The Enterprise AI Show

The Enterprise AI Show explores the AI journey for Enterprise companies around the world. [formerly The Cloudcast]

As the AI revolution moves from experimentation to execution, The Enterprise AI Show provides the clarity needed to lead. Join Aaron Delp and Brian Gracely as they explore the intersection of generative AI, enterprise systems, and global business strategy. Each episode features clear-headed conversations with the people making actual decisions—founders, investors, and practitioners—focusing on the technical architectures and business models that drive real-world ROI.

New shows every Wednesday and Sunday.

Topics: Enterprise AI strategy · The AI Economy · LLMs in production · AI leadership · Agentic AI · Digital Sovereignty · Machine Learning · AI startups · Cloud Computing

Podcasting since 2011 • 1068 episodes

The Enterprise AI Show

Latest Episodes

How will team collaboration evolve within Enterprise AI?

SUMMARY: The biggest enterprise AI question is which organization can most effectively operationalize, govern, and economically scale AI agents across the business.SHOW: 1032SHOW TRANSCRIPT:

May 31, 2026 • 30:56

AI News of the Month - May 2026

SUMMARY: Brian Gracely (@bgracely) and Brandon Whichard (@bwhichard, Software Defined Talk and Failover Media) discuss the biggest AI news stories from the month of May, 2026. SHOW: 1031SHOW TRANSCRIPT:

May 27, 2026 • 37:54

Why Enterprise AI Economics Are Changing

SUMMARY: The biggest enterprise AI question may no longer beWhich model is smartest? Instead, which organization can most effectively operationalize, govern, and economically scale AI agents across the business?’SHOW: 1030SHOW...

May 24, 2026 • 32:28

Can AI Agents be held Accountable?

SUMMARY: As AI Agents are being brought into complex, regulated workflows, we explore the importance of accountability and accuracy, and how platforms and harnesses accomplish that goal. Can the CFO really fall in love with AI? GUES...

May 20, 2026 • 30:06

Enabling AI Governance for M365

SUMMARY: As AI agents become embedded in everyday work, Microsoft 365 governance is no longer a back-office compliance exercise. it’s the “traction control” that lets enterprises innovate faster without losing control of their data, identities,...

May 17, 2026 • 31:43

See All Episodes