Episode Details

She didn't know what entrepreneurship was two years before starting her company.

She grew up in Taiwan, her dad worked in a factory, and when she landed her first U.S. job offer she went home and Googled "contractor" — and genuinely thought they wanted her to be a plumber.

Anya Cheng spent 15 years at Meta, eBay, Target, and McDonald's before launching Taelor AI, a subscription service that uses AI to pick and rent clothes for busy men. She raised $2.3M at a $7M valuation, and her investors now include the YouTube founder, Google Gradient Capital, and Morgan Stanley's managing director.

What she covers:

→ Starting a media club in a Taiwanese high school that banned new clubs — by reading the full handbook and collecting 500+ signatures

→ Arriving in the U.S. barely speaking English and getting rejected from every campus recruiter during the 2008 recession

→ Couch-surfing New York City for two months to network her way into a job — with no money and no contacts

→ Calling a Taiwanese magazine to get free conference access as a "media representative" so she could afford to attend

→ Googling "contractor" after landing her first U.S. job offer and thinking they wanted her to be a plumber

→ Launching Taelor AI with a $10 Shopify site that had nothing on it except an email signup box

→ Ignoring their first customer for a month because she thought he was a scammer — then shipping him clothes from a department store sale

→ Raising $1M from Northwestern and Chicago Booth alumni WhatsApp groups before ever talking to a single VC

→ Getting a warm intro to Bowling Capital through a founder she forgot she was supposed to be networking with

→ Winning a startup competition hosted by Northwestern — held at a University of Chicago event — and using the rivalry to get press coverage

→ That press coverage landed her on a local ABC morning show, which she used to convince a fashion trade publication to run her story, which got her first brand partner

→ Growing from 1 brand partner to 150+ fashion brands (Mizzen+Main, Johnston Murphy, Bonobos, Cuts, Rhone) without buying inventory upfront

→ Selling data back to fashion brands to help them predict demand and cut the $30 billion in unsold clothing that goes to landfill each year

→ Why she rallied "minority investors" after learning only 1.8% of VC funding goes to female founders — and how that strategy built her entire cap table

🔗 CONNECT WITH ANYA CHENG

Website: https://taelor.style

🔗 CONNECT WITH STU

Instagram: @stu

Website: https://startupswithstu.com

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