Episode Details

What do you do when there is no roadmap — but standing still is not an option?

In this episode of It’s In You, I sit down with Lisa Pagotto, Founder & CEO of Crooked Compass, to explore what it really means to lead through uncertainty, disruption, and reinvention.

Lisa shares her remarkable journey of building a travel business from an idea she deeply believed in, surviving a difficult Shark Tank aftermath, navigating the pandemic as the travel industry shut down, and creating a second business by following curiosity, instinct, and movement.

Together, we talk about bold decisions before proof, resilience that does not mean endless pushing, and why leadership requires both courage and rest.

This conversation is an invitation to stop waiting for certainty — and start with one small move.

Key Takeaways

• You do not always need proof before you begin.
• Curiosity can become a powerful leadership strategy.
• If you do nothing, nothing changes.
• Resilience is not the same as pushing through.
• Rest is not weakness — it is part of sustainable leadership.
• Leadership requires energy, clarity, and emotional steadiness.
• Your values help you know when it is time to evolve.
• Boundaries are built through practice, not overnight.
• Sometimes the smallest movement creates the biggest shift.
• Uncertainty can be where you meet your next version of leadership.

Sound Bites

“If I didn’t keep moving, nothing would change.”
“People feed off passion.”
“Rest is the new recipe for leadership.”
“The person you start as is not the person you become.”
“If it doesn’t align, it will not work.”

Episode Chapters

00:00 – Introduction to Lisa Pagotto
02:42 – Lisa’s entrepreneurial journey
04:17 – Shark Tank, visibility and rapid growth
05:10 – A deal collapse and nearly losing the business
06:02 – Pandemic, separation and learning to fly
06:54 – Creating a second business from curiosity
08:08 – Trusting intuition before proof
10:15 – Staying curious when answers are unclear
13:31 – Why women wait for certainty
15:47 – Energy, language and belief
17:03 – Resilience beyond pushing through
20:15 – Reinvention and evolution over ego
22:33 – Alignment, integrity and leaving old roles behind
27:58 – Protecting energy through boundaries
30:55 – Signature questions
34:19 – Final takeaway: start with small movement

About Lisa Pagotto

Lisa Pagotto is the Founder & CEO of Crooked Compass, a multi-award-winning travel brand creating meaningful, immersive and unconventional travel experiences. She is an entrepreneur, speaker, former Shark Tank entrepreneur, and creator of the FIRE Framework — her approach to disruptive leadership, resilience and sustainable growth.

Her work is shaped by lived experience: building businesses through uncertainty, navigating disruption, recovering from setbacks, and continuing to evolve when circumstances change.

Connect & Continue the Conversation

Website: https://www.crooked-compass.com/
LinkedIn: https://www.linkedin.com/in/lisa-pagotto/
YouTube: https://www.youtube.com/@CrookedCompass
Instagram: https://www.instagram.com/lisapagotto_/
Facebook: https://www.facebook.com/Crookedcompasstravel/

Keywords

leadership, uncertainty, resilience, women in leadership, entrepreneurship, courage, reinvention, self-trust, boundaries, sustainable leadership, career growth, values, alignment

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