What a Conversation About Headphone Amps Taught Me About AI Posted by Chris Roberts, Sid, AND Claude So, this is going to take a slight detour….bear with me, there's a point. A few weeks back I had a long conversation with Google's Gemini AI about
A practical guide for security leaders who are done waiting for permission to engage with the above question. Context: Frontier models, the current generation of large language models and multimodal AI systems from Anthropic, OpenAI, Google, Meta, Mistral, and others, have crossed a threshold in 2025-2026 that makes the
We arrive at the topic that organizations most commonly skip until something goes very wrong. Application security and software supply chain risk sit at the intersection of development, operations, and security, and that intersection is where some of the largest, most consequential breaches of the last decade originated. Context: Three
Cyber insurance used to be a straightforward purchase. Pay a premium, describe your controls, collect if you're breached. The market has matured painfully and significantly since then, mostly because of repeated, expensive losses that forced insurers to get serious about what they're actually covering. Context: The
Topic 11 covered how to buy vCISO and managed security services. This topic covers what happens after you buy, because that's where most programs quietly fail. Context: The security services market has a dirty secret: the relationship that gets sold is almost never the relationship that gets delivered.
Supply chain compromise has gone from an edge case to one of the dominant attack vectors of the last five years. Yet most TPRM programs are still built around the same questionnaire-and-spreadsheet model that existed before SolarWinds. Let's fix that framing. Context: Third-Party Risk Management
This is the topic nobody wants to spend money on, until they desperately need it. And then they wish they'd spent a lot more. Context: Backup and recovery used to be an IT operations concern. Ransomware made it a security-critical, board-level conversation. The question is no
Let's tackle the most over-marketed, least-understood architecture shift in modern security, and the one where vendor salesmanship has done the most damage to actual outcomes. Context: A few definitions worth pinning down before the sales pitch arrives: * Zero Trust, a philosophy and architecture principle, not a
Context: Threat intelligence (TI, CTI) is one of the most misunderstood and misused disciplines in security. The term has been stretched, diluted, and rebranded so thoroughly that "threat intelligence" today can mean anything from: * A feed of IOCs (IPs, hashes, domains), often stale by the time you see
GRC is exactly where this all things we’re talking about ties together (or doesn't, which is the real problem). It's also one of the most over-promised and under-delivered categories in security, because vendors have spent the last 5 years rebranding spreadsheets-with-workflow
Onward. This is a topic where the market has exploded in the last few years, every consultant with a CISSP now offers "vCISO services," and every MSP has rebranded as "MSSP." Quality varies wildly, and buyers often can't tell the difference between strategic security
Onward to a topic where vendor quality varies enormously and the buyer often can't tell the difference between elite and mediocre work, which is exactly how mediocre vendors stay in business. Context: This is one of the most opaque categories in security purchasing. You're buying a
We’re going to consolidate the two email-related bullets into one comprehensive deep-dive, because the questions you'd ask vendors and the questions you'd ask yourself about getting email security right are deeply intertwined. This will be one of the longer topics on the list
Let's tackle the next one, which is a bit different in shape because it's not really a "vendor question" topic, it's an architectural decision framework. So I'm going to adapt the format slightly: questions you should ask yourself, your team,
Onwards to a category that has exploded in acronyms and vendor consolidation faster than anyone can keep up. Cloud security is genuinely complex, but vendors have made it sound more complex than it needs to be, in order to sell you platforms. Context: Let me decode the alphabet soup first,
Identity is arguably the most important topic on this list, because identity is the new perimeter, and most breaches in the last five years have involved compromised credentials, over-privileged accounts, or identity infrastructure that was poorly understood, let alone defended. Context: * IAM (Identity & Access Management), the system of
This is a category that's quietly becoming one of the most fragmented and confusing in security, because every vendor in adjacent spaces (CSPM, EDR, penetration testing, threat intel) has shipped some kind of "attack surface" feature and now claims to do VM/ASM/EASM. Let'
Onward to a topic where the marketing has gotten especially aggressive lately: the "autonomous SOC" and the army of vendors promising to replace your analysts with bots. Context: This is a hot, messy category. You'll hear pitches like "autonomous SOC," "AI SOC analyst,
SIEM has been "dying" for a decade and yet somehow keeps getting more expensive. SOAR was supposed to fix the analyst shortage and mostly didn't. Log management is where most organizations actually live but rarely budget honestly for. Let's untangle it. Context: SIEM (Security
This space is mature, crowded, and genuinely confusing because vendors have blurred the lines between EDR, XDR, and MDR to the point where the acronyms are nearly meaningless in marketing materials. Let's fix that. Context: EDR (Endpoint Detection & Response) protects endpoints. XDR (Extended Detection & Response) promises
Let's kick this off with the topic that's causing the most vendor-induced headaches in 2026. Context: Every vendor now claims to be "AI-powered." Most aren't, in any meaningful sense. Some bolted a GPT wrapper onto their UI last quarter. Others
Sid, Claude, and I were talking: We work in a cybersecurity industry that is filled with over-promises and under-delivery. Being a CISO, CTO, or leader working inside a "regular" company, whether that's healthcare, manufacturing, finance, or simply a local business that doesn't
There’s things in life that I’ve come to learn need to be held to either the three strikes, or fail fast rule. Be it cars, technology, people, places, or jobs. It’s not perfect, but it is something I know at the back of my mind I often
Once upon a LONG time ago, someone once said in a now infamous video “war, what is it good for? Absolutely nothing!” That observation has merit, but it’s unfortunately not accurate. The “War Machine” is a vast array of companies, consulting agencies, sycophants, and others all profiting from the