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

10 million 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 Tailor, 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.

Anya, welcome to the show. I'm excited to have you. I think what you're doing is amazing. So, just for the listeners here, today is a little different episode here. 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 Silicon Valley, working with AI companies and startups, stepped out and created Tailor.ai. Tell us all about that, Anya.

Yeah, so at Tailor, we help people to look great without doing shopping or laundry. And how does it work is that we offer AI stylists for people and then send people real clothes for them to rent. So, unfortunately, you are in Vancouver, but anyone in the US, 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 hotel lobby. You can go home without doing any laundry. So no more shopping or laundry.

I love the concept. And I just want to make sure people understand this. This is basically, you can rent high fashion. When we talk about high fashion, we say like it was medium to high, I believe.

It's high quality. It 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 John St. Murphy, Bonobo, Marine Layer, and BYOT Cuts, or it might be emerging 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.

High-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 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 behind, and then behind their, their workflow, there is obviously powerful AI to help those human stylists. But for customer, they interact with a professional stylist who have 10 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 date, or close a deal. Most important is for people about their goals. We help our customer to achieve their goals. For example, you 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 say, what? Why? Our customer say, give it a try. For conference, it's all about conversation opener. And he will close. People stop by, say, nice shirt, interesting shirt. And they start a conversation. And of course, he close a deal. And that's what we do to help people achieve their goals.

Was very unique in really understanding what it is you're trying to achieve, find the style to adopt to that, and then sending them that, the clothes, and then wearing it and then shipping it back.

Yeah, it's a little bit like your Uber's, right? You get on Uber, you get off Uber, someone else get on Uber. That your Airbnb rides, you drive to stay, you get out of it, you check out Airbnb, someone else check in. So instead of buying everything, nowadays we don't buy DVD anymore. We open Netflix show, we watch a show whenever we want to. Access versus ownership. Spotify, we listen to the podcast, we don't record a CD anymore, uh, from the, the Vogue Unlocked shows, but then now we can listen anytime we want. So it's the same concept, uh, 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, always looks great and saving time.

So 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 and 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, "I'm going to New York next week." And actually, I'm already thinking about what am I going to wear? I'm like, "I don't want to wear, I don't want to pack that. I want to just pack. I don't want to do a check-in, but if I have to bring the suit and all this stuff, I got to check in the bags." et cetera, et cetera, et cetera. 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?

Yeah. 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 want to bring to a conference. We are a subscription. So usually if it's for the first time, we are not knowing you enough sometimes. Customer say, I'm definitely size medium and I think I weigh £200. Turn out that he's not, he gain weight 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 rent for 6 clothes and you return, you tell us, oh, you know what? I think I gain weight recently, it's a little bit tight in the belly area. Then we know and the next shipment is better. And for people, Uh, on— in terms of on secondhand, here's how we think about it. For when you go to restaurant, the spoon that you use probably eaten by 100 people before. Or you go to hotel, you step on the bed, probably 100 people slept there before. But we all still use those things. And secondhand, pre-owned, circular, it just all over the place. Everywhere now is secondhand. So just more about focus access versus ownership. So you don't have to buy everything.

Yeah, I like the idea that it's not just about having to buy everything. It's also about, from when we talked, 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, or 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 white shirts. But for in this case, you can rent something. Or hey, I never think 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 shirt 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—

bell bottoms. Yeah, the big bell bottoms.

Yeah. So give you 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 were fit very well.

Let'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 very interesting 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, I came from marketing backgrounds, but I do Over time, became head of product and leading their technology teams, product manager, UX/UI designers, and technology team globally. So, I feel imposter 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 up like who I want to be. No one should find out that I'm freaking out every day. I look like Dress the Part, 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 clothes. And buying is not just about money, it's a lot of mind spaces. 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 start looking for rental subscriptions such as Nuuly by Urban Outfitters, such as Rent the Runway, Amore.

Those are amazing women's rental companies here in the US, but they all require me to spend hours to pick. There was an aha moment that I realized fashion companies have 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 a deal. And I start 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 10 years. They open their closet. There were only 5, 10 brands. Nike, Lululemon, Banana Republic, and they are all busy men. And that's how Taylor was started.

And you just said something very interesting. They're all busy men.

That's right.

Is Taylor more geared for men versus women, or is there a mix?

We only provide menswear.

Oh, I did not know that. Okay, great. Okay, so this is— now I'm getting it. Yeah. So you even have an ideal market. So this is for the working man that has no time to go shopping, doesn't hate 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 going to say entrepreneurial C-suite, busy men traveling, looking for being able to send their clothes, get there, wear them, drop them off, move on with their lives.

Yeah, or single guy who really not into fashion but want to 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 get attention 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, just 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 and/or business tactics are you using for the awareness?

Yeah, so a lot of our traffic actually coming from Gemini and ChatGPT. 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. They 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 it care a lot more about sentiment. Before it was more about as many keywords as you can put on your website, as many relevant link linking to your site, then you rank 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 on Trustpilot, in Google Maps, in Yelp, it become even more valuable. How people say about you and how people use you in what context is valuable. Also Gemini and those ChatGPT, they do read more than text. So in the past for Google, you have to put the text of every images and video because Google, those, the, the scroller bot doesn't read those things.

While nowadays those AI actually can read video. So they know the content from your podcast, for example, and those multimedia unstructured data become even more valuable.

This has turned into, uh, Tailor.ai now into marketing, SEO, GEO services. So. So let's dive into that because I think that's super important right now and the game has changed and it seems like you figured out the game or you're working the game. So when you started, you just named, you said SEO, you said AIO, you said GEO, I think you named a couple. What were they all?

Yeah, I think the terminology doesn't matter. What really matters is that people search. Our ask questions on ChatGPT and Gemini today.

Yeah.

They don't go in Google. So which you want the ChatGPT 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, versus I don't want them coming from GQ. I want Taylor to be the answer when ChatGPT answer those questions, right? Because ChatGPT doesn't know the answer. ChatGPT 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 kind of question people will ask through ChatGPT. So people ask ChatGPT very differently from when they search on Google. In the past, they might say, menswear trend 2026. But today, when they go to ChatGPT, they will say, hey, Lisa, I'm going to this conference. This is the conference. This is— I want to close a deal with a client.

This is what 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, those AI tool, AI search engine, AI chatbots, and come out with an answer that you think will be relevant to their questions. Then you put those questions in, uh, on your website, for example, Bland, but become blog, or you partner with bloggers on those.

So blogs are still more important than ever, it seems like right now is what I'm hearing.

I think the content continues to be important. The podcast, the PR, the blog. However, I think how it becomes structured becomes different. For example, instead of saying that as a third party's view of like fashion, this year most trendy color, by the way, is 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 something which we say it's actually from the stylist, with stylist point of view, it become much more relevant nowadays. And that's how we were able to won American Marketing Association. Last year we were the best campaign of the year because we get 10 million impressions from ChatGPT without spend any money.

Wow, this is amazing. I didn't even know that we're going to 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 want to give them this one thing and we're going to 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 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 backlinks still a thing? Are people— are backlinks very important?

I think it's less important than before, but it's still a component of search engine optimizing because ChatGPT today is still calling Google. So whatever you rank high on Google still fits into ChatGPT. It's just on top of what's in the past, there are more stuff and Also, whatever information is proprietary becomes even more important. I will give you an example. How do we get won the award was that we start with what people will ask. And then we put together some of the answers and the questions from marketers. We ask our human stylists. They provide a point of view on those answers, which you couldn't find it on the internet, which would bring our proprietary data. But then from those answers, we use augmented with AI. So AI feeds more information. Become those amazing content which could be put on our product detail page. When you see this shirt, you should pair this shirt with the other shirt, and then it link to the blog page with internal linking from these white shirts. It 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 with rental clothes, you also say, hey, Mr. Wear these with these another brown shoes, it will be perfect for date night. But if you don't want to go to date night, want a more casual, uh, white sneaker is your perfect bet. So you also have this information and customer provide feedback, feedback of the clothes, customer buy the clothes, or 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 stylist 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 these amazing content that include proprietary data and also attract a lot of impression from Gemini and ChatGPT.

So you're doing the heat maps. What I'm hearing is you, you got the heat maps going on the website. The AI's looking at the heat maps, looking at where people are going, and then getting smarter as it creates more of that content. And 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 the packages, 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 important. And so one concept that you should know in the era of AI data is a goal because AI only grows with proprietary data. If you don't have proprietary data, which means whatever you're using through Gemini or ChatGPT, 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, it becomes more valuable with proprietary data. For example, Mr. Key interviewing hundreds of people. So you have a lot of insight on how to be a successful marketer. And that's something that other a lot of people don't know, only mostly you know, and you also have additional points 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 3 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.

Yeah. 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's 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 up— you're going to end up being a data company versus—

that's right, that's right. Today, 40% of clothes goes to unsold. So it's, uh, $40 billion 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 brands. Imagine you are a fashion designer, you are designing something they're supposed to be trending 2 years from today. Imagine you are wholesale buyer, you have to buy, place $400 million of clothes, and all you have was last year's sales number. And as you know, what's trending in fashion last year is not trending. It's the opposite. It's almost like predicting tomorrow's weather based on yesterday's weather, right? So how we were able to do it is we found this amazing insight from the customer can help solve the industry problem and also reduce reuse the future waste from those brands.

I— you just said a stat, like 40% of the clothes at the end of year go to waste?

Yeah, in the world today. And then 30% of the clothes in the world actually goes to landfill.

Do you know where in the— sorry, in the world?

Yeah, most of a brand only have sales-through rate between 20 to 80%, which means on average 40% will end up on sale. And those clothes that end up in the landfill usually get burned, and then you generate of carbon emissions. Wow.

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. Not to mention, even for people after buying the clothes and they go home, most people only wear less than 20% of what they have in their closet. You just love a few shirts. You always think that one day I wear the, that skinny jean that I bought 5 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 them just end up in the landfill again.

The donations end up in the landfill as well. So that's what you're trying to— you're— so Tailored.ai 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.

Yeah, we believe the real wear data is valuable. Think about this. Almost all of the e-commerce, they only know what people buy, but they don't know what 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. Feel this, it's a little bit itchy after I wash 5 times, it shrinks 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 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 5 times. You don't know that, but 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 create the missing feedback loop. Between the customer's feedback to the brand partners or brand designers or the wholesalers.

And all of this stemmed from a day— I love the quote you said earlier. It was, I don't— you basically said, I don't care what I'm wearing. I just want to wear something that makes me look good, act as if, because I just want to get the deal done today.

That's right. That's right. One day we have a customer, he say, We said, hey, how's it going? What do you want to wear next few weeks? From our human stylist. And he said, I am going court, I'm getting divorced, I want to 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, 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 hot type of person. I'm not always needing blazer. And our stylist said, you know, it's date night, just bring it. After he walked out the restaurant at 9 PM, the woman feel a little bit chilly. He put the blazers on the top of the shoulder.

I love it. I love it.

The next day.

Yeah, he got a second date just because the blazer. This is fascinating for all the men listening right now. If you have a fashion problem or if you want to 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 Tailored.ai. 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?

Yeah, go on our website, which is tailored.style. T-a-e-l-o-r.st-y-l-e, Taylor.style. Use the code podcast25, podcast25, P-O-D-C-A-S-T-25, to get 25% off first month. And Father's Day and summer is coming, for every birthdays, if you think the guy need a little bit help, want to look confident, saving time, and give them a gift card, Go on taylore.style with a code podcastgift, podcastgift, then you get 10% off gift card.

And 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 backend there. So thank you so much for stopping by and letting us know a little bit more about obviously what Taylore.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 and GPTs and that for our businesses.

Yeah, thank you so much. This is Anya Chen from Taylor.

Thank you.