Jun 2, 2026
What happens when the thing you built no longer feels aligned with where you’re meant to go?
In this episode, Matt sits down with Rena Pacheco-Theard, CEO & Co-Founder of Boutiq, for an honest conversation about transformation, calculated risk, and the difficult decisions that come with growth.
After years...
May 14, 2026
In this episode, Chris Hynes, Co-Founder and CTO of OwnerRez, joins Matt Landau for a wide-ranging conversation on public speaking, self-discovery, leadership, and the human side of AI. From Toastmasters lessons and storytelling breakthroughs to leading engineering teams through uncertainty, Chris shares how creativity,...
Apr 23, 2026
A thoughtful conversation between Ryan Casey, CTO & Principal of Lighthouse Vacations, and Matt Landau on navigating the tension between fear and opportunity in the age of AI, through the lens of hospitality, leadership, and purpose.
From unpacking public skepticism around AI to practical, real-world applications inside...
Apr 23, 2026
A conversation between Matt Landau and Clair Stoddard, co-owner of Cascade Vacation Rentals, on the power of stepping into the unknown—where growth, leadership, and authenticity truly begin.
From career-defining leaps of faith to redefining “failure” as a pathway to opportunity, Clair shares how embracing...
Apr 16, 2026
A conversation between Jack Zoppa, CEO of Haven Vacation Rentals, and Matt Landau on turning AI experiments into real business advantage—where agents, automation, and clear vision unlock scale, while human connection remains the true differentiator. Reach out to Matt directly: