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    News

    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 

    Advertise

    Copyright: © 2024 Massive Studios

    • Apple Podcasts
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    Latest Episodes:
    RAG Won’t Save Your Messy Data: The Brutal Truth About AI Reliability Apr 12, 2026
    Show notes

    SUMMARY: The RAG (Retrieval Augmented Generation) pattern is one of the most frequently used to augment LLMs with context-specific information. Let’s explore RAG.

    GUEST: Roie Schwaber-Cohen, Head of Developer Relations at Pinecone

    SHOW: 1018

    SHOW TRANSCRIPT: The Reasoning Show #1018 Transcript

    SHOW VIDEO: https://youtu.be/-kZZEMR341Q

    SHOW SPONSORS:

    • Nasuni - Activate your data for AI and request a demo
    • ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!

    SHOW NOTES:

    Topic 1 - Welcome to the show. Tell us a little bit about your background, and what you focus on these days at Pinecone

    Topic 2 - Let’s begin by talking about RAG systems. What are they? Why do companies choose to use them? What benefits do they provide in AI systems?

    Topic 3 - At a high level, RAG sounds straightforward—retrieve relevant context, generate an answer. But in practice, where does it break first as systems scale?

    Topic 4 - I’ve heard that RAG systems can return answers that are technically correct but fundamentally wrong. What’s a concrete example of that happening in production—and why does it slip past most teams?

    Topic 5 - In traditional systems, we assume there’s a single source of truth. But in enterprise environments, ‘truth’ is often versioned, contextual, and conflicting. How should teams rethink ‘truth’ when building AI systems?

    Topic 6 - A lot of teams assume their knowledge base is ‘good enough’ for RAG. What do they usually underestimate about the messiness of real enterprise data?

    Topic 7 - There’s a growing narrative that better reasoning models can compensate for weaker retrieval. From what you’ve seen, where does that idea fall apart?

    Topic 8 - If correctness depends on things like timing, policy scope, or configuration, how should teams design systems that understand context—not just content?

    Topic 9 - Looking ahead, what replaces today’s RAG architectures? What patterns are emerging among teams that are actually getting this right?”


    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    The Productivity Paradox: Why More AI Code is Slowing Down Shiptimes Apr 08, 2026
    Show notes

    SUMMARY: Discover how AI is transforming software development and what it means for engineering leaders.

    GUEST: Jeff Keyes, Field CTO at AllStacks

    SHOW: 1017

    SHOW TRANSCRIPT: The Reasoning Show #1017 Transcript

    SHOW VIDEO: https://youtu.be/cXPu8iWeB0k

    SHOW SPONSORS:

    • ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!
    • Nasuni - Activate your data for AI and request a demo

    SHOW NOTES:

    Topic 1 - Welcome to the show. Tell us a little bit about your background, and what you focus on these days at AllStacks.

    Topic 2 - You’ve been talking to a lot of engineering leaders using AI coding tools—what’s the most surprising gap you’re seeing between increased code generation and actual delivery outcomes?

    Topic 3 - Why does increasing developer output with AI often lead to more debugging, duplication, or cleanup instead of faster delivery?

    Topic 4 - You’ve described an ‘invisible rework loop’—can you walk us through what that looks like inside a modern engineering team?

    Topic 5 - As code generation gets easier, where does the real bottleneck shift in the software delivery lifecycle?

    Topic 6 - How do unclear product or engineering specifications get amplified in an AI-assisted development environment?

    Topic 7 - If traditional metrics like lines of code or velocity are becoming misleading, what should engineering leaders actually measure to know if AI is improving delivery?

    Topic 8 - What does a ‘healthy’ AI-assisted development workflow look like 12–18 months from now?


    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    The Production Chaos: Why AI-Generated Code is Breaking Traditional SRE Apr 05, 2026
    Show notes

    SUMMARY: With the explosion of AI-generated code and applications, the modern SRE requires an AI-native approach to managing complex systems.

    GUEST: Anish Agarwal - CEO/Cofounder of Traversal

    SHOW: 1016

    SHOW TRANSCRIPT: The Reasoning Show #1016 Transcript

    SHOW VIDEO: https://youtu.be/hF3MCRDhMno

    SHOW SPONSORS:

    • Nasuni - Activate your data for AI and request a demo
    • ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!

    SHOW NOTES:

    • Traversal (homepage)

    Topic 1 - Welcome to the show. Tell us a little bit about your background, and what you focus on these days at Traversal.

    Topic 2 - AI is dramatically accelerating code generation, but not improving production outcomes. What’s fundamentally breaking in the traditional SRE model—and where do you see the biggest friction between speed and reliability?

    Topic 3 - What are the most common failure patterns or mistakes you’re seeing in production from AI-generated code—and what’s driving them?

    Topic 4 - AI can generate functional code, but it often lacks context about how systems behave in production. How is this changing what ‘good observability’ needs to look like?

    Topic 5 - How do you see SRE evolving in an AI-first world? Does it become more automated, more policy-driven, or even partially autonomous?

    Topic 6 - For organizations that want to embrace AI-assisted development but avoid production chaos, what are the most important guardrails they should put in place?

    Topic 7 - If we fast-forward 2–3 years, what does a ‘modern’ production stack look like in a world where most code is AI-generated? What capabilities become absolutely essential? In one sentence—what’s the #1 thing a CTO should do right now?

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    The Future of Service belongs to Self-Improving AI Apr 01, 2026
    Show notes

    SUMMARY: Today’s episode is all about a transformation happening in customer service—one that’s moving us from static systems and scripted workflows into something far more dynamic: AI systems that can actually learn and improve over time.

    GUEST: Shashi Upadhyay (President of Product, Engineering, and AI at Zendesk)

    SHOW: 1015

    SHOW TRANSCRIPT: The Reasoning Show #1015 Transcript

    SHOW VIDEO: https://youtu.be/IQaxE-DjIpo

    SHOW SPONSORS:

    • ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!
    • Nasuni - Activate your data for AI and request a demo

    SHOW NOTES:

    • The future of service belongs to self-improving AI

    Topic 1 - Welcome to the show. Tell us a bit about your background and your focus today.

    Topic 2 - You describe this moment as a shift from systems of record to intelligent systems of action. What’s fundamentally broken in today’s customer service model that’s forcing this transition now? What changed in the last 2–3 years to make this possible?

    Topic 3 - There’s been a lot of AI in customer service that overpromised and underdelivered. What are the biggest gaps between what customers actually need—like resolution—and what legacy automation has been delivering?

    Topic 4 - The concept of a “self-improving” system is really powerful. What’s actually new here—what enables AI to improve with every interaction without constant human tuning?

    Topic 5 - You’ve moved from assistive copilots to what you call “agentic AI” that can resolve issues end-to-end. Where are we today on that journey—and what still requires human involvement?

    Topic 6 - Voice has historically been one of the hardest channels to automate. What changes with this new generation of AI that makes even complex, multi-step voice interactions solvable?

    Topic 7 - If we fast-forward 2–3 years, what does a “best-in-class” customer service experience look like in an AI-first world?

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    The $26B Pivot: Why Big Tech is Abandoning the AI "Wrapper" Model Mar 29, 2026
    Show notes

    SUMMARY: Brian (@bgracely) and Brandon Whichard (@bwhichard, Software Defined Talk and Failover Media) discuss the biggest AI news stories from the month of March, 2026.

    SHOW: 1014

    SHOW TRANSCRIPT: The Reasoning Show #1014 Transcript

    SHOW VIDEO: https://youtu.be/XwyAC-hxOQY

    SHOW SPONSORS:

    • VENTION - Ready for expert developers who actually deliver?
      Visit ventionteams.com

    SHOW NOTES:

    • Links to all the AI News covered in this months show

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    Living the Claude-centric Life Mar 25, 2026
    Show notes

    SUMMARY: With @bwhichard, we dig into how daily work-life changes when you make @AnthropicAI @claudeai the center of all workflow activities.

    SHOW: 1013

    SHOW TRANSCRIPT: The Reasoning Show #1013 Transcript

    SHOW VIDEO: https://youtu.be/zEmEH0t67js

    SHOW SPONSORS:

    • VENTION - Ready for expert developers who actually deliver?
      Visit ventionteams.com

    SHOW NOTES:

    Topic 1 - How long have you been living the Claude-life, and when did it dawn on you to make this central to your day-to-day activities?

    Topic 2 - What were the biggest hurdles you had to overcome before you trusted the system and started letting it have ownership over tasks and workflows?

    Topic 3 - What are some of your best practices in terms of machine setup, how or where you store data, how you decide what to give it access to? Walk me through your thoughts around things like keeping things simple, where to be complex, how you think about security, etc.

    Topic 4 - How are you learning to give it more responsibilities, or just figure out new ways to be productive with it?

    • Good resources you’re pulling from?
    • Any tips to make it use less tokens?
    • Skills marketplaces?

    Topic 5 - What have been some of the biggest barriers to successful adoption, or just areas where you’re still struggling to get it to do the things you want? Or are you still in the learning curve stage and things just keep growing on one another?

    Topic 6 - If you took the knowledge and skills you have now in Claude-life into your day-job, how do you see yourself working, as well as working with the rest of your team/teams? Would it bother you if you didn’t think they were using AI tools as much?


    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    NVIDIA’s Open Software Trap: The Real Cost of the New Inference Stack Mar 22, 2026
    Show notes

    SUMMARY: We dig into the NVIDIA GTC keynote and highlight three things - accelerated computing for everything, the complexity of the new inference stack, and NVIDIA’s “open” software stack including NemoClaw.

    SHOW: 1012

    SHOW TRANSCRIPT: The Reasoning Show #1012 Transcript

    SHOW VIDEO: https://youtu.be/aXOr91q76yM

    SHOW SPONSORS:

    • VENTION - Ready for expert developers who actually deliver?
      Visit ventionteams.com

    SHOW NOTES:

    • NVIDIA GTC 2026 (Keynote)
    • NVIDIA NemoClaw - OpenClaw + OpenShell + NVIDIA Agent Toolkit
    • NVIDIA adds Groq LPU to their rack systems
    • NVIDIA to invest $26B in Open Weight Models
    • Interview with Jensen about Accelerated Computing (Stratechery)


    Topic 1 - Jensen’s trying to paint the bigger picture of accelerated computing everywhere (robotics, autonomous driving, gen-ai, physical ai - but also just everyday enterprise apps). Everything is about keeping the stock price up, and margins high. The stock price provides the warchest to fight off all foes.

    Topic 2 - The inference architecture is a complex mix of GPUs, CPUs, ASICs/LPUs, high-speed networking and seems very different from the training architecture. How big is the burden on data center providers? What are the inference alternatives emerging?

    Topic 3 - Jensen talked a lot about OpenClaw and eventually about NVIDIA’s NemoClaw. How does his interest in Agentic AI tie into his interest in building NVIDIA’s own frontier model


    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    Kagenti - A Kubernetes Control Plane for AI Agents Mar 18, 2026
    Show notes

    SUMMARY: Morgan Foster talks about the Kagenti project, which enables an AI Agent agnostic framework for security, authentication, identity and zero-trust.

    SHOW: 1011

    SHOW TRANSCRIPT: The Reasoning Show #1011 Transcript

    SHOW VIDEO: https://youtu.be/djFZruLEDiw

    SHOW NOTES:

    • Kagenti (homepage)
    • Kagenti (use-cases)
    • “Old Things that look like Agents”
    • “What makes Agents different?”
    • CNV - What Makes Agents Different?
    • “Handing your phone to a stranger, why Agents need their own identity”


    Topic 1 - Welcome to the show. Tell us a little bit about your background and areas you focus on today.

    Topic 2 - Tell us a bit about the Kagenti project and the types of challenges it’s trying to solve for Agentic AI deployments.

    Topic 3 - How much commonality exists between different Agentic frameworks that a common, agnostic agentic orchestration approach can work? And how much difference still exists and would drive companies to silo’d deployments?

    Topic 4 - How far should an Agentic Orchestration framework go, and what types of things do you expect will still be Agentic framework dependent?

    • Is Kagenti more of a control-plane element, or more of a data-plane element?

    Topic 5 - As Kagenti evolves, what are some of the adjacent things that people should be keeping an eye on that might be a dependency, or could shift the direction of the project?

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    Your Career is Legacy Code: Why 'All Jobs are Software' is a Warning, Not a Trend Mar 15, 2026
    Show notes

    SUMMARY: Brian talks about the rapidly expanding gap between people and companies that augment their work with AI and those who are making AI the center of their work world.

    SHOW: 1010

    SHOW TRANSCRIPT: The Reasoning Show #1010 Transcript

    SHOW VIDEO: https://youtu.be/tFyLlCnkbsM

    SHOW SPONSORS:

    • VENTION - Ready for expert developers who actually deliver?
      Visit ventionteams.com

    SHOW NOTES:

    WHY THE NEED FOR A CODE RED?

    • Velocity of Code (new companies)
    • Velocity of Productivity (employees)
    • Velocity of Analysis (strategy)
    • AgentOps
    • Token Factories
    • Devs for Business, Re-Wiring the Concept of Business Analyst

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

    Inside OpenClaw and Open Source Innovation Mar 11, 2026
    Show notes

    SUMMARY: Sally O’Malley (Principle Software Engineer @RedHat, Maintainter @OpenClaw) talks about her early experiences of immersing herself into OpenClaw and evolution of the OpenClaw community.

    SHOW: 1009

    SHOW TRANSCRIPT: The Reasoning Show #1009 Transcript

    SHOW VIDEO: https://youtu.be/7xARBtgiMQg

    SPONSORS:

    • VENTION - Ready for expert developers who actually deliver?
      Visit ventionteams.com

    SHOW NOTES:

    • OpenClaw - Personal AI Assistant
    • OpenClaw - Reddit
    • OpenClaw, OpenAI and the Future (Peter Steinberger - OpenClaw creator)
    • OpenClaw Foundation (coming soon)


    Topic 1 - Welcome to the show. Tell us a little bit about your background in software engineering.

    Topic 2 - You recently jumped into the deep end of the pool with OpenClaw. Tell us about the week of immersion with this new technology.

    • What did you go into it thinking about?
    • What did you learn, what did you create?
    • What new sorts of things did you have to try?

    Topic 2a - For anyone that’s new to OpenClaw, can you give us the basics of what OpenClaw does?

    Topic 3 - You mentioned that this is a very different (or completely different) paradigm of how software is created. Can you walk us through the differences, your observations, how you had to really rethink things that you did before and after?

    Topic 4 - In your day job, you’re focused on software that’s used by large enterprises that have to be concerned with security and stability, as much as they do innovation. How do you see the existing OpenClaw fitting into that world?

    • How do you expect that OpenClaw might need to change?
    • How do you expect that enterprises might need to change to adapt to this new capability that might be unleashed with their employees?

    Topic 5 - You (very) recently were accepted as a committer to the OpenClaw project. I know it’s only been a few days, but what is opening your eyes about how this community operates, especially in comparison to other open projects you’ve worked on?

    • We could probably have an entire podcast on AI development in open communities.

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow

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