The Root of All Success with The Real Jason Duncan 326: From Meta to Menswear: How Anya Cheng Built an AI Fashion Startup
What if AI could solve one of fashion’s biggest problems—waste—while helping men look sharp without ever setting foot in a mall?
In this episode of The Root of All Success, I sit down with Anya Cheng, a Silicon Valley tech executive turned founder of TAELŌR, an AI-powered clothing rental and styling platform for men that’s transforming how fashion meets technology and sustainability.
Before launching TAELŌR, Anya helped build Facebook and Instagram Shopping at Meta, led innovation at eBay and Target, and scaled McDonald’s global food delivery. Today, she’s using AI to make fashion smarter, more sustainable, and accessible to busy professionals.
We dive into how Anya turned a personal frustration into a groundbreaking business model—and what her journey reveals about innovation, leadership, and courage in a male-dominated industry.
💡 In this episode, you’ll learn:
- How AI is transforming the fashion industry from waste to sustainability
- Why Anya left big tech to build a purpose-driven startup
- The mindset shift needed to move from executive to entrepreneur
- How TAELŌR uses AI + human stylists to create personalized fashion experiences
- The surprising link between style confidence and business success
- Why sustainability isn’t just a buzzword—it’s the future of business
Anya’s story is proof that true success starts when you stop chasing trends—and start creating them.
🎧 Watch or listen to the full episode now to discover how innovation, purpose, and sustainability can reshape entire industries.
Who is Anya Cheng?
Anya Cheng is the Founder & CEO of Taelor, an AI-powered men's clothing subscription service promoting sustainable fashion. A Silicon Valley entrepreneur, she has been recognized among "Girls in Tech 40 Under 40" for her expertise in tech product management and marketing.
Anya played a pivotal role in launching Facebook and Instagram Shopping at Meta, led new business expansion at eBay, and helped grow McDonald’s global food delivery. She also shaped Target’s mobile commerce and has led teams in AI, product management, UX, and marketing across Fortune 500 companies.
Her work has earned 20+ prestigious awards, including the Webby Award for Best Shopping App, Best Mobile App Award, and The Communicator Award. A best-selling author, adjunct professor, and two-time TED speaker, she lectures at Northwestern University and 500 Global and is a sought-after keynote speaker.
Anya’s award-winning venture, Taelor, won first place at Draper University’s Startup Competition and was named a Startup to Watch by Bay Area Inno. She holds a Master’s in Integrated Marketing Communications from Northwestern University and an MBA from the University of Chicago Booth School of Business.
Anya Cheng’s Website Link: https://taelor.style/
Anya Cheng’s Social Media Link:
Taelor: https://taelor.style/pages/membership
Anya LinkedIn: linkedin.com/in/anyacheng
Taelor LinkedIn: https://www.linkedin.com/company/taelor/
Taelor Instagram: https://www.instagram.com/taelor.style/
Anya Photo: https://tinyurl.com/anyaphoto
Anya Detailed Bio: https://tinyurl.com/anyasbio
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