founders.
“I like to be the kind of adviser that someone can pick up the phone when they have an issue, rather than come to a quarterly meeting,” she said. “I think that being an entrepreneur can be really lonely, and having advisers can definitely be helpful.”
Fleiss and Hyman also recently started Project Entrepreneur, which will incubate female-founded companies at Rent the Runway’s New York offices. As prominent female entrepreneurs, the cofounders saw a connection between their business model and what they could provide for the community.
“That same kind of empowerment when you put on a great dress relates to female entrepreneurship,” she said.