The Enterprise AI Show

Massive Studios
  • 4.6 (151)
  • Technology
  • Updated Daily

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 

  1. 1h ago

    The New, New Kingmakers: Agents, Developers, and the Future of Software with Stephen O'Grady

    Brandon interviews Stephen O'Grady, principal analyst and co-founder of RedMonk, about his 2013 book *The New Kingmakers* and his recent follow-up, "Agents: The new, New Kingmakers." O'Grady explains that the original thesis was simple: developers had gone from an afterthought in technology purchasing to the group whose choices determined what got used, driven first by open source (the LAMP stack, Linux) and then by cloud services like S3 and EC2 that removed the need to ask for budget. The two discuss why Sun was disrupted from every direction while Oracle and Cisco endured, with O'Grady noting that databases are the stickiest, highest-risk asset in the stack. He recounts getting an early look at GitHub Copilot a year before ChatGPT, but says the late-2025 jump in model capability was a step change he did not foresee. On software development, O'Grady expects a spectrum rather than a consensus on reviewing AI-written code: toy apps and disposable software may never be read by a human, while medical imaging, aviation, and defense will demand real oversight. He uses his construction background to describe the developer's shift from builder to architect, and warns that the "human in the loop" role is the weak end of the outcomes. Brandon and O'Grady examine why individual developers feel superhuman while organizations don't see the gains, with O'Grady pointing to downstream bottlenecks like the flood of PRs overwhelming open source maintainers. He cites Dr. James Bessen's bank teller research as a reminder that automation's effect on employment is hard to predict, and asks what happens if there is an order of magnitude more software in the world. On vendors, O'Grady expects both human-facing and agent-only businesses to coexist, with the biggest growth in agents because they scale like cloud, while Brandon points to Cloudflare's rewrite of Wrangler as a model for exposing complete APIs. O'Grady cautions that giving agents the keys to the kingdom is harder than it sounds, since subtle violations (like pulling copyrighted headshots from MLB.com) are harder to foresee than deleting a database. They close with hot takes: O'Grady takes the under on a 10% chance of AI wiping out humanity, arguing the industry doesn't draw a bright enough line between digital and physical capability, and he remains skeptical of frontier model valuations and the circular investments behind them, especially as open-weight models close the gap. SHOW: 1069 SHOW TRANSCRIPT: The Enterprise AI Show #1069 Transcript SHOW VIDEO: https://youtu.be/E6UFnW40BHQ SHOW SPONSORS: NordLayer - Use ENTERPRISE10 for 10% offPalo Alto - Secure every identity with Idira by Palo Alto Networks  SHOW LINKS The New KingmakersAgents: The new, New KingmakersTecosystems BlogRedMonkLinkedIn GUEST BIO Stephen O'Grady is the principal analyst and co-founder of RedMonk, a developer- and practitioner-focused industry analyst firm. He is the author of *The New Kingmakers* (2013), which argued that developers had become the most important decision-makers in technology, and writes the Tecosystems blog.  FEEDBACK? Email: show @ the enterprise ai show dot comBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow

  2. 3d ago

    AI News for End of September 2026

    Brian(@bgracely) and Brandon(@bwhichard) discuss the biggest AI news stories from the second half of September 2026. Oracle sent a force majeure notice on a major data center build, which Brandon reads as an early signal worth tracking. If other companies follow, it would point to stress in AI infrastructure commitments, and if not, it is a one-off. Brian suggests the industry needs a "Jenga chart" of whose money is propping up whose, with the contractors who actually pour concrete at the base. On the wave of agent launches (Meta's Muse, OpenAI's dots, and OpenClaw Enterprise), they agree that giving everyone a cloud-hosted computer for their agent is a real step toward mainstream adoption. Brian says the unanswered questions are accountability when an agent errs, security controls that don't require dozens of settings, and how people decide what is important enough to keep for themselves. Brandon argues agents should step in at the moment of a task, like filling out a form, rather than needing constant delegation. They also note the move toward soft, cuddly agent branding and the lack of easy ways to share skills across people and teams. The show closes with Meta's hiring of MongoDB's CEO to lead its enterprise push, which Brandon expects to fail because consumer companies start at a deficit in enterprise. SHOW SPONSORS: Palo Alto - Secure every identity with Idira by Palo Alto Networks NordLayer - Use ENTERPRISE10 for 10% off SHOW: 1068 SHOW TRANSCRIPT: The Enterprise AI Show #1068 Transcript SHOW VIDEO: https://youtu.be/kaNik7LxV3s SHOW LINKS: https://theenterpriseaishow.com/ FEEDBACK? Email: show @ the enterprise ai show dot comBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow

  3. Sep 30

    The Anthropic IPO?

    We review the potential Anthropic IPO, in the context of revenue trajectory, expense trajectory and planned commitments, past and future funding rounds, future expanse commitments to large datacenter projects, and the strengths and weaknesses of the business in the current and potentially future political climates in the US and around the world.  SHOW: 1067 SHOW TRANSCRIPT: The EntAIShow #1067 - The Anthropic IPO? SHOW SPONSORS Nasuni - Activate your data for AI and request a demoNordLayer - Use ENTERPRISE10 for 10% off.SHOW LINKS Strengths: Brand awareness of Claude with software developersUse-Case adoption for Enterprise workers (white-collar, software, research, etc.)Depth and experience of Anthropic Frontier Labs (Model Building, Research, etc.)Weaknesses CEO who frequently scares the world with his proclamations about doomUncertainty about alignment to US government after 2026Increasing annual losses against revenueSecurity and safety concerns (Mythos)Future commitments and long-term financials? FEEDBACK? Email: show @ the enterprise ai show dot comBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShowFEEDBACK? Email: show @ the enterprise ai show dot comBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow

  4. Sep 27

    The OpenAI IPO?

    We review the potential OpenAI IPO, in the context of revenue trajectory, expense trajectory and planned commitments, past and future funding rounds, future expanse commitments to large datacenter projects, and the strengths and weaknesses of the business in the current and potentially future political climates in the US and around the world.  SHOW: 1066  SHOW TRANSCRIPT: The Enterprise AI Show #1066 SHOW VIDEO: https://youtu.be/PkLSI2pRZs8 SHOW SPONSORS: NordLayer - Use ENTERPRISE10 for 10% off.Nasuni - Activate your data for AI and request a demo FEEDBACK? Email: show @ the enterprise ai show dot comBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShowFEEDBACK? Email: show @ the enterprise ai show dot comBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow

  5. Sep 23

    How Do Regulated Enterprises Deploy Private, Secure AI?

    Aaron interviews Ivan Lee, founder and CEO of Datasaur, about what it takes to build private, secure AI for regulated enterprises. Lee traces the shift away from third-party model reliance to compliance pressure, IP protection, and cost, and frames the core decision as buy versus rent: enterprises historically rented frontier models by default, but Western and Chinese open-weight models have matured enough that companies like AT&T now run a growing share of workloads on owned infrastructure. He breaks the stack into three layers (infrastructure, model, and harness), argues models have become commoditized enough to be swapped like building materials, and calls the harness, the connective layer to internal data and tools, the least solved but highest-leverage piece. Lee describes agentic AI's shift from opt-in tools to opt-out, event-triggered workflows as the real 2025-2026 adoption unlock, while flagging FinOps trade-offs (agentic tasks can run 3 million tokens versus 2,000 for a chatbot query) and the custom benchmarking his team uses to earn CISO trust before production rollout. SHOW: 1065  SHOW TRANSCRIPT: The Enterprise AI Show #1065 SHOW VIDEO: https://youtu.be/PkLSI2pRZs8 SHOW SPONSORS NordLayer - Use ENTERPRISE10 for 10% off.Nasuni - Activate your data for AI and request a demo SHOW LINKS Datasaur homepageIvan Lee on LinkedInDatasaur Launches Forge: AI Native Services to Deploy Private, Model-Agnostic AI Inside Regulated EnterprisesDatasaur's Private LLM overview GUEST BIO Ivan Lee is the founder and CEO of Datasaur, which builds private, model-agnostic AI agents that deploy entirely inside a regulated enterprise's own infrastructure. He previously built AI products at Yahoo and Apple after Yahoo acquired his first company, Loki Studios, and holds a computer science degree from Stanford. Datasaur's clients include a leading GSIB, federal agencies, and Am Law 100 firms, and its backers include Initialized Capital and OpenAI president Greg Brockman. FEEDBACK? Email: show @ the enterprise ai show dot comBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow

  6. Sep 21

    AI News for Mid-September 2026

    Aaron and Brandon cover what the week's news means for enterprise buyers. They question whether Oracle's reported $664 billion backlog is durable demand or overlapping commitments, and Brandon argues contracted future spend is how enterprise business works. On the labs' "slow down" messaging, Brandon sees no coordination, only incentives, while Aaron finds the timing too coincidental. Salesforce's Nemotron-based model points to enterprises customizing open models instead of building their own, and Brandon doubts labs will displace systems of record like Workday or SAP. Aaron argues agent pricing has reverted to familiar free, bundled, and negotiated tiers. He sees agent swarms as research capability that most enterprises lack the trust and human-in-the-loop controls to run. SHOW SPONSORS: Nasuni - Activate your data for AI and request a demoNordLayer - Use ENTERPRISE10 for 10% off. SHOW: 1064 SHOW TRANSCRIPT: The Enterprise AI Show #1064 Transcript SHOW VIDEO: https://youtu.be/hrfTovN3kMw SHOW LINKS: https://theenterpriseaishow.com/FEEDBACK? Email: show @ the enterprise ai show dot comBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow

  7. Sep 16

    Building AI Agents That Support Enterprise Teams

    Aaron interviews Diego Oppenheimer, general partner at the AIT Fund (the venture fund behind the AI Tinkerers builder community), about what it takes to move AI agents from personal experimentation into enterprise-grade deployment. Drawing on his own agent fleet (a chief-of-staff agent, a content strategist, and Ashley, an always-on AI community manager serving AI Tinkerers' 127,000+ members) as a proving ground, Oppenheimer lays out an enterprise security model built on treating agents as digital employees with their own delegated identities and credentials, scoped access rather than blanket access to accounts like email and calendar, and continuous audit logging (via the open-source tool Hyperware) in place of trust based on prior behavior. He argues enterprises get burned by chasing a single omnipresent agent instead of narrowing agents to specialized, restricted workflows, the same specialization principle that has driven results throughout machine learning, and flags scheduling as a deceptively hard example where the "10% edge cases" eat most of the effort. He also describes deliberately red-teaming his own agents for weeks (trying to break out of containers, extract credentials, and social-engineer them) before granting them any real access, and points to NanoClaw's containerized, minimal-component design as a model worth enterprise attention. The conversation closes on identity, responsibility, and permissioning as the unresolved internals enterprises must solve before scaling agent autonomy, and on Oppenheimer's prediction that many enterprise roles will shift toward "exception handling" as teams of AI coworkers absorb routine work and escalate only what needs human judgment. SHOW: 1063  SHOW TRANSCRIPT: The Enterprise AI Show #1063 Transcript SHOW VIDEO: https://youtu.be/vL8btTMcInE SHOW SPONSORS NordLayer - Use ENTERPRISE10 for 10% offNasuni - Activate your data for AI and request a demo SHOW LINKS Diego Oppenheimer homepageDiego on LinkedInAI TinkerersGuardrails AINanoClaw on GitHubThe New Stack, "OpenClaw vs. Hermes Agent: The race to build AI assistants that never forget"The New Stack, "NanoClaw and Docker team up to isolate AI agents inside MicroVM sandboxes" GUEST BIO Diego Oppenheimer is working full-time at AIT Fund (the fund behind AI Tinkerers) and previously was a partner at Factory and served as CEO-in-residence at Factory. He founded Algorithmia, an enterprise MLOps platform acquired by DataRobot, co-founded Guardrails AI, and earlier in his career led teams at Microsoft shipping Excel, SQL Server, and Power BI. He is currently running AI agents inside his own team to take on real, sustained work, including one named Ashley, and documenting what he's learned in a new video series with Joe Heitzeberg. FEEDBACK? Email: show @ the enterprise ai show dot comBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow

  8. Sep 13

    Securing AI Agents in the Enterprise: NanoClaw, Zero Trust Guardrails, and Governance at Scale

    Brian and Aaron interview Gavriel Cohen, co-founder and CEO of Nanoco and creator of the open-source agent framework NanoClaw, about securing AI agents in enterprise environments. Cohen shares how he built NanoClaw after discovering major security and safety gaps while using agents for an AI native marketing agency, and how the project grew to over 30,000 GitHub stars and over half a million downloads. They discuss why Fortune 500s, financial institutions, universities, and government groups feel urgent pressure to adopt agents but are blocked by control, privacy, and security concerns. Cohen outlines a zero-trust approach using microVM isolation, no credentials inside agent environments, a policy-enforcing gateway with granular controls, audit logs, cost attribution, and human-in-the-loop approvals at key decision points. SHOW: 1062 SHOW TRANSCRIPT: The Enterprise AI Show #1062 Transcript SHOW VIDEO: https://youtu.be/h906EEQSRs8 SHOW LINKS: NanoClaw on GitHubNanoCo homepageTechCrunch: The wild six weeks for NanoClaw's creator that led to a deal with DockerThe New Stack: Gavriel Cohen found his own code inside OpenClaw, so he walked awayOpenAI: The Hugging Face incident and the road ahead SHOW SPONSORS: Nasuni - Activate your data for AI and request a demoNordLayer - Use ENTERPRISE10 for 10% off GUEST BIO: Gavriel Cohen is co-founder and CEO of NanoCo, and creator of NanoClaw, the open-source agent harness he built as a small, auditable, secure alternative to OpenClaw. He spent a decade as a developer and team lead at Wix before building NanoClaw in a weekend, a project that has since drawn a Docker integration and an outside security review. He holds a BSc in Physics and Computer Science from Tel Aviv University. FEEDBACK? Email: show @ the enterprise ai show dot comBluesky: @TheEntAIShow.bsky.socialTwitter/X: @TheEntAIShowInstagram: @TheEntAIShow

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About

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 

Information

  • Creator
    Massive Studios
  • Years Active
    2011 - 2026
  • Episodes
    1.1K
  • Rating
    Explicit
  • Copyright
    © 2026 Massive Studios
  • Show Website
    The Enterprise AI Show

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