Jennifer Hyman didn’t set out to disrupt fashion.
She noticed one uncomfortable truth at a Thanksgiving table and refused to ignore it.
That moment led to Rent the Runway and quietly changed how millions of women think about access, ownership, and identity.
In this issue, I break down Jennifer’s founder story and what made it work, including:
3 lessons founders can borrow from how Hyman sold belief before product
A Fun Fact on the surprising math behind shared closets and brand discovery
A Video showing how Jennifer connects her personal story to building a public company
Enjoy this look at how emotions and data scale a brand…LG
Founder Story: Jennifer Hyman, Rent the Runway
Jennifer Hyman's first job out of college was at WeddingChannel.com, running an online advertising sales team. She watched how deadlines compressed decisions, how emotion accelerated spending, and how special-occasion purchases followed different rules.
She discovered people were less price-sensitive and more focused on how the moment made them feel.
Next, she joined Starwood Hotels, where at just 22, she pitched and helped build the company's first wedding business, including concepts like honeymoon registries that let guests contribute to experiences instead of objects.
When she first pitched the Starwood president, the response was cautious. Not a no, but not a yes. That experience taught her how ideas actually move through institutions. Progress did not come from authority. It came from influence.
After Starwood, Jennifer joined IMG's luxury fashion division. Inside the fashion ecosystem, she saw how designers thought about brand equity and scarcity, and how deeply they feared counterfeits and discounting. Fashion, she learned, was not just a product. It was perception.
By the time she left IMG, Jennifer had absorbed a rare mix: e-commerce, hospitality, luxury fashion, and emotional commerce.
FROM OWNERSHIP TO SHARING
Thinking about what to do next, Jennifer enrolled at Harvard Business School. At HBS, she watched how technology was reshaping access. Music streaming. Car sharing. On-demand media. Ownership was quietly losing its hold.
That fall, Jennifer flew home for Thanksgiving. At the family table, her younger sister Becky admitted something that stopped the conversation. She'd just spent over $600 on a designer dress for an upcoming wedding.
Not because she loved it, but because nothing in her closet felt usable. Everything had already been photographed on Facebook.
"My closet's dead to me," she said. "I've been photographed. I need to wear something new."
That sentence crystallized something Jennifer had been observing. Social media had turned closets into public archives. Repeating outfits was simply not acceptable for special events.
The purchase wasn't about fabric. It was about buying the feeling of walking into a room as the best version of yourself under constant visibility.
Jennifer didn't lecture her sister. She zoomed out. She saw a generation of women trapped between aspiration and affordability. A question formed: what if you could get the experience without the ownership?
Around the same time, Jennifer connected with another HBS student, Jennifer (Jenny) Fleiss. They noticed the same shifts. People were renting cars through Zipcar, streaming music on Spotify, watching movies without owning DVDs on Netflix. Meanwhile, celebrity culture and aspirational branding were intensifying online.
Why couldn't the logic of access apply to fashion?
Within weeks, they sketched the core concept: rent designer dresses, wear them, return them, move on without the burden of ownership. It was simple. And radical.
THE DORM ROOM TEST
Rent the Runway made designer clothes accessible
Rather than immediately building technology, Jennifer and Jenny applied what they called a "Smart-Lazy" approach. Do the minimum work required to validate demand.
They bought around a hundred dresses, then staged trunk shows in Harvard dorm common rooms. They invited sorority members, student leaders, and curious investors. Then they watched.
The reaction was immediate. Women lit up when they tried on dresses they could never afford to own. They stood taller. Took risks with color and silhouette. Some even cried. The experience wasn't transactional, it was transformational.
Jennifer paid equal attention to what happened after. Returns. Damage. Cleaning. Even at a tiny scale, the complexity was obvious. Instead of being discouraged, Jennifer leaned in. If this was hard, it would be hard to copy.
DIANE VON FURSTENBERG
With validation from the dorm tests, Jennifer and Jenny knew they needed real designer inventory. They cold-emailed Diane von Furstenberg. Against all odds, they got a meeting.
DVF arrived skeptical, worried about brand dilution. Jennifer reframed the entire pitch. Rent the Runway wasn't targeting DVF's existing customers. It was for younger women who couldn't yet afford her dresses but aspired to wear them. It was customer acquisition, not cannibalization.
Jennifer showed her the data from the dorm tests. She showed her the tears, the joy, the transformations. DVF saw something she hadn't expected: rental could build brand loyalty with the next generation.
They walked out with a handshake deal. If Diane von Furstenberg was in, other designers would follow.
FUNDRAISING
Fundraising was brutal. Two women in business school pitching a dress rental startup during a recession to older male investors. Many couldn't relate. Why would women rent used dresses? What about hygiene?
To combat the objections, Jennifer relied on storytelling and data. She told Becky's story. She used lived experience to bridge empathy gaps. She brought data from the dorm tests and showed them the unit economics.
When the first term sheet arrived from Bain Capital Ventures, it came with a 24-hour exploding clause. Sign now or lose the deal. The lead investor, Scott Friend, paid attention not just to the idea but to how they worked. The testing. The scrappiness. The customer obsession.
They signed.
WINNING OVER DESIGNERS
With DVF on board and funding secured, Jennifer and Jenny began convincing other luxury brands.
Most reacted with fear and anger. One high-end executive literally screamed at Jennifer over the phone:
"Hell will burn over before I work with Rent the Runway."
How’s that for feedback on your idea?
Jennifer stayed polite, but kept moving.
She used the same reframe with every designer. This isn't about your core customer. This is about introducing your brand to women who will buy from you in five or ten years when their income grows.
She backed it up with data showing that 98% of customers were renting brands they'd never purchased before.
Slowly, designers began to see rental not as a threat, but as a marketing channel.
LAUNCHING A LOGISTICS MACHINE
In November 2009, Rent the Runway officially launched. The early days were scrappy. Jennifer and Jenny handled logistics, customer service, and packaging themselves, personally inspecting every dress that went out and came back.
Every detail mattered. Dresses had to arrive smelling fresh, looking pristine, and feeling luxurious. They weren't renting cars. They were renting confidence.
Customer feedback shaped everything. When dresses arrived wrinkled, they invested in better garment bags. When women worried about fit, they added backup sizes at no extra cost. When return logistics felt complicated, they included prepaid labels.
Behind the scenes, Rent the Runway became an operational beast.
They built what would become the largest dry-cleaning operation in the U.S. by pounds processed per hour. Every garment was tracked through roughly 40 data points: fabric type, construction quality, wear patterns, damage history.
Each dress was designed to be rented roughly 30 times. About half returned with stains requiring hand treatment. The hardest roles to hire weren't engineers or marketers. They were expert "spotters" who could identify fabric types instantly and treat stains without damaging delicate materials.
Over the next 6-years, over 80 competitors tried to copy the model. Most failed. The technology was copyable. The logistics were not.
SHIFTING TO SUBSCRIPTION
Seven years after launch, Rent the Runway surpassed $100 million in revenue and achieved profitability.
That same year, it raised a $60 million, then the largest funding round for a woman-led startup.
Jennifer saw a deeper opportunity. Women weren't just managing special-occasion wardrobes. They were managing everyday identity.
What if they could rent not just for weddings, but for work, dinners, and weekend events?
The subscription model, Unlimited, launched that year. Members could rent multiple items per month and swap them as often as they wanted. By the next year, subscriptions accounted for roughly 75% of revenue. The closet became dynamic.
THE COVID CRASH
Then COVID-19 hit, and demand collapsed overnight. Events vanished. Offices closed. Nobody needed a rotating wardrobe when they weren't leaving the house.
Jennifer laid off half the staff, simplified operations, renegotiated contracts, and focused on survival. It was the hardest period of her career. But she used it to strip away complexity and double down on what truly mattered: the subscription model and customer experience.
When the world reopened, demand didn't just return; it accelerated.
Women who'd been stuck in sweatpants for months wanted variety more than ever.
The subscription model that let them refresh their wardrobes constantly became more valuable, not less.
Today, Rent the Runway generates over $300 million in annual revenue and serves roughly 150,000 active subscribers. It operates not as a novelty, but as an infrastructure for how fashion circulates.
Storytelling Lessons:
Jennifer’s story illustrates how leading with empathy, reframing, and proof is a powerful combination to persuade investors, designers, or customers by explaining your value proposition. She changed how they saw the problem, then backed that shift with evidence. Here are 3 lessons you can apply directly to your own story creation and communication.
Reframe the Objection Into the Opportunity
She reframed designers fears by explaining how Rent the Runway was a discovery engine for new customers introducing younger women to the brand long before they could afford it. What looked like cannibalization became customer acquisition. Turning their fear into an opportunity.
ACTION: Identify the objection you hear most often. Write it exactly as your audience says it. Then ask how that fear could actually be the advantage. Rewrite your story so the objection becomes the proof point.
Use a Personal Moment to Create Instant Empathy
Hyman told the Thanksgiving story about her sister Becky and the line, “My closet’s dead to me” to make the problem real. It translated an unfamiliar emotional experience into something investors could feel, not just analyze. The story did the work logic could not.
ACTION: Choose one personal moment where you first saw the problem clearly. Write it as a short scene. Who was there. What was said. What changed. Use it early in your story to create empathy before you explain your solution.
Pair Emotion With Proof
Hyman learned to combine the examples of confidence women felt during early dorm room trunk shows with data. Nearly all customers were renting brands they had never purchased before. Most later bought those brands. Story plus evidence made belief scale.
ACTION: Lead with the human transformation your product creates. Then support it with one or two metrics that show behavior actually changed. If you do not have data yet, run a small test. Capture both how people felt and what they did.
Prior to Rent the Runway, the average American woman bought about 64 new clothing items per year, with roughly 50% worn only once
Rent the Runway made it possible for a single garment to get rented 30X before retirement. Instead of 30 women buying 30 separate dresses, one item does the work of dozens, spreading production cost and environmental impact across many wears. Nearly half the year was spent dressing from a rotating closet.
The model also became a discovery engine: 98% of customers rent brands they've never bought before, and 80% later purchase a brand they first tried through renting.
Video to Watch:
In this video by the Stanford Graduate School of Business, Hyman shares the origin story for Rent the Runway and how her family background, early career experiences, and sense of community shaped the brand. The conversation offers a clear look at how personal context fuels confidence, creativity, and resilience, and how those foundations help founders navigate uncertainty on the path from idea to public company.
Watch here😀
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