From Stitch Fix to AI Search with Daydream Founder Julie Bornstein | Inside Summit 2025 [LIVE]

Welcome back to another episode of The Room Podcast! This week, Claudia and Madison sit down with Julie Bornstein, founder and CEO of Daydream, a new AI-powered shopping platform reimagining how people discover fashion online. Julie is a two-time founder with deep roots in digital commerce, having previously helped build Stitch Fix and later founded The Yes, which was acquired by Pinterest. With decades of experience at the intersection of retail, technology, and consumer behavior, Julie has been at the forefront of how people shop as the internet — and now AI — evolves.

In this episode, Julie shares why search has always been the hardest and most important problem in e-commerce, and how generative AI finally unlocks a more human way to shop. She walks through the lessons she learned building algorithmic fashion at Stitch Fix, why inventory ownership limits personalization, and how The Yes shaped her thesis around intent-driven discovery. We also dive into founding Daydream after an acquisition unwind, the challenges of hiring the right early team, navigating retailer relationships without becoming an ads business, and what the future of shopping looks like when your stylist lives in your pocket. Tune in for a masterclass on consumer AI, founder resilience, and why being early — twice — doesn’t make it easier the third time around.

(00:00) Introduction
(05:20) Where did Julie grow up and how did it shape her view of the world?
(06:31) Did Julie always think she would become a founder?
(07:42) How did Julie’s early career in retail and e-commerce shape what she’s building today?
(09:59) How did Julie’s philosophy evolve from Stitch Fix to The Yes to Daydream?
(11:54) Why did Julie decide to become a founder again after selling The Yes to Pinterest?
(14:54) How does Daydream avoid getting squeezed between retailers and consumers?
(17:58) Who is Daydream’s core customer and why did Julie choose them first?
(18:45) Who was the first investor to say yes to Daydream?
(19:39) What unexpected challenges did Julie face early at Daydream?
(21:41) How is AI changing Daydream’s business model decisions?
(22:26) Should retailers rethink site architecture in an AI-driven search world?
(23:14) How can companies make products more discoverable in an LLM-first future?
(23:33) Does better AI indexing by retailers threaten Daydream’s value?
(25:48) How does Daydream think about LLM interoperability and model choice?
(26:44) How should retailers think about cloud providers in modern e-commerce stacks?
(27:57) Does Julie consider Daydream an AI-native company?
(29:23) What does the future of online retail look like?
(31:39) What advice does Julie have for new founders?
(33:44) Who is a woman in Julie's life that has had a profound impact on her and her career?

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