Jenn Hyman built Rent the Runway on a contrarian insight back in 2009: women were already “renting” their clothes—borrowing from friends, cycling through fast fashion, and returning special-occasion outfits with the tags still on. Today, Jenn shares how she turned that overlooked behavior into one of the most influential fashion-tech companies of the last decade, why social media made outfit repetition feel impossible, and what fast fashion still gets wrong about how women actually shop.

Jenn also goes where most founders won’t; she tells Sammi about becoming one of the few women to ever take a consumer startup public—and the first to IPO with an all-female C-suite—only to watch the market flip weeks later and the stock fall more than 98% from its peak. She breaks down what the stock price does (and doesn’t) say about the business, the realities of life as a public-company CEO, the recent recapitalization that strengthened Rent the Runway’s balance sheet and pushed it toward free cash flow breakeven, and how competition from players like Nuuly is reshaping the rental landscape. Plus, they unpack the wild downfall of CaaStle, a would-be Rent the Runway copycat—and Jenn’s response is JUICY.

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Here’s what Sammi covers with Jenn:

00:00 Jenn Hyman’s Social Currency

04:07 Early Days of RTR

09:16 The Role of Social Media

11:18 Building a Resilient Team

16:19 The IPO Experience

21:22 Navigating Public Market Challenges

31:32 The Irony of Entrepreneurial Ego

32:25 Navigating Rent the Runway's Rollercoaster

34:49 The Future of Rental Economics

35:06 Rent the Runway's Marketing Mastery

39:00 Pricing Strategies and Customer Insights

40:38 Competitors and Market Shifts

47:31 The CaaStle Fraud Scandal

54:41 Social Currency Corner

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