What does it take to build a career that spans some of the world's biggest technology companies before launching your own AI start-up?

For Anya Cheng, it wasn't a perfectly mapped career plan. It was curiosity, resilience and an unwillingness to accept the first "no."

Born and raised in Taiwan, Anya arrived in the United States with little more than a marketing degree, limited English, and no professional network. Finding work after graduating during the Global Financial Crisis meant knocking on countless doors, creating opportunities where none existed, and refusing to let rejection define her future.

That determination led to leadership roles at Target, Facebook, eBay and McDonald's, where she helped shape global digital products, launch Facebook and Instagram Shopping, expand e-commerce, and rethink customer experiences at scale.

Today, she's the founder and CEO of Taelor, an AI-powered platform transforming how men discover, rent and buy clothing while helping fashion brands reduce waste through real-time customer insights.

In this episode of Future Fit Leadership, Anya shares why curiosity has been the greatest driver of her career, why the best leaders stop thinking about their job title and start solving problems, and how every setback became an opportunity to think differently.

Whether you're leading a team, building a business or navigating your own career, this conversation is a reminder that extraordinary opportunities rarely begin with certainty. They begin with asking better questions.

What does it take to build a career that spans some of the world's biggest technology companies before launching your own AI start-up?
For Anya Cheng, it wasn't a perfectly mapped career plan. It was curiosity, resilience and an unwillingness to accept the first "no."
Born and raised in Taiwan, Anya arrived in the United States with little more than a marketing degree, limited English, and no professional network. Finding work after graduating during the Global Financial Crisis meant knocking on countless doors, creating opportunities where none existed, and refusing to let rejection define her future.
That determination led to leadership roles at Target, Facebook, eBay and McDonald's, where she helped shape global digital products, launch Facebook and Instagram Shopping, expand e-commerce, and rethink customer experiences at scale.
Today, she's the founder and CEO of Taelor, an AI-powered platform transforming how men discover, rent and buy clothing while helping fashion brands reduce waste through real-time customer insights.
In this episode of Future Fit Leadership, Anya shares why curiosity has been the greatest driver of her career, why the best leaders stop thinking about their job title and start solving problems, and how every setback became an opportunity to think differently.
Whether you're leading a team, building a business or navigating your own career, this conversation is a reminder that extraordinary opportunities rarely begin with certainty. They begin with asking better questions.

Welcome to Future Fit Leadership a podcast for emerging and experienced leaders to learn, grow and become future fit! 

There has been a global shift in how we lead people. Traditional models are being challenged, and our workplaces are now dynamic. 


In this podcast you will hear and connect with leaders, CEO’s and change makers who will challenge the status quo and share their future ready strategies to unlock your growth. 


No matter where you are on your leadership journey this podcast will give you practical ideas and tools to help you think outside the square and become a change maker in your industry. 

Future Fit leadership is your place for bite sized learning, for time poor executives.

Contact Sadhana Smiles via email: sadhanasmiles@realchange.com.au

Or connect on LinkedIn https://www.linkedin.com/in/sasmiles/

Welcome to Future Fit Leadership a podcast for emerging and experienced leaders to learn, grow and become future fit! 
There has been a global shift in how we lead people. Traditional models are being challenged, and our workplaces are now dynamic. 
 In this podcast you will hear and connect with leaders, CEO’s and change makers who will challenge the status quo and share their future ready strategies to unlock your growth. 
 No matter where you are on your leadership journey this podcast will give you practical ideas and tools to help you think outside the square and become a change maker in your industry. 
Future Fit leadership is your place for bite sized learning, for time poor executives.
Contact Sadhana Smiles via email: <a href="mailto:sadhanasmiles@realchange.com.au">sadhanasmiles@realchange.com.au</a> 
Or connect on LinkedIn <a href="https://www.linkedin.com/in/sasmiles/">https://www.linkedin.com/in/sasmiles/</a>

Future ready leadership strategies to unlock your growth

Future Fit Leadership

'Future Fit Leadership — practical ideas for leaders on AI, the future of work, wellbeing, psychological & psychosocial safety, resilience and inclusive leadership.' 

There has been a global shift in how we lead people. Traditional models are being challenged, and our workplaces are now dynamic. 

In this podcast you will hear and connect with leaders, CEO’s and change makers who will challenge the status quo and share their future ready strategies to unlock your growth. 

No matter where you are on your leadership journey this podcast will give you practical ideas and tools to help you think outside the square and become a change maker in your industry. 

Future Fit leadership is your place for bite sized learning, for time poor executives.

Contact Sadhana Smiles via email: sadhanajsmiles@gmail.com

Or connect on LinkedIn https://www.linkedin.com/in/sasmiles/ 

We are excited to announce our partnership with Future Leadership and this podcast will sit in their Future Exchange Community where as leaders, CEO's, Directors and executives you can access content, events, live streams and connect with your peers. To join the community click on the following link, membership is free. 

https://community.futureexchange.global/groups/official

**Future Fit Leadership acknowledge the traditional custodians of the land on which we record this podcast and we pay our respect to elders - past, present and emerging. We extend that respect to Aboriginal and Torres Strait Islander people.

-- 

This is a Guide Your Light Network Production | Podcasts with Purpose

www.guideyourlightnetwork.com 

'Future Fit Leadership &mdash; practical ideas for leaders on AI, the future of work, wellbeing, psychological &amp; psychosocial safety, resilience and inclusive leadership.'&nbsp;
There has been a global shift in how we lead people. Traditional models are being challenged, and our workplaces are now dynamic.&nbsp;
In this podcast you will hear and connect with leaders, CEO&rsquo;s and change makers who will challenge the status quo and share their future ready strategies to unlock your growth.&nbsp;
No matter where you are on your leadership journey this podcast will give you practical ideas and tools to help you think outside the square and become a change maker in your industry.&nbsp;
Future Fit leadership is your place for bite sized learning, for time poor executives.
Contact Sadhana Smiles via email: <a href="mailto:sadhanajsmiles@gmail.com">sadhanajsmiles@gmail.com</a>
Or connect on LinkedIn&nbsp;<a href="https://www.linkedin.com/in/sasmiles/">https://www.linkedin.com/in/sasmiles/</a>&nbsp;
We are excited to announce our partnership with Future Leadership and this podcast will sit in their Future Exchange Community where as leaders, CEO's, Directors and executives you can access content, events, live streams and connect with your peers. To join the community click on the following link, membership is free.&nbsp;
<a href="https://community.futureexchange.global/groups/official" data-saferedirecturl="https://www.google.com/url?q=https://community.futureexchange.global/groups/official&amp;source=gmail&amp;ust=1683848489703000&amp;usg=AOvVaw2f0TqhapHFy9zLTwwgyebz">https://community.futureexchange.global/groups/official</a>
**Future Fit Leadership acknowledge the traditional custodians of the land on which we record this podcast and we pay our respect to elders - past, present and emerging. We extend that respect to Aboriginal and Torres Strait Islander people.
--&nbsp;
This is a Guide Your Light Network Production | Podcasts with Purpose
<a href="http://www.guideyourlightnetwork.com">www.guideyourlightnetwork.com</a>&nbsp;