Jenny Fleiss

Jenny Fleiss

Co-Founder and Head of
Special Projects of Rent the Runway


New York, NY



How do you approach a vision as a large as Rent The Runway?


Firstly, understand that you need to take one step at a time, otherwise you’ll become consumed with how massive your undertaking is. You need to put one foot in front of the other without becoming daunted by how much work there is to do. Secondly, get your concept out to your consumer and let them react. Jenn and I never wrote a business plan. Instead of focusing on the fine details of your business and financial model, get out there and test your idea. In those early days of testing, it was so fun for us to let our concept evolve in the eyes of our consumers and peers. We decided, “Let’s actually set up shop and see how women respond.” In tandem, Jenn and I also needed to learn whether the business was a good fit for us and if it was something we enjoyed. We quickly became familiar with all of the issues that we were going to have to deal with, like picking up dresses after they’d been used, finding a dry cleaner, dealing with lost or ruined items. For the most part, we were finding our feet as entrepreneurs, which was incredibly energizing and exciting. We were in charge of our destiny every single day, seeing progress, and having a blast doing it. 




How do you overcome fear of the unknown?


You need to push yourself and ask, “What am I so afraid of — that I’ll try something and it won’t work?” Often, there’s not that much to lose. If it doesn’t work out, there’s a really good chance you can leverage the skills you gained and find another job. As far as entrepreneurs go, I’m pretty risk averse. I think you can find ways to mitigate your fear like testing your idea while you still have a job, like how Jenn and I tested our concept while we were in business school. We still had other jobs lined up, but thought, let’s see if we can make this happen — and if we can, we’ll go for it. Even if you do fail, you’ll learn so much from that process. You can take positive things away from every experience if you look at it the right way.


You can take positive things away from every experience if you look at it the right way.

Dress, Joie




How do you discern good advice from bad?


Learning who to listen to is a combination of the respect you have for that person and gut instinct. It comes from listening to a ton of advice and opinions and finding where you stand within that. Also, having a co­founder to act as a sounding board is really helpful. I remember this conversation Jenn and I had with a marketing professor who we loved—she had a great reputation in school and had written all of these wonderful books. She hated our concept. She said that it might work, but that there were a million easier business opportunities, and that what we wanted to do would be extremely difficult. That was a tough conversation to have, but it was a moment when Jenn and I lifted each other up. We thought, there are a bunch of good elements to that advice—because with entry being so hard, we’ll have the competitive advantage. And that has completely proven to be the case. There have been a flurry of knock-offs, but because it’s such a hard concept to actualize, we really don’t have competitors. Another example is an early conversation we had with Diane von Furstenberg, the first designer we reached out to with our initial concept. We pitched this idea of making a rental business for her website and product, and she was not interested at all. I was demoralized, but Jenn pointed out the opportunity that came from not being exclusive to one designer: we could work with a range of brands and rent things out ourselves. That ultimately made what we were doing so much bigger. Having that approach often comes down to how much of an optimistic person you are.


When you’re meeting with someone, it can be helpful to look at their background and think, ‘How can this person best serve what I’m looking for?’ Then you lead the conversation. They’ll probably have thoughts and comments on your entire business — so how can you align your questions with their area of expertise? If you can do that, you’re more likely to get answers that you trust out of the conversation.



How do you adjust to the increased responsibility that comes with a rapid growth rate? 


I find working out really helps. When I’ve have had a bad day or if I’m stressed, I’ll go for a run or to a Soul Cycle class. Playing with my kids puts things in perspective as well. But when I’m overwhelmed and need to get stuff done, I find that sitting down and making a big laundry list of to­-dos is the most effective. I prioritize everything, and if I can’t solve something that day, I’ll write down what the next step is. If you dedicate a bit of time to go through that list, you’ll be able to regain some control. Also, hiring people you trust who you can delegate responsibility to is hugely important. 



Has your style been influenced through Rent The Runway? 


Rent the Runway enables women to have fun with fashion, and that goes for me as well. I’ve always been super efficient in every area of my life. Jenn used to joke about the fact that I would jog to meetings (which I still do sometimes). This sense of efficiency translates to what I wear, too — I’m all about quick and easy outfits. But now there are a few days a week where I’ll take a moment to put something together, and I’ve found a new joy and confidence from it. There is so much power in putting on an outfit that makes you stand a little taller and smile a little brighter. You feel like you can really own that day. I have a new appreciation for that.


Cuff, Lizzie Fortunato; Top, Elizabeth and James; Skirt, Carven; Necklace, Gorjana


For me, it’s not about making the most money or having the most senior title. It’s about optimizing happiness in all areas of my life. There are so many opinions about whether women should work and what balance looks like, but I think we’ve arrived at a place beyond that. I think both women and men are increasingly able to embrace this version of balance that accounts for both family and career. When I speak to women on campus as a mentor, their questions often revolve around structuring a life that accommodates both of those things. Considering technology and the way things are headed, I see more opportunity to create that balanced life.

Bag, Rebecca Minkoff




Has your version of success evolved as your life and your business have? 


Graduating from college, I felt so much pressure to determine my end goal and to know the steps I needed to take in order to get there. That was always a hugely challenging question for me. It was still a question when I went to Harvard Business School, and I had to figure out a way to force myself to answer it. What I’ve come to realize is that you don’t have one clear path. Life is more of a spiderweb and you grow in a ton of different directions, especially as an entrepreneur. For example, I ran our warehouse for 2.5 years. It wasn’t that I necessarily wanted a job in production or logistics, we just needed someone to do it. And I found that not only was I was good at it and enjoyed it, but saw how it could be a competitive factor for our business. I get a lot of passion and energy from learning. Family also plays a role in my version of success. I’ve always valued family and having children, so it feels really good to have reached a place where I can have those things as well as work that stimulates me.





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Photographed by Leslie Kirchhoff

September 2015