In this episode of Behind the Big Desk, we dive into the dynamic career of James Diaz, a leader who started as an entrepreneur, transitioned into the corporate world, and is now making the leap back into entrepreneurship. James shares the lessons he learned from building his first business, what drew him into the structure and scale of corporate leadership, and why he’s now returning to the fast-paced, high-stakes world of entrepreneurship. We explore the highs and lows of both paths, the skills that translate between the two worlds, and what it takes to take the leap—twice. If you’ve ever wondered about the trade-offs between running your own business and leading within a corporate structure, this episode is packed with real-world insights, reflections, and strategies for navigating both.