The back half of the episode digs into what actually makes someone a hard target in 2026. Matteo breaks down why breach data tends to be higher-fidelity than data broker information, since people aren't expecting it to be exposed, and walks through how exposure isn't just what an executive posts, it's what their kids, their assistant, or their family puts online too. He and Chris trade notes on the practical playbook: understand your exposure, remove what can be removed, accept what can't, and build in mitigation and disinformation strategies for the rest. The thread that ties it together: nobody gets to zero risk, but understanding your exposure and working it down deliberately is what separates a hard target from an easy one.

Ryan walks through his unconventional career path; from an early military commission, to a security job at Disney that led him into counter-surveillance and insider threat investigations, to building cyber threat intelligence from the ground up at Levi Strauss & Co., to landing at Black Rifle and constructing a converged security function from little more than a one-page DHS concept. Four years later, that program spans physical security, cybersecurity, CTI, privacy, brand protection, crisis management, and safety a broader scope than most peer organizations, including within his own ISAC community.

The back half of the conversation turns to how AI is reshaping the threat landscape. Ryan argues that trying to track every adversary TTP is a losing strategy, since attackers increasingly outsource their tradecraft, and even their imagination, to AI tools. He makes the case that defenders are better served focusing on behavioral anomalies rather than chasing a moving target. Ben and Ryan also discuss the growing bridge between digital compromise and physical danger to individuals, from targeted CISOs to AI-enabled social engineering that's collapsed years of required skill into minutes of effort.

The group digs into why physical and cyber security teams still operate in silos at most companies, often due to old trust breakdowns, mismatched vocabulary, and reluctance to step outside one's lane, and what it actually takes to build shared training, tabletop exercises, and mutual respect between Cyber/CTI and Physical security teams Ryan closes with grounded career advice for anyone entering the field, plus one blunt personal security tip that has nothing to do with AI at all.

Season 2 opens with a shift: less about tools, more about the people doing the work. Ben Barrontine and new co-host Chris Wingfield sit down with Bryan Flannery, founder of Foresight Security and one of the oldest friends of the show.

Bryan left an 18-year pension two days after his 42nd birthday to build Foresight, now 55 employees across nine states. The three get into behavioral threat assessment, the difference between people who build and people who run what is already built, and the real weight of leadership. Why being a founder is the loneliest job Bryan has ever had. The provider hat versus the recipient hat, and why the founder only wears one. Why a mentor beats a school and why communication is the highest-leverage skill a leader has.

Grit and resilience get you in the door. People keep you standing.

Guest: Bryan Flannery, Founder, Foresight Security Consulting https://foresight-sc.com/
Hosts: Ben Barrontine and Chris Wingfield, 360 Privacy

New episodes of Hard Target drop every other week. We are going behind the scenes with the men and women actually making things happen.