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. — 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. Share on X 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. Share on X 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. Share on X 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 serv