In this episode of Right About Now, Ryan Alford talks with Anya Cheng, founder and CEO of Taelor, about building an AI-powered personal styling business for busy professionals who want to look better without spending more time shopping. Anya explains how her experience at Meta, eBay, McDonald’s, and Target shaped the way she thinks about product-market fit, branding, and one of the most important lessons in building anything: solve the right problem first.
The conversation then moves into what makes Taelor different, from the subscription model and human-plus-AI styling workflow to the company’s use of customer preference data, stylist knowledge, and forward-looking trend information from partner brands. Ryan keeps the discussion grounded in business reality, while Anya makes the case that the future of AI businesses will not be about who has access to the biggest model, but who has the most useful and defensible data.
They also get into branding versus performance marketing, how ChatGPT is reshaping SEO, why social commerce and live shopping are still early in the U.S., and what founders should understand about building in the AI era. It is a practical episode for operators, marketers, and founders who want to understand where AI creates real business value and where the hype stops.
*Topics Covered*

* Why solving the right problem matters more than building the flashiest solution
* How Taelor combines AI, human stylists, and subscription commerce
* Why brand still matters in a performance-driven world
* How ChatGPT is changing SEO and content strategy
* Why unique data is the real AI moat
* What founders should understand about building AI companies now
* Why everyday convenience may matter more than fashion itself
* Ryan Alford and Anya Cheng on product-market fit, style, and AI business models

Links
Right About Now
https://www.ryanisright.com/ (https://www.ryanisright.com/)
https://podcasts.apple.com/us/podcast/right-about-now-legendary-business-advice/id1346054199 (https://podcasts.apple.com/us/podcast/right-about-now-legendary-business-advice/id1346054199)
https://www.youtube.com/@RightAboutNowwithRyanAlford
Ryan Alford
https://www.ryanalford.com/https://www.instagram.com/ryanalford/
Anya Cheng / Taelor
https://taelor.style/ (https://www.linkedin.com/in/anyacheng/?utm_source=chatgpt.com)https://www.linkedin.com/in/anyacheng/