Guest Bio

Lisa Pagotto is the founder and CEO of Crooked Compass, a pioneering adventure travel company redefining how people engage with the world. With a deep commitment to cultural integrity and immersive experiences, Lisa has carved out a space for meaningful, off-the-beaten-path journeys that challenge traditional tourism models. Her leadership empowers travelers to connect authentically with remote and emerging destinations — far beyond the ordinary itinerary.

Lisa is also a captivating speaker known for her raw honesty and practical wisdom. Drawing from her entrepreneurial path, she encourages audiences to embrace uncertainty, trust their instincts, and lead with resilience rather than perfection. Her storytelling inspires people to transform setbacks into opportunities and to rethink what success truly looks like. Whether on stage or in the field, Lisa champions bold thinking and values-driven exploration as tools for personal and collective growth.

Show Summary

In this episode of the Big World Made Small Adventure Travel Podcast, host Jason Elkins speaks with Lisa about her journey building Crooked Compass into a leader in experiential travel. They dive into how the company curates unconventional itineraries, often in lesser-known or emerging regions, offering travelers both challenge and connection in equal measure.

Lisa shares how safety remains a top priority in these remote adventures, and how traveler psychology — especially around risk and group dynamics — plays a crucial role in the experience. She also reflects on how her early travel memories shaped her vision for Crooked Compass, and what she’s learned along the way as a founder navigating the ever-evolving world of entrepreneurship. The conversation highlights the power of trusting yourself, staying flexible, and pushing past the expected to create something truly original.

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