Jenny Fleiss, is the Co-Founder and Head of Special Projects at Rent the Runway, the company that has, since it’s founding in 2009, made designer dresses accessible to every woman with an internet connection. Jenny and her co-founder, Jenn Hyman, sought to create a company that filled a gap in the retail industry and gave every woman the chance for a “Cinderella moment.” Jenny has been listed on Inc.’s 30 under 30 list and Fortune’s Most Powerful Women Entrepreneurs (you go mama!).

To celebrate Mother’s Day we’ve asked mamas for the best advice they ever got from their own mamas. It’s easy to see the impact this #LADYBOSS’s mama had when she said “why not do both?” Jenny, the mama of two, and soon the be three, seamlessly integrates  family and business. At Rent The Runway, they have created a workspace that empowers women, allowing kids to visit the office, and even arranging fun activities and events for them. Mamas are supported and encouraged to rejoin the workforce, as an appreciated and important part of the Rent The Runway team. We’ll be putting Rent The Runway high up on our list of great places for parents to work (coming soon).

Check out our interview with Jenny below for some RTR insight and inspirational advice to get you motivated.

Tell us your startup story. Was there an ah-ha moment that told you ‘this is something I can make a business out of’? Did you raise money?

Jenn and my real a-ha moment came when we put together a rental pop-up and watched real customers first hand interacting with the designer rentals. The first girl tried on a gold sequined dress, twirled around in the mirror and said “I look HOT!” Her entire persona was transformed and it was then that I realized the service we were providing was to make women feel confident and happy in their lives. Everyone deserves a Cinderella moment became our mantra and we built a service business around this concept that to date rings true. We raised money right out of the gates from Bain Capital Ventures and were the youngest female co-founders to have been funded by them. We have now raised a total of $126M from various top venture firms.

How did you meet your co-founder Jenn Hyman? What made you two click?

Jenn and I went to Harvard Business School together and were in the same section, which meant we took every class and spent every day together. We became very close, very quickly, and loved discussing entrepreneurial ideas together. We also realized that we brought different skills to the table; I came from a finance and strategy background and Jenn brought her sales and marketing background to the table.  We also realized that we enjoyed spending time together, which is important since you spend a ton of time with a co-founder!


What was the hardest part or biggest obstacle you had to overcome to get RTR up and running?

We faced initial difficulty when pitching VC firms. They were predominantly men and just didn’t understand or get the demand for this type of service. We needed to figure out how to frame the message so it would make sense to our audience. To do this we started our pitch showing VC’s footage from the trunk shows we hosted to test our idea that captured the emotional connection the women had with the designer dresses they were trying on. The VC’s were able to see firsthand the changes in the way the women carried themselves and how they interacted with their friends as they showed off the dress.

What’s the best advice you received from a mentor, peer, or family member when you were first starting out?

It sounds simple, but the best advice I’ve received is just to go for it – whatever “it” is to you. So many aspiring entrepreneurs have amazing ideas but let the fear of failure get in the way of going after them, testing and iterating, and making it happen. Jenn and I also constantly remind one another that ‘No doesn’t mean no, it just means not right now,’ a spirit and fortitude that has enabled us to persevere through the inevitable ups and downs of entrepreneurship.

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Can you speak a little bit about your decision to take RTR from an online platform to opening stores; I believe the first was in Bendel’s on Fifth Avenue. Tell us about that process.

We are constantly listening to our customers about what more we can do to provide them the best Rent the Runway experience. We continued to hear them ask for a physical location to try on dresses and see them in person. Like everything we do in our business, we tested the concept first on a shoe string budget, so that we could learn and iterate. With a small dressing room studio in our office and then one inside Henri Bendel’s we found that retail spaces would provide us with a new way for us to connect with our existing customers, gain exposure to new ones and really bring life to the brand. We were also able to prove out that the economics would be favorable and that we could use the stores as service centers to also let customers pick up and drop off their rentals. We now have retail stores across the country in New York, DC, Chicago and Las Vegas.

I know RTR is involved with the Project Entrepreneur Competition; can you speak about that a bit? Why and how you got involved, and what do you love about it?

We launched Project Entrepreneur in partnership with UBS because we wanted to empower other female founders and give them the tools, training, and networks needed to build scalable, economically impactful companies. It’s extremely important to me to offer my guidance and mentorship to other female founders.

In March, we hosted our Project Entrepreneur weekend intensive where over 200 female founders came to New York to participate in the program. Twelve finalists were selected to pitch their businesses to a panel of experts. From that group, three were chosen to receive funding and also invited to participate in a five-week business accelerator program hosted at the Rent the Runway offices.

Jenn and I felt that doing this now, while we were still in the midst of startup life would enable us to offer the most valuable program to women. We additionally found that our brand resonated to consumers as an icon of women run businesses, which we wanted to celebrate and put further meaning behind.

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Any mantra’s you live by? Words to live by?

You’re never fully dressed without a smile. Whether it was the first customer who tried on a rental dress and showed us the transformational emotional power of designer rental, or our injecting real customer photos onto our site, this mantra is meaningful to me everyday. I also find that in leading and inspiring a company, bringing a positive attitude into the office is incredibly important – a smile goes a long way.

No doesn’t mean no, it means not right now. Persistence and perseverance are key in entrepreneurship as is keeping a positive outlook.

What advice do you have for women trying to make that transition from the financial industry into other careers?

Go for it. Even if you fail you will learn a ton on the way. If you aren’t ready to start your own company, try working at a smaller company to get the feel for it. If you aren’t happy in any role I advocate that, rather than sticking it out as resume builder, you should try something new. It’s not worth spending your life doing something that doesn’t make you happy.

What has been the most rewarding part of starting your own business? Any specific moment in time stick out for you?

Watching the company grow from just an idea to an 850-person company has been incredibly rewarding. I’m also very proud of the entrepreneurial spirit that still permeates the Rent the Runway company culture. Everyone feels like a founder here as we are constantly interacting with our customers, testing things out, and injecting new ideas into the company. It has also been amazing to see how our brand has evolved in its meaning to our customers who feel a true connection to the female-empowering business we have built.

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Why did you get into fashion entrepreneurship, could you see yourself doing anything else?

I have always been an entrepreneur at heart, from my early childhood lemonade stand to an online tutoring service I built in college. It was never as much about the industry as it was starting and building something from the ground up, innovating on an industry, and providing a new form of consumer value! I also love spending time advising other early stage companies.

What makes someone a good boss?

Giving your employees ownership over their projects and empowering them to take that opportunity and run with it. Hiring the right people to begin with – who you feel will be a fit with your personality and culture is also important in setting someone up for success. And, when all is said and done, celebrate the wins!

What are you keys to success?

Taking advantage of every minute of every day, whether that means multitasking a meeting and a manicure, running to or from the office for exercise, or having my daughter visit the office after school. I have also had a bias towards action; great things can happen when you just go for it!  Success isn’t just about business for me, it is about being able to enjoy and appreciate every aspect of my life.

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Can you give us any inside scoop of what to expect from RTR?

A lot of exciting things are happening right now at Rent the Runway; we just came off of the launch of our new subscription service Unlimited, which allows you to select three pieces from our inventory and swap them out as many times as you like, giving you access to an endless closet with endless options. This program is exploding and truly revolutionizing the fashion industry!

Our three Project Entrepreneur winners are setting up shop in the Rent the Runway’s office at the end of May to begin their five-week business accelerator program. We are constantly evolving and looking for new ways to innovate!

In light of Mother’s Day can you tell us the best advice your own mother gave you?

‘Why not do both’ was something my mother often said to me encouraging me to go after every opportunity and find a way to fit everything into my life to create fullness and composite happiness. She also constantly reminded me to slow down, smile, and enjoy life.

Photos by Stevi Sesin

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