In This Episode

What if your entire wardrobe came to you—curated, sized, and ready to wear—with no shopping or laundry required? In this episode of the Systems Simplified podcast, Adi Klevit interviews Anya Cheng, the visionary behind Taelor, a systematized AI-powered clothing rental service designed for busy men who want to look great without the hassle.

Anya shares the origin of Taelor, inspired by her own search for clothing solutions as a tech leader who didn’t have time—or interest—in shopping. She explains how most fashion companies are designed for enthusiasts, not professionals who want to look good and move on with their day. Taelor fills this gap by combining personal styling, AI, and a highly systematized backend to deliver stylish outfits on demand.

The conversation also explores how Anya applies system thinking learned at Meta and eBay to streamline operations, categorize decisions logically, and create a scalable model. From partnerships with dating apps and fitness brands to sustainable corporate gifting, Taelor is redefining clothing through smart systems and strategic growth.