How Taelor Is Changing the $140B Men’s Fashion Market

When we started, we thought we were selling clothes. Yeah, because we style you and we sell you clothes and people buy clothes as well. We send out five items for people to rent. On average, people buy two and they wear another three and then they return the clothes we send to other people. We're selling clothes. That's not true at all. However, just like Coca-Cola, they never sell soda. They sell dreams, sell freedoms, right? Tesla never really sells cars. It's about the cool technology, the moderns. You are more cutting edge than other people. When you drive a gas car, it's not about the car. You actually feel like I'm more sustainable. I'm helping the environment. We realized, wow, our customers are really buying a piece of mind. I got to look great. I'm ready to rock. I'm on this podcast. I'm on this sales event. I'm going to this conference. I'm the keynote speaker. I'm going on a date night for the second time. Whatever the occasion is, it's a piece of mind. I'm ready. They can be themselves because they don't have to worry about other stuff. They focus on the conversation, the knowledge at present. We realized what we are selling is the cape guy behind the superhero. We're selling the concierge service, the convenience.

# Transcript

Exact assistance for those guys. And that's why our customers start asking us, "Where do I get my haircuts? We are closing company. Where to buy shoes? Which these shoes look good? Am I should I use his belt? And how about the sunglasses? These heads, like which one do you think is better? Oh, by the way, Valentine's is around the corner. Do you sell jewelries, flowers? What should I bring to the day nine?"

Right? So I realized we are helping them to get ready for their day. And what we are really selling is a convenience, is a peace of mind, and also is the chance to succeed. And there's a moment that we realize that, for example, when we're doing go-to-market and do marketing, we no longer target people who are fashionable. We target people who are achieving goals. We target people who are financial consultants. We actually help people how to make more money. We start working with dating coach to help people to get ready for the day night. We partner with dating sites like Coffee Meets Bagel. We sell to corporations that have large sales organizations. So then they offer us employee perks. Then their sales look good and the money goes back to the company. So entirely changed our go-to-market because we realized what we are really selling. The real value behind is a chance to succeed.

**Speaker 2:** I like it. I was thinking I could see a lot of how a lot of those partnerships would work. Anya, we are so used to hearing about AI in the go-to-market space when it comes to tech, right? You know, everyone thinks of AI and they're like, "Okay, I'm going to go to Claude or ChatGPT or Gemini and I'm going to have it make some cold emails or I'm going to ask it to help like with a strategy." But you're sitting at a different definition of AI with kind of personalization for sure. But in the commerce space, Taylor, it's an AI-powered styling platform. Crowded space. What's the wedge? What makes you different and why did you want to get into this space?

**Taylor:** Yeah, it's 42 percent of men in the apparel market and it's 140 billion every year. But most guys—you know, a lot of people probably wear the same thing again and again the last 10 years. And they open their closet and they have five different brand new—lemon, Nike, banana republics, blue brother—and every Thanksgiving they buy the same thing, but in fact, if you ask...

**Speaker 2:** You been in Adam's closet?

[Laughter]

**Taylor:** Yeah.

[Gasps]

Or we asked people and they were like, "I don't even know what I have because my wife buys all of my clothes right?" So ask them.

[Laughter]

Do they really like to be Steve Jobs, wearing exactly the same thing? No, they actually don't want that. One time I went to a conference and the person, the speaker, right next to me, he got on. He's like, "Wow, if you add me on LinkedIn right now, you will realize I'm wearing the same blazer that I had 10 years ago, which is on my LinkedIn profile." And he's like, "I probably should talk to Anya."

So I think a lot of them—a lot of places selling clothes—but either you have to buy or you have to pick. So because of that, people tend to either—if you have to buy, you tend to only use it like once a while, like the Trunk Club. You probably won't use it every month because you have to buy, then you have too much stuff at home. And nowadays, owning isn't always a good thing. Uber is convenient because you don't have to park. Netflix is good because you don't have to buy DVDs, right? So owning versus ownership—now people have a different definition. So in our model, because it's rental, because we style you—so those two combined help people in that they don't have to have commitment. And that's a big thing for our customer, because for salesguys, single guys, they don't like commitments and don't like to use their space for small things like this. Yeah.

And then on the other hand, because we pick the clothes for a man, so for sure you're going to give me feedback. "The sleeve is too long. One inch needed for my shoulder." And those amazing feedbacks actually feed back to the fashion brand. Today, 30 percent of clothes go directly from factory to landfill. 30 billion in the US alone goes to landfill every year. And that's a lot of money they can put back to the fashion brand. So we use this amazing data as AI agents and they're helping the fashion brand to reduce future inventory and increase future sales.

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That's super interesting. And so you're helping the consumer but also the brand themselves like make sure that they are capturing opportunities or data, which led me to another question as I was thinking about it. Because I would think you have a lot of one-off sales from like a rental perspective. How are you turning that data that you're gathering through that process into retention and not just using it as acquisition?

**Taylor:** For retention, of course, it's easy because if you gain weight or lose weight, you provide feedback. Then next time we do better, so that's more straightforward. Like your Netflix show—I like this. Now all I open is all Korean dramas. And so they help with retention for sure. But that data helps fashion brands is another story.

So imagine you are a fashion brand. You outsource to a manufacturer. The manufacturer outsources to a small manufacturer. After you receive the clothes, you sell it to a big wholesaler that sells to a small wholesaler. Eventually, customers buy the Nike in the store. It's actually like six steps before the true manufacturer actually made the clothes. As a result, they really don't have great insight. And that's why 30 percent of clothes go to landfill. Every year they create junk. And nobody likes to create junk, but it's just there's not a lot of insight back to them. They might know, "Oh, this is too big. What do I mean? Who is too big? Sleeves too long—one inch, one and a half inch, four, five inches? And from where? From Diego, who travels usually to New York? And for Adam, who wears these clothes? After we have been running three times, after washing three times, it gets loose or gets shrink. And that's why it's too small, right?"

So they don't have really detailed actionable insight. As a result, they just keep producing junk. And that's how we are using those insights back to them. And this part also feeds into AI, so nobody has to remember that information.

**Speaker 2:** Super interesting. The amount of data you get blows my mind. When you let's talk human behavior here for a second. So you have a ton of data. You know what people wear. You know what people return. You learn what people's styles are. I'm sure you then do all sorts of things matching it to height, weight, all sorts of other things. But what have you learned about human behavior that Taylor's tech actually needed to catch up to?

**Taylor:** Yeah, for example, we do ask when people sign up. People usually ask us, "How do AI know my style or sizing?" So we ask people some questions such as their height and weight, which we don't always use because most guys think they are taller and thinner. So they provide information that's not most accurate.

So we realized, "Oh, everyone thinks they are taller. Okay, great." So we asked them, "Okay, go to your closet, pick your favorite outfit, and tell me what brand and what sizes." No problem. I'm definitely size small. Oh my God, I'm actually extra large. So it happens all the time.

And so we ask people about their fit issues—usually sleeve too long, body is too tight. And we also learn that it's not about looking good. It's about looking good to achieve a goal. For example, when you go to a conference, we send you a very interesting print shorts. People come to you and say, "Wow, that's a very interesting print with a dolphin on it. Nice shirt." And it becomes a conversation opener. So now they are talking, and then eventually they close the union conference. Or they go on a day nine, we say, "Okay, how about there's one more blazer?" So then when you get out of restaurants and now you can put a blazer on the lady's shoulders and you score your second date. So it's about the goal behind, to achieve that goal. And it's not just about looking good.

**Speaker 2:** I love that. And as thinking of all the clothes he could get—

Yeah, I'm just thinking about like the rental piece is very interesting to me because like there is a lot of landfill that ends up happening, right? You're like, "Okay, I'll wear this for a period of time, then you like you don't wear it anymore." Um, and so one of the things I've been thinking about is using like why you picked men's wear, which I think we talked about a lot. Um, but do you think that particular segment of the market is more ripe for utilizing your service versus the female market? Like, have you guys thought about going into the female market? What was the—are you guys going to expand? Like, I'm just curious where that where your heads are as you get more data.

**Taylor:** Yeah, we're not. We're very focused. Uh, today the men's market is 140 billion. If you...

Look at women's space: it's 57% of the market. Men is 42-something percent of the market. There are actually 10 companies in the women's space, but each of them only has less than single digits of market share just because the market is so big.

So for bigger players like Nuuly, they make 500 million in revenue backed by Urban Outfitters. The revenue they make has bypassed the wholesale segment which they spent 30 years to build. So we asked them the same question: "Why are you not doing women and men? Why are you only doing women?" They say, "Oh, I only get less than 1% of market share now. I'm not interested in going anywhere else."

But for our model—because I think fundamentally the problem we are solving is entirely different, and the financial business model is also entirely different—women rent dresses because we want to wear different things every day. As a result, we will never buy the clothes. Why would you buy just like your Netflix show you watch every day? Why would you buy the DVD, right?

But in the men's market, our customers are not using us to wear different things every day. They use it more like "try before they buy." They use it as a concierge service to support them.

So if you would—do you sell your product to the man after he rents it? Is that the concept?

So when I send out five items on average, people buy two on average. Renting three times, the item gets sold already. And every item that gets sold, we make over 57% margin because fashion is actually a very high-margin business. You know, if you know the e-commerce business, I'm sure you know that fashion has high margins. But they are all afraid of inventory.

But in our model, because we pick clothes for men, therefore we have zero inventory. Just like your Uber car—you don't pick the car. So as long as you are an Uber driver, you for sure will get customers. And we are membership-based. So we know our customers. We know each customer's body type, taste, goals before they even become a customer. So of course we have inventory now with 150 different brands. And the moment you onboard, we will send you something. But as we source, we will for sure source exactly what you need because we already know who is going to rent them and we're going to assign stuff to you. So you don't have to pick. As a result, we don't have to buy inventory at all because we work with fashion brands. We say, "Hey, brands, you can send me clothes and I will pay you nothing. But don't worry, starting tomorrow, I'm going to rent it out because I pick the clothes. My AI picks the clothes. So Adam for sure is going to wear the clothes and he pays a monthly fee. Every time you rent, I will pay you something. So eventually you are going to make your wholesale money back and probably even more because people will buy the clothes."

So we have no inventory. You don't have to buy things up front. But for fashion brands, we get something out of their warehouse for free and we also help them promote to customers. And every time people are renting, they get feedback as well. So it's a win for the customer, a win for the wholesalers or brands, and a win for Tailor.

Yeah, so it's brand exposure for your vendors for sure. You know, something that I wouldn't have walked into a store and taken off the shelf or ever purchased—you're actually getting it in my hands. And from their point of view, maybe I fall in love with their brand. Hopefully I keep using Tailor, but now I love Dale's shirt brand and I'm going to go buy that brand outside of what I'm getting from Tailor. I think that makes a ton of sense.

I know you've talked about the psychology of decision fatigue. How does that actually show up in your go-to-market? Because when you look at AI or you look at Choose and Close or you look at all these options—or you know, I have to choose this month and next month—like how does decision fatigue show up in your go-to-market and how do you address that?

Yeah, I think when we go to, for example, when we are partnering with corporates to help employees give and provide that—for sure, they're helping their employees not have to pick the clothes. So then they save more time, right? And then when we are doing the marketing side of the house, what we are promoting is that you can save more of your mental space and the time that you save in shopping and laundry now goes to your video games, your date nights, or more time with your family.

So I think because we are very clear about who our audience is—we are not selling. If you think of the analogy of the cleaning business, we are not selling cleaning supplies, we are selling the time service. So we don't advertise on GQ, even though we ranked number one by GQ and Vogue, but because our customers will never reach GQ. They are actually people who talk about sports, F1s, NBA, and basketball. So we actually have crime. So we actually have partnered with more influencers on those things or ambassadors. And even for podcast hosts like you guys, people who talk about careers or business, are actually more relevant to our audience than the fashion side of the house.

Yeah, it's interesting what you're selling versus what your product is. I actually think that's a great correlation that you talk about, right? Like Coke isn't selling Coke. You're not selling clothes. I think that's something that a lot of people should take a look at when they're looking at what their value proposition is. What are you actually selling and what does your product allow people to have?

So tying back into product: I read that you teach product and marketing at Northwestern. What trends are you helping the next wave of leaders prepare for? Where is the world going? What are you teaching?

Yeah, I teach product management. That means building apps, building websites. I would say one key takeaway that I always tell my students is that, at the end of the day, whatever AI or technologies—you have to solve a problem, right? So for example, when I was at Target, our colleagues really thought AR/VR was cool at that time. Like you go to the store, potentially with this AR/VR, you can see these couches in your living room. And then you go down this aisle and suddenly you can see commercials. And the world is perfect. They will guide you through the store. You have a shopping list. It becomes in-store GPS. Turn right and turn left. You never miss an item in the store. Sounds so cool. They launch it. Nobody uses it.

But mom goes to a store, sometimes she forgets the milk. She comes out and says, "Oh, I forgot to buy one thing." While I'm solving the problem, yeah, but mom goes to a store to get lost. They don't want to install GPS. It's a time for their me time. It's a time for them to get away.

Everyone wants that. You go to Target for 10 minutes and you stay there for two hours.

Exactly. It's a time for them to get away from their husbands, right? So why would they want to install GPS? Yeah, they might forget one thing. So then they give them an excuse: "Oh, sorry, I have to, can you take care of the kids? I have to go back to buy the egg and milk," right?

So I think eventually you have to know what's the true problem you are solving and is the problem really big enough. So the same thing—when I was at Target at that time, AI wasn't as cool as now, but we already said we're going to use AI. Snap a picture, AI will write all of the descriptions, and then people can sell it faster. So at that time we launched it, actually not a lot of people used it.

Why?

We started doing research and realized people who sell, especially individuals, they really care about the accuracy of their description. They care that the items sell. So they actually don't mind spending time to make sure it's all right and all good. They feel great and they're ready to sell at a good price. So eventually, I think technology comes and goes. And if you are really not solving the problem, then you won't have an opportunity, even though it's a cool thing. There's no reason why people use it.

When I was at Sears, our website was faster than Amazon, but it didn't bring business for the company because if people don't want to buy your product, why would they want a fast website, right? So at the end of the day, do you have the value prop? Like Apple is easy to use, Android has a lot of functionality. Both of them are amazing, but very different products. LeBron is more good in defense and Curry is really good in three-pointers. They are very different.

You dropping the basketball knowledge.

So they are different. You only need one value prop and do very well. Because at a startup we don't have a lot of money, so how is it possible that you do check, check, check, check, everything? That's not possible unless you hire Adam and Dell. But usually, the easier way to succeed will be a big check—like I'm doing this better than anyone else.

It is one of the things we talk about with a lot of our clients: niche down to make expansive growth because you can't do everything for everybody. And so one of the things we do when...

# Transcript

We first come into a lot of clients is like, "What is it that you're really focusing in on? How can you execute extremely well in that space?" And then you can grow.

Yeah, that's a good strategy. My mentor, who is a founder of Rotten Tomatoes, he says if you look at Rotten Tomatoes, the only thing that matters is the meter—like, how much score is the movie. They can remove everything else, but that's the score that people care about. The same thing for Google. It started with just a box. There's nothing else. The search. And things behind it. YouTube founders, one of our investors, he says that it's about uploading video and finding the audience. But they do it so well that Google had to buy them. Instagram, you just snap a picture with a filter so people cannot see your true face, and then Facebook had to buy it. So you just do one thing very well. Like Google beat Yahoo. And at that time, Yahoo had Yahoo Finance, Yahoo Movie, Yahoo everything, but still Google beat Yahoo.

Until about three months ago, my wife still had a Yahoo email address. And I was speaking to a prospect yesterday who still uses a Hotmail email address to let you know how old and antiquated they are. Think about what their go-to-market motion is, Dale.

But you don't know that you have an AOL email.

I don't have an AOL email.

Yeah, you do.

I do not. Let me see if I have one.

I have an original Apple email. I have an mi.com. And I will probably never ever ever get rid of it.

All right, let's move into some rapid fire as we wrap it up. So here's the rules, Anya. We try to keep these answers to ten words or less. Every time you go over ten words, Dale tells me I have to pay him money. So save my pocket a little bit. What was the harder job—leading inside of Meta or outside now as a founder?

I think it's outside being a founder because you actually have to be a lot of different roles.

What's one AI tool you actually use every day besides Taylor?

We do use other tools. I see there Transcribe and see what's the action item I'm supposed to do, what I owe for Adam, for whatever promotion material, for example.

There you go. I love it. How do you personally reset when the founder roller coaster that we all know so well gets so intense?

I hold my cats and then tell him whatever I'm not happy about. And I'm lucky because my husband's a chef, so he cooks.

Nice. What's the most underrated product hire?

I'd say it's someone who's really good in growth. What I meant is that they actually know how to do the detailed iterations because people tend to like to open new features because new features are cooler, but it's a gross sky—like, iteration to make it right.

Love that.

Last one for me, and then Dale will end with his famous last one. Anya, what's the go-to-market metric that you think is most often misunderstood?

I think people tend to think about—I think when people do go-to-market, people only tend to think about what's the CAC, what's the cost to acquire a customer. But I don't believe that doing go-to-market is something like they want. We send out at least a thousand emails to them. How many people end up buying? I don't think that's ever the process. It's always a journey. Like, you iterated, iterated, iterated. You find something great. You launch a whole bunch of video. You find a good video with insight and you launch a new one to replace the old one. And it's always an iterated process. So I think people are just looking at CAC from the get-go for a one-time thing, which is what people make mistakes on.

Awesome. Love it. Last one. What is your dream vacation destination?

I think Spain. I think the seafood is so good. And then so I probably will go back to it. And I'm cheating. I'm getting a second answer. I got married two years ago, went to Bora Bora, Tahiti for our honeymoon. It was very, very nice. Any founder, when you sell your company, should go to Bora Bora.

Very nice. Nice. Anya Chen, thank you so much for joining the show. Where can people check out Taylor? Because it's not spelled traditionally. Where can our audience go to get some really cool styling? And where's Dale gonna go to get some styling?

Tailor Style. That's T-A-E-L-O-R-S-T-Y-L-E. TailorStyle.com. Use code PODCAST25 to get 25% off your first month. So it looks great. And if you are an investor, supplier, business partner for dating sites, career centers, and fitness centers, feel free to reach out to me. I'm Anya at taylor.ai.

Awesome. Anya, thank you so much for joining the show.

Thank you.