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.