The Flight of Authenticity: How Lisa Pagotto Leads with Humor in the World's Most Extreme Destinations
Lisa Pagotto · May 12, 2026
Interview with Lisa Pagotto
Podcast: Humor In The C-Suite
May 12, 2026 · 38 min
Listen to Lisa Pagotto on Humor In The C-Suite.
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About Lisa Pagotto
Founder & CEO of Crooked Compass, Guiding Personal Reinvention Through Experience
7 figures Scaled Crooked Compass globally12 minutes Shark Tank Australia appearanceAward-winning Travel brand founder2 ventures Crooked Compass & Crooked Compass by Air
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.
About this episode
What does leadership look like when your boardroom is a remote jungle and your team is scattered across time zones navigating geopolitical complexity? ForLisa Pagotto, founder of Crooked Compass, it looks like authenticity, resilience, and a finely tuned sense of humor. In this episode of Humor in the C Suite, Kate Davis sits down with Lisa to explore how the principles that make Crooked Compass extraordinary — cultural respect, genuine connection, and bold decision-making — translate directly into a leadership philosophy that any leader in any industry can learn from.
Key Topics Covered
Lisa and Kate explore how humor functions as a genuine leadership tool in high-stakes, high-complexity environments — not as performance, but as a way of managing expectations, building trust, and keeping teams grounded when the terrain is genuinely unpredictable. They dig into the cultural intelligence required to know when humor works and when it doesn't — how some cultures welcome levity while others require a more measured approach, and why reading that distinction correctly is a core leadership skill. Lisa talks about how sharing mistakes and failures with humor makes her more relatable to both her team and her clients, and why that vulnerability is actually one of her greatest strengths as a leader. They also cover what Crooked Compass by Air taught Lisa about pivoting under pressure, how she leads a remote team with authenticity and openness, and why she believes the future belongs to those who dare to do things differently.
"Sharing failures or mistakes or errors and turning them into humor just makes it more relatable." — Lisa Pagotto
About Crooked Compass
Crooked Compass is a multi-award-winning experiential travel company specializing in immersive journeys to remote and lesser-known destinations across the globe. Every experience is designed to prioritize cultural integrity, authentic connection, and meaningful exploration — free from the constraints of mass tourism. Visit https://www.crooked-compass.com
Connect with Lisa Pagotto 🌐 Crooked Compass Website 📼 Youtube
Additional Links & Resources:
Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!Learn more about me and my work at katedavis.ca
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Hosted by Kate Davis
Edited by Chris @ Wider View Studios
Guest: Lisa Pagotto
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5+ podcast & stage appearances. Remote or in studio, broadcast-grade audio.