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

In this episode of The Learn-It-All Podcast, host Damon Lembi sits down with Nick Damoulakis, founder and CEO of Orases, recently ranked as the #1 AI and custom software company in the US. Nick’s journey from a college dorm room to leading a nationally recognized tech firm is packed with hard-won lessons on leadership, resilience, and the future of work. The conversation covers everything from Nick’s notorious brush with a Beatles copyright lawsuit to his foundational beliefs on transparency, failing fast, and building teams that weather any storm. Nick also takes us inside the practical steps organizations must take to become truly AI Ready—including why it has to start at the top, and the frameworks he uses to enable company-wide transformation. If you’re passionate about leadership, culture, or the coming wave of AI, you’ll find idea after actionable idea in this episode. 

In this episode, you’ll learn: 

• How Nick turned a college copyright crisis into a launchpad for a thriving tech company. 
• Why vulnerability and transparent failure-sharing are core to building a psychologically safe team. 
• The “bison story” and Nick’s playbook for leading through adversity and economic downturns. 
• Nick’s step-by-step, psychology-driven method for creating real buy-in during major organizational change. 
• What “AI readiness” really means, the three kinds of AI leaders every company needs, and why a Chief AI Officer isn’t a silver bullet. 
• How to spot and empower volunteer innovators, and why small wins are the key to sustainable transformation. 

Timestamps:

00:00 – Three types of AI leaders in organizations 

00:22 – Welcome & Nick’s intro: the path from guitar tabs to CEO 

01:36 – Nick’s first boardroom: sued by Sony & BMG in college 

03:36 – Turning crisis (and near-expulsion) into a full-time tech job 

05:14 – The “Lingo” story: courage, candor, and faking it ‘til you make it 

08:27 – Advice for leaders on stepping out of their comfort zones 

11:44 – Emotional intelligence and social sensitivity in leadership 

14:33 – Surviving downturns: dot-com bust, the Great Recession, COVID 

16:13 – Nick’s framework for helping CEOs correct toxic cultures 

17:15 – When Nick realized he was “the problem” and how he changed 

20:32 – The turning point: recovering from losing $450k in billing 

25:39 – How to prepare for and communicate through scary company meetings 

30:09 – Creating a culture where people never want to let you down 

32:09 – Psychological safety, “oopsies,” and sharing fast failures 

36:09 – How Nick helps teams disrupt themselves and embrace change 

38:59 – Change management, the 8-step model, and enlisting volunteers 

40:29 – AI readiness: why it must come from leadership, not consultants 

43:00 – What incentives, skills, and resources organizations need to make AI practical 

45:48 – Simple wins: Nick’s AI agent example and democratizing innovation 

50:20 – The “Three Buddha Questions” for overcoming any challenge 

 

About Nick Damoulakis 

Nick Damoulakis is the founder and CEO of Orases, named the #1 AI and custom software development company in the US by Clutch and recognized by Gartner as a top 25 emerging specialist consultancy. Nick’s career began in a college computer lab, launching one of the first online guitar tab archives—a venture that earned him fans, a lawsuit from major record labels, and eventually, his first big tech break. Over nearly 25 years, Nick has guided Orases through economic storms, industry disruption, and his own leadership evolution, developing repeatable frameworks for AI transformation...