The Enterprise AI Show

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:
Links to all the AI News covered in this month’s show
FEEDBACK?
Email: show @ the enterprise ai show dot come
Bluesky: @TheEntAIShow.bsky.social
Twitter/X: @TheEntAIShow
Instagram: @TheEntAIShow

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 data for AI and request a demo
SHOW NOTES:
Opening Thesis - Was the first wave of AI adoption artificially cheap? - The industry may be transitioning from subsidized growth to usage-based economics. 
Key Topics 
1. Evidence AI Was Subsidized 
Massive CAPEX vs low end-user pricing 
Generous enterprise bundles 
Frontier model access for $20/month 
2. The Hidden Economics of AI Agents - 
Agents consume exponentially more inference 
Tool orchestration, retries, memory, verification 
3. Why Frontier Labs Are Shifting Focus 
From benchmark supremacy to orchestration 
Governance, memory, connectors, MCP, workflows 
4. Forecasting AI Pricing 
12 Months:  Commodity inference gets cheaper - 
Frontier reasoning remains premium 

24 Months:  AI billing resembles AWS-style infrastructure billing 
Runtime, memory, latency and orchestration become billable 

36 Months: Outcome-based pricing emerges 
AI spending shifts from IT budgets to labor budgets Final Takeaways  
Commodity AI becomes utility-priced 
Frontier reasoning becomes premium 
Agents reshape enterprise economics

Key Conclusions
1. AI probably was subsidized
The economics strongly suggest adoption-first pricing.
2. The subsidy era may be ending
Premium tiers and metered pricing are emerging.
3. AI agents fundamentally alter economics
Usage scales exponentially with autonomy.
4. Commodity AI and frontier reasoning are separating
One becomes cheap.
One becomes premium.
5. The real battle is moving upward in the stack
The future moat may be:
orchestration
governance
workflows
enterprise context
operational tooling

Final Closing Thought
“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?’”
FEEDBACK?
Email: show @ the enterprise ai show dot come
Bluesky: @TheEntAIShow.bsky.social
Twitter/X: @TheEntAIShow
Instagram: @TheEntAIShow

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 and request a demo
ShareGate - ShareGate Protect. Microsoft 365 Governance. We got this.
SHOW NOTES:

Topic 1 - Welcome to the show. Tell us about your background, and what led you to create Sema4.ai?. 
Topic 2 - AI Agents vs. Automation 2.0. What Actually Changed. Tell us about the Sema4.ai platform and capabilities. What challenges does it solve today?
Topic 3 - You’re initially focused on solving challenges for the CFO, which means there is a ROI-focus all the time. Why did you target that segment of the business first?
Topic 3a - What are the biggest hidden costs in enterprise AI deployments today?
Topic 4 - Sema4.ai emphasizes “your LLM, your VPC, your data.”  What are the biggest considerations for companies looking to create these private/sovereign AI solutions? What typically gets overlooked?
Topic 5 - How do you tend to frame the conversation about AI trustworthiness, and the role of humans vs. agents for enterprise work? 
Topic 6 - It feels like so much has changed or evolved with AI in the last 2-3 years. How does an Enterprise think about this much change for something that will be core to many critical applications? What will the Enterprise Architecture look like in 2 years?
Topic 7 - Sema4.ai emerged partly from the acquisition of Robocorp and has roots in open-source automation.  Do you have a perspective on the role open-source will play in AI going forward? 

FEEDBACK?
Email: show @ the enterprise ai show dot come
Bluesky: @TheEntAIShow.bsky.social
Twitter/X: @TheEntAIShow
Instagram: @TheEntAIShow

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/sgqg7uqErA0
SHOW SPONSORS:
ShareGate - ShareGate Protect. Microsoft 365 Governance. We got this.
Nasuni - Activate your data for AI and request a demo
SHOW NOTES:
Nearly 1 in 3 Organizations Report AI-Driven Data Exposure Incidents
Other Resources:A complete checklist for Microsoft 365 governance https://sharegate.com/guides/checklist-for-microsoft-365-governance 
Request a demo of ShareGate: Get a 1:1 ShareGate demo tailored to your Microsoft 365 use case 
Article around that divide of confidence vs reality of data exposure sharegate.com/blog/93-of-it-leaders-are-confident-in-their-ai-governance-but-nearly-1-in-3-report-data-exposure-incidents 
The State of Microsoft 365 industry report with more stats and insights - State of Microsoft 365 2025 | Free survey report – ShareGate | Sharegate (new one coming SOON)

Topic 1 - Welcome to the show. Tell us about your background, and what you focus on today. Tell us about Sharegate. 
Topic 2 - How has generative AI changed the definition of “governance” inside Microsoft 365 environments?
Topic 3 - What are organizations underestimating about AI readiness in M365?
Topic 4 - What do you think about “oversharing risk” in the era of AI assistants?
Topic 5 - What patterns are you seeing around shadow AI and unsanctioned SaaS usage?
Topic 6 - How should organizations rethink identity and access management for AI-driven workflows?
Topic 7 - What does good AI governance look like operationally—not just as a policy document?
FEEDBACK?
Email: show @ the enterprise ai show dot come
Bluesky: @TheEntAIShow.bsky.social
Twitter/X: @TheEntAIShow
Instagram: @TheEntAIShow

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:
Reviewing the Major AI Vendors 
FEEDBACK?
Email: show @ the enterprise ai show dot come
Bluesky: @TheEntAIShow.bsky.social
Twitter/X: @TheEntAIShow
Instagram: @TheEntAIShow