Yale School of Management

Rent the Runway’s Jennifer Fleiss on Harnessing Your Entrepreneurial Energy

October 30, 2015

Jennifer Fleiss YC ’05, co-founder of and head of business development for Rent the Runway, spoke at the first event co-hosted by the Women in Management and Entrepreneurship Clubs at Yale School of Management on October 15. Fleiss discussed the process of bringing the women’s online apparel company from the ideation phase to fruition in 2008 and the challenges of scaling a business that now has more than 5 million subscribers and is growing 50% year over year.

Fleiss said that one of the most important lessons she’s learned as her company has grown is how to direct her entrepreneurial energy in ways that will directly benefit her business:

As an entrepreneur, I’m still thinking of five different, new ideas a day—that’s just being an entrepreneur. Once you start your company that still happens, and it’s great, but you just need to find ways to harness it and to pick how you’re going to expand. You need to develop this rigor so you grow.

It’s not that you should stop iterating, because you always want to be iterating; you always want to be serving your customer—but you want to pick your battles and pick which path you’re going to go down. You have to be really thoughtful and strategic about what you’re going after next, what that progression is going to be.

Start being better about saying no to things. Entrepreneurs typically have this “yes, yes, I can do it all” personality, and as your company gets bigger you’ll start to get opportunities that sound awesome, but if they don’t fit in line with the plan you’ve crafted, sometimes they’re not worth spending your time on. 

From left: Laura Fletcher ’16 of the Women in Management Club, Kevin Elliott ’16 of the Entrepreneurship Club, and Jennifer Fleiss

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Meredith Crawford

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