In this episode of Business Uncomplicated, Rich Nazzaro sits down with innovation strategist and author Steve Wunker, Managing Director at New Markets Advisors and author of AI and the Octopus Organization: Building the Super Intelligent Firm.

They explore how AI can do far more than automate tasks—it can fundamentally reshape how your organization thinks, decides, and acts. Using the octopus as a metaphor (nine brains, eight tentacles, three hearts), Steve explains what it really means to build a firm that’s fast, adaptive, and intelligent at every node, not just at the top.

Together, Rich, Steve, and co-host Andy Worobel dig into why so many AI efforts stall at “pilot theater,” how to move from tools to true transformation, and what this means for leaders, middle managers, and frontline teams.

Get your copy of: AI and the Octopus Organization: Building the Superintelligent Firm 

In this episode, we cover:

• The Octopus Organization metaphor
  How nine brains and eight tentacles map to AI-enabled decision-making at the edge of your business.

• Why most AI initiatives fall flat
  Pilot overload, narrow thinking, and the trap of sprinkling AI across 17 steps instead of redesigning the process.

• Transformation vs. technology
  Why “buying the tool” (Salesforce, AI platforms, etc.) without a clear why leads to shallow change and wasted spend.

• Starting with the customer, not the model
  How reimagining growth, customer value, and competitive strategy should precede any AI deployment.

• Bottom-up autonomy and the new frontline
  How AI finally makes it possible to devolve authority—with real context, guardrails, and feedback loops.

• The reinvention of the middle manager
  Moving from admin and coordination to steward of the model, coach, and day-to-day change manager.

• Breaking silos without becoming a micromanager
  How AI-driven transparency can unite marketing, sales, ops, and IT—without turning leadership into “radio-era admirals” meddling in everything.

• The CIO’s once-in-a-generation moment
  Why this may be the best time in history for IT to lead organizational transformation—and what that partnership with the business should look like.

• Energy, infrastructure, and the real constraints on AI
  Why the current path of hyperscale models is unsustainable and how leaner, purpose-built models may shape the future.

• Democratizing data and tools
  From “everyone build a GPT” chaos to intentional productization and access to the right data sources with the right guardrails.

• Why most companies are terrible at experimentation
  Zombie projects, poor learning loops, and how to design AI experiments that actually move the needle.

If you’re an executive, CIO, or operator trying to move past AI hype and into real, structural change, this conversation gives you both the language and the lenses to start redesigning your organization.