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 
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