How an AI-powered fashion startup achieved product-market fit

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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.

This approach requires:

• Identifying a specific, valuable problem to solve
• Developing a focused solution that addresses that problem better than any alternative
• Resisting the temptation to add features just because competitors have them
• Maintaining focus on core value proposition during growth

Finding Product-Market Fit: The Taelor Case Study

The journey to product-market fit often begins with a personal pain point, but successful products emerge when founders look beyond their own experiences. Anya’s development of Taelor offers valuable lessons in how to validate and expand upon initial product insights.

From Personal Problem to Market Opportunity

Anya found herself wanting to look more professional but discovered existing clothing services weren’t designed for busy professionals who prioritized efficiency over fashion. This led her to explore whether others faced similar challenges.

Through market research, she discovered her ideal customers weren’t whom she initially expected. While her original problem centered on professional women’s clothing needs, her research revealed a more acute pain point among busy professional men who:

• Need to look good for various occasions
• Don’t enjoy shopping
• Want to save time on clothing decisions
• Prefer efficiency over fashion exploration

Developing the Value Proposition

Based on this customer understanding, Taelor evolved into a comprehensive solution combining several key elements:

Service Component	Customer Benefit
AI-Powered Recommendations	Personalized outfit selections based on schedule and preferences
Monthly Subscription	Regular rotation of 10 clothing items
Professional Styling	Expert guidance without requiring fashion knowledge
Laundry Service	Elimination of cleaning and maintenance hassles

Validating the Model

Anya explained that although Taelor sells clothes, their real value proposition is helping customers save time while getting ready for the week.  The service attracted a surprisingly diverse customer base, ranging from 16 to 85 years old, including professionals across various industries – from sales executives to pastors. This broad appeal confirmed that the core problem (wanting to look good without spending time on fashion) resonated across demographics.

Taelor’s customers pay a monthly fee and receive ten clothing items per month. They answer some questions about their current favorite clothes and clothing issues. They can upload a picture, get a 15-minute free consultation with a human stylist, and provide information about special events they’re dressing for each month. An AI uses this information to pick five clothing items that are mix-and-matched into two to three outfits, which are shipped to the customer. They can wear these clothes for two weeks, mail the dirty clothes back, and keep any pieces they want.

The business model created multiple value streams:

• Monthly subscription fees for the core service
• Purchase options for items customers particularly like
• Significant discounts (30-70% off) on pre-owned items

Thorough customer research and iterative development can transform a personal insight into a viable product with broad market appeal. The key was moving beyond initial assumptions to discover and validate deeper customer needs.

Customer Research and Product Evolution: Uncovering Hidden Opportunities

Anya emphasized how continuous customer research revealed unexpected opportunities and shaped Taelor’s product evolution. Her approach to gathering and acting on customer insights offers valuable lessons for product managers at any stage.

Multi-Channel Research Approach

Rather than relying on traditional surveys alone, Taelor implemented a comprehensive research strategy that combined multiple touchpoints:

Research Channel	Insights Gained	Impact on Product
Style Quiz	Initial fit preferences and style comfort zones	Improved AI recommendations
Stylist Consultations	Detailed customer concerns and aspirations	Enhanced personalization features
Direct Customer Communication	Real-time feedback and emerging needs	New service opportunities identified
Post-Use Feedback	Product quality and fit issues	Refined clothing selection process

Emerging Customer Needs

This deep customer engagement revealed several unexpected opportunities for service expansion:

• Gift recommendations for special occasions
• Style guidance beyond clothing (haircuts, accessories)
• Corporate partnership opportunities for employee benefits
• Educational institution collaborations for student interview preparation

The Human Touch in AI-Driven Products

Taelor decided to maintain human stylists alongside AI capabilities. While they could have automated all customer communications, they discovered that human interaction provided invaluable product development insights. This human element helped them:

• Understand nuanced customer needs that might not appear in data
• Identify patterns in customer requests before they become trends
• Build stronger relationships with customers
• Gather qualitative feedback that improved their AI systems

Strategic Partnerships

The research also led to strategic partnership opportunities that expanded the product’s value proposition. These included:

• Collaborations with women’s rental companies for gift services
• Partnerships with dating apps for style preparation
• Corporate programs for employee benefits
• Educational institution partnerships for student career preparation

This systematic approach to customer research and product evolution demonstrates how careful attention to customer feedback can reveal new opportunities while strengthening the core value proposition.

Supply Side Innovation: Solving Industry-Wide Challenges

Anya revealed how Taelor’s innovation extends beyond customer service to address significant industry challenges. This dual-sided approach to product development offers lessons for product managers about finding opportunities in industry-wide problems.

Addressing Fashion Industry Waste

The fashion industry faces two challenges that Taelor’s  business model helps address:

Industry Challenge	Scale of Impact	Taelor’s Solution
Direct-to-Landfill Waste	30% of new clothes	Rental model extending clothing lifecycle
Carbon Emissions	10% from fast fashion	Sustainable clothing rotation system

Creating Value for Suppliers

What makes Taelor’s approach particularly innovative is how it transforms these industry challenges into opportunities for brands. The platform serves as:

• A real-world testing ground for new designs
• A direct feedback channel from customers
• A solution for inventory management
• A market research platform for future collections

Market Testing Innovation

Anya shared how Taelor has become a valuable testing platform for clothing brands in several ways:

Testing Aspect	Brand Benefit
Pre-Release Testing	Real customer feedback before full production
Durability Assessment	Quality testing through multiple wears and washes
Fit Verification	Customer feedback on specific design elements
Market Validation	Early indicators of design popularity

Breaking Traditional Distribution Models

The platform also solves a significant challenge for new brands: finding their initial customer base. Anya explained how traditional distribution channels often involve multiple intermediaries, resulting in:

• Delayed feedback from end customers
• Limited understanding of customer preferences
• Reduced ability to iterate on designs
• Increased inventory risk

By providing direct access to customers and immediate feedback, Taelor helps brands make more informed decisions about their products while reducing waste and improving sustainability. This demonstrates how innovative product development can create value for multiple stakeholders while addressing larger industry challenges.

Key Product Management Lessons: Trust, Testing, and Breaking Bubbles

Anya shared several pivotal lessons from her product management journey that challenge conventional wisdom. These insights, drawn from both successes and failures, offer valuable guidance for product managers at any stage of their careers.

Trust Your Product Knowledge

Anya shared a story about her early pitching experiences that illustrated a common product manager challenge. In preparing for startup competitions, she initially focused on memorizing answers to potential questions, consulting 42 former judges. However, this over-preparation actually hindered her ability to respond authentically and confidently.

Key lessons she learned about product leadership:

• Value your deep product knowledge as the product’s “parent”
• Trust your understanding developed through daily engagement
• Balance external input with your own expertise
• Respond authentically rather than reciting prepared answers

Think Beyond Utility

One of Anya’s most significant realizations came after transitioning from corporate to startup environments. She discovered that successful product development requires thinking beyond pure utility:

• Move beyond the corporate “usefulness” mindset
• Embrace curiosity about different perspectives
• Seek insights from unexpected sources
• Break out of industry and professional bubbles

Value of Diverse Perspectives

Anya emphasized how her most valuable insights often came from unexpected sources:

• Successful entrepreneurs outside tech
• Professionals from different industries
• Customers with unique use cases
• Team members with diverse backgrounds

Successful product management isn’t just about following established frameworks – it’s about developing the judgment to know when to trust your instincts, question assumptions, and seek diverse perspectives.

Conclusion

Throughout my conversation with Anya Cheng, one theme consistently emerged: Successful product development isn’t about matching competitors feature-for-feature or trying to solve every customer problem. Instead, it’s about identifying a significant problem, solving it exceptionally, and having the discipline to maintain that focus even as your product grows. Her journey from leading product teams at major tech companies to founding Taelor demonstrates how this principle applies across different scales and industries.

For product managers and innovators, the lessons from Anya’s experience offer a refreshing perspective on product development. Whether you’re working in a large corporation or leading a startup, success comes from deeply understanding your customers, questioning your assumptions, embracing diverse perspectives, and having the courage to maintain a singular focus on solving one problem exceptionally.

Useful Links

• Connect with Anya on LinkedIn
• Check out Taelor and use code global30 to get 30% off your first month of subscription or globalgitft10 to get 10% off a gift card

Innovation Quote

“A great product solves a real problem with a singular, powerful value proposition.” – Anya Cheng

Application Questions

1. How could you simplify your current product down to one “giant check mark” – a single feature or capability that solves a crucial problem better than any alternative? What would you need to remove or change to achieve this focus?
2. How could your team expand your customer research methods beyond traditional approaches? Consider Anya’s example of having customer service representatives purposefully engage with users to gather product development insights. What new channels could you create for deeper customer understanding?
3. Looking at your product’s recent feature additions, how many were driven by competitor comparison versus genuine customer needs? How could you reframe your feature prioritization process to focus more on solving specific customer problems exceptionally?
4. How could you break out of your industry bubble to gain fresh perspectives on your product challenges? What unexpected sources or diverse viewpoints could you engage with to inspire innovation in your product development process?
5. Consider the Target iPad app example: How could your team apply radical feature minimization to your product? What would happen if you reduced your product to just two core capabilities that align perfectly with your key value proposition?

Bio

Anya Cheng is the Founder and CEO of Taelor, a leading men’s clothing subscription service that provides personal styling and curated rentals, powered by expert stylists and AI. A Girls in Tech 40 Under 40 honoree, she previously led eCommerce and digital innovation teams at Meta, eBay, Target, and McDonald’s.

Experience effortless style with rental and personal styling services:

Taelor: Get 25% OFF your first month of men’s clothing subscription.
Use code: PODCAST25
Sign up at: https://taelor.style/pages/membership

Armoire: Get 50% OFF your first month of women’s clothing subscription.
Use code: ArmoirexTaelor
Sign up at: https://www.armoire.style/refer/ArmoirexTaelor

Give the gift of time, convenience, and effortless style:

Taelor Gift Cards: Get 10% OFF Use code: PODCASTGIFT
Purchase at: https://taelor.style/products/menswear-rental-gift-card

 

Thanks!

Thank you for taking the journey to product mastery and learning with me from the successes and failures of product innovators, managers, and developers. If you enjoyed the discussion, help out a fellow product manager by sharing it using the social media buttons you see below.

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