STR Global Unlocked with Simon Lehmann: Unfiltered knowledge for the short term rental industry

022: Why STR Leaders Crack Under Pressure | CEO Coach Gary Cohen

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0:00 | 47:02

As short-term rental moves from rapid expansion into a more disciplined phase, leadership quality becomes the differentiator.

In fast-scaling STR businesses, execution rarely breaks because of strategy. It breaks under pressure, idea overload, unclear decision rights, and human blind spots.

In this episode of STR Global Unlocked, Simon Lehmann speaks with Gary Cohen, CEO coach and leadership advisor, about what actually changes in founders when complexity increases.

They examine why scaling without documentation weakens execution, how ego and humility shape decision quality, and why many STR operators become the bottleneck in their own companies.

The conversation also explores how leaders should think about AI, not as advanced search, but as a strategic thinking partner in an evolving discovery landscape.

In this conversation, we discuss:

  • Why short term rental leadership failures often begin with human behavior, not financial performance.
  • How scaling STR companies must balance business systems, team dynamics, and executive self awareness.
  • Where decisiveness becomes reactive decision making and how idea overload damages operational clarity.
  • The relationship between ego, humility, and executive effectiveness in fast growing hospitality businesses.
  • How AI is reshaping decision making, search visibility, and strategic leadership in short term rental.

Resources and links:

Connect with Gary Cohen on LinkedIn [https://www.linkedin.com/in/garycohen/] to learn more about CO2 Coaching [https://co2coaching.com].  

Resources

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