Fall Line Digital – E-commerce Growth Marketing Experts

How to Launch an AI-Powered Rental Clothing Line with Founder of Taelor Anya Cheng

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Anya Cheng is a Taiwanese American technology executive and entrepreneur in Silicon Valley. Before launching her artificial intelligence (AI) startup, Taelor, she helped build Facebook Shop, a social commerce initiative where people can explore and purchase products directly on Meta (formerly Facebook) and Instagram.

Before that, she led the go-to-market for Facebook’s Wi-Fi Tech and Innovation team where she improved digital literacy by bringing the Internet to countries without fast connections. As Head of Products, she transformed eBay Classifieds’ emerging business and built Target’s mobile tablet eCommerce app. As McDonald’s Senior Director of eCommerce, she launched their global food delivery apps from scratch. 


Cheng is currently the Founder & CEO of Taelor, a AI-powered menswear rental subscription platform busy men to rent styles and for brands/retailers to test products and predict trends. Taelor is an award-winning sustainability startup that has won various competitions hosted by accelerators including Draper University, University of Chicago Polsky Center and SPARK Accel.


Cheng is also an adjunct lecturer at Northwestern University and 500 Global (formerly 500 Startups) where she teaches software product management and marketing. She is the author of a best-selling career book, a TEDx Talk speaker, and a social media influencer. 


Cheng was named Girls in Tech 40 Under 40 in 2018 and nominated as a Marketer of the Year by Min Magazine U.S. in 2013. Her work has won 20+ awards including the Webby Award for Best for Shopping App, The Communicator Award, and the Rising Star Award of Social Network Category by Mobile Village. She is a volunteer career coach who has inspired thousands of young professionals and currently serves on the volunteer boards for the North America Taiwanese Engineering and Science Association, Taiwan Tech Arena (a non-profit supporting minority founders) and STUF United Fund (a non-profit supporting charitable causes.)


Cheng received her MBA from the University of Chicago Booth School of Business and a Master of Science degree in Integrated Marketing Communications from Northwestern University. 

In this episode you’ll learn about: 

  • Shifting from the large corporate world to a start-up brand – how Anya overcame the struggles of shifting from a world-traveling, top-name brand corporate employee, to starting up her own brand and working from home.
  • Ambassador funding – how Anya funded the launch of her start-up through crowdfunding.
  • Overcoming imposter syndrome – how Anya struggled with feeling out of place but how having the right wardrobe helped her feel more prepared and now she wants to give other people that same opportunity and confidence.
  • Serving the men’s market –  why Anya chose to target the male demographic and the problems her brand solves for men.
  • Finding the right business partner – how Anya chose her business partner based on their different strengths and backgrounds.
  • Launching a business during the pandemic – how Anya leveraged the work-from-home world to start her business off strong with fewer, more targeted items.
  • Created an environment where people want to work – how the employee mentality shift during the pandemic affected Taelor, and why people chose to work there.
  • The growth from a one-product shop to a one-stop-shop for all menswear needs – how Taelor went from selling only tops during the pandemic to expanding into a full men’s clothing line in just a few years, and why that decision lead to their success.
  • The power of a good wardrobe – Anya’s belief that people dress to achieve a goal, is her passion and inspiration behind her brand.
  • Working smarter, not harder – how Anya incorporated AI- systems to help run the workflow of the business so she can tweak things when needed but not have to be hands-on all the time.
  • Selling a solution – how Taelor is solving problems for their customers and how the focus on being a problem solver has made their marketing successful.
  • Leveraging SEO, magazine ads, and email marketing to grow brand awareness – Anya’s marketing strategies for Taelor and how she grew the brand name through multiple funnels and layers.
  • Understanding the customer journey – how Anya employed customer feedback to improve her marketing plan.




Connecting with Guest:

Connecting with the host:



  • 3:39 “Fashion companies are designing for people who are into fashion, they are not designing for people like me. I just want to get ready for the day and be successful.”
  • 7:36 “It was perfect, it gave us a little bit of tie to only serve tops.”
  • 8:21 “The world is changing, so it kind of forced people to think about their way of life and their career. Did they need to have a change?”
  • 12:18 “Something that I’m really passionate about is helping people not just look good but also look good to have a better life.”
  • 12:26 “I truly believe that people look great not because they want to wear blue or red, but because they want to get the job, or get the date, close the deal.”
  • 32:16 “AI only works when you have good data. Garbage in, garbage out.”

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