Living Two Lives: Lessons from Undercover Cybercrime Operations

For years, people have asked me what it was really like living a double life.

Recently, I had the opportunity to join Aaron Stillwell on the APT & Cybersecurity podcast to discuss Operation Carder Kaos and some of the realities behind one of the most consequential undercover cybercrime investigations of my career.

We discussed much more than simply cybercrime.

We talked about operating overseas, adversarial tactics, social engineering, navigating internal politics, trust inside criminal ecosystems, and the psychological cost of living between identities.

One of the themes that emerged throughout the discussion was this:

Cybercriminals succeed because they understand people.

Technology changes. Tools evolve. AI accelerates attacks. But manipulation, trust, fear, greed, and human behavior remain constant.

Many people think undercover operations are primarily technical. The reality is they are deeply human. Success often depended less on technology and more on understanding how people think, how communities function, and how trust is built—or broken.

Those lessons remain just as relevant today.

Modern defenders are facing increasingly sophisticated threat actors that continue to blend technical capability with social engineering, psychological manipulation, and operational patience.

If you are interested in:

• The reality of undercover cybercrime operations
• How criminal ecosystems actually function
• Social engineering and adversarial behavior
• Leadership under pressure and decision-making in uncertain environments
• Lessons defenders can apply today

I encourage you to check out the discussion.

Podcast Link:

https://www.linkedin.com/events/operationcarderkaos7414058744440967168/theater/

Thank you to Aaron Stillwell and the APT & Cybersecurity community for the opportunity to have this conversation.

The threats may have evolved.

Human nature largely has not.