What if the next level of your business begins with a simple question: What do I actually want?

Matt Landau sits down with Clair Stoddard, co-owner of Cascade Vacation Rentals, to reflect on an unconventional leadership retreat along Minnesota's North Shore. Through hiking, sailing, and honest conversation, they explore how stepping outside the usual business setting can unlock creativity, vulnerability, and deeper connections.

Clair shares how nature shapes her leadership, why not everything meaningful can be measured by ROI, and what it means to become more visionary in an increasingly AI-driven world.

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 balancing technology, property management, and relentless entrepreneurship, Rena found herself asking a deceptively simple question: Is the juice worth the squeeze?

Together, they explore what it means to let go of a successful chapter in order to create space for the next one. Navigating uncertainty, trusting intuition over external validation, and redefining leadership in a world increasingly shaped by AI, rapid change, and human complexity.

From career pivots and ethical business building to community, motherhood, mentorship, and the search for meaningful impact, this conversation dives into what success really looks like when you stop measuring it by growth alone.

Because sometimes the next level isn't doing more.

It's getting honest about what's actually worth building.

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, emotional awareness, and repetition shape both personal growth and company culture. Together, they explore how AI is accelerating innovation in the vacation rental industry while also pushing leaders to reconnect with their voice, values, and sense of purpose.