3 Key Pointers For First-Time Entrepreneurs


by Jennifer Fleiss


When I reflect on these last three years — during which my sectionmate from business school, Jenn Hyman, and I started Rent the Runway — I could never have imagined that our business would reach the scale and success it has today. It’s been an exciting, challenging and crazy journey, and I had the following pieces of advice to guide me through from the onset.





1. Ditch the business plan.

Jenn and I had a rule from the very beginning to never write a business plan. We found that starting a business is more about executing a series of iterative tests, each test eliminating some of the risks entrepreneurs face when launching a company. Instead of sitting around and putting together a business plan based on hypothesis, we knew we needed to test our idea on the ground to see if we could actually promote “renting” as a new consumer behavior.


We had to get scrappy, and we first tested out our idea by going to Harvard with a trunk full of dresses that we let girls try on and rent. Next, we went to Yale and rented out the dresses, but didn’t let women try them on. For the third trial, we sent a PDF out to students that said “call us if you want to rent this dress.” So each time, we were getting closer and closer to what our actual concept was – an Internet dress rental site – to prove that it was really going to work.


2. Don’t be afraid of what you don’t know; surround yourself with people who make you better.

This piece of advice describes how Jenn and I built out our Rent the Runway team from the very beginning. Immediately, we knew that we had to be humble. Here we were with an idea to launch a fashion technology company, neither of us with any background in technology or fashion whatsoever. We had to be honest with ourselves, recognize our own strengths, and more importantly, pinpoint where our skillset was lacking. Once we determined that, we were ready to start looking for a team that would round out our strengths and bring our idea into reality.


Don’t be afraid to enter an industry in which you have no experience. I often think that it is because Jenn and I didn’t have experience in the fashion industry that we’ve been able to rethink some fundamental assumptions about the way it works and create an entirely new category of rental.


However, it wasn’t easy, and I can’t imagine doing it without Jenn. Starting a company is really hard from a workload and execution standpoint, and oftentimes, there’s an emotional roller coaster that comes with it. Since the first day, I have had an incredible partner to share the lows and highs with. When we launched on November 9, 2009, Rent the Runway was featured on the front page of the Business Section of The New York Times. The very best moment of that day was hugging, screaming and jumping up and down with Jenn when we came into the office. Most experiences are better when shared.


3. Share information and make collaborative decisions.

A big mistake that many entrepreneurs make is being hesitant to share information about their concept with others. Jenn and I did the exact opposite. We shared our idea with as many designers, women and investors that we possibly could and utilized their feedback to tweak our original idea. We leveraged the network we had and expanded upon it by taking every meeting. If a certain meeting didn’t produce tangible results in the short term, we always thanked ourselves later for having made that point of contact.


We’ve also taken a lot of suggestions from customers. For example, the idea to pre-alter all of our gowns in three lengths is something that a customer suggested to our stylist team, and we started executing it immediately. We constantly look to our customers and gauge what is resonating with them. During New York Fashion Week, we launched a “Style Council” campaign on our Rent the Runway Facebook Page, encouraging our social media community to vote on their favorite looks from our designer partners’ runway shows. Essentially, we’re incorporating them into our buying process, where their feedback is instrumental in choosing what products we decide to offer on our site.


Similarly, I think that part of being a good leader is involving your team in key decisions to ensure that it’s a collaborative step forward for the entire company. To be constantly taking feedback from your entire organization is to make your company a warmer, more exciting place for people to work.


Jennifer Fleiss is an entrepreneur at heart. Jenny worked at Morgan Stanley and Lehman Brothers before she co-founded Rent the Runway, designed to solve the common “closet full of clothes but nothing to wear” problem, in 2009. Now, Rent the Runway has quickly grown to acquire over one million members and has signed on 140 top designer brands. It has become the one-stop shop for life’s special occasions.


Photo Credits

Swiveler | The YEC