Catching up with Jacob Aldridge, portfolio entrepreneur, international business advisor, and keynote speaker who has worked with 400+ businesses across 14 countries generating $1B+ in new revenue. Speaking from Tunisia, Jacob explains how being a “deep generalist,” remote since 2010, and planning travel 14 months ahead enable a full-time, worldschooling life with his family. He shares why intentional design beats rigid career paths, how COVID unlocked global client work, and what it really takes to leap from a linear 9–5 to an exponential, owner-led path.

In this episode, you’ll learn:
• Specialist vs. deep generalist and how to stay adaptable
• Building a remote advisory practice and serving clients worldwide
• Planning systems for perpetual travel while keeping delivery on schedule
• COVID’s shift from boardroom to Zoom and why that mattered
• The “buffer time” you need to switch models and avoid the survival trap
• Designing a life across work, family, travel, and values