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Julie Bornstein thought<\/span> it would be a cinch to implement her idea for an AI startup<\/a>. Her r\u00e9sum\u00e9 in digital commerce<\/a> is impeccable: VP of ecommerce at Nordstrom, COO of the startup Stitch Fix, and founder of a personalized shopping platform acquired by Pinterest<\/a>. 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.<\/p>\n 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<\/a>, funded with $50 million from VCs like Google Ventures. The conversation took an unexpected turn as the women schooled me on the surprising difficulty of translating the magic of AI systems into something people actually find useful.T<\/p>\n Her story helps explain something. My first newsletter of 2025 announced that it would be The Year of the AI App<\/a>. Though there are indeed many such apps, they haven\u2019t transformed the world as I anticipated. Ever since ChatGPT launched in late 2022, people have been blown away by the tricks performed by AI, but study after study has shown that the technology has not yet delivered a significant boost in productivity. (One exception: coding.) A study published in August<\/a> found that 19 out of 20 AI enterprise pilot projects delivered no measurable value. I do think that productivity boost is on the horizon, but it\u2019s taking longer than people expected. Listening to the stories of startups like Daydream that are pushing to break through gives some hope that persistence and patience might indeed make those breakthroughs happen.<\/p>\n Bornstein\u2019s original pitch to VCs seemed obvious: Use AI to solve tricky fashion problems by matching customers with the perfect garments, which they\u2019d be delighted to pay for. (Daydream would take a cut.) You\u2019d think the setup would be simple\u2014just connect to an API for a model like ChatGPT and you\u2019re good to go, right? Um, no. Signing up over 265 partners, with access to more than 2 million products from boutique shops to retail giants, was the easy part. It turns out that fulfilling even a simple request like \u201cI need a dress for a wedding in Paris\u201d is incredibly complex. Are you the bride, the mother-in-law, or a guest? What season is it? How formal a wedding? What statement do you want to make? Even when those questions are resolved, different AI models have different views on such things. \u201cWhat we found was, because of the lack of consistency and reliability of the model\u2014and the hallucinations\u2014sometimes the model would drop one or two elements of the queries,\u201d says Bornstein. A user in Daydream\u2019s long-extended beta test would say something like, \u201cI\u2019m a rectangle, but I need a dress to make me look like an hourglass.\u201d The model would respond by showing dresses with geometric patterns.<\/p>\n Ultimately, Bornstein understood that she had to do two things: postpone the app\u2019s planned fall 2024 launch (though it\u2019s now available, Daydream is still technically in beta until sometime in 2026) and upgrade her technical team. In December 2024 she hired Belousova, the former CTO of Grubhub, who in turn brought in a team of top engineers. Daydream\u2019s secret weapon in the fierce talent war is the chance to work on a fascinating problem. \u201cFashion is such a juicy space because it has taste and personalization and visual data,\u201d says Belousova. \u201cIt\u2019s an interesting problem that hasn’t been solved.\u201d<\/p>\n What\u2019s more, Daydream has to solve this problem twice<\/em>\u2014first by interpreting what the customer says and then by matching their sometimes quirky criteria with the wares on the catalog side. With inputs like I need a revenge dress for a bat mitzvah where my ex is attending with his new wife,<\/em> that understanding is critical. \u201cWe have this notion at Daydream of shopper vocabulary and a merchant vocabulary, right?\u201d says Bornstein. \u201cMerchants speak in categories and attributes, and shoppers say things like, \u2018I\u2019m going to this event, it\u2019s going to be on the rooftop, and I’m going to be with my boyfriend.\u2019 How do you actually merge these two vocabularies into something at run time? And sometimes it takes several iterations in a conversation.\u201d Daydream learned that language isn\u2019t enough. \u201cWe\u2019re using visual models, so we actually understand the products in a much more nuanced way,\u201d she says. A customer might share a specific color or show a necklace that they\u2019ll be wearing.<\/p>\n Bornstein says Daydream\u2019s subsequent rehaul has produced better results. (Though when I tried it out, a request for black tuxedo pants showed me beige athletic-fit trousers in addition to what I asked for. Hey, it\u2019s a beta.) \u201cWe ended up deciding to move from a single call to an ensemble of many models,\u201d says Bornstein. \u201cEach one makes a specialized call. We have one for color, one for fabric, one for season, one for location.\u201d For instance, Daydream has found that for its purposes, OpenAI models are really good at understanding the world from the clothing point of view. Google\u2019s Gemini is less so, but it is fast and precise.<\/p>\n<\/div>\nFashionista Fail<\/h2>\n