Create & Cultivate 100: Entrepreneur: Jennifer Hyman


Once upon a time, you had to buy an expensive new dress if you were invited to a formal event.

Then Jennifer Hyman came along and, in her words, “democratized fashion.” Jennifer saw whitespace in the fashion world: Women going into debt on formal wear they needed for a single event. And so she took it upon herself to fix it, and thus, in 2009, Rent the Runway was born. Simply choose a dress to have shipped to your home, wear it, and return it, either via mail, to a RTR store, or at a designated WeWork dropbox—Hyman wants to make it easy for you. Repeat as desired (warning: RTR is pretty addictive).

Jennifer is a visionary and the ultimate disrupter in the fashion industry, and we can’t wait to see how she continues to revolutionize the way we get dressed in 2019 and beyond.

Rent the Runway has been celebrated for disrupting the fashion industry in so many ways. Where did the idea start?

I had the idea when I watched my sister Becky go into credit card debt buying a designer dress to wear to a wedding. She didn’t want to wear a dress she already had in her closet as she had been photographed in everything already and the photos were up on social media. I realized that what Becky and what millions of women care about is the feeling of walking into a room and feeling your most confident.

I also was thinking through the huge expense of closets filled with clothes that we didn’t wear—and feeling like we had to splurge to buy the designer pieces we aspired to. I loved the idea that RTR could democratize fashion for all.

Tell us about the new WeWork and Rent the Runway partnership. What inspired it?

This is one of my favorite partnerships we’ve ever done! In October of this year, we launched a national Drop-off Box network in 15 WeWork locations across 6 cities in the US: New York, San Francisco, Los Angeles, Chicago, D.C., and Miami. Our customers can use the dropboxes to return clothing they’ve already worn and instantly order their next items. With the dropboxes situated in WeWork lobbies we were eager to make it convenient and easy for our customers to return their rentals.

RTR and WeWork members already using the drop-off boxes daily. We’ve heard from so many customers requesting dropboxes in their neighborhoods—so stay tuned!

What do you think is key to finding a great co-founder for a business?

Look for someone you have fun being around and who has a fundamentally different skill set than you do. Therefore, you are both bringing something special and important to the table.

What about your job makes you feel the most fulfilled?

I’m proud that an idea I had in my sister’s apartment has impacted millions of women’s lives and empowered diverse women to feel like the best versions of themselves before important days in their lives. I also feel incredibly fulfilled when I think about the team that we have built at RTR—it is an extremely passionate, innovative group of people who are constantly pushing the boundaries of what’s possible. And most, the team is incredibly fun and kind! It’s amazing how many RTR team members have met their best friends, significant others or future co-founders at Rent the Runway. To create a community—an extended family— that lives beyond me is one of the most incredible things in life.

When you hit a bump or hurdle in your career, how do you find a new road + switch gears to find success?

Keep a positive attitude, learn as much as you possibly can from the hurdle and keep moving. Hurdles are part of the ride and the more you get used to these daily challenges—big and small—and view them as opportunities for growth, the less they’ll slow you down.

Hurdles are part of the ride and the more you get used to these daily challenges—big and small—and view them as opportunities for growth, the less they’ll slow you down.

Who are the first three people you think an entrepreneur should hire?

Early team members at a startup need to be all-around athletes—people who are willing to roll up their sleeves and do anything and everything they can to make the business grow from answering customer service calls to implementing wacky marketing campaigns to taking out the trash. Jenny and I looked for a can-do attitude and a founder mentality because there is no real plan at the beginning. Every day is different, incredibly fast paced and exciting. From a tangible skills perspective—if your business has technology at its core, one of your first hires has to be able to code.

Who inspired you the most in your life growing up?

My parents are my role models. They have what I think is the most important quality in people: resilience. They have always maintained a positive attitude despite any challenges thrown their way and have inspired me to be resilient, tenacious and to always go after my dreams.

Whose career is inspiring you today?

I’m inspired by anyone who goes after their own happiness in every part of their life and doesn’t make their career the only thing in their life. This takes self-awareness and honesty to understand what it is on a personal level that makes you happy. For me, it’s a close, loving family and circle of friends that make day-to-day life fun.

If you could live a day in the life of anyone else, who would it be?

Beyonce—I want to understand what it would feel like to be able to dance and sing like that!

To create a community—an extended family— that lives beyond me is one of the most incredible things in life.

What are the common challenges you've seen among female business owners and entrepreneurs?

A big challenge is that the capital is still largely controlled by men—and many men are not as confident in or passionate about businesses that cater to women (which is bizarre as women control over 80% of household purchases!). It’s a case of not being able to see the world as clearly because you lack the desire or willingness to step into someone else’s shoes.

When beginning to raise venture capital it became very clear to me that this was not an equal playing field for women. Growing up I was told there were no limitations to what I could do—the idea that being a woman would make it more difficult to raise money never crossed my mind. But, many male investors couldn’t understand the potential for RTR, the largeness of the idea and the extent of demand for a closet in the cloud. Therefore, businesses like RTR likely have raised less money than they should have and therefore don’t have as much capital to swing for the fences.

What are you most excited for in 2019?

First and most importantly, I’m having my second baby in 2019—so I’m really excited to meet him or her and continue to build my family with my amazing husband. We also have so much in store for Rent the Runway in 2019 especially related to making our subscription to fashion an even bigger, more important and easier part of women’s lives. It’s incredible how many new brands are coming on board so that our customers can have something to wear for every imaginable occasion.