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

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Episoder(1089)

Can AI Agents be held Accountable?

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 r...

20 Mai 30min

Enabling AI Governance for M365

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 witho...

17 Mai 31min

An AI Market Analysis, May 2026

An AI Market Analysis, May 2026

SUMMARY: RIP Reasoning, hello The Enterprise AI Show. We do a point-in-time analysis of the AI market for May 2026, across 11 major categories. SHOW: 1027 SHOW TRANSCRIPT: The Enterprise AI Show #102...

13 Mai 40min

AI, Data Centers, and the Power Crunch

AI, Data Centers, and the Power Crunch

SUMMARY: We explore one of the most overlooked bottlenecks in the AI boom: energy and infrastructure and why power availability is becoming the limiting factor. GUEST: Wannie Park, Founder/CEO of PA...

10 Mai 33min

AI News of the Month for April 2026

AI News of the Month for April 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 April, 2026. SHOW: 1025 SHOW TRAN...

6 Mai 37min

The 2026 AI Draft

The 2026 AI Draft

SUMMARY: Draft guru Brandon Whichard (Software Defined Talk) joins us for the inaugural AI Draft, where we predict the next year of AI winners, losers, trends, and headlines. GUEST: Brandon Whichard,...

3 Mai 43min

Halt & Retool: Rewriting Software Development in the Age of AI Agents

Halt & Retool: Rewriting Software Development in the Age of AI Agents

SUMMARY: Exploring how to fully embrace AI-driven, agent-based software development, resulting in dramatically increased productivity and faster feature delivery. It highlights a broader shift in engi...

29 Apr 34min

The Zero-CVE Mirage: Hardening Software in the Age of AI Attacks

The Zero-CVE Mirage: Hardening Software in the Age of AI Attacks

SUMMARY: How software development is rapidly evolving in the age of AI and automation. Matt Moore shares how his team is rethinking secure software supply chains, scaling infrastructure, and safely in...

26 Apr 35min

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