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Top 10 Security, Technology, and Business Books of 2019

There are two key thematics to this year’s top 10 security, technology, and business books of the year; cyber and AI. It definitely feels like there has been a sea change in cyber this year with the threat on the precipice of being full realized as risk to critical infrastructure. Where cyber is the issue we are dealing with now, AI is now fully emerged as the issue we will be dealing with in the next decade. As a result, I read a lot of books on each topic this year and reducing them into a top 10 list was difficult.

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Here is the 2019 list:

Cult of the Dead Cow: How the Original Hacking Supergroup Might Just Save the World by Joseph Menn

Joe Menn does a great job capturing a critical time in hacker history with the emergence of the cDc and the influence the group would have on security, policy, and technology issues over a period of several decades. A great story and very well written and filled with optimism for how hackers will solve some of societies greatest problems in the future. That messaging hits close to home for me and echoes my calls for a Generation Hack so I’m awarding this book my top pick of the year.

Sandworm: A New Era of Cyberwar and the Hunt for the Kremlin’s Most Dangerous Hackers by Andy Greenberg

Sandworm captures recent cyberwar history by tracking the attacks against critical infrastructure including the power grid. It is quite daunting to see all of these case studies stacked together in one articulate narrative tale and brings the realization that cyber conflict is here and attacks against critical infrastructure are inevitable. There is some great storytelling here as well and an interesting cast of characters (on the defender’s side!) that are good friends.

AI Superpowers: China, Silicon Valley, and the New World Order by Kai-Fu Lee

The most important book on artificial intelligence written in 2019, AI Superpowers reminded me of reading “Unrestricted Warfare” in 1999. It provides great insight into the state of AI in the U.S. and China and how AI is shaping up to be the most disruptive and important technology of the next century.

The Man Who Solved the Market: How Jim Simons Launched the Quant Revolution by Gregory Zuckerman

A great look at the quant revolution in finance told through the story of the most successful hedge fund in history. Not only is this a compelling story, but it is an interesting case study in building eclectic teams and managing STEM personalities over multiple decades.

Tools and Weapons: The Promise and the Peril of the Digital Age by Brad Smith and Carol Ann Browne

Captures the essence of cyber and privacy issues from an insider who was in the room during many critical moments and crises. Smith selects a great series of events to focus in on that manage to touch a broad spectrum of past, present, and future concerns.

Billion Dollar Whale: The Man Who Fooled Wall Street, Hollywood, and the World by Tom Wright and Bradley Hope

An amazing story of large scale and unprecedented fraud involving sovereign funds, governments, Hollywood, and a host of other international organizations, destinations, and personalities. Reads like a great caper novel, but is entirely true. Will go down as one of the greatest social engineering scams in history.

Hunting LeRoux: The Inside Story of the DEA Takedown of a Criminal Genius and His Empire by Elaine Shannon

Fascinating look at a hacker who branched into traditional organized crime to include guns, drugs, and other illicit industries. Fascinating manhunt story involving a host of interesting characters, circumstances, and (given the hacker background) a technology enabled critical infrastructure.

For another great and more detailed read on this same subject, check out:


The Big Nine: How the Tech Titans and Their Thinking Machines Could Warp Humanity by Amy Webb

Another insightful book on the way companies in the U.S. and China are shaping and competing for the future of AI and other advanced and disruptive technologies. Provides the best baseline on big commercial AI you can find.

The Perfect Predator: A Scientist’s Race to Save Her Husband from a Deadly Superbug: A Memoir by Steffanie Strathdee and Thomas Patterson

This was my favorite non-domain non-fiction book I read this year (meaning it covered a subject for which I have no expertise) and tells the tale of a deadly antibiotic resistant bacteria that brought one man to the brink of death, and his wife’s Indiana Jones-like quest to save his life by researching a long-abandoned medical approach and the international team that just might get it to work in time Fascinating and impossible to put down.

Stealing Worlds by Karl Schroeder

My favorite science fiction book of 2019 blends together so many current and emerging technologies in such a realistic manner that it doesn’t feel like reading fiction. The predictions all seem plausible, and the world and characters are very well developed and compelling. A must read for 2019 and I’ve already put this one on my re-read list – a distinction that is shared with only a handful of books.

Honorable mentions:

The Fifth Domain by Richard Clarke and Rob Knake

Zone War by John Conroe

Delta-v by Daniel Suarez

The Infinite Game by Simon Sinek


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