If you’ve ever found yourself buried in a mountain of crumpled clothes and credit card debt, whining about having nothing to wear and maybe downing a bottle of Chardonnay, there’s a good chance Jennifer Fleiss ’05 could be your new best friend and/or the Messiah. (WEEKEND has had more of these moments than we’d like to admit.) Since Rent the Runway’s official launch in 2009, Fleiss and her business partner, Jennifer Hyman, have been eliminating pre-event sartorial angst with their revolutionary “designer-for-less” rental platform. Read on for the Co-Founder and Head of Business Development’s advice for young entrepreneurs, thoughts on why business plans are overrated, and the lunch conversation that started it all. 

Q. You co-founded Rent the Runway in 2008–2009. Tell us a little bit about that experience, and how you arrived at this concept. 

A. My friend in business school, Jennifer Hyman, came over to me one day and we had a lunchtime conversation about how her sister wanted to purchase a $2,000 Marchesa gown to wear to a wedding. She said that all the dresses in her closet were “dead” to her, because she’d already worn them. … [Hyman] and I realized that this wedding was a very high stakes event for her, and that she wanted something new she could look and feel great in. At the same time, we were also looking at trends like the rise of social media, and talking to women. [It was] by talking to women [that] we kind of evolved the concept of Rent the Runway. We’re big believers in not writing a business plan. For this concept, that meant purchasing dresses at retail price and bringing them to undergraduate college campuses like Yale and Harvard for some of our testing. We tested the different aspects of the concept, to see if women would actually pay to rent a dress.

Q. Have you always had a desire to work in a fashion-related industry, or did Rent the Runway really just emerge from that lunchtime conversation?

A. I’ve always been very entrepreneurial and wanted to be an entrepreneur. I don’t think of myself as working in fashion. … My actual job function and the majority of what [Rent the Runway] actually does is all business-oriented. We have eight people here who go to fashion shows and live and breathe that, but for the majority of the business there are a lot of other components that are really important.

Q. Now, over five years since its founding, you’re still working with Rent the Runway. How have things changed?

A. Things are always changing. … In typical startup fashion, there are new challenges every day. We’ve grown very quickly, which is exciting, [but] just managing that growth is a challenge. We’ve implemented things like renting accessories, and we’ve launched products for sale like stockings, underwear and bras, so the styling services that are part of Rent the Runway can give our customers that head-to-toe look. And we now have three retail locations — two in NYC, one in Las Vegas — that allow the customer to actually interact with the brand in a physical setting. We’re constantly listening to consumers’ thinking about what to offer, how we can expand.

Q. Could you tell us a little bit about Rent the Runway’s business strategy?

A. Never before have women been able to access designer fashion at 10 percent of retail price. When we started, fast fashion was emerging and growing but they didn’t really have an economical way of bringing what was on the runway to the average woman. Many of the ways of accessing fashion were eating away at the value of these amazing designer brands and the quality of their products, which was something we wanted everyone to be able to experience. By changing the price point and using the rental model, we’re able to do that. … We hope it’s an experience that will help our customers make better-informed purchasing decisions in the future — even if they can’t buy these brands now, down the road when they can make a purchase they’ll be more informed. Collaborative consumption has entered many industries, but we’re definitely the core innovator in retail in terms of how you think about your wardrobe.

Q. What does a typical day at the office look like?

A. We have over 230 employees now, about 80 of which work in our warehouse. … We have so many different departments — there’s fashion, analysis, technology, marketing — we’re touching practically every area of expertise. It’s been a really fun learning opportunity and has enabled me to “live” in a bunch of different areas. Across the business, we’re very focused on retail, and we’re always funneling the customers’ ideas back into evolving existing concepts and services. I currently spend most of my time with brand management, talking to key partners [Rent the Runway] could work with.

Q. What are some of the most memorable experiences you’ve had since beginning Rent the Runway?

A. One is just when we started the concept, and seeing what an emotional impact our product had on women. And that has continued, with women sending us handwritten notes and photos of them wearing their dresses. Those have always been really memorable for me — it makes us realize that our product is so much more than just a dress.

A second would have to be the fundraising process, just meeting with VCs [venture capitalists] and having them believe in your idea — and seeing how (often male) VCs identify and relate to a “female” product.

I would say, as well, talking to all the designers responsible for creating the dresses we carry. Each breakthrough of getting designers excited about our brand has been memorable. It was exciting to have one of those “wins” each time we signed on a new designer. It’s not easy to sign on designers, so getting them to work with you is a success.

And, finally, our warehouse. We have a 50,000 square foot warehouse right now and we’re moving to a larger one soon. We’ve vertically integrated our own dry cleaning, repairs. … Every time I step into that warehouse and see its work and flow that’s a big achievement; a moment that really wows me.

Q. What’s the best part of working in fashion (or, at least, with a company that participates in the industry)?

A. It’s definitely a fun and very creative industry. … Going to fashion week and all the shows is always fun and enjoyable, and being able to see the transformative effect that fashion can have on a person, the bounce that it can put in someone’s step or the confidence it can give. I guess the best part is getting to know the creativity behind that.

Q. And the worst part?

A. It’s a really hard industry to break into. You have to be persistent, and maybe a little bit naive. [In fashion], no doesn’t mean no — it just means “not right now.” Sometimes designers will tell you they don’t want to work with you. You just have to be really persistent and not let them deter you.

Q. What’s next for Rent the Runway?

A. We’re still just staying very focused on providing these kind of magical experiences for women; letting women access designer brands. We have over 4 million members right now, and we’re just focused on providing better and better experiences and getting even more members.

Q. Do you have any advice for young entrepreneurs?

A. In general, I think the concept of testing your idea out and bringing it to a market — making sure that your concept “has legs,” and seeing the different challenges and getting feedback — is key. Putting yourself on a timeline is important too, setting different “milestones” for yourself as a startup. And not being afraid to fail — realizing that each failure has learning opportunities that come with it.

Q. And specifically for young female entrepreneurs?

A. Often females are a little more realistic, “restrained” with their concept. Encouraging women to think big is really important — to be really aggressive when thinking about how big of a platform their concept could be. Don’t be timid with your concept, because when you’re going to VCs [venture capitalists], they’re looking for the next “billion-dollar idea.” You really need to be able to sell it, to make them believe in your idea.