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: As AI within the Enterprise matures, we look at 10 concerns and challenges that are still causing Chief AI Officers to worry about success in the future.
SHOW: 1040
SHOW TRANSCRIPT: The Enterprise AI Show #1040 Transcript
SHOW VIDEO: https://youtu.be/RyB4m17YK_4
SHOW SPONSORS:
- Nasuni - Activate your data for AI and request a demo
- OutShift by Cisco - “Scaling Out Superintelligence” The Internet of Cogn...
SUMMARY: What does a Forward-Deployed Engineer actually do? And what about deploying AI Harness? Let’s dig into the real-world with these evolving AI concepts and technologies.
SHOW: 1039
SHOW TRANSCRIPT: The Enterprise AI Show #1039 Transcript
SHOW VIDEO: https://youtu.be/QY0fqu2O84M
SHOW SPONSORS:
- OutShift by Cisco - “Scaling Out Superintelligence” The Internet of Cognition architecture
- ShareGate - Sha...
SUMMARY: On Father's Day, how would you explain some of the volatility of the AI market to your father? What advice might he give you to navigate the ups and downs and uncertainties?
SHOW: 1038
SHOW TRANSCRIPT: The Enterprise AI Show #1038 Transcript
SHOW VIDEO: https://youtu.be/T2ZIYLpl_cE
SHOW SPONSORS:
- ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!
- Nasuni - Activate your data for AI and request a demo
- OutShif...
SUMMARY: As tools like Mythos create new AI-cybersecurity concerns, CIOs and CISOs need to be prepared for two challenges: Security Remediation and Patch to Production acceleration.
SHOW: 1037
SHOW TRANSCRIPT: The Enterprise AI Show #1037 Transcript
SHOW VIDEO: https://youtu.be/H5KxoiEIfUo
SHOW SPONSORS:
- Nasuni - Activate your data for AI and request a demo
- OutShift by Cisco - “Scaling Out Superintelligence” T...
SUMMARY: How can CIOs balance innovation and control as they roll our AI capabilities across their organization. How can they balance onboarding, experience, security and flexibility?
SHOW: 1036
SHOW TRANSCRIPT: The Enterprise AI Show #1036 Transcript
SHOW VIDEO: https://youtu.be/ZgkMF7G3Yfo
SHOW SPONSORS:
- OutShift by Cisco - “Scaling Out Superintelligence” The Internet of Cognition architecture
- ShareGate - Sh...
SUMMARY: If the cost of public AI continues to rise, because of various market shortages, should CIOs start looking at backup plans to better own their AI journeys and futures?
SHOW: 1035
SHOW TRANSCRIPT: The Enterprise AI Show #1035 Transcript
SHOW VIDEO: https://youtu.be/ngBBpP2Lgdo
SHOW SPONSORS:
- ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!
- Nasuni - Activate your data for AI and request a demo
- OutShift by C...
SUMMARY: When we get to the end of 2026, how will enterprise companies be measuring the success of their AI projects? And how well will their teams be sharing their AI learning curves?
SHOW: 1034
SHOW TRANSCRIPT: The Enterprise AI Show #1034 Transcript
SHOW VIDEO: https://youtu.be/TvIFwNN-6ck
SHOW SPONSORS:
- Nasuni - Activate your data for AI and request a demo
- OutShift - “Scaling Out Superintelligence” The Internet ...
SUMMARY: After the first successful AI IPO of 2026, we dig into what makes the Cerebras WSE architecture unique in the market for fast inference.
GUEST: Andy Hock, Chief Strategy Officer at Cerebras AI
SHOW: 1033
SHOW TRANSCRIPT: The Enterprise AI Show #1033 Transcript
SHOW VIDEO: https://youtu.be/ed2nVbOtZiA
SHOW SPONSORS:
- OutShift - “Scaling Out Superintelligence” The Internet of Cognition architecture
- ShareG...
SUMMARY: The biggest enterprise AI question is which organization can most effectively operationalize, govern, and economically scale AI agents across the business.
SHOW: 1032
SHOW TRANSCRIPT: The Enterprise AI Show #1032 Transcript
SHOW VIDEO: https://youtu.be/GsK_RUnYroI
SHOW SPONSORS:
- ShareGate - ShareGate Protect. Microsoft 365 Governance. We got this.
- Nasuni - Activate your data for AI and request a demo
SHOW NOTES:
Opening T...
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!
S...
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 yo...
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 d...
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: ...
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:...
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:
- ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!
- Nasuni - Activate your data for ...
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:
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 yo...
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 - Ac...
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 Prot...
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
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