5 Ways Entrepreneurs Can Stay Scrappy

#PEIntensive17, Advice, female founders, startups

Jenny Fleiss, Co-Founder of Rent the Runway and CEO and Co-Founder of Code Eight, discusses the early days of Rent the Runway and shares her insights on the ways entrepreneurs can stay scrappy as they build their businesses during a session at the Project Entrepreneur 2017 Intensive.

1. Take full advantage of the here and now.

Fleiss believes entrepreneurs can stay scrappy by paying attention to the world around them and taking full advantage of the here and now. She credits a conversation with Rent the Runway Co-Founder Jenn Hyman’s sister as the “aha” moment for developing the Rent the Runway model. Hyman had just returned from visiting her sister, who had spent thousands of dollars on an expensive gown for a wedding.

When Hyman pressed her sister on why she bought the dress, Fleiss recalls that Hyman’s sister said two things that “were pretty funny, but [also] spoke to real changes that were going on in our world.” Hyman’s sister said all the dresses in her closet were “dead to her” because she’d been photographed in them, and the photos had been shared on social media. “The idea that you could wear [a dress] and that moment it was posted across social media, that you couldn’t ‘cheat’ and wear the same outfit again tomorrow, was a really new thing.”

The other thing Hyman’s sister said: she could meet her future husband in the dress she’d bought. “Again, a funny statement, but again the idea that a woman in her twenties is at the lowest income earning point in her life, but has these ‘high-stakes’ events, there’s this disparity. There’s a millennial consumer who has this need, and it’s not being serviced, which led us to get going.”

Fleiss and Hyman realized that there were things happening in the world around them in 2008—particularly the explosion of social media and the new possibility of the internet—that made renting dresses a viable solution to problems the female millennial consumer was currently facing. “These were scrappy realizations.”

2. Listen to your customers.

Fleiss stresses how important listening to customers has been for Rent the Runway since the beginning. When she and Jenn Hyman first started Rent the Runway at Harvard Business School, they were sure to test their concept on some of the undergraduate campuses. “The story we always tell is that this one girl picked a gold sequined dress, tried it on, twirled in the mirror, and said, ‘I look hot.’ That was really the turning point for our business where we realized this is not about cost or convenience, or what designer you’re wearing, but it’s that feeling you get when you put yourself together.”

By listening to how their customers responded to the model and the products, Fleiss and Hyman built their company around the mission of bringing confidence to women. As much as they believed fashion could help them do that, Fleiss and Hyman knew that they wanted to share other tools and resources with their customers, and listening to what their customers wanted helped Fleiss and Hyman decide what those other tools should be.

“We had the idea to start a foundation in the really early days…but one thing I’ll say is our customers helped us get to this point too. When we did focus groups, we kept hearing from customers that there was this real entrepreneurial DNA in our brand; they already associated our brand with entrepreneurship, and many of our customers were entrepreneurs or aspiring entrepreneurs…so we decided to leverage that and go after this dream we’d always had of starting [Rent the Runway Foundation].”

3. Do-It-Yourself if you can, but know where and when to invest in your brand.

In the early days of Rent the Runway, Fleiss recalls needing to be pretty scrappy in order to test such a new and disruptive model. “We did these customer tests where we…each spent a couple thousand dollars of our own money…and then we set up shop [to] see what brands people want, what styles people want, what type of consumers like this, do [they] need to try the dresses on or not, do [they] need to see them in person. Through those trials we learned so much.”

But Fleiss and Hyman, while willing to DIY some parts of their business in the beginning, were also thoughtful about where they invested in their business, whether through outsourcing work or hiring in-house teams to tackle certain aspects of the business, such as the website. “Creating a special experience around Rent the Runway so that designers could trust us with their brands was also crucial, and that became apparent right away. Spending time, money [and] resources on the design and the interface of the website [and] our packaging [was important].”

4. Pivot quickly.

Scrappy entrepreneurs pivot quickly when they realize their model either isn’t working or isn’t what customers or clients want. Fleiss and Hyman realized they had to tweak some aspects of their initial model after meeting with industry giant Diane von Furstenberg. “We found some DVF dresses, got our hair blown out, drove from Boston to New York…and she spent an hour-and-a-half telling us how she hated our concept, which was also a quick introduction to entrepreneurship and something I am sure every single person will face.”

Fleiss recalls using the conversation with von Furstenberg to develop an improved idea for Rent the Runway. “Being able to listen to this pivotal person and think about how we could shape our pitch going forward and our concept going forward to appeal to designers was really powerful.”

5. Embrace naïveté.

When asked what she knows now, as the co-founder of a profitable company, that she wished she knew when she was just starting out, Fleiss is clear that she wouldn’t change anything. “Probably nothing, in the sense that I think the biggest gift of entrepreneurship is being naive, and I truly mean that. You can’t possibly know all the challenges that lie ahead, and if you did, you probably wouldn’t be crazy enough to start.”

Founders that accept and embrace naïveté as they start their businesses are probably more scrappy simply because they don’t know any better. “I never expected we would have to build the world’s largest dry cleaner, or a fully automated warehouse facility that’s 300,000 square feet and all of the technology to power that facility. We didn’t even think about the fact that we would need to run a photoshoot to have photos for our website until two weeks before we had to launch,” says Fleiss. “We did not come from the fashion or tech industries. Had we known…how ballsy what we were doing was, I don’t know that we would have done it.”


Fleiss’ advice comes from her #PEIntensive17 conversation, “Starting Scrappy,” with Cheddar TV anchor Kori Hale. Listen to the entire conversation on episode 37 of our podcast and subscribe on iTunes, Google Play or SoundCloud.