John Dwyer of Coalfire

Show Notes

Cybercrime is no longer just a big-company problem. If you own a business, manage a team, or handle money, John Dwyer, Vice President of Cloud and AI Security Services at Coalfire, says you are already in the blast radius. The scams are getting faster, smarter, and cheaper to run.

In this episode, Chris and John discuss what small and mid-sized businesses actually need to worry about right now. From deepfake payment fraud and business email compromise to ransomware, typosquatting, and AI-driven scams, this episode cuts through the fear and gets specific about what really matters. You’ll discover:

• Why most cyberattacks are still built on the same old playbook, just executed faster
• How AI is lowering the barrier for criminals and making fraud more convincing than ever
• Why emotional urgency is the biggest vulnerability in both humans and businesses
• The simple, low-cost protections that can dramatically reduce your risk
• How to think about cyber insurance, endpoint protection, MSPs, and tabletop planning

John also breaks down the four major buckets of cybercrime: fraud, data theft, operational disruption, and resource hijacking. He explains why most small businesses only need to focus on two of them to cover the highest-risk scenarios. He shares real-world stories of companies getting hit by invoice fraud, fake hiring scams, and sophisticated impersonation schemes that look absurd on paper but still work in the real world.

If you’ve ever wondered whether your business is actually prepared for a scam, a breach, or a ransomware event, this episode will help you think about risk before the worst day arrives. It’s especially valuable for founders, operators, sales and marketing teams, and anyone experimenting with AI inside the business. Listen now!

Episode Chapters

00:00 Introduction of John Dwyer

04:58 Navigating AI in Business Security

12:10 Understanding Cyber Threats and Scams

20:03 Real-Life Cybersecurity Incidents

32:35 The Role of AI in Cybersecurity

51:14 Best Practices for Small Businesses

01:00:08 Engaging with Managed Security Providers

01:27:53 Conclusion and Future Considerations

Learn More About John

Connect with John on LinkedIn.

Learn more about Coalfire.

Get a copy of Shannon's book, It's About Time.

Learn More About Chris

Connect with Chris on LinkedIn.

Learn more about Vendilli.

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