The very best nonfiction books

The Fun / Impact access

My friend Tim once told me that “one of my superpowers is recommending books to people.” This obviously pleased me immensely and I think there are two main things to take away:

• You should tell your friends what their superpowers are! It’s a very nice thing to hear and they don’t always know it and they’ll remember it

• You should read all of the books that I recommend to you

It is one of my favorite things to do and when someone actually reads and enjoys one of my recommendations it’s a wonderful feeling, like successfully setting up two friends but with a lot less risk.

I try to keep track of books I read, and it’s fun to bring some structure to my feelings towards them. So I rated the books on the two axes that are most important to me: “Fun” and “Impact.” For me, a nonfiction book must either be fun¹ or impactful for me to enjoy it and recommend it.

So check these out! The links are affiliate links, so if you buy something from Amazon after clicking one of them (including, like, that beautiful Le Creuset set you so deeply deserve), I’ll get a little kickback. Then, I’ll plow that revenue back into R&D and be able to write even BETTER listicles — bit of a “flywheel effect,” if you will.

Best All Around:

1. Dataclysm, by Christian Rudder (cofounder of OkCupid): I read this when I was 19 or so and I remember being so delighted by the way Rudder could use data to understand people better. This book answers amazing questions like “what questions predict a person’s political affiliation?²” and “what questions most correlate to relationship success?” It’s very fun and given what I do now it’s among the most impactful books I’ve ever read.

2. Working, by Robert Caro (author of Power Broker & LBJ bios): I think Caro is such an inspirational person and this book is the best example I’ve encountered of someone finding what they were born to do. Caro recounts the story of going through documents when investigating corruption behind building La Guardia airport, and looking out and seeing the sun rise and realizing he’d been there all night. It’s really beautiful, and Caro has a wonderful grandfatherly voice so it’s perfect on audio.

3. The Art of Gathering, by Priya Parker: This book analyses what makes gatherings of people work well and describes how to make them better. Lots of fun tidbits like “if you’re having a dinner party, make sure the table is enclosed, so that it feels intimate.” I’ve referenced it enough that it annoys my friends which is a good indication of its impact.

4. The Biggest Bluff, by Maria Konnikova: I listened to this walking in San Francisco during the pandemic and it brought me to the poker table with Konnikova, a journalist who became a professional poker player after investigating it for a story. Will make you want to play poker.

5. Predictably Irrational, by Dan Ariely: I have a weird relationship with this book because it made me want to major in economics and understand why people do the things they do. But there have been credible allegations of Ariely doctoring data, which makes me sad.

Most Fun:

1. The Snow Leopard, by Peter Matthiessen: Listen to this on audio. Matthiessen may be the coolest person ever (helped set up the Paris Review, wrote award-winning fiction and non-fiction, worked for the CIA), and he recorded the audioboook of this story of his trek in the Himalayas when he was very old, and sitting in a room with his friends. It’s incredibly intimate and spiritual feeling. A beautiful book.

2. All the President’s Men, by Woodward & Bernstein: For a while during after Trump’s election in 2016 I listened to this while I was falling asleep. The cloak & dagger nature of the Watergate scandal is very fun and honestly the political malfeasance seems quaint relative to today, which is why I found it calming.

3. Very Important People: Status & Beauty in the Global Party Circuit, by Ashley Mears: I wrote about this book here. Learning about the economy of club promoters, the young models they bring to high-end clubs, and clients buying bottle service was fascinating, and made me look around for promoters whenever I walk through Soho.

Most impactful:

1. Black Swan, by Nassim Taleb: Taleb seems like an awfully obnoxious person but this book impacted my worldview a lot (it provided my senior quote in high school, as I noted here). Its overall premise of “nobody knows what will really happen in the world, so expose yourself to potential positive upside” has stuck with me.

2. A Random Walk Down Wall Street, by Burton Malkiel: I was lucky to read this book at a young age because it convinced be that I could not beat the stock market and I should just put my money into index funds, which I still believe to be good advice, for the most part.

3. The Power of Habit, by Charles Duhigg: This one is kind of lame because along with Atomic Habits it’s a canonical self-improvement-bro book. But I think habits are really powerful and reading this helped me better understand how to form them or break them. I wrote about them here and visualized my meditation habit a few years ago.

Special Mentions:

If you live in San Francisco, please read Season of the Witch; it’s such a fun and fascinating history of the city and made me enjoy living there way more.

The Autobiography of Gucci Mane is fast and really interesting and fun (and may edge out Springsteen’s autobiography as my favorite musician book). It has the coolest cover of any book on here:

Educated was wonderful and provided a much more interesting look at class in America than Hillbilly Elegy did.

Would love to hear your thoughts on any of these, or if you think there’s something I’d enjoy based on this let me know!

1. I guess by “Fun” i mean “enjoyable to read”; i felt I needed to clarify that when adding Empire of Pain about the Opioid Crisis.

2. “Do you prefer people in your life to be simple or complex?” Predicts political affiliation; Whether two people like or dislike horror movies predicts relationship success. See this blog post for more.