Anya Cheng is the co-founder and CEO of Taelor, an AI-powered men’s clothing subscription service built around sustainability and convenience. She’s a Silicon Valley product and marketing leader with deep experience inside large consumer platforms, having helped launch Facebook and Instagram Shopping at Meta, led new business expansion at eBay, supported McDonald’s global food delivery growth, and shaped mobile commerce at Target. Over the years, she’s led teams across AI, eCommerce, and go-to-market work, and she’s also taught at Northwestern University. Her path blends big-company execution with startup building, and Taelor reflects that mix: a practical consumer business that uses data and operations, not just algorithms, to deliver a better experience.
In the conversation, Anya brings a clear-eyed view of what it really takes to build strong AI products. Rather than treating “good ideas” as the differentiator, she talks through how disciplined strategy—understanding who you’re serving, what they’re struggling with, and what’s worth building—creates an advantage that’s hard to copy. She also explains how AI is changing the way people discover brands, shifting attention from name recognition to whether a company’s information is easy for models to understand and surface in answers. From there, she gets specific about defensibility: in her view, lasting AI products are built on unique data, and one of the best ways to create it is through thoughtful human-in-the-loop systems. Using Taelor as an example, she shares how real customer feedback and rental behavior can reveal things internet data can’t, while also making sustainable fashion feel effortless for busy men. Along the way, she reflects on the realities of fundraising as a woman founder and how work is evolving as AI takes over more drafting and research, leaving humans to focus on judgment and decision-making.
