#268 Busy professionals want to look sharp but hate shopping — so what if AI could handle it for you? In this episode hosted by Kirsten Tyrrel, Anya Cheng, founder of Taelor, shares how she built an AI-powered styling service that eliminates decision fatigue for men who want to dress well without the hassle. Anya dives into her transition from corporate leadership at Meta, eBay, and Target to launching a startup, the unexpected ways she leveraged partnerships to grow, and how a service-based mindset helped her secure funding. She also gets real about the highs and lows of entrepreneurship, proving that success isn’t just about innovation — it’s about persistence. Plus, don’t miss a special listener discount to try Taelor for yourself!

+ The inspiration behind Taelor – AI-powered styling for men

+ From corporate to startup – Anya’s journey from Meta, eBay, and Target

+ AI in fashion – Reducing decision fatigue with smart styling

+ Startup challenges – Bootstrapping, funding, and unexpected hurdles

+ Strategic partnerships – Growth through dating apps, schools, and brands

+ Fashion sustainability – Reducing waste and extending clothing life

+ Knowing your customer – Solving real problems with a niche focus

+ Funding and investors – How Anya secured a $1M investment

+ Lessons in resilience – The reality of startup life

Check out Taelor at Taelor.style.

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