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

23 Apr 2026 · 35 min
Episode

23 Apr 2026 · 35 min

0:00

In this episode of The Room Podcast (Season 13, Inside Summit 2025), host Madison McIlwain and co‑host Claudia interview Julie Bornstein, a two‑time founder and former COO of Stitch Fix. Julie recounts her upbringing in Syracuse, her early fascination with mall‑based “search” for fashion, and her career trajectory through Nordstrom, Sephora, and Stitch Fix, where she helped blend human taste with algorithms. She explains how the launch of ChatGPT reshaped her view of search from simple retrieval to intent‑driven interpretation, prompting her to launch Daydream – an AI‑first “intent layer” that sits between consumers and retailers, translating complex natural‑language prompts (e.g., “revenge dress for a wedding in Paris with a Saltburn vibe”) into personalized product recommendations across a massive catalog. The conversation covers Daydream’s product architecture, its commission‑based business model, retailer partnerships, the challenge of overwhelming product assortments, and the need for deep product enrichment beyond raw catalog data. Julie discusses fundraising (first backer Kirsten Green at Forerunner, later Google Ventures, Index, etc.), the importance of long‑standing relationships, and the difficulty of hiring the right team. She details Daydream’s multi‑model LLM strategy, cloud‑provider choices, and the vision of a “stylist in your pocket” that proactively suggests outfits for events. The episode closes with Julie’s advice for young founders – gain experience, seek advisors, learn from good and bad leadership – and a tribute to Katrina, a woman who profoundly impacted her career at Stitch Fix. Throughout, the hosts intersperse sponsor reads and reflections on the evolving AI‑native commerce landscape.

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