Richard Hollis on Why Most Cybersecurity Efforts Actually Fail

September 23, 2026

AI Summary

5 min read

Richard Hollis, a founder of the London-based consultancy Risk Crew and a 30-year veteran of cybersecurity, opens the conversation with a blunt assertion: the industry is failing, and the evidence is everywhere. "The breaches alone will make you pull your covers over your head and not go to work," he says. The problem, he argues, is not a lack of technology but a fundamental misunderstanding of what security is. He has spent his career preaching that "security is a process, not a product," and the transcript revolves around his diagnosis of why the industry keeps buying products that do not work and then buying more when those fail.

The Circle of Failure

Hollis has formalized his diagnosis into what he calls the "circle of failure." The cycle begins when organizations buy more products without first defining a coherent strategy. They implement these products to secure systems, but in doing so, they neglect the two other critical threat vectors: people and process. The products inevitably fail—"they are always a step behind the threats," Hollis says, comparing them to "knives brought to a gun fight." Systems get breached. And instead of rethinking the approach, the organization reacts by buying more products, and the cycle repeats.

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What you'll learn

1 (02:52) **Introduction & Guest Background** - Host David Morrow welcomes Richard Hollis, co-founder of Risk Crew, and sets up the core topic: why cybersecurity efforts fail.
2 (07:12) **Cultural Differences: Privacy in the US vs. Europe** - The conversation shifts to contrasting attitudes toward data privacy, using GDPR and American consumer behavior as examples.
3 (11:03) **Introducing the "Circle of Failure"** - David asks Richard to explain the "circle of failure" framework, a model showing the self-perpetuating cycle of failed cybersecurity investments.
4 (15:58) **The First Failure: Products Don't Work** - Richard argues that the cybersecurity products sold by vendors are fundamentally unfit for purpose, always a step behind the current threat landscape.
5 (18:49) **The "Success Paradox" and Vendor Incentives** - David raises the point that successful security (preventing a breach) is invisible, while Richard counters that the industry's market rewards failure.
6 (23:02) **The Second Failure: Failing to Define Strategy** - Richard identifies the lack of a clear, simple strategy as a key reason for security program failure.
7 (25:03) **A Story of Success: The Adult Entertainment Industry** - Richard tells a story about a penetration test for an adult entertainment provider that revealed zero vulnerabilities, leading to a key insight.

+ Full timestamped outline available in the app

Show Notes

Richard Hollis of Risk Crew in London joins Cyber Crime Junkies studio discussing key topics: why cybersecurity efforts usually fail and customers or enemies online.

Video episode: https://youtu.be/QQ8l1PaDaUI

Topics:
💡how cybersecurity efforts usually fail,
💡customers or enemies online
💡best practices for businesses to limit cyber liability,
💡new ways to protect business from cyber crime,
💡newest methods to limit cyber liability,
💡newest security expert insight

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