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
Episodes
1075 episodes
A Day in the Life of a Forward-Deployed Engineer
SUMMARY: What does a Forward-Deployed Engineer actually do? And what about deploying AI Harness? Let’s dig into the real-world with these evolving AI concepts and technologies. SHOW: 1039SHOW TRANSCRIPT:
Chaotic AI Markets: Focus on what you can control
SUMMARY: On Father's Day, how would you explain some of the volatility of the AI market to your father? What advice might he give you to navigate the ups and downs and uncertainties?SHOW: 1038SHOW TRANSCRIPT:
AI Cyber is expanding a Vulnerability Gap
SUMMARY: As tools like Mythos create new AI-cybersecurity concerns, CIOs and CISOs need to be prepared for two challenges: Security Remediation and Patch to Production acceleration. SHOW: 1037SHOW TRANSCRIPT:
Do CIOs need to create an Enterprise AI Harness?
SUMMARY: How can CIOs balance innovation and control as they roll our AI capabilities across their organization. How can they balance onboarding, experience, security and flexibility? SHOW: 1036SHOW TRANSCRIPT:
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 TRANSCRIPT:
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 TRANSCRIPT:
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 O...
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:
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:
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...
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...
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,...
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:
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 P...
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 TRANSCRIPT:
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 engineering—from writing code to orchestrating A...
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 integrating AI agents into development workflo...
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 dynamically managing power systems, we explain how ex...
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:
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: B...
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...
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