Breakthrough Builders Inclusive Inventor: Jenny Fleiss @ Volition Capital
Jenny Fleiss is co-founder of category creator Rent The Runway, but in some ways, that’s an understatement of the time and energy she put in to revolutionize the designer fashion industry—and forever change old ideas of Who Gets to Wear What.
In her talk with Jesse, Jenny recounts the detailed logistics work and core insights it took to drive growth at Rent The Runway, with lessons learned for aspiring founders. She describes how she now brings her entrepreneurial experience to bear as an investor, emphasizing inclusivity and the growing importance of shared wins. Jenny outlines a format that digital commerce businesses can follow to create personalized experiences at scale. And she offers advice for parents on how to inspire entrepreneurship from an early age. All told, Jenny’s story highlights the transformational power of building in oneself – and others – the confidence to excel.
(3:13) How Jenny’s experience as an entrepreneur led her to join Volition Capital this year
(8:32) Assessing the state of digital commerce—global challenges & innovations
(11:47) Jenny’s POV on the three pillars of personalization-at-scale
(16:56) Launching Rent The Runway with an unprecedented dive into logistics and a crucial market insight
(23:29) How Jenny linked up with RTR co-founder Jenn Hyman, along with her tips for finding co-founders
(29:23) Changing the VC funding landscape and increasing opportunities for women-run businesses
(31:23) Lessons for parents on teaching and encouraging entrepreneurship
Guest Bio
Jenny Fleiss joined Volition Capital in 2021 as the company’s first Venture Partner, where she focuses on next-generation consumer brands. She is an entrepreneur and intrapreneur, founding two scaled digitally native businesses from scratch: Rent the Runway and Jetblack. During her time at Rent the Runway, Jenny wore many different hats, serving as President, Head of Logistics, and Head of Business Development.
Jenny has been honored with numerous recognitions including Inc. Magazine’s “30 Under 30”; Fortune Magazine’s “40 Under 40” and “Most Powerful Women Entrepreneurs”; and Fast Company’s “Most Influential Women in Technology.”
Helpful Links
Fast Company: Inside Rent The Runway’s Secret Dry-Cleaning Empire
Harvard Business Review: Women-Led Startups Received Just 2.3% of VC Funding