Building the Future of Fashion Tech and Sustainable Style – With Anya Cheng

We wear clothes every day. Sometimes we take time to choose an outfit, and other times we just grab what’s easiest. For many people, shopping feels like a chore, yet looking sharp still matters. Add climate change into the mix, and fashion choices become even more complicated. How do you stay stylish without adding to the 92 million tonnes of textile waste produced each year? This is where artificial intelligence meets circular fashion, and innovators like Anya Cheng are leading the way.

In this episode of The Best Business Podcast, host Daryl Urbanski speaks with Anya Cheng. She is an award-winning fashion tech entrepreneur and founder of Taelor.Style. This is the first AI-powered men’s clothing subscription built around sustainability. With experience at Facebook, eBay, Target, and McDonald’s, Anya brings deep expertise in AI, product innovation, and ecommerce. Her company fills a critical gap by helping busy men who dislike shopping or laundry look good while cutting down on fashion waste.

The conversation goes beyond fashion. Listeners will hear how AI, sustainability, and human-centered design can fuel new business models. Gain insights on innovation, entrepreneurship, and the mindset shifts needed to create lasting impact. This episode offers inspiration and practical lessons for anyone curious about the future of business and technology.

Here are three reasons why you should listen to the full episode: 

1. Gain proven strategies from Anya Cheng on how to validate a startup idea with minimal resources using AI tools.
2. Understand the impact of fashion tech on sustainability and why circular fashion is the future.
3. Learn tactical fundraising tips and networking hacks that helped taelor.style raise $2M from investors behind Facebook, Hello Kitty, and NVIDIA.

Resources 

• Anya Cheng: LinkedIn | Instagram
• Taelor AI: Website | Facebook | LinkedIn | Instagram | X
• American Marketing Association – 2025 Award Winners  
• WWD (Women’s Wear Daily): Website
• TechCrunch Startup Battlefield Competition: Website
• TEDx: Anya Cheng’s Talk  
• Best Business Podcast with Daryl Urbanski - Where you can find more insightful interviews like this one.

Episode Highlights

The Future of Fashion Tech and Sustainable Living

• Fashion is part of everyday life, shaping how we present ourselves whether we plan outfits carefully or choose quickly.
• Clothing choices also carry a global cost, with millions of tonnes of textile waste adding to the climate crisis.
• Enter Anya Cheng, award-winning fashion tech entrepreneur and founder of taelor.style.
• Her work bridges AI and circular fashion, offering busy men a stylish, sustainable solution to dressing well.

Solving Your Own Problem: Where Taelor.Style Began

• Anya admits she never imagined herself as an entrepreneur, believing it was a space reserved for "rich kids."
• Her transition into entrepreneurship began when she realized busy professionals with no interest in shopping had no catered fashion solutions.
• The MVP was a $10 Shopify landing page with hand-picked clothes for their first customer, Michael, acquired entirely without paid marketing.

Real-world validation came unexpectedly, proving market demand by focusing on solving sharp, niche problems.

Pioneering Personalized Style with Artificial Intelligence

• People aren’t buying clothes; they’re buying confidence, readiness, and freedom from decision fatigue.
• taelor.style repositions fashion as a service where users aren’t burdened with choices, laundry, or ownership.
• The backend leverages fashion tech and AI. It layers real human feedback, proprietary styling data, and trend forecasting to curate personalized fashion.
• AI uses past preferences, true customer behavior, and vast brand inventory to continuously adapt and improve.

How to Nail Your MVP & First Customers

• Without a product but with a clear vision, Anya built a functioning MVP using thrifted or sale items and personalized them for customers.
• An initiative with just a landing page and hustle led to the first 100 paying customers.
• Discovery that men wanted someone to “just figure it out” was key to pivoting toward an AI-powered service.
• Initial feedback helped taelor.ai identify the limitations of human stylists in scaling and the necessity for automation.

Outmaneuvering Barriers with Bold Creativity

• With no supplier at the start, Anya intercepted a WWD reporter leaving a press event, pitching the brand with a DIY business card.
• Rejections didn’t stop her, and persistence led to ABC News coverage via a Northwestern University student magazine.
• That coverage became leverage for WWD to publish an article, which attracted their first clothing supplier from Canada.

Lessons from Silicon Valley: Strategy, Logic & Collaboration

• Big company environments taught Anya that logic outpaces ideas or opinions when persuading teams.
• Collaborations succeed when goals are aligned, even if tactics differ, as long as the mission is clear.
• Tools like decision trees, strategy alignment, and data-driven arguments transcend corporate and startup applications.
• Clear insight: “You can’t convince people with your vision only with logical correlation to the company mission.”

Addressing the Gender Gap & Turning Marginalization into Strategy

• Women receive only 1.8% of VC funding despite founding nearly 50% of U.S. businesses.
• Anya shares inside strategies used at Facebook and Target to help women gain visibility and leadership opportunities.
• After seeing women fake being married to gain investor trust, Anya chose to rally underrepresented investor communities instead.
• Her pivot led to funding from immigrant, LGBTQ+, and minority funders, including investors behind Spotify, NVIDIA, and Hello Kitty.

The Psychology Behind Buying Confidence

• Customers aren’t buying clothing; they are buying the possibility of romance, career advancement, or sealing a deal.
• Taelor.style becomes their “superhero sidekick,” the gear behind their success.
• Strategic partnerships with dating apps, career centers, and fitness organizations expand value beyond fashion.
• In this way, fashion tech moves beyond clothing to deliver impact, transformation, and ease over materialism.

Fundraising Truths: Givers Gain

• Raising $2M came from unconventional paths, like professors who became investors or startup competitors turned allies.
• One major investor came through a connection formed by helping another founder, proving that givers gain.
• Anya once failed in a competition due to lack of confidence, despite having all the right answers.
• The key lesson is to know your material, but more importantly, believe that you have what it takes.

Fashion Tech and the Future of Sustainable Style

• The future of fashion tech via AI lies in specialized applications with unique datasets and domain-specific insights.
• Massive datasets from taelor.ai’s stylists, customer behavior, and brands provide a strategic edge over general AI tools.
• Layering domain-specific knowledge on top of large language models helps outmaneuver tech giants through focused innovation.
• The bigger mission is connecting sustainability to smart styling, reducing waste while building customer-centric intelligence.