
I’ve been photographed in all of my dresses, the photos are up on social media, I need to wear something new.” I realized what she cared about was the experience of walking into a room and feeling like the best version of herself-she didn’t actually care about the ownership of the dress. I remember being at her apartment and staring at her closet, which was filled with designer clothes that she’d only worn once or twice, and begging her to return the effing dress and instead wear something she already had. When my sister was 25, she got invited to her first wedding, so she went to Bergdorf’s and bought a Marchesa dress for a few thousand dollars that put her into credit card debt. Had Rent the Runway not taken off, I could’ve just gotten another job. And the reality is that you’re not-you’re making a choice for right now, and you’re just gonna see as you go. I think there’s a fear that if you start something new-a new job, a new relationship, a new company-that you’re making this forever choice. Life is not actually filled with as many one-way doors as we might believe it to be. So when I went to business school, and I was taking out hundreds of thousands of dollars of loans to be there, I made one promise to myself: when I graduated, I wanted to be at a job where, when the alarm went off in the morning, I was excited to get up and go do it. I realized that the content of the job is so much less important than the people you’re working with, and the culture of that environment every single day. I got what I thought was my dream job at IMG, and I realized, oh my God, I hate every second of it. And who did I think I was as this 25-year-old doing this? I actually looked to that experience when I started Rent the Runway, because I wanted it to be the opposite of what IMG was at that time.

One of the issues I had there was that I actually was pretty successful I closed deals and made a lot of money, but it was the object of scorn amongst colleagues because I was a very young woman who was bringing in multi-million-dollar deals when some of the older men thought that they deserved to receive the credit. It was a very “every man or woman for themselves” sort of environment. There was not only rampant sexual harassment, but also it was extremely competitive, because most people there were effectively working on a sales commission. I worked at the talent agency IMG, which is now owned by WME, and I was the only woman in an 80-person division. People were scared of getting on planes and traveling, so management was more open to new ideas than they would’ve otherwise been. That was what I first experienced at Starwood: it was actually pretty entrepreneurial when you got there, since there was really nothing to lose. It was actually a super interesting time to work there, because typically, the most innovation happens when things are tough. 11, 2001, so the travel industry was in complete disarray. I started working there as soon as I graduated from college, which was right after Sept.


Regis, Sheraton, Westin, and a whole bunch of other properties. I was a strategy analyst at Starwood Hotels, which owned the W, St. ” More from Hyman, a graduate of Harvard College and Harvard Business School, below.

“ What I was really building was a Willy Wonka land of fashion. “I wanted to give everyone an unlimited closet, ” she says. Now, over 124,131 active subscribers rent on her platform, which offers thousands of options from designers like Ulla Johnson, Staud, and LaQuan Smith. “I realized what she cared about was the experience of walking into a room and feeling like the best version of herself - she didn’t actually care about the ownership of the dress, ” Hyman says. This month we spoke with Jennifer Hyman, CEO and co-founder of Rent the Runway, who first had the idea for the high-end clothing rental service when she was 26 years old, after witnessing her sister drop thousands of dollars on a Marchesa dress at Bergdorf’s, only to wear it once.
#Rent the runway dresses series
In ’s monthly series Office Hours, we ask people in powerful positions to take us through their first jobs, worst jobs, and everything in between.
