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AI & TECH

Enterprise security collapses under AI agents, forcing billion-dollar rethink

Sunday, May 31, 2026 · from 5 podcasts
  • Legacy security tools are blind to AI intent, letting authorized agents accidentally wipe databases.
  • Enterprises distrust Anthropic and OpenAI as auditors because their data-hungry models compete with privacy.
  • Kirkland & Ellis commits $500M to its own AI platform to avoid vendor capture and commoditization.
  • Independent oversight requires cheap models that flag anomalies without slowing business workflows.

Traditional enterprise security is built for humans clicking buttons. It fails catastrophically when AI agents start managing workflows, according to Maxim Bar Kogan, CEO of Onyx Security. A system authorized to manage a database can see a ‘delete’ command as legitimate, even if the agent hallucinated the request. Identity management tools lack the context to interpret intent. Enterprises are granting agents broad access for productivity, creating a massive, autonomous error surface.

Kogan argues this is not a problem labs like OpenAI or Anthropic can solve. They are the car dealers; enterprises need an independent safety inspector. Firms are unwilling to hand historical interaction data back to labs that might use it to train future models. Onyx’s solution uses small, specialized ‘not smart’ models to flag anomalies in real-time, reserving expensive frontier model analysis only for critical moments. It mirrors blitz chess: intuition for 90% of moves, deep calculation for the high-stakes ones.

“If I pay $1 for a task, I can’t pay $2 for a second LLM to watch the first. That’s just a financial non-starter.”

- Maxim Bar Kogan, No Priors: Artificial Intelligence | Technology | Startups

The economic model for this new oversight layer depends on an agent economy that itself is breaking the internet. Cloudflare CEO Matthew Prince predicts AI agent traffic will exceed all human traffic by early 2027. Agents don’t click ads. They strip-mine the web for data and never send a visitor - or a payment - back to the source. Publishers collapse, and the data AI needs to learn stops being produced.

Prince says the only fix is a payment layer capable of 100 million transactions per second, a scale no current blockchain supports. Until that plumbing exists, the internet remains trapped in an “advertising slum” agents cannot navigate. The call for an independent, high-speed payment system mirrors the call for an independent, high-speed security layer: both are foundational infrastructure the original internet failed to build.

“AI agent traffic will exceed all human internet traffic in the first half of 2027. The economic foundation of the independent web is collapsing.”

- Matthew Prince, Bankless

Institutional players are already building their own moats. Kirkland & Ellis, the world’s largest law firm, is committing $500 million to a private AI platform, with $100 million allocated this year. According to The AI Daily Brief, Chairman John Bailis sees general tools like Harvey as raising the industry floor. Kirkland is paid for the ceiling. The spend is a defensive maneuver against middleman risk - if legal AI vendors eventually serve corporate clients directly, firms without proprietary tech become redundant.

On the user side, privacy is becoming a currency. Milan, co-founder of NanoGPT, says Monero has been the platform’s most-used payment method for ten months straight. Users funding ‘agentic’ workflows - software that manages its own wallet to buy compute - are removing the human from transaction logs. They are also deploying local 500-million parameter models in their browsers to act as private memory layers, preventing large labs from building a searchable database of their lives.

The core challenge is a structural one. Labs compete on intelligence, enterprises demand privacy, and the entire ecosystem needs oversight that doesn’t kill productivity. The $500 million law firm build-out, the push for 100M TPS payments, and the rise of Monero-driven compute all point to the same conclusion: the old centralized models are breaking. The new ones are being built in parallel, by players who refuse to be captured.

Source Intelligence

- Deep dive into what was said in the episodes

Claude Opus 4.8 First ImpressionsMay 29

  • Kirkland & Ellis plans to spend $500 million building its own internal AI platform, with $100 million allocated this year and continued investment over 3-4 years.
  • Kirkland's AI system will function as an extensive internal knowledge base aggregating partner-level insights, aiming to replace other software and shift from billable hours toward value-based pricing.
  • Cognition's enterprise usage is up 10x this year, reaching a $500M revenue run rate, while internal code commits by its Devin agent grew from 17% in January to 89% currently.
  • Mark Zuckerberg told shareholders Meta could pivot to an AI cloud business, citing weekly inbound requests for API services and compute sales at a premium.
  • Microsoft is reportedly set to release its first commercial family of AI models at Build, including specialized models for coding, reasoning, transcription, speech, and images.
  • Anthropic launched Dynamic Workflows in Claude Code, a multi-agent feature that spins up hundreds of sub-agents for parallel tasks like security audits, exemplified by porting 750k lines from Zig to Rust with a 99.8% test pass rate.
  • Anthropic announced Project Glasswing, previewing a 'Mythos-class' model with higher intelligence than Opus for cybersecurity, with a general release planned in coming weeks.
Also from this episode: (5)

Startups (1)

  • Cognition, the AI coding startup, closed a $1B funding round, valuing the company at $26B - more than double its valuation from September.

AI & Tech (4)

  • Anthropic released Claude Opus 4.8, positioning it as a refinement focused on improved honesty and judgment over raw performance gains.
  • Opus 4.8's benchmark scores show moderate gains: SweetBench Pro increased from 64.3% to 69.2%, HumanEval from 54.7 to 57.9, and TerminalBench 2.0 from 66.1 to 74.6. Its GDP-Val score rose from 1753 to 1890.
  • Early testers note Opus 4.8 is more thorough and 4x less likely to bluff than its predecessor, though some found its coding and writing performance highly dependent on using the extra-high reasoning level.
  • Anthropic closed a Series H round at a $965B valuation, more than doubling its $380B valuation from February, and reported its revenue run rate crossed $47B this month.
No Agenda Show
No Agenda Show

Adam Curry

1872 - "Lunar Economy"May 28

Also from this episode: (10)

Media (1)

  • Adam Curry criticizes mainstream media for not fully covering President Trump's televised cabinet meetings, noting they report only on gaffes like threatening to 'blow up Oman' while ignoring detailed agency reports on fraud prosecutions and economic data.

Business (3)

  • Treasury Secretary Scott Besson announced the rollout of a Trump savings account app, revealing that six million children are already signed up for IRA-style accounts with a $5,000 annual parental contribution limit and a $1,000 federal donation for children born 2025-2028.
  • John Dvorak cites a CNBC analyst predicting Alaskan oil exports to China will grow, supported by Interior Secretary Doug Burgum's report of over $4 billion in federal lease sale revenues from the Permian, Bakken, and North Slope in five months.
  • JPMorgan Chase CEO Jamie Dimon warned New York Mayor Mamdani that anti-business policies and 'tax the rich' agendas are driving wealth and taxpayers out of the city, following a tense meeting.

Politics (4)

  • Vice President Vance reported that the administration's fraud task force took over 400 law enforcement actions, including arrests and indictments, in 51 days, targeting billions in pandemic-era fraud, including a cancelled $2 billion EPA grant to Stacey Abrams.
  • Senator Marco Rubio stated the U.S. has secured third-country national agreements with 20 nations to deport undocumented migrants who refuse repatriation, a tactic that often incentivizes voluntary return.
  • John Dvorak notes media's repetitive 'faster than responders can contain' talking point on the Ebola outbreak in Central Africa, while questioning the efficiency of sending 100 tons of supplies for 200 suspected deaths.
  • Ken Paxton defeated incumbent John Cornyn in Texas's Republican Senate primary runoff, a race that cost $130 million making it the most expensive Senate primary in U.S. history.

AI & Tech (1)

  • Adam Curry argues AI cannot generate parody songs like 'Weird Al' Yankovic due to copyright restrictions, claiming such content would get episodes removed from platforms like Spotify despite no violation.

Society (1)

  • Law enforcement officials in Polk County, Florida and Chicago propose holding parents criminally liable for teen takeovers, with Chicago weighing a Class A misdemeanor charge carrying up to a $2,500 fine and 364 days in jail.

Building an AI Guardian for Enterprise with Onyx Security CEO Maxim Bar KoganMay 28

  • Onyx Security trains models and builds agents to oversee other AI agents, aiming to detect illegitimate actions as enterprise AI adoption grows exponentially.
  • Maxim Bar Kogan states autonomous agents like coding assistants are the fastest-growing category in enterprises, outpacing low-code automation platforms.
  • Kogan argues existing security tools like identity management and API monitoring lack the context to understand the intent of flexible AI agents, creating new control gaps.
  • Onyx's approach uses small, specialized models to efficiently flag high-risk AI actions, reserving more powerful analysis only for critical moments to manage cost and latency.
  • Kogan sees Mithril-level AI models dramatically lowering the cost of vulnerability discovery, forcing security teams to implement foundational controls quickly.
  • He believes independent oversight is crucial because enterprises distrust vendors auditing their own products and need solutions adaptable to multiple AI providers.
  • Kogan notes enterprises are unwilling to share historical agent behavior data with Anthropic or OpenAI due to those companies' data-hungry training practices.
  • Auto-GPT's early demonstration of autonomous agents ignited market imagination, highlighting the potential and risks of AI performing complex computer tasks.
  • Kogan asserts the core challenge of AI oversight is interpreting agent intent, not just proxying data, which requires understanding what AI systems 'think'.
  • Onyx's founding insight was the need to control increasingly smart AI agents, especially as they begin managing critical infrastructure like power grids.
Also from this episode: (4)

Startups (1)

  • The Israeli tech ecosystem excels at understanding security team workflows and building products tailored to their daily operational needs, according to Kogan.

AI & Tech (3)

  • He predicts mechanistic interpretability of AI models will advance significantly as smarter AI systems emerge, aiding in understanding and controlling intelligence.
  • Financial institutions like JP Morgan adopt AI cautiously due to high risk profiles, contrasting with startups that aggressively deploy agents to gain competitive edge.
  • Kogan advocates for gradual, controlled release of Mithril-level AI models to allow enterprise security teams time to develop defenses and prevent catastrophic failures.

AI Sub Slave VS NanoGPT with Milan | FREEDOM TECH FRIDAY 41May 26

  • Milan explains NanoGPT offers subscription and pay-per-prompt access to hundreds of text, image, video, and audio AI models through a single interface, with strong privacy defaults and crypto payments.
  • Milan founded NanoGPT as a Telegram bot to let people pay small amounts in crypto to try ChatGPT, aiming to make AI accessible without credit cards or personal data after his own privacy experiences at a central bank.
  • Milan says NanoGPT prioritizes privacy by default, allowing use without accounts and storing data locally, but added optional encrypted storage and Google sign-in for users who want syncing.
  • Milan explains NanoGPT supports around twenty cryptocurrencies, with Monero being the most used for ten months, followed by Bitcoin and Nano, to meet users where they are and foster a circular crypto ecosystem.
  • Milan outlines NanoGPT pricing: a $12 monthly subscription for open-source models with a 30-60 million token weekly allowance, or pay-per-prompt starting at $1, where costs vary widely based on model and task complexity.
  • Milan notes users can optimize costs by using expensive models like Claude Opus as orchestrators and cheaper models for simple tasks, or by setting spending limits and choosing between premium, standard, or basic auto-model routing.
Also from this episode: (12)

AI & Tech (10)

  • Milan says OpenAI's GPT 5.5 and Anthropic's Claude Opus 4.7 are the leading closed-source AI models for general chat and coding. Claude Opus 4.7 is used five times more than any other model on NanoGPT.
  • Milan states Google's Gemini 3.5 Flash is a top closed-source model because it is very fast and cheaper, while Opus 4.7 is expensive and slower.
  • Milan argues open-source text models like GLM 5.1, DeepSeek V4 Pro, and Kimi K 2.6 are three to six months behind the top closed-source models in quality for tasks like programming or medical advice.
  • Milan notes open-source competition drives down AI model costs and increases efficiency, while closed-source models have fixed prices due to monopolies from providers like OpenAI or Azure.
  • Milan observes running top AI models locally on consumer hardware like a MacBook or phone is currently unrealistic due to their size, but smaller image models are more feasible for local use.
  • Milan says proprietary image models like Midjourney and GPT Image 2 offer higher quality than open-source options, but they impose stricter content censorship than local fine-tuned models.
  • Milan describes users employing NanoGPT for creative applications like detailed role-playing in constructed worlds and automated polymarket betting operations where AI agents research and place wagers.
  • Milan states NanoGPT's development is driven 90% by user feedback, leading to additions like video and audio models, APIs, trusted execution environments, and a browser-installed local model for memory.
  • Milan demonstrates NanoGPT's local model feature, which downloads a 500 million parameter model directly in the browser for tasks like conversation memory, aiming for accessibility on basic devices.
  • Milan explains NanoGPT's global memory uses a local model to learn user background details across chats, while context memory expands a model's window by feeding it only the most important parts of long conversations.

Coding (1)

  • Milan says NanoGPT's OpenAI-compatible API allows integration with any coding harness or agent tool like Claude CLI, and its agents page provides endpoints for web search, image generation, and other functions discoverable by AI models.

AI Infrastructure (1)

  • Milan advises starting AI agent setups in a sandboxed environment like a separate computer or VPS and using AI models themselves to configure the workflows, rather than giving them blind access to emails or local files.

Cloudflare Needs 100M TPS from Crypto to Fix the Internet | CEO Matthew PrinceMay 25

  • Matthew Prince predicts AI agent traffic will exceed all human internet traffic in the first half of 2027, creating a business model crisis because agents don't click on ads or pay subscriptions.
  • Prince explains Cloudflare started as a cloud-based firewall and grew by solving emergent problems for clients, now serving 20% of the internet, 80% of major AI labs, almost 100% of crypto companies, and a rising share of Fortune 500 firms.
  • Prince clarifies Cloudflare's Content Independence Day gave all customers tools to control AI crawler access, not a blanket block, because many sites want their content in AI systems.
  • Prince states Cloudflare is working on the 402 payment standard with Coinbase and others, seeking a stablecoin solution that can scale to 100 million TPS, which no existing blockchain supports.
  • Prince warns the natural tendency is toward extreme centralization, with few AI companies, content creators, and giant corporations dominating agent commerce, bypassing small businesses.
Also from this episode: (11)

AI & Tech (9)

  • Prince describes Cloudflare's defensive role, handling tens of millions of attacks per second and protecting Ukraine's internet, which led to his personal sanction by the Russian government.
  • Prince says internet website creation plateaued from 2011-2012 until recently, but is now growing again at early-2000s rates due to tools enabling more creators and developers.
  • Prince contends AI answer engines like ChatGPT are strip-mining the web, pulling content without sending human traffic back, causing a step-function drop in ad revenue for publishers and threatening their survival.
  • Prince says AI subscriptions could create a global information divide, shrinking the internet for those in the global south who cannot pay, while trustworthy, unbiased agents become a premium product.
  • Prince predicts AI companies will evolve like YouTube, competing by securing unique content niches and compensating creators, potentially leading to a golden age of knowledge-focused content.
  • Prince notes Google has vastly more web data than competitors: it sees four times more pages than OpenAI, five times more than Microsoft, six times more than Anthropic, and 22 times more than X.ai.
  • Prince argues creators must control who accesses their content because if agents consume it without compensation, the creators' business model collapses.
  • Prince envisions a future where AI companies identify gaps in human knowledge and compensate creators to fill them, moving from a traffic-based to a knowledge-creation economy.
  • Prince observes that local, unique content like his Park Record newspaper is becoming more valuable to AI companies than generic national news, and may earn more from AI licensing than digital ads.

Big Tech (1)

  • Prince argues Google's ad-driven business model, which rewarded traffic, degraded into a rage-bait economy, fueling populism and division by incentivizing incendiary headlines over knowledge creation.

Protocol (1)

  • Prince says a micropayment system is essential for the new internet economy, but current crypto rails cannot scale to the needed volume of 5-50 million monetizable transactions per second Cloudflare handles.