In 2022, I sat in a meeting where three companies were pitching vCISO services to a consortium of 26 organizations. The question was simple: “Tell us how your vCISO services work.” The first company — a consulting firm from the east coast — answered: “Well, we sell you a block of hours, and as you need services performed, we deduct from your hours.” The second…
I ask almost every CISO (Chief Information Security Officer, for the non-security folks) I meet the same question. “Tell me what you do — but explain it like you’re talking to some random stranger walking down the street. Not to me.” Then I wait. More often than not, within 30 seconds, I stop them. “You’ve already lost me.” The look I get is hard to…
It was 2:00 in the morning. I had an information security assessment report due in a matter of hours. FRSecure was young — just a handful of employees — and I was routinely working 90-plus hour weeks. Not because I was lazy with my time. Because there was that much work to do. I wasn’t procrastinating. I just hadn’t had time to finish. Sitting there,…
We’ve got it backwards. The cybersecurity industry spends billions on tools, certifications, frameworks, and compliance programs. Companies hire armies of analysts. Vendors peddle the next “AI-powered” solution that’s going to save us all. And still — still — the breaches keep coming. The scams keep working. The ransomware keeps paying out. Why? Because we’ve been focused on the wrong things. We’ve made cybersecurity so complicated,…
How to Disagree Like an Adult — Part 5 (Final) This post is part of the How to Disagree Like an Adult series. If you missed earlier posts, start there. Not every conversation deserves your energy. That might sound like giving up. It’s not. It’s one of the most underrated skills in disagreement — and the one most people never develop. We’ve spent four posts…
The Skills Nobody Taught Us How to Disagree Like an Adult — Part 4 This post is part of the How to Disagree Like an Adult series. If you haven’t read the earlier posts, start there. This one builds on them. So far, I’ve written a lot about what’s broken. Why debate has collapsed. Why identity hijacks thinking. Why insults replace arguments. Now it’s time…
In my previous post, I made the claim that as long as Americans keep buying drugs, someone will keep supplying them. Mexico has not always been the primary supplier of drugs to American consumers. The supply has shifted repeatedly over time, tracking enforcement pressure, geopolitics, and—most importantly—where demand could be profitably met. This is one of the strongest pieces of evidence that the drug war…
And Mexico Keeps Getting Stuck With Ours WARNING: This post may trigger some people. If you are one of those people, my advice is to buy a mirror and use it. The drug war is not complicated. We pretend it is. We wrap it in politics, policy debates, border arguments, and moral posturing. But at its core, it’s a simple supply-and-demand problem. And the…
How to Disagree Like an Adult — Part 3 This post is part of the How to Disagree Like an Adult series. If you missed earlier posts, start here: 👉 Part 1 — When Debate Dies, Insults Take Over 👉 Part 2 — Ideas Aren’t Identities Most people think insults are strength. They’re not. Insults aren’t proof of righteousness. They’re the intellectual equivalent of raised…
I saw this post that said Amazon plans to replace 600,000 workers with robots. The response? “We’ve got to fight back.” Let me say something that might irritate both sides: You can’t fight back against technology. You never could. And you never will. History Doesn’t Care About Your Slogans We tried this before. We tried it with the printing press. We tried it with…