The Enterprise AI Show

The Enterprise AI Show

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The Enterprise AI Show episodes

  • AI News - Mid-November 2026

    Brian and Brandon discuss the stunning resignation of NVIDIA CEO Jensen Huang, a story big enough to push election results, Anthropic’s IPO news, and a week of earnings off the agenda. They walk through what has been reported so far: relationships, including one with an executive tied to Megaspeed, a Southeast Asian cloud provider alleged to have funneled NVIDIA GPUs into China, and claims that security staff asked someone who photographed Huang to sign an NDA. Brandon cites Georgia coach Kirby Smart’s “dogs don’t beat dogs” to argue that CEOs have to follow their own company’s policies before anything else matters. To succeed interim CEO Colette Kress, Brian floats Tim Cook, Lisa Su, and Andy Jassy, while Brandon adds Lip-Bu Tan and Rene Haas and suggests NVIDIA may need a team of fixers to restructure Huang’s 60 direct reports. They debate whether extreme wealth breaks a leader’s judgment, and why success makes people afraid to call unusual practices strange. Brandon predicts NVIDIA will be fine because product-market fit covers a lot of mistakes, though AMD and Google’s TPUs get an opening. Brian warns that proven export violations could bring felony charges, large fines, and restated numbers. They close on who leaked the story and why now, with Brian suspecting that the US intelligence and military community saw a political window open after the midterms.

     

     

    SHOW: 1080

    SHOW VIDEO: https://youtu.be/IeFDTftW2tA

     

     

    SHOW SPONSORS:

    • Nord Security - NordLayer AI Scout

     

     

    SHOW LINKS

    • The Enterprise AI Show
    • NVIDIA Announces CEO Transition
    • Megaspeed and the Limits of US AI Export Controls (Tom’s Hardware)
    • Culper Research’s May Short Report on NVIDIA’s China Exposure (Daring Fireball)

     

     

    GUEST BIO

    N/A this week

     

     

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow
    46 min
  • 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 argues the biggest divide is between people who have only used a chatbot and those who have “touched the superpower” by using AI to finish a task that once took too long to attempt, and he says a CFO who only sees the token bills can’t see the value those tokens created. Brian traces enterprise adoption through several phases, from AI policies that mostly meant buying Microsoft Copilot, to employees pushing for Claude Code and Codex, to a token-maxing push with no clear goal. He compares the moment to early cloud, when Adrian Cockcroft’s Netflix talks split the industry into believers and companies that couldn’t imagine getting there, and predicts a bumpy year and a half in which some companies pull back, many search for balance, and a few race ahead. Brandon pushes back on the term vibe coding, arguing that nobody really writes code anymore and that AI is the best developer most people have ever worked with. He describes running a beta program where he pastes emailed feedback into an agent and ships a fix within half an hour, then has a second agent from another provider run a security audit. They agree AI can be a single-player game that rewards people willing to experiment, and Brandon closes with advice to replace “yeah, but” with “what if.”

     

     

    SHOW: 1079

    SHOW VIDEO: https://youtu.be/oTRgH0nRnvM

     

     

    SHOW SPONSORS:

    • Nord Security - NordLayer AI Scout

     

     

    SHOW LINKS

    • The Enterprise AI Show

     


    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow
    22 min
  • 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 end of 2026. Brandon says he would start in the research group, hunting for breakthroughs that could serve markets like finance and healthcare, and raises contextual ads even though he jokes the idea could get him fired. Flipping Alex Karp’s warning about AI systems learning a company’s differentiation, Brian proposes a product that sits between employees and their data, then shows executives where to cut costs in the 70 to 80 percent of work he estimates doesn’t set them apart. Pointing to Sierra’s outcome-based pricing, Brandon suggests Anthropic take over a system, absorb the risk, and get paid only when it delivers. His AI-assisted car purchase leads to a discussion of opt-in, intent-based commerce, and Brian argues Anthropic still lacks the kind of aggregation point he sees as the biggest way to make money. They close on Brandon’s half-joking plan: wait until the model is smart enough, then ask it how to make money.

     

     

    SHOW: 1078

    SHOW VIDEO: https://youtu.be/X5jtuUbcvbY

     

     

    SHOW SPONSORS:

    • Nord Security - NordLayer AI Scout

     

     

    SHOW LINKS

    • The Enterprise AI Show
    • Anthropic’s Form S-1 registration statement (SEC)
    • Palantir’s CEO Just Called Out OpenAI and Anthropic (MarketBeat)
    • Outcome-based pricing for AI agents (Sierra)
    • Cisco lets a 27-year-old refactor 98% of its legacy code with unlimited AI tokens (Fortune)
    • Aggregation Theory (Stratechery)

     

     

    GUEST BIO

    N/A this week

     

     

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow
    29 min
  • 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.

     

     

    SHOW: 1077

    SHOW VIDEO: https://youtu.be/C8MY3IhJtXM

     

     

    SHOW SPONSORS:

    • Nord Security - NordLayer AI Scout

     

     

    SHOW LINKS

    • The Enterprise AI Show
    • Anthropic’s S-1 filing
    • Redesigning source control at Anthropic
    • COBOL Modernization with AI: Breaking the Cost Barrier
    • Bending Spoons
    • Palantir CEO Alex Karp’s CNBC interview
    • Bun 1.4 Rewritten In Rust
    • Stack Overflow Went From 200,000 Monthly Questions to Nearly Zero

     

     

    GUEST BIO

    N/A this week



    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow
    26 min
  • 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.

     

     

    SHOW: 1076

    SHOW VIDEO: https://youtu.be/Ryn5wwb5afY

     

     

    SHOW SPONSORS:

    • Nord Security - NordLayer AI Scout

     

     

    SHOW LINKS

    • The Enterprise AI Show
    • Cisco hands a 27-year-old unlimited AI tokens to rewrite 98% of its legacy code (Fortune)
    • Amazon Q3 earnings: AWS grows 39% as advertising misses (CNBC)
    • Microsoft reveals Azure earnings for the first time (DCD)
    • Microsoft offers buyouts to 60,000 staff, about 27% of its workforce (Dealroom)
    • Anthropic files S-1 with the SEC for proposed IPO

     

     

    GUEST BIO

    N/A this week

     

     

    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow
    42 min
  • 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.



    SHOW: 1075

    SHOW VIDEO: https://youtu.be/yS2HEiGbxqo



    SHOW SPONSORS:

    • Nord Security - NordLayer AI Scout 



    SHOW LINKS

    • TheEntAIShow #1009 - OpenClaw with Sally O’Malley
    • OpenShell - the safe, private runtime for fleets of autonomous AI agents
    • OpenClaw Enterprise - An open source, vendor neutral platform for managing persistent agents in sensitive environments.



    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.



    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow
    43 min
  • 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

    SHOW VIDEO: https://youtu.be/DXmB8_YwNRQ



    SHOW SPONSORS:

    • Nord Security - NordLayer AI Scout 



    SHOW LINKS

    • The Enterprise AI Show


    GUEST BIO

    N/A this week



    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow
    28 min
  • 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 



    SHOW SPONSORS:

    • Palo Alto - Secure every identity with Idira by Palo Alto Networks 
    • Nord Security - NordLayer AI Scout 



    SHOW LINKS

    • RWX
    • Honeycomb switches to RWX for agent-ready CI/CD
    • AI Amplifies Existing Practices: Lessons from Our AI Shift
    • How Datadog Rebuilt Git Serving for CI (gitretriever)



    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:

    • LinkedIn: dmanges
    • Twitter/X: @dan_manges
    • GitHub: dan-manges
    • Medium: @dan_manges
    • Website: dan-manges.com



    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow
    42 min
  • 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

    SHOW VIDEO: https://youtu.be/Kp7AH_IdwIg



    SHOW SPONSORS:

    • Nord Security - NordLayer AI Scout 
    • Palo Alto - Secure every identity with Idira by Palo Alto Networks 


    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow
    37 min
  • 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 four years leading product marketing at CyberArk before Palo Alto Networks acquired it in February 2026, explains how identity management evolved from an IT operations task into a security discipline, and why identities now need to be protected across their full lifecycle. She walks through the three segments of identity security (access management, privileged access management, and identity governance), argues that human-driven quarterly access reviews are painful and error-prone, and says vendors like Palo Alto Networks are pulling governance into the identity security platform and using AI-driven roles to pre-approve most access.


    Blackshaw describes how frontier AI models change the attack landscape, with the cost of entry dropping toward zero and attackers moving at machine speed. She cites Unit 42 figures on how fast intrusions reach data exfiltration, an initial access time of about 25 minutes, and a recent investigation in which the full attack took under 10 hours. Her answer is control alongside detection and response: zero standing privileges and just-in-time access, so an attacker who steals a credential reaches a dead end. She and Brandon discuss why the most boring attacks, like a weak password and no second factor, are often the most effective, and why attackers often succeed with hard-coded machine credentials.


    On agents, Blackshaw says an agent is a machine identity with human-like traits: it can reason, decide, and escalate its own privileges, and you can't MFA it. She argues agents should be first-class identities with least privilege, just-in-time access, lifecycle governance, and a gateway for policy. For human-in-the-loop agents, the person is the anchor and must approve the moments that matter, with guardrails against consent fatigue. For autonomous agents, policy is the anchor, with tightly set permissions, behavior monitoring, and a kill switch. Brandon and Blackshaw also cover how to apply zero standing privilege for admins, developers, and agents without slowing developers down, and why policy and context (time, location, and usual behavior) should decide access. They close on who owns identity, which now rolls up through the CISO and increasingly reaches the CIO and CEO, why identity and security operations teams need to share data, and Blackshaw's case for platformization in a fragmented security market.



    SHOW: 1071

    SHOW TRANSCRIPT: The Enterprise AI Show #1071 Transcript

    SHOW VIDEO: https://youtu.be/CcaFoJRu0YM



    SHOW SPONSORS:

    • NordLayer - Use ENTERPRISE10 for 10% off
    • Palo Alto - Secure every identity with Idira by Palo Alto Networks 



    SHOW LINKS

    • Pathways to Identity Security Success
    • SC World: Palo Alto Networks launches Idira
    • IdentitySecOps: The Closed-Loop Model for AI-Speed Defense
    • Unify Identity and Security Operations to Stop AI Attacks (ebook)
    • Unit 42 Frontier AI Defense
    • Frontier AI and Identity Security in Financial Services (Q&A)
    • Cortex XSIAM
    • Palo Alto Networks Idira
    • Prisma AIRS
    • Amy Blackshaw: You Do Not Have Three Years
    • 2026 Unit 42 Global Incident Response Report



    GUEST BIO


    Amy Blackshaw is Senior Vice President of Identity Marketing at Palo Alto Networks, where she leads marketing for the identity business unit under the Idira brand. She has spent almost 20 years in cybersecurity, most of it in product marketing at large vendors, including four years leading product marketing at CyberArk, the pioneer of privileged access management, which Palo Alto Networks acquired in February 2026.


    Contact Amy Blackshaw:

    • Amy Blackshaw on LinkedIn



    FEEDBACK?

    • Email: show @ the enterprise ai show dot com
    • Bluesky: @TheEntAIShow.bsky.social
    • Twitter/X: @TheEntAIShow
    • Instagram: @TheEntAIShow
    42 min

About The Enterprise AI Show

From the publisher's feed

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…

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