In this inspiring episode, Anya Cheng shares her remarkable journey from a non-technical immigrant background to leading product and growth at giants like Facebook, eBay, Target, and McDonald's, and ultimately founding Taylor—an AI-driven menswear rental and styling service for busy professionals. Drawing from her experiences during the 2008 recession, Anya discusses overcoming job-hunting hurdles, the birth of Taylor from personal frustrations with fashion rentals, and how AI and human stylists combine to solve real pain points for ambitious men who prioritize success over style. She reveals growth strategies, lessons from big tech, and future plans for sustainability and corporate partnerships. Perfect for entrepreneurs, fashion innovators, and anyone navigating career pivots.Key Moments
Host welcomes Anya Cheng, highlighting her tech leadership at Facebook, eBay, and more. Anya introduces Taylor as an AI service that curates and rents real menswear for busy men, eliminating shopping and laundry.
Anya shares how imposter syndrome as a female immigrant leader at eBay sparked Taylor. She hated subscription boxes and rental hassles, realizing fashion companies ignore practical users.Key Quote: "Most of fashion companies are designing for people who are into fashion, not for people like me. I just want to get ready for the day... Success for me is not about looking good. It's about looking good to get a job, get the deal."
Fresh from Northwestern with a marketing master's, Anya ambushes recruiters, networks via professors, and cold-calls publishers amid layoffs—turning desperation into her first media role.
Anya explains why she didn't quit: By leveraging her reporter skills (e.g., interviewing, cold-calling), challenges felt manageable, fueling hope.
Two years in, Taylor's users aren't just renting clothes—they're buying "chances to succeed" (e.g., job interviews, deals). Customers value convenience like an "executive assistant," while suppliers seek detailed feedback to reduce waste.
AI powers onboarding (quizzes, photos) and recommendations from 27,000 garments, with human stylists refining via Zoom/text. It even generates SEO content for trends.
Partnerships with dating apps, fitness centers, law firms, and nonprofits outperform solo efforts. Content marketing educates on body types and travel perks (e.g., no luggage fees).
From a Shopify waitlist, Anya manually bought/s shipped sale items from Macy's to her first eager customer (a real estate agent), validating demand and iterating 100 times.
Big tech taught logical thinking (goals vs. strategies) to pitch investors. For Taylor, targeting men yields higher margins than women's rentals due to buy-through rates.
Illustrate a clear problem/persona (e.g., men's convenience vs. women's variety). Nail one giant feature (like Google's search bar). 3) Focus on product-market fit over features.
To learn more about Anya Cheng please visit her Linkedin ProfileTo learn more about Taelor please visit her website
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YOUR HOST - SIMON LADER
Simon Lader is the host of The Conference Room, Co-Founder of global executive search firm Salisi Human Capital, and lead generation consultancy Flow and Scale. Since 1997, Simon has helped cybersecurity vendors to build highly effective teams, and since 2022 he has helped people create consistent revenue through consistent lead generation.
Get to know more about Simon at:
Website: https://simonlader.com/
Twitter: https://twitter.com/simonlader
LinkedIn: https://www.linkedin.com/in/headhuntersimonlader/
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