From Yale to launching a fashion revolution, Jennifer Fleiss ’05 is transforming how consumers experience clothing and sustainability.

By Michelle Cheon, Yale College '28

Sixteen years ago, Jennifer Fleiss ’05 redefined fashion accessibility. As an undergraduate at Yale, she majored in political science but quickly developed a passion for entrepreneurship and innovation. After earning her MBA at Harvard, she co-founded Rent the Runway—a company built on the idea that shoppers should be able to access designer clothing without the cost or waste of ownership. By pioneering the clothing rental model, Rent the Runway reshaped consumer behavior and introduced circularity into an industry long known for excess.

Under Fleiss’s leadership, the company became a household name, earning widespread recognition for its impact on sustainability and women’s empowerment. After scaling Rent the Runway to unicorn status, she went on to co-found Jetblack, Walmart’s first text-based personal shopping service, and has continued to champion female founders and early-stage innovation as an advisor and investor.

We asked Jennifer five questions about her journey from Yale to entrepreneurship, the lessons she’s learned while building industry-changing startups, and what’s next in her mission to make commerce smarter and more sustainable.

What originally inspired you to start Rent the Runway, and how did that initial vision evolve into the company it is today?

The spark came from my co-founder’s sister, Becky, who bought an expensive dress for a wedding she was attending. What seemed like a frivolous decision actually reflected something deeper — the desire to show up as her best self. Social media was just taking off, and she joked, “I might meet my future husband at this wedding!” That combination of self-expression and high stakes resonated with us. When we spoke to dozens of women, many echoed the “Facebook kills outfits” sentiment. We saw an opportunity: technology could power a shared closet that democratized access to designer fashion, letting women enjoy the real thing — sustainably and affordably.

Over time, our vision expanded from renting special-occasion dresses to creating a subscription model for everyday wardrobes. Rent the Runway evolved into a platform that completely reimagined how women engage with fashion — turning ownership into access.

Looking back, what early experiences most shaped your entrepreneurial mindset
and approach to building something new?

At Yale, I learned to approach challenges with curiosity and creativity — to see constraints as sparks for innovation. I built my class schedule around what genuinely excited me and was constantly inspired by the diversity of ideas across campus. One class that stands out was Creativity and New Product Development. I originally took it to fulfill a Category IV requirement but ended up discovering the power of play and experimentation at work. It showed me the magic of “learning by doing.” I even started drafting a patent over spring break — a moment that made entrepreneurship feel both tangible and thrilling.

What do you wish you’d known when you were first starting out?

That not knowing everything is actually an advantage. We had zero experience in fashion, tech, or logistics, and that forced us to question everything.

Early on, we outsourced too much technical work and quickly realized that anything core to your business needs to live in-house. You don’t have to code, but you do have to understand the heartbeat of what makes your company run.

And above all: momentum matters. Even imperfect progress beats perfection that never ships. Startups are emotional rollercoasters—resilience is your seatbelt.

You’ve supported Yale’s innovation ecosystem through speaking and mentorship. Why is it important for you to help the next generation of founders?

I believe deeply in the compounding effect of shared knowledge. When I started, there were few visible female founders—and representation matters. Mentorship is how I pay forward the advice and encouragement that helped me take bold steps.

Plus it's energizing. Everytime I meet a student with a fresh idea, it reminds me of the early Rent the Runway days when anything felt possible (and usually was, with enough hustle and caffeine).

With AI and personalization transforming retail, what trends in consumer technology excite you most right now?

I love what’s happening at the intersection of AI, content, and commerce, where recommendations meet storytelling. The next generation of retail is going to feel a lot more like your favorite creator knowing exactly what you love.

From AI-assisted styling to shoppable content and community-driven platforms, we’re heading into a world where inspiration and transaction merge. Shopping will feel more personal—and a lot more fun.