Podcast
The Enterprise AI Show
Hosted by Massive Studios · EN
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
55episodes
Episodes
Newest firstAll episodes
Are companies giving away their secrets to AI?
2w ago00:28:40Tap to summarizeSUMMARY: Are CEO's frustrated with the lack of control, costs and sovereignty of their AI environments? SHOW: 1042SHOW TRANSCRIPT: The Enterprise AI Show #1042 TranscriptSHOW VIDEO: https://youtu.be/xgQv8WP-DNISHOW SPONSORS:ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!Nasuni - Activate your data for AI and request a demoSHOW NOTES:Palantir and NVIDIA partnership (June 2026) - first 11 minutesPalantir CEO (Alex Karp) on CNBC“The VPC Privacy Illusion - Why Private LLMs still expose your data”The biggest mistake organizations make isn’t choosing the right model, it’s focusing on models at all (via LinkedIn)There’s a level of unhappiness and distrust of the frontier labs from CEOsThere needs to be an application layer on top of LLMs (e.g. “harness”, Palantir Ontology)This application layer prevents the LLMs from learning your business from your data“Alpha” is business differentiation (ability to outperform the market)He questions why the frontier model labs are charging by tokens and not outcomes (questions the entire AI business model)He questions “the true cost” of AI outputs He claims that CEOs are now concerned about frontier labs entering the business of the customers - brings up an interesting misunderstanding of how interacting with LLMs works (“we’re safe, it’s deployed in our VPC”)FEEDBACK?Email: show @ the enterprise ai show dot comeBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow
Transcribe →AI News of the Month - June 2026
3w ago00:31:27Tap to summarizeSUMMARY: Brian Gracely (@bgracely) and Aron Delp (@aarondelp) discuss the biggest AI news stories from the month of June, 2026. SHOW: 1041SHOW TRANSCRIPT: The Enterprise AI Show #1041 TranscriptSHOW VIDEO: https://youtu.be/SXmPOgE5jGkSHOW SPONSORS:Nasuni - Activate your data for AI and request a demoShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!SHOW NOTES:Links to all the AI News covered in this month’s showFEEDBACK?Email: show @ the enterprise ai show dot comeBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow
Transcribe →Enterprises are concerned about AI Costs, Governance and Trust
3w ago00:28:41Tap to summarizeSUMMARY: 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: 1040SHOW TRANSCRIPT: The Enterprise AI Show #1040 TranscriptSHOW VIDEO: https://youtu.be/RyB4m17YK_4SHOW SPONSORS:Nasuni - Activate your data for AI and request a demoOutShift by Cisco - “Scaling Out Superintelligence” The Internet of Cognition architectureShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!SHOW NOTES:THESIS: After spending time with a number of Enterprise companies, what are a list of challenges and concerns they still have in implementing GenAI across a broad set of use-cases within the Financial Services industry?Everybody started with what was available (e.g. CoPilot)Enterprise implementations (now) aren’t autonomousRising costs are the looming concernGovernance is a rising concernMeasurements of improvement are available, but variedExplaining measurements is complicatedExplaining trust is more complicatedUse-cases are fragmented, but there if you apply the technology, but not always obviousDe-centralized (shadow AI) to Centralized to De-centralized (semi-controlled) The learning curves are very asymmetrical across teamsNot everyone has access to Mythos or GPT-5.5-Cyber (yet)FEEDBACK?Email: show @ the enterprise ai show dot comeBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow
Transcribe →A Day in the Life of a Forward-Deployed Engineer
4w ago00:34:20Tap to summarizeSUMMARY: 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: 1039SHOW TRANSCRIPT: The Enterprise AI Show #1039 TranscriptSHOW VIDEO: https://youtu.be/QY0fqu2O84MSHOW SPONSORS:OutShift by Cisco - “Scaling Out Superintelligence” The Internet of Cognition architectureShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!Nasuni - Activate your data for AI and request a demoSHOW NOTES:Mozilla Thunderbolt launched Mozilla Thunderbolt (homepage)Topic 1 - Welcome to the show, tell us a bit about your background and what you focus on these days.Topic 2 - Let’s talk about the role of Forward Deployed Engineer, it’s being talked about a lot, but you’re living in that world now. What problems are FDEs usually tasked with trying to solve, or new things to implement?Topic 3 - We’ve seen other roles (DevOps, PlatformEng, etc.) that evolved from other roles or skills. What type of background lends itself to success in FDE? What skills are needed going forward?Topic 4 - You’re also working on some AI harness implementations. What can you tell us about those challenges and the technologies behind the harness?Topic 5 - At what point does an AI harness make sense for a company? What types of AI challenges typically require those next steps? Topic 6 - Working in the middle of this evolving AI space, what are some perspectives you’ve gained over the last 6-12 months? What do you wish you knew ahead of time? FEEDBACK?Email: show @ the enterprise ai show dot comeBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow
Transcribe →Chaotic AI Markets: Focus on what you can control
4w ago00:23:07Tap to summarizeSUMMARY: 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: 1038SHOW TRANSCRIPT: The Enterprise AI Show #1038 TranscriptSHOW VIDEO: https://youtu.be/T2ZIYLpl_cESHOW SPONSORS:ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!Nasuni - Activate your data for AI and request a demoOutShift by Cisco - “Scaling Out Superintelligence” The Internet of Cognition architectureSHOW NOTES:Leaked documents show OpenAI is losing billionsAnthropic’s Fable and Mythos models banned from non-US foreign nationalsThe AI layoff wave is becoming a powder kegProfessors says AI-related job losses are inevitableTHESIS: On this Father’s Day, with an AI market that often times doesn’t make any sense, I thought about the type of advice that my father gave me over the years and how it would apply to this time of significant change. Show up, keep up and shut upMake yourself invaluableFocus on what you can controlBe an expert in somethingWhen in doubt, get closer to people and how money is madeWhen things don’t make sense, focus on fundamentalsMarkets can be irrational way longer than you can be solventTry and think a couple steps aheadFEEDBACK?Email: show @ the enterprise ai show dot comeBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow
Transcribe →AI Cyber is expanding a Vulnerability Gap
Jun 1700:26:03Tap to summarizeSUMMARY: 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: 1037SHOW TRANSCRIPT: The Enterprise AI Show #1037 TranscriptSHOW VIDEO: https://youtu.be/H5KxoiEIfUoSHOW SPONSORS:Nasuni - Activate your data for AI and request a demoOutShift by Cisco - “Scaling Out Superintelligence” The Internet of Cognition architectureShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!SHOW NOTES:Project Lightwell (Red Hat and IBM)Athena (Chainguard)Anthropic Project GlasswingOpenAI GPT 5.5-CyberTHESIS: Major initiatives are forming to help enterprise organizations combat security vulnerability threats found or created using new AI-cyber tools such as Anthropic Mythos. What are the key considerations, and what additional steps do organizations need to take to be advantaged by these capabilities? Part 1The Breaking Point and the Mythos MomentThe scope of open source security and supportPatches, disclosures and upstream open sourceClearinghouses, EOs, Laws and CommunitiesRemediation - Build vs. BuyPart 2How fast can you get from Patch to Production?Mitigation before patchingFast path and stable patch pipelines?Automation in patching vs. automation in deploymentFEEDBACK?Email: show @ the enterprise ai show dot comeBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow
Transcribe →Do CIOs need to create an Enterprise AI Harness?
Jun 1200:22:52Tap to summarizeSUMMARY: 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: 1036SHOW TRANSCRIPT: The Enterprise AI Show #1036 TranscriptSHOW VIDEO: https://youtu.be/ZgkMF7G3YfoSHOW SPONSORS:OutShift by Cisco - “Scaling Out Superintelligence” The Internet of Cognition architectureShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!Nasuni - Activate your data for AI and request a demoSHOW NOTES:Andy Weir (The Martian) on Eps. 193Systems of Record Won the SaaS Era - Clearinghouses Will Win the Agents EraHarness Engineering is where Enterprise AI becomes realTHESIS: It comes up as different control points, but CIOs are ultimately trying to figure out how to get the value from Enterprise AI while delivering a set of consistency across different teams and use-cases. Let’s explore what this “Enterprise Harness” is starting to look like. Enterprise Clearinghouse Enterprise Intelligence (a.k.a. Middleware)Enterprise Catalog - Models as a Service, Agents as a ServiceEnterprise Skills or Shareable Prompt HarnessesSymantec Routing to ModelsAI Gateway ControlsFEEDBACK?Email: show @ the enterprise ai show dot comeBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow
Transcribe →Should CIOs have a backup plan for AI?
Jun 1000:48:31Tap to summarizeSUMMARY: 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: 1035SHOW TRANSCRIPT: The Enterprise AI Show #1035 TranscriptSHOW VIDEO: https://youtu.be/ngBBpP2LgdoSHOW SPONSORS:ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!Nasuni - Activate your data for AI and request a demoOutShift by Cisco - “Scaling Out Superintelligence” The Internet of Cognition architectureSHOW NOTES:THESIS: Between pending IPOs (Wall St. demands), high user-demand, GPU/TPU shortages, Data Center shortages, Model prices increasing (open models fading away), the cost of using AI is going to get more expensive over time. Should CIOs start thinking about a Backup plan to their current AI adoption that has lower cost alternatives?Topic 1 - Assuming you could get access to GPUs/TPUs/Accelerators, and suitable data center space to host them, what would be your thinking as a CIO if you felt like you needed to own some aspect of your AI roadmap/journey? Topic 2 - Assuming the normal “Shadow AI” backlash that you’d receive for offering something that wasn’t “frontier” level, how would you go about trying to communicate that within your organization?Topic 3 - What metrics or KPIs would you initially target to try and get buy-in that your approach was acceptable and moving towards the company goals?FEEDBACK?Email: show @ the enterprise ai show dot comeBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow
Transcribe →What are the incentives to share AI learning curves with teammates?
Jun 500:21:20Tap to summarizeSUMMARY: 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: 1034SHOW TRANSCRIPT: The Enterprise AI Show #1034 TranscriptSHOW VIDEO: https://youtu.be/TvIFwNN-6ckSHOW SPONSORS:Nasuni - Activate your data for AI and request a demoOutShift - “Scaling Out Superintelligence” The Internet of Cognition architectureShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!SHOW NOTES:Why AI Economics are changingHow will team collaboration evolve with Enterprise AI?Topic 1 - How do we measure AI-adoption success? Number of workloads?Financial metrics (Spend, ROI, Costs-Saved, etc.)?Speed improvements?People-level?Topic 2 Right now the AI tools are very individual-centric The machinery to share, even at the basic enterprise-level, is very difficultThe experience to share is non-deterministic, just as everyone’s working style is different.Topic 3 - The motivation to share is still unknown. How do you encourage collaboration when so many companies are laying off people, or the specter of that happening is growing?What was the motivation before (team goals?) and how does that change now? People don’t want to be monitored, so how does a manager have visibility?What happens when companies remove the managers (“the counters”)? FEEDBACK?Email: show @ the enterprise ai show dot comeBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow
Transcribe →Cerebras is disrupting the market with Fast Inference
Jun 300:35:21Tap to summarizeSUMMARY: 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 AISHOW: 1033SHOW TRANSCRIPT: The Enterprise AI Show #1033 TranscriptSHOW VIDEO: https://youtu.be/ed2nVbOtZiASHOW SPONSORS:OutShift - “Scaling Out Superintelligence” The Internet of Cognition architectureShareGate - ShareGate Protect. Microsoft 365 Governance, we got this!Nasuni - Activate your data for AI and request a demoSHOW NOTES:OpenAI announces 750MW partnership with CerebrasCerebras and AWS partnershipCerebras announces IPOTopic 1 - Welcome to the show. Tell us about your background, and what you focus on today. Topic 2 - For anyone that’s not familiar with Cerebras, give us an overview of the company, and especially an overview on the Cerebras technologies (e.g. Wafer-Scale Engine).Topic 3 - Cerebras’ WSE architecture is different from many of the GPU or GPU-like architectures in the market today. Centralized vs. distributed architectures always have their tradeoffs. Walk us through the technical and economic value of the Cerebras architecture.Topic 4 - Congratulations on the recent IPO (raised $5.55B). Let’s use that as a point in time vs the previous planned IPO. How has the market changed in that timeframe, and how has the Cerebras position changed? Topic 5 - Cerebras (today) offer both WSE hardware, and Cerebras Cloud (API) - very different GTM paths. Can we expect both of those to stay top priorities, or have the market dynamics shifted such that the priorities shift more towards the WSE business - as we’re seeing OpenAI, AWS and other engagements announced?Topic 6 - Is Cerebras a training and inference company, or are the economics of inference significantly different enough that it needs to be the sole focus of the company (for now)? Topic 7 - How much effort is it for any company to add support for the Cerebras chips if they have previously been using other architectures?Topic 8 - An IPO is a major milestone for any company, but the markets will now look for your future story. How do you see the AI market evolving over the next 2-5 years, and what are some things that people aren’t understanding yet about how it will evolve?FEEDBACK?Email: show @ the enterprise ai show dot comeBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow
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