Ask Willy Anything: Evan Osnos turns the tables on Willy Walker

For 300 episodes of the Walker Webcast, Willy Walker has been the one asking the questions. This time, the microphone changes hands.

Journalist and author Evan Osnos joins Willy for a special Ask Willy Anything episode, drawing on questions submitted by viewers and adding a few of his own. The result is a wide-ranging conversation that moves well beyond commercial real estate to explore the decisions, experiences, and ideas that have shaped Willy’s career and life.

What happens when the interviewer becomes the interviewee?

Evan begins with a question many longtime viewers may have wondered themselves: How does Willy fit so much into his life?

From there, the conversation quickly expands. Evan asks Willy about the habits he has carried with him over decades, his appetite for information, and the curiosity that continues to shape how he approaches business and the world around him.

What has Willy learned from periods of personal and professional reinvention? How does he decide when to push harder and when to step back? Which risks helped shape Walker & Dunlop, and which opportunities does he wish he had approached differently?

Evan also asks Willy to look back across 300 episodes of the Walker Webcast. With a guest list that has included business leaders, athletes, authors, policymakers, military leaders, and other influential voices, which conversations surprised him? What has he learned about interviewing people and getting them to share something they may not have discussed before?

From commercial real estate to AI, and what comes next

The conversation also turns to some of the questions facing business leaders now.

Evan asks Willy about the commercial real estate assumptions he believes deserve another look, how he views the rapidly changing economics of artificial intelligence, and what he would tell young professionals trying to build careers when technology is changing the nature of work.

They also explore Walker & Dunlop itself, including the decision to take the company public, the realities of leading through difficult market cycles, and Willy’s perspective on creating greater opportunity within commercial real estate.

Then comes the lightning round. Why was Willy once quite so competitive on the hockey rink? What took him to Burning Man? If he wrote a book about his life, what would he call it? And could his future eventually take him somewhere completely different from Walker & Dunlop?

For once, Willy doesn’t get to choose the questions. Register for the Walker Webcast to hear his answers.