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WillPower PodcastAuthor: Will T Holdren
Introducing the WillPower podcast, hosted by a young author and accredited businessman, Will Holdren. Each week, he sits down with some of the top entrepreneurs in the industry to discuss their journey to success, the challenges they faced, and the insights they've gained along the way. From startups to Fortune 500 companies, Will delves into the stories of entrepreneurs who have made a significant impact in their field. Join him as he explores the mindset, strategies, and experiences of the most successful business leaders of our time. Language: en Genres: Business, Entrepreneurship Contact email: Get it Feed URL: Get it iTunes ID: Get it Trailer: |
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Ep. 260: From Big Tech to Big Fashion: Anya Cheng on Building Taelor
Episode 260
Monday, 17 August, 2026
On this episode of the WillPower Podcast, Will sits down with co-host Rick Segal and special guest Anya Cheng, Founder & CEO of Taelor, an AI-powered clothing subscription service reimagining how men shop for and wear clothes. Before launching Taelor, Anya spent over a decade in Silicon Valley leading product and growth at companies like Meta, eBay, Target, and McDonald's — including a pivotal role in building Facebook and Instagram Shopping.Anya shares her journey from corporate tech leadership to startup founder, the story behind Taelor's AI-driven approach to personal styling and sustainable fashion, and what she's learned building a company at the intersection of AI, data, and consumer behavior. We also dig into the unique challenges of being a female founder in tech, and how Anya thinks about the future of AI-powered personalization.Whether you're into startups, AI, fashion tech, or entrepreneurship stories, this conversation is packed with insight from someone who's built at scale — both inside big tech and out on her own.Get your copy of Rick Segal's book, The Heart of It here: https://amplifypublishinggroup.com/product/nonfiction/business-and-finance/entrepreneurship/the-heart-of-it/Read Rick Segal’s blog: https://impactinvestorsegal.com/blog
