Julie Bornstein thought it would be a cinch to implement her idea for an AI startup . Her résumé in digital commerce is impeccable: VP of ecommerce at Nordstrom, COO of the startup Stitch Fix, and founder of a personalized shopping platform acquired by Pinterest . Fashion has been her obsession since she was a Syracuse high schooler inhaling spreads in Seventeen and hanging out in local malls. So she felt well-positioned to create a company for customers to discover the perfect garments using AI.

The reality was much harder than she expected. I had breakfast recently with Bornstein and her CTO, Maria Belousova, to learn about her startup, Daydream , funded with $50 million from VCs like Google Ventures. The conversation took an unexpected turn as the women schooled me on the surp

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