2021 in Books

2021 in Books

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A Year For Thinking

Every year the books I read help me mark the calendar in my mind. I remember where I was any time I read a particular book, like a literary journal. I remember reading The Snowball in 2015 while I was in Uganda. I read John Adams when I was in Boston in 2016. Poor Charlie’s Almanack was a big part of the first year of quarantine. Beyond just the books I’ve read I have different experiences with reading that mark the passage of time and let me see the growth of the people around me.

The most significant development this year was that my oldest son became literate. In a combination of some reading classes we had him do during COVID and starting pre-school he finally started combining sounding out letters and writing out words. His ability to imagine things from what he reads on his own is something I wasn’t prepared for. There is no better way to appreciate something like the ability to read than seeing someone discover it on their own for the first time.



Fiction & Storytelling: I haven’t read much fiction with any consistency in my life. But the times when I do I get completely sucked into the universe. In 2019 I read a lot of the Red Rising series, but then in 2020 I didn’t read any fiction. While noticing my lack of exposure to fiction I also finally gave into a recommendation that I’d gotten from some of the most well-read people I know: read Brandon Sanderson. I read 6 of the Mistborn series this year and was struck by his ability to build a world and quickly introduce you to characters that you care so much about. The longer I’ve been an investor the more I’ve realized storytelling is a critical life skill.

Story vs. a Snapshot: My approach to investing is building a biography of a business. The history, details, trajectory, and milestones. Think The Profile, but for businesses. There are some fantastic podcasts out there doing this sort of thing, like Acquired and Business Breakdowns. But a lot of times the best information comes from exhaustive work in books like The Everything Store and Amazon Unbound.

How To Think: Several of the books I read this year revolved around helping me more effectively evaluate how I think. "All of humanity's problems stem from man's inability to sit quietly in a room alone.” The push for activity over reflection can cause a whole host of problems. I came across a few great resources this year to better guide my reflection time. Whether it was parenting (The Self-Driven Child), reading (How to Read a Book), money (The Psychology of Money), or just general overviews of the ways people think (The Great Mental Models, Reinventing Knowledge).

Added a “Quake Book”: Every year I pay attention to the books that have an outsized impact on me (usually I can spot them when I find myself wanting to highlight the whole book) and add them to my list of quake books. This year I added one that made me think deeply about the institutions we use to create knowledge and wonder what that will look like in the future.

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The Books I Read This Year


I saw a review for The Death of Expertise in 2017 and have rarely stopped thinking about the title. The subject has become increasingly more relevant in my mind. “These are dangerous times. Never have so many people had so much access to so much knowledge and yet have been so resistant to learning anything.”

We’ve seen the evolution of “experts” online progress from infectious disease to inflation. I always want to be on the humble end of the competence curve regarding my own knowledge and have a discerning eye when it comes to evaluating other people’s expertise. “Respecting a person’s opinion does not mean granting equal respect to that person’s knowledge.”


My wife and I have two sons that keep us plenty busy. Not only are we always trying to be better in the way we raise them, she and I also enjoy spending time together. So our routine for the last few months was reading this book together after the boys go to bed.

Most people’s natural inclincation as parents is to do everything they can to control their kids. No one says it in those terms, and few people acknowledge what they want as control instead of disguising it as a desire for safety or security.

The most dangerous part of helicopter parenting is not the impact it has on the parent / child relationship. Kids can be literally left unable to fend for themselves emotionally.


In 2016 I briefly worked for Amazon. I remember walking to work one day and looking up Amazon’s valuation. It was around $300B and saw that it was less than companies like Facebook or Microsoft. Everything I knew made me believe that Amazon had significantly more potential as a business than any others I was familiar with.

Since then I’ve been a proud Amazon shareholder and have always respected what Jeff Bezos has built. From the vertical integration to opportunity canvassing to leadership principles. I’ve wanted to study Amazon more deeply as a business and when Amazon Unbound came out I figured it was a good time to read both.


No business book has been more recommended to me other than maybe Shoe Dog. To have it be so recently released felt more like reading the news than a history. Jeff Bezos talks about how it’s always “day one” at Amazon but its clear a lot has changed over the last 20+ years. Brad Stone’s journalism presents itself as well. The story is well told and presents the whole picture without just being satisfied with Amazon fanboying. The stories of how Amazon expanded culturally and geographically is fascinating and rarely something that businesses have to tackle at such massive scale. I liked the book so much that it was one of my contributions to the Index Ventures library (and Brad Stone liked it!)


There are a few books and thinkers that are canon in the Roam community. How To Read a Book is near scripture. I’m an information hoarder and when it comes to books I eventually want to read the list is never ending. Big thanks to the Roam Book Club for finally giving me the push to read this book. My first introduction to this kind of methodical reading was called Surgical Reading and it struck me as something that I had always wanted to do better but never had the structure to do well. I learned plenty; “anything worth doing is worth doing wrong,” but this approach gave me a much more methodical way of evaluating what I’m reading and what I’m taking away from it.

Syntopical reading remains underrated. The result is the difference between reading for information vs reading for comprehension.”


Everyone will compliment Brandon Sanderson on his world building. The thought that goes into the magic, the mythology, and the culture is powerful. What struck me more was the journey of faith that one of the characters takes the reader on as they explore what makes a God? A religion? A system of belief?

Sazed asked, "Tell me, Mistress. What is it that you believe?" Vin frowned. "What kind of question is that?" "The most important kind, I think.”

Church membership in the US fell into the minority for the first time in history (47% as of 2021). People are replacing God in their lives with a host of all kinds of things. What I think is most lacking is the self-reflection from people to really ask themselves “what do you believe?”


As I read the second book I continued to fixate on this journey of faith. While one of the characters goes through a crisis of faith he’s confronted with the simple views from many of the other characters. Much of the book is about trust, promises, and the relationships we choose to engage in.

“Religions are promises--promises that there is something watching over us, guiding us.”

What promises do you choose to believe in? Whether its promises from institutions, individuals, employers, or yourself. For me I look to promises of becoming better. Wherever I can get the promise of becoming a better person, a better husband and father, a better investor, a better friend or leader. That’s what I look to.


In the conclusion of the first trilogy I saw a really compelling conclusion to this crisis of faith. As one character searches for what to believe in they’re confronted with reality.

“It sounds to me, young one," Haddek said, "that you are searching for something that cannot be found." "The truth?" Sazed said. "No," Haddek replied. "A religion that requires no faith of its believers.”

Choosing what you believe in isn’t and shouldn’t be an easy thing. And if it is an easy belief to hold, then is it worth holding? Joseph Smith said that “a religion that does not require the sacrifice of all things never has power sufficient to produce the faith necessary to lead unto life and salvation.”

Look for the things that are true and fight to understand them. That, to me, feels like the only life worth living.


The second trilogy of the series focuses on a different set of characters in a different time. Another credit to Brandon Sanderson, I always worry whether I’ll care about a new set of characters but he gets me to care so much so quickly.

I walked away thinking about choices. Everyone is placed in an environment they ultimately can’t control and they only have their choices. “The measure of a person is not how much they have lived. It’s in how they make use of what life has shown them.” Everyone can either act or be acted upon.People today … it seems they are good, or sometimes evil, mostly by inertia, not by choice. They act as their surroundings prepare them to act.”

The critical point is to reflect on whether you are actively making choices or letting your environment act for you.


Where the first trilogy was castles and warriors the second trilogy is like a western mystery series. As the story chases after a criminal, I kept coming back to my thoughts on ‘choices.’ There is a broader debate about free will when it comes to the value of our choices, especially when you throw God in the mix.

The villain in the book argues that “there are no good men... There are those created to be selfish and there are those created to be selfless. This does not make them good or evil, any more than the ravaging lion is evil when compared to the placid rabbit.” If you believe in an all-knowing, all-powerful God it becomes complicated to believe you have choices. But “to believe in a God was to accept that He or She wasn’t going to deliver you from every problem.” So your choices are reacting to the problems you’re faced with.


Throughout the second trilogy the main character is a lawman who repeatedly has to wrestle with the choices he’s made. There are plenty of times when he could choose not to chase the bad guy or put the people he loves in danger. But that’s not a choice he can make. In one conversation with God he confirms the decision to do his job.

“I have to.”

“Do you?”

“I have to. It’s who I am.”

“Then perhaps,” [God] said, “you should stop hating that.”

It reminded me of a quote: “What we insistently desire, over time, is what we will eventually become.”


I’ve been listening to Shane Parrish since college and have always appreciated his summary of great ideas. Poor Charlie’s Almanack was a broad sweeping story book of key mental models illustrated by life. This book is a simple introduction to key ideas that is more catalogued and direct.

"Take a simple idea and take it seriously.” (Charlie Munger)

The more I think about this quote the more I realize that taking an idea seriously requires a fair amount of effort and dedication.


There are few places in the world I love more than bookstores. I think about Bookstore Economics every time I walk into one. Recently I was in Powell’s in Portland and happened upon this book. Rarely do I read a book that I haven’t had recommended to me by several people. This was a rare exception. What I loved about this book was seeing the relationship between institutions and knowledge. Whethers its libraries, monastaries, or universities. Even more this book added a pillar to my Portfolio Ideas when I came away captivated by The Republic of Letters. “The Republic of Letters can be defined as an international community of learning stitched together by handwritten letters in the mail.” I’m now thinking a lot about The Republic of Letters 2.0 and what this looks like in the internet age and the creator economy. Are DMs the new letters?


One of my Portfolio Ideas is something I call Live The Library. Morgan Housel has been on my list for a long time. He’s one of the most impactful people I follow on Twitter and this book was recommended to me by just about everyone that I have respect for.

What struck me about this book was both its brevity and its impact. “It’s not a long book. You’re welcome. Most readers don’t finish the books they begin because most single topics don’t require 300 pages of explanation.” The focus on psychology helped me step back and look for core truths of human behavior vs. tips and tricks. “I love Voltaire’s observation that ‘History never repeats itself; man always does.’”


Every few years The Church of Jesus Christ of Latter-Day Saints has put out an overview of a differet part of the Church’s history to more effectively unpack the details. Late last year McKay Coppins wrote a piece in The Atlantic called “The Most American Religion.” The religion of the Church of Jesus Christ of Latter-Day Saints traces its roots back to Jesus Christ but celebrates the heavenly vision of a 14-year old boy seeing God and Jesus Christ in 1820 (just passing 200 years ago.)

A lot of people will look at the history of any religious organization and struggle to believe it. For me, I think a lot about the idea that “a good tree bringeth forth good fruit. Wherefore, by their fruits ye shall know them.” This book helps me better appreciate the fruits of the religion to which I belong.