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
Brian interviews Derek Carr and Mrunal Patel, distinguished engineers at Red Hat, about OpenClaw Enterprise, the new open-source project that brings Red Hat, NVIDIA, and the OpenClaw community together to make persistent AI agents safe and manageable at enterprise scale. The work started with OpenShell, a deny-by-default sandbox the pair helped build with NVIDIA that treats every agent as potential malware. Agents never see credent...
Brian and Brandon take a detour from the usual tech news to ask a question every enterprise buyer of AI should be asking: why do some of tech’s most celebrated leaders project absolute confidence in claims that later prove false? Starting from the new Elizabeth Holmes documentary, they debate whether that kind of conviction is innate or learned. Brian argues it develops in stages, as each funding round and glowing press profi...
Brandon interviews Dan Manges, co-founder and CEO of RWX, about why continuous integration is the bottleneck for engineering teams working with coding agents. Manges, previously CTO at Braintree and Root, explains that he started RWX after watching CI tooling fail to scale with fast-growing codebases in regulated industries. He argues that feedback loops under five to ten minutes keep engineers in a flow state, and that slower loop...
Brian and Brandon open mid-October’s AI news of the month by asking whether a yes-or-no answer engine like Jev could have saved the Commanders from a clock-management meltdown, and why a binary classifier is worth a reported $7.5 billion. A six-month check-in on their May AI draft leaves the scorecard roughly even, with Anthropic the clear winner over Google. Then come the financial cracks. CoreWeave’s borrowing costs h...
Brandon interviews Dominic Williams, founder, president, and chief scientist of the DFINITY Foundation, about the Internet Computer and why he set out to build a new back-end compute stack. Williams traces his path from building the kids' MMO Fight My Monster, one of the first serious production users of Cassandra, to decentralized networks and the founding of DFINITY in 2016. He explains the thesis behind the Internet Computer: a ...
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 ...
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 wh...
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
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://yout...
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&am...
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 ent...
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 o...
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...
Aaron interviews David Aronchick, CEO @ Expanso (former PM lead for Kubernetes, Kubeflow co-founder, and open-source ML leader at Azure) about how open source is reshaping the AI infrastructure stack. Aronchick recounts his path from early Linux and enterprise work to launching Kubernetes and GKE, then creating Kubeflow in 2017 to orchestrate end-to-end ML workflows on Kubernetes. The discussion centers on gaps in AI infrastructure...
Brian, Brandon, and Aaron discuss enterprise AI adoption using the sales analogy of whether AI is a “vitamin” or a “painkiller,” arguing that successful transformation still requires a burning-platform event. Brandon suggests AI adoption resembles past digital transformations: without urgent pressure (e.g., a data center closing), organizations resist change and justify existing processes. Brian describes a ...
Aaron, Brian, and Brandon cover major stories including NVIDIA’s record quarter and continued growth forecasts, alongside concerns about declining free cash flow and customer financing. They discuss NVIDIA’s reported $12.9B acquisition of Hugging Face as a strategic move to strengthen the open-model ecosystem and go up the stack, and Stripe’s $8B acquisition of OpenRouter as routing infrastructure for model choice...
SUMMARY: Brian, Brandon, and Aaron focus on AI watermarking, driven largely by EU transparency requirements, and discuss how approaches like token-selection patterns can be detected but were reportedly cracked quickly with tools that strip watermarks. Brandon and Brian debate whether watermarking is useful long-term, suggesting most people care more about whether content is helpful than whether AI was involved, and questioning the ...
SUMMARY: Brandon speaks with Rich Ziade, co-founder and CEO of Aboard, about why enterprise AI projects fail without real discovery, why "agents" have been oversold as a headcount play, and why organizational urgency, not new tooling, is what actually makes digital transformation succeed.
SHOW: 1057
SHOW TRANSCRIPT: The Enterprise AI Show #1057 Transcript
SHOW VIDEO: https://youtu.be/RMgycbmuXGs
SHOW SPONSORS:
- Nasuni - Activate your...
SUMMARY: Brian, Brandon, and Aaron discuss news about Nvidia’s reported $105B backing of OpenAI’s Ohio data center and what it implies for GPUs as an “asset class” and enterprise AI. Brian argues Jensen Huang is shifting Nvidia’s narrative from needing the newest chips immediately to portraying GPUs as long-lived, cash-flowing assets that can be financed like bonds, pushing risk onto banks and private ...
SUMMARY: Brandon and Aaron discuss the pros and cons of owning or renting your model weights. What does that mean for the Enterprise, and what should you be considering?
SHOW: 1055
SHOW TRANSCRIPT: The Enterprise AI Show #1055 Transcript
SHOW VIDEO: https://youtu.be/uc0GZBLgUeo
SHOW SPONSORS:
Topic: Own Your Weights or Rent Them?
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