Uncharted Worlds: Perspective-Shifting Journeys with Crooked Compass

Oct 29, 2025

In this engaging discussion, Lisa Pagotto, founder and CEO of Crooked Compass, shares her passion for frontier travel, emphasizing authentic cultural experiences over typical tourist routes. She reveals how her small-group tours take travelers to unique destinations like Papua New Guinea and Mongolia while ensuring local communities benefit. Lisa discusses the shift towards private tours post-pandemic and highlights the growing number of solo female travelers seeking transformative journeys. Her insights on sustainability and safety in post-conflict areas offer a fresh perspective on responsible travel.

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ADVICE

Do Firsthand Product Development

Build and sell frontier tours only after firsthand research and product testing with trusted local partners.
Walk the walk: don't offer experiences you haven't personally done or vetted.

INSIGHT

Perspective Shifting Over Luxury

Crooked Compass's trips aim to be 'perspective shifting' and emphasize deep connection and storytelling over luxury amenities.
Their clientele skews 55+ and well-traveled, with a rising segment of solo female travellers.

ADVICE

Prioritize Local-First Sustainability

Prioritize community-level sustainability by keeping money and opportunities within local communities.
Design exchanges that benefit locals educationally and economically, not just carbon-offset theatre.

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Curiosity changes everything. That’s the thread running through our conversation with Crooked Compass founder and CEO Lisa Pagotto, whose frontier-travel philosophy favors depth over dazzle and local impact over checklists. In this second episode of our Emerging Multi-Day Tour Operators series, we explore how she designs perspective-shifting journeys in safe yet overlooked destinations — from Papua New Guinea’s highland festivals and WWII relics to Mongolia’s sweeping steppe — and why honesty about difficulty, logistics, and culture leads to more meaningful travel.

Lisa reveals the craft behind the brand: small-group tours capped at 12, a post-pandemic rise in private touring, and a rigorous duty of care that comes before any itinerary is built. For her, sustainability isn’t about box-ticking — it’s about keeping money in local communities and creating genuine cultural exchange. We also look at who’s booking these trips: often 55-plus, well-traveled, with a growing solo-female segment seeking connection, storytelling, and transformation.

We chart what’s next in frontier travel — from the Balkans and the Silk Road’s five Stans to North Africa’s unsung gems like Tunisia and Algeria. Lisa also shares how she evaluates post-conflict destinations such as Iraq or Syria through careful risk frameworks, and why transparent pre-trip education turns hesitation into confidence. Along the way, a remarkable field story from North Korea challenges perceptions and captures the true spirit of perspective-shifting travel.

Come for the inspiration, stay for the playbook — how to spot emerging destinations, build local partnerships, and choose journeys that make a difference. Learn more at crooked-compass.com.

👉 Listen to Uncharted Worlds: Perspective-Shifting Journeys with Crooked Compass Now

🔥 Special Thanks to our Season 6 Title Sponsors for their Support: Holafly, Propellic, PayCompass, Kaptio, Civitatis and WeRoad

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