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 • 1106 episodes

The Enterprise AI Show

Latest Episodes

A Cloud Nobody Owns: Sovereign Infrastructure for the Agent Era with Dominic Williams

Brandon interviews Dominic Williams, founder, president, and chief scientist of the DFINITY Foundation, about the Internet Computer and why he set out to build a new back-end compute stack. Williams traces his path from building the kids' MMO F...

October 11, 2026 • 41:45

The New, New Kingmakers: Agents, Developers, and the Future of Software with Stephen O'Grady

Brandon interviews Stephen O'Grady, principal analyst and co-founder of RedMonk, about his 2013 book *The New Kingmakers* and his recent follow-up, "Agents: The new, New Kingmakers." O'Grady explains that the original thesis was simple: develop...

October 07, 2026 • 43:03

AI News for End of September 2026

Brian (@bgracely) and Brandon (@bwhichard) discuss the biggest AI news stories from the second half of September 2026.Oracle sent a force majeure notice on a major data center build, which Brandon reads as an early signal worth tracking....

October 04, 2026 • 35:04

The Anthropic IPO?

We review the potential Anthropic IPO, in the context of revenue trajectory, expense trajectory and planned commitments, past and future funding rounds, future expanse commitments to large datacenter projects, and the strengths and weaknesses o...

September 30, 2026 • 25:10

The OpenAI IPO?

We review the potential OpenAI IPO, in the context of revenue trajectory, expense trajectory and planned commitments, past and future funding rounds, future expanse commitments to large datacenter projects, and the strengths and weaknesses of t...

September 27, 2026 • 28:52

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