What would you do if someone handed you $10 million today?

It’s a question that has shaped nearly two decades of entrepreneur and Drexel University professor Dr. John Wilson’s life—and one he now asks thousands of people each year.

Appearing on the TLC Connections podcast with host GT Freeman, Wilson shared what he would do differently if he had $10 million.

Thinking About Entrepreneurship

He realized he wanted to help people think differently about work, entrepreneurship, and life.

That realization led him to pursue a doctorate in entrepreneurial leadership while continuing his corporate career.

He ended up at Drexel University, where he now teaches entrepreneurship and mentors aspiring business founders.

Over the years, Wilson has discovered that very few people actually need millions of dollars to pursue the life they envision.

“When people answer the question,” he explained, “I usually ask them, ‘Why do you need $10 million to do that?’”

The conversation often reveals that the first step toward a dream can begin immediately.

Accidental Entrepreneurs

Today, Wilson’s mission is to help what he calls “accidental entrepreneurs,” people with an idea, passion, or skill who simply don’t think of themselves as entrepreneurs.

His goal is to help 1,000 of them launch, grow, and thrive by 2030.

Much of Wilson’s teaching now centers on the rapidly changing role of artificial intelligence in entrepreneurship.

Embracing AI

Unlike many educators who initially viewed AI with skepticism, Wilson embraced tools like ChatGPT shortly after their release, integrating them into his courses almost immediately.

Instead of banning AI, he challenged students to use it responsibly, documenting how they interacted with it and learning to treat it as a collaborative thinking partner rather than a shortcut.

He believes AI is transforming education and business in much the same way digital photography transformed photography, not by replacing creativity, but by expanding what’s possible.

Wilson also introduced listeners to the concept of “agentic AI,” which goes beyond generating text by completing tasks and acting on a user’s behalf.

Redefining Every Profession

He believes these technologies will redefine nearly every profession and argues that students who aren’t learning to work alongside AI are already falling behind.

Entrepreneurship isn’t just about starting companies, he said. It’s a mindset built on curiosity, solving problems, experimenting, and creating value.

His advice for young professionals is simple: don’t wait until retirement, or until you have millions of dollars, to begin pursuing meaningful work.

Whether it’s creating a new folder labeled “My New Company,” volunteering for a cause you’re passionate about, or brainstorming business ideas with AI, the first step can happen today.

As Wilson sees it, the future belongs to those willing to start before they feel completely ready.

The Lincoln Center

The Lincoln Center for Family and Youth (TLC) is a social enterprise company based in the Greater Philadelphia Area.

Founded in 1970 by a behavioral health hospital, TLC is an entrepreneurial nonprofit providing innovative education, coaching, and counseling services to individuals and families, as well as grant writing and management services for school districts and universities.