214: What Happened When This CEO Faced His Own Toxic Leadership | Nick Damoulakis

Nick Damoulakis, founder and CEO of Orases, has led his company from a college dorm room startup to being ranked the #1 AI and custom software company in the US. Recognized by Gartner as a top 25 emerging specialist consultancy, Nick is known for his candid stories and repeatable frameworks for AI transformation, leadership resilience, and culture building. In this episode, host Damon Lembi and Nick explore how leaders can navigate failure, foster psychological safety, and take practical steps toward true AI readiness. From turning a Beatles copyright lawsuit into a career launchpad to guiding organizations through economic storms, Nick’s journey is filled with real-world insights you can apply immediately.

Read the full breakdown of Nick’s episode on Learnit.

Key Leadership Lessons from Nick Damoulakis’s Journey:

• How vulnerability and transparent failure-sharing strengthen trust and psychological safety

• Why AI readiness must start with leadership and the three types of AI leaders every company needs
  Nick’s frameworks for leading through crises, enlisting volunteers for change, and building cultures that thrive under pressure

Connect with Nick Damoulakis:

• Website: Orases

• LinkedIn: Nick Damoulakis

Nick Damoulakis is a recognized thought leader in AI readiness and organizational transformation. His insights have been featured in Gartner and Clutch, as well as CEO peer networks like Vistage.

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