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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The 5-10-85 Reality of Enterprise AI

The 5-10-85 Reality of Enterprise AI

Three years since the launch of ChatGPT, what does the landscape of Enterprise AI look like today? What’s working, what’s struggling and what’s still unknown? SHOW: 966 SHOW TRANSCRIPT: The Cloudcast ...

12 Loka 202527min

Using AI Reasoning to Prevent AI Scams

Using AI Reasoning to Prevent AI Scams

Alan Lefort (CEO, @StrongestLayer) discusses how LLM-powered reasoning is transforming phishing security from reactive pattern-matching to predictive threat detection, and why traditional rule-based s...

8 Loka 202534min

Will Cloud Providers start acquiring SaaS?

Will Cloud Providers start acquiring SaaS?

As cloud matures, could the hyperscale cloud providers start looking to acquire SaaS providers to build out a bundled application portfolio? Or are the demands of AI investment too much to pursue that...

5 Loka 202528min

AI & Cloud Trends for September 2025

AI & Cloud Trends for September 2025

Brian Gracely (@bgracely) and Brandon Whichard (@bwhichard, @SoftwareDefTalk) discuss the top stories in Cloud and AI from September 2025. SHOW: 963 SHOW TRANSCRIPT: The Cloudcast #963 Transcript SHOW...

1 Loka 202543min

The AI Awkward Years

The AI Awkward Years

Between the bold predictions, VC economics, and rising usage-patterns are stories of limited ROIs, undefined use-cases and associated job losses. AI is in an awkward phase of maturity and it’s not cle...

28 Syys 202527min

AI Agents for Unstructured Data

AI Agents for Unstructured Data

Stephan Donze (@sdonze CEO @AODocs), discusses the enterprise unstructured data crisis, where 80% of business data remains untapped due to legacy system limitations and the challenges of AI-powered do...

24 Syys 202526min

Two Obseervations about Smart People and AI

Two Obseervations about Smart People and AI

How is it possible that smart people both love and hate AI? Does it matter how smart you are, or just how you interact with AI? SHOW: 960 SHOW TRANSCRIPT: The Cloudcast #960 Transcript SHOW VIDEO: ht...

21 Syys 202523min

The Return of Bare Metal?

The Return of Bare Metal?

Todd Robinson, Founder and President of OpenMetal.io, discusses the resurgence of bare metal infrastructure driven by AI workloads, digital sovereignty requirements, and companies reassessing public c...

17 Syys 202528min

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