Books 2019

I didn’t set out to read a book for each month but it turns out I read 12 books in 2019, so there you go. It was my readingest year ever as I had time available and I made sure I took it. I bought my first Kindle in the last few days of 2018 and it was a great investment.

Some of the books I read were in preparation for chasing my next opportunity and upping my leadership game. There is likely a lot of overlap in this group with others I know in similar boats doing their own reading.

Others were related to helping close friends I know that are doing the hard work of trying to heal from past trauma. I read those books to help vet what books might be useful to them and in the process learned a lot more about a complicated subject that I think in the process helped me be able to be a better friend generally.

And the last group were miscellaneous topics of interest touching on things like economics, geopolitics, and important history.

I’m glad I took the time that I did to read this year, and I’m hopeful I’ll be able to make the time to read a good amount in 2020 also.

“Biz” Books

Half the books I read were in this category and with an eye toward preparing better to create something new. I’m guessing these will be familiar to you, but if nothing but for my own future reference I wanted to give a mention and little summary of each.

I think Play Bigger was the first of the biz books that I read in 2019 and it got me animated more than any of the other ones. It defined a process for thinking beyond a product idea and expanding thinking to how to define a category that a product can be the defining solution for. Define the category, own the category, win big.

Another book that was about tackling categories was Zero To One. I had been hearing mentions of this book and maybe because the author Peter Thiel has become such a polarizing figure that got me intrigued also. This book pushed for tackling brand new things, having more audacious goals and I think fair to say start with a category and figure out the product from there.

The ONE Thing comes at one concept from a few angles, that you should figure out the single thing that will have the most impact on the most important thing you want to accomplish, and make that the thing you put work into. It’s important to note that the idea here isn’t to work all the hours of a day on a single thing until it’s done and then move on to the next thing. It’s more about identifying the top priority in any given endeavor (work, parenting, personal, etc) and time-blocking times to focus exclusively on the most impactful single thing to move the ball forward. I can’t say I’ve quite been able to adopt the approach, but it HAS gotten me to focus more aggressively on prioritizing and making sure I bias toward the most important thing I need to get done. It’s a simple idea, but might require reading the book to have it driven home and taken to heart.

What I’m doing next is providing a solution in the consumer space and so from everything I had heard, Hooked was a must-read. It did not disappoint on getting the juices flowing on thinking of product design and user behaviors. Key concepts: Internal Trigger (what pain the product is relieving), External Trigger (why users come to the service), Action (what simple thing can users do to accomplish a goal), Variable Reward (both fulfilling user need but have them still wanting more), and Investment (bit of work that makes them invested and loads the next trigger).

A book I jumped on as soon as it became available, just based on the recommendations I was seeing about it on twitter was The Great CEO Within. This one is like a guidebook for the modern startup founder with great suggestions for what to think about and what needs to be done, whether it’s how to raise money, how to incorporate, how to set culture, how to invest your money, etc. I read this one through once knowing I’d be coming back to reference it again and again.

I came to What You Do Is Who You Are after hearing an interview discussion with author Ben Horowitz about it on the a16z podcast, and while The Great CEO Within (above) has a good section on culture this book is solely focused on that topic. I loved how this book wasn’t just about business but instead was a combination of history as it relates to culture and application of those principles to business. This book is a great reinforcement of something I know from experience and that’s how important culture is to the success of an organization. Great historical references and also practical thoughts on how to think about setting culture.

I also did a little re-reading/skimming of a couple which are worth a mention: The Hard Thing About Hard Things,The Art of the Start, and the classic High Output Management.

Trauma Healing Books

These books weren’t read for pleasure, but were important. They are probably still good for me to come back and reference, and maybe useful for someone else.

Trauma healing as a category of book is probably an important one to have recommendations and luckily a friend recommended The Body Keeps The Score. Central to this book is how trauma manifests in other physical ailments, and how different therapies have been found to be useful, including those around physical movement. The book summarizes the work done by the author from his career start working with post-war PTSD patients and then to “Complex PTSD” (C-PTSD) work, including his failed fight to get C-PTSD officially into the last DSM as its own diagnosis. I know from friends how important this is for effective treatment.

Another book that came with recommendations, though I don’t remember from where, was Allies In Healing. This book also feels really important, and is about the support needed by the loved ones of those dealing with past trauma. For anyone in that position I think it’s an incredibly valuable book to read, because you can’t care for others properly if you don’t take care of yourself. Resources for loved ones of those healing from trauma are really hard to come by, so this book is an important starting point to exploring that.

Truth be told, I read a couple other related books in this category that were on the subject of DID (Dissociative Identity Disorder) and they were good for understanding the latest thinking of the dynamics in play with that diagnosis, but they are too complicated to summarize and really very specialized.


I began reading Wealth, Poverty and Politics in late 2018 but finished it in 2019 so I’ll count it here. I really enjoyed this well-researched and well-referenced book. A lot of it reminded me of Guns, Germs, and Steel on steroids, as it covered a lot of how natural resources shaped cultures which shaped various outcomes for different groups of people historically. After I read What You Do Is Who You Are (biz book discussed above) later in the year I thought back to this book’s discussion of culture and impact on outcomes, in particular as it discussed different immigrant groups in different times and places and how the culture they brought with them was a huge factor in their success in the society that they embedded themselves into.

I read The Chairs Are Where The People Go after listening to the author Misha Glouberman interviewed in an episode of the You Are Not So Smart podcast (which is a great podcast about cognitive biases). The book was fun, but hard to summarize because it has numerous chapters which are mostly their own little vignettes by the author about dealing with people in various ways. He took original thinking into various situations that were entertaining to read about. Also an easy book to take breaks from because for the most part the chapters could be taken independently.

I very much enjoyed Factfulness and its walk through the ways that life has been getting better in so many dimensions, for example the plummeting of both child mortality and extreme poverty rates. I highly recommend this book if you find yourself dragged into the thinking that things are getting worse. I think the core insight of this book was that things can simultaneously be bad and also getting better. It provided great perspective like stepping back to realize how poor much of Europe was even within current lifetimes (which tales from my wife’s family in Portugal even in the 1960’s corroborates). It also defines levels of poverty in ways that are accessible to understand and provides human connection to the problem while understanding the progress. Also really good information and thinking in here about how demographics of the world are changing, how population will level off by the end of the century or so, and the implications for the changing distribution of demographics across the world. This ended up intersecting with a lot of other reading (though not books) that I did on geopolitics in 2019 also.

While the author, Ibram X. Kendi, had a new book out (How To Be An Antiracist) in later 2019 that I haven’t read, I read an earlier book of his, Stamped From The Beginning. This was a very thoughtful book that traced the thread of the evolution of anti-Black racism from the early slave trade through to contemporary America. I tried to read about one chapter at a time and then let it sit so I could digest it. As with probably many books that cover a broad sweep of history there were too many people to keep track of, though the most important were the 5 that he centered the sections of the book around (Cotton Mather, Thomas Jefferson, William LLoyd Garrison, W.E.B. Du Bois, and Angela Davis). Woven through the book were the ways that ideas (including those of the 5 central figures) could be categorized as either Racist, Assimilationist, or Antiracist. I felt like this was an important read to absorb and a critical lens of American history regarding anti-Black racism that was definitely thought provoking.

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