The Entrepreneur Helping People Achieve Their Goals Through Fashion with Anya Cheng

Doug interviews Anya Cheng, who went from unemployed during the 2008 recession to building Taelor Style, an AI-powered men's sustainable fashion company. Anya shares how she ambushed hiring managers outside buildings, called newspaper publishers from phone booths and leveraged her reporter background to land her first job. Anya reveals her framework for persistence, explains how she identified the massive waste problem in fashion and discusses her mission to help busy men look great while solving sustainability issues. KEY TAKEAWAYS • Anya applied her journalism background to ambush hiring managers and call publishers, turning her existing expertise into a job search advantage • After months of networking, she interviewed salon owners and advertisers to create a proposal that landed her first contractor role • Working at Meta and eBay, Anya realised she wanted to look professional without owning or maintaining extensive wardrobes, this is how she identified the fashion rental market gap • Anya built partnerships around customer life moments, targeting dating sites, fitness centres and companies where people need to look their best during transitions. • By genuinely helping another founder and referring clients without expecting anything back, Anya gained access to other investors • Anya combines AI efficiency with human expertise. Her model uses artificial intelligence for initial styling, while human stylists provide final quality control and personal consultation. BEST MOMENTS "Anyone who has a goal shouldn't be worried about how they look. They should focus on their goal when they go on dates." "So many times opportunities there when you are not looking for, many times the curiosity will leave something surprisingly useful." "In half an hour. We have, we got a million dollar investment." ABOUT THE GUEST Anya Cheng is the Founder & CEO of Taelor, an AI-powered men's clothing subscription service promoting sustainable fashion. A Silicon Valley entrepreneur, she has been recognised among "Girls in Tech 40 Under 40" for her expertise in tech product management and marketing. Anya played a pivotal role in launching Facebook and Instagram Shopping at Meta, led new business expansion at eBay, and helped grow McDonald’s global food delivery. She also shaped Target’s mobile commerce and has led teams in AI, product management, UX, and marketing across Fortune 500 companies. taelor.style Facebook Group: https://www.facebook.com/AnyaChengSiliconValley/ Linkedin Profile: https://www.linkedin.com/in/anyacheng/ VALUABLE RESOURCES Website: http://dougbennett.co.uk/ Email: [email protected] LinkedIn: https://www.linkedin.com/in/financialdoug/ Twitter: https://twitter.com/FinancialDoug Facebook Wealth Tribe: https://join.dougbennett.co.uk/ Download Your "Ten-Step Guide To Financial Freedom" Here: https://bit.ly/Struggle-Success BOOKS: Goals Do Come True is now live and available to buy on Amazon: https://amzn.to/3phcy6Z Think Simple, Win Big is now live and available to buy on Amazon: https://www.amazon.co.uk/Think-Simple-Win-Big-Business/ Enjoy, and come back for the latest podcast each Wednesday. Thank you for listening.