They’ve been referred to as the Fairy Godmothers of Fashion.

With a wave of their wand, any girl can be transformed into the Cinderella of 5th Avenue. Jennifer Fleiss and Jennifer Hyman make their Disney-like magic with RentTheRunway, which they co-founded together in 2009.

Fashion on demand

Fast forward three years later, and it is likely that you or someone that you know have slipped into a designer dress courtesy of RTR. With over 165 designers to choose from, including Vera Wang, Badgley Mischka and Calvin Klein, members can rent high-fashion pieces without the investment-The “Netflix” of Fashion. Women are free to try out new trends and designers in a cost-effective way. With end-of-year galas and wedding season upon us, these co-founders want to give every girl their Cinderella moment. However, they’re the ones with a start-up fairy tale all their own and it is because they got comfortable with failure.

When Fleiss and Hyman met on their first day at Harvard Business School, they probably never envisioned co-owning a company together that now has 2 million users and $30 million dollars in funding after only 3 years in existence. However, that success and growth has presented its own challenges which is why the duo says: mistakes are good. But they make sure to analyze and figure out how to improve those mistake over time.

Fleiss and Hyman are the first to admit and share where they went wrong. One of the major growing pains? According to the pair, not hiring an in-house technology team from the onset of RTR. Building the website was initially outsourced to India because there weren’t many options at the time, and neither of the founders came from a technology background.

They wanted to get the site up quickly to be ready for the upcoming holiday season. Unfortunately, it ended up costing them much more work and cleanup on the back end. They’ve since built an internal team that can manage the technology bumps and bruises day to day– but both wish that they’d done that from the get go.

Getting to “No”

Neither Fleiss nor Hyman have been scared of tough feedback or potential criticism. In fact, they welcomed opinions on how they “got it wrong” as part of their journey in building out the RTR model. The duo conducted several focus groups with thousands of women along with meetings with top designers and retailers to make sure they had the model right.

They couldn’t have been afraid of the word “no” or they would have never gotten anywhere. Rather, Fleiss and Hyman said that those “No’s” were what motivated them to rethink, pivot, and modify their approach. And the success they’ve had with that strategy is evident.

As many of you are entering a time of unchartered territory, whether it’s taking your first job, your first internship, or finally starting your own company, this power-pair of RTR shows you what is possible by letting go of the fear of failure. Go after opportunities with fierce determination regardless of rejection. The potential “no’s” are paving the way to a fairy-tale success story all your own.


Maxie McCoy has a Bachelor’s degree and a Masters from Lehigh in Journalism and Media, respectively. She is the co-writer of Less Work More Money and has experience hosting for Fox Sports Southwest. Follow her @maxiemccoy