Leading the retail industry transformation

If you’ve been paying attention to the news, you’ve probably heard a lot about the economy. Just as no one can predict with complete accuracy when a recession will hit, no one can predict exactly when the economy will recover. While over time the economy does follow certain patterns, right now it feels unpredictable and extremely uncertain.

For most people, an uncertain economic environment creates a feeling of fear. You might be fearful about your company going out of business, or laying people off. If you’re just entering the workforce, you may be afraid you won’t be able to find a job. Or, perhaps you’re scared of the hit your portfolio will take – that your retirement savings won’t be enough for the lifestyle you want. And if you’re a business owner, you may worry that your business won’t survive a recession.

Regardless of your situation, a challenging economic environment requires one thing: innovation. In both good times and bad, innovation is a critical piece to moving forward. And what many people don’t realize is that recessionary environments have yielded some of the most innovative companies of our time, like FedEx, Airbnb, Disney and Microsoft.

You’re about to hear from an entrepreneur who started her business right smack in the middle of a downturn. Jenny Fleiss created Rent the Runway, a company now valued at $1 billion, in the wake of a severe economic recession. When everyone else was panicking in 2008 and 2009, Jenny and cofounder Jennifer Hyman saw that a retail industry transformation was happening – and they saw an opportunity. In this episode, Jenny shares how she and her cofounder got Rent the Runway up and running, then grew the business to where it is today.

Who is Jenny Fleiss?

Jenny Fleiss is an entrepreneur, business owner, venture fund partner and mother of three. She’s certainly busy, and that’s exactly the way she likes it. Jenny started Rent the Runway right out of college, setting up a pop-up shop and eventually evolving the business to what it is today: an online service that allows women to rent designer clothing, online, for a fraction of what it actually costs.

Jenny has won every award you can think of: Top 30 under 30, Top 40 under 40, Forbes Entrepreneur of the Year and more. Yet eventually, she made the choice to step away from a company valued at $600 million. Why? She says, “I have always been a serial entrepreneur at heart … I missed that startup stage. I was ready for the next adventure.”

Jenny left Rent the Runway in 2017 to start up Jetblack, a personal shopping service that was part of Walmart’s first-ever technology incubator, Store #8.