Jennifer Fleiss isn’t just another entrepreneur—she’s a game-changer in the fashion industry. As the co-founder of Rent the Runway, she helped redefine how women think about clothing by making designer fashion accessible without the hefty price tag. Her journey is one of innovation, persistence, and thinking outside the box.
From Business School to Big Ideas
Jennifer’s path to entrepreneurship began at Harvard Business School, where she met her future co-founder, Jennifer Hyman. The two bonded over their passion for business and their frustration with the high cost of designer clothing for special events. They saw an opportunity: why buy an expensive dress you’ll only wear once when you could rent it instead?
The idea seemed simple, but executing it was another story. The fashion industry was skeptical—would women really want to rent dresses instead of owning them? Investors were hesitant. But Jennifer and her co-founder didn’t back down.
Building Rent the Runway
In 2009, they launched Rent the Runway, starting small with pop-up rental events on college campuses to test the concept. It turned out women loved the idea. Soon, they secured funding and built an online platform that allowed customers to rent high-end dresses and accessories for a fraction of the retail price.
What made Rent the Runway a success wasn’t just the idea—it was the execution. Jennifer helped shape a tech-driven logistics system that allowed customers to seamlessly order, wear, and return items without hassle. The company expanded beyond just dresses to include handbags, jewelry, and even a subscription model for everyday fashion.
Scaling and Expanding
Under Jennifer’s leadership, Rent the Runway grew into a billion-dollar business, changing consumer behavior and pushing the fashion industry toward a more sustainable, shared-economy model. The company opened brick-and-mortar locations, partnered with major brands, and built a loyal customer base that loved having access to luxury without the commitment.
After years of scaling the business, Jennifer stepped down from her day-to-day role at Rent the Runway but continued her entrepreneurial journey. She went on to co-found Jetblack, a personal shopping service under Walmart’s innovation division, showing once again that she had a knack for spotting consumer trends and turning them into thriving businesses.
Lessons from Jennifer’s Success
Jennifer Fleiss’s story is proof that a simple idea, when executed well, can disrupt an entire industry. She saw an opportunity where others didn’t, took risks, and built a business that changed how people interact with fashion. Her journey is a testament to the power of persistence, innovation, and believing in your vision—even when the industry says otherwise.
