Some of this I put together for Max originally, but I keep adding to it. Obvious disclaimer: Your mileage may vary with book recommendations ⏤ I'm different from you, and my tastes are obviously mine. So read GoodReads reviews etc. if you're not sure.
Kevin Starr - California: A History // Probably the starting point if you're serious
Irving Stone - Men to Match My Mountains // timeless and fascinating read about the history of Western settlement of California
Daniel James Brown - The Indifferent Stars Above // all you ever wanted to know about the Donner party
John Steinbeck - The Grapes of Wrath // The grand novel of the Great Depression and the migration to California (relevant but depressing)
Marc Reisner - Cadillac Desert // classic on the grand water scam and the foundation of California politics
Peter Thiel - Zero to One // regardless of what you think about Peter Thiel's politics, he is incredibly smart and insightful. Worth a read
Antonio Garcia Martinez - Chaos Monkeys // if the show Silicon Valley had been written by someone who had actually lived in Silicon Valley and founded a company, this is what it would be
Michael Lewis - The Big Short // (or anything else by Michael Lewis - like Flash Boys, or Moneyball, or The Undoing Project)
Lawrence Cunningham and Warren Buffett - The Essays of Warren Buffett: Lessons for Corporate America // should be mandatory reading for anyone who ever confused speculation and investment, or really for anyone with an interest in corporate finance and management
A.G. Lafley and Roger L. Martin - Playing to Win: How Strategy Really Works // I'm guessing strategy is a bit like expertise - for true experts, what they actually do does not easily translate into a chart, simple process, or recipe. But this book has merit.
Bob Wachter - The Digital Doctor // Why things are what they are in the field of medical informatics
Atul Gawande - The Checklist Manifesto // (or anything else by Atul Gawande - I'm a big fan) Great book about safety or the lack thereof
Viktor E. Frankl - Man's Search for Meaning // Until I read this book, I was profoundly skeptical of anyone claiming to know anything about the meaning of life (regardless of whether they approached it from a philosophical, biological, or spiritual angle). Like I said, until I read this book.
Hans Rosling et al. - Factfulness // I saw Hans Rosling speak at the World Health Summit in Berlin, and he was one of the most amazing presenters I ever saw. This book captures his style perfectly.
I suppose I could put anything by Tversky and Kahneman here, as it greatly influenced my thinking.
Richard Powers - The Overstory // Approachable yet complex, like a great wine. Weaves together seemingly unrelated stories into a coherent and very satisfying whole.
Larry McMurtry - Lonesome Dove // I went through a Cormack McCarthy phase and read almost everything he wrote. Then I discovered Larry McMurtry. This is not for everyone (it's close to 1,000 pages, a love story, and a Western epic) but the language is beautiful.
Keri Hulme - The Bone People // Booker Prize winner. Not an easy read, but I remember it being amazing.
John Steinbeck // I know this is where I pick my favorite, but the fact is, pretty much anything by Steinbeck has these beautiful sentences and a vividness with which he sketches people and situations that make me want to hand-copy whole passages into my notebook of memorable things I read.
Kiran Desai - The Inheritance of Loss // Booker Prize winner (usually a good filter). Approachable, with vivid imagery.
Salman Rushdie - Midnight's Children // Another Booker Prize winner. When I finally read it, loved it from first page to last.
Günter Grass - The Tin Drum (transl. by Breon Mitchell) // Nobel Prize winner. I re-read this (in a new translation) recently. The magic realism ("broadened reality") combined with the compelling story make this a great read.