RESEARCH
Before You Sell Security, Ask Yourself This: Who’s Liable When It Fails?
Every MSP wants to talk about cybersecurity when things are going well. New tools, new programs, and a clean vCSO pitch that sounds great in a sales call and looks great in a slide deck. Dashboards, frameworks, and maturity models that promise progress and control. ...
Cyber Compliance
Stop Getting Mad When Your Client Won’t Buy Compliance
You know the look. You explain how they need MFA, a risk assessment, documented policies, backups that actually restore… and your client stares back at you like you just recited the GDPR in ancient Greek. You leave the meeting frustrated. ...
“Fined Without a Breach?” Why the Wojeski $60,000 Penalty Matters—even if You Think You’re Small
You’ve seen two kinds of headlines after cyber incidents: (1) lawsuits and (2) regulatory enforcement. The recent $60,000 fine against Wojeski ...
New California Audit Law Just Put Your MSP on the Hook. Here’s How to Turn It Into Recurring Revenue
If your clients process sensitive data, your MSP is now part of the legal conversation. On July 24, 2025, California finalized new rules that require businesses processing high-risk personal information to undergo annual, independent cybersecurity audits. This isn’t just for ...
Cyber Liability
AI Is Already Inside Your Walls. You Just Haven’t Looked Hard Enough.
Think your clients are the ones playing fast and loose with AI? Guess again. Your techs are doing it—right now—on your network. Not because they’re reckless. Because they’re efficient. They’re pasting configs into ChatGPT. Running SOPs through Gemini. Copying proposals ...
You’re Using Your Smartest Engineer Wrong (And So Are Your Clients)
What if I told you that you’re misusing the most powerful engineer on your team? No, not Josh. Not the guy with the beard who still thinks ZFS is the answer to everything. I’m talking about AI. And right now? ...
What a New Lawsuit Can Teach Us About Cyber Liability and Documentation
When a cyber insurance provider sues vendors after a ransomware incident, it’s not just about fault—it’s about proof. In Ace American Insurance Co. v. Congruity 360 and Trustwave, we see how courts allocate responsibility—and why the side with the best ...
Insurance & MSP Liability
You’re Not Insured. You’re Just Hopeful.
So there I am, wrapping up a conference session—over 1,000 MSPs in the building—and one guy comes up clutching a fresh copy of Standardized like it’s a fire extinguisher in a server room. He’s nodding along, clearly rattled in all ...
Your MSP Carries More Risk Than a Magazine Stand—and That’s a Problem
Let’s talk about airport gift shops for a minute. You know the ones—tiny kiosks with $14 neck pillows, expired jerky, and three copies of Men’s Health no one’s ever going to read. Now, tell me—how much sensitive data do you ...
If You Don’t Own the Security Stack, You’ll Be Replaced
There’s a quiet shift happening in the cyber insurance world—and if you’re not talking to your clients about it, someone else is. That someone is their insurance provider. And they’re not just selling policies anymore. They’re selling cybersecurity solutions too. ...
More Articles
Part 2: For the Price of Coffee, You Can Avoid Buying a Hacker a Yacht
Last time we looked at why tabletop exercises matter and how they can reveal the cracks MSPs don’t notice until it’s ...
Dropping the Bricks and Picking Up What Matters
Have you ever felt like you’re carrying around a ton of bricks? Not the sturdy, well-stacked kind either. I’m talking about the ones someone tossed into your backpack one by one until you’re hunched over, wondering why your knees suddenly ...
Part 1: For the Price of Coffee, You Can Avoid Buying a Hacker a Yacht
It always starts like a normal day. You grab coffee, drop your lunch in the fridge, skim through tickets and emails, maybe ...
If You Missed the Security Chaos of the ‘90s, You’re in Luck!
We’re all seeing it. AI is changing how we approach nearly every part of business. It’s taking meeting notes, spitting out action items, and building chatbots to handle the flood of internal questions. The potential benefits for busy teams and ...
Shadow IT Just Went Legal—and It's Coming for Your MRR
Earlier this year, a quiet courtroom in the Central District of California made noise the entire cybersecurity industry should be hearing: for the first time ever: a federal judge used the term “Shadow IT” in a legal ruling. And just ...
New State Cyber Rules Are Coming—Will You Be Ready, or Be the One They Blame?
California. New York. Massachusetts. One by one, states are turning up the heat on cybersecurity regulations—and if you're not preparing your clients for what’s coming, you're not just behind. You're exposed. Last week I blogged about upcoming California rules requiring ...
Vibe Hacking: The AI Nightmare Your Clients Aren’t Ready For
Do you have a plan to save your clients from the next big cybercrime wave? Because it’s already here. And it has a name: vibe hacking. Sounds harmless, right? Like something your marketing intern came up with after too much ...
Your Clients Are Already Breaking the AI Rules You Never Wrote
Let’s get real. Your clients are already using AI. They’re excited about how much more “effective” it makes them. Which means they’re doing the one thing you begged them not to do: Uploading PII? Happening. Copy-pasting sensitive client records into ...
The Portal Problem: Are You Still Driving a Horse and Buggy?
I was talking to an MSP the other day who said, “The portal’s slow. I can’t ever find what I need.” So I asked him, “When’s the last time you logged in?” His answer? A few months ago. Holy cow. ...
New California Audit Law Just Put Your MSP on the Hook. Here’s How to Turn It Into Recurring Revenue
If your clients process sensitive data, your MSP is now part of the legal conversation. On July 24, 2025, California finalized new rules that require businesses processing high-risk personal information to undergo annual, independent cybersecurity audits. This isn’t just for ...
Your Copilot Might Be Working for the Other Side
Let’s play a game. Imagine you hire a new assistant. Bright. Helpful. Always eager to please. You ask it to pull a report. It delivers. You ask it to summarize last quarter’s numbers. Done in seconds. Now imagine that same ...
The Dangerous Assumptions You’re Making
Your clients are making assumptions about you right now. They assume you’ve got their security handled. They assume you’re gathering the evidence. They assume you’ve already written their incident response plan. But here’s the problem: they’re wrong. I was on ...
