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

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Episode 77: How to Build a Business That Fits (Without Burning Out): Lessons from a Former Meta Exec

What 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 startup

• Why customer-centric thinking outperforms flashy branding

• What role empathy plays in both business and personal relationships

• How to focus when your brain wants to chase all the ideas

• The underestimated power of writing things down (yes, really)

• Why your energy source matters more than your productivity hacks

Key Takeaways:

• Self-doubt is part of the entrepreneurial path—clarity comes from movement.

• Real magic happens when you trust your unique gifts.

• Integrity > algorithms

• Energy 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 Journey
03:07 – Overcoming Doubt in Entrepreneurship
06:06 – Strategic Frameworks for Problem Solving
08:54 – Understanding Customer Needs
11:56 – Sustainability in Fashion and Business Insights
15:05 – Collaboration and Community in Business
17:56 – Finding Inspiration Through Connection
20:56 – The Power of Genuine Relationships
24:02 – Navigating Challenges and Staying Authentic
29:03 – Navigating Relationships and Empathy
31:24 – Finding Energy and Inspiration
35:41 – The Birth of Taelor
39:22 – Customer-Centric Decision Making
44:05 – Balancing Work and Personal Energy
47:15 – Returning to Self and Connection

Links & 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.
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