Jenny Fleiss is one of those entrepreneurs who can attribute her success to perseverance. She and her business partner stuck to their Rent the Runway idea in the face of skeptical fashion designers and male venture capitalists who may not have been aware of the emotional attachment women have with clothes. On top of that, they did not have much experience either in fashion or digital retail.
Yet today, Rent the Runway is a ground-breaking, billion-dollar company. Co-founded by Fleiss and Jennifer Hyman in 2009, it provides people with a wide array of clothes they can rent for a particular occasion and return once it’s over.
And Fleiss continues to disrupt the electronic retail industry with Jetblack, a personal shopping and concierge service that combines the convenience of e-commerce with the customized attention of a personal assistant.
Speaking at NJBIA’s Women Business Leaders Forum on Friday, Fleiss said she had two rules for entrepreneurship: always test your product with consumers early on and hold yourself accountable to a timeline.
“To everyone out there who has a side hustle or a concept, the sooner you can get your concept out to consumers the better, because in the meantime, you may be wasting your own time,” Fleiss told the audience of 500 at Ocean Place Resort & Spa in Long Branch.
Fleiss and Hyman tested their idea while they were still in college by buying a lot of dresses (in their own sizes, so they could at least wear them if things didn’t work out), and renting them out for graduation. Their first customer grabbed a sequin dress, twirled around in it, and said, “I look hot!”
That’s when they knew they had something.
“She was transformed,” Fleiss said of the young woman. “And in that moment, which I‘m sure a lot of women relate to, we understood that that’s our business; we are renting that feeling, that experience.”
Testing with consumers tells you more than just if they will embrace the idea; it lets you see everything that’s involved in the business, whether it’s viable, and, perhaps more important of all, whether you will like doing it.
The popup shops taught them about getting the dresses to the dry cleaners, and how the clothes fit in the mail when people returned them. It showed they were go-getters, that they put their own money on the line and did make revenue. And those venture capitalists who would never get the idea? Fleiss said they videotaped customer’s reactions.
“That’s how we started every pitch to every VC, with videos that showed rather than told about how we were renting the Cinderella experience, this Cinderella feeling, with fashion,” Fleiss said.
Still, success took a long time, and Rent the Runway experienced a lot of rejection before it arrived. She also took the same methodical approach to launching Jetblack.
But those challenges beg the question, as NJBIA’s Michele Siekerka asked during Friday’s fireside chat-style interview with Fleiss: How do you know when to give up on an idea that’s not going to work?
“I know there are many, many, people in this room, who ask themselves, how many times do I have to bang my head against that wall, and when do I just give up and go home?” Siekerka asked.
“The resilience you need as an entrepreneur is to go back and try something again is critical,” Fleiss said. “If it were easy, someone else probably would have done it already. The idea for Rent the Runway, I know we weren’t the first people to have that idea. It’s just the hustle, the drive and the persistence…
“The balance of that is being real with yourself also,” Fleiss said. “At some point, you need to give yourself enough markers and milestones to be able to say maybe it is time to do something a little bit different.”
The key, she said, is to hold yourself accountable to a timeline. For Fleiss and her partner, that timeline was determined by their graduation (they were both in Harvard Business School when they developed the idea). They understood that they needed to know if they could raise enough money to pursue this idea before they graduated and turned down more conventional job offers. So they figured out how many investors they had to meet with, how they were going to arrange introductions, and how to contact the right people.
“So putting all of these little minute milestones on a timeline and keeping yourself accountable to that, I think is really important to balance out that persistence,” Fleiss said.