Digging Deeper with Crooked Compass - Episode 1

Lisa Pagotto has built her career by navigating uncertainty firsthand, founding businesses, making high-stakes decisions without guarantees, and learning what actually holds when plans fall apart. That throughline runs from the companies she’s built to the conversations she leads about resilience, leadership, and decision-making when there’s no obvious right answer.

She is the founder of Crooked Compass, an immersive travel company created in response to how surface-level modern travel had become. What began with Lisa personally designing small, story-driven journeys into complex destinations grew into a multi-seven-figure business, later gaining national attention through Shark Tank Australia. From the beginning, the focus was never volume or convenience. Crooked Compass was built around depth, cultural respect, and the willingness to handle difficult logistics in order to create meaningful experiences.

That approach was tested when global travel came to a standstill. With her industry paused overnight, Lisa chose not to wait for certainty to return. Instead, she rebuilt — and expanded — the business in unconventional ways. During the pandemic, she launched a second venture, Crooked Compass by Air, sparked by a decision that made little sense on paper: using government JobKeeper support to learn to fly when commercial aviation had shut down entirely.