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Rent the Runway founder on how women are dressing up again — in a big way

Jennifer Hyman shares how her company's "closet in the cloud" is changing in a post-pandemic world.
Jennifer Hyman opened up to TMRW about her journey to launching Rent the Runway.
Jennifer Hyman opened up to TMRW about her journey to launching Rent the Runway. Rent the Runway
/ Source: TMRW

We are all works in progress; even the successful women you see owning it on Instagram faced stumbling blocks along the way and continue to work hard to stay at the top of their game. In this series, we're sitting down with the people that inspire us to find out: How'd they do it? And what is success really like? This is "Getting There."

Jennifer Hyman is the CEO and co-founder of Rent the Runway, a company known for renting designer clothing to women for special events, and which recently announced it's expanding into the resale market, meaning customers will be able to purchase lightly used clothes in addition to renting.

Hyman, a self-described "recovering shopaholic," came up with the idea for the company when she noticed that people's relationship to ownership was changing and that they were starting to put more value on experiences. Rent the Runway launched in 2009 and has since become a go-to source for women searching for a great dress to wear to a wedding or a fancy party. Now 40 years old and a mother of two, Hyman opened up to TMRW about her journey to success and how her company is bouncing back from the pandemic in a big, bold way.

What are some of the jobs you had before Rent the Runway?

My first job after college was working at Starwood Hotels. I had this idea to start the first honeymoon registry in the world, where couples could register for their honeymoon, and their friends and family could gift them room nights and activities and flights. It was really my first experience in entrepreneurship and in understanding that entrepreneurship is about recognizing how the world is changing around you and coming up with a big idea and then motivating other people to want to do it with you.

I then went to a company called and ran their advertising sales team. And then I worked at IMG, which is a big talent agency, and I ran strategy for their fashion and media divisions.

I read that at one of your jobs, your boss told you to speak up less in meetings. How did that affect you?

I'm very passionate. I love a great debate. I've always had a lot of really creative ideas, and I've been confident throughout my life to express those ideas. So I got into the workplace and I thought that that was what would be respected. This woman who was more senior in the organization took me aside after a meeting and said, "You know, you should really be more quiet. You're not coming across the right way. You should try to be more sweet, and softer." I walked away from her quickly and started hysterically crying. Someone had basically just told me that I couldn't be myself anymore.

Luckily, a much more senior man in the office saw me crying and asked me to come into his office. I shared with him what had happened and he said, "Jenn, you should just keep on being you. Because one day, that woman is going to be working for you." He gave me the confidence that I could continue being creative and being passionate and speaking up. Had he not intercepted in that moment, I'm actually fearful of my career having had a different arc.

What inspired the idea for Rent the Runway?

Rent the Runway was based around the belief that I had that experiences were going to become more important than ownership, and that this shift would affect basically every category of how we live. We've seen over the past decade that that shift has been rapid in categories like music and media and transportation and hospitality, and that moving from ownership into access or having a subscription actually made those industries bigger because more customers could participate.

What we've been building with the closet in the cloud at Rent the Runway is offering that same level of disruption in the clothing industry by offering a subscription to unlimited clothing, and therefore increasing women's access to fashion.

What were some of the hurdles you faced in getting the company off the ground?

This was a period of time that no one had ever rented clothes before. So we had to convince not only customers that this was an aspirational, smarter way to get dressed, but we had to convince designers that this would be additive to their business and that Rent the Runway could be a partner to them in customer acquisition and data.

Another big challenge in the business was raising funding for Rent the Runway. We were pitching a massive consumer behavior change. We were pitching the idea for a closet in the cloud at a time when the sharing economy was still nascent, at a time when secondhand clothing was still nascent — even when online shopping was still nascent. Women are only raising 2% of the capital that is divvied up to entrepreneurs on an annual basis. The majority of this is not based on anything that women are doing wrong. It's based on the fact that the investor set has historically been biased toward men, especially toward white men. Rent the Runway was a business that not only was founded by two women, but we were catering to women as the primary customer. So it was difficult to explain to investors why this would be so valuable.

What tips to you have for female entrepreneurs when it comes to raising money?

The No. 1 thing women can do to advance their ideas and the possibility of raising money is introducing themselves to the investors — not just saying, "I'm Jenn, I went to this college and here's my job history," but actually introducing those investors to your grit, to your passion, to your resilience, to your ambition.

Because fundamentally, when anyone is investing in the early days, they're not investing based on what your PowerPoint is or even what your idea is — they're investing in you. They're trying to figure out: Is this person someone who will make it happen? Someone who, even if their first idea is the wrong idea, will have the humility to keep on iterating and have the ambitious nature to keep on trying something new?

And simply, will this person help me make more money? Showing the investor who you are and that you're someone who is ambitious and aggressive and passionate and can build a great team of people around you is even more important than convincing them that your idea is right.

The clothing that is being rented right now is the most fashion-forward we've seen rented in 13 years.

Jennifer Hyman, CEO of Rent the Runway

Fashion definitely changed during the pandemic. How did that affect your business?

Our Reserve business, which rents outfits for special occasions to women, was severely impacted by COVID-19. But over 75% of our revenue comes from a subscription (service). Many of our subscribers actually stayed with us last year throughout COVID-19 and they just changed the clothing that they were picking from us. So they were now selecting loungewear and casualwear and activewear, whereas before they had been selecting more workwear and formalwear.

And now we're seeing that closet adapt to (the customer) yet again, because she's re-emerging from COVID-19 in this very celebratory, optimistic, colorful, bold way. The clothing that is being rented right now on our platform, across age segments and across geographies, is the most fashion-forward we've seen rented in 13 years. The inventory itself is the most bold, colorful clothing we've ever seen — more mini dresses, more crop tops, more patterns, more fashion.

Do you rent all of your own clothes?

Oh yeah. I'm probably our top renter. I probably rent 350 days of the year. My closet is effectively dead. I have a big closet filled with things that I own that are like a museum to my past. They don't fit me anymore. They were things that I wore in my 20s. Some of them are just memories of, like, the night I met my husband. My closet — and my sister's closet — was the inspiration for Rent the Runway. We're recovering shopaholics. Being able to have unlimited access to whatever you want to wear is magical. It's given me the freedom to change. My life has changed so much over the past 13 years. When I started Rent the Runway, I was single. I was 27 years old. I was living in New York City and going out all the time. I'm now a mom. I have two kids. I live my life in a different way. I express myself in a different way. And the fact that this closet in the cloud has been able to adapt with me is really incredible.