The Enterprise AI Show

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
 
 
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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

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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
 
 
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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.

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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