Lisa Pagotto

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. The journey culminated in Lisa requesting — and receiving — clearance to land a light aircraft at Sydney Airport while the runways sat empty of commercial flights, a moment that has since become a defining story in how she thinks about risk, permission, and acting without precedent.

The experience forced a reckoning with burnout, identity, and leadership beyond titles or growth metrics, reshaping how she approaches decision-making under pressure. Rather than chasing momentum for its own sake, Lisa began questioning long-held assumptions about success, safety, and what it means to move forward when familiar markers disappear.

Alongside leading Crooked Compass, Lisa speaks through keynotes, workshops, panels, and media conversations with organisations and audiences navigating change and uncertainty. Her work translates across industries and borders because it centres on universal pressure points, decision-making without guarantees, redefining success when old markers fall away, and building resilience that actually holds when plans collapse. She speaks from lived experience rather than theory, drawing on the realities of building, losing, adapting, and continuing without a safety net.

As a podcast guest, Lisa brings grounded insight into leadership, resilience, reinvention, and immersive travel, connecting real-world decision-making with the deeper human impact of how we explore, work, and live.