Jennifer Fleiss

Why buy a $5,000 dress when you can rent it for $50?

In 2008, Jennifer Fleiss had a radical idea: what if, instead of buying a designer dress for thousands, you could rent it for a fraction of the price.

The fashion elite scoffed.

Would women really wear secondhand couture?

Yes, and in record numbers.

Jennifer and her co-founder Jennifer Hyman launched Rent the Runway from a tiny office, running dress rentals like a logistics startup instead of a fashion brand.

By 2019, it became one of the few female-led unicorns with a $1B valuation.

But Jennifer wasn’t done shaking up retail.

In 2017, she co-founded Jetblack, Walmart’s text-based AI shopping service… predicting the future of concierge commerce before it was mainstream.

The idea? Personalized, on-demand shopping where customers could text a request and get anything delivered, from birthday gifts to groceries.

It was ultra-premium, ultra-fast, and unlike anything in retail at the time.

Today, as a partner at Volition Capital, she’s backing the next wave of disruptive startups, many led by women.