EXCLUSIVE: Ex-Stitch Fix, Gilt and Casper Execs Turn Off-price Fashion Into Fun and Games
Shopping for fashion is supposed to be fun, but as more of it moves online, the result has been “very functional, but pretty uninspiring,” said former Stitch Fix executive Lindsay Ferstandig. E-commerce works well when shoppers know what they want, but online stores and marketplaces have always been vexed by discovery and creating delightful online experiences.
Changing that will take some fresh thinking — and perhaps a healthy dose of data science. At least that’s what she and cofounder Philip Krim are betting on with the Yaysay mobile app, which is officially opening a public beta test on Wednesday.
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“We are building an AI-fueled, personalized, feed-based new mobile shopping paradigm that is focused on bringing the thrill of the treasure hunt — of off-price shopping — to an online experience,” Ferstandig, now Yaysay’s chief executive officer, told WWD.
Chasing discounted merchandise in places like T.J. Maxx, Ross and other stores is “where shopping is really fun,” she said, citing that the off-price market has $100-plus billion in revenue, yet only 3 percent coming from e-commerce.
Yaysay aims to recreate that experience online. The approach matches products to shoppers using artificial intelligence then limits availability, for a short window that creates a sense of urgency and even competition.
“We’ve looked outside of the e-commerce sector. We’ve looked at the places where people really enjoy spending their time on their phone, and they just walk away feeling like they’ve had fun, gotten some energy from that interaction,” Ferstandig continued. “For us, that’s social media, it’s games, it’s dating apps and the things that bring people back again, and again, because that interaction actually feels dynamic and fun.”
This was the cofounders’ “aha” moment, when they realized that shopping should feel dynamic and energizing, “more like a game than a way that you can get something done,” she added.
The action starts with the “Start Shopping” button, which brings the first of a series of looks to the screen. This is what’s known as “a rack” in Yaysay parlance.
“It’s app-based shopping and every day you get a new rack,” explained Krim. “That rack only has a limited number of items that our AI engine pulls from our inventory for you. So one, that’s very different than what exists online, where you just scroll endlessly. We only give you a certain number of items, and when you get to the end of your rack, that’s it. That’s the only number of items you can see for the day until your rack refreshes for you tomorrow.”
Once the deal is gone, he explained, it can’t be recovered.
“Those items are available to you and to select others that the AI pulls from, and people are competing for those items,” he said. When people add the item to the cart, it holds the product for 30 minutes, blocking it temporarily from being purchased by others.
Therein lies the game. The app also features a “Trending Now” feed that shows off deals that other users scored, tapping into FOMOs (or fear of missing out). The hope is that these mechanisms will prompt people to pop into the app regularly and check out their racks, just as some people jump into their social media feeds — except Yaysay was designed to be a lightweight, daily habit. The start-up calls the app “a five-minute daily dopamine boost.”
Ferstandig’s experience as Stitch Fix’s vice president of strategy and later Shop shows up in Yaysay’s data science DNA. AI curates selections as well as generates all the product photos, for a consistent interface and visual experience across labels that include Acne, A.L.C., Chloé, Isabel Marant, Ganni, Loewe, Vince and others. The benefits to brands may be even more obvious, particularly those looking for ways to liquidate excess inventory (which is, in reality, all of them).
For Krim, the former CEO of direct-to-consumer mattress brand Casper, Yaysay is more than a proof of concept. It’s validation.
“I’ve spent my whole career around e-commerce and retail, and the off-price category has just been one that I’ve always been amazed with,” he said. “It’s a staggeringly huge category and, candidly, what’s always bothered me is that these retailers are super dismissive of digital. They just don’t think that you can recreate the treasure hunt–type experience, online and digitally, and that’s where I fundamentally disagree with them.”
So does the founding team, which includes executives from Gilt Groupe, as well as investors, which pumped $10.3 million into the business via a seed round lead by Lightspeed Venture Partners. Its list of investors and advisers includes Alexandra Wilkis Wilson, Gilt Groupe’s founder; Rati Sahi, founder of The RealReal; Julie Bornstein, founder of TheYes; Shira Suveyke from ShopBop, Outnet and Gilt Groupe, and others.
Yaysay has been operating in test mode among friends and family since August, but now opens up the waitlist online at shopyaysay.com.
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