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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AI News for End of September 2026

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 read...

4 Loka 35min

The Anthropic IPO?

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 ...

30 Syys 25min

The OpenAI IPO?

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 pro...

27 Syys 28min

How Do Regulated Enterprises Deploy Private, Secure AI?

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 complian...

23 Syys 34min

AI News for Mid-September 2026

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 ...

21 Syys 42min

Building AI Agents That Support Enterprise Teams

Building AI Agents That Support Enterprise Teams

Aaron interviews Diego Oppenheimer, general partner at the AIT Fund (the venture fund behind the AI Tinkerers builder community), about what it takes to move AI agents from personal experimentation in...

16 Syys 39min

Securing AI Agents in the Enterprise: NanoClaw, Zero Trust Guardrails, and Governance at Scale

Securing AI Agents in the Enterprise: NanoClaw, Zero Trust Guardrails, and Governance at Scale

Brian and Aaron interview Gavriel Cohen, co-founder and CEO of Nanoco and creator of the open-source agent framework NanoClaw, about securing AI agents in enterprise environments. Cohen shares how he ...

13 Syys 45min

How Open-Source is Reshaping the AI Infrastructure Stack

How Open-Source is Reshaping the AI Infrastructure Stack

Aaron interviews David Aronchick, CEO @ Expanso (former PM lead for Kubernetes, Kubeflow co-founder, and open-source ML leader at Azure) about how open source is reshaping the AI infrastructure stack....

9 Syys 42min

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