The Enterprise AI Show | Podcast Guru

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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

Recent Episodes

Agents Are Identities Too: Identity Security After CyberArk with Amy Blackshaw

Brandon interviews Amy Blackshaw, Senior Vice President of Identity Marketing at Palo Alto Networks, about identity security in the age of AI agents. Blackshaw, who spent four years leading product marketing at CyberArk before Palo Alto Networks acquired it in February 2026, explains how identity management evolved from an IT operations task into a security discipline, and why identities now need to be protected across their full lifecycle. She walks through the three segments of identity sec...

41 MIN

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 Fight My Monster, one of the first serious production users of Cassandra, to decentralized networks and the founding of DFINITY in 2016. He explains the thesis behind the Internet Computer: a stack of software running down to the silicon can never be ful...

41 MIN

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: developers had gone from an afterthought in technology purchasing to the group whose choices determined what got used, driven first by open source (the LAMP stack, Linux) and then by cloud services like S3 and EC2 that removed the need to ask for budget. The t...

43 MIN

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. If other companies follow, it would point to stress in AI infrastructure commitments, and if not, it is a one-off. Brian suggests the industry needs a "Jenga chart" of whose money is propping up whose, with the contractors who actually pour concrete at the b...

35 MIN

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 of the business in the current and potentially future political climates in the US and around the world. SHOW: 1067 SHOW TRANSCRIPT: The EntAIShow #1067 - The Anthropic IPO? SHOW SPONSORS Nasuni - Activate your data for AI and request a demoNordLay...

25 MIN