How AI is Changing Fashion with Anya Cheng

What this episode covers

What if your wardrobe could work as smart as your phone?In this episode, I sit down with Anya Cheng, the Founder & CEO of Taelor, a leading men’s clothing subscription service powered by AI that combines personal styling with curated rentals.Anya shares how Taelor is helping men dress for success—whether it’s landing a job interview, showing up confident on a date, or making a strong impression in a big presentation.Before launching Taelor, Anya led digital innovation teams at Meta, eBay, Target, and McDonald’s, and was named a Girls in Tech 40 Under 40 honoree.We dive into:How AI is transforming the fashion industryWhy confidence and clothing go hand in handLessons from leading global eCommerce and tech teamsThe future of styling, rentals, and personalized fashionIf you’re interested in entrepreneurship, AI, or the business of fashion, this conversation will inspire you to think differently about what you wear—and why it matters.

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Frequently Asked Questions

How long is this episode of Pro Series with Eric Dillman?

This episode is 22 minutes long.

When was this Pro Series with Eric Dillman episode published?

This episode was published on August 23, 2025.

What is this episode about?

What if your wardrobe could work as smart as your phone?In this episode, I sit down with Anya Cheng, the Founder & CEO of Taelor, a leading men’s clothing subscription service powered by AI that combines personal styling with curated rentals.Anya...

Can I download this Pro Series with Eric Dillman episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.