1556: This AI Founder Is Changing How You Get Dressed w/ Sebastian De Castro

1556: This AI Founder Is Changing How You Get Dressed w/ Sebastian De Castro

September 1, 2026 · 32 min

About this episode

Sebastian De Castro discusses how he turned his passion into a scalable AI-powered personal styling business.

Ever wonder how to take a personal passion and turn it into a high-tech, scalable business? Sebastian De Castro, founder of AI-powered personal stylist AskTailr, did just that, taking the entrepreneurial leap to solve a problem he was obsessed with. This episode is a masterclass in making the entrepreneurial leap, bootstrapping a startup with intention, and building a product that solves a real, recurring customer problem. Sebastian shares his methodical, evidence-based approach to product de...

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