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The Enterprise AI Show

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  • The Enterprise AI Show

    AI News - Mid-November 2026

    15-11-2026 | 46 Min.
    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
  • The Enterprise AI Show

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

    11-11-2026 | 21 Min.
    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
  • The Enterprise AI Show

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

    08-11-2026 | 28 Min.
    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
  • The Enterprise AI Show

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

    04-11-2026 | 25 Min.
    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
  • The Enterprise AI Show

    AI & Cloud News - End of October 2026

    01-11-2026 | 41 Min.
    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
Meer Management podcasts
Over 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
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