Today, a simple topic: a power ranking of all of the books I’ve read about entrepreneurship, investing, and the startup world.

This list is the result of about four years of reading (and maniacally tracking that reading) about startups, investing, and Silicon Valley culture.

My Midwestern sensibilities almost didn’t let me publish this, for fear of being mean to the authors that are low in my rankings — but in the end, I decided that it was worth it to help you all prioritize your reading time.

Happy reading! Let me know what you enjoyed, and if I haven’t yet read anything that would go in your own Tier One.

🏆 Tier One: Must-reads

The 4-Hour Workweek (Tim Ferriss): Automate a lifestyle business, travel the world

"If you are too intent on making the pieces of a nonexistent puzzle fit, you miss out on all the real fun. The heaviness of success-chasing can be replaced with a serendipitous lightness when you recognize that the only rules and limits are those we set for ourselves."

Liftoff (Eric Berger): SpaceX almost died... many times
Originals (Adam Grant): World-changing originality is part-science
Elon Musk (Ashlee Vance): Worldview + Recruiting + Indomitable Will = Musk

😅 The Hard Thing About Hard Things (Ben Horowitz): Management book that admits startups are hard

“During the first layoff at our company, I remember being forwarded an email exchange… one of our smarter employees wrote, ‘Ben is either lying or stupid or both.’

I remember reading that and thinking, ‘definitely stupid.’”

How The Internet Happened (Brian McCullough): Market crashed, technology didn't
The Circle (Dave Eggers): Tech "utopia" doesn't sound so great
Steve Jobs (Walter Isaacson): Jobs was mercurial, self-aware, and taken far too early

🚀 Zero to One (Peter Thiel): Founders can change the world

"To believe yourself invested with divine self-sufficiency is not the mark of a strong individual, but of a person who has mistaken the crowd’s worship – or jeering – for the truth. The single greatest danger for a founder is to become so certain of his own myth that he loses his mind. But an equally insidious danger for every business is to lose all sense of myth and mistake disenchantment for wisdom."

✨ Tier Two: Great reads

Shoe Dog (Phil Knight): Morality is secondary to winning for Knight
The Last Days of Night (Graham Moore): Tesla thought, Edison reveled, Westinghouse developed

Uncanny Valley (Anna Wiener): Everyone's equal in SV, but some are more equal than others

"The men whom the CEO seemed to admire were the same men whom all the other men in the ecosystem admired: entrepreneurs, investors, one another."

The Messy Middle (Scott Belsky): Entrepreneurship is less glamorous than many admit
Angel (Jason Calacanis): Angel investing is high upside, all about hustle
The Space Barons (Christian Davenport): Space is hard

The Everything Store (Brad Stone): Founders shape companies to be like them

"In a way, the entire company is scaffolding built around his brain — an amplification machine meant to disseminate his ingenuity and drive across the greatest possible radius."

The Innovators (Walter Isaacson): Collaboration makes computers

👍 Tier Three: Read only after the above

Who is Michael Ovitz? (Michael Ovitz): Appearing all-knowing is a choice and Ovitz made it
Blitzscaling (Reid Hoffman): The Samwer brothers were “villains” and also right
Accidental Empires (Robert X Cringely): Bill Gates was a jerk; it worked
The Lean Startup (Eric Reis): Stay small, be fast, get customer feedback
Sapiens (Yuval Noah Harari): Humanity escalated quickly

High Output Management (Andy Grove): OG management advice from an OG manager

"When a person is not doing his job, there can only be two reasons for it. The person either can't do it or won't do it; he is either not capable or not motivated."

Alibaba (Duncan Clark): The strategy to win China: be Chinese
What You Do is Who You Are (Ben Horowitz): Culture is about your actions
Only the Paranoid Survive (Andy Grove): CEOs are often the last to know about changes
Chaos Monkeys (Antonio Garcia Martinez): Cynicism is the path of least resistance

Bad Blood (John Carreyrou): There’s a fine line between hype and fraud

"During demos at headquarters, employees would make a show of placing the finger-stick sample of a visiting VIP in the miniLab, wait until the visitor had left the room, and then take the sample out and bring it to a lab associate, who would run it on one of the modified commercial analyzers."

The Wizard of Menlo Park (Randall Stross): Thomas Edison was a jerk
Creative Selection (Ken Kocienda): Apple was all about demos and deciding for customers
The Innovator's Dilemma (Clayton Christensen): The classic, and mostly debunked, theory of entrepreneurship

🙅‍♀️ Tier Four: Skippable/skimmable

Venture Deals (Brad Feld & Jason Mendelson): Dry but useful reference book on venture finance
Zucked (Roger McNamee): Early advisor to Facebook has his regrets
How I Lost 170 Million Dollars (Noah Kagan): Dude got fired from Facebook
Valley of the Gods (Alexandra Wolfe): The Thiel Fellowship exists, kids are kids

✌,
Christian