From Meta Exec to AI Fashion CEO: Anya Cheng on Growing With Connection, Energy & a Business Built on Empathy and Alignment

Episode 77: How to Build a Business That Fits (Without Burning Out): Lessons from a Former Meta ExecWhat happens when you leave big tech, trust your gut, and build a business that’s as intentional as it is innovative? In this episode of Return, Caitlan Siegenthaler sits down with Anya Cheng—founder of Taelor.Style—an AI-powered menswear rental service changing the game in sustainable fashion. From launching Facebook Shopping to disrupting the fashion industry with heart and strategy, Anya shares what it takes to stay aligned while building something bold. This is a conversation about energy, empathy, and unapologetically owning your magic.Anya opens up about navigating doubt, honoring your energy cycles, and how understanding human behavior (not just data) leads to real innovation. Whether you're feeling scattered, pivoting, or searching for clarity in your own business—this one will remind you that sustainable success starts with returning to yourself.What You’ll Learn in This Episode:How Anya transitioned from Meta to her own AI startupWhy customer-centric thinking outperforms flashy brandingWhat role empathy plays in both business and personal relationshipsHow to focus when your brain wants to chase all the ideasThe underestimated power of writing things down (yes, really)Why your energy source matters more than your productivity hacksKey Takeaways:Self-doubt is part of the entrepreneurial path—clarity comes from movement.Real magic happens when you trust your unique gifts.Integrity > algorithmsEnergy is personal. Don’t copy someone else’s morning routine.Customer feedback isn’t just nice to have—it’s the roadmap.Empathy and genuine relationships open unexpected doors.Your story, your upbringing, your essence—they’re all part of your magic.Chapters:00:00 – Introduction to Anya Cheng and Her Journey03:07 – Overcoming Doubt in Entrepreneurship06:06 – Strategic Frameworks for Problem Solving08:54 – Understanding Customer Needs11:56 – Sustainability in Fashion and Business Insights15:05 – Collaboration and Community in Business17:56 – Finding Inspiration Through Connection20:56 – The Power of Genuine Relationships24:02 – Navigating Challenges and Staying Authentic29:03 – Navigating Relationships and Empathy31:24 – Finding Energy and Inspiration35:41 – The Birth of Taelor39:22 – Customer-Centric Decision Making44:05 – Balancing Work and Personal Energy47:15 – Returning to Self and ConnectionLinks & Resources: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: PODCAST25Sign up at: https://taelor.style/pages/membershipArmoire: Get 50% OFF your first month of women's clothing subscription.Use code: ArmoirexTaelorSign up at: https://www.armoire.style/refer/ArmoirexTaelorGive the gift of time, convenience, and effortless stSupport the showProduced by Caitlan SiegenthalerCover Art by Kiara OparaIf you enjoyed this episode, share it with a friend, post it to your Instagram stories, and tag me. And if you really loved it, the best thank-you is a written review on Apple Podcasts or a comment on Spotify. That is a beautiful energetic exchange for Caitlan creating the show.