Cyber Risk Articles and Insights

Cyber Risk for Business Leaders

Bite Size Security is a short-form article series focused on how cyber risk affects business decisions, operations, insurance, and value. Each piece delivers concise, business-first perspective for CEOs, CFOs, and executives who want clarity without technical detail.

Latest Updates

This Is the Cyber Risk Article CEOs Actually Send Each Other

December 5, 2025

10 steps CEOs can take to manage cyber risks and protect their business—because ignoring them could make you the next cautionary tale.

Cyber Risk Is Now a Valuation Metric: Are You Prepared?

November 23, 2025

A guide for the coming wave of exits & acquisitions: Over the next 5 to 10 years the market will see the largest shift in business ownership.

Prepare Now or Be Left Behind: Why Cyber Risk Is the Next Financial Due Diligence

October 31, 2025

The truth is, cyber risk is still the biggest blind spot in business today. It’s not a tech problem. It’s a business and financial risk.

The $500,000 Wake-Up Call Every CEO Should Hear

October 19, 2025

This isn't just an insurance story. The insurer paid. Then it sued. The uncomfortable truth: your cybersecurity isn't just about prevention.

The Cybersecurity Spending Trap: Why Most Companies Are Funding Failure

October 17, 2025

Most executives think they’re doing enough because there’s a line item in the IT budget. Cybersecurity isn’t a purchase. It’s a discipline.

Cybersecurity Awareness: More Than Just Pumpkin Spice Season

October 3, 2025

Every October rolls in with two things: Cybersecurity Awareness Month & pumpkin spice. One makes you feel warm & cozy. The other can burn you.

The Deal Team’s Blind Spot: Cyber Risk in Value Creation

September 12, 2025

Why cyber risk deserves a seat at the CEO's table & how private equity buyers overlook this critical issue, risking costly consequences.

The CEO’s Missing Advisor: Cyber Risk at the Table

September 5, 2025

Cyber is now the number-one business risk, but most CEOs still do not have a Cyber Risk Advisor in their inner circle.

Cyber Insurance in 2025: What the Data Says About Managing Cyber Risk

August 29, 2025

Cyber insurance tops the worry list for businesses everywhere due to the rapidly changing landscape. Let's explore how to check coverage.

Selling Your Business? Don’t Let Cyber Risk Turn Your Golden Goose into a Wreck

July 18, 2025

If you're planning to sell your business or acquire one a hard truth: Cyber risk can derail the entire deal. Learn best practices & more.

Beyond the Firewall: A Frank Conversation About Cyber Risk in 2025

July 4, 2025

Cyber risk in 2025 isn’t just about technology. It’s about people, process & blind spots & the “good enough” practices that aren't challenged.

Not the Newsletter I Planned to Write…But One Every Leader Should Read

June 26, 2025

Some mornings, you wake up to an ordinary to-do list & other mornings, to the news that 16 billion usernames and passwords have been leaked.

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