The Security Hippie Security, Audit and Leadership Series

In this review of The Security Hippie, Barak Engel's second book, the bottom line is simple: it is a narrative-driven primer for security leaders who learn best from real-world examples. The book is not a hands-on playbook but a collection of stories and leadership lessons drawn from Engel's career as the originator of the Virtual CISO concept and his time advising organizations such as Mulesoft, Stubhub and Amplitude Analytics. Readers seeking practical frameworks may find value in the context and judgement illustrated across cases rather than step-by-step checklists.

Key Features

• Leadership through story: Engel teaches security and audit concepts by sharing varied real situations, helping readers see how judgment decisions play out in organizations.
• Virtual CISO perspective: The author draws on experience as a fractional security chief to show how to advise multiple organizations and scale security thinking.
• Career-spanning anecdotes: The book includes episodes from notable companies, offering insight into common organizational patterns and pitfalls.
• Practical context over theory: Rather than prescribing rules, the narrative approach models how seasoned leaders evaluate risk and influence stakeholders.
• Follow-up to earlier work: As a successor to Why CISOs Fail, this book deepens the human and managerial side of security leadership for readers familiar with the topic.

Who It's For

The Security Hippie is best for current and aspiring security leaders, auditors, and senior IT managers who want to improve their judgment, communication and influence by learning from stories rather than checklists. Readers who benefit from case studies and reflective narrative will find the book useful for developing situational awareness and leadership instincts.

Those who want prescriptive templates, compliance matrices or technical how-to guidance should look elsewhere; this title focuses on organizational behavior, leadership and high-level security strategy rather than step-by-step operations or tool recommendations.

Pros & Cons

Pros

• Engel's experience as the originator of the Virtual CISO concept provides credible, high-level lessons for leaders.
• The storytelling format makes complex organizational dynamics accessible and memorable.
• Real-world examples from recognizable companies offer transferable insight into governance and risk conversations.

Cons

• The book emphasizes narrative and judgement and does not provide detailed technical instructions or checklists that some practitioners expect.

Specifications

Our Verdict

The Security Hippie is a worthwhile purchase for security leaders who prefer learning by example and want to sharpen their judgement and influence. It delivers practical value through stories from a seasoned Virtual CISO rather than prescriptive templates, making it good value for readers focused on leadership, organizational strategy and how to operate effectively at senior levels.

Frequently Asked Questions

Is this a technical handbook?
No. The book emphasizes narrative and leadership lessons rather than technical procedures or operational checklists.

Who wrote this book?
Barak Engel, known for originating the Virtual CISO concept and advising organizations such as Mulesoft and Stubhub.

Should I read the author's previous book first?
No requirement, but readers familiar with Why CISOs Fail will recognize themes and deeper context in this follow-up.