Podcast Guest Kit — Chris Masiello

About Chris

Short Bio

Chris Masiello has spent more than four decades building and leading businesses across real estate, financial services and private capital. He is Chairman of The Masiello Group, one of Northern New England's most respected real estate and homeownership services companies, and Chairman and Trustee of MFC Investco, his family's private investment and philanthropy platform. He is the author of Mindful Mondays and Change: Short & Simple, both Wall Street Journal and USA Today bestsellers.

WSJ & USA Today bestselling author
Swanepoel Power 200
RISMedia Real Estate Newsmaker
40+ years leading through change

Conversation Topics

What Chris Can Talk About

AI Is the Opportunity, Not the Threat

Why a real estate chairman believes critical thinking matters more than ever in the age of AI, why a liberal arts education may be the best preparation for it, and why we have been here before with cars, air travel and the internet.

Where Did All the Houses Go?

How two decades of building too little created today's housing shortage, why waiting for a crash costs buyers, and the well-paying jobs in closing a gap of millions of homes.

Mindful Mondays for Busy Leaders

How short weekly notes to his team during the pandemic became a Wall Street Journal bestseller, and the one-idea-a-week habit that keeps a leader steady.

Change Without Fear

From Change: Short & Simple: why people resist change, how to reframe it from a threat into a tool for growth, and what unintended consequences can teach us.

For Hosts

Sample Questions

You've led businesses through 2008, the pandemic and now AI. What do people get wrong about change while they're in the middle of it?
Why might the thing an organization calls its biggest threat also be its biggest opportunity?
What did the arrival of the fax, email and the internet teach you about how people are reacting to AI?
Why does a business leader believe in liberal arts degrees?
If someone is waiting for a housing crash before they buy, what should they know?
How did a country this resourceful end up millions of homes short?
How did a weekly note to your team become a bestselling book?
What are unintended consequences, and why do they so often hide the next opportunity?
What does a mindful Monday look like for you?
What's the most common mistake you see leaders make when change arrives?