The Dark Web, AI Deepfakes, and the Business of Cybercrime Cybercrime has become global business, operating at scale across borders and industries.
In this episode of Bourbon & Bytes, host Terry McGraw, CEO of Cape Endeavors, is joined by Rebecca Taylor, Threat Intelligence Knowledge Manager and Researcher at Sophos, for an in-depth discussion on how the dark web, AI deepfakes, and human behavior are reshaping the modern cyber threat landscape.
The conversation explores how cybercrime has evolved into a mature underground economy, including ransomware-as-a-service, initial access brokers, credential marketplaces, and AI-enabled social engineering. Rebecca shares firsthand insights from human intelligence research on the dark web, revealing the community dynamics, anonymity, and moral gray areas that fuel cybercriminal activity.
They also examine how AI and deepfake technology are accelerating fraud, enabling real-time impersonation attacks, and lowering the barrier to entry for cybercrime—while defenders struggle to keep pace. The episode closes with a critical discussion on mentorship, diversity in cybersecurity, and why preventing young people from turning to cybercrime is becoming a national and global priority.
This episode is essential viewing for professionals in cybersecurity, threat intelligence, risk management, compliance, legal, IT leadership, and anyone seeking to understand where cyber threats are headed next.
*About Rebecca*
Rebecca Taylor is a Threat Intelligence Knowledge Manager and Researcher at @SophosCybersecurity, known for her work in dark web and human intelligence research. She is widely recognized for building cybersecurity communities—particularly supporting women in cyber—through initiatives such as Cyber Agony Aunts (https://cyberagonyaunts.co.uk/), mentoring, public speaking, and published work.
Rebecca has been acknowledged across the industry for her contributions, most recently winning Security Woman of the Year at the Computing Security Excellence Awards 2024. Her career journey from administrative roles into threat intelligence highlights the value of non-traditional backgrounds in cybersecurity, with a strong focus on making complex cyber threats understandable and building support systems for professionals across the industry.
*Chapters*
00:00 – Introduction to the Dark Web, AI, and Cybercrime
02:10 – Rebecca Taylor’s Path from Creative Writing to Cyber Threat Intelligence
05:05 – Why Non-Technical Backgrounds Matter in Cybersecurity
07:30 – Mentorship, Sponsorship, and Career Pivots in Cyber
11:45 – What Human Intelligence on the Dark Web Really Looks Like
14:30 – The Community Side of the Dark Web (and Why It’s Dangerous)
17:40 – Cybercrime as an Underground Economy
20:15 – Ransomware-as-a-Service and Initial Access Brokers
23:10 – How Threat Actors Navigate the Dark Web
26:45 – Moral Codes Inside Cybercrime Communities
29:40 – Encrypted Platforms, Telegram, and Mainstream Migration
33:20 – AI, Deepfakes, and the Next Wave of Cyber Fraud
37:00 – Why Young People Are Turning to Cybercrime
40:10 – Diversity, Mentorship, and Building the Cyber Workforce
44:15 – The Future of Cyber Threats and What Comes Next
47:10 – Final Thoughts on Resilience and Burnout in Cybersecurity
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#BourbonAndBytes #CapeEndeavors #Sophos