Diary of a CEO Full Recap w/ Emily

In this milestone 200th episode, 10 million in 10 years goes fully off-grid. Broadcasting from the beaches of Sri Lanka with a crew of adventurers/business owners. From building businesses and integrating AI, to reflections on growth, travel, and the power of community, this episode dives into the human side of entrepreneurship. Guests open up about the realities of remote leadership, leaning into discomfort, and how shared adventure accelerates connection. Whether it’s driving a tuk tuk for the first time or rolling out scalable AI tools for clients, the theme is clear: growth happens at the edge of your comfort zone.

In this episode, David reconnects with Graeme, co-founder of Agentary, to reflect on an incredible year of growth and transformation. From ticking off dream goals like buying a Porsche to merging businesses and scaling a full-service real estate marketing agency, Graeme shares the journey behind the milestones. They dive into the power of setting bold, emotive goals, the challenges of building a team, and why shifting from hustle to leadership has been both rewarding and demanding. With plans to expand to Melbourne, Queenstown, and beyond, Graeme also opens up about personal branding, fitness routines, and the mindset that’s fueled his progress.

In this episode, Marcus from Gerrard’s Insurance joins us to share how he and his team are reshaping one of the least glamorous industries by injecting creativity, speed, and bold moves into everything they do. From launching a robotic dog named Gerry to partnering with elite athletes and pushing digital-first campaigns, Gerrard’s isn’t your typical insurance brokerage. It’s fast, fresh, and focused on standing out in all the right ways. This conversation also covers fitness, mindset, AI, discipline, and why the people around you shape your trajectory more than you think. Whether you’re building a brand, a business, or just want to hear how two guys made insurance cool, this one’s full of unexpected gems and real talk from the inside out.