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 • 1104 episodes

The Enterprise AI Show

Latest Episodes

AI News for End of September 2026

Brian(@bgracely) and Brandon(@bwhicard) 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. If...

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

How Do Regulated Enterprises Deploy Private, Secure AI?

Aaron interviews Ivan Lee, founder and CEO of Datasaur, about what it takes to build private, secure AI for regulated enterprises. Lee traces the shift away from third-party model reliance to compliance pressure, IP protection, and cost, and fr...

September 23, 2026 • 34:16

AI News for Mid-September 2026

Aaron and Brandon cover what the week's news means for enterprise buyers. They question whether Oracle's reported $664 billion backlog is durable demand or overlapping commitments, and Brandon argues contracted future spend is how enterprise bu...

September 20, 2026 • 42:46

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