How AI Is Changing the Future of Fashion and Sustainability ft. Anya Cheng | TKG Podcast #281
Release Date: 12/13/2025
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Most people complain about the game. Operators learn the rules, build leverage, and surround themselves with better rooms. This episode is that conversation. This episode is part of The Kronos Group Podcast, where experienced operators and founders share real-world lessons on building, scaling, and protecting their businesses. Have an idea for a podcast, but don't know where or how to even start one? PodMatch is your one-stop shop. Use our affiliate link here to start your podcasting journey today - If you're an entrepreneur, founder, or someone wanting to make a change in their life and...
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info_outlineWhat if you could stop wasting time shopping, stop doing laundry, and still look incredible every day?
This week on The Kronos Group Podcast, Jerry Brazie sits down with Anya Cheng, the founder and CEO of Taelor Style — an AI-powered menswear rental and styling service changing the way busy men dress. Anya and Jerry dive deep into:
- How Taelor Style uses AI to predict fashion preferences and eliminate overproduction
- The real story behind building a startup from the ground up (and the truth about imposter syndrome)
- The future of fashion, tech, and entrepreneurship in the AI era
It’s an inspiring look at grit, innovation, and the mindset needed to build something that matters. If you’re a business owner or entrepreneur looking to grow, scale, or find real accountability in your journey, The Kronos Group was built for you.
Join our network of leaders, operators, and founders who are working together to solve real business problems, share hard-earned lessons, and build stronger companies. Learn more or apply to join at www.thekronosgroup.org
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 recognized 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, e-commerce product management, and marketing across Fortune 500 companies.
Anya’s award-winning venture, Taelor AI, was named one of the Bay Area’s Most Innovative Startups to Watch by Business Journal and is backed by early investors in NVIDIA, TikTok, Facebook, Lyft, and Spotify. Anya’s work has earned her 30+ prestigious tech and marketing awards. A best-selling author and two-time TEDx speaker, she teaches at Northwestern University and is a popular keynote speaker worldwide. She holds a Master’s in Integrated Marketing Communications from Northwestern University and an MBA from the University of Chicago Booth School of Business.
Learn more: https://www.taelor.style
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