Rent the Runway Co-Founder Jenny Fleiss Goes On The Road

AN INTERVIEW WITH JENNY FLEISS ABOUT HER LIFE IN CARS

Jenny Fleiss has changed the way women think about clothes. In 2009 she co-founded Rent the Runway with Jenn Hyman. The founders’ premise was to give women the option to rent designer clothing, rather than maxing out their credit card for a one-time wear. A decade ago, the shared economy was just beginning, and Rent the Runway was among the defining companies to change the way consumers looked at buying, owning, wearing, and using material items. Why buy when you could rent as a more sustainable option? 

At the time the two founders were still Harvard grad students. Fast forward to the 2009 launch, when a lead story on The New York Times drove 100,000 users to sign up for Rent the Runway on day one. The rest is retail business history, and the company has been valued at $1billion. 

Fleiss stepped down from Rent the Runway in 2017, but continues to serve on the board. She moved on to be CEO of Jetblack, the first portfolio company as part of Walmart’s foray into tech incubators that used text and voice messages for personal shopping.  When Le Car spoke with Fleiss she was riding out the pandemic with her husband and three children outside of New York, where driving had become her favorite past time.

How were cars a part of your growing up experience?

I grew up in Manhattan, but we drove to Long Island each weekend, so our family car was always part of the picture. We always named our cars and I remember one that talked and we named him Gordon. My parents kept an old Opal from my mom’s childhood named Gwynlelyn that always broke down. We had a large, wood paneled station wagon with seats that popped up in back to face one another so we could play board games during the drive!  Cars were always a fun part of the journey.

What is your preferred method of getting around town?

We have a Land Rover Discovery and actually like driving it around Manhattan, given we have 3 kids it’s often easiest to just pull the car out to get them around to their activities.  

Tell us about something memorable that happened to you in a car as an adult driver or passenger.

What immediately comes to mind are kids getting sick in the car. Yuck! But I also (as a quasi-adult) remember failing my driving test three times before passing. Yikes!

Do you own a car and what do you think of it? If you don’t, why not?

Yes. I don’t like the way the exterior looks, but I like the way it drives and it’s a good comfortable car for the family without having to fully cave to a minivan.

Do you think we should give up our cars? Why/why not?

Totally depends where you live.  I love creative options like Citibike or even just walking around the city to reduce pollution, but in some instances, cars are harder to live without.

What is your dream car?

I’ve recently been wanting the Tesla! Mostly really intrigued by it and electric cars.

What is your dream destination?

The California coast.

What is your favorite road?

Dune Road in the Hamptons or the Amalfi Coast. 

What is the best color for a car exterior and interior?

White or navy outside, tan interior 

When you are driving or riding or flying what do you listen to?

Podcasts or audio books.

Do you see yourself in an electric vehicle some day? Why or why not?

Yes, would love to try it — eco-friendly and lots of fun tech in them.

Finally, when we can all move freely again, where do you want to go?

Crazy thing is I am trouble thinking of anywhere I’d rather be than with my family, as I am right now!  We were supposed to go on a family trip to Israel this summer and it would be amazing if we could still make that happen, but I’m also happy to stay put.