| Episode Type | Expert Insight Interview |
| Guest | Lisa Pagotto, Founder & CEO, Crooked Compass |
| Guest Website | https://www.crooked-compass.com/ |
| Listen | View on Sales POP! Podcast Page |
Lisa Pagotto built Crooked Compass into a multi-seven-figure adventure travel brand by staying fiercely anchored to a single purpose: taking curious travelers to the world’s most remote and stigmatized destinations. That clarity almost disappeared when a post-Shark Tank investor deal collapsed overnight, pushing the business into administration just one week before she became a first-time mother.
Rather than folding, Pagotto tapped a network of genuine relationships, rebuilt on her original values, and used Australia’s COVID-19 lockdowns as the catalyst for an aviation-powered pivot. Today, she leads two travel brands and draws on that experience to share a leadership philosophy built on alignment, radical transparency, and deep destination expertise.
Key Insights
1. Here is what you need to know about anchoring to your purpose under pressure
Pagotto traces her near-collapse directly to losing sight of her original why. The allure of celebrity investment pulled her focus from the values that made Crooked Compass successful, and the business drifted into administration as a result. Her recovery began the moment she reconnected with the purpose she started with — taking people to places nobody else dares to go.
2. Here is what you need to know about rebuilding from first principles
When Pagotto restarted, she returned to the same three pillars she had used at launch: a compelling why, a premium price point, and uncompromising service delivery. Those principles survived the pandemic, the administration, and a complete business pivot. Stacking growth on a clear foundation proved far more durable than chasing media attention or investor momentum.
3. Here is what you need to know about pivoting without abandoning your identity
During Australia’s strict COVID lockdowns, Pagotto used her government support payment to get a pilot’s license rather than wait out the crisis. That decision exposed her to private charter aviation, which she used to launch Crooked Compass by Air — private air tours to remote luxury stations. The pivot kept the brand’s core identity intact while opening an entirely new revenue stream.
4. Here is what you need to know about transparent leadership in high-touch businesses
Pagotto describes her leadership style as deliberately over-transparent. For destinations like Papua New Guinea, her team briefs travelers on worst-case scenarios — punctured tires, no hot water, unreliable roads — before they book. Managing expectations upfront reduces complaints, builds trust, and self-selects the right customers. Honesty about product limitations, she argues, is a stronger sales tool than polished marketing.
5. Here is what you need to know about authentic community engagement as a growth strategy
Crooked Compass holds one of only two Australian permits to access Mongolia’s reindeer tribes, a diminishing community of roughly 200 people. Rather than paying for access in tourist dollars (the community is barter-based), Pagotto’s company funds twelve dentists annually to provide healthcare to the tribe. That commitment earns trust, permits, and the kind of differentiated experience that AI and Google simply cannot replicate.
Pull Quotes
“I ended up getting my own business into administration because I just lost track of what my business was about, who I was, why I started it.” — Lisa Pagotto
“I decided that I would use mine to learn to fly. I needed something that would stimulate my brain because nothing else was at the moment.” — Lisa Pagotto
“The human touch that builds trust and connection and that demonstrates value — that can’t be replaced in our style of business by AI.” — Lisa Pagano
“If I just stick to what I did when I very first started this business 12 years ago — trusting my gut — that is why the business continues to flourish.” — Lisa Pagotto
Resilience & Remote Travel: Key Statistics from Crooked Compass
| Statistic | Detail |
|---|---|
| Business Age at Crisis | Crooked Compass was only 3 years old when it entered administration |
| Time to Rebuild Finances | Approximately 6 months of seeking finance after the administration event |
| Reindeer Tribe Population | Only 200 people remain in the reindeer tribes of Mongolia worldwide |
| Annual Permits — Mongolia | Only 20 permits per year are issued to each company to visit the tribe |
| Dentists Funded Annually | 12 dentists are funded per year to provide healthcare to the remote tribe |
| Pandemic Pivot Timeframe | Crooked Compass by Air launched during Australia’s COVID-19 lockdowns |
| Business Longevity | Crooked Compass has operated for 12 years as of the interview date |
Related Resources
Our Host
John is the Amazon bestselling author of Winning the Battle for Sales: Lessons on Closing Every Deal from the World’s Greatest Military Victories and Social Upheaval: How to Win at Social Selling. A globally acknowledged Sales & Marketing thought leader, speaker, and strategist, he has conducted over 1500 video interviews of thought leaders for Sales POP! online sales magazine & YouTube Channel and for audio podcast channels where Sales POP! is rated in the top 2% of most popular shows out of 3,320,580 podcasts globally, ranked by Listen Score. He is CSMO at Pipeliner CRM. In his spare time, John is an avid Martial Artist.
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