Nov 24, 2025
What if getting dressed could be effortless, stylish, and sustainable? In this episode of The Necessary Entrepreneur, host Mark Perkins sits down with Anya Cheng, founder and CEO of Taelor, a Silicon Valley startup transforming men’s fashion through AI-powered styling, subscription rentals, and expert human guidance.
Anya shares her journey from leading product and marketing teams at Meta, eBay, and Target to founding Taelor, a company designed to help busy men look their best without the hassle of shopping, laundry, or outfit planning. Learn how she combines technology, machine learning, and human styling insights to create personalized fashion experiences that boost confidence, career success, and sustainability.
In this episode, you’ll discover:
-
How Taelor AI is revolutionizing men’s fashion with subscription rentals and data-driven styling
-
Lessons from Anya’s career journey and founding a startup from zero to one
-
Using AI to combine human intuition with machine learning for perfectly matched outfits
-
The intersection of sustainability, fashion, and business innovation
-
Insights on fundraising, investor selection, and scaling a high-impact startup
If you’re an entrepreneur, tech enthusiast, or curious about the future of fashion tech and personal styling, this conversation is packed with actionable strategies, inspiration, and behind-the-scenes insights.
🎙️ The Necessary Entrepreneur, hosted by Mark Perkins, features authentic conversations with founders and leaders who’ve built businesses worth studying.
📌 Connect With
Us:
Website: https://www.thenecessaryentrepreneur.com/
YouTube: https://www.youtube.com/@thenecessaryentrepreneur
Instagram: https://www.instagram.com/thenecessaryentrepreneur/
Facebook: https://www.facebook.com/TheNecessaryEntrepreneurPod
X (Formerly Twitter): https://twitter.com/MPerkinsTNE
LinkedIn: https://www.linkedin.com/company/tnepod/
TikTok: https://www.tiktok.com/@tneclips
Spotify: https://open.spotify.com/show/6xhGUE1yzy2N0AemUOlJPx?si=d1c5c316af404f15
Apple Podcasts: https://podcasts.apple.com/no/podcast/the-necessary-entrepreneur/id1547181167
📌 Find Out More About
Taelor
Taelor: https://taelor.style
Taelor Linkedin: https://www.
Taelor IG: @taelor.style
Taelor Facebook: https://www.
Taelor X (Twitter): @TaelorStyle
Anya Linkedin: https://www.
Anya X (Twitter): @Anyacheng
Anya Facebook: https://www.
Anya IG: @anyacheng_siliconvalley
Experience effortless style with rental and personal styling services:
-
Taelor: Get 25% OFF your first month of men's clothing subscription.
Use code: PODCAST25
Sign up at: https://taelor.style/pages/membership -
Armoire: Get 50% OFF your first month of women's clothing subscription.
Use code: ArmoirexTaelor
Sign up at: https://www.armoire.style/refer/ArmoirexTaelor
Give the gift of time, convenience, and effortless style:
-
Taelor Gift Cards: Get 10% OFF
Use code: PODCASTGIFT
Purchase at: https://taelor.style/products/menswear-rental-gift-card