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Entrepreneurship 101: The Ladies of Rent the Runway

We're thrilled to present this smart LearnVest story here on Savvy!

Wondering if you could turn your macramé skills into a money-making biz? Looking for tips on how to sustain and grow your business? Dreaming of a time you can stop answering to others and be your own boss?

We hear you. In our monthly  Entrepreneurship 101 series, we ask female entrepreneurs what it takes to run their own businesses, so you can learn from their mistakes and successes.

Jenn Hyman and Jenny Fleiss are the founders of Rent The Runway, a website that lets you rent designer dresses for a fraction of their cost. (We’ve recommended it for wedding season, along with other money-saving tips.) They realized that many women have a closet full of clothes but still find themselves without the perfect dress for a special event. So, they took on the macho world of venture capital, convincing a room full of men they had what it takes to run a successful company.


We talked with Fleiss and Hyman about their adventures in retail, how they found the confidence to pitch their idea and what skill they think every woman should have.

Tell me about your decision to leave your full-time job.

Jenny Fleiss: I was working in finance, and it wasn’t an industry I was really passionate about. It was good for my resume, but I knew deep down it wasn’t the best use of my skills. Deciding to leave was a little bit about getting up the courage, but it was also about putting a marker down and saying, “If I don’t make a decision by this time . . . ”

Were you really interested in fashion before starting RTR?

Jenn Hyman: I always loved fashion–I grew up as a shopaholic. I see shopping as a way to explore a new city and get a grasp on the culture. Women express their emotions through what they buy and wear.

Jenny Fleiss: I grew up on 59th Street in New York, surrounded by department stores. I used to view fashion as functional. I’m a great test case: Rent The Runway enabled me to experiment, and now I love fashion.

Read on for to hear what advice the RTR ladies have for women who want to start their own thing.

How would you advise women who want to start a business but don’t have the business experience you two had?

Jenn Hyman: Everyone needs to assess the skill sets needed for the business, and if they don’t have skills, figure out how to bring on partners with complementary skill sets. I came from sales and marketing; Jenny came from a finance background. When we were building the team, we always asked ourselves what the new person we were hiring was adding. If you don’t have specific experience, find those key people before trying to raise funding.

Putting together the team is the best part of business, but also the most challenging. We’re always looking for new talent.

What piece of advice would you give to women presenting to male-dominated venture capital firms?

Jenn Hyman: Know your audience. When we were pitching RTR, we were meeting older men, and we had to adapt presentations to them.

Jenny Fleiss: My piece of advice: Think about their decision-making process. They want to see how quickly an entrepreneur can eliminate risk. Will women rent dresses? Will they return them in good condition? Will designers work with us? We had to answer all these questions and show them how we’d eliminate the risk.

Jenn Hyman: You have to have confidence–women struggle with this. We were launching a new and different idea, so we heard a lot of nos before we heard any yeses. When you hear “No,” you have to listen to why it’s a no, change direction, but remain confident that your underlying business idea is sound.

Did you do any testing before you launched the business?

Jenny Fleiss: For most businesses that are consumer-facing, you can test. You want to answer specific questions one test at a time. Will they rent the dresses? Will they ruin them? How do we ship them?

Jenny Fleiss: We learned the most from sales associates in stores or people who were entry-level working for designers. It wasn’t just meeting with CEOs. Great ideas come from everywhere.

What did you learn from sales associates?

Jenny Fleiss: We learned that women never bring just one style into the dressing room–they bring multiple sizes and styles. So we realized we needed to replicate the dressing room experience. That’s why we allow women to rent a second style for $25. It’s fundamental to getting women to try new brands. I learned that from a 23-year-old on the floor.

How do you two share responsibilities?

Jenny Fleiss: We have great complementary skill sets. Jenn is great at rallying around ideas. I play a role in execution. Jenn spends time with customer-facing issues; I spend time on the back end.

Looking back, what do you wish you knew before starting?

Jenny Fleiss: Many things! I wish I had a technology background going into it. Business schools, colleges and high schools should teach women about technology.

Jenn Hyman: I agree with Jenny: I will be on a mission to change the education system and to teach people computer science earlier. I wish I had had more experience online. To come into this industry without that knowledge was a handicap. Lots of people have ideas, but few turn them into successful businesses. What does it take?

Jenn Hyman: You have to have confidence in the concept. Having a co-founder has been helpful, because it’s having a cheerleader by your side. Also, you need to derive ideas from a team and from other people.

Jenny Fleiss: Execute–stop talking about it and just do it. If you talk about it for another month, you still may not get it right. There are no mistakes–only opportunities. Be scrappy, and don’t let anything be an obstacle or an excuse.

Image Source: Getty
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