Anya Cheng is the Founder and CEO of Taelor, an AI-powered fashion-as-a-service company transforming how men dress. With leadership experience at Meta, eBay, McDonald’s, and Target, Anya is an expert in product innovation, customer experience, and system-driven scalability. She was named one of Girls in Tech’s “40 Under 40” for her impact in tech, marketing, and entrepreneurship.
Here’s a glimpse of what you’ll learn:
- [02:44] Why Taelor focuses exclusively on men and what problem it solves
- [05:17] How AI and partnerships with 300+ brands power Taelor’s unique model
- [07:04] What inspired Anya to stop shopping and how rental fashion changed her life
- [10:39] How understanding customer psychology helped Taelor scale effectively
- [13:03] What Anya learned from big tech about categorization, logic, and system design
- [15:20] How Taelor partners with dating apps, fitness companies, and corporates to create new revenue streams
In this episode:
What if your entire wardrobe came to you—curated, sized, and ready to wear—with no shopping or laundry required? In this episode of the Systems Simplified podcast, Adi Klevit interviews Anya Cheng, the visionary behind Taelor, a systematized AI-powered clothing rental service designed for busy men who want to look great without the hassle.
Anya shares the origin of Taelor, inspired by her own search for clothing solutions as a tech leader who didn’t have time—or interest—in shopping. She explains how most fashion companies are designed for enthusiasts, not professionals who want to look good and move on with their day. Taelor fills this gap by combining personal styling, AI, and a highly systematized backend to deliver stylish outfits on demand.
The conversation also explores how Anya applies system thinking learned at Meta and eBay to streamline operations, categorize decisions logically, and create a scalable model. From partnerships with dating apps and fitness brands to sustainable corporate gifting, Taelor is redefining clothing through smart systems and strategic growth.
Resources mentioned in this episode:
- Adi Klevit on LinkedIn
- Business Success Consulting Group
- Anya Cheng on LinkedIn
- Taelor – Experience effortless style with rental and personal styling services. Get 25% OFF your first month of men's clothing subscription with code PODCAST25 - Sign up at Taelor
- Armoire – Women’s clothing rental subscription. Get 50% OFF your first month with code ArmoirexTaelor - Sign up at Armoire
- Taelor Gift Cards – Give the gift of time, convenience, and effortless style. Get 10% OFF with code PODCASTGIFT - Purchase Taelor Gift Cards
- Girls in Tech – 40 Under 40 Honorees
Quotable Moments:
- “Most fashion companies are built for people who love fashion. We built Taelor for people who don’t.”
- “Our customers want to look great, but they don’t want to think about it. They want peace of mind.”
- “What I learned from big tech is to think layer by layer—goal, strategy, tactics.”
- “Taelor is a service company that uses AI and styling to save customers time and mental load.”
- “When people look good, they perform better—and that’s the best gift a company can give its employees.”
Action Steps:
- Categorize business activities logically to improve clarity and decision-making.
- Use AI and automation to eliminate repetitive customer decisions and create convenience.
- Build offerings around solving practical customer problems—not just industry trends.
- Leverage strategic partnerships to extend your reach and increase lifetime value.
- Create systems that align with lifestyle needs, saving customers time and energy.
Sponsor for this episode:
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