The Enterprise AI Show
Massive Studios
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About This Podcast
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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Recent Episodes
Should CIOs have a backup plan for AI?
SUMMARY: If the cost of public AI continues to rise, because of various market shortages, should CIOs start looking at backup plans to better own their AI journeys and futures?SHOW: 1035SHOW…
What are the incentives to share AI learning curves with teammates?
SUMMARY: When we get to the end of 2026, how will enterprise companies be measuring the success of their AI projects? And how well will their teams be sharing their AI learning curves?SHOW: 1034SHOW…
Cerebras is disrupting the market with Fast Inference
SUMMARY: After the first successful AI IPO of 2026, we dig into what makes the Cerebras WSE architecture unique in the market for fast inference. GUEST: Andy Hock, Chief Strategy Officer at Cerebras…
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: The…
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…
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…
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…
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…
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: 1027SHOW TRANSCRIPT: The Enterprise AI Show #1027…
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…
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: 1025SHOW…
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,…
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…
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…
The Grid’s Breaking Point: Can AI Save the Infrastructure It’s About to Crash?
SUMMARY: How real-time power flow optimization at the edge is helping data centers and the electrical grid handle surging AI energy demands more efficiently. By unlocking hidden capacity and…
Shadow AI is Faster Than Your Governance: Why Guardrails are Failing
SUMMARY: Shadow AI is growing much faster than known AI adoption across businesses. How can IT teams get Shadow AI under control?GUEST: Uri Haramati, CEO at ToriiSHOW: 1020SHOW TRANSCRIPT: The…
The Junior Dev Crisis: Who Inherits the Code When AI Does the Work?
SUMMARY: Have we reached a point where coding is a solved problem? And if so, what are the downstream effects on companies that need software to differentiate their business?GUEST: Brandon Whichard,…
RAG Won’t Save Your Messy Data: The Brutal Truth About AI Reliability
SUMMARY: The RAG (Retrieval Augmented Generation) pattern is one of the most frequently used to augment LLMs with context-specific information. Let’s explore RAG. GUEST: Roie Schwaber-Cohen, Head of…
The Productivity Paradox: Why More AI Code is Slowing Down Shiptimes
SUMMARY: Discover how AI is transforming software development and what it means for engineering leaders. GUEST: Jeff Keyes, Field CTO at AllStacks SHOW: 1017SHOW TRANSCRIPT: The Reasoning Show #1017…
The Production Chaos: Why AI-Generated Code is Breaking Traditional SRE
SUMMARY: With the explosion of AI-generated code and applications, the modern SRE requires an AI-native approach to managing complex systems. GUEST: Anish Agarwal - CEO/Cofounder of TraversalSHOW:…
Frequently Asked Questions
The Enterprise AI Show has published 1071 episodes since February 2011, covering topics in Business, Management.
The Enterprise AI Show is currently highly active with new episodes every few days. Average episode length is 31m.
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