#36: AI Shopping, The Future of Commerce & Why Trust Matters More Than Tech

Overview Julie Bornstein, a trailblazer in fashion, retail, and technology, shares her journey from breaking into the fashion industry to leading AI-driven innovations in commerce. The conversation explores the complexities of fashion as a taste-based category, the challenges of e-commerce search, and how AI is reshaping personalization. Julie also reflects on trust, long-term thinking, and her mission to make shopping smarter and more intuitive. Notable Quotes - If someone takes the time to really put thoughts together, I'll either respond or connect them to the right person. – Julie Bornstein, on the power of thoughtful outreach. - The hardest part about what we're doing now is the nondeterministic nature of LLMs. It’s very hard to describe what you want and have it come out the way you expect. – Julie Bornstein, on the challenges of building AI-driven solutions. - We want to build a system where if the customer wins, we win, and the brand or retailer wins. – Julie Bornstein, on aligning incentives in commerce. 🧵 Breaking Into Fashion Without a Network - Julie’s career began with handwritten letters to major fashion houses like Donna Karan, Ralph Lauren, and Calvin Klein. Only Donna Karan responded, giving her a start in the industry. - She emphasizes the importance of personalized, thoughtful outreach, even in today’s LinkedIn-driven world, as a way to stand out and secure opportunities. - Julie notes that this approach still works, sharing examples of young professionals landing internships and jobs through similar methods. 🛍️ The Business of Fashion & Why Brands Fail - Julie explains the fashion ecosystem: brands create demand and design, while retailers curate and sell. Success hinges on differentiation, clear customer targeting, and appropriate pricing. - Many brands fail due to a lack of a unique perspective, unclear customer focus, or misaligned pricing. - Nostalgia plays a role in reviving old brands, but success requires modernizing while retaining the original appeal. 🔍 Why E-Commerce Search is Broken - Traditional e-commerce search struggles with fashion because it’s taste-based, not keyword-based. Users often can’t articulate exactly what they want. - Julie’s platform, Daydream, uses AI to understand products deeply, combining text and image data to improve search relevance. - Unlike ad-driven platforms like Amazon, Daydream prioritizes trust by aligning success with customer satisfaction rather than ad revenue. 🤝 Selling a Startup & Lessons from Acquisitions - Julie sold her startup, The Yes, to Pinterest, driven by a combination of price, market conditions, and trust in Pinterest’s vision. - She highlights the challenges of post-acquisition integration, noting that visions often shift under new leadership. - Her experience in M&A, from Starbucks to Pinterest, taught her the importance of structuring deals for mutual success and navigating the complexities of cultural integration. 🌟 Building Daydream & The Future of AI in Fashion - Inspired by the potential of large language models (LLMs), Julie founded Daydream to solve the overwhelming nature of online shopping. - Daydream allows users to describe their needs in natural language or upload photos, leveraging AI to deliver personalized recommendations. - Julie envisions a future where shopping is smarter, easier, and more aligned with individual tastes, leaving a lasting impact on the fashion ecosystem.