Inside Rent the Runway’s Early Days and the Future of Commerce with Co-founder Jenny Fleiss
The Peel with Turner Novak
Turner Novak
4.6 • 11 Ratings
🗓️ 7 November 2024
⏱️ 65 minutes
🧾️ Download transcript
Summary
Jenny Fleiss is the Co-founder of Rent the Runway, and more recently started Roll Rider with her three kids.
We get into the early insights that led to Rent the Runway, building the company with no fashion or tech background, fundraising advice, what she’s thinking about the future of AI and commerce, and the latest company she’s building with her kids, Roll Rider.
For full show notes, visit: https://highlightai.com/share/9bc59c07-05ab-41aa-b37e-f35a7c92092d
Timestamps:
(00:00) Intro
(05:31) How social media was Rent the Runway’s first tailwind
(07:21) Being early to sustainable fashion
(09:21) Starting the company at HBS in 2008
(12:36) Launching with no fashion or tech background
(14:49) The three biggest early surprises
(18:44) Using “show don’t tell” to fundraise
(20:06) Why customer social proof was so important
(23:04) Spending only 10% of revenue on marketing
(25:12) Getting the NYT to cover their launch
(29:43) Early mistakes
(31:29) Re-building the product a few weeks before launch
(33:11) Why building their own logistics was so important
(38:59) Subscriptions, retail, and other key product decisions
(45:15) How the internet makes it harder to shop
(49:30) Building conversational commerce at Walmart
(53:48) Lessons from starting a company with her kids
(58:38) Favorite startups in AI and commerce
Referenced:
Rent the Runway: https://www.renttherunway.com/
NYT’s Launch Coverage: https://www.nytimes.com/2009/11/09/technology/09runway.html
Check out Roll Rider: https://rollrider.com/
Use code TURNER15 for 15% off
Follow Jenny:
Twitter: https://x.com/Jenny_RTR
LinkedIn: https://www.linkedin.com/in/jennifer-fleiss-18577314
Follow Turner:
Twitter: https://x.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Transcript
Click on a timestamp to play from that location
| 0:00.0 | As we started talking to customers, we heard this phrase, Facebook kills outfits. |
| 0:04.7 | The idea that women used to repeat an outfit with one group of friends and then another, |
| 0:09.2 | and you couldn't do that anymore, let alone the fact that you were now showcasing your outfit |
| 0:14.3 | and your look to so many more people. |
| 0:16.7 | We were all our own mini celebrities because of social media. |
| 0:20.1 | So the pain point for customers was that much more acute. |
| 0:23.7 | And so it was this really great confluence of events between this recessionary smart shopper moment and tailwind, |
| 0:29.8 | as well as the social media tailwind that created a bigger need and made that the timing for this product that we were working on Rent the Runway was going to be more impactful than ever. |
| 0:40.3 | Welcome to the Peel. I'm your host, Turner Novak, founder of Banana Capital. |
| 0:44.3 | Today's guest is Jenny Fleiss, co-founder of Rent the Runway, which allows anyone to rent, subscribe, and buy designer apparel and accessories, |
| 0:51.3 | and the new company she started with their kids, Roll Rider. We talked about the secret that started Run the Runway in 2009. |
| 0:57.8 | This inkling that women would want to talk about and share the fact that they rented. |
| 1:02.8 | We weren't sure if that behavior would be hush-hush, but it started to feel like that could be |
| 1:06.7 | something that was cool. The early days of getting things off the ground, despite having no fashion or tech background. |
| 1:12.6 | We wound up having to fire the engineering team. |
| 1:15.6 | We had hired like a month before our launch. |
| 1:17.6 | Getting the New York Times to cover the launch. |
| 1:20.6 | Someone on the wait list had the New York Times email address. |
| 1:23.6 | And we offered them to come and take photos. |
| 1:25.6 | We kind of knew it was like a pretty wild thing that if we were wearing our rent-the-runway dresses and we were up on ladders, fulfilling orders, that it would be a fun story. |
| 1:34.6 | Fundraising with show don't tell. |
| 1:36.6 | We wanted to always show them that unlock of the emotional connection with women in fashion. |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from Turner Novak, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of Turner Novak and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.

