The Co‑Founder Who Put Designer Dresses in the Mail
She and her classmate had an idea at Harvard. Rent designer dresses instead of buying them. Rent the Runway was born.
Jennifer Fleiss grew up in New York City.
She sold lemonade as a child.
She watched her parents run a real‑estate business.
Childhood
She was born in the city that never sleeps.
She learned early how a business works.
She liked to trade small items with friends.
Family & Hometown
Her parents were real‑estate agents.
They managed a business together.
Their office was a daily sight for her.
Education
She earned a BA in political science from Yale in 2005.
She graduated cum laude.
She later earned an MBA from Harvard Business School in 2009.
Early Career
She joined Morgan Stanley after college.
She worked in the Strategic Planning Group.
She helped plan long‑term company strategy.
She then moved to Lehman Brothers.
She analyzed growth opportunities for the Asset Management Group.
Co‑founding Rent the Runway
She met Jennifer Hyman at Harvard Business School.
They saw women with closets full of one‑time dresses.
They tested the idea by renting dresses on campus.
They held pop‑up trunk shows at Yale and Harvard.
They used a PDF “call us if you want to rent” form.
Investors were skeptical during the recession.
Their first check came after a partner convinced Bain partners.
They secured a term sheet with a 24‑hour signature clause.
First customers were fellow students.
The service let women rent designer dresses for real events.
Rent the Runway launched in November 2009.
The company grew to an e‑commerce platform.
It raised about $326 million before its IPO.
It went public on October 27, 2021.
Revenue reached $306.2 million in FY 2024.
Jennifer Fleiss left the company in 2017.
She later co‑founded JetBlack, a text‑based shopping service.
She served as its CEO until 2020.
She now partners with Volition Capital.
She lives in New York City with her husband and three children.
She enjoys running and yoga.
She mentors female founders.
She often says, “No doesn’t mean no, it means not right now.”
Her current work includes advising Melody Arc, Nectar Social, and Curated For You.
She helps launch the premium text‑shopping service NOIR in 2026.
She also runs Roll Rider with her children.
She holds board seats at the Lanvin Group and Shutterfly.
Jennifer Fleiss shows that a simple idea can change an industry.
Her story teaches young builders to test early and master logistics.
The Rise of Rent the Runway
The Founding Story
Jennifer Fleiss grew up in New York City. She sold lemonade as a child. Her parents ran a real‑estate business together. She watched them manage a company. She went to Yale and graduated cum laude in political science in 2005. She earned an MBA from Harvard Business School in 2009.
At Harvard, she met Jennifer Hyman. They were classmates. They saw women with closets full of dresses worn once. They asked how to fix the problem. They tested the idea by buying dresses and renting them at pop‑up shows on campus. They used a PDF that said “call us if you want to rent.” The tests showed real demand.
In November 2009 they launched Rent the Runway. The company is an e‑commerce platform that lets customers rent, subscribe to, or buy designer apparel and accessories.
First Customers and Product
The first customers were students at Yale and Harvard. They rented dresses from the pop‑up events. The dresses were designer pieces. Customers could try them on before renting. The service let women wear high‑fashion without buying.
Early sales came from the campus trials. The founders collected feedback and improved the process. They added a “call us if you want to rent” PDF to make ordering easy.
Early Struggles and Turning Points
Fundraising was hard. The economy was in a recession. Investors were skeptical. One investor, Scott Friend, helped convince his Bain partners. The team secured a term sheet that required a signature within 24 hours.
When they pitched to Diane von Furstenberg, she said the idea would not work. The rejection was demoralizing. The founders kept testing and refining the model.
The first big check arrived after the 24‑hour term sheet was signed. The money allowed them to build a logistics system. They created a network to ship, clean, and return dresses.
A key turning point was the launch of a subscription service. It gave steady revenue and attracted more customers. The model proved that high‑fashion could be affordable through renting.
Growth, Funding, and IPO
Rent the Runway grew quickly. Revenue reached about $100 million in 2017. By the fiscal year ending January 31 2024, revenue was $306.2 million.
The company raised about $326 million in pre‑IPO funding across 12 rounds. Investors included venture firms and strategic partners.
In October 2021 the company went public on Nasdaq under the ticker RENT. The IPO was priced at $21 per share and raised $357 million.
Rent the Runway also made an acquisition. It bought the try‑on service Go Try It On. The acquisition added new technology for virtual fittings.
After the IPO, the company faced pandemic‑related losses and a 2026 legal settlement over IPO disclosures.
Jennifer Fleiss left Rent the Runway in 2017. She later became a partner at Volition Capital and continued to mentor female founders.
Setbacks
Jennifer Fleiss faced early doubt from investors. The idea came during a recession. Funding was hard to get. An early pitch was rejected by Diane von Furstenberg. She said the concept would not work. The co‑founders kept testing on campus. They ran pop‑up shows at Harvard and Yale. They used a PDF form to collect rent requests. The first check arrived only after a partner at Bain was convinced. The early years required long hours and tight cash flow.
Criticism and Controversies
Rent the Runway grew fast after its 2009 launch. Some critics said the model was unsustainable. The company’s logistics were called “too complex.” In 2026 the firm settled a legal case about its 2021 IPO disclosures. The settlement was reported in the news. The case did not name Fleiss personally, but it affected the brand she co‑founded. Analysts also pointed to pandemic losses in 2020‑2021. Those losses sparked debate about the rental model’s resilience.
What Changed Recently
After leaving Rent the Runway in 2017, Fleiss started Jetblack. She ran Jetblack until 2020. She then joined Volition Capital as a partner. She began advising new startups. In 2024 she helped launch the NOIR shopping service. The service started in April 2026. She also founded Roll Rider with her children. She sits on boards at Lanvin Group and Shutterfly. Her focus now mixes investing, mentoring, and product building.
Where They Are Now (2026)
Jennifer Fleiss lives in New York City. She has a husband and three children. She runs daily yoga and runs for fitness. She mentors female founders. She advises ventures like Melody Arc, Nectar Social, and Curated For You. She works with the ShopMy team on the NOIR service. She continues as an operating partner at Volition Capital. She remains a board member at Lanvin Group and Shutterfly. Her career now blends investment, mentorship, and new product creation.
Why the story matters
Jennifer Fleiss shows that a simple idea can become a global brand. She proved that testing early saves money. She turned rejection into perseverance. She moved from founding to investing, helping the next wave of founders. Her path teaches that logistics matter as much as vision. Great ideas need great execution.
The Record
Education: BA Political Science, Yale (cum laude, 2005); MBA Harvard Business School (2009)
Co‑Founded: Rent the Runway (2009); Jetblack (2017)
Current Roles (2026): Partner at Volition Capital; Advisor to Melody Arc, Nectar Social, Curated For You; Board member Lanvin Group, Shutterfly; Builder of NOIR service; Founder of Roll Rider
Timeline
2005 to Graduated Yale cum laude in political science.
2009 to Earned MBA from Harvard Business School.
Nov 2009 to Co‑founded Rent the Runway.
2017 to Co‑founded Jetblack while at Walmart incubator.
2020 to Left Jetblack.
Oct 2021 to Rent the Runway IPO at $21 per share.
2021 to Joined Volition Capital as partner.
2024 to Helped launch NOIR shopping service.
2026 to Advises multiple startups and serves on two corporate boards.