Liftoff with Keith Newman: From Meta to Taelor AI – How Anya Cheng Is Using AI to Reinvent Fashion for Busy Professionals

Date: November 4, 2025
Guest: Anya Cheng, Founder & CEO of Taelor AI
Host: Keith Newman

Episode Overview

In this engaging episode, Keith Newman sits down with Anya Cheng, the dynamic founder of Taelor AI, a fast-growing startup transforming the men’s fashion experience using artificial intelligence. Anya shares her remarkable journey from Taiwan to Silicon Valley, her tenure at tech giants like Meta and eBay, and how she is leveraging her product, tech, and hustler mindset to solve real-world problems—specifically, by making shopping and laundry a thing of the past for busy, style-averse men.

Key Discussion Points & Insights

1. The Problem: Men Hate Shopping and Doing Laundry

• Customer Base: Taelor AI's target demographic is busy, socially active men—executives, sales professionals, professors, or even singles just wanting to look sharp without the hassle.
  • “Our customers are like you…They need to look good. But they are not into fashion, they don't read GQ...And they have been wearing the same thing repeatedly again and again.” — Anya Cheng [02:05]
• Pain Points: Most competitors in the fashion rental market are tailored for women or fashion enthusiasts. Anya observed the “decision fatigue” and ill fit for men in existing models, which required too much choosing and engagement.
  • “Fashion companies are designed for people who love fashion. That's why we start Taelor AI— for people who hate shopping and laundry.” — Anya [06:24]

2. The Solution: AI-powered Styling and Seamless Rental

• How the Service Works:
  • AI picks outfits for users (no manual picking required).
  • Human stylists review selections for perfection.
  • Real clothes are shipped for rental, return, or purchase.
  • No shopping, no laundry. Clothes can be shipped to hotels for travelers.
• Business Model & Economics:
  • Monthly subscriptions ($70–$100): offers access to a rotating closet of 5–10 garments monthly.
  • Customers may purchase rented items at a discount; Taelor gains additional recurring revenue.
  • “It's almost like leasing a car...They feel like this is so comfortable and looks like new. And it's 50% off from retailer...So we also make money from when they buy the rented clothes.” — Anya [03:50]
• Social Impact:
  • Reduces clothing waste and the environmental burden of fast fashion.
  • Provides feedback and data to fashion brands, enabling them to reduce wasteful production.

3. Growth & Validation

• Traction:
  • $2+ million in annual revenue within two years.
  • Venture-backed by notable funds such as Goodwater Capital.
  • Strategic partnerships with over 300 fashion brands.
  • “We are VC-backed...We have over $2 million in revenue and are growing fast.” — Anya [07:16]
• Diverse Team:
  • Ten full-time team members, bolstered by experienced industry leaders and ex-colleagues from major companies.

4. The Founder’s Journey: From Taiwan to Silicon Valley

• Immigrant Story & Early Hustle:
  • Arrived in the U.S. during the 2008 financial crisis with no professional network.
  • Relentlessly pursued informational interviews, networked through professors, and leveraged her skills as a journalist to access decision-makers.
  • “In Chicago in December, minus 20 degrees, I’ll send my resume to recruiters as they leave other departments.” — Anya [08:39]
  • Used creative tactics: became a reporter for Taiwanese media to get into expensive industry conferences for free.
  • “I put together a business plan...I didn’t know that means business plan...I happen to know someone, her name is Anya Cheng.” — Anya [12:21]

5. Big Tech Lessons, Startup Applications

• Key Transferable Skills:
  • “In big companies, everyone’s smart and has amazing backgrounds...Idea is cheap...people learn how to convince each other with logic.” — Anya [18:04]
  • Developed strategic frameworks for communicating and aligning on decisions—skills that proved critical when leading diverse teams in new ventures.
• Startup/Corporate Hybrid:
  • Importance of attracting team members not just with money but with opportunities for growth, learning, and impact.

6. AI as True Differentiator

• More Than LLMs:
  • Proprietary data modules built atop LLMs (like OpenAI).
  • Continuous feedback loops from user engagement inform both customers and partner brands.
  • Real-time customer feedback creates a “human-AI flywheel” for iterative product and content improvement.
  • “We use AI to combine with humans…We just won the American Marketing Association’s award—worst marketer of the year—because we get 10 million impressions for free from ChatGPT.” — Anya [25:58]

7. Favorite Founder Moments & Impact Stories

• Customer Stories:
  • Dressed a client for a court date in a child custody case: “I don't care what I wear as long as I win the case…If you help me to dress to win, I’ll be forever grateful.” — Anya [27:36]
  • Helped someone looking sharp for an office proposal (“pop the question”).
• Sustainability Impact:
  • “30% of clothes go from factory to landfill, generating 10% of carbon emissions... We help brands monetize their assets inventory and feed back data so they can do better job next year.” — Anya [28:46]

8. Advice to Aspiring Entrepreneurs

• Start Early, Get Involved:
  • “Involve early. Even our intern became our investor…Be an advisor, freelancer, investor, get to those rooms and build your network before going all in.” — Anya [30:20]
  • Participation leads to deeper insights, connections, and faster entry when you’re ready to launch your own startup.

Memorable Quotes

• On Leveraging One’s Own Superpower:

  • "The reason I didn't give up was I use something that I am good at. Because using your strengths, you then you are not afraid. When you are not afraid, you are willing to try one more time." — Anya Cheng [16:13]

• On Startup Team Building:

  • “You just have to find something outside of more than money that you can offer and finding opportunity to help each other.” — Anya [22:13]

• On the True Value for Customers:

  • "They're not just buying clothes…they are buying an executive assistant. They are buying the guy behind the superhero." — Anya Cheng [23:28]

• On Staying Customer-Centric:

  • “A favorite moment is always when you see you really solve a customer’s issue…If you help me to dress to win the case.” — Anya [27:36]

Timestamps to Key Segments

• Anya’s Introduction & Problem Statement – [01:10 - 02:05]
• Service Overview & Differentiation – [03:27 - 06:24]
• Traction & Investors – [07:16 - 08:00]
• Immigrant Hustle and Networking Stories – [08:21 - 13:33]
• Lessons from Big Tech – [18:04 - 20:27]
• Team Building and Hiring – [20:45 - 22:32]
• AI as Business Engine – [23:28 - 26:20]
• Human-AI Flywheel for Growth – [25:58 - 27:19]
• Impact Stories & Sustainability – [27:36 - 29:56]
• Advice to Entrepreneurs – [30:20 - 31:52]

Episode Conclusion

The episode offers a compelling synthesis of Anya Cheng’s journey: from an ambitious newcomer to the U.S., navigating adversity with resourcefulness, to a successful Silicon Valley founder using AI to create time-saving, planet-friendly solutions for a neglected demographic. Her practical tips—for both aspiring founders and those wrestling with what to wear—reflect her belief in leveraging personal strengths, the power of continuous feedback, and prioritizing impact over hype.

Listen to this episode if you want a refreshing take on product-driven entrepreneurship, AI applications in fashion, and the mindset required to build something lasting.

Connect & Get Involved

• Website: www.taelor.style
• Special Offer: Use code PODCASTGIFT for 10% off gift cards
• Contact: anya@taelor.ai

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