What happens when tech meets fashion? You get Taelor—a game-changing men’s clothing subscription service that blends AI-powered styling with expert human touch. In this episode, I sit down with Anya Cheng, Taelor’s Founder & CEO and a Silicon Valley standout who's led digital innovation at Meta, eBay, McDonald’s, and Target.

We talk about:

• Why personalization and sustainability are the future of fashion

• How AI can make getting dressed less stressful (and more stylish)

• Anya’s career journey through Big Tech and into entrepreneurship

• Building a business that helps people show up with confidence

• The reality of being a female founder in male-dominated industries

• What she wishes more people knew about launching a startup

Special Offers Just for Listeners:

• 🎁 25% OFF your first month at Taelor — Use code PODCAST25

• 👗 50% OFF your first month at Armoire — Use code ArmoirexTaelor

• 🎁 10% OFF Taelor Gift Cards — Use code PODCASTGIFT Buy Here

About Anya Cheng: Anya is a best-selling author, two-time TED speaker, and award-winning entrepreneur whose work has shaped global eCommerce experiences. She holds advanced degrees from Northwestern and Chicago Booth and teaches at Northwestern University and 500 Global.

Tune in to hear how she’s reimagining fashion—and how AI might just be your new personal stylist.