Have a one night stand…with fashion!

Jenn Hyman and Jenny Fleiss launched Rent the Runway with college girls in mind – and they have made having a ‘one night stand’ acceptable…and even more so, fabulous. 

Come on, you guys can admit it – you never want to wear a really stellar dress twice no matter how much you love it. It’s a catch 22 – a situation in which a desired outcome or solution (ie- I want to wear this dress ALL the time EVERY single night) is impossible to attain because of a set of inherently illogical rules or conditions (you simply cannot rewear such a memorable dress not matter how much you love it).

After learning that Jenn (31) and Jenny (28) were Harvard Business School grads I knew I had to pick their brainy brains about the launch of their fashion website and how they have grown their business into such great success.

Here is a little background:

Prior to Rent the Runway, Jenn was the Director of Business Development at IMG where she focused on the creation of new media businesses for IMG’s Fashion Division. She also ran an online advertising sales team at WeddingChannel.com and was an in-house entrepreneur at Starwood Hotels, creating Starwood’s first wedding business which was recognized on the Oprah Winfrey Show for its innovation. Jennifer received her BA from Harvard University and MBA from Harvard Business School. 

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


SH: You probably have a fabulous story about how you came up with this clever and totally practical concept. Please share!

Jenn Hyman: In 2007, Jenny and I met as section mates at Harvard Business School, where over frequent girls’ night, we became fast friends. During a trip home for Thanksgiving, I watched my sister Becky struggle with a “closet full of clothes and nothing to wear” moment. Becky had an upcoming wedding and wanted something gorgeous to wear but her modest salary meant that everything high-end was out of reach. What if, I thought, the Beckys of this world could have access to their dream closet and a new dress for every occasion? What if designers were able to get their pieces into the hands of young, fashionable women and build an addiction for designer fashion?

When Jenn returned to school we met for lunch, and she shared Becky’s dilemma with me. As business school students, we started working on building the business immediately. Jenn and I had a rule from the very beginning of Rent the Runway to never write a business plan because we think that is a waste of time.  In our opinions, starting a business was going to be a series of iterative tests in the marketplace with each test eliminating some of the risks of starting the business.

Jenny and I launched Rent the Runway in November 2009. 


SH: How has it grown since?

Jenny Fleiss: It is hard to believe that we are celebrating our 2 year anniversary this month considering the amount of growth and change the company has undergone. What started as a small founding team working in different coffee shops has now grown to 57 full-time employees in two different offices: our headquarters in the West Village and a 40,000 square foot warehouse in Secaucus NJ.  In fact, just last month we opened our own dry cleaning facility within our warehouse.  Our designer partners have also grown to over 150 top designer brands, and we have nearly 25,000 dresses and 4,000 accessories in inventory. We now offer the full head-to-toe Cinderella experience with saleable items including beauty, intimates and fashion solutions like fashion tape and Spanx. We want to provide that true one-stop-shop experience for all of our members.


Jenn (left) & Jenny (right) with Demi Moore at the Rent The Runway closet

SH: Renting dresses is perfect for college girls who can be fickle (you know it’s true) and want a new dress for every occasion – formals, birthday celebrations…even a Thursday night out.  Did you have the college girl in mind when you came up with the concept?

JH: We definitely had college students in mind while developing our idea.  With full social calendars of their own and limited budgets, college-aged women have a variety of events to rent the runway for. We actually tested the concept at an undergrad dorm at Harvard to garner initial interest.  We purchased dresses at retail (in our sizes in case it did not work out!) and watched girls twirl around in the mirror and share  comments like “How hot do I look!”, “Can you imagine the look on his face if he saw me in this dress?” By the looks on their faces and the descriptions to their friends, we knew we had created Cinderella experiences for them.


SH: How does Rent The Runway on Campus work?

JH: Our on campus Runway Reps are now at over 150 different campuses throughout the country.  Each Runway Rep is the voice of Rent the Runway on their campus, and is tasked with integrating Rent the Runway into their campuses through grassroots marketing efforts, public relations and event planning.


SH: Do college girls inspire any of the choices that  you make when buying for the site? What do you think of fashion trends set by collegiates?

JH: College aged women currently account for approximately 20 percent of our customers and are already renting for all of the occasions in their lives, whether it is sorority recruitment, date functions, 21st birthdays, tailgating parties, spring break, or graduation. They inspire a lot of the decisions on what to buy.


SH: Do you have any design tips for closet organization and how to make it easier to get dressed everyday?

JH: I alternate clothing depending on the season and put out of season items in storage.  I put items that I wear less frequently to the back.  I rely on a lot of storage bins and slim-line hangers which always make me feel more organized!

SH: ATTENTION LADIES! Send the clothes home from school that you are not wearing!


SH: How did you decorate your freshman year dorm rooms at Yale and Harvard?

Jenny Fleiss: Photo collages everywhere!

JH: Making futons chic!


SH: Do fashion and interior design overlap in your life?

JF: Yes! My closet takes up a good amount of real estate in my apartment and I am always looking for organized and attractive ways to display my favorite fashion items. I am currently renovating our new apartment and spending a lot of time planning how to create my dream closet and a space worthy of all the time I spend in it!

JH: Absolutely! I have spent the last two months spending every weekend scouring ABC Carpet and Home in NYC furnishing my new west village apartment. I absolutely love mixing rustic, reclaimed wood with sumptuous patterns and comfortable upholstery. Trying to blend my more trendy style with my boyfriend’s clubhouse style has been a fun challenge.


SH: What is it like working as a team? What came first–your friendship or business relationship?

JH: Friendship followed by business. Having a partner to share the peaks and valleys of entrepreneurship has been amazing for us. We already knew each other’s strengths and our backgrounds brought different skills to our team and we were able to jump right into testing our concept.  We constantly bounce ideas off one another, have honest and open conversations and really complement each other’s skill set.     

JF: As CEO, Jenn oversees all areas of the business including Marketing, Fashion, Analytics, Customer Insights and Technology while I primarily focus on Operations and the executional side of the business in addition to Finance. We are lucky to have very complementary skill sets. It is great having a partner to comfort each another on a bad day and celebrate great moments together.


SH: What makes you go into work every day?

JH: The people we work with are so smart and talented. They are truly fabulous. I feel so lucky to go to work surrounded by such smart, ambitious, creative, & hardworking people all day.

JF: Besides the amazing people who work at Rent the Runway, the memory of that first girl’s reaction to her rental dress always reminds me of why I want to keep Rent the Runway growing.  Everyone deserves their Cinderella moments!


SH: Pure Genius.

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