Anya Cheng, Founder and CEO of Taelor, is making personal styling accessible to everyday professionals with an AI-powered clothing-on-demand service built for busy men and influencers. After 15 years leading product teams at companies like Meta, eBay, McDonald’s, and Target, Anya turned her own frustration with shopping and laundry into a mission-driven business that helps people look great, feel confident, and save time—while also supporting sustainability by keeping more clothing out of landfills.

We explore Anya’s Product Management Framework, the structured approach she uses to build and scale products. Instead of starting with technology, she begins by Identifying the Right Problem, then Looking at the Persona, Validating the Buying Journey, and Identifying Pain Points. From there, she Selects Decision Criteria to prioritize what matters most, Brainstorms Solutions, and finally Identifies the Right Solution based on impact, feasibility, and business value. She explains how this framework guides everything from launching Taelor to deciding which AI features to build next.

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7-Steps to Winning Products with Anya Cheng

Good day, dear listeners. Steve Preda here, Founder of the Summit OS Group. And my guest today is Anya Cheng, the Founder and CEO of Taelor, an AI-powered clothing on-demand service for men and social media influencers. Anya, welcome to the show.

Hello, this is Anya from San Francisco. I’m the founder of Taelor. We use AI to pick clothes for busy men. In the old days, only celebrities had their own human stylists. Now everyone can have their own AI stylist, and we send people real clothes to rent. Before starting the company, I spent 15 years in big tech companies. Most recently at Meta, where I helped build Facebook and Instagram Shopping. I was Head of Product at eBay and helped them launch new businesses in the US, Latin America, Africa, and Asia. I was also a Senior Director at McDonald’s, where I helped build their food delivery business globally when Uber Eats just started, and I helped Target build a tech office here in Silicon Valley. I’m excited to share more.

Okay, well we already got a lot out of you, so thank you for giving this quick bio. What I’m very interested in is what drives you. So you worked for Target. I think you worked for Amazon, at least with Amazon. You worked for other big tech.

EBay, McDonald’s, and Facebook.

Yes, so big tech companies like Meta. What makes someone who is a successful leader in big tech break out start as an entrepreneur? What is your personal “Why” that drives you and that you want to manifest in your business?

Yeah, it actually start with my personal problems that I had. When I was working for Meta, I was a few female leaders there leading large technology team. So I felt a little bit of imposter syndrome. I wanted to look great, but I don’t want people to find out that I’m freaking out every day. So I tried some subscription boxes like Stitch Fix, which is similar to the old Trunk Club. It’s good that someone styles you. But once you receive those boxes, you have to decide right away: how many times am I going to wear these clothes? And you have to buy before you can wear them. So can I find something even cheaper somewhere else? How do I pair these items? And once I buy them, I have to do laundry, ironing, and folding. It’s just a lot of work.

So I started using rental companies. I rented from companies like Nuuly, which is a $500 million revenue company, or companies like Rent the Runway, which is a public company. They are all great—you can rent, you don’t have to buy. But they require people to pick from hundreds of thousands of garments. You spend two hours picking, picking, picking, browsing, browsing, browsing. And I’m not into fashion. I don’t like fashion. I don’t have time to do shopping. I’m not fashion-forward, so I don’t even know how to pick. That was the “aha” moment for me—

I realized most fashion companies are designed for people who are into fashion, not for people like me who just want to get ready for the day and be successful.
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So I started doing research. Are there other people like me—who hate shopping and laundry but need to look good, be socially active, go to meetings, close deals, get jobs? It turns out there are a lot of people like me: busy men, single guys, salespeople, consultants, pastors, recruiters, professors. There are 15 million single men, 14 million sales professionals in the U.S., and it turns out we started Taelor to help people like me look great without having to think about fashion.

Well, I don’t know—if you look at my shirt, I probably could also use some Taelor treatment, an AI telling me how to dress better. So what drives you? I understand this is a great idea and definitely necessary, but what makes you excited about it?

I think I’ve personally always been passionate about helping people achieve their goals. I started as a blue-collar kid—my mom is a housewife, my dad is a factory worker, originally from Taiwan, and they’ve been in the U.S. for 20 years. As an immigrant, I came to the U.S. and was very lucky to have a lot of people help me. I got a student long ago, went to Northwestern University, got my MBA from the University of Chicago. I came to the U.S. without knowing anyone here, but many people helped me achieve the American dream. So it has always been in my heart to help more people achieve their dreams.

What I realized was that dressing well really helped me—almost like a student who buys a textbook and feels ready for the exam even though they haven’t read it yet.
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People using amazing software or tools will buy books or start learning and already feel smarter than before. It’s really a peace of mind that helped me. So I’ve always been passionate about how I can help more people achieve their goals, their dreams, and their full potential. I realized this business helps me do that. I’ve tried to do that in other ways before: I’ve published books, created online courses, and taught at Northwestern University.

But this business is an additional way to help people achieve their goals. At the same time, my co-founder, Phoebe, who is originally from Malaysia, she has been in the U.S. for 20 years. Growing up, she wanted to be a fashion designer, but in an Asian family, she became an accountant and finance professional, eventually a CFO. She always had a little spark in her heart to do something related to fashion, and she is very passionate about sustainability. She constantly talks about how today, 30% of clothes go directly from factories to landfills, generating 10% of carbon emissions and polluting 20% of the world’s water. Sustainability is really close to her heart. By the time she had worked for 15 years, she felt ready for a change, and we both shared the same vision. That’s how we started the business together.

Love it. It’s really a mission-driven company. I didn’t realize this when we first talked, but a lot of people are held back by not being well-dressed. Again, I don’t want to be the example here. I also like the idea because my daughter talks a lot about throwing away clothes and how much damage it does to the environment. I really like that you help people wear and buy only the clothes they actually need and send back the ones they don’t. This is awesome. So let’s switch gears here. I’m really curious about how you develop your products because this is a very creative business. You have to develop a new, revolutionary concept and product. Do you have a framework for developing these products?

Yeah, absolutely. We always start with the problem we are solving. I teach product management at Northwestern University, and most people, when they think about building a product, their first thought is, “Hey, what product am I building? How do I build it? What technology should I use?” We use AI to build this—we build AI agents—but in fact, you should take a step back. There are two equally important questions you need to ask: what problem should I solve, and what solution should I pick? Most people spend 95% of their time thinking about what solution to pick. But first, you need to figure out what problem you should solve. The problem you solve is actually the most important thing, because if you’re solving the wrong problem—one that people don’t care about, or one that won’t help your business, or one that you can’t actually solve—then no matter how great your solution is, it’s going to be a waste of time.

For example, what we found is that we are totally different from women’s rental companies. The problem we are solving is for guys who are busy but socially active. They have dreams. As a realtor, I want to sell one more house. As a small business owner, I want to grow my business to open a second restaurant. So they have a dream.

Dressing well and looking good is something that helps increase their chances of success—getting a job, closing a deal, showing up confidently.
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What we are really selling is a concierge service, an executive assistant, a fairy godmother, a gadget guy behind the superhero—it’s peace of mind. If you look at women’s counterparts, like Nuuly or Rent the Runway, they have hundreds of millions in revenue each, but they are solving a problem for women like me.

So we want to look great every single day and want to wear different things. So wearing different thing versus, I don’t want to think about it, is actually totally different problem. So if you think of our business model financially is different. For example, in women’s rental businesses, margins are very low because people rent clothes and don’t buy. On top of typical e-commerce costs like shipping, there are additional costs like laundry, so margins remain low. But in our business, customers use the service as “try before you buy.”. They want to save time and save space. So a lot of our revenue actually also come from people actually buying the secondhand clothes.

And those people are people who would never buy secondhand before because they don’t have time. So those are white-collar, busy men renting clothes and also buying them. In addition, they ask me where to buy shoes or accessories, Valentine’s Day gifts, where to get haircuts, even where to go on vacation. They treat us more like an executive assistant service. They give us lots of feedback, and we monetize that feedback back to fashion brands to help them predict what’s going to sell.

Okay. That’s fascinating. So it’s a two-way business because you are also selling the data that you’re collecting from people.

Customer feedback, like “the sleeve is too long,” “the fabric is too tight,” “this isn’t flexible,” and also insights like, “This is an amazing brand, but it’s too expensive compared to 90% of our other brands on the platform, so you should lower your price.” We give that feedback to brands so they can improve.

Yeah, which is basically data they don’t have—and it’s very valuable. That’s fascinating. So, going back to the framework—because we’re a podcast about frameworks—I want to make sure we have a clear framework. You identify the right problem first, and then you reverse-engineer from there. What are the steps to get from the right problem to the right solution?

Yeah, so going from the right problem to the right solution—that’s step number one. To solve the right problem, you first need to understand your personas. For example, a simple persona for us is a busy man who isn’t into fashion, such as a single guy, a busy dad, a sales professional, a consultant, or a pastor. Then you map out their journey. For example, they might need to go on a business trip, attend a meeting, go to a birthday party, or go on playdates with their kids. Along that journey, they realize their clothes are old or out of style, and they need different outfits. But when they look at what they have from last year, the clothes are already too small or too big.

So you identify the journey. So for example, they realize they need new clothes, and there’s a moment they say, “Okay, I can either buy exactly the same thing as last year, or… hey, I heard people are actually renting through women’s counterpart—maybe there’s something like that for me.” It’s like when you’re bored and deciding whether to stick with Comcast or try Hulu, Disney+, or Netflix. So identify the journey. After mapping the journey, the third step is identifying the pain points. A simple feature, for example—Facebook. We all use Facebook, and one feature is the birthday feature. The personas are people who have a birthday and people who want to wish their friends a happy birthday. The pain point for the birthday person is: “I’m not sure if I should tell people, but I also don’t want everyone to forget my birthday.” For friends who are close to the birthday person, their pain point is: “I forgot my friend’s birthday.”

So you have a lot of different pain points. Once you have your persona, their journey, and their pain points, the fourth step is to define your selection criteria. For example, you want to pick the biggest problem to solve. What should your selection criteria be? How many people are impacted, how painful it is for those people, and how likely you are to be able to solve the problem effectively. Then you choose one pain point to focus on. For example,

for Taelor, we pick that we want to help busy men who are not into fashion to dress well. The pain point we addressed is helping them save time and look great.
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We didn’t try to solve other problems. For example, a luxury menswear company might offer Louis Vuitton or Burberry for rent. The pain point they address is helping people who want luxury clothes but can’t afford them, which is very different from our focus. The key is to use your selection criteria to pick the right pain point to solve first.

Now you have the pain point. For example, for me, it is helping people have peace of mind and achieve their goals. Now you start using exactly the same framework for your solution. You pick your selection criteria and identify different solutions. Take Facebook birthday as an example. Oh, the problem I want to solve is that for people who are birthday boys or girl’s friend, they want to host a party. Now you can come out with plenty of solution. For example, the solution one could be AI generating party locations. The solution two is AI generate invitations. The third could be AI suggesting a party game or activity. Then you do the same thing—you identify your criteria. There are so many solutions, so what’s my criteria? The criteria are: which solution solves the pain point better? Which one requires fewer engineering hours? Which one can drive more engagement, traffic, or revenue for the company? Then you use the framework to pick the solution.

Yeah. Love it. Okay. That’s fascinating. So you find the right problem. Then you look at the persona that has that problem. Then you identify the pain points that really bother these people.

You find those persona and journey. That’s how you find a problem.

The journey as well. So the persona. Okay. And these are busy men, so you map their journeys. They need to go to church, they need to go to meetings. Then you use your criteria to select the solution.

That’s right.

And then you basically stress test. Is this the right solution? Does it fit the criteria? Does it handle the pain points? Fascinating.

Yeah. So you’re selecting criteria for your problem. And after you pick the problem, you have the same different selecting criteria to pick your solutions.

Yeah. Got it. So how do you decide what features to develop? You have your product—you’ve got the clothes. People can order them, try them out, and send them back. You take care of the laundry. They don’t have to worry. AI gives advice. How do you know what features to develop to define your product further?

Yeah. So the features to develop use the same framework. We start with the problem. Then we ask, what feature—or solution—solves that problem? For example, our customers say, “I hate shopping.” The solution is our AI shops for them. But they also say, I have a little bit points of views. So then we offer them a chance, they have a style quiz. They can upload a picture, say “I don’t wear pink, blue, or green,” And they can say, “I never wear turtlenecks.” And then they show a few pictures of the style that they like, if they have any, or we show them pictures to like or dislike. This way,

we understand their preferences and pain points. And then when they decide a feature, we're thinking about the solutions to address their pain points.
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So for this example, and in terms of getting into the Product Management framework:

If you are really going into product management, how do you find out the solution using quant and qual? For example, you interview your customers, run focus groups, check Google Analytics, Adobe Analytics, Shopify data, QuickBooks—your data points. Then you have qualitative and quantitative numbers. From there, you see the opportunity for a feature. You might identify a pain point: everyone comes to our homepage, but they drop off on the second page. Why? The homepage isn’t very clear. There’s no clear call-to-action button; the button was hidden. It was below the fold. Users have to scroll three times before they see the button. So, okay, I have a hypothesis.

The hypothesis is that people drop off because they don’t see the call-to-action button. So I’m going to come up with a solution. Solution one: move the button to the top. Solution two: have a floating button that is always visible. Solution three: show a pop-out button. And then using the same framework, like, okay, these are three great solutions. Which one take less engineering hours? Which one will potentially solve the problem better? Which one do we think will be more effective or generate more revenue? And then you decide. That’s how we decide on the features.

Yeah, that’s great. Then the AI keeps learning your criteria, keeps refining, and keeps suggesting better and better-fitting clothes. It gets faster from there, I presume.

Yeah, because the customer provides feedback. Your Netflix shows—when you start, you might watch all the true crime. But after a few weeks, you start watching other things, like romcoms or Korean dramas. They see what you watch, and you start seeing those suggestions too.

At the same time, what’s different at Taelor is that we know the problem we’re solving: helping people try something a little out of their comfort zone, because that’s why they want a stylist.
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So we also tend to recommend something new. We work with over a hundred different brands, so we might suggest something they haven’t tried before. “Oh, you’ve never tried purple? Why not try these light purple shirts? They look really good, similar to blue.” “Oh, you’ve never tried pink? How about this spring pink t-shirt? It’s really nice.” It’s a rental, so they don’t have to commit, and they’re willing to try something new—just like with Netflix. “I’m not sure if I’ll like the show… watch five minutes, we’ll see.”

And then, is this a global business, Taelor, or is it focused on the U.S.?

It’s focused on the U.S. We serve nationwide—anywhere the post office can reach. After people sign up, shipping takes one to three days. They wear the clothes for a couple of weeks. After that, they return the clothes in a prepaid envelope. They can go to the post office, or use a post office app with one click to schedule a free pickup. You can also drop it in blue collection boxes on the street. If you’re traveling—say, to New York for business—you can just return it at the hotel lobby. It’s prepaid, just like any package. You ask, “Can I mail it back?” It’s prepaid. They always say yes, and then you go home, and new clothes has arrived. You don’t have to do any laundry when you get home.

And you don’t have to check in your luggage.

Exactly. You don’t have to.

And to get on and off the plane quickly. I love it. That’s great. So if people would like to learn more, or they’d like to check this service out, or want to connect with you personally, where should they go? Where can they find you?

Yeah, go on https://taelor.style. Use the code PODCAST25 to get 25% off your first month or use the code PODCASTGIFT to buy a gift card with 10% off. And if you are great suppliers or business owners, you also want to tap on and work with your product, perfect for man who are busy. We love to partner with you. We work with dating sites, fitness centers, career coaches, and executive coaching companies. We also do holiday gifting, employee gifting, and new hire gifting to help your employees look great and save time. For investors, we are now backed by some of the largest consumer investors in the U.S., such as Goodwater Capital, the investors behind Lyft and Socar, Facebook, Twitter, and Spotify. Reach out to me at anya@taelor.ai.

That’s perfect. So, just so we don’t forget, you’re an AI-driven company. That’s amazing. So, if those of you listening to this enjoyed this conversation and learned something, you learned how to build a product: starting from identifying the right problem, looking at the personas, determining the persona, the journey, the pain points, selecting the criteria, and then picking the right solution. So, if you want to learn more about that and similar frameworks that accelerate your business, make sure you stay tuned, because every week I bring an exciting entrepreneur or thought leader who’s going to help you fast-track your business. Anya, thank you for coming, and thank you for listening.

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7-Steps to Winning Products with Anya Cheng

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Management Blueprint | Steve Preda

321: 7-Steps to Winning Products with Anya Cheng