Cyber Risk Articles and Insights

They Got Breached Too.

May 1, 2026

What Mid-Market Sellers Don’t Understand About the Other Side of the Table I had dinner last month with a partner at a PE firm. Mid-market deals, mostly manufacturing and services.…

The Due Diligence Playbook You Used Six Months Ago May Already Be Outdated

April 23, 2026

Last week, the Cloud Security Alliance, SANS Institute, and OWASP published a joint strategy briefing called “The AI Vulnerability Storm.” The authors include some of the most respected names in…

The Day the Rules Changed

April 16, 2026

A few days ago, I called a friend. He is a CISO at one of the largest financial services enterprises in the country. Not someone who trades in drama. Twenty-plus…

You Already Turned Off the Alarm. You Just Don’t Know It Yet.

April 14, 2026

If someone walked into your building right now and said they were there to fix something, how long before anyone questioned them? Take a moment with that. Don’t answer it…

You Didn’t Get Hacked. You Got Fooled.

March 24, 2026

Most business owners think about cyber risk in a very specific way. Did someone break into our systems? Did we get hit with ransomware? Did something go down? That’s been…

Cyber Risk and Your Exit Number

March 9, 2026

Let’s start with a simple question that most owners never get asked. If a buyer’s diligence team walked in tomorrow and asked for proof that cyber risk is under control,…

The Vendor That Didn’t Lose the Contract

February 19, 2026

It Just Watched It Walk Out the Door The Renewal That Felt Routine A friend of mine runs a company with roughly 1,500 employees. It’s not fragile. It’s not experimental.…

The Week AI Agents Started Acting on Their Own

February 4, 2026

It is January 31, 2026. Most executives still think AI is a smarter search box. It is not. We just crossed a line where AI systems are starting to behave…

Comfortable Ignorance Protected by Process

January 29, 2026

Why Smart CEOs Lose Control of Cyber Risk Without Realizing It Happy New Year. It’s good to be back. As we head into 2026, I’ve been thinking a lot about…

Cyber Risk Is Now Part of How a Business Proves It’s Ready

January 29, 2026

For a long time, readiness was assumed. If you had a seasoned executive team, a trusted CISO, solid controls, and no major incidents, the business was considered prepared. Cybersecurity was…

If Cyber Can Move a Stock Price, It Can Move a Deal Price

December 15, 2025

A single breach can move a public company’s stock price. Yet in private deals, cyber is still treated like an IT task. Fill the gap.

Why Most Incident Response Plans Fail and What to Do Instead

December 12, 2025

If you want to know if a company is truly ready for a cyber incident, don't ask for the incident response plan. Ask a more direct question.

Cyber Risk Articles and Insights

Cyber Risk for Business Leaders

Latest Updates

They Got Breached Too.

The Due Diligence Playbook You Used Six Months Ago May Already Be Outdated

The Day the Rules Changed

You Already Turned Off the Alarm. You Just Don’t Know It Yet.

You Didn’t Get Hacked. You Got Fooled.

Cyber Risk and Your Exit Number

The Vendor That Didn’t Lose the Contract

The Week AI Agents Started Acting on Their Own

Comfortable Ignorance Protected by Process

Cyber Risk Is Now Part of How a Business Proves It’s Ready

If Cyber Can Move a Stock Price, It Can Move a Deal Price

Why Most Incident Response Plans Fail and What to Do Instead

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