Right About Now with Ryan Alford - How AI Is Changing Retail, Style, and the Future of Shopping | Anya Cheng

Episode Date: June 16, 2026

Ryan Alford sits down with Anya Cheng, founder and CEO of Taelor, for a conversation about AI, commerce, branding, and why data is becoming the defining advantage in the next generation of startups. Anya shares how she identified a real customer problem inside fashion and style, why most men do not actually want to shop, and how Taelor was built to remove friction through a mix of AI, logistics, and human styling support. Ryan and Anya also dig into the balance between brand and performance marketing, the changing role of SEO in a ChatGPT world, and why founders should be thinking less about building models and more about owning differentiated data. The episode becomes a bigger discussion about business moats, customer behavior, and how the most valuable AI companies may come from industries that do not look flashy at first glance. They close with a sharp look at live shopping, social commerce, and where Anya believes U.S. consumer behavior is headed next. It is a useful listen for entrepreneurs trying to separate what is durable in AI from what is just noise. Topics Covered How Anya Cheng went from major tech companies to founding Taelor Why solving the right problem is more important than building the right feature The role of AI and human stylists in modern commerce Why unique data is more valuable than generic model access Branding, performance marketing, and the purchase funnel ChatGPT SEO and the rise of answer-based discovery Live shopping and why U.S. commerce behavior still lags Asia Ryan Alford and Anya Cheng on defensible AI business strategy Links Right About Now https://www.ryanisright.com/ 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/

We have those unique data. We put it together and we buy two companies their styling information from their 10 years of operations. Then we layer on top of larger language models. Because they grow, we also grow, but we always want step ahead. If you are small business, we're starting a company. Now is your time because building AI is easy. All you need is unique defensive data.

You don't win by following the playbook. You win by rewriting it. 700 episodes deep with the people, who actually built something real. No theory, no fluff, no shortcuts. This is Right About Now with Ryan Alford. What's up guys? Welcome to Write About Now. We're here to help you get right now.

Hey, we can talk about what you should have done. We can talk about what you should do. We need to talk about right now. You know what's right now? It's AI. It's lots of it. It's every day. It's in front of us.

But ultimately, hey, I like to look good. It's hey, my style, my image. That's why I go straight to the source. It is Anya Chang. She is the founder and CEO of Taylor. She's making everybody look good. What's up, Anya? Hello, this is Anya from Taylor AI.

We use AI to pick clothes for you. In the past, only celebrity has human stylists. Nowadays, who is AI, everybody, has your personal status in your fingertips. But in addition, we send people real clothes for you to wear for a couple days, a couple weeks. No more shopping, no more laundry. Actually, it's a rental service. Before starting a company, I help you Facebook, Instagram shopping for META. had a product for eBay, also senior director at McDonald's,

around their food delivery business. When you are ordering McDonald's, from your phone, there was my product, and helped target to build their tech office here in Silicon Valley. Excited to be here today. You really are 40 under 40. I mean, I'll tell you what, girls in tech, 40 under 40. She's got it going on. You've been around the blog.

That's right. I'm also teaching at Northwestern University. I teach marketing and product management there, so excited to share some example in case studies. Anyo, I want to talk mainly in our, short time together about what you're doing with Taylor, how you've grown that business, the future of all AI is related to your business. But let's at least because you do have an impressive background. You've worked, Facebook, you just named the who's who, some tech brands,

and otherwise. What's the one thing that our audience could know about you and what you learned working at some of those giants? And maybe one of the biggest takeaways that then led you to your own path. The reason that I started a company was that when I was working for big tech companies before, As a female leaders for a big tech company, I came from data scientists and marketing background, but I did do large technology teams. So I always feel a little bit impassive syndrome. Am I ready for the day? I'm sure many people like me who have a dream feel that sometimes.

I start feeling like maybe at least I need to look great, dressed up, looks presentable. When I'm freaking out, nobody will find out. I started using some subscription boxes like stitchfix and some other subscription boxes out there, but you all have to buy. They do style you, but once they send you the bots, within a few days, you have to decide if you're going to buy. It's almost like Netflix show versus buying a DVD of Home Alone. If you're watching a Netflix show, you don't have to decide, right? You watch for three minutes.

You don't like it, move on. Who cares? It's subscription, tons of options out there versus buying a DVD you have to really short. And I didn't like the pressure of a commitment. I started renting clothes, a company like newly, 500 million revenue in just five years, or backed by Urban Outfitter, rent a runway, or more,

lots of women's rental company. All of them require me to pick. Hundreds of thousands of garments, pick, pick, pick, spend two hours. And it was a hard moment for me that I realized I do not like browsing and shopping

and I don't know fashion. I don't have strong fashion sense. I don't know what to pick. And most of fashion companies seem to have the design for people who are into fashion. Not for people like me. Just want to get ready for the day

and be successful. And that's what Taylor was born. But for your questions on, what did I learn from big tech company that end up applied here? One thing that I learned really important in big tech company is always focus on finding the right problem versus only focus on figuring out the solution. Because when you are fixing a wrong problem, no matter how great your solution is, it's going to be wrong. For example, where at Target, they thought of the one problem, which is mom when they go to store, sometimes they forget one thing. Yes. How about we build something to go shopping list?

You list the shopping list, you go to the store, the app become an in-store GPS. Turn right, turn left, never forget one thing from the store. The launcher feature spent six months, lots of money, geo-fencing all of the product in the locations in different stores. Eventually, nobody use it. Why? Moms, they are going to the store to get lost. They like to wander around the store. And they have been in store for 10 years.

They said they get away from their noisy kids. They want to be lost in the store so they can buy something and spend time. is there. Me time. Solving the right problem is extremely important. And that's why we found that these busy men who are not into fashion, but single guy, salespeople, recruited faster, professor, really don't care about fashion, but need to look good. And we are solving the problem to help them to be more successful. Smart. Get to solve the right problem that starts there.