New York, NY
What was the catalyst for the Real Runway?
For the generation of women preceding the millennials, there has been a raging debate around whether women can have it all. I believe that I represent a new generation of women who think that debate is archaic. There has been a shift. Of course you can have it all, because there are no rules anymore. I see this reflected in our customers — the number one adjective they use to describe themselves is smart. They value themselves for their intelligence, they love themselves and their lives. They are multifaceted women who care about having a great family as well as a great career. Part of Rent the Runway’s vision is to promote this new version of what women aspire to be. I think brands have been talking down to women for years, saying women should feel self-confident. What I’m saying is, they already do. We’re not saying fashion can complete you, or that it should make you feel differently. It’s about celebrating how you already feel about yourself. In many ways, Rent the Runway — and the Real Runway in particular — is just a reflection of what I see in culture and society. It hasn’t been created by me or Jenny, it’s a product of millennial women. The millennial woman to me is an ethos, not an age group. It encompasses the women from all over the world who are creating this tidal shift. So all I’m saying is, this is happening and we should celebrate it.
Women everywhere are pursuing their dreams, whether that’s creating a family, leading a business or both. They’re more comfortable in their own skin, and see fashion as a way to amplify who they already are. This is what we speak to.
How has your experience as a female entrepreneur fueled the initiative?
When Jenny and I started to raise venture capital, for the first time in my life it was clear to me that there was not an equal path for women. I grew up in a family of feminists and there were no limitations to what I could achieve — I never even considered that it might be more difficult for women. The reality is, people are more likely to invest in those who align with entrepreneurs who have a proven track record. Specifically, men who have dropped out of Harvard or Stamford as computer science engineers — like those who have created Microsoft, Facebook, Amazon and Google. So there’s a logical argument that if you invest in people who fit a similar criteria, you will get amazing returns. However you can also get amazing returns by investing in people with different backgrounds, who bring unique perspectives and new creativity to the table. The Real Runway is about democratizing sources of funding. I don’t run a VC firm, but I do have 5 million people coming to the site, and I do have influence. Hopefully by telling these stories, there will be a powerful network effect.
I’m extremely appreciative to have the received funding that allowed me to chase after a dream. Part of my receiving that funding is related to hard work and a great idea, but some of it is sheer luck — and other women deserve that same opportunity.
Coat, Elizabeth and James; Dress, Theory
How has being a disruptor played a role in your success?
I recently went into women’s homes across the country, doing research about our subscription service. Before going into their homes, we had each woman send us her dream closet. Regardless of who she was or where she came from, each woman’s dream closet was full of color, amazing prints and crazy, beautiful shoes. It was like the Willy Wonka land of fashion. But when I looked at their actual closets, they were 75% black and sensible. When I asked why, they said, I had to settle. I had to make a rational choice. So I asked them again about their dream closet — and as they described these incredible clothes, they talked about the experiences they were related to. They had worn the silk kaftan in the South of France, they had danced all night with their girlfriends in the heels, they had killed it in a board meeting in the blazer. I realized it wasn’t about the clothes. Clothes were a symbol of their life experience — a museum for their adventures. When we asked what Rent the Runway meant to women, the word that kept coming up was freedom: Rent the Runway gives me the freedom to have fun, to bring out elements of myself that I don’t otherwise get to do, because it’s not financially rational.
Disruption for me is saying — we don’t live in a world where you have to make that binary decision. You don’t have to commit to that piece of clothing for the rest of your life. We’ve developed the technology and logistics to make rental possible. We can give you the freedom to express all of yourself. That’s the real disruption: giving women the power to have what they want, when they want it for as long as they want it, to amplify who they already are. And that is transformative. Because if you had that freedom, who would you be today? How would that change your life?
How important is it for you to create an inclusive experience in a typically exclusive industry?
The democratization of fashion and the democratization of what is aspirational is incredibly important to me. In 2012, we started allowing customers to post photos of themselves in their rental outfits on our site, in a section called, “Our Runway.” Now hundreds of thousands of women share images of themselves in their outfits. We don’t edit those photos. You can be any size, any ethnicity, have had any experience, and you will be featured on our site. That was a major distinguishing factor for our brand. A lot of fashion brands are scared of promoting women who might not look the part or be aspirational. But what’s aspirational to me is seeing a woman who is happy and having an incredible experience. Isn’t that what we should value? Our customers agree — what people say they love most about Rent the Runway is that they can see other women’s pictures. That they can be a part of a community.
How is a sense of community central to Rent The Runway and Real Runway?
Creating communities has always inspired me, and I’m happiest around people. My family is very close, I’m the oldest of four and have an autistic sister. Growing up with someone who is severely disabled is one of the hardest things in the world, but what it does for a family is bring you together as a team. You have to help each other in all daily difficulties. My parents also had an open door policy, and there were people over every night of the week. Throughout my whole life I’ve mimicked that family culture — from my college experience to the atmosphere at Rent the Runway. I think within chaos exists creativity and fun. It feels natural to be in this environment with so many diverse, talented people. Something I’m really proud of is that Rent the Runway has acted as a training ground for people to learn how to go after their own dream. We’ve had several people start their own companies after leaving ours.
I hope the Real Runway community will act as a support system. It’s crucial for female entrepreneurs to have peers and role models who are fighting the same battles alongside them, because it’s really hard to do this.
Coat, Elizabeth and James; Dress, Theory
Entrepreneurship is glamorized and entrepreneurs are written about in the press as if they’re celebrities. But no one talks about the fact that you think about your work in the shower, when you’re dreaming, and that vacation doesn’t exist. You need to have a network of women who can say, “I get it. I’ve been there.” Because it’s different to be a female leader. The biological timeline has a lot to do with that. Even with the incredible advances in science, if you want to have kids, there’s still an age limit to which you can do that. So all of these important things in your life, like motherhood and marriage, happen at the exact same time as the development of your career. There’s also the factor of how women in the workplace are perceived differently to men. Women who act assertive or aggressive are often viewed negatively by both men and women. You have to be more conscious of the way you act and inspire. A lot of these problems are not unique — they happen to everyone. For that reason I think it’s really important for women to have what I call a “personal board of advisors:” mentors, friends, people you trust who understand the difficulties that arise.
What do you expect of yourself and those who work with you?
It’s incredibly important to have high standards and confidence. You’re a human being who will make mistakes and fall down — but what’s important is allowing yourself to be vulnerable and admit you made those mistakes, and working on growth. That’s what real intelligence, self-awareness and leadership is about. As a leader, you need to be able to say, “Here is the vision. I need your help to get there.” Jenny and I would be nothing without a huge group of people who have contributed their ideas, passion and hard work to get us to where we are. That’s something else that’s falsified in the media relating to entrepreneurship — it takes a team to build a company, who are often working around the clock for you. It is not a solo sport. A core value we celebrate at Rent the Runway is that everyone is a founder, and I expect everyone who comes in here to make this company better.
With so much responsibility, how do you prioritize your time effectively?
I don’t spend time at the office making sure that my inbox is empty by end of day. I identify the three most important challenges that I need to lead and work on in order to bring the business to another playing field. You can organize your time by what I call critical pathways. What are the three or four critical pathways that lead to success within your organization, and how do you ensure that you’re dedicating your time to them? How most people allocate their time is to check off the easiest things on their list first, and are left with the three most difficult things. Those people aren’t entrepreneurs. Because the three most difficult things are what breed change, transformation and innovation. That’s where you should be spending all of your time. Those other little things that you ticked off first don’t really matter.
Dress, Tibi; Earrings, Eddie Borgo
How do the key traits of an entrepreneur differ to the key traits of a CEO?
As the CEO of a business, you need to be able to inspire people, have resilience, focus and a strong work ethic. You can be a successful founder without some of those things. Being a founder is a much better job. You can be creative, observe new needs in the world, constantly test and iterate — but at a certain point you need to build something and ensure it can scale. As co-founder and also CEO of Rent the Runway, I think that being CEO is much harder. You have to turn your vision into a reality. I think there is a key opportunity to help women transition from being founders to becoming CEOs because it can be very challenging. It’s especially difficult when your business is growing extremely quickly. I’m still learning. I get a lot of feedback from my team, my board, my coach, and my peers who are also CEOs. I think the only way to learn is by doing it — by jumping into the deep end of the pool and figuring it out.
Outside of the business, what re-energizes you?
I prioritize the people that I love and spend all of my time outside of work with those people. I wouldn’t be able to do a good job at work if I didn’t have that. My happiness comes from those relationships, so I make time for them, which means that other things drop off. There are so many things I don’t have time for right now, but I wouldn’t be the best version of myself if I didn’t have love in my life.
Being a CEO is the best and worst job in the entire world, often in the same day. The highs and lows I experience are extreme, and because I’m so passionate about it, it’s impossible for me to disconnect. You can rationalize things if you can disconnect, but you inherently can’t disconnect yourself from something that you love. It’s the most exhausting yet most amazing thing I have ever done.
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Photographed by Leslie Kirchhoff