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
SUMMARY: Brian Gracely (@bgracely) and Brandon Whichard (@bwhichard, Software Defined Talk and Failover Media) discuss the biggest AI news stories from the month of May, 2026.
SHOW: 1031
SHOW TRANSCRIPT: The Reasoning Show #1031 Transcript
SHOW VIDEO: https://youtu.be/MNihDdBSteI
SHOW SPONSORS:
- Nasuni - Activate your data for AI and request a demo
- ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!
SHOW NOTES:
...SUMMARY: The biggest enterprise AI question may no longer be
Which model is smartest? Instead, which organization can most effectively operationalize, govern, and economically scale AI agents across the business?’
SHOW: 1030
SHOW TRANSCRIPT: The Enterprise AI Show #1030 Transcript
SHOW VIDEO: https://youtu.be/acOBfRI0P3U
SHOW SPONSORS:
- ShareGate - ShareGate Protect. Microsoft 365 Governance. We got this.
- Nasuni - Activate your da...
SUMMARY: As AI Agents are being brought into complex, regulated workflows, we explore the importance of accountability and accuracy, and how platforms and harnesses accomplish that goal. Can the CFO really fall in love with AI?
GUEST: Ram Venkatesh, Co-Founder/CTO of Sema4.ai
SHOW: 1029
SHOW TRANSCRIPT: The Enterprise AI Show #1029 Transcript
SHOW VIDEO: https://youtu.be/Lc3XS44Ixg4
SHOW SPONSORS:
- Nasuni - Activate your data for AI...
SUMMARY: As AI agents become embedded in everyday work, Microsoft 365 governance is no longer a back-office compliance exercise. it’s the “traction control” that lets enterprises innovate faster without losing control of their data, identities, and workflows.
GUEST: Richard Harbridge, Principal Industry Advisor, Microsoft 365 at ShareGate
SHOW: 1028
SHOW TRANSCRIPT: The Enterprise AI Show #1028 Transcript
SHOW VIDEO: https://youtu.be/s...
SUMMARY: RIP Reasoning, hello The Enterprise AI Show. We do a point-in-time analysis of the AI market for May 2026, across 11 major categories.
SHOW: 1027
SHOW TRANSCRIPT: The Enterprise AI Show #1027 Transcript
SHOW SPONSORS:
- Nasuni - Activate your data for AI and request a demo
- ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!
SHOW NOTES:
FEEDBACK?
- Email: show @ th...
SUMMARY: We explore one of the most overlooked bottlenecks in the AI boom: energy and infrastructure and why power availability is becoming the limiting factor.
GUEST: Wannie Park, Founder/CEO of PADO AI
SHOW: 1026
SHOW TRANSCRIPT: The Reasoning Show #1026 Transcript
SHOW VIDEO: https://youtu.be/satMQRxKQC8
SHOW SPONSORS:
SUMMARY: Brian Gracely (@bgracely) and Brandon Whichard (@bwhichard, Software Defined Talk and Failover Media) discuss the biggest AI news stories from the month of April, 2026.
SHOW: 1025
SHOW TRANSCRIPT: The Reasoning Show #1025 Transcript
SHOW VIDEO: https://youtu.be/Gl-49dmAgBs
SHOW SPONSORS:
- Nasuni - Activate your data for AI and request a demo
- ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!
SHOW NOTE...
SUMMARY: Draft guru Brandon Whichard (Software Defined Talk) joins us for the inaugural AI Draft, where we predict the next year of AI winners, losers, trends, and headlines.
GUEST: Brandon Whichard, Software Defined Talk
SHOW: 1024
SHOW TRANSCRIPT: The Reasoning Show #1024 Transcript
SHOW VIDEO: https://youtu.be/BjT_HKhOcRE
SHOW SPONSORS:
- ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!
- Nasuni - Activate your da...
SUMMARY: Exploring how to fully embrace AI-driven, agent-based software development, resulting in dramatically increased productivity and faster feature delivery. It highlights a broader shift in engineering—from writing code to orchestrating AI agents.
GUEST: Sam Ramji, CEO/Co-founder at Sailplane
SHOW: 1023
SHOW TRANSCRIPT: The Reasoning Show #1023 Transcript
SHOW VIDEO: https://youtu.be/q50s0oL37pQ
SHOW SPONSORS:
- Nasuni - Activate...
SUMMARY: How software development is rapidly evolving in the age of AI and automation. Matt Moore shares how his team is rethinking secure software supply chains, scaling infrastructure, and safely integrating AI agents into development workflows.
GUEST: Matt Moore, CTO at Chainguard
SHOW: 1022
SHOW TRANSCRIPT: The Reasoning Show #1022 Transcript
SHOW VIDEO: https://youtu.be/9Q0kWkTYRs8
SHOW SPONSORS:
- ShareGate - ShareGate Protect. ...
SUMMARY: How real-time power flow optimization at the edge is helping data centers and the electrical grid handle surging AI energy demands more efficiently. By unlocking hidden capacity and dynamically managing power systems, we explain how existing infrastructure can support significantly more compute without massive new buildouts.
GUEST: Marissa Hummon, CTO Utilidata
SHOW: 1021
SHOW TRANSCRIPT: The Reasoning Show #1021 Transcript
SUMMARY: Shadow AI is growing much faster than known AI adoption across businesses. How can IT teams get Shadow AI under control?
GUEST: Uri Haramati, CEO at Torii
SHOW: 1020
SHOW TRANSCRIPT: The Reasoning Show #1020 Transcript
SHOW VIDEO: https://youtu.be/AUrh_xICPzM
SHOW SPONSORS:
- ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!
- Nasuni - Activate your data for AI and request a demo
SHOW NOTES:
- Torii (home...
SUMMARY: Have we reached a point where coding is a solved problem? And if so, what are the downstream effects on companies that need software to differentiate their business?
GUEST: Brandon Whichard, Co-Host of Software Defined Talk
SHOW: 1019
SHOW TRANSCRIPT: The Reasoning Show #1019 Transcript
SHOW VIDEO: https://youtu.be/q0mksIKcBzk
SHOW SPONSORS:
- ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!
- Nasuni - Activa...
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. M...
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...
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:
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:
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:
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 i...
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:
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