As a reference, my grading scale is:

One Star: Not recommended for any number of reasons (poorly written, lack of content, poor depth-to-length ratio).

Two Stars: Not recommended, but tends to have a few worthwhile moments that would merit skimming, or is written for a small niche that might find something worthwhile.

Three Stars: Recommended, but either covers too niche a topic to get a stronger recommendation for a broad audience or doesn’t offer enough depth to be really interesting.

Four Stars: Recommended, well-written, and covers material I think most people would find useful or interesting.

Five Stars: Strongly recommended due to superb writing or research material. These books could expertly appeal to a wide audience or cover their subject so thoroughly to be authoritative accounts of their topics.

Additionally, I pick one book every six months as the “best book I’ve read” during that time period.

Three Star

Hipster Business Models – How to Make a Living in the Modern World by Priceonomics: Disregard the cheesy, off-putting title. Hipster Business Models is a collection of essays on eccentric ways people are making money, such as a Cheeto photographer and brothers who travel the country in a van doing odd jobs. The level of interestingness and originality varies from story to story. The essay format makes each chapter readable on its own and the less interesting ones skippable. A quick, fun read to give you ideas for how you’d make money if circumstances forced you to get creative, or you want to monetize your pre-existing offbeat side.

The Third Wave- An Entrepreneur’s Vision of the Future by Steve Case: The cofounder and CEO of American Online has released his first book almost two decades since he took AOL to the peak of the dot-com bubble. I decided to pick this up when I happened to see it on the shelf at a nearby Barnes and Noble and recognized it from Steve Case’s marketing blitz for it the past few months. Named after a book of the same title by futurist Alvin Toffler that Case read when he was younger, “The Third Wave” is half memoir and half futurology, with alternating chapters covering Case’s story in building AOL in the 90s and his predictions for the future of the internet.

The three waves as described by Case are three approximately 15-year periods: First, 1985 to 2000 as the period of building the Internet and its infrastructure; Second, 2000-2015 when companies made web applications and businesses on the Internet; and now the third wave is building “the Internet of Everything”, where all of society is imbued with the Internet in the same way electricity is embedded into modern life.

Considering the book covers two topics, Case keeps the writing succinct and readable. While not particularly deep on any of the future topics, it’ll provide less techno-centric people interesting brainfood on the future of the Internet and insight into the making of AOL, one of the flag-bearers of the Internet gold rush.

Work Rules – Insights From Inside Google That Will Transform How You Live and Lead by Lazlo Bock: Google’s Head of People Operations has written the manual for how Google hires and manages employees and creates an environment which has won numerous “Best Places to Work” awards. Bock’s writing style is simple and full of wisdom, as if Mark Twain ran your human resources department. The big difference between Google and most other companies is a bias towards trusting people and believing they are generally morally good. This one belief informs all other management decisions. The key takeaway from this book, beyond the specific Google-implementation examples, is that most companies can replicate Google’s culture, and many already have with great success.

Four Star

Phishing for Phools – The Economics of Manipulation and Deception by George Akerlof and Robert Schiller: Structured like a dissertation without any of the charts or equations. It concludes with a chapter specifically explaining its contribution to the economics field, which I’ll attempt to summary in a jargony one-liner:

Deception by people or firms is a natural outcome in competitive free markets where there are profit opportunities caused by informational or psychological asymmetries.

While that should summarize the message of the book, it’s an incredibly quick and fun read as the two economics Nobel Prize winners walk through a dozen examples of this dynamic. Highly recommended for anyone interested in economics or psychology. Only reason it doesn’t earn a five is because there’s not a lot of “new” knowledge, just new semi-formal framing and perspective on problems most people already understand intuitively.

Five Star

The Sixth Extinction – An Unnatural History by Elizabeth Kolbert: A truly historic event is happening to life on Earth, and it’s not just climate change. We are in the midst of what scientists identify as an “extinction event”, a short period of time where the diversity of life on Earth rapidly diminishes.

“Sixth Extinction” is structured, like many books I like, with two alternating running stories. Half of the book follows Kolbert’s global travels as she tracks down scientific experts on endangered and extinct species, interviewing them on why we’re observing such a loss of global organism diversity. The other half of the book is a walkthrough of the history of extinction research with highlights of the prominent geologists, zoologists, and other-ologists who’ve promoted the idea that species can be both appear and disappear during the historical timeline of life.

One surprising theme Kolbert uncovers is that modern humans are not just causing our current extinction event, but caused previous ones as well, as identified by the correlation of human expansion with the major declines in species extinction over tens of thousands of years.

The journalism is detailed, the scientific explanations understandable, and the stakes high. Winner of the Pulitzer Prize, “The Sixth Extinction” is a must-read for anyone who considers themselves thoughtful and desirous in understanding the fate of humanity.

Managing Humans – Biting and Humorous Tales of a Software Engineering Manager by Michael Lopp: In my last set of reviews, my top pick was “High Output Management”, which was partially about being an executive leader of a large (technology) organization. “Managing Humans” is a great complement, giving very tangible recommendations for working with and managing people (and not just in the software business). Drawing from decades of experience as a leader at some of the preeminent companies in Silicon Valley (seriously, check out his resume), Lopp provides tips for running meetings, getting the most out of your team without them hating you, how to work across departments, interviewing (on both sides of the table), and much more. This is all done with the same clarity and wit as his blog Rands In Repose.

The Best Book I’ve Read In The First Half of 2016

But What If We’re Wrong? Thinking About the Present As If It Were the Past by Chuck Klosterman: For my 2010 self, Chuck Klosterman was a name I was only vaguely aware, having seen it mentioned by other journalists in articles about pop-culture and on the recognizable cover of his book “Sex, Drugs, and Cocoa Puffs”.

Then in the Autumn of that year, the NFL released a video series on the 100 greatest football players in history. O.J. Simpson, a hall of fame-caliber football player and world-renowned convicted felon, made the list. His video package was narrated by Chuck Klosterman. I knew little about both men. I was struck by Klosterman’s willingness to acknowledge someone for their tangible accomplishments when I’m sure many others would be unwilling to do the same.

This stellar video, where Klosterman explains how O.J. Simpson may have arguably been the best football player in the world for a few years in the early 70s and held the records for most yards in a single game and season, was posted by the NFL a few weeks ago.

“But What If We’re Wrong” is not about football, but it is a continuation of Klosterman’s willingness to question convention. The subtitle is an accurate one-liner of the content. I’ll rephrase it as, “How will future humans, when looking back in history, think about the time we are currently living in?”

My restated subtitle of the book is answered by the implication of the title: What we currently think is important and what we think will be important to future generations is most likely wrong. The primary supporting argument is that this has historically been the case; what we currently think about past generations is rarely what past generations thought about themselves.

This point is supported with chapters on individual cultural aspects: literature, music, television, architecture, physics, sports, and politics. Each theme is then dissected in two ways: what are the past and present beliefs in this field, and what do we think the future human beliefs will be on this same issue?

The conclusion, as suggested by Klosterman, is that the future is unsurprisingly unknowable, yet people are unsurprisingly confident about their knowledge. This leads Klosterman into an overlapping field with one of my other favorite (and previously reviewed) authors, Nassim Taleb.

Klosterman’s work, while thematically similar to Taleb, is more of cross between Malcolm Gladwell (writing about complex topics in a simpler, relatable style) with the pot-smoking burnout most people know at least one of in real-life or have seen in movies (this comparison due to pattern of finding profundity in the banal, superficial aspects of life). However, this comparison is meant as a compliment. Chuck elevates himself above perpetual stoners having “high-deas” in dorms by concretely producing coherent content.

Past work had elevated Klosterman from music critic to cultural commentator. “But What If We’re Wrong?”, which I read in a few non-stop sittings a few weekends ago, firmly places him in my opinion as a mainstream cultural philosopher.