The Enterprise AI Show

AI’s Netflix Moment: What Early Cloud Teaches Us About the Next Phase

Brian and Brandon discuss what happens to enterprise AI if the market corrects and the era of "move fast and break things" gives way to hard questions about ROI. Brandon

Claude, Make Me Rich: Finding Anthropic’s Next Giant Market

Brian and Brandon debate how a newly hired product leader at Anthropic would find growth big enough to match the expectations of an IPO, which Brian expects around the en

From $2 Trillion to $20 Trillion: What Anthropic Has to Become Beyond Claude

Brian and Brandon debate what Anthropic has to become if its IPO succeeds and, in Brian’s hypothetical, it must grow from a $2 trillion company into a $20 trillion one. B

AI & Cloud News - End of October 2026

Brian and Brandon follow the money through a big month in AI, starting with Cisco president Jeetu Patel handing a 27-year-old ex-founder from acquired startup EzDubs unli

OpenClaw Enterprise: Making AI Agents Safe for the Enterprise

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

Confidence or Con? The Psychology of Tech’s Boldest Leaders

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 pr

Never Do the Same Work Twice: Rethinking CI for the Agent Era with Dan Manges

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, pre

AI News - Mid-October 2026

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 mel

Agents Are Identities Too: Identity Security After CyberArk with Amy Blackshaw

Brandon interviews Amy Blackshaw, Senior Vice President of Identity Marketing at Palo Alto Networks, about identity security in the age of AI agents. Blackshaw, who spent

A Cloud Nobody Owns: Sovereign Infrastructure for the Agent Era with Dominic Williams

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

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,

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

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 co

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 commi

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-pa

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 over

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 fr

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 envi

How Open-Source is Reshaping the AI Infrastructure Stack

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 reshapin

Vitamins vs. Pain Killers vs. Whippets - The Enterprise AI Adoption Problem

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 st