528: From startup founder to product success and why interacting with people is the big change – with Anya Cheng

How an AI-powered fashion startup achieved product-market fit Watch on YouTube TLDR In this episode, we’re joined by Anya Cheng, former product leader at Meta, eBay, McDonald’s, and Target, and current founder of the AI-powered fashion startup Taelor. Her journey from corporate product management to successful startup founder offers valuable lessons for product managers and innovators. The key message: Focus on solving one problem exceptionally rather than competing on multiple features. Key Topics * Why successful products often start with a single powerful feature * How to discover and validate product-market fit through deep customer research * The importance of balancing customer feedback with your own product vision * Ways to create value on both customer and supplier sides of your business * Lessons from Target’s iPad app success through radical feature minimization * The value of breaking out of your industry bubble for innovation insights Introduction We all face numerous challenges creating products customers love—understanding the customer and their unmet needs, achieving product-market fit, working with stakeholders, scaling the product in the marketplace, and more. Today we’ll learn how to overcome some of those challenges from a product leader with experience at Target, McDonalds, eBay, and Meta, and now as Founder and CEO of Taelor. Our guest, Anya Cheng, founded Taelor, combining her leadership experience at B2Cs and her knowledge of tech product management, to make it easy for men to wear stylish clothes for any occasion. Anya also is mentor at 500 Startups and a teacher of product management for Northwestern University.  A Fresh Perspective on Product Development Anya challenged common assumptions about product development strategy. Instead of advocating for feature-rich products or complex innovation frameworks, she emphasized the power of solving one problem exceptionally. This approach has informed her success across different industries and roles, from retail to technology. Core Product Development Challenges: The Power of Single-Feature Focus Anya highlighted a mistake many startups and product teams make: trying to compete with established companies by matching or exceeding their feature lists. The Feature Competition Trap During her work mentoring product managers and startups, Anya noticed a recurring pattern. Teams often pitch their products by comparing them to industry giants: “It’s like Uber, but with these extra features” or “It’s Amazon, plus these additional capabilities.” The problem? This approach fundamentally misunderstands how successful products actually emerge and grow. Large companies can quickly replicate individual features, making it nearly impossible for smaller players to compete on feature quantity. Instead, a startup should focus on solving one problem better than anyone else. Historical Examples of Successful Single-Feature Products To illustrate the power of focused problem-solving, Anya shared three examples: Company Initial Core Feature Outcome Google Simple search bar Outperformed Yahoo’s comprehensive portal YouTube Video upload and sharing Acquired by Google Instagram Photo filters Acquired by Meta The Key to Standing Out The lesson Anya learned from both her corporate experience and startup journey is clear: Success comes from doing one thing exceptionally rather than doing many things adequately. She shared wisdom from her mentors, including founders of Rotten Tomatoes and YouTube, who emphasized that startups should focus on having “one giant check mark” instead of many small ones.