What if looking sharp didn’t mean shopping or doing laundry ever again? In this inspiring episode, Nell sits down with Anya Cheng — former Meta, eBay, and McDonald’s tech exec turned founder of Taelor, an AI-powered menswear rental startup shaking up fashion, sustainability, and the way we show up in life. From sleeping on couches to landing meetings with CEOs, Anya’s entrepreneurial journey is as bold as her mission: to help busy men look good without the hassle. Packed with real talk on AI, burnout, and building with purpose — this one’s not just for founders, it's for anyone chasing impact with style.

Timestamps:

00:53 – Anya's mission: Helping men look good with AI styling

01:59 – Her wild journey into tech from Taiwan to the U.S.

03:50 – Creating her first product role without knowing what “contractor” meant

05:45 – Why she started a menswear company — and why it's personal

07:58 – The big aha moment about fashion for people who don’t love fashion

10:05 – How Taelor uses AI to style busy men

12:32 – Breaking myths about AI in consumer products

16:03 – Lessons from Meta, eBay & Target applied to startups

20:52 – Growing a startup with no marketing budget

24:25 – Advice for non-tech founders on integrating technology

29:05 – Why Taelor is not expanding to women’s fashion — and what they’re doing instead

30:49 – Burnout & mindset: How Anya stays grounded as a founder

33:24 – Defining success: One outfit, one person, one goal at a time

36:00 – The real story behind a champagne-in-business-class photo

43:14 – How to try Taelor + exclusive discount for listeners

Connect with Anya:

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: 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

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