Diary of a CEO Full Recap w/ Emily

In this episode, we sit down with Willie, host of the award-winning Fresh Moni podcast, to unpack the cultural discomfort around financial conversations, the power of storytelling, and why normalising money talk is key to generational change. We dive into his journey from banking to launching a podcast that’s grown into a platform for education, empowerment, and real talk about wealth, values, and purpose. From winning at the NZ Podcast Awards to dreaming of building a Forbes-level media brand, Willie shares insights on business, belief, and taking consistent action without losing your roots.

In this episode, Matt from Lifestyle Lawns joins us for an open, grounded, and deeply relatable conversation about taking risks, backing yourself, and building something meaningful from the ground up. From walking away from a steady job to launching a business with no safety net, Matt shares the emotional and financial realities of going all-in while raising a young family and betting everything on an idea most people weren’t ready for.

In this episode, Jake Bailey joins us for a raw, honest, and wide-ranging conversation about resilience. From surviving cancer as a teenager to building a career around helping others navigate adversity, Jake shares hard-earned wisdom about emotional capacity, self-efficacy, and the strength that comes from intentionally doing difficult things, whether that’s running an ultra-marathon or having an uncomfortable conversation.