An entrepreneur at heart, Jenny transformed her corporate experience and business school training into Rent the Runway, the online one-stop shop for life’s special occasion designer fashion. Since its inception in 2009, Rent the Runway has acquired over one million members and has signed 140 top designer brands, holding an inventory of 25,000 dresses and 4,000 accessories and expanding into new categories such as weddings. Jennifer was named Inc. Magazine’s “Top 30 Under 30” and led Rent the Runway’s success to earn Time Magazine’s “50 Best Websites of 2010” and Forbes’ “15 Names You Need to Know in 2011.”
Q: Please share with us the story of how your professional journey began and has brought you to where you are today.
A: I consider myself an entrepreneur at heart. I started my career at Morgan Stanley in the Strategic Planning Group crafting long-term company strategy and then moved onto Lehman Brothers’ Asset Management Group. At Harvard Business School I met Jennifer Hyman (Jenn) and after many lunches an instant friendship ensued. One Thanksgiving when Jenn was home her sister had a “closet full of clothes but nothing to wear moment” and she thought “there needs to be a solution for this.” Together, we created Rent the Runway so that women everywhere can live the life they dream today by having access to designer brands that otherwise would have been unattainable. We aspired to make high-end fashions as accessible as renting a movie from Netflix and let women know that they can have it all.
Q: What’s your best advice for an entrepreneur in an early/bootstrapping phase? Or in a growth/need to ‘now scale’ phase?
A: Jenn 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 one. We believe it is best to just believe in yourself and jump right into it, test it out, and grow by learning.
Q: Can you share a story of how networking led to a great success?
A: In the beginning stages of the concept we looked to designers and our relationships in the fashion industry to see if this was something that they would consider doing, support and whether they saw a need for it. It gave us the confidence to move forward with the business.
Q: A great negotiation can be game changing for one’s business or life. Studies have shown that men are much more comfortable negotiating and asking for what they want compared to women. What’s your advice to women who are uncomfortable negotiating?
A: The best way to learn is by doing. There are so many capable women out there that have all the tools to do what we have done but just need to find that confidence and do it.
ON Taking Risk
Q: How do you overcome feelings of insecurity, fear or discomfort when deciding to take a risk?
A: I have learned to be confident in my ideas, my strengths and my weaknesses and I believe that you take risks every day, especially in a start-up but you cannot be afraid of it. Instead, confront it and just do it.
ON Time Management
Q: Online calendars, emailing ourselves, post-it notes… I’m still struggling to find the best way to manage my time and to do list? What’s your method?
A: 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.
ON Time Management
Q: How do your prioritize your time?
A: 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.
Q: How would you describe your style?
A: Functional, Fun, Versatile
Q: What’s your best buy ever?
A: I love my Louboutins and my running shoes