How Taelor Is Redefining Style Through Data, Design, and Convenience - Phoebe Tan

In this episode of Making Cents of It All, Jesse sits down with Phoebe Tan, CEO and co‑founder of Taelor, the men’s clothing rental subscription service recognized by GQ as one of the best in the industry. Phoebe shares how Taelor is transforming men’s fashion, using AI‑powered styling, data‑driven personalization, and sustainable rental models to help men dress better with less effort.

Jesse and Phoebe explore the rise of fashion‑tech startups, the growing demand for men’s clothing rental services, and how Taelor’s subscription model is changing the way consumers think about convenience, confidence, and wardrobe management. Phoebe also discusses the challenges of scaling a tech‑enabled fashion brand, what she’s learned as a founder, and why sustainability and smart design are shaping the future of the apparel industry.

If you’re interested in entrepreneurship, fashion innovation, AI in retail, or the evolution of subscription‑based clothing services, this episode offers valuable insights into how technology is redefining everyday style.

Transcript

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Jesse Stakes: Hey everybody, welcome to this week's episode of Making Sense of It All. I have a guest that's a little bit different, little bit different topic than what we typically talk about. I have Phoebe Tan. She is the CEO and founder of Taylor.

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Jesse Stakes: Phoebe, thank you so much for joining us.

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Phoebe Tan: Thank you so much for having me.

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Jesse Stakes: So, the way I just intro'd you, my audience is gonna be like, what does she do? So, so, before we get into anything, at a high level, what is Taylor?

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Phoebe Tan: Taylor!

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Phoebe Tan: Ping Netflix for outfits.

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Jesse Stakes: Netflix for outfits, I like it.

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Phoebe Tan: Exactly. We help busy, professional men, you know, like yourself.

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Phoebe Tan: Your audience, right, they hate shopping, they hate laundry, they come to a tailor, we use the AI and our professional human stylists to pick perfect outfits for them, and it's a subscription model, they pay a fixed monthly subscription fee, and we send them perfect outfits.

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Phoebe Tan: And idea for any occasion, they wear the clothes, anything they love, they can buy, everything else they return and get new ones.

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Jesse Stakes: Fantastic. So, we'll jump into all of that here, but I really wanted to kind of pull it back first, because, like, one of the first things when I saw this, when I started looking into kind of preparing for this interview, I was like, God, I'm like, what made her start this? So, I gotta ask you, what inspired you to found Taylor?

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Phoebe Tan: Great! You have to start there, right?

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Jesse Stakes: Amen.

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Phoebe Tan: For me, for me, you know, I…

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Phoebe Tan: I've been using the clothing rental services for almost a decade now, so I am a minimalist by nature.

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Phoebe Tan: If you have a chance to visit my home, you can see I don't have a lot of things, okay? So, I treasure everything that I have, because I'm also very picky. You know, everything that I have, whether it's interior, my furniture, my clothes.

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Phoebe Tan: I take the time, you know, to pick what I like. So, everything is precious to me, okay? And because of my minimal nature, right, I like to use everything until the end of its life. It gives me a lot of satisfaction, okay, for whatever reason.

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Phoebe Tan: And, that's why I… I find the rental model fits perfectly, you know, to my lifestyle. And I started with Rental Runway. They are the pioneer in the rental, clothing rental space, been around for 16 years.

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Phoebe Tan: And, with the model, I don't have to shop anymore, right? I get to pick what I like.

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Phoebe Tan: And, you know, I can wear different clothes.

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Phoebe Tan: for any occasions, and, because I do know my style, I'm very picky, so… and then, about 3 years ago.

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Phoebe Tan: my co-founder and I, yeah, we both met at Chicago, both did our MBAs, pursued our corporate careers for the past 15 years.

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Phoebe Tan: And decided to join and start our first venture together, right? Naturally, we both are passionate, heavy users of the rental model. We look at… we started a space, right, and we realized that, wow, this is a fast-growing space, you know, the circular model.

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Phoebe Tan: And no one is tackling man space, right? And also, even though I've been using the services for so long, one of the biggest pain points that I still face

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Phoebe Tan: you know, today is browsing through thousands of items, picking and choose what I like. So that's a shopping journey that I don't like, I don't enjoy. So that's a pain point that we want to solve. It turns out, you know, a lot of guys.

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Phoebe Tan: have the same pain point. They just simply don't care so much about fashion. They don't want to pick and choose.

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Phoebe Tan: They don't know how, right? So that's why we decided to focus on men. We designed the journey using the AI to simplify the process. So, that's why we decided to launch Taylor about 3 years ago.

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Jesse Stakes: That's fantastic. So, would you consider yourself more of a technology company or a fashion company?

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Phoebe Tan: I would say, fashion tech, if I have to, you know, define ourselves, right? I think for a business model, without the technology and AI, it's just really hard to scale the business.

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Jesse Stakes: Yeah.

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Jesse Stakes: No, I think it's a fascinating space, and when you're talking about focusing on men, and I can speak for myself, and I think I could probably speak for a lot of guys that I know, you're not wrong. I mean, it's not something that men focus on. A lot of the times, people figure out a look or something that fits well for them, and they just keep buying the same things. Or they keep, you know…

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Jesse Stakes: They use… they'll wear it until it wears out, or they'll buy a million golf shirts, and that's what their closet looks like. It's just the same thing over and over again. I may or may not be describing myself.

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Jesse Stakes: But I think it's really cool. It's a way that people can explore different things for themselves. They can explore whether it's, you know, a more modern take on fashion, or if it's just, you know, like, the way that looks and things change over the years.

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Jesse Stakes: I would love to ask you, like, how does it work? So, on the front side of it, someone like myself, do they take a quiz? Do they, like, do they send in pictures? What does that look like on the front side? How do they get involved with it?

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Phoebe Tan: It's pretty simple. They sign up, as a member.

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Phoebe Tan: And they will have to complete, some basic question, right? We ask them what is their motivation, right? And they will tell us, you know, I need to refresh my wardrobes, I need more variety, I'm looking for something for work, for dates.

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Phoebe Tan: Right, and because we need to understand the occasion so that, you know, we can better tailor to their needs. And we ask them their measurements, right? Any specific brand that fits them best?

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Phoebe Tan: So that we can find the right fits for them, right? And, from there onwards, we have the baseline, you know, to begin the styling process.

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Phoebe Tan: They also have the option to speak with a professional stylist, a free 15-minute consultation call. A lot of customers love this, you know, opportunity to speak to a professional stylist.

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Phoebe Tan: Right? And for free, it's all included, right? And they get a fresh perspective, you know? And then… and then we will… after the call, or if there is no call, yeah, they can also chat with us, right, to gather additional information.

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Phoebe Tan: Oh, they may say that, oh, I have a specific event I'm going to, right? Can you please, yes, focus on that event? Or I have a vacation coming up, right? So it's very engaging, interactive.

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Phoebe Tan: And then we send them the… we send them their first shipment, you know, they receive the clothes, and then they give us their feedback, right? They will say, you know what, one of the items fits a little bit too tight. Everything else fits perfectly. So then we continue to fine-tune, you know, they may say.

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Phoebe Tan: You know what, yeah, I'm not so sure about this floral print. I'm open to try everything else, but maybe, you know, let's tone it down a little bit.

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Phoebe Tan: And I think there's a back and forth, and our stylists, you know, will also inspire, encourage them to mix and match, you know, different outfits, and help them to kind of expand their fashion horizon a little bit.

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Jesse Stakes: Very cool. So, you mentioned earlier that you utilize AI with this as well. And so, how does AI play a part in this process for your customers?

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Phoebe Tan: Oh my god, it's so important, right? I mean, today, at our stage, we are still considered early-stage startup. Already, we have thousands of styles.

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Phoebe Tan: You know, you can imagine.

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Jesse Stakes: Yes.

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Phoebe Tan: Yeah, there's a lot of, with thousands of sales, we have customers from 25 to 50-something years old, you know, they are, they are, over in the U.S, and with different professions, you know, obviously they may have different needs, right? Very different personas,

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Phoebe Tan: And then… and they give us different… they have different needs and expectations. Of course, different body shape.

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Phoebe Tan: different measurements, right? There's a lot of data points. It's almost humanly impossible.

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Phoebe Tan: To find the perfect style, perfect fits for you.

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Jesse Stakes: Yes.

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Phoebe Tan: So, without the JN AI, it's really, really hard for our business to scale. If we have to heavily rely on a human stylist.

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Phoebe Tan: You know, to style hundreds of customers, right? So, for a single stylus. So, with the AI, you know, Jane AI, and we are able to process all the product attributes, all the customer attributes, structure and structure information, images.

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Phoebe Tan: Right? And… and also built in some business logics, right? Because there are some, core top-performing products. They would want to give it a higher priority.

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Phoebe Tan: Right? And then, from there, yeah, the AI helped us to, to generate better outfits.

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Phoebe Tan: Better results, you know, for our customers.

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Jesse Stakes: Right.

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Phoebe Tan: time.

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Jesse Stakes: I don't think people think about that when they're, you know, they put something on and they say, oh, that shirt looks good on me, or they think these pants look good on me, but they don't think about why. They don't think about, like, how the measurements in certain parts, or if they're…

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Jesse Stakes: as far as certain spreads on collars, certain ways that the buttons fall on a shirt, all kinds of things, they… it all plays a part in how it looks on… on an individual, correct?

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Phoebe Tan: Yes, yes. I think the biggest… the biggest value of the styling service, you know, different from, say, a typical e-commerce, right? When you go shopping, typically, you pick one item at a time, store and filter. I want… I want shredder, then you go to shredder. I want jeans, you go to jeans category, right? For a styling service like ourself, we put together outfits for you. A lot of customers, they just simply don't know.

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Phoebe Tan: Do I wear this shirt with this pant, with this jacket? You know, they don't know how to color match. They don't know how to, you know, mix and match.

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Phoebe Tan: and styled differently, right? Because with the same jackets.

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Phoebe Tan: You can… you can style it very casually, very cool, very versatile, and you can style it like a smart business casual. You know, it's all about styling, right? I think that's where we add the most value to our customers, you know, for them. Wow, I have no idea.

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Phoebe Tan: You can wear a bomber jacket like this. Right. You can wear a shacket like this.

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Phoebe Tan: You know, they have a different appreciation of, you know, the individual pieces, how everything works together. And we also help them, hey, we also help them mix and match what they have, you know, already in their closet, right? And the goal is to help them elevate their wardrobe.

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Phoebe Tan: Right? And continue to build on the core staple pieces, and add on amazing pieces to their closet, right? And then the journey, you know, for us to be successful, right? We want to help them after using Taylor, say, for, like, 3 months. Wow, you know, JC, I know you have… you look pretty… pretty great, right? But some of our customers have no ideas about styles.

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Phoebe Tan: But after the journey, they have some ideas.

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Phoebe Tan: Okay, there are some scents of the color, different, different way, you know, to mix and match, yeah, certain pieces of clothes.

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Jesse Stakes: So you're teaching them as well.

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Jesse Stakes: There's an educational piece to it.

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Phoebe Tan: That's true.

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Jesse Stakes: There's another part about this that's gonna probably ring very true with some people and be very important, is it's very sustainable as well. You're not buying, say, you know, clothing that are made of plastic anymore, you're not throwing… you're not throwing away a bunch of things that…

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Jesse Stakes: Won't necessarily be biodegradable, you're actually utilizing these things for a much longer lifespan, and more people are getting more benefit out of it than just yourself buying inexpensive clothing.

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Phoebe Tan: Yeah, no, you're so right. I mean, this is something that I'm very passionate about, you know. The fashion industry is one of the most polluted industries. When you think about waste, right, if you look at your closet today, you know, the statistics shows that we only wear 20% of what we own in the closet.

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Phoebe Tan: What about the rest of the 80%? It's wasteful.

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Jesse Stakes: Yes.

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Phoebe Tan: Right? They're sitting there collecting dust, right? So, with the circular model, the rental model, now every single garment

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Phoebe Tan: has a chance, you know, to be utilized until the end of its life. It's okay if you don't love it, right? You return the code, someone else will love it.

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Phoebe Tan: until, you know, yeah, this piece of garment can no longer be worn. So, the beauty of the circular model is that we really, really focus on the value. We look at every individual piece by wear, how many times, you know, that…

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Phoebe Tan: Every single government is produced through very rigorous

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Phoebe Tan: production process, from design, development, you know, to distribution, to sales, right? And then the consumption. And if we just buy it, let it sit in the closet, that's very, very wasteful. But, you know, if we are able to circular it.

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Phoebe Tan: Right, and then that makes a huge impact in the environment if we can, you know, maximize the life of every single government. So that's our idea of our business model.

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Jesse Stakes: No, I think that's fantastic. So, let's talk about your business a little bit here.

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Jesse Stakes: You guys have had an incredible amount of success in a very short period of time. I think you've pre… I think if you had any doubt whatsoever that the… that this… that this model would work for men's fashion, I think that was put to bed with your first 18 months. You guys did over $2 million in over 8… in your first 18 months in existence, correct?

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Phoebe Tan: Yes, thank you, yeah. About 2 months. Sorry, 2 years.

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Jesse Stakes: That's fantastic. I mean, I don't… there's not a lot of startups that can say that.

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Phoebe Tan: Yeah, we are… I think timing, it's, you know, it's everything, right? The… the… I think 15, 16 years ago, when Rental Runway started, Rental Runway, you know, if you don't know, the, the pioneer of the rental, clothing rental space, right? When it first started, you know, nobody heard of it.

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Jesse Stakes: I think back then, you know, people only ran…

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Phoebe Tan: clothes for weddings, you know, bridesmaids, roommates, right? And, not… even when they first started, it's mostly event… event-based. And so, since then, there have been so many companies.

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Phoebe Tan: Including, most recently, we also have Newly, which is owned by Urban Outfitters, right, a successful public company. And they started… they see the future of the circular model. They started Newly 5 years ago, and newly today, it's a close to $500 million business in just 5 years.

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Phoebe Tan: Right? It just shows that, you know, the timing and the circular model, circular fashion, secondhand, yeah, it's growing. It's growing, very fast, right? The number shows that by 2030, the circular model, the secondhand markets.

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Phoebe Tan: Yeah, it's kind of worth $300 billion globally.

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Phoebe Tan: Amazing. That's amazing. The second hand alone, right, is gonna, it's growing, yeah, 7 to 9 times faster than the retail.

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Phoebe Tan: you know, sector, right? So, definitely a fast growing. That's why I think we are able to, to start Taylor at the right time. And with that also, the market has been educated. You know, rental sharing economy is not new, right? It's been booming across industries.

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Jesse Stakes: Yeah, absolutely. Is there… is there an opportunity, if people hear this, they're interested in the company, is there opportunities to invest in the company as well?

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Phoebe Tan: Yeah, I'm glad that you asked that, yeah. So, we're actually, raising a pre-A round, so we still, you know, invite

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Phoebe Tan: strategic investors, whether it's institutional or angel investors, right, they will provide value to the growth

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Phoebe Tan: to the expansion of Taylor, and we are welcome, or welcome investors, and… and so I can, I can include my, my email. I think Jesse in the link, right? So, so please.

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Jesse Stakes: Absolutely.

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Phoebe Tan: P.

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Jesse Stakes: Yeah, we'll make sure… we'll make sure that your contact information is… is listed with this, you know, when we post it, wherever we post it. We're not gonna… we'll make sure that you're not inundated with… with a bunch of… a bunch of stuff. We'll make sure that we get the best… the best email for you to where you're not… to where your inbox isn't just crushed with things, so…

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Phoebe Tan: I appreciate it.

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Jesse Stakes: If you had, you know, for my listeners and for the people, you know, that are hearing this.

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Jesse Stakes: if you had one thing that you wanted them to walk away from, after hearing this, and after kind of hearing about your company, hearing about where… where men's fashion and where fashion in general is going, you know, and the opportunity that Taylor represents, what's the one thing that you would want people to walk away from… walk away from this with?

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Phoebe Tan: Yeah, I would say, you know, to the listeners, right, the future of fashion is changing.

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Phoebe Tan: Right? Oh, and…

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Phoebe Tan: So, give it… give it a try. If you never try renting clothes, never try the subscription model, right? A lot of customers, you know, after trying the service.

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Phoebe Tan: It completely changed their lifestyle, you know, using Taylor, they really value the service, very service-oriented, right? After using Taylor for a while, they slowly start buying new clothes.

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Phoebe Tan: Right? And they become of their lifestyle. And together, we can make an impact, you know, in the environment.

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Phoebe Tan: Right, and really, I also challenge the audience to take a look of your closet today, right? How many clothes, right, in terms of percentage that you're actually wearing? So, changing the model, change your lifestyle, right? I think it will simplify, you know, your life significantly.

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Jesse Stakes: Yeah, I'm definitely guilty of that. I've got a… I'm that 80-20 guy. 80% of the clothes that I have in my closet, I probably have worn less than one time, so…

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Jesse Stakes: Now, I think it.

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Phoebe Tan: Not too late, not too late.

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Jesse Stakes: No, I just gotta figure out something to do with them.

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Phoebe Tan: Yeah, and to the audience, yes, I think with this podcast, we offer a special, discount, a 25% discount. You can use the promo code POCAST25.

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Phoebe Tan: And to apply a 25% discount when you subscribe.

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Jesse Stakes: Alright, so you heard Phoebe, 25% off for any customers that want to try their service. It's just PODCAST25 when you log in. We'll make sure you have links, we'll make sure that we put that in the description when we put this out for everybody. Phoebe, I want to thank you very much for joining me today. I learned a lot.

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Jesse Stakes: And, it's very exciting. It's very exciting, very exciting how successful you guys have been, and also where you're taking men's fashion.

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Phoebe Tan: Thank you so much, thank you for the support.

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Jesse Stakes: Absolutely. We'll catch you down the road.