• 25 minutes 53 seconds
    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. Brandon argues the natural next step after Claude Code is rules-based back office work like tax, accounting, and finance, and he floats a free Claude tool that prepares a basic 1040 tax return as a national proof of concept, which raises the question of whether Anthropic wants to take on Intuit directly. Brian sees a Claude version of the ERP as a logical target, given how much customers dislike the consultants and constant data integration that come with those systems, though it would mean entering SAP and Oracle territory. They also weigh whether Anthropic would announce these moves or let them emerge quietly, with Brian pointing to its claim that it could rewrite mainframe code, which he says sent IBM’s stock down, and Brandon predicting most of it will be emergent. The boldest ideas build on Bending Spoons: Brandon proposes “Claude Equity,” where Anthropic buys companies and runs them with a few people and AI, while Brian imagines using IPO money to build cheap replacements that drive down incumbents’ value before buying or swapping them. Brandon cites Anthropic’s new source control work as a possible shot at GitHub, but Brian warns that at the growth investors may expect, replacing GitHub is like a fly on a horse’s back.

     

     

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    N/A this week



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    4 November 2026, 6:00 am
  • 41 minutes 44 seconds
    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 unlimited AI tokens to rewrite 98% of Cisco’s legacy code in 24 months. Brandon likes the audacity but argues the odds improve with more believers who know the systems being rebuilt, while Brian, a 14-year Cisco veteran, recalls an earlier Cisco team that won a blank check to work only on cool projects and warns the friction lands on people, not ideas. On cloud earnings, Brian notes Microsoft now breaks out Azure at about $29 billion a quarter, with Google Cloud near $25 billion and AWS at almost $46 billion, while both point to advertising misses at Amazon and Google as fuel for investor worry about who pays for the AI buildout. Brandon urges Microsoft employees offered buyouts to take them and become the AI experts other enterprises need. The episode closes on Anthropic’s S-1: Brandon argues demand is the only number that matters and that people underestimate exponential growth, while Brian counters that Anthropic is far from profitable, carries compute commitments it can’t exit, and is rushing to market as growth slows.

     

     

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    N/A this week

     

     

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    1 November 2026, 6:00 pm
  • 42 minutes 24 seconds
    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 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 credentials (a supervisor egress proxy injects them from outside), kernel features like Landlock restrict what they can touch, and when a blocked agent hits a wall, OpenShell can ask it why it tried, so a human can decide whether to allow the action now or never. Running real agents in that sandbox showed them that not everything should be untrusted. Memory, for example, is an enterprise record. That insight led them to OpenClaw’s own push to decompose agents into trusted and untrusted parts. OpenClaw Enterprise borrows the Hypershift hosted control plane pattern: gateways, memory, and session state live on a control plane cluster, while agent harnesses run in disposable OpenShell sandboxes on a data plane cluster, so a failed sandbox is simply replaced with full context. Enterprises set a permission ceiling; every new agent starts least privileged and grows only up to that limit, and blessed templates for roles like team Q&A, software co-development, and chief of staff make good agent setups repeatable instead of tribal knowledge. The guests also highlight multi-user agents, where colleagues steer the same agent together rather than flooding each other with AI-generated pull requests, and Skipper, the project’s own support agent that preserves the reasoning behind past decisions. The stack is model-agnostic and runs anywhere, including on self-hosted inference such as Dynamo or llm-d. With more than 3,000 pull requests merged since its September launch, the project is targeting a 1.0 release around year-end, with enterprise pilots and production rollouts expected in 2027.



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    GUEST BIO(s)

    Derek Carr is a Senior Distinguished Engineer at Red Hat, where he has worked on OpenShift and in the Kubernetes community since 2014. He is a former member of the Kubernetes Steering Committee and has held long-running leadership roles in Kubernetes SIG Node and SIG Architecture. His recent work focuses on how enterprises can run AI agents safely on Kubernetes, including Red Hat’s work with NVIDIA’s OpenShell on kernel-enforced agent sandboxing.

    Mrunal Patel is a Distinguished Engineer at Red Hat, where he has worked on Linux containers, Kubernetes, and OpenShift since 2011. He started the CRI-O container runtime, is a maintainer of runc and the OCI runtime specification, and serves as a chair and technical lead of Kubernetes SIG Node. With Derek, he is now applying deep container isolation expertise to secure execution for AI agents on Red Hat AI.



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    28 October 2026, 5:00 am
  • 27 minutes 31 seconds
    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 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 profile ties a founder’s identity more tightly to a story they must defend at all costs. Brandon describes a “contrarian effect,” in which a venture model with low hit rates rewards bold founders and tells them they are special. He recommends The Halo Effect as an antidote to success stories that confuse correlation with causation. They also question the VC preference for founders with hardship backstories. The conversation closes on Brandon’s framework of operators, believers, and pragmatists, and why every organization needs pragmatists willing to question big promises before they become fiction.



    SHOW: 1074

    SHOW TRANSCRIPT: The Enterprise AI Show #1074 Transcript

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    N/A this week



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    25 October 2026, 6:00 pm
  • 41 minutes 4 seconds
    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, 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 loops push people (and agents) into costly context switching.


    Manges describes how RWX differs from traditional CI platforms. Instead of splitting pipelines into jobs that each spin up a virtual machine and repeat the same setup, RWX models work as a directed graph of tasks with declared dependencies, so everything runs with maximum parallelization and only once. He cites Datadog's recent blog post about the strain that cloning code across so many parallel jobs put on its Git servers. Failures can be retried from the point of failure, and compute can be sized per step. He explains that RWX uses content-based caching rather than Docker's lineage-based caching, so a cache miss can be followed by a cache hit and only the work affected by a change runs. Under the hood, he says, RWX built its own distributed container runtime on the same low-level primitives as Docker, runs on AWS, and is hosted by default, with an option to run inside a customer's own VPC.


    On agents, Manges says every RWX workflow can run from a CLI without a commit and push, which gives agents a fast, synchronous, more accurate and token-efficient loop. He recommends telling agents to run the CI workflow before they open a pull request, so the status check goes green instantly through caching, and argues there is no longer a reason for a human to be in the loop for build failures. He notes that review practices will vary widely, from thorough human review to software factory automation, and mentions a customer that has agents write throwaway Playwright tests for QA. He describes Honeycomb's move from CircleCI, which he says doubled their PR velocity, and the "AI legible CI" they describe. Looking ahead, Manges says the bottleneck in software engineering is shifting from writing code to validating it, and that RWX is expanding into sandboxes, preview apps, and custom webhooks. He says customers have asked about code hosting and review, but he promises nothing.



    SHOW: 1073

    SHOW TRANSCRIPT: The Enterprise AI Show #1073 Transcript

    SHOW VIDEO: https://youtu.be/2QnbYmRltgM 



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    GUEST BIO

    Dan Manges is the co-founder and CEO of RWX, a cloud platform for running CI/CD and other automation for engineering teams and their coding agents. He was previously the founding CTO of Braintree, the payments company that acquired Venmo and was acquired by PayPal, and co-founded car insurance carrier Root, which went public in 2020.

    Contact Dan Manges:



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    21 October 2026, 5:00 am
  • 36 minutes 19 seconds
    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 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 have reportedly jumped from around 7% to about 15%, adding to Oracle’s contract pullback as yellow flags for the neocloud and data center layer. Meanwhile, Anthropic and OpenAI keep pulling in revenue even as enterprise CIOs struggle to find ROI. Brandon weighs Andrej Karpathy’s claim that only a few thousand people have seen what AI can really do against the labs’ opposite storytelling styles. The pair also question why Meta keeps promoting its frontier models when its Muse personal agent looks like the real monetization story. They close on whether software fundamentally changed in the last two weeks. Brandon argues AI has put professional-grade app building within reach of millions, pointing to his upcoming PodEditor app, but says finding demand and building a business are as hard as ever. They see Bending Spoons’ model of running acquired apps with AI and a skeleton crew as a possible playbook for established vendors.



    SHOW: 1072

    SHOW TRANSCRIPT: The Enterprise AI Show #1072 Transcript

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    18 October 2026, 11:00 pm
  • 41 minutes 45 seconds
    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-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 stack of software running down to the silicon can never be fully secured, so he wanted a cloud created by a network protocol, where software is tamper-proof, always on, and secure by default without firewalls, patches, or security and sysadmin teams.


    Williams walks through how it works. Code compiles to WebAssembly and runs in persistent memory, replicated across independent nodes using Byzantine fault tolerance, so there is no database or file system to connect to, and a misbehaving node, even a "Dr. Evil" one, cannot corrupt the result. Brandon presses on data protection, and Williams points to hardware encapsulation such as AMD SEV-SNP and the ability to choose trusted node providers. He then describes cloud engines, which let an enterprise pick nodes from a marketplace (hyperscalers, independent data centers, or on-prem), reconfigure them without downtime, and avoid vendor lock-in, with payment handled behind the scenes so it looks like a conventional cloud.


    On adoption, Williams says data sovereignty is a major driver, citing the U.S. CLOUD Act and governments, such as Pakistan, that want infrastructure they control and can inspect as open source. He describes Caffeine, which builds apps on the Internet Computer from a chat prompt, and Open SaaS, a suite meant to replace siloed SaaS tools with a single AI-aware system. To get started, he recommends pasting the prompt from the skills site into a coding assistant and having it write the back end in Motoko, a language designed for AI agents that guards against data loss when upgrading apps in production. Cloud engine coupons are expected to open up soon.



    SHOW: 1070

    SHOW TRANSCRIPT: The Enterprise AI Show #1070 Transcript

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    Dominic Williams is the founder, president, and chief scientist of the DFINITY Foundation, the Zurich-based non-profit behind the Internet Computer, which he began developing in 2015 and launched in 2021. A longtime engineer-entrepreneur focused on distributed systems, he previously founded the MMO game Fight My Monster and served as president and CTO of the Palo Alto incubator String Labs.



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    12 October 2026, 12:00 am
  • 43 minutes 3 seconds
    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

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    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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    7 October 2026, 5:00 am
  • 35 minutes 4 seconds
    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.



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    4 October 2026, 5:00 am
  • 25 minutes 10 seconds
    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. 

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    SHOW TRANSCRIPT: The EntAIShow #1067 - The Anthropic IPO?

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    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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    30 September 2026, 5:00 am
  • 28 minutes 52 seconds
    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

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    27 September 2026, 5:00 am
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