Rent the Runway Co-founder on Building a Billion-Dollar Company

JetBlack Founder Jenny Fleiss

Fleiss and Jennifer Hyman co-founded Rent the Runway — a designer dress rental company now valued at $1 billion. But Fleiss says as women entrepreneurs, they had to overcome challenges that men didn’t. “We were raising venture capital money, and we were doing it on a concept that was a female-oriented business. It also often meant having to translate to groups of male venture capitalists in their 50s and 60s like what was this value proposition.”

Fleiss started her career shaping long-term company strategy in the Strategic Planning Group at Morgan Stanley. She then moved on to Lehman Brothers’ Asset Management Group where she was responsible for analyzing business development opportunities through acquisitions, international expansion and new product strategies. A natural entrepreneur, Jenny founded an essay-editing and coaching service for college applicants and built the company into an online tutoring service.

She served as head of business development and as a member of the firm's Board of Directors. Fleiss managed business growth and long-term strategy planning, including key partnerships and sponsorship sales. She also assists with company-wide infrastructure, project planning, and key logistics decisions. Fleiss is credited with vertically integrating the Rent the Runway entrepreunership feminism operation in the company’s 40,000 square foot distribution center in Secaucus, New Jersey.

Fleiss says that in the decade since fashion success Rent the Runway was founded, the startup ecosystem for women has evolved and improved. Fleiss has started a second company, JetBlack — a personal shopping service that was incubated by Walmart. As a successful entrepreneur, Fleiss’ career advice is simple — do what you love. “JetBlack is a $50 a month membership fee. And once you become a member, we take in some information about your kids, your ages, sizes, brand preferences, and thereafter we can service you with the ease of a text message. So, all you would say is "Paper towels,” and we know for example the exact SKU that you typically order, and we just confirm and reorder.”

Jenny Fleiss is proving that companies built by women, for women can be incredibly successful.

Brut.