Chasing Entropy Podcast Episode 007: Allison Miller on Risk, Fraud & AI

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Jun 10, 2025

Allison Miller, a cybersecurity veteran and founder of Cartomancy Labs, shares her fascinating journey from childhood hacker to industry expert. She discusses how fraud reveals system weaknesses and emphasizes the importance of understanding payment and identity vulnerabilities. Allison also delves into the evolving role of AI in cybersecurity, highlighting its potential for detection and automation while addressing governance concerns. Her insights challenge organizations to enhance trust and security in a rapidly changing digital landscape.

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ANECDOTE

Early Cybersecurity Adventures

Allison Miller started her cybersecurity interest with communication networks and payphone hacks before the internet era.
Early online experiences, including IRC and seeing hijinks spill into the physical world, shaped her focus on how systems can break.

ANECDOTE

Selena Kyle Pseudonym Story

Allison used the handle Selena Kyle, Catwoman's alter ego, as a pseudonym on social platforms and DEF CON, blending her cyber and fraud interests.
Many people she met knew her only by this pseudonym, causing amusing identity confusions.

INSIGHT

Fraud Reveals System Weakness

Fraud fascinates Allison because it reveals how systems can be exploited even when working as intended.
Misbehavior targets the system's value points like communication in email and money movement in payments, exposing complexity and risk.

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In this insightful episode of Chasing Entropy, host Dave Lewis welcomes cybersecurity veteran Allison Miller to explore the intersections of fraud, risk, complexity, and AI in the ever-evolving digital landscape.

Allison brings two decades of experience spanning enterprise cybersecurity, anti-fraud, and advanced product risk. From traditional financial institutions to cloud-native startups, her work bridges how technology enables connection—and how those same systems can be exploited.

She shares her early fascination with communication networks, her journey through IRC, payphone hacks, and digital commerce, and how those formative experiences shaped her career.

Key Topics Covered

Chasing Risk and Complexity

Fraud as a window into system weaknesses — Allison explains why fraud fascinates her: it’s about understanding how things can go wrong even when the code is working as designed.
She discusses how payment systems, platform identity abuse, and communication channels become targets precisely where their value lies.

The Role of AI in Cybersecurity

AI as a detection tool: Building on her background in detection technologies, Allison sees AI as the next step in a lineage of data-driven defenses.
Three key AI applications:
→ Detection
→ Investigation assistance
→ Automation in Security Operations Centers (SOCs)
CISO responsibilities: While AI governance is still evolving, Allison highlights parallels with AppSec and suggests that product risk programs must incorporate AI security and safety.
Agentic AI and emerging risks: She warns that autonomous agents, while powerful, introduce new layers of system complexity that require holistic monitoring—simple components can combine into chaotic behaviors.

Future of Cybersecurity Leadership

Cloud, mobile, and multi-cloud continue to challenge traditional security models, requiring CISO teams to expand their skills and embrace innovation.
CISOs are now “chasing complexity” as much as they’re defending against it.

Advice for Aspiring Cybersecurity Professionals

Follow your curiosity rather than a linear career path.
Focus on interesting problems—your unique perspective will create opportunities.
Embrace networking and open conversations to accelerate learning and growth.

Quote of the Episode:
"Follow your curiosity. You can bring your interests into almost any job description—and that's where real opportunity lies." — Allison Miller

Tune in to this episode for a candid discussion that peels back the layers of how risk, fraud, and AI are shaping the cybersecurity front lines.

Subscribe to the Chasing Entropy Podcast for more real talk with the minds driving cybersecurity forward.

LinkedIn: Allison Miller, Founder & Principal, Cartomancy Labs

Website: Cartomancy Labs

Newsletter: Futurecast