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Woman Crush: Jennifer Hyman, Rent the Runway CEO

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Jennifer Hyman and her team at Rent the Runway completely upended the way we think about our closets—and we love them for it. This savvy, scrappy entrepreneur talks beauty, business and her best habits in our latest edition of #womancrush.

Name + occupation: Jennifer Hyman, CEO and Co-Founder of Rent the Runway

How did you come up with the idea for Rent the Runway?
I knew something had to change about the way we as women think about our closets when my sister Becky went into credit card debt buying a designer dress to wear to a wedding because she didn’t want to be photographed (and have those photos appear on Facebook and Instagram) in a dress she had already worn. I knew there was something empowering to giving women access to an endless closet of aspirational designer clothing for special occasions and everyday moments alike, and my co-founder and I got to work on Rent the Runway immediately. How you dress directly relates to how you feel about yourself, so my thought was that all women should be able to feel amazing everyday.

What’s been the hardest part about running your business? And what’s been surprisingly easy?
Scaling the company to close to one thousand people in a very short period of time. And with that came the challenge of learning how to have the right processes for running the company as it continued to scale at all different stages of its size. The most surprisingly easy part has been maintaining the mission of the company to empower women as well as the company-held values of scrappiness, big-picture thinking, and positivity that has driven our growth from the very beginning.

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What’s the next evolution of Rent the Runway?
At Rent the Runway we believe that every woman in this country should have a subscription to fashion and a portion of what you wear everyday should be comprised of things that you don’t have to own forever (i.e. things that are rented). Your closet will go into the cloud just like your music or entertainment subscriptions are in the cloud and you’ll be able to access whatever you want to wear, whenever you want to wear it. We implemented our subscription to fashion “Unlimited” this march and its been a mega-hit. Women are using it to supplement what they already own for work, weekends and everything in between.

Is your closet full of rentals?
I am constantly renting. Unlimited, our subscription service, has fundamentally changed how I shop. I use my subscription to fashion to try new trends and designers, bold colors and just add spice to my wardrobe. The only things I end up buying now are basics or loungewear. I love a great pair of comfy pajamas!

What are the wardrobe pieces you consider worth owning?
Every woman needs to invest in beautiful and high quality basics—the perfect jeans, white button down, black skinny pants, great shoes. Before I purchase anything I think to myself whether I’m really going to wear this item more than 10 times. If I will then the economics make sense. I also personally invest in my loungewear. The second I walk into my apartment, I have to get right into pajamas in order for me to truly relax. I’m not the kind of person who wears designer clothing and makeup around my house!

Three things you’re most passionate about:
Just limiting this list to three is super duper hard as I’m super passionate about lots of things like dancing, music, singing, hugs, Italian food, NYC, beaches etc. But in terms of the most important things I’m passionate about here goes it:
1) Having a tribe of people that I love, friends and family, always around me. That’s how I spend my free time outside of work. I’ve always loved existing in a state of chaos with tons of people I care about around me – life is much more exciting and energizing this way. I really don’t think life has meaning without family so I try to nurture my relationships with people – be it my sisters, my mom, my fiance or friends from college. All are extremely important to my happiness.

2) I’m constantly creating and that process – the act of being creative – is really important to me. I love building something out of nothing and I find that ideation is super fun. That’s one of the reasons why I am so passionate about Rent the Runway and creating a new consumer behavior that changes how women live.

3) Helping the disabled community – People who are mentally handicapped and the families of those who are mentally handicapped. Autism is on the rise and it’s a pressing problem. We need to treat the people in our society who are least able to care for themselves and least fortunate with the most love and respect.

Best habit:
Cooking is a fairly new habit for me. I’m one of those urban creatures who prior to a year ago had stored clothing in my kitchen cabinets. But, then my fiance and I signed up for a subscription to Plated and it literally taught me how to cook really yummy food. And, it gave me confidence in the kitchen. I kind of compare it to having a subscription to Rent the Runway Unlimited—once you start experimenting with amazing new trends and designers, you realize that you can pull off new looks and you feel great about yourself. I know I always eat healthier when I cook than when I eat out and it’s super relaxing! Recently I’ve upped the ante and have started entertaining big groups of friends on the weekends and preparing huge meals. Its been a fantastic communal habit I’d love to keep up.

Worst habit:  
I tend to hibernate in the winter. All of my good habits like working out, trying new workout classes or walking to and from work are harder to do when the weather gets cold. From a beauty perspective, I definitely think I apply too much heat to my hair between dry bar blowouts and curling irons—I know I need to give my poor hair a break:)

How often do you wash your hair?
I shampoo my hair once every 2-3 weeks. I have really curly, thick hair and shampooing it too often strips it of it’s natural vibrancy. I scrub my scalp in the shower with water to get product residue out but I don’t like to over do it on shampooing chemicals.

Favorite Living Proof product:
The No Frizz Nourishing Oil and Humidity Shield. They are staples especially in the summer. I’ll apply both after a beach walk and the combination makes my hair so much more manageable!

Biggest hair regret:
I did a Brazilian Keratin Treatment on my hair 7 years ago because I was told that it would be easier to style my hair after. My natural texture is really curly and the treatment completely changed the pattern of my curls for the worst. I was told it would wash out in a few weeks but it’s taken 6 years of growing out my hair to chop off all of the sections affected by the keratin. I wish I had just accepted my wild and crazy natural hair texture instead of trying to alter it.

One thing you would never do to your hair:
I wish I had the strength or ability to blow dry my hair on my own but I just don’t have the skills. If I am styling my hair on my own, I just let it air dry curly and will use different width curling irons to define the texture. I will NEVER cut my hair short. It would fro out and not in a sexy way! I’ve considered it and discussed it with my stylist and have been warned against it.

How long have you been with your stylist?
Getting my hair done a lot for RTR has opened me up to a whole new world of stylists in NYC and I realize that I love mixing it up and going to different people throughout the year and letting them do their thing and be creative with my hair. Its nice to let different people be creative and try slightly different cuts or highlights with my hair. I don’t stress about change.

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

What about your Woman Crush? Name yours.
Sara Blakely, CEO and Founder of Spanx. She is one of the most successful female entrepreneurs of all time. She’s built a brand that represents passion and femininity with a sense of humor. I respect her for writing her own rules in her personal and professional life and I feel very lucky to know her.

What’s the best piece of advice you’ve ever received?
“Man plans and God laughs.” We’re always told we need to have a plan—but in reality you miss out on all of the fun and the serendipity of life if you constantly pressure yourself to have a plan. The bottom line is you need to trust your gut! Rent the Runway would have never come out of me having a plan. I was able to develop the business by having a deep passion for an idea and deciding to go after it.

How do you act confident (even when you don’t feel confident)?
True confidence comes from vulnerability. Being confident enough to raise your hand when you don’t know the answer and you don’t know what to do. To build truly transparent relationships you need to be able to turn to the people you trust and tell them you’re in a difficult situation or you don’t feel confident in your decisions. You have to be confident enough to show you’re human to build bonds.

Most life-changing innovation:
The iPhone. It’s the remote control of life.

Favorite inventor/gamechanger:
I’m very inspired by the Black Lives Matter movement. It’s a game changer and a movement that’s unafraid by creating global awareness on the difficult circumstances of racism and injustice that still exist in our society. The most impactful societal changes have come from brave people who start the conversation.

What’s the next big thing:
Start-ups that change the lives of the working class in this country. A lot of the great innovations and success stories over the past 10-15 years like Amazon, AirBnB, Spotify and Uber have been addressing an upper middle class market. We need to be as entrepreneurial for those who don’t have as much money or time in their day. That is where real positive change will come.

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What do you wish someone would invent next?
A pill to enable you to eat as much amazing Italian food as humanly possible without gaining any weight.

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