Girls In Tech

As a fan of Girls in Tech and as a member of the NYC technology and startup community, I have immense respect, admiration and appreciation for tech startup entrepreneurs and founders – especially female tech startup founders.  So, when I was asked to blog for Girls in Tech, I brainstormed various ways I could channel my interests into the forum and create a space for founders to really tell tidbits about themselves – which brings me to the “Seven Question Series for a Startup Founder.”  Each week, GIT will feature a different female startup founder and ask them seven random questions- some related to their business, their journey, their past, their future, and of course, their passion.

I am starting off the first Seven Question Series with a truly fantastic founder from a fabulous NY startup doing big things: Jennifer Fleiss, Founder and President of Rent The Runway.

For those of you unfamiliar with Rent The Runway, it is the premier destination for luxury designer dress rentals, and provides access to premier dress and accessory rentals online for just 10% of retail price, while working with over 120 renowned designers such as Herve Leger, Missoni, Vera Wang, and Diane von Furstenberg.

1.  Who or What inspired you to start Rent the Runway?

JF:  I’ve always been an entrepreneur at heart and love brainstorming on ways to improve consumer experiences.  At Harvard Business school I would frequently have lunch with Jennifer Hyman, fellow RTR co-founder, to discuss entrepreneurial ideas.  After a Thanksgiving break home to visit her family, Jenn came up with the idea of Rent the Runway because her sister Becky was having a “closet full of clothes but nothing to wear” moment.  We spoke to over a thousand women to evolve the concept and did a test run where we rented dresses to women – it was the pure emotional reaction of a women putting on dresses and feeling so fantastic that they were twirling around in front of the mirror that led to the evolution of the concept and my motivation to make Cinderella moment dreams into a reality.

2.    Who are your own style influencers or favorite designers?

JF:  Some of my favorite designers include Proenza Schouler, D & G by Dolce and Gabbana and Tibi.  I’m also very inspired by some of the stylists we have at Rent the Runway who have such unique everyday style.

3.    How would you describe your management style?  Has it changed since you became an entrepreneur?

JF:  Yes, I think it’s changed since starting Rent the Runway.  I’ve learned to adjust my management style based on who I’m managing and really listen to each team member’s feedback.  I think it’s really important to be flexible in managing a team and determine the best way to manage each individual.  It’s also important to ensure that there’s a balance where employees can work on projects that excite and motivate them while also driving the company forward.    Knowing how fantastic it feels to be an entrepreneur makes me want to give the people I manage maximum responsibility so they too can have the feeling of creating something from scratch.

4.    What is one piece of advice you would give yourself if you could go back in time five years ago?

JF:  Five years ago I would have told myself to really do what I love and not hesitate in taking risks to get there. I spent several years in finance during which time I learned an invaluable amount but I didn’t love what I did on a daily basis.  Entrepreneurship is FUN and teaches you more than any job possibly could so it’s an amazing way to spend time and learn really valuable skills.

5.    If Rent the Runway was not based out of New York City, what other city in the world would you choose as RTR HQ and why?

JF:  I’d probably choose Los Angeles or San Francisco.  In Los Angeles there are so many occasions and events that women are dressing up for, and in San Francisco there is incredible tech talent that’s hard to find in other parts of the country.

6.    Where do you see Rent the Runway in five years?

JF:  In 5 years we really plan to grow the company exponentially so that renting clothing is part of women’s everyday lives.  We plan to change the way women shop for special occasions all across the world.

7.    What are two books that you would recommend to women in the technology and startup community?

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.

WYR:  Would you rather: Never wear a designer dress again  OR  Never be able to read a new book again

JF:  I truly can’t pick!  Both would be terrible to never have the opportunity to do again.  Both are such fun and interesting new ways or learning about different things and constantly having different experiences!