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Top 10 Security, Technology, and Business Books of 2020

It was a challenging year for my booklist. Beyond just the 2020 pandemic issues, I had a hard time narrowing down on thematic for this year, so the list is even more eclectic than usual.  I’m still keenly interested in cryptocurrencies and blockchain technology, so I read several interesting books on Ethereum.  Pure business books had less appeal this year as it seemed that business was being disrupted on multiple levels, where fiction seemed even more appealing as I tore through William Gibsons Jackpot series amongst several others.

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Here is the 2020 list:

If Then: How the Simulmatics Corporation Invented the Future by Jill Lepore

This is a great story about the origins of early data science and predictive analytics. I had not heard of this company prior to reading the book, but it is clear they set the groundwork for an emerging field to include the work Cambridge Analytica conducted during the 2016 U.S. election

The Biggest Bluff: How I Learned to Pay Attention, Master Myself, and Win by Maria Konnikova
You might think this is a book about poker, but really it is a book about decision making with heavy applicability to entrepreneurs. Very insightful and I found myself highlighting quite a bit of material for future research and reflection.

The Gray Rhino: How to Recognize and Act on the Obvious Dangers We Ignore by Michele Wucker
There are infinite references to the black swan events of the world, but I had not heard of Gray Rhinos, which are meant to represent the obvious dangers or circumstances we chose to ignore or not act on and how we can build organizations that are more resilient to expected surprises.

The Infinite Machine: How an Army of Crypto-hackers Is Building the Next Internet with Ethereum by Camila Russo
I read several cryptocurrency books this year and this was my favorite. While I think Bitcoin will win the race with regards to store of value, Ethereum holds the most promise for programmable money and blockchain applications that will greatly impact the business world in the next five years.

As a runner-up, check out:

Out of the Ether: The Amazing Story of Ethereum and the $55 Million Heist that Almost Destroyed It All by Matthew Leising

Dark Mirror: Edward Snowden and the American Surveillance State by Barton Gellman
The best treatment of the Edward Snowden incident to date written by someone who was on the inside. Also, found it very insightful with regards to the journalistic process associated with running a story like this at the Washington Post.

Active Measures: The Secret History of Disinformation and Political Warfare by Thomas Rid
A bit academic, but a modern view of disinformation and political warfare that everyone needs to understand going into the next decade.

I’d strategically pair this book with Putin’s People: How the KGB Took Back Russia and Then Took On the West by Catherine Belton

The Hacker and the State: Cyber Attacks and the New Normal of Geopolitics by Ben Buchanan
The only cyber book on this list this year as it breaks some new ground in a very thorough and well written examination of cyber as a multi-dimensional national security issue.

T-Minus AI: Humanity’s Countdown to Artificial Intelligence and the New Pursuit of Global Power by Michael Kanaan
AI continues to be an important issue going forward and I’ve read a lot of books on the topic in the past five years. This year, I’m happy to recommend this one, which contrasts well with the China-centric books I recommended in previous years as it provides a good overview from the perspective of a U.S. military AI leader.

Attack Surface by Cory Doctorow
I’ve been a fan of Cory Doctorow’s for many years and used to assign his book Little Brother to my students at Georgetown. Attack Surface continues the story arch of Little Brother by focusing on Masha, the skilled hacker who found herself absorbed into the international security community on spooky world of surveillance private contractors. In my opinion, it is the best in the series and incredible poignant and insightful for today’s global surveillance and hacking environment. You don’t have to read the first two books to enjoy this one, though the entire series is compelling.

Alternatively, fiction fans should check out

Burn-In: A Novel of the Real Robotic Revolution by P. W. Singer & August Cole

The Plotters by Un-su Kim

I picked this book up in an effort to get further exposure to foreign authors and was delighted with what I found.  Not since the translation of the Three Body Problem, have I found a book so richly conceived and seeming to pulse with culture and a simple yet compelling world that felt like one part John Wick and one part Don Winslow.

Honorable Mentions:

Anyone by Charles Soule

A Man for All Markets by Edward Thorpe

The Fear Index by Robert Harris

Nothing Is True and Everything Is Possible: The Surreal Heart of the New Russia by Peter Pomerantsev

Dark Data:  Why What You Don’t Know Matters by David Hand

Coding Democracy: How Hackers Are Disrupting Power, Surveillance, and Authoritarianism by Maureen Webb


Previous Lists:

Top 10 Security, Technology, and Business Books of 2019

Best Security, Business, and Technology Books of 2018

Best Security, Business, and Technology Books of 2017

Best Security, Business, and Technology Books of 2016


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