Thanks for the great list @zackchase !! I shall queue up some of these on my reading list.
Here are some book recommendations, roughly split by category, with publication date in parentheses. (I'm excluding books I haven't read, since I can't judge them yet.)
Business/Tech
Crossing the Chasm: Marketing and Selling High-Tech Products to Mainstream Customers (1991)
The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses (2011)
The Second Machine Age: Work, Progress, and Prosperity in a Time of Brilliant Technologies (2014)
How Google Works (2014)
The Hard Thing About Hard Things: Building a Business When There are No Easy Answers (2014)
Zero to One: Notes on Startups, or How to Build the Future (2014)
Blockchain Revolution: How the Technology Behind Bitcoin and Cryptocurrencies is Changing the World (2016)
Throwing Rocks at the Google Bus: How Growth Became the Enemy of Prosperity (2016)
The Industries of the Future (2016)
Platform Revolution: How Networked Markets Are Transforming the Economy and How to Make Them Work for You (2016)
Machine Platform Crowd: Harnessing our Digital Future (2017)
Reinventing Capitalism in the Age of Big Data (2018)
AI, Science, Biology (Loosely)
Incognito: The Secret Lives of the Brain (2011)
Knocking on Heaven’s Door: How Physics and Scientific Thinking Illuminate the Universe and the Modern World (2011)
The Most Human Human: What Artificial Intelligence Teaches Us About Being Alive (2011)
Machines of Loving Grace: The Quest for Common Ground Between Humans and Robots (2015)
Our Robots, Ourselves: Robotics and the Myths of Autonomy (2015)
Algorithms to Live By: The Computer Science of Human Decisions (2016)
Dark Matter and the Dinosaurs: The Astounding Interconnectedness of the Universe (2016)
Heart of the Machine: Our Future in a World of Artificial Emotional Intelligence (2017)
Thinking Machines: The Quest for Artificial Intelligence and Where It’s Taking Us Next (2017)
Life 3.0: Being Human in the Age of Artificial Intelligence (2017)
AI Superpowers: China, Silicon Valley, and the New World Order (2018)
Blueprint: How DNA Makes Us Who We Are (2018)
History + Current Affairs
From Beirut to Jerusalem (1989)
The End of History and the Last Man (1992)
The World is Flat: A Brief History of the Twenty-First Century (2007)
The Post-American World (2009)
How Asia Works: Success and Failure in the World’s Most Dynamic Region (2013)
The Origins of Political Order: From Prehuman Times to the French Revolution (2010)
Political Order and Political Decay: From the Industrial Revolution to the Globalization of Democracy (2014)
The Billion-Dollar Spy: A True Story of Cold War Espionage and Betrayal (2015)
The Rise and Fall of American Growth: The U.S. Standard of Living Since the Civil War (2016)
Mission Failure: America and the World in the Post-Cold War Era (2016)
Playing to the Edge: American Intelligence in the Age of Terror (2016)
Enlightenment Now: The Case for Reason, Science, Humanism, and Progress (2018), and all of Pinker's other books which I'm still plowing through...
American Dialogue: The Founders and Us (2018)
LikeWar: The Weaponization of Social Media (2018)
Identity: the Demand for Dignity and the Politics of Resentment (2018)
Biographies
Alan Turing: The Enigma (1983)
My Beloved World (2013)
Lee Kuan Yew: The Grand Master’s Insights on China, the United States, and the World (2013)
Worthy Fights: A Memoir of Leadership in War and Peace (2014)
Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future (2015)
My Journey at the Nuclear Brink (2015)
Sisters in Law: How Sandra Day O’Connor and Ruth Bader Ginsburg Went to the Supreme Court and Changed the World (2015)
Hillbilly Elegy: A Memoir of a Family and Culture in Crisis (2016)
Alibaba: The House that Jack Ma Built (2016)
Churchill and Orwell: The Fight for Freedom (2017)
Psychology + Random (Loosely Speaking)
The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change (1989)
The Swerve: How the World Became Modern (2011)
The Signal and the Noise: Why So Many Predictions Fail – But Some Don’t (2012)
Give and Take: Why Helping Others Drives Our Success (2013)
The Road to Character (2015)
Peak: Secrets from the New Science of Expertise (2016)
Originals: How Non-Conformists Move the World (2016)
Deep Work: Rules for Focused Success in a Distracted World (2016)
Grit: The Power of Passion and Perseverance (2016)
Everybody Lies: Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are (2017)
Great at Work: How Top Performers Do Less, Work Better, and Achieve More (2018)
Other Comments
Of the books in your 2019 queue, I highly recommend:
Thinking Fast and Slow
The Master Algorithm: How the Quest for the Ultimate Learning Machine Will Remake Our World
All of Atul Gawande's books (I assume you've read "The Checklist Manifesto")
PS: When do you normally read books? I find I never have enough time and can only allocate mostly Saturdays for reading, along with plane rides (when it's impossible to get real work done in coach class).