How AI Is Changing Retail, Style, and the Future of Shopping | Anya Cheng
RIGHT ABOUT NOW
How AI Is Changing Retail, Style, and the Future of Shopping | Anya Cheng
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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 operations. Then we layer on top of larger language model, because they grow, we also grow, but we always want to step ahead. But if you are a small business or you'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 right 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 my style, my image. I was about to 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, with AI, everybody has your personal stylists in your fingertips. But in addition, we send people real clothes for you to wear for a couple of days, couple of weeks. No more shopping, no more laundry. Actually, it's rental service. Before starting a company, I helped you Facebook, Instagram, shopping for me. I had a partner for eBay. Also, senior director and McDonald, round their food delivery business. When you are ordering McDonald's from your phone, there was my partner and helped target to build their tech office here in Silicon Valley. Excited to be here today. You really are 40 under 40. I'm gonna tell you what, girls in tech, 40 under 40, she's got to go on. You've been around the block. That's right. I'm also teaching at Northwestern University. I teach marketing and product management here, so excited to share some example in case studies. Anya, 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 at least your business. But let's say 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 then when I was working for big tech companies before. I was a female leaders for big tech company. I came from data scientists and marketing backgrounds, but I did do a large tech knowledge team. So I always feel a little bit impassive of seeing joy. I'm 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 did fix some other subscription boxes out there, but you all have to buy. They do style you, but once you send you the box 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 Netflix show, you don't have to decide. You watch first three minutes, you don't like it, move out, who cares, these subscription tons of options out there, first buy a DVD, you have to really sure. And I didn't like the pressure of a commitment. I started renting clothes, company like newly 500 million revenue in just five years, backed by Urban Law Feater, rent the wrong way 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 hot 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 since I don't know what to pick. And most of fashion companies seems to have the desire 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 for. Before your questions on what did I learn from big tech company, the end up apply here. One thing that I learned really important in big tech companies is always focusing on finding the right problem versus only focusing on figuring out the solution. Because when you are fixing a room problem, no matter how great your solution is, it's going to be wrong. For example, where a target, they thought of the one problem, which is mom, when they go to store, sometimes they forget one thing. Yes. How about we view something, go call 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 features spend six months, lots of money, geofencing, all of a product in the locations in different stores. Eventually, nobody use it. Why? Mom's, they are going to the store to get lost. They like to wander around the store and they have been 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 there. Me time. Solving the right problem is extremely important and that's why we found that these busy men who are nine to fashion, but single guy sells people recruit a 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 us all the right problems, starts there. Anya, before I turn a little bit more to Taylor and some of the specific you get things you guys do with AI, one question for someone is a stoop is yourself on the marketing side. We're in this world now and obviously sales is everything for a company. Where do you fall on the performance marketing versus branding? Do people care about brands anymore? Is it just about, hey, you saw my problem? You got a product. Boom. Don't really care about the brand. For someone like yourself that's in tech, I can easily see you falling into solution sale. This brand still have a place. Yeah, I truly believe so. Example was my old company Sears. Sears as when we were as Sears came on our website actually faster than Amazon. The feature, the performers, every single website content 10 years ago is actually personalized. Not everybody see the same website. Not everybody see the same email. Not everybody see the same ad 15, 15 years ago. Sears was more cutting-edge than eBay. Most people don't believe so, but when I join eBay, I realize so it's so true. However, people don't like the brand. They never really attached to it somehow. It's the great amazing website. There's some product. But then when you don't have a brand, people don't have relevancy to you, right? So, for example, what we found that in our model, people are not really just buying clothes. They are buying the chance to succeed. But we say, man, where are those options? Nobody care. But when I say, hey, I can help you to dress up for your day night, which you don't have to worry about your day night, just focus on the conversation. People buy the service. People use their service. And I can tell you a meta. At one point, they actually do blind testing. They sell the glasses. And at one point, they just put down the height of the glasses. They put like aculars versus other brands on apples and some others. We see people actually choose differently. I do think that if both are equally important, we know the marketing funnel. You don't have a consideration. There's no performers marketing needed. However, it's also if you only have branding, but you don't have performers marketing, you can never convert those awareness in consideration. We recently won the American Marketing Association Award of Excellence in Marketing by doing very well on CHAT GPT. Nowadays, people say, performers marketing more and more get into like CHAT GPT SEO versus Google SEO, because more people ask you questions here. How we do it is that we use human and machines in the loop and exercise. We start with identify the user journey, why people search for something even on CHAT GPT. Identify the question people will ask. We have a human to write down the overall outline. We use AI to generate content. From there, our human style is revising the content with their point of view. And then we when we send the customers off it with a styling note, customer provide feedback, put your feedback into the notes with the content. And then those content generating too automatically to the website, which will get more traffic coming in from CHAT GPT and as regular SEO. And you become automatically fly well. So then we won the award. We got 10,000 impressions for free from there. But I truly still believe brand is important. So does the performance marketing. Woman after my own heart talking about the purchase funnel here. I love talking about purchase funnel. You got awareness, consideration and tint. And then you got to make a purchase. Yo, man, heart beaten. I'm a marketer hard on it. I will say it's really smart what you're doing because people are moving from SEO. Hey, all about all this list. No, just give me the answer. It's about answers about solving the problem. It does lead to a fasting discussion is when there's only one answer. What happens to SEO? Well, let someone else smarter than me. I solve that one. Anya, you just talked a little bit of how you're using AI. It's been at the core of the business. I take it since day one from what I heard and what you described. What's been the biggest learning lesson being on this cutting edge of AI? Europe AI is very different from the era of algorithm. If you look at last generation, Google is a black box of algorithm. What's rent high is important. But nowadays, unless you are Elon Musk, Mark Zuckerbergs, otherwise most of you are going to use open AI to chat with these parent companies where Elon Musk, AI's or Google's AI, etc. So nobody is going to view your own algorithm. Means what? Means data is way more valuable nowadays. Building AI is easy. It's like building website 20 years ago. You need a whole bunch of engineers. Nowadays, you need $10 on Shopify. You're done. Nowadays, the key things that you have, you are unique data. So you can bring your data on top of whatever large language model, the Elon Musk, AI, Mark Zuckerberg, and Taylor. We know customers should preference. Why? If you go to the store, may see it no strong or Amazon, you buy or spy don't buy something largely because of price. Your decision is polluted by the price. But when you watch your Netflix show, the show is not down this scale. You watch which show is you truly like it. The same thing for our membership model. We pay people pay $100 per month. Whatever the clothes they pick along with our AI, that our AI actually picked for them. But when they want to get alert, I'm doing deciding that it's what they truly like. We also get feedback every hour week because the customer wanting to make sure the next shipment is better. Versus in the past when I'm working for Target, when people never give feedback unless it's one star and they're so pissed off about that, right? We all don't know future. AI don't know the future. AI know the past. But we are working with 300 fashion brands. They are designing something for the future next year's trend. But the next year's color, they are designing that. They are deciding that. And we also have human dollars. They have no heart. Why you don't just search. Why you find celebrities still use human dollars because they are still better. We have those unique data. We put it together and we buy two companies, the astounding information from their 10 years operations. Then we lay on top of larger language model because they grow. We also grow. But we always once they have a hat. If you are a small business or starting a company, now is your time because building AI is easy. All you need is unique defensive data. For example, my friend is a doctor. She's a dentist. All he does is you just have one like the practice for 15 years. But he has those images for 15 years with different teeth issue. So now he's building his AI to detect teeth issue because he has those images. Those unique data they know what else has. Think about that. And then for your previous questions on the SEO for chat GPT, one thing you should know is that in the past, for Google, they only consider structured data. Miss copies. Remember an image like Google doesn't rewrite as image. But we have to write Ryan right about now show behind that image so that Google can read. However, now a day AI they re-boast. They re-image. They re-video. They re-boast. Multimedia become a lot more important. User-generated content become a lot more important. And there's a difference between SEO nowadays on chat GP versus before. That's good. Hey, I mean, I'm out there, man. I got thousands of episodes and highlight clips and smart people like Anya coming on the show telling us all the good stuff. Hey, we're covered on you. We're good. Exactly. Walk me through. And I'm a busy executive. My wardrobe sucks. Not mine. Munch stylish because I got things like Taylor and other things that I use. But talk to me what that process looks like. Yeah, our customers, they slide up just like Netflix show. They signed up for a membership. $79, $98, however program they pick. So then they can't get to wear like 10 clothes per month, for example. So they start with a simple style quiz. How are AI know about you? We ask you some question. We do ask you your high-end way, which we don't always use because a lot of customers they think they are to learn thinner. They will put that I am definitely size medium. No, no, no, go to your closet. Pick your favorite outfit. Oh my god. When did I become a size lecture large? Yes, you are. I'm 65 to 65. So believe me, I know. It's not mediums in the closet for me. We do also ask them to go to their closet and look at their favorite outfit. What size is it? And then most important question we ask is your purpose. Because our customers, they don't care about looking good. They care about looking good so that they get a job, get a day, a closer deal, number one, every single day. They want to get 5 million followers like following and traffic every single episode. That's what they care. They care about success. No matter what's their definition of success. Some people success means more time with their kids so then they don't need to worry about their farmer's outfit, a farm market outfit. Some people success means they close a deal, want a 10 million dollar deal with these new clients. Our job is to make sure we dress up to success to project the best image that you want. And then from there, we ask you to upload a few pictures, you like this life certain item. And if you like, we get a 15-minute consultation call with a human stylist. Our human stylist is good on Zoom call and then we'll talk with you. You can show the closet, your body, or whatever thing you want to show. From there, we send you the first 7 items for example. You already miss a match to multiple outfits that fit with your upcoming schedule. And then from there, if you wear after you wear for whole weeks, if you're traveling, give it back to the hotel lobby with the return envelope that's prepaid. You go home without doing any laundry when you get home. The next day, the new clothes has arrived. So no more shopping, no more laundry like your Netflix show. Subscribe, you can watch a lot of things. So you get to try it, you don't have to buy it. And you get to trade in and out because that you want. And do you get the option to keep it or is it just raining no matter what? You get the option to keep it. And the good thing is that for most of a busy man, they never go to a dress store. So we all know sustainability, buying second-hand sprays, and if they drop it, nobody have those times. So in this model, after you wear it for a few weeks, usually it's high on discounted 10, 20, 50, 70 percent off. So then most of people just buy it. They look still very new, just like your airport rental car. They tend to be very, very new. Every year, branding three times is already so. And we pounded with over a hundred brands, Marie Lear, Johnson and Murphy, Bonobos, all kind of brand you never. For both the most famous American brand, but also we saw school bully, fast-branded Italy, fast-branding in Nath Netherlands, in UK, in Japan. So you get those amazing brands come here and then you can try. I can tell you most of our customer thinks that I will never wear pink. And our stylist, how about this? I give you a bonus item for free. Try this one. And they're like, okay, this is great. Can I buy two of that? So many of us never know our true style because we have been wearing the same thing again in the last 10 years. Real man wear pink. I like it. I love this because you get to try stuff. You just hit the nail on the head. You try stuff that maybe you wouldn't feel comfortable buying. And you know, you're not stuck if you don't like it. But a lot of times it forces you into trying something a little different and you could sample it. And then you get to at least expand your horizons of what you might wear. I'm a black t-shirt guy. I come back to the black v-neck a lot, but I've had to expand the palette. My wife's like, all right, black v-necks. It's time to take a little break and gotta have a little splash of color. That's right. Most of them don't. We ask like, what color you usually wear blue? Everybody's blue. And the good thing you don't have to know, our humans tell us without AI will appear for you. We even tell you, okay, what shoes you should pair with, what bells you should pair with. And that's the way we are expanding into as well. Our customer uses more like exactly a system, can see at your service or more like the gadget I'd be hiding superhero in those movies. So you ask questions about branding and what we are really selling. I think we are not really just selling clothes. We are selling the piece of my, the convenience, the chance to succeed. And that's what our customers are really buying for. That makes a lot of sense. What about like, okay, tuxedos or, so I think it's not you think of rentals and you think of suits or something. Is this a service to use for those types of single one-off events? No, not at all. Our customers, we don't have suits. We don't have a tuxedos because most people don't wear their nowadays. We have blazers, sport coats, we have t-shirts, booties, swathes and all kind of things. And for everyday wear, our mission is to help people get ready for their days. So our customer uses more like your Netflix show. In the old time, you buy the DVD once a year, like, okay, how are they? We will do this. But nowadays, you open your Netflix show. You become everyday. In the old time, you only rent the car once a year when go on the road trip is your family. Nowadays, you open ubers and love. You rent the car every single day. With a luxury economy, it's getting a lot more, it's getting into everyday life. And also, we ponder with fashion brands that fall over the world. So instead of burning those inventory, today, 30% of the clothes go directly from factory to landfill, generating 10% of carbon emissions, 20% of polluted water, fashion is the most polluted industry in the world. Instead of burning those inventory, we also help them to find a new outlet. And also, a lot of brands send us the latest collections. Over a hundred brands, we ponder with a lot of them. They will be sending testing their latest collections through the platform. Then they get feedback right away. Then they can design for to produce next year. And our customer on the one hand helping to solve the environmental issue on the other hand, become the guinea pig to try the latest collections. It's not even all year. Maybe you are wearing the most trendy shirt for next year. Hey, win, win. Would you wrap up here, Anya? I got a question for you about a trend that's been taken all, especially. And it's a little late and the state's been overseas a lot more. It's what your perspective, live shopping. Where does Anya fall on this? Are you a proponent? You think this is a trend that's going to expand? I personally do, but I'd love to know someone like yourself, what you think about what's happening in the live shopping space. You're asking a right person because I live view live shopping for meta. So, I view live shopping, Instagram, Facebook shopping. I help to build a team. I actually build a live shopping feature for meta. I think for sure it's going to expand. Most people ask me the question differently though. They say ask me why is so slow in the US? As you know, it's been super popular in China, Southeast Asia. Most of the countries, their live shopping is their everyday life. And every year I heard V.C. investors come to me and say, Anya, can you do diligent this company? We really think that it's going to blow up next year, why? But then after few years, still not yet. That's not everywhere yet. I still truly believe it will be very, very popular. But the reason why you haven't been, I think many reason number one. I think in the US, we tend to be a little bit more fragmented in terms of platform, like commerce platform or payment platform. Most of people don't feel comfortable giving Facebook your credit card. While in China, Southeast Asia, many of those companies, their platform for payments is exactly the same platform for their e-commerce. That's where they shop, where they do the payment, where they book appointment for doctor appointments. They are super apt as all of those things. While here, we feel like Amazon's, Amazon's, eBay's, eBay's, Instagram and Google Maps, they are all separate functions. Customer behavior takes a while on being emerged. The other things that I think is also because of talents. If you look at those countries that have very strong live shopping, they are engineers. The same thing, they are engineers who build payments and shopping. Other same people who build chat conversations. While in the US, I can tell you a lot of Google engineers or Facebook engineers in their entire life, they never build anything that was a physical product. Life chattings or other stuff, whatever Google Maps, there's no physical product. So it's very different from the engineer who worked in Amazon. They need to consider the warehouse, the shipping time, the physical product, which is a very, very different user experience technology collecting taxes, collecting, doing returns. Make sure you're right on time. We live time in the offline environment. So also, talents are very, very different. However, despite those things, I still super believe that either commerce company, like Amazon, those companies will incorporate a lot more social into it. I also do believe social company, meta-instagrams and TikTok will still incorporate a lot more commerce in order to pool their attribution, that they actually make an impact for the sales, for advertisers. And I also still do believe that there will be stand-alone commerce, social commerce platform emerge. Today, you see, for example, Sephora, I do see a lot of startups doing just Sephora type of company, but entire side is native from social commerce with social contents over there. So I truly believe that still the future. Yes, what not to take it off. I'll tell you where it's taken off, and there's no looking back, and this trading cards and collectibles. Yes, I have a business in that, and let me tell you, people are hookline and sinker on live shopping. We'll see maybe in Taylor's future, who never knows, but ultimately, they're already breaking the mold using AI. Taylor, work here right, keep up with you and Taylor and learn more. If you are investors, if you are suppliers and were talents, or partner dating side, fitness center, career center, shows who needs office, feel free to reach out to me. I'm Anya, ANYA, and Taylor.ai, that's T-A-E-L-R.ai. Or if you are just customers want to get ready for your day, no more shopping or laundry, always looks great, have human and AI style is to style you. Then go on Taylor.style, that's T-A-E-L-O-R, that's T-Y-L-E, Taylor.style. Use a call, podcast 25, podcast 25 to get 25% of your first months, or use a go on the gift card to go in podcast gift to get 10% of gift card. Love it. Podcast 25 and podcast, is that gift? That's right. There it is. We got those. We'll have those in the show notes for everyone to take advantage of Anya. It's a pleasure to meet you. Nice meeting you, and thanks everyone. Would you all be very successful and saving time? No more laundry. Who say, AI cannot do your laundry? This is Anya from Taylor.style. Thank you. Hey guys, you know to find us, Ryan is right.com. We'll find highlight clips, show notes, and all the links that Anya so graciously shared for savings on Taylor. You know, it's always here. It's always right. It's always now. We'll see you next time. Here's the truth. Information doesn't change your life. Execution does. So don't just listen to this episode and move on. Take the idea. Make the call. Launch the thing. Fix the problem. Build what you keep talking about building. For more, follow Ryan Ulford on Instagram at Ryan Ulford. And watch or listen to every episode at RyanIsRight.com. This is right about now. Now quit waiting. Go win.