How to Get Your Business Recommended by ChatGPT, Claude and Other AI Search Tools

Kayvon Kay0:0010,000,000 impressions from ChatGPT. $0 in ad spend. That's not a typo. That's what today's guest pulled off, and it won her campaign of the year from the American Marketing Association. Anya Chang spent her career leading product at Meta and eBay. Then she walked away and built Taylor, an AI styling company that dresses busy men so they can get the job, get the date, and close the deal. But here's why this episode matters to you. Anya cracked the new search game. People aren't googling anymore. They're asking AI, and she figured out how to make her company the answer. If you're building a brand, selling anything, or wondering why your traffic is drying up, this is the playbook. Let's unlock it.

Kayvon Kay0:59Anya, welcome to the show. I I'm excited to have you. I I think what you're doing is amazing. So just for for the listeners here, today is a little different episode here. Today today is not about what you're doing in your business or how you're doing it in your marketing. Today is how you show up. How are you looking when you're going into the meetings? How are you dressing? Anya has created what I think is a phenomenal opportunity for people to be able to get onto a subscription and wear high designer fashion at half the fraction of the cost. So Anya, all the way from the Silicon Valley, working with AI companies and and startups, stepped out and created tailor.ai. Tell us all about that, Anya.

Anya Cheng1:43Yeah. So at Tailor, we help people to look great without doing shopping or laundry. And how how does it work is that we offer AI stylists for people and then send people real clothes for them to rent. So we'll say the unfortunately, you are in Vancouver, but anyone in The US, we when people signed up, pay a monthly fee, and we send them real clothes for them to rent. And after renting the clothes, they can decide if they want to buy it or just simply wear for a couple weeks. Say you travel to New York, you can change your address to New York's hotel so the clothes arrive in the hotel whole weeks that you can look great. And once you're done, return the dirty clothes into a prepaid envelope, give it to a hotel lobby, you can go home without doing any laundry. So no more shopping or laundry. I

Kayvon Kay2:34love the concept, and I just wanna make sure people understand this. This is basically, you can rent high fashion. I when we talk about high fashion, we say, like, it was medium to high, I believe. It's high quality.

Anya Cheng2:48It may not be high fashion because sometimes high fashion, they are fashionable but may not be high quality. So our we offer only high quality brands. They might be the most well known brands such as Johnson and Murphy, Bonobo, Marine Leather, and BYOT cuts, or it might be emergent brands that were really cool, that's trendy, or they might be most well known amazing brands in UK, in Canada, in Japan, but not yet available in The US yet. So high quality brands.

Kayvon Kay3:19High quality brands. However, I think it's important to discuss this first is you get on and you get a consultation of your look. So if you're someone who's going through, say, I don't know what my my my vibe is or I'm going through a brand, a new brand change or I'm trying to find a style. I see all these people with cool style. How do I get style? You'll sit with one of your brand consultants. Is that correct? That's right. So we have a few human stylists

Anya Cheng3:50behind, and then behind their, their workflow, there was there is obviously powerful AI to help those human stylists. But for customer, they interact with a professional stylist who have ten years of experience, and then those stylists to talk to you and figure out what is best for you, like getting a job, getting a day, or close a deal. Most important is for people to about their goals. We help our customer to achieve their goals. For example, we go to a conference. One of our customers, he say, I want to close a deal there. And our stylist decide to send him a dolphin print shirt. He's like, what? Why? Our customers are like, give it a try for conferences all about conversation opener. And he will close, People stop by and say, nice shirt. Interesting shirt. And they start a conversation. And, of course, he closed a deal. And that's what we do to help people achieve their goals.

Kayvon Kay4:47It was very unique in really understanding what it is you're trying to achieve, find the style to adopt to that, and then sending in that the the the clothes and then wearing it and then shipping it back.

Anya Cheng5:00Yeah. It they'll be like, your Uber's ride, you get on Uber, you get off Uber, someone else get on Uber, that your Airbnb rides, you drive you get out of it, you check out with Airbnb, someone else checking. So instead of buying everything, nowadays, we don't buy DVD anymore. We open Netflix show. We watch a show whenever we want to. SS versus ownership, Spotify, we listen to the podcast. We don't record a CD anymore, from the the Vogue on large shows, but then now we can listen anytime we want. So it's the same concept, but then we apply for fashion. So people don't have to store lots of clothes at home, but they always something that they can wear and always looks great and saving time. So I'm I'm always playing skeptic because I'm always thinking about someone who's driving their car right now listening to this podcast. I'm thinking about you,

Kayvon Kay5:56and you're thinking, what in the world? Like, I would never wear used clothes. Or maybe they're thinking, what I was thinking is like, that I'm going to New York next week. And, actually, I'm already thinking about what am I gonna wear. I'm like, I don't wanna wear. I don't wanna pack that. I wanna just pack. I don't wanna do a check-in. But if I have to bring the suit and all this stuff, I gotta check-in the bags, etcetera, etcetera, etcetera. And then you just said, oh, yeah. We can just send it there. What happens when you send the clothes there? I get there, but the clothes don't fit or they don't fit as well. What happens in that scenario?

Anya Cheng6:29Yeah. So if you're really afraid, say you are first time customer, like just use the first time, you can always we can always ship it to your home and you decide you wanna bring to a conference. We are a so usually, if for the first time you are not knowing you enough, sometimes customers say, I'm definitely size million and I think I I weighed two hundred pounds. Turn out that he's not. He can weigh or he lose weight. He doesn't know. Right? Yeah. So if you're really afraid, but if for subscriptions, they tend to we know it right away. After you ran for six clothes and you return, you tell us, oh, you know what? I think I gained weight recently. It's a little bit tight in the belly area. Then we know and the next shipment is better. And for for people on in terms of our secondhand, here's how we think about it. For when you go to restaurant, the spoon that you use probably eaten by a 100 people before. When you go to a hotel, you step on the bed, probably a 100 people step there before. But we all still use those things. And secondhand, we own circular, it's just all over the place. Everywhere now is secondhand. So just more about focus on assets versus ownership, so you don't have to buy everything.

Kayvon Kay7:45Yeah. I I like the idea that it's not just about having to buy everything. It's also about from when we talked is is about changing up the style. It's about being able to wear the clothes for a couple months and then changing the style up and not having to host it and hold it in your closet, you know, for it to collect dust. Yeah.

Anya Cheng8:03Or will you may never like, I personally never like to wear like, buy, like, really wise stuff because I get dirty pretty quickly. And so I know that looks really good, but I don't buy a white shirt. But for in this case, you can rent something or, hey, I never thinks I can wear pink. Oh, but the stylist recommends that, hey, you will be perfect for pink. Give it a try. You only need to wear for a week. You don't have to keep it forever. So why not try something out of comfort zone? Hey, floral shorts is trendy. Hey, pretty short short is trendy now. And those loose, really loose pants, like the jeans are getting really big now. Those back, like, really loose jeans are very The bell bottoms. Yeah. The big bell bottoms. Yeah. So give it a try, which you probably never tried before and you may never like it. But just for a week, now you can try something different, and you might discover you are actually perfect for purple or greens or a certain style that you didn't know that you would fit very well.

Kayvon Kay9:05Let's take a step back here, and let's talk on on the business side of this. Where did you come to the idea of this? Like, what was going on where you thought because this is this is very interesting, and and I and I like it and I could see it. I could see how people would have an affinity towards it. I can also see why people would be scared of it. But how did you come up with this? What came? What was going on in your life that you decided, you know what? This is what the world needs today. Yeah. When I was working for Meta and eBay,

Anya Cheng9:37I came from marketing backgrounds, but I do, over time, became head of product and leading their technology teams, product manager, US design engineers, and technology team globally. So I feel impasse syndrome from time to time. And I'm a woman leader. I'm from Taiwan originally. I'm an immigrant. I'm minority. So I feel like, hey. I need to dress like dress up like who I want to be. No one should find out that I'm freaking out every day. I looks like Dress Lapar, dress for success. So I start looking for some options out there. I look at stitch fix. People pick clothes for you, but you have to buy as soon as you receive the the clothes. And buying is not just about money. It's a lot of Myspaces. How many times am I going to wear this? How do I outfit in this outfit? Can I find somewhere that's cheaper? After you buy the clothes, you do have to do laundry. You do have to do ironings. It's a lot of work. So I started looking for rent home subscriptions such as Nuuly by Urban Outfitters, such as Rent A Runway, Amore. Those are amazing women's rental company here in The US, but they all require me to spend hours to pick. There was a moment that I realized fashion company has designed for people who are into fashion, not for people like me. I just want to get ready for my day and be successful. I don't care what I wear. As long as I get a job, get a date, and close the deal. And I started doing research as a good marketer. We all know, like, researching customer, interviewing your persona, understanding the reach out for the focus group. And I found that a lot of people think like me. They hate shopping. They hate laundry. They are very practical. They have been wearing the same thing last ten years. They opened their closet. They they were only 10 five ten brands, Nike, Lululemon, Banana Republic, and they are all busy men. And that's how Taylor was started.

Kayvon Kay11:42And there you just said something very interesting. They're all busy men.

Anya Cheng11:47That's right. Is

Kayvon Kay11:48tailor more geared for men versus women, or is there a mix? We only need the polite menswear. Oh, I did not know that. Okay. Great. Okay. So this is now I'm getting it. Yeah. So you even have a an ideal market. So this is for the working man that has no time to go shopping, doesn't hates the mall. You don't even start talking about ironing the clothes. Oh my god. So that's that makes a lot more sense. So this is menswear. And for busy, I'm gonna say entrepreneurial c suite, busy men traveling, looking for

Anya Cheng12:24being able to send their clothes, get there, wear them, drop them off, move on with their lives. Yeah. Or a single guy who really not into fashion, but wanna look great. A lot of our customers are sales guy. They are realtor. They know looking good. First impression matters. They only have a few seconds to to get attentions from their clients, customers, but they don't want to wear the same thing again and again. They don't want to think about fashion. They definitely hate to go mall go to the mall, and they love there's a personal stylist on their side. Almost like the gadget guy behind a superhero,

Kayvon Kay13:00just like an executive assistant to helping them out while they don't have to pay premium just like celebrities in those Hollywood. And how how are you attracting the men right now? Like, what type of marketing are you using using and or business tactics are you using for the awareness?

Anya Cheng13:16Yeah. So a lot of our traffic actually coming from Gemini and JGBT. We do very well in AI SEO, AEO, AIO, AGO. So we work with, we manage those things. And for people who may not familiar with that, as you know, people don't always search on internet anymore to ask those AIs to answer the question. And the difference between the AI SEO search engine optimization from before search engine optimization for Google is that you take care a lot more about sentiment. Before it was more about as many keyword as you can put on your website, as many relevant link linking to your site and you rent high. Those were still somehow to be true. But now the AI even care even more about sentiment. So how people say about you on Reddit, how people were reviewing Trustpilot, in Google Map, in Yelp, it become even more valuable. How people say about you were and how how people use you in for context is valuable. Also, Gemini and those they do read more than text. So in the past for Google, you have to put a text of every images and video because Google, those the the scroller bot doesn't read those thing. But nowadays, those AI actually can read videos, so they know the content from your podcast, for example, and those multimedia unstructured data become even more valuable.

Kayvon Kay14:49This has turned into tailored.ai now into marketing SEO, GEO services. So let's dive into that because I think that's super important right now and the game has has changed. And it seems like you figured out the game or you're working the game. So when you started, you you just name you said c you said SEO, you said AIEO, you said GEO. I think you named couple. What were they all? Yeah. I think this is

Anya Cheng15:19the terminology doesn't matter. What's really matter is that people search our ask questions on Churchill BD and Gemini today. Yeah. They don't go in Google. So which you want the JWPD answer whatever question they ask such as, hey, I'm going to New York for conference. What do you think should I wear? You want the answer coming from like Taylor's side, for example, my side. Whereas I don't want them coming from GQ. I want Taylor to be the answer when Chezio PD answer those questions. Right? Because Chezio PD doesn't know the answer. Chezio PD have to go find on the Internet for whoever provide the answer and feed it to the customers and the users. So in our model, for example, we write blog content that's specifically tailored to what people kind of question people will ask through through JWT. So people ask JWT very differently from when they search on Google. In the past, they might say menswear trend 2026. But today, when they go to JWPT, they was like, hey, this, I'm going to this conference. This is a conference. This is I want to close a deal with a client. This is why I'm selling. Tell me what should I wear. They tell a lot more context. Right? So you have to think about what people will be asking them those JISC AI tool, AI search engine, AI chatbot, and come up with an answer that you think will be relevant to the questions. Then you put those questions in, on your website, for example, become blog or you're popular with the bloggers on those.

Kayvon Kay16:54So blogs are still more important than ever, it seems like right now is what I'm hearing. I think the content continue to be important.

Anya Cheng17:04The podcast, the the PR, the blog. However, I think the how how it becomes structure become different. For example, instead of saying that, as a third party's view of, like, fashion the this year, most trendy color, by the way, is is a is a mocha, which is a light brown. And last year was the red wine color maroon. So instead of think about these, you think about, for example, with our fashion stylist to write to write something which we say is actually from the stylist with stylist point of view, it become much more relevant nowadays. And that's how we were able to one, American Marketing Association. Last year, we were the best campaign of the year because we get 10,000,000 impressions from ChatGPT without spending any money.

Kayvon Kay18:00Wow. This is amazing. I didn't even know that we're gonna go down this road. So you guys got a big award because you guys figured out how to get the most impressions from ChatGPT. I'm just trying to reverse engineer. Right? So the the whole point of the podcast, right, is to figure out what's that one thing. If, see, people are listening here, I wanna give them this one thing, and we're gonna get to this one thing. And right now, what I'm hearing is there's a way to win the GPT game so that you show up. And if you do that enough, you should start getting awards. You start getting recognized. And what I'm hearing from you is being you said the sentiment. You said in relevance. So and then I'm also thinking, is there are backlinks still a thing? Are people are backlinks very important?

Anya Cheng18:48I I think it's less important than before, but it's still a component of search engine optimizing because Che GPD today is still calling Google. So whatever you bring high on Google still fit into CheetahGPT. You just on top of what's in the past, they are more stuff. And also, whatever information is proprietary become even more important. I will give you an example. How how do we, get one award was that we start with what people will ask, and then we put together some of the answer and the questions from marketer. We ask our human stylist. They provide a point of view on those answer, which you couldn't find it on the Internet, which you bring our proprietary data. But then from those answer, we use augmented with AI. So AI feed in more information, become those amazing content, which you could be putting on our product detail page. Or you see this shirt, you should pair this shirt with the other shirt, and then you link to the blog page with internal linking from these white shirts, you link to this blog talking about how to wear white shirt but not boring. And and then we send this information when customers are renting clothes, we send the styling notes So then when they open their package of his rental clothes, you also say, hey, mister Key, wear these with these another brown shoes. You will be perfect for day night. But if you don't wanna go to day night, want a more casual, white sneaker is your perfect bet. So you also have this information and customer provide feedback. Feedback of the clothes, customer buy the clothes, where customer browsing on the site, who haven't signed up, they also click around and read the information. And all of those information feedback to the AI again, so the AI generating better content and our human styles are revising again. So it's a it's a flywheel that is human AI, human AI, human AI, and that's how we were able to make this amazing content that include proprietary data and also attract a lot of impressions from Gemini and Tragedy PT. So you're doing the heat maps. What I'm hearing is you you got the heat maps going on the web website. The AI is looking at the heat maps, looking at where people are going, and then getting smarter as it creates more of that content

Kayvon Kay21:09and answering more of those questions because it's pulling the questions off of the placement of where people are going on your website, but also the actual live human feedback that's coming even off website. Like, actually, when they get get the packages, they they're giving back your feedback. So basically, taking the feedback of all your customers and just keep asking the questions and having AI get smarter and smarter. That's right. And these become incredibly

Anya Cheng21:32important. And so one concept that you should know in the era of AI, data is a goal because AI only grow with proprietary data. If you don't have a proprietary data, which means whatever you're using through Gemini or ChurchGPT, you can still do a great job for productivity, but it's going to be unlikely that you become a true AI native company. But nowadays become more valuable with the data. For example, Mr. P interviewing hundreds of people. So you have a lot of insight on how to be a successful marketer. And that's something that other people don't know only mostly you know, and you also have additional point of view from those conversation with a guest. And that's something that cannot easily find on the internet. And they become gold today. So for example, after people renting clothes, they tend to give us feedback. After we rent the clothes, we tend to know the real quality after washes. Okay. Renting three times, second button fall off. So we know those feedback, then we make AI model and agents again and become a tool for fashion brand to predict what's going to sell. And they become our proprietary data and allow us to be an AI native company.

Kayvon Kay22:51Yeah. So your data the data, it's all in the data is what you're saying. And you're collecting the data points. The AI is making the recommendations and really looking at the data quicker and faster than any human can and creating more outputs and opportunities from that data. So you end end up you're gonna end up being a data company versus

Anya Cheng23:13That's right. That's right. Tailored dot AI. That's right. Today, 40% of close goes to unsold. So it's, $40,000,000,000 in The US today of the clothes for menswear actually unsold every year. So we have found that our data insights can really help fashion brand. Imagine you are a fashion designer. You are designing something that's supposed to be twenty two years from today. Imagine you are a wholesale buyer. You have to buy, like, $400,000,000 of the clothes, and all you have was last year's sales number. And as you know, what's trending in fashion last year is It's not trending. Opposite for next year. It almost like predicting tomorrow's weather based on yesterday's weather. Right? So, how we were able to do is we found this amazing insight from the customer can help solve the industry problem and also reduce the future waste from those brands.

Kayvon Kay24:08You just said a static. 40% of the clothes at the end of year go to waste?

Anya Cheng24:15Yeah. In the world today. And then 30% of the clothes in the world actually goes to landfill. It's Nowhere in the sorry. In the world. Yeah. Most of our brand only have sales through rate between 20 to 80%, which means on average, 40% will end up unsold. And those clothes that end up in a landfill, usually get burned, and then you generate 8% of carbon emissions.

Kayvon Kay24:39Wow. I did not know that. 40% of the clothes that you go searching through in a mall, let's just say, on a rack, will end up 40% of it on average ends up in the landfill being burned. That's right. That's right. So it's a lot of waste. It's a real problem in the industry,

Anya Cheng24:58not to mention even for people after buy the clothes and they go home. Most of people only wear less than 20% of what they have in their closet. You just love the few shorts. You always think that one day I wear the less skinny jeans that I bought five years ago, which you never do. And by the end of the day, you feel like, okay, I'm going to give it to pool and donate somewhere. Most of the interest end up in the landfill again.

Kayvon Kay25:23The the donations end up in the landfill as well. So that's what you're trying to you're so Tailor dot a I is not just becoming the fastest growing data company around fashion and clothing. You're also actually doing one step better in helping the world become a better place and an emissions free place is what I Yeah. Believe the real, weird data is valuable.

Anya Cheng25:48Think about this. Almost all of the ecommerce, they only know how people buy, but they don't know how people real feedback after they wear the clothes. Right? After I buy the clothes, I don't even know if am I wearing or someone else wear it. How many times I wear it? When I wear it, how do I feel? Oh, the shoulder is a little bit too tight. Feels a little bit itchy after I wash it five times. The it shrink after wash 10 times. You don't know those things. The other thing is that today, if I ask you which brand is mostly sustainable, then you answer based on whoever do most of marketing saying that Around sustainable. Right? Nobody knows. How do you know? Did you actually do a test wash? Like, oh, you can wash 10 times. This one, only wash five times. You don't know that. Oh, we do. As a rental company, we know the true quality of a garment. We know which brand the product is really most sustainable. And we believe those data can help them as well because a lot of them, they don't even know. They outsource it to big manufacturer. They outsource it to small factory. After batches and batches of inventory, they don't even know the true quality or the issues of garments. And that's where we come in. We play the missing feedback loop between the customer's feedback to the brand partners or brand, designers or the wholesalers.

Kayvon Kay27:10And all of this stemmed from a day I I love the quote you said earlier. I it was I don't you basically said, I don't care what I'm wearing. I just wanna wear something that makes me look good. Act as if because I just wanna get the deal done today. That's right. That's right. One day, we have a customer. He say

Anya Cheng27:28we say, hey. How's it going? What's what do you wanna wear next few weeks from our human stylist? And he say, I I I am going court. I'm getting divorced. I wanna fight for my children. I want to get the rights. And so I don't care what I wear as long as I win the case. So that's it. That's his goal. Anything that I wear can close to win a case. We have a customer say, I don't know, but I'm going on date nights tomorrow. So our stylist sent me a blazer. He's like, you know, I'm pretty more like a hot type of person. I'm not always needing blazer. And our stylist said, you know, it's day night. Just bring it. After he walked out of the restaurant at 9PM, the the woman feel a little bit chilly. He put his Yeah. Blazers on the top of her shoulder. I love it. I love it. The next day.

Kayvon Kay28:18Yeah. He got a second date just because of the blazer. This is fascinating for all the men listening right now. If you have a fashion problem or if you wanna make fashion easier for yourself and be able to have, I would say, more options in the closet, this is the place to be. It's taylor.ai. For for any of those listening, like, what are some last words for them of where they can maybe find you, what they need to know about your services, and where they go?

Anya Cheng28:46Yeah. Go on our website, which is taylor.style. It's taelor.style, taylor.style. Use a code podcast 25, podcast 25, p o d c a s t 25, to get 25% off first month's. And Father's Day and Summer is coming, forever birthdays. If you think the guy need a little bit help, wanna look confident, saving time, and give them a gift card, go on hilo. Style with a code podcast gift, podcast gift, then you get 10% off gift card.

Kayvon Kay29:24And we'll make sure we have that all in the show notes. Again, thank you. I know you're you must be really busy on the back end there, so thank you so much for stopping by and letting us know a little bit more about, obviously, what taylor.ai is, but I think there was even more gold here with how we can start thinking about how we show up in the LLMs

Anya Cheng29:44and GPTs and that for our businesses. Yeah. Thank you so much. This is Anya Chen from Taylor.

Kayvon Kay29:50Thank you.