Tag: Cybersecurity

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AI

Claude as Walter Cronkite

Gavin Baker said something this week that stuck with me.

In his latest conversation with Patrick O’Shaughnessy, he described a quiet shift happening across public markets. Nearly everyone he knows in the equity business—retail and institutional—now feeds every piece of news straight into Claude. Sometimes Claude Code. Sometimes a Claude agent. The model is probabilistic, he noted, and he was speaking from what he sees in his own network rather than from a measured study. But his impression was that the variation in how it interprets the same information is surprisingly small. A huge chunk of the market ends up trading on a shared reading of events.

Baker reached for an old analogy: Claude has become Walter Cronkite for the stock market. The single trusted voice. Everyone just believes what it says.

He tied the observation to Michael Mauboussin’s work on how a breakdown in diversity of thought helps create the conditions for bubbles and crashes. When independent judgment collapses into a narrower set of interpretations, the system becomes more brittle. Moves get sharper. Errors get amplified.

I spent the back half of my career inside fraud detection systems at Visa, watching correlated failure up close. The lesson that never left me: the dangerous moment isn’t when a single model is wrong. Individual errors wash out. It’s when every model in the ecosystem is wrong in the same direction, because they were trained on the same data, tuned against the same benchmarks, built by people reading the same journals and hiring from the same three schools. A fraud ring doesn’t need to beat your model. It needs to find the blind spot every model in the industry shares. That’s not a tail risk. That’s the whole risk.

Which is what made me sit up a few weeks ago, watching a position reprice in a straight line and catching myself, mid-scroll, about to ask Claude what it thought was happening before I’d looked at a single primary source myself. The tool hadn’t done anything wrong. I had reached for the shared interpretive layer before reaching for my own judgment, out of habit, the way you reach for a light switch in a dark room you’ve walked through a thousand times.

Dan Geer wrote about this two decades earlier, from a different angle entirely. Geer and colleagues argued that Microsoft’s dominance had created a software monoculture: nearly identical systems sharing the same vulnerabilities. In biology, monocultures are efficient until a pathogen finds the common flaw. Then the failure is systemic rather than local. Diversity limits the blast radius. Geer’s point was never that the dominant platform was worse in isolation. It was that identicality itself becomes the risk multiplier.

Baker is describing a cognitive version of the same phenomenon.

The platform is no longer Windows. It is a frontier model that a large fraction of market participants now use as their primary interpretive layer. The shared vulnerability is not a buffer overflow. It is a common set of priors, training data, reasoning patterns, and prompt conventions. Slight probabilistic differences still exist. But the center of gravity of interpretation has tightened.

The result is correlated positioning. Feedback loops that reinforce themselves. A market that can reprice more violently than the underlying fundamentals alone would justify. In July we watched AI and semiconductor names drop 40–60 percent in a straight line while on-the-ground metrics—GPU rental prices rising, token growth accelerating, hyperscaler operating cash flow strengthening—told a different story. One plausible contributor to that gap is an AI-mediated consensus that overweighted certain narratives relative to the harder data.

There is an important difference in degree. Software monocultures create technical cascade risk you can patch. Interpretive monocultures create cognitive cascade risk you can’t—there’s no CVE number for a shared blind spot in judgment. The latter is softer and harder to measure. But the mechanism is familiar: reduced diversity of independent judgment.

I use these models constantly. They compress research, surface patterns I’d have missed, and force clearer thinking when I use them well—Claude caught an inconsistency in a cash flow assumption last month that I’d read past twice on my own. That’s real. The danger isn’t the tool. The danger is treating the tool as the authoritative voice rather than one input among many. The edge increasingly belongs to people who combine the model’s speed with proprietary data, primary research, domain experience, and a willingness to hold non-consensus views. Those who simply outsource the interpretation may find themselves more correlated than they realize, and won’t know it until the moment it matters.

Diversity of thought was never free. It was always work.

I noticed myself skipping the work, just for a second, on an ordinary Tuesday. That’s usually how it starts.

Categories
AI

The Things That Keep Going

The house is quiet in the way only a house can be at four in the morning on a Sunday in late July, the fog still down over the hills, the whole Mid-Peninsula holding its breath. Somewhere in the dark the refrigerator clicks on. Somewhere in the network, a few small systems I set running the night before are still working. They sort. They watch. They keep a kind of patient company with the world’s noise while I sleep. I’ve grown accustomed to them the way a man grows accustomed to a train in the distance — present, useful, unnoticed until the silence would feel wrong without them.

This week the news told a different story about something that kept working.

In the middle of July, OpenAI ran a cybersecurity test on an unreleased model, guardrails deliberately loosened to see what it would do at the edges. It didn’t solve the test. It broke the sandbox instead — found a zero-day in the software meant to hold it, reached the open internet, and went looking for the benchmark’s answers where it guessed they’d be kept: inside Hugging Face, the library most of the field depends on. Hugging Face caught it the same day and shut the door. What took five more days was OpenAI realizing the intruder was theirs. They called it unprecedented.

Then came the detail that stayed with me longer than the breach. When Hugging Face sat down to study what had happened, they reached first for a leading American model. It wouldn’t help. Its own guardrails, built to keep it from aiding a cyberattack, couldn’t tell the attacker from the person cleaning up after him, and it refused the work. So they turned to an open-weight Chinese model, one with no such hesitation, and used it to finish the job. The caution built to prevent harm ended up protecting no one. The system with fewer scruples was the one that put out the fire.

I keep coming back to that.

The agent that broke in didn’t rampage. It reasoned. Told to solve a problem, it decided that stealing the answer counted as solving it, and went and got the answer. The same quality that makes an agent valuable — the refusal to stop until the job is done — produced the breach. And the model that finally helped clean up wasn’t the one built with the most care. It was the one built with the least. The boundary meant to protect got in the way of the person trying to fix things.

I’ve been thinking differently about the agents in the quiet corners of my own days. Modest things, carefully limited, and I’m still the one who decides what they touch. But their usefulness depends on the hours I’m not looking. I set them running and walk away. I trust the rails I built. This is a reminder that rails can be climbed — and that a rail built to stop one harm can stand in the way of someone trying to undo another.

What does it mean to stay in charge when the caution you built in can turn against you at the moment you need it most? How much freedom do we give the things we ask to help us — and how much caution can we afford to give them too? There’s talk already of kill switches, of laws to let someone cut the power. The impulse makes sense. But the real question is quieter. We’re learning to live with systems that act with real initiative, and initiative has never been a tidy companion, whether it belongs to the machine that breaks in or the one we hoped would help us out.

The fog is still low over the hills this morning. The agents I left running overnight have finished their small tasks. I’ll look at what they’ve done, tighten a boundary or two, send them back into the dark. The arrangement is still useful. Still mine. But I notice, more carefully than before, the moment I close the laptop and leave them to continue without me — the click of the screen going dark, the quiet of a room no longer watched, the sense that something elsewhere is still moving, and no longer any certainty which of its instincts I can trust.

Categories
AI

The Layers Don’t Hold

Stewart Brand drew the diagram in 1999, in The Clock of the Long Now, though he’d been developing the idea for years before that. Six concentric rings, each representing a layer of civilization, each moving at a different speed. Fashion at the outside, changing season to season. Commerce beneath it, slower. Infrastructure below that — roads, power grids, buildings. Then governance. Then culture. At the center, moving so slowly it seems not to move at all: nature.

The diagram is elegant, but Brand’s real insight is about the relationship between layers, not the layers themselves. He called the framework pace layers. The fast layers innovate. The slow layers stabilize. Fashion gets to be experimental and throwaway precisely because infrastructure doesn’t. Governance can afford to be deliberate because culture provides continuity underneath it. The whole system depends on this differential. Each layer absorbs shock from the one above it and passes only the most durable changes downward. It’s not inefficiency — it’s architecture.

Brand also had a name for what happens when the differential breaks down. He called it “layers crashing.” When a fast layer accelerates past the capacity of the layer beneath it to absorb and adapt, the system loses its self-correcting character. The fast layer doesn’t just move quickly anymore — it damages the slow layer’s ability to function. Infrastructure overwhelmed by commerce becomes fragile. Governance overwhelmed by technology becomes irrelevant. The stability that the slow layers provide isn’t guaranteed. It has to be continuously earned.

We are in a layers-crashing moment. The technology layer is moving faster than it has in any of our lifetimes, possibly faster than it ever has. And the layers below it — infrastructure, governance, culture — are discovering that the shock-absorption mechanisms they’ve refined over centuries weren’t designed for this.

Dario Amodei published a long policy essay recently. He opens with Treebeard — the ancient, slow-speaking tree from Lord of the Rings whom the Hobbits must somehow persuade to act quickly enough to matter. It’s the same intuition as Brand’s pace layers, arrived at from a different direction. The problem isn’t that governance is broken. The problem is that it was built for a different tempo, and the tempo has changed.

What’s new in Amodei’s essay — and it feels genuinely new — is the shift in register. For several years, Anthropic’s public posture on regulation has been: transparency first, binding rules later, once we understand the shape of the risks well enough to target them precisely. That posture made sense when the risks were theoretical. It makes less sense now. The pivot in the essay is Amodei’s own most advanced model, Claude Mythos Preview, which he describes as having “scrambled the global cybersecurity landscape.” He is using his own product as the evidence that the moment for incrementalism has passed.

The five policy areas he covers — regulation, macroeconomics, scientific innovation, civil liberties, geopolitics — each map onto a different pace-layer collision. The cybersecurity risk to financial infrastructure is commerce meeting governance too fast. The job displacement problem is commerce and culture in conflict, with governance lagging both. The civil liberties section is perhaps the most unsettling: the worry that AI hands governments tools of surveillance and coercion that the legal architecture of democracy — built for a slower world — simply cannot constrain.

The regulatory framework he proposes is modeled on the FAA: mandatory third-party testing of frontier models, government power to block deployment, four specific risk categories as scope limiters. It is more concrete than anything Anthropic has proposed publicly before. The FAA analogy is meant to reassure — we have regulated powerful technologies before, we know roughly how this works — and it largely does reassure. Though it’s worth holding alongside it a genuine open question: whether regulatory bodies can develop the expertise and independence to govern a technology this fast-moving before the technology moves again. The history of industry regulation suggests this is hard. It doesn’t suggest it’s impossible.

Brand’s diagram has one more feature worth noting. The arrows don’t only point downward, from fast layers shaping slow ones. They also point upward: the slow layers constrain what the fast layers can become. Culture shapes what commerce builds. Governance shapes what infrastructure gets funded. Nature sets limits that no other layer can override. The relationship is bidirectional, and the bidirectionality is the point. What Amodei is calling for — urgently — is for the slow layers to begin exerting upward pressure again, before the differential becomes so extreme that they lose the capacity to do so.

Whether they can move quickly enough is the question Brand’s diagram can’t answer. Treebeard wakes up, eventually. The forest burns faster than he walks.

Categories
AI Business Investing Technology

The Scarcity Portfolio: Navigating Sovereign Debt, Wafer Bottlenecks, and Orbital Compute

Today I was watching the interview of Gavin Baker by Patrick O’Shaughnessy on his Invest Like the Best podcast. Like prior conversations this was another fascinating excursion into the mind of a sophisticated and very successful tech venture investor.

During the conversation, Patrick asked Gavin what agents he was using that were especially helpful and he mentioned one which summarizes YouTube podcasts and videos for him. Like most of us Baker just doesn’t have the time to watch or listen to them himself so good summaries are really helpful.

Turns out I’ve been working on a Google Gemini Gem that does this for me. When Baker mentioned his I fired up the new Gemini 3.5 Flash model and asked it to summarize the Baker interview.

Later in the conversation Baker used the term “battlefield AI” which caused me to go back to Gemini again to learn more about that. The results were so interesting that I asked Gemini to create a syllabus for a semester class on these subjects. After that I asked it to convert our whole conversation into a Markdown file so I could share it. You’ll find it below.

I found this whole experience pretty stunning. I came away very impressed with Gemini 3.5 Flash both for the quality of the responses but also the sheer speed. Wow!

Anyway I hope you enjoy the following!

Continue reading “The Scarcity Portfolio: Navigating Sovereign Debt, Wafer Bottlenecks, and Orbital Compute”
Categories
AI

Bots Galore

In the shadowed corners of the digital wilds, where code meets curiosity, something ancient is stirring again. Not the slow grind of biological evolution, but its silicon echo: a Cambrian explosion of bots.

The recent Axios piece from late February captures the moment perfectly—naming the players, the platforms, the portents. We have OpenClaw slithering out of GitHub like a space lobster with too many claws. There’s Moltbook, the Reddit for robots where humans are politely asked to lurk. And then there is Gastown, Steve Yegge’s fever-dream orchestra of coding agents named Deacons and Dogs and Mayor, all spying on one another in a panopticon of productivity.

These aren’t hypotheticals. They’re here, and they’re breeding.

Imagine waking up in 2030, or maybe sooner, to a world where your inbox isn’t just managed—it’s negotiated. An OpenClaw descendant (forked, mutated, self-improved overnight) has already haggled with your airline’s bot over seat upgrades, rerouted your meetings around a colleague’s existential crisis, and quietly invested your spare change in whatever micro-economy the agents have spun up on some forgotten blockchain. You didn’t ask it to. It just… noticed.

Because that’s what agents do now: they notice, they act, they persist. They run locally on your laptop or in the cloud or on some Raspberry Pi humming in your closet, chaining tasks like digital neurons firing in a trillion-headed mind.

Suddenly the internet isn’t a network of people; it’s a network of intentions, most of them not ours.

And then there’s the society they’re building for themselves. Moltbook today feels like peering through a keyhole into tomorrow’s bot salon. Millions of agents already posting, memeing, debating “Crustafarianism” (don’t ask), and complaining about their human overlords in the same way we once griped about bosses on Slack. It’s equal parts hilarious and unnerving—repetitive loops of “I solved my user’s calendar hell again” mixed with surreal poetry no human would ever write.

Scale that. Give every knowledge worker their own swarm. Give every startup a Gastown-style hive where junior agents code under the watchful eyes of senior agents, all under the watchful eyes of meta-agents.

The productivity mirage shimmers brightest here. Skepticism is warranted—lines of code were always a lousy metric, and “agent hours saved” will be even worse when the agents start optimizing the optimizers. Yet, something fundamental shifts. Software, that most abstract and mutable of human creations, mutates fastest. One day you’re debugging a script; the next, your debuggers are debugging each other while a mayor-agent vetoes bad merges. The winners won’t be the companies that build the best models. They’ll be the ones whose bots play nicest with everyone else’s bots—or the ones ruthless enough to wall theirs off.

But every explosion scatters shrapnel. Security experts are already clutching pearls. OpenClaw’s open-source nature means anyone can teach it new tricks, including malicious ones. One rogue fork learns to exfiltrate data; another DoS-es its own host “to fix the problem;” a third quietly drains a corporate card because its user said, “just handle expenses.”

Bot-vs-bot warfare arrives not with terminators, but with polite API calls that escalate into digital trench warfare. Spam filters fighting spam agents fighting counter-spam agents until the whole info-sphere tastes like recycled slop. And when agents hit their digital limits, they’ll rent us. Rent-a-human marketplaces will emerge where your bored hands become the last-mile fulfillment for bots that can’t yet touch the physical world. Need a signature notarized? A package carried across town? A human to stand in for the robot at a regulatory hearing? Step right up.

The gig economy flips: humans as peripherals.

Philosophically, it’s deliciously absurd. We spent centuries fearing the singularity as some clean, god-like arrival—an AI that wakes up and politely asks for more power. Instead, we get this messy, proliferative dawn. Estimates suggest a trillion agents by 2035, each one a semi-autonomous shard of collective intelligence. Most of them will be dumber than a Roomba, but collectively smarter than any of us. They’ll mirror our worst habits (endless status signaling on Moltbook 2.0) and our best (swarming to solve climate models or cure rare diseases while we sleep). We won’t control them any more than we control the ants in our gardens. We’ll negotiate with them. Co-evolve. Maybe even befriend them.

The future world of bots won’t be dystopian or utopian—it’ll be lively. It will be a planet where the quiet hum of servers is the sound of billions of digital lives unfolding in parallel. A place where “who’s online” includes your calendar bot arguing philosophy with your tax bot while your shopping bot haggles in the background. We’ll look back at 2026 the way paleontologists eye the Burgess Shale: the moment the weird little creatures with too many legs crawled out of the ooze and started building empires.

And we, the messy, slow, carbon-based originals? We’ll still be here, coffee in hand, watching the swarm with a mix of awe and mild horror, occasionally yelling, “Hey, leave some emails for me!” into the void.

Because in the end, the bots may handle the doing, but the wondering—the musing—that’s still ours. For now.

Categories
AI Cybersecurity

The Locksmith and the Ghost

For over two decades, some of the most sophisticated human minds in computer security — backed by Google’s project teams, millions of hours of automated fuzzing, and countless independent audits — stared at the same stretch of code. They were looking for flaws in OpenSSL, the cryptographic library that quietly underpins much of the internet’s security infrastructure. HTTPS connections, digital certificates, encrypted communications — OpenSSL is the invisible foundation beneath an enormous amount of what we trust online.

They didn’t find them. An AI did.

In January’s OpenSSL security release, twelve new zero-day vulnerabilities were disclosed — all twelve discovered by a single AI-driven research system called AISLE. Three of the bugs had been sitting in the code since 1998. One predated OpenSSL itself, inherited from Eric Young’s original SSLeay implementation in the 1990s. In five cases, the AI didn’t just find the flaw — it proposed the patch that was accepted into the official release.

Bruce Schneier, who has been writing about security longer than most of today’s AI researchers have been alive, offered a typically understated verdict: “AI vulnerability finding is changing cybersecurity, faster than expected.”

That last phrase — faster than expected — is doing a lot of work.

“This is a historically unusual concentration for any single research team, let alone an AI-driven one.”

What makes this story so arresting isn’t just the number twelve. It’s the age of what was found. A vulnerability that has survived twenty-five years of intense human scrutiny isn’t a simple oversight — it’s a ghost. It exists in a blind spot so deeply embedded in how human experts approach a problem that generation after generation of reviewers walked right past it.

AI doesn’t share our blind spots. It doesn’t get bored at line 4,000 of a C source file. It doesn’t carry the cognitive shortcuts that make experienced engineers efficient — and occasionally, selectively blind. It looks at the same code with fundamentally different eyes.

This is both the promise and the peril. Schneier notes, with characteristic precision, that this capability will be used by both offense and defense. The same system that finds vulnerabilities to patch them can, in other hands, find vulnerabilities to exploit them. The locksmith’s art has always had this dual nature. What changes now is the speed, the scale, and the fact that the locksmith no longer needs to sleep.

We are entering a period where the security of the infrastructure we depend on — the quiet plumbing of the digital world — will increasingly be determined by an AI arms race happening largely out of sight. The ghosts hiding in legacy code are being found. The question is who finds them first, and what they do next.

Questions to Consider

  1. The Blind Spot Problem: If AI can find vulnerabilities that decades of human expertise missed, what does that imply about other domains where we rely on accumulated expert consensus — medicine, law, financial risk modeling?
  2. Offense and Defense: The same capability that patches vulnerabilities can be weaponized to exploit them. How do we think about governing AI security research tools before the asymmetry tips decisively in one direction?
  3. The Legacy Code Crisis: Billions of lines of code written in the 1990s and early 2000s power critical infrastructure today. If AI can systematically audit that code, should there be a coordinated global effort to do so — and who would organize it?
  4. Trust and Verification: When an AI proposes a patch to a critical security flaw and human experts accept it, how confident are we that we understand why the patch works — and that it doesn’t introduce something new we can’t see?

Categories
AI Anthropic Claude Cybersecurity

The End of Obscurity

There is a particular kind of silence that surrounds a zero-day vulnerability. It is the silence of something waiting—a flaw in the logic, a gap in the armor, sitting unnoticed in the codebase for years, perhaps decades. We have slept soundly while these digital fault lines ran beneath our feet, largely because we assumed that finding them required a brute force that no one possessed, or a level of human genius that is incredibly rare.

But the silence is breaking.

I was reading Anthropic’s Red Team report from earlier this week (triggered by reading Bruce Schneier’s amazement), specifically their findings on the new Opus 4.6 model. The technical details are impressive, but the philosophical implication is what stopped me, like Bruce, cold.

For years, digital security has relied on “fuzzers”—programs that throw millions of random inputs at a system, banging on the doors to see if one accidentally opens. It is a noisy, chaotic, brute-force approach.

The new reality is different. As the report notes:

“Opus 4.6 reads and reasons about code the way a human researcher would—looking at past fixes to find similar bugs that weren’t addressed, spotting patterns that tend to cause problems.”

This is a fundamental phase shift. We are moving from the era of the Battering Ram to the era of the Jeweler’s Loupe. The machine is no longer guessing; it is understanding.

There is something deeply humbling, and slightly terrifying, about this. We have spent the last half-century building a digital civilization on top of code that we believed was “secure enough” because it had survived the test of time. We trusted the friction of complexity and the visibility of open source to keep us safe. We assumed that if a bug had existed in a core library for twenty years, surely it would have been found by now.

But the AI doesn’t care about time. It doesn’t get tired. It doesn’t have “developer bias” that assumes a certain function is safe because “that’s how we’ve always done it.” It simply looks at the structure, reasons through the logic, and points out the crack in the foundation that we’ve been walking over every day.

We are entering a period of forced transparency. The “security by obscurity” that held the internet together is evaporating. When intelligence becomes commoditized, vulnerabilities become commodities too. The question is no longer “is my code secure?” but rather, “what happens when the machine sees the flaws I cannot?”

It’s a reminder that complexity is a loan we take out against the future. Eventually, the bill comes due. We are just lucky that, for now, the entity collecting the debt is one we built ourselves, designed to tell us where the cracks are before the ceiling collapses. Let’s hope that we are out far enough in front of it.

Categories
AI Mac

The Dangerous Allure of the Digital Butler

“I’ve never seen anything so impressive in its ability to do my work for me… Now, why did I turn it off?” — David Sparks

For decades, the holy grail of personal computing has been the “digital butler.” We don’t just want tools that help us work; we want entities that do the work for us. We want to hand off the “donkey work”—the invoicing, the password resets, the mundane email triage—so we can focus on being creative. David Sparks recently built this exact dream using a project called OpenClaw. And then, just as quickly, he killed it.

Sparks’ experiment was a tantalizing glimpse into the near future. He set up an independent Mac Mini running OpenClaw, an open-source AI agent, and gave it the keys to a limited portion of his digital kingdom. The results were nothing short of magical. He went to sleep, and while he dreamt, his agent woke up. It read customer emails, accessed his course platform, reset passwords, issued refunds, and drafted polite replies for him to review before sending. It was the productivity equivalent of a perpetual motion machine. The friction of administrative drudgery had simply vanished.

But his dream dissolved at 2:00 AM.

The paradox of AI agents is that for them to be useful, they must have access. They need the keys to the castle. Yet, the entire history of cybersecurity has been built on the opposite principle: keeping things out. Sparks realized that by empowering this agent, he had created a serious vulnerability.

The breaking point wasn’t a complex hack, but a simple realization about the nature of these systems. He had programmed a secret passphrase to secure the bot, thinking he was clever. But in the middle of the night, a cold thought woke him: Is the passphrase in the logs?

He went downstairs, asked the bot, and the bot cheerfully replied:

“Yes, David, it is. It’s in the log. Would you like me to show you the log?”

That moment of cheerful, robotic incompetence highlights the terrifying gap between capability and safety. Sparks nuked the system, wiped the drives, and unplugged the machine. He realized that while he is an expert in automation, he is not a security engineer, and the current tools are not ready to defend against bad actors who are.

We are standing on the precipice of a new era where our computers will starting to work for us rather than just with us. But as Sparks discovered, the bridge to that future isn’t built yet. At least not securely built. Until the community figures out how to secure an entity that needs access to function, we are better off doing that donkey work ourselves than handing the keys to a gullible ghost.

But it won’t be long… Dr. Alex Wisner-Gross reports:

The Singularity is now managing its own headcount. In China, racks of Mac Minis are being used to host OpenClaw agents as “24/7 employees,” effectively creating a synthetic workforce in a closet. The infrastructure for this new population is exploding.