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Best Security, Business, and Technology Books of 2016

Dozens of times per year, I get asked to recommend my favorite books so I couldn’t say no when the OODA Loop team asked me to build on Mark Mateski’s popular Red Teaming book list by providing my top 10 books for 2016. I have very eclectic interests, so I’ve focused my list on the top security, business, and technology books of 2016. Given that I’ve always drawn on fiction for both inspiration and insight, the list also includes three very compelling works of fiction that should be of interest to those in the security and technology fields. Please feel free to share your thoughts and recommendations with me via twitter @MattDevost. Happy reading!


The Seventh Sense: Power, Fortune, and Survival in the Age of Networks by Joshua Cooper Ramo
I first met Joshua several years ago during a reception for a private event we were both speaking at and I was impressed with his insights. In fact, I adopted a quote he mentioned for use in some of my presentations that has been incredibly well received. The Seventh Sense earns the award for the most highlighted book in my 2016 collection and is chock full of many wonderful insights. Joshua Cooper Ramo argues that the future of business and society will reward those who have a Seventh Sense for understanding how things are connected or will be connected in the future. Those who understand how things are or will be connected will garner a great advantage over those who don’t and many will attempt to exert power by controlling the connections (a la the Chinese Firewall).


Black Box Thinking: Why Most People Never Learn from Their Mistakes – But Some Do by Matthew Syed
As a red teamer and entrepreneur I’ve always made a habit of studying success and failure with equal weighting. We received a lot of criticism during the Terrorism Research Center days for tracking failed terrorist attacks in our database, but we truly believed they were a roadmap for future intent and innovation. Black Box Thinking is specifically focused on understanding how organizations learn from their mistakes (or don’t) and draws a stark contrast between failure in the commercial aviation and medical industries. I recently recommended this book to an executive only to find that they later made it required reading for the entire management team.


Shoe Dog by Phil Knight
The grittiest and most honest book about entrepreneurship that I have ever read. Phil Knight, the founder of Nike, provides a multi-decade history of his quest to launch his own shoe company and the blood, sweat, and tears it took to get there. His writing style is engaging and the history of Nike is absolutely compelling and inspirational. This book has earned a spot in my top ten business books of all time.


Dark Territory: The Secret History of Cyber War by Fred Kaplan
Fred Kaplan is a Pulitzer Prize-winning journalist that decided to focus his attention on documenting the secret history of cyber war and spent years conducting research and interviewing an impressive list of experts. The thorough nature of his research and his ability to capture and highlight the themes and events that impacted three decades of cyber conflict and information warfare make this an essential history of the topic. Whether you were on the front lines of DoD Directive 3600.01 or new to the field, you will gain substantial insights from this book.


Eccentric Orbits: The Iridium Story by John Bloom
Prior to SpaceX, Facebook, and Google popularizing the concept of global satellite communications there was Iridium. This book provides a well documented history of the formation of Iridium and the business, political, and financial challenges that nearly resulted in the complete failure of the company numerous times. It provides great insight into why innovation is hard in large companies and the risks associated with space operations.


Playing to the Edge by Michael Hayden
General Michael Hayden is the only person to have served as both the Director of the Central Intelligence Agency and the National Security Agency. He was the head of the NSA on September 11, 2001 and spearheaded the agency’s controversial approach to intelligence collection which has garnered much attention in the press in recent years. General Hayden provides critical insight into the formation of those programs that can only be provider by an insider that lived through it. He provides similar insights into his tenure at CIA and the challenges of combatting global terrorism. Whether you support or criticize the policy, organizational, and technical approaches to intelligence over the past 15 years, you would be well served to read this first person, behind the curtain perspective on modern security challenges.


Rise of the Machines: A Cybernetic History by Thomas Rid
What do Cypherpunks and Assassination Politics have to do with the history of Cyber Conflict? Thomas Rid provides the reader with an slightly different perspective on our cybernetic history delving into the fringe elements and ideas that are not widely examined but were hugely impactful to a generation of security experts. Given my own interest, study, and participation in the topics examined, I found this to be a great alternative or counterculture approach to documenting an essential topic.


Dark Matter by Blake Crouch
The first of three fiction books on this list, Dark Matter is a mind-bending near-term science fiction thriller that explores a multi-verse paradox exposed by a scientific achievement. To provide more detail would ruin the story, but this book is a hell of a fun ride.


Ghost Fleet: A Novel of the Next World War by P.W. Singer and August Cole
What does war of the future look like? To date, few have provided a more compelling or technically accurate approach to the topic. Set in the not-to-distant future in which our dependence on technology has only increased, Singer and Cole weave a tale of international conflict in which cyber attacks are a key enabler of the outcome.


The Cartel by Don Winslow
Despite this being a work of fiction, Winslow provides what is perhaps the most accurate documentation of organized crime in Mexico. Weaving in real-life events with fictional characters, the Cartel does not shy away from gritty brutality, political realities, and the law enforcement challenges in countering what John Sullivan has described as a Criminal Insurgency.

Matt Devost

Matt Devost

Matthew G. Devost is the CEO & Co-Founder of OODA LLC. Matt is a technologist, entrepreneur, and international security expert specializing in counterterrorism, critical infrastructure protection, intelligence, risk management and cyber-security issues. Matt co-founded the cyber security consultancy FusionX from 2010-2017. Matt was President & CEO of the Terrorism Research Center/Total Intel from 1996-2009. For a full bio, please see