Jenny Fleiss

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Partner at Initialized Capital & Co-Founder, Rent the Runway and Jetblack

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Jenny Fleiss: Biography at a Glance

  • Jenny Fleiss is the Co-Founder and Board Member of Rent the Runway, an 11 million-member startup that pioneered dynamic ownership in the fashion industry by enabling women to rent designer clothing. 
  • Rent the Runway, one of only 20 female-led "unicorn" companies in the U.S. to achieve a $1B valuation, went public.
  • Jenny is currently a partner at Initialized Capital doing seed stage investing with a focus on e-commerce enablement, consumer and AI.
  • She is also the Co-Founder of Jetblack, the first start-up in Walmart's tech incubator, which reshaped the way consumers shop through one-to-one, highly personalized experiences.
  • Jenny is a board member of The Lanvin Group (LANV), Shutterfly, and Yale Ventures and is an adviser to and investor in various businesses, many with female founders.  
  • She was named one of 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."
  • Jenny uses her career experience to speak to business trends as well as entrepreneurship, intrapreneurship, AI and Machine Learning.



Jenny Fleiss is a Partner at Initialized Capital focused on seed stage investing with a focus on e-commerce enablement, consumer and AI. Jenny is an entrepreneur and intrapreneur, founding two scaled digitally native business from scratch: Rent the Runway and Jetblack. Jetblack is the first portfolio company within Walmart’s technology incubator, disrupting traditional e-commerce with a personal shopping service over text message and voice. Previously, Jenny Co-Founded Rent the Runway, a business that has transformed the retail industry by making designer clothing rentals a convenient and accessible luxury experience for millions of women. Jenny is on the board of Rent the Runway (RENT), The Lanvin Group (LANV), Shutterfly, and Yale Ventures and is an adviser to and investor in various businesses, many with female founders.  

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.” 

She earned her MBA from Harvard Business School and graduated Cum Laude from Yale University. She currently resides in New York City with her husband and three children.


The Power of Data – Insights from Rent the Runway and Jetblackarrow-down

Data has been at the core of building both Rent the Runway and Jetblack. In this talk, Jenny reveals her playbook that businesses of all sizes can apply to ignite their growth.

At Rent the Runway, building an analytics team out of the gate was critical to their explosive success. It opened an ecosystem of intellectual property, from inventory selection to optimal garment cleaning methods. Deep data built for AI powered Jetblack’s conversational commerce platform, enabling Jenny's team to understand key product considerations and consumer attributes, while optimizing one-to-one personalized product recommendations.

But quantitative data is just one part of the equation. The voice of the customer has become even more important amidst the increasingly formulaic and technical landscape. Jenny shows how to effectively inject qualitative data throughout the lifecycle of a company to illuminate unmet consumer needs, innovative behaviors, and fresh business opportunities. For Rent the Runway, this inspired tangible examples like real consumer photo reviews, retail stores, and a massive new revenue stream through subscriptions.

From surveys and focus groups - which can be done at the earliest stages of a company with little resources - to cohort and pricing analyses for conversion optimization, Jenny delivers an actionable plan that will empower audience members to truly understand what drives the growth and profitability of their businesses.

Entrepreneurship – The Story of Rent the Runwayarrow-down

How did Rent the Runway go from a simple idea to a $1 billion unicorn company that is disrupting an entire industry? The story of Rent the Runway is packed with teaching moments that every entrepreneur can apply to accelerate the growth of their own business. Jenny takes audiences through her entrepreneurial journey, breaking down exactly how to uncover valuable customer insights, tap into the world’s most powerful marketing strategies, create magnetic customer loyalty, and build a disruptive brand from the ground up.

Intrapreneurship – How Innovative Companies are Transforming from the Inside-Outarrow-down

As new technologies disrupt industries faster than ever, driving change from within is critical to success. Having led Walmart’s first tech incubator, Jenny created a template for innovation within the world's largest retailer. She reveals how entrepreneurial principles can be used by businesses of all kinds to grow revenue, drive innovation, and transform themselves into unstoppable forces.

Machine Learning & AI – Why Successful Businesses Find Balance Between Humans and Techarrow-down

Our world has been transformed by tech-driven solutions that promise efficiency and hyper-personalization. But as technology becomes embedded into every aspect of our lives, the feeling of human touch takes on the critical role of establishing trust and comfort with consumers. How do successful companies balance AI with a humanized experience to create customer loyalty? Drawing from her experience leading Jetblack to harness the power of machine learning and conversational commerce, Jenny shares her roadmap to the ultimate hybrid experience.

Blend, Not Balance – Dream Boldly by Embracing Work & Lifearrow-down

Many women approach their career ambitions timidly. Many even hesitate to address the infamous question of “balance” in work/life. The weight of this question leads to less risk-taking, more apprehensive planning, and smaller goals. 

Work and life are a BLEND, not a balance. Balance implies a choice — weighing two different things against one another. Jenny Fleiss built two companies, including Rent the Runway, and faced the balance question across different life stages as a young woman and a working mom.

Jenny shows audiences that the multitasking inherent in managing personal life, a household, and a family should be celebrated. Forced creative problem-solving will make you a better business leader, having children can make you better at time and stress management, and embracing the blend of our lives offers a striking perspective on just how far you can go.

Even in the lowest moments of your career or the entrepreneurial roller coaster, Jenny shows that by boldly embracing the blend — you can live without fear of dreaming bigger and going after it.


Jenny was wonderful on stage and we appreciate her coming to the estate dinner. We’ve been so thrilled by the event and everything has gone smoothly!


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