19 Jenny Fleiss: Co-founder of Rent the Runway and Jetblack

Learning from Failure

Jenny Fleiss, co-founder of Rent the Runway, shares insights on learning from failure and adapting business strategies. She recounts an early rejection from fashion icon Diane von Furstenberg, who initially disliked their concept due to fears of cannibalizing sales. However, Jenny and her team used this feedback to refine their business model, demonstrating that renting could introduce younger consumers to high-end brands, eventually converting them into buyers 1. This experience highlights the importance of resilience and adaptation in entrepreneurship 2. Jenny emphasizes, "Entrepreneurship is like highs and lows, and I think it's like flying a plane at low altitude."

   

Adapting Models

Adapting business models to meet market needs is crucial, as Jenny Fleiss explains through her journey with Rent the Runway. Initially targeting Harvard students, they tested their concept by renting dresses to different groups, learning from each iteration about customer preferences and operational challenges 3. This iterative process allowed them to refine their offerings and better understand their market 4. Jenny notes the emotional impact of their service, saying, "Consumers were emotionally changed when they put on a great dress."

   

Startup Challenges

Navigating startup challenges requires strategic planning and bold decisions. Jenny Fleiss discusses the critical decision to raise venture capital for Rent the Runway, understanding that significant investment was necessary to scale the business 5. She and her co-founder set a timeline to secure funding, which they successfully achieved, allowing them to fully commit to their startup vision. Jenny reflects on their early days, "We wound up buying dresses and we bought them in our own sizes. We're like, if this doesn't work, we're going to have a great wardrobe" 6.