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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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.
156 episodes
