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
1103 episodes
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...
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...
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...
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...
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 into enterpr...
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 share...
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 infrastructu...
Vitamins vs. Pain Killers vs. Whippets - The Enterprise AI Adoption Problem
Brian, Brandon, and Aaron discuss enterprise AI adoption using the sales analogy of whether AI is a “vitamin” or a “painkiller,” arguing that successful transformation still requires a burning-platform event. Brandon suggests AI adoption resemb...
AI News of the Month - August 2026
Aaron, Brian, and Brandon cover major stories including NVIDIA’s record quarter and continued growth forecasts, alongside concerns about declining free cash flow and customer financing. They discuss NVIDIA’s reported $12.9B acquisition of Huggi...
AI Watermarking: Compliance Theater or Real Provenance Tool
SUMMARY: Brian, Brandon, and Aaron focus on AI watermarking, driven largely by EU transparency requirements, and discuss how approaches like token-selection patterns can be detected but were reportedly cracked quickly with tools that strip wate...
Your AI Project Doesn't Need More Agents
SUMMARY: Brandon speaks with Rich Ziade, co-founder and CEO of Aboard, about why enterprise AI projects fail without real discovery, why "agents" have been oversold as a headcount play, and why organizational urgency, not new tooling, is what a...
NVIDIA's Pivot from Chipmaker to Financier
SUMMARY: Brian, Brandon, and Aaron discuss news about Nvidia’s reported $105B backing of OpenAI’s Ohio data center and what it implies for GPUs as an “asset class” and enterprise AI. Brian argues Jensen Huang is shifting Nvidia’s narrative from...
Own Your AI Weights or Rent Them?
SUMMARY: Brandon and Aaron discuss the pros and cons of owning or renting your model weights. What does that mean for the Enterprise, and what should you be considering?SHOW: 1055SHOW TRANSCRIPT:
Will OSS Models Take Over?
SUMMARY: This episode is the second part and explores the flip side of OSS models. Last episode, we discussed the potential decline; this episode, we’ll talk about the potential positive future of OSS models. Aaron and Brandon explore the futur...
Are We Seeing The End Of OSS Models?
SUMMARY: In this episode, Aaron and Brandon explore the potential decline of open-source models in AI, discussing market trends, financial challenges, and the future of OSS in the AI landscape.SHOW: 1053SHOW TRANSCRIPT:
The Zitron Bear Case: What's Right, What's Wrong?
SUMMARY: In this episode, Aaron and Brandon tackle the provocative critiques of AI by Ed Zitron, a vocal opponent in the tech industry. They delve into the bear case against AI, exploring both the merits and flaws of Zitron's views.SHOW:...
Do You Even Need That Trillion-Parameter Model?
SUMMARY: We continue our Models and Money series. In this episode, Brian and Aaron explore the current state and future of AI models, focusing on model size, model harnessing, and intelligent model routing. They discuss whether bigger models ar...
AI News of the Month - July 2026
SUMMARY: Brian Gracely (@bgracely) and Brandon Whichard (@bwhichard) discuss the biggest AI news stories from the month of July 2026. SHOW: 1050SHOW TRANSCRIPT:
How AI Stacks are rewriting the Rules of Business
SUMMARY: Brian speaks with Dave Vellante, Co-Founder/CEO theCUBE, about how AI is changing the entire tech stack, the evolution of systems of intelligence, and how the competitive landscape i...
When Will the Models be Good Enough?
SUMMARY: Brian and Aaron explore the current state and future of AI models, focusing on model size, model harnessing, and intelligent model routing. They discuss whether bigger models are always better, the economics of AI, and how enterprise a...
AI's Impact on Trust and Brand
SUMMARY: Brian talks with Melissa Rosenthal from Outlever about the intersection of AI, brand, and marketing. They explore how AI impacts trust, brand consistency, and operational efficiency, offering insights for organizations navigating AI ad...
What is a Behavioral Agent Automation Platform?
SUMMARY: Steven Walchek, CEO at Liminal, discusses secure AI enablement for regulated industries and why most enterprises are stuck in perpetual AI pilots. We explore the "agentic cliff" and how Behavioral Agent Automation Platforms (BAAPs) dis...
Does FinOps need an update for the AI world?
SUMMARY: On today’s "Models and Markets" - we explore about the FinOps experience from Cloud is having to adapt to the changing demands of Enterprise AI. SHOW: 1045SHOW TRANSCRIPT: