The Enterprise AI Show

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

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SHOW LINKS

The New Kingmakers
Agents: The new, New Kingmakers
Tecosystems Blog
RedMonk
LinkedIn

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. 

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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.

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SHOW: 1068
SHOW TRANSCRIPT: The Enterprise AI Show #1068 Transcript
SHOW VIDEO: https://youtu.be/kaNik7LxV3s
SHOW LINKS:
https://theenterpriseaishow.com/

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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?
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SHOW LINKS
Strengths:
Brand awareness of Claude with software developers
Use-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 doom
Uncertainty about alignment to US government after 2026
Increasing annual losses against revenue
Security and safety concerns (Mythos)
Future commitments and long-term financials?

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Bluesky: @TheEntAIShow.bsky.social
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FEEDBACK?
Email: show @ the enterprise ai show dot com
Bluesky: @TheEntAIShow.bsky.social
Twitter/X: @TheEntAIShow
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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:
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Nasuni - Activate your data for AI and request a demo

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

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
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SHOW LINKS
Datasaur homepage
Ivan Lee on LinkedIn
Datasaur Launches Forge: AI Native Services to Deploy Private, Model-Agnostic AI Inside Regulated Enterprises
Datasaur'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.

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