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Leadership / 20 Questions

Rent the Runway's Jennifer Hyman Shares Her Worst Advice Ever: 'Shut Up and Act Sweet'

The CEO and co-founder explains why she is driven by empowering women in business and in their everyday lives.
Rent the Runway's Jennifer Hyman Shares Her Worst Advice Ever: 'Shut Up and Act Sweet'
Image credit: Courtesy of Jennifer Hyman
- Entrepreneur Staff
Staff Writer. Covers media, tech, startups, culture and workplace trends.
11 min read

A Note From The Editor

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Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

We all have those special occasions -- weddings, graduations, that big job interview -- where we want to look our best,  but we don’t want to drain our bank accounts in the process. As the co-founder of Rent the Runway, CEO Jennifer Hyman’s solution was simple: make high-end designer garments affordable by allowing customers to rent, rather than buy.

Since launching the business in 2009, the company has raised more than $190 million in venture capital and opened five brick-and-mortar retail stores. It has partnerships with 500 designer brands, providing 450,000 pieces of clothing to its 8 million members. And over the last eight years, the company has grown to 1,200 employee, made up of 70 percent females and 71 percent minorities.

Hyman is on a mission to empower women leaders beyond her company. In 2015, she co-founded the Rent the Runway Foundation to help women entrepreneurs across the country develop and scale their own companies.

We caught up with Hyman to ask her 20 questions and find out what makes her tick.

1. How do you start your day?
My husband and I created a “Good Morning” song for our baby Aurora who is 8 months old. We start every day by singing it to her and seeing her huge smiles. Then we pick her up out of her crib and give her a million of kisses. In the morning at home, I'm not functioning as an entrepreneur - I completely limit technology and any work-think - I'm functioning as a mom and a wife. Aurora has made me happier than I've ever been in my life and to start my day with such pure joy makes me the very best version of myself as I enter the Rent the Runway offices.

2. How do you end your day?
Cuddling with my husband and watching Rachel Maddow -- an interesting pairing, I know.

3. What’s a book that changed your mind and why?
Expecting Better: Why the Conventional Pregnancy Wisdom Is Wrong--and What You Really Need to Know by Emily Oster. This book was a godsend during my pregnancy because it provided data-based justification for why it was okay for me to continue to eat sushi and drink wine and consume caffeine -- three things that I love and didn’t want to give up for nine months. The author goes through every pregnancy myth one by one and uses her skills as an economist to debunk them. It’s amazing how much misinformation there is about pregnancy and how many myths are still ingrained into our culture.

4. What’s a book you always recommend and why?
I’ve actually been favoring podcasts over books these days as they’re easy and entertaining to listen to on the commute to work. So I’ve been recommending the NPR podcast How I Built This with Guy Raz. He interviews a whole range of entrepreneurs like John Mackey, the founder of Whole Foods or Sara Blakely, the founder of Spanx, and you hear them tell their authentic, often hilarious and always inspiring stories.

I learned from listening that one of the biggest commonalities propelling successful founders forward is their incredible resilience and positivity despite setbacks, along with their unwillingness to see failure as anything but a stepping stone to later success.

Founders are often great storytellers, because they’re in the business of constantly selling a dream against all odds.

Related: This Entrepreneur Shares The Lesson Every Founder Must Learn to Be a Powerful Leader

5. What’s a strategy to keep focused?
Focus on the big picture and the ‘whys’ behind your work. If your work isn’t mission driven or emotionally resonant to you, it will be very hard to maintain passion and focus over a long period of time, which is critical in entrepreneurship. Too often, ambitious, type A people stay on “the track” going from great college to a competitive job to the next competitive job without stopping to think about what they are passionate about and how they want to spend their time. Personally I am inspired by creating a new behavior in the world: renting clothes that makes women feel like the best version of themselves everyday. Focusing on this mission to empower women not only keeps me focused, but helps me prioritize the right strategic choices for the company.

6. When you were a kid what did you want to be when you grew up?
I still want to be all the things today that  I wanted to be as a kid:  a singer in a Motown band, a Knicks city dancer or a Broadway star. Careers have many chapters, so who knows?

7. What did you learn from the worst boss you ever had?
The worst boss I ever had told me that I intimidated him and he would appreciate it if I stayed silent in meetings. I realized implicitly that the worst bosses are people who try to make the people around them smaller and believe that business and life are a zero-sum game. A great boss does the opposite. She makes her team think big and amplifies their ideas. She gives people on her team outsized opportunities to excel and convinces them that they can reach higher and dream bigger for their career.

8. Who has influenced you most when it comes to how you approach your work?
Definitely my parents. They raised me with self confidence, that I could dream big for my life and the key to achieving those dreams is relentless work ethic. There are a lot of smart ideas out there and far fewer people who are willing to see them through and put in the time and sweat required.

9. What’s a trip that changed you?
I spent the summer after my sophomore year of college travelling around Spain and writing the budget travel guide Let’s Go Spain. It was nearly 12 weeks alone travelling to all of these beach towns and glamorous party meccas like Barcelona, Ibiza and Mallorca. For all the sexiness of the job, the trip taught me how much I hate being alone. I had always considered myself [to be a big] extrovert, but this trip was when I realized that life is most exciting and impactful for me only when I have an incredible group of people around me.

To combat my loneliness during the trip, I made a pact to never go to dinner alone, which meant befriending strangers every day and convincing them to have dinner with me. I’m a bold person, but this completely took me out of my comfort zone.

Related: This Successful Entrepreneur Shares The Trick That Helps Her Tell The Difference Between Being Productive and Being Busy

10. What inspires you?
Love, underdogs, community, positivity and all things associated with summer.

11. What was your first business idea and what did you do with it?
I co-founded my first business with my sister Becky when I was 6, and she was 4. Friendship bracelets made out of colored string and lanyard were totally the fashion thing at the time, so we set up shop in my bedroom for months making them. On a family trip to Hawaii, we placed the bracelets on a beautiful navy velvet board and we would walk the beach selling them to all the tourists.

Being a marketer from a very early age, I put Becky front and center as the lead salesperson. She was adorable and no one could resist her charm. When we got back home, we knew we wanted to expand but making the string bracelets was taxing and our output was low. So we ordered a stock of friendship bracelets from Oriental Trading and continued to sell them on family beach vacations. However, we quickly soured on the business realizing that about a year in, our customers had moved on to a new trend:  slap bracelets. The fashion industry is rough.

12. What was an early job that taught you something important or useful?
In high school, I volunteered every Sunday at the local YMCA with teenagers who have autism. It was a recreational program whose purpose was to give each of these teens, most of whom were nonverbal, an opportunity to have fun and explore new interests. I remember a music class where one of the most disabled of the teens, a girl named Mary, started spontaneously singing the Beatles song “Blackbird” with the music instructors. I was absolutely amazed that a woman who could not speak remembered the lyrics and tune to a song and could sing along. The experience taught me that people’s talents are often found in hidden places and that not everything is visible to the eye. Never underestimate anyone, because the more you engage people, the more beauty they will reveal about themselves.

13. What’s the best advice you ever took?
“Marry the guy who makes you laugh,” which was said to me by every friend, ever.

14. What's the worst piece of advice you ever got?
Shut up and act sweet. You get nowhere in life by shutting up. Make your voice heard always.

Related: Use This Successful Entrepreneur's Scheduling Secret to Have Your Most Productive Day

15. What’s a productivity tip you swear by?
Don’t spend your day managing to inbox zero. Pick one to two problems every day that are important for you to dig into strategically and allot real time to them by cutting off your access to email, texts and social media notifications that seduce all of us out of the zone.

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
A choose a different Spotify playlist based on what I’m trying to accomplish. Music helps me get the job done, relax or get revved up.

17. What does work-life balance mean to you?
I’ve honestly never struggled with work-life balance. I am completely in love with my job at Rent the Runway. It’s my passion and being around my team energizes me. I also love being at home with my husband and daughter. I think about my life with flexibility. We’ve created a culture at Rent the Runway that trusts our employees and their decisions as to how they spend their time. This means that if I want to take my daughter to a music class in the middle of the day, I do that. If I have a work meeting over brunch on a Sunday, I do that. If I’ve been travelling for work for a few days and haven’t been at home, I’ll come in late the following day to work. This strategy involves working at a company that trusts great employees will do a great job no matter where they are.

18. How do you prevent burnout?
I always surround myself with people I love at work and at home. To me, burnout doesn’t come from quantity of work, difficult business problems or hours in the office but from unhappiness. When I’m happy, I’m energized and can get an incredible amount accomplished quickly. And for me, the key to happiness is simple: be around friends and people who don’t take life too seriously.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
Think about someone else’s business. I advise a lot of female-founded startups, both personally and through the Rent the Runway Foundation, which means that I’m constantly listening to entrepreneurs pitch me on new disruptive ideas, describe diverse industries that require innovation and take me through their point of view on customers and trends that make their idea relevant. By listening and immersing myself into their business problems, it helps me think more clearly about my own. I often come back to Rent the Runway after a session advising a fellow entrepreneur with a slew of new creative ideas.

20. What are you learning now? I’m learning that when women speak up together as a united force we can inspire change in the world.

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