What We’ve Learned: A Q&A with Rent the Runway’s Founders

If the startup world had fairy tales, Jennifer (Jenny) Fleiss and Jennifer (Jenn) Hyman would be the main characters. Once upon a time, the Harvard Business School classmates—Fleiss from the finance world and Hyman from sales and marketing—met casually for lunch every week to brainstorm entrepreneurial ventures.

The idea that stuck came over Thanksgiving break, when Hyman’s sister, Becky, wanted something gorgeous to wear to an upcoming wedding, but didn’t want to drop an obscene amount of money on a dress she’d only wear once. From that moment on, Fleiss and Hyman had their concept: Rent the Runway, a “Netflix for dresses” that allowed women to rent designer gowns for a fraction of the retail price.

Now, just over three years later, Fleiss and Hyman oversee the rapidly growing, 125-person, multi-million dollar enterprise with a cultish following of customers who get their own Cinderella experience—a new, gorgeous dress for every special occasion.

We got to chat with the incredible duo to hear more about how they turned an “I have nothing to wear” dilemma into an opportunity that looks like it’s headed for happily ever after. Read on for the story of how they got started, and the advice they’d give to every aspiring entrepreneur .

Why was Rent the Runway the right idea—and what made you move forward with it?

JH: Actually, I never said, “oh this is a brilliant idea, this is going to be a billion dollar company, we have to do this.” My reaction was: I had an idea, I thought it was interesting, Jenny thought it was interesting, we thought it was fun, and we thought, let’s figure out if this is a great idea.

JF: When Jenn came to me with this idea, we decided to do it as a course credit. But we also decided to spend the rest of the year figuring out if this was something we could do full time, instead of getting a job. We gave ourselves a fixed deadline—by the time we graduated, we’d see if this would actually work. And if it didn’t, we had other jobs that we were going to accept.