Taelor style : The Aspiring Solopreneur

The rise of AI has sparked countless debates—Will it replace humans? Should we go all-in on automation? But for entrepreneurs navigating lean teams and high expectations, the real opportunity lies not in replacing people with tech, but in building smart systems where the two work together.

As Taelor Founder & CEO Anya Cheng said on The Aspiring Solopreneur podcast, “Some of the best things will probably be AI with human in the loop.” This isn’t just a philosophical stance—it’s a strategic one. Building the future is not going to be about AI versus Humans; it will be AI plus humans. And at Taelor, that’s exactly how we build.

One of the podcast’s most insightful moments came when Anya was asked a “chicken-or-egg” question: Should entrepreneurs build a human-first service and layer in tech later, or start with tech and bring in the human touch over time?

Her answer was refreshingly practical: It depends. “One person says AI will replace all the specialists, while the other says AI works best for general tasks.” Both, she noted, are probably right.

If you're an entrepreneur, your AI strategy should fit the problem you're solving and the resources you have. Are you a specialist who deeply understands your craft? Then AI can amplify your productivity. Or are you a generalist trying to scale? Let AI do the heavy lifting on repetitive or data-driven tasks while you focus on vision and growth.

One clear takeaway from Anya’s approach is that the real value in AI isn’t just about having the tool—it’s about having the data. As she said, “The true number one thing that will help you stand out is: do you have some really unique data that you can train the AI with?”

Soon, building an AI agent will be as easy as building a website on Shopify. The differentiator won’t be technical—it’ll be strategic. Whoever owns the most meaningful, unique data will win.

That’s exactly why Taelor stands out. Our styling technology isn’t built on generic datasets scraped from the internet. It’s trained on a goldmine of proprietary insights, including:

Real, unbiased style preferences: When customers rent clothing from Taelor, they aren’t influenced by pricing or discounts—they’ve already paid a flat monthly fee. That means we get clean, honest signals about what they actually like. “When you buy from a store, it’s not only because you like it—it’s also because of the discount. With Taelor, it’s what you truly like.”

Human stylist feedback, every step of the way: Our AI doesn’t work alone. It’s constantly learning from—and collaborating with—professional stylists to make sure the clothing suggestions feel personal and spot-on. “Our human stylists to make sure AI picks a perfect outfit.”

Data on garment quality and performance: Unlike traditional retailers, we clean and reissue the same garments multiple times. That gives us an unparalleled view into how clothing performs in the real world. “We wash the clothes after they’ve been worn. So, we know the true quality of a garment better than the fashion brand.”

A decade of styling data: Through strategic acquisitions, we’ve integrated ten years of past styling data that we acquired from professional styling companies into our system. “We combine all this unique data into a large language model and that is helping us differentiate ourselves.”

AI isn’t just a buzzword—it’s a tool. But like any tool, it’s only as effective as the hand that wields it and the data it draws from. Whether you’re just starting out or scaling fast, look for places where human insight and machine intelligence can work together. And if you’re building your own AI-driven service, don’t ask what the tech can do—ask what data you uniquely have that no one else does.

At Taelor, we’re proud to combine the art of human styling with the science of intelligent systems. That blend, not just the tech alone, is what truly lifts our customer experience.

To view further insights from Anya’s interview, watch the podcast episode here: https://www.youtube.com/watch?v=IrOGYX2RZ7w