This is intended to be a list of high signal books that have had a significant impact on my model of the world.
I have ordered them from most impactful/important to least.
I am usually reading between 10-15 books at once. Only the best have made this list.
All of these books I highly recommend.
Zero to One: Notes on Startups, or How to Build the Future
Zero to One: Notes on Startups, or How to Build the Future
Peter Thiel
Re-reading
The WEIRDest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous
The WEIRDest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous
Joseph Henrich
Re-reading
How to Win Friends and Influence People 
How to Win Friends and Influence People
Dale Carnegie
Re-reading
The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers
The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers
Ben Horowitz
Finished
What You Do Is Who You Are: How to Create Your Business Culture
What You Do Is Who You Are: How to Create Your Business Culture
Ben Horowitz
Finished
Loonshots: How to Nurture the Crazy Ideas That Win Wars, Cure Diseases, and Transform Industries 
Loonshots: How to Nurture the Crazy Ideas That Win Wars, Cure Diseases, and Transform Industries
Safi Bahcall
Finished
The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley
The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley
Jimmy Soni
Finished
How Innovation Works: And Why It Flourishes in Freedom
How Innovation Works: And Why It Flourishes in Freedom
Matt Ridley
Finished
The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness
The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness
Morgan Housel
Finished
Cracking the PM Interview: How to Land a Product Manager Job in Technology
Cracking the PM Interview: How to Land a Product Manager Job in Technology
Jackie BavaroGayle Laakmann McDowell
Reading
The Power Law: Venture Capital and the Art of Disruption
The Power Law: Venture Capital and the Art of Disruption
Sebastian Mallaby
Finished
Antifragile: Things That Gain from Disorder
Antifragile: Things That Gain from Disorder
Nassim Taleb
Reading
The Black Swan: The Impact Of The Highly Improbable
The Black Swan: The Impact Of The Highly Improbable
Nassim Taleb
Finished
The Innovator's Dilemma: When New Technologies Cause Great Firms to Fail
The Innovator's Dilemma: When New Technologies Cause Great Firms to Fail
Clayton Christensen
Reading
Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley
Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley
Antonio Garcia Martinez
Finished
The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
Max Chafkin
Finished
The Social Leap: The New Evolutionary Science of Who We Are, Where We Come From, and What Makes Us Happy
The Social Leap: The New Evolutionary Science of Who We Are, Where We Come From, and What Makes Us Happy
William von Hippel
Finished
The Red Queen: Sex and the Evolution of Human Nature
The Red Queen: Sex and the Evolution of Human Nature
Matt Ridley
Finished
The Man Who Solved the Market: How Jim Simons Launched the Quant Revolution
The Man Who Solved the Market: How Jim Simons Launched the Quant Revolution
Gregory Zuckerman
Finished
Secrets of Sand Hill Road: Venture Capital and How to Get It
Secrets of Sand Hill Road: Venture Capital and How to Get It
Scott Kupor
Reading
Super Founders: What Data Reveals About Billion-Dollar Startups
Super Founders: What Data Reveals About Billion-Dollar Startups
Ali Tamaseb
Finished
Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts
Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts
Annie Duke
Finished
Angel: How to Invest in Technology Startups-Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000
Angel: How to Invest in Technology Startups-Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000
Jason Calacanis
Finished
The Courage to be Disliked: The Japanese phenomenon that shows you how to free yourself, change your life and achieve real happiness
The Courage to be Disliked: The Japanese phenomenon that shows you how to free yourself, change your life and achieve real happiness
Ichiro KishimiFumitake Koga
Reading
Influence: the Psychology of Persuasion
Influence: the Psychology of Persuasion
Robert Cialdini
Finished
Scrum: The Art of Doing Twice the Work in Half the Time
Scrum: The Art of Doing Twice the Work in Half the Time
Jeff Sutherland
Reading
The Rational Optimist: How Prosperity Evolves
The Rational Optimist: How Prosperity Evolves
Matt Ridley
Reading
The Cold Start Problem: How to Start and Scale Network Effects
The Cold Start Problem: How to Start and Scale Network Effects
Andrew Chen
Reading
Alchemy: The Surprising Power of Ideas That Don't Make Sense 
Alchemy: The Surprising Power of Ideas That Don't Make Sense
Rory Sutherland
Finished
Lifespan: Why We Age - and Why We Don't Have To
Lifespan: Why We Age - and Why We Don't Have To
David Sinclair
Finished
Super Crunchers: Why Thinking-by-Numbers Is the New Way to Be Smart
Super Crunchers: Why Thinking-by-Numbers Is the New Way to Be Smart
Ian Ayres
Finished
The Power Broker: Robert Moses and the Fall of New York
The Power Broker: Robert Moses and the Fall of New York
Robert Caro
Reading
Warlord: A Life of Winston Churchill at War, 1874-1945
Warlord: A Life of Winston Churchill at War, 1874-1945
Carlo D'Este
Finished
Anatomy of Love: A Natural History of Mating, Marriage, and Why We Stray
Anatomy of Love: A Natural History of Mating, Marriage, and Why We Stray
Helen Fisher
Finished