How Jenny Fleiss built Rent The Runway | The Further, Faster Podcast

What does it take to build a revolutionary fashion start up? More importantly, what does it take to build, raise and grow a business centred around the lifestyle demands of younger women, when most investors are still middle-aged men? 

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When Jenny started pitching Rent the Runway, she was knocked back countless times. She discusses the process of “reframing objections as needs” – a vital skill for any founder. Designers were anxious that a rental service would “cannibalise sales” so Jenny switched the pitch to remind them that it’s not rentals they need to be afraid of: but fast fashion. Taking the idea into boardrooms was tough too. Men in their 60s? “Not our core customer”. Again, Jenny shares how she developed strategies to encourage investors to connect with their product. 

The success of Rent the Runway is rooted in the deep affinity Jenny has for her customer base – solving a pain point that she and her co-founder Jennifer Hyman authentically felt. She discusses what it means to create an amazing customer experience, and why it is so important to raise the bar for “magical moments,” from a website, to packaging to communication. 

Speaking from her perspective as an investor, Jenny still looks for founders with a “natural” obsessiveness about how their customer feels. Of course, grit and determination is also a must. “You need people who are ready to fight through a lot of obstacles and hurdles,” she says. “That even if 10 doors are slammed in your face, believe that 11th door could lead to an opportunity.”

For more insights on everything from raising capital to holding yourself accountable, listen to the full podcast episode here.