Keeping Small Businesses Competitive through Sharing Best Practices of Global Leaders


Jennifer (Jenny) Fleiss, President, is an entrepreneur at heart.  She 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 was responsible for analyzing business growth opportunities through acquisitions, international expansion, and new product strategies.  A natural leader, Jenny founded an essay-editing and coaching service for college applicants, and built the company into an online tutoring service.

In 2007, Jenny began at Harvard Business School where she met fellow co-founder and friend, Jennifer (Jenn) Hyman.  As sectionmates, the two women would meet frequently to discuss entrepreneurial ideas, one of which was Rent the Runway.  Designed to solve the common “closet full of clothes but nothing to wear” problem, Jenn and Jenny launched Rent the Runway in November 2009.

Now a year into business, Rent the Runway has quickly grown to acquire 600,000 members and has signed on 120 top designer brands.  With an inventory of over 15,000 dresses and 4,000 accessories, and entry into new categories such as handbags and undergarment essentials (available for sale), Rent the Runway has become the one-stop shop for life’s special occasions.

Jenny received her Bachelor of Arts from Yale University in 2005 graduating Cum Laude, and her Master’s of Business Administration from Harvard Business School in 2009.


Jennifer Hyman has been the Chief Executive Officer of Rent the Runway since the company’s inception in November 2009.  She is responsible for all areas of the business including technology, fashion, sales, marketing, operations, customer service, and team management, while also serving as the company spokesperson.

Jennifer co-founded Rent the Runway with her Harvard Business School classmate Jennifer Fleiss.  After receiving approximately $15 million from Bain Capital Ventures and Highland Capital, they have quickly built the company to include a 900,000 membership base with 45 employees.  Rent the Runway is a members-only online fashion community that builds customer loyalty for designer brands by enabling women to rent dresses and accessories for all the special occasions in their lives.  As the “Netflix for fashion,” Rent the Runway encourages women to experiment with new designer brands and trends.

Rent the Runway was named as one of Time Magazine’s “50 Best Websites of 2010,” Fast Company’s “10 Most Innovative Fashion Companies of the Year” and Newsweek’s “21 Best Ways to Save in 2011.”  Additionally, Jennifer and her co-founder were named as Inc. Magazine’s “Top 30 Under 30,” Fast Company’s “Most Influential Women in Technology,” and Fashion Group International’s “Rising Stars.”

Prior to Rent the Runway, Jennifer 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 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.  She currently resides in New York City where she enjoys the entrepreneurial lifestyle, neighborhood restaurants, and socializing with her friends and family.



1. What prompted both of you to create Rent the Runway?

JF: The idea originally started when my co-founder Jennifer Hyman was home during Thanksgiving break and her sister had a “closet full of clothes but nothing to wear moment.”  We started RTR so that women everywhere can have the rotating closet they’ve always dreamed of and access to designer brands that otherwise would have been unattainable.

Scenario: you meet a business exec who is looking to fund a cause that already has had enormous positive implications for the community locally and abroad. He wishes to offer $50,000 to a cause that is innovative in its thinking. He has 10 minutes available to speak with you.  What do you share with him about your work?

JH- We are committed to building a business that introduces the next generation of women to designer brands.  We have found that 90 percent of women who use RTR rent a brand they never owned before, and 80 percent report purchasing something from the brand they rented from.  RTR is a true gateway to retail and we are changing the way the female customer shops and manages her wardrobe.

2. For most successful entrepreneurs, there is no typical day so give us a sample of your schedules from start to finish.

JF: I am an avid runner so I try to go to the gym before going into the office.  Once I get to the office there is normally a team meeting.  My mornings consist of brainstorming sessions and discussions about continually improving our processes.  My afternoons are normally filled with answering emails and more meetings.  We are currently expanding our team so I’m currently meeting with a lot of potential candidates for various roles across the business.

3. What are your tricks for time management?

JF: I manage my time with lists.  I have a to do list for each day, and an agenda for every meeting I attend.  I also update my calendar constantly on my laptop and have it synced with my blackberry.


4. Best advice received when you started your career?

JH: The best advice I received was to pursue work that fulfilled me.  I had to ask myself what do I enjoy doing?  I get the most happiness leading a team, coming up with a strategy and being creative. That’s why I know I’d be just as happy being a soccer coach as I am running a fashion company.

5. Given the current economic climate, how has your strategy for building awareness of your work changed for the short-term and long-term?

JF: When we started we were in the middle of a recession and consumers were changing their spending habits.   They were very conscious of cost-per-wear.  Even though we’re slowing coming out of the recession we find that women are still conservative in their spending habits.

6. What’s been your proudest achievement as such immensely accomplished Entrepreneurs?

JH: We’re about to reach one million members so that will be a very proud moment for the Rent the Runway team as everyone has worked incredibly hard to reach this milestone.

7. What are some of the ways that you achieve balance in your life?

JF: I think every entrepreneur naturally feels as though there aren’t enough hours in the day but I find it’s really about appreciating where you are in the moment and making time for those who are important to you.

8. Your top 3 book recommendations for our readers (and why?)

JF:Delivering Happiness” which is the story of Zappos success and “Getting to Plan B” by Randy Komisar who provides great insight into how having a bias towards action is a huge part of starting a company – something we live by at Rent the Runway.

9. What’s your advice to someone interested in starting their own business?

JH: Jenny and I had a rule from the very beginning of Rent the Runway to never write a business plan, because we think that’s a waste of time. Starting a business is a series of iterative tests. Each test eliminates some of the risks of starting a business.

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