Most Interesting Books of 2019

Yisong Yue
6 min readDec 31, 2019


The most interesting books I read in 2019, in reverse chronological order of reading them.

How F*cked Up Is Your Management?

I’m actually still in the middle of reading this one. The book is tailored to tech start-ups, but there are still interesting lessons to draw for the general case. The discussion around unlimited vacation days has been particularly interesting. Other interesting topics include facilitating true inclusion & diversity in the workplace versus just talking the talk, the value of one-on-one meetings, the effect of gossiping on workplace culture, interviewing well, and the superhero fallacy. Being a good manager is hard.

The War on Normal People

In his signature book, Andrew Yang makes the case for the inexorable tide of automation, universal basic income, and other a few other major ideas. The core narrative goes as follows. Automation has been eating away at the middle class for a long time, and its effects will only accelerate. Companies like Amazon contribute to closing down of local stores. While this process presumably brings reduced costs to the consumer, it also reduces local economic activity, leading to a “hollowing out” of the middle class. Much of the profits become increasingly concentrated in small fraction of the population, leading to either hyper competition (e.g., for schools and jobs), or disillusionment. The resulting mindset of scarcity makes people divisive and less compassionate towards others, amplifying some of the worst aspects of humanity that helped get Donald Trump elected. The way forward is to directly tackle this mindset of scarcity (without distorting the markets too much), which brings us to Andrew Yang’s flagship proposal: universal basic income.

As someone who works in AI, a few things Andrew Yang wrote did make me cringe (for instance, I don’t think we’ll get L5 autonomy in self-driving cars any time soon), but the general case he makes is pretty compelling. I’m also not quite sure how the math works out in terms of paying a UBI of $1K per month for every US citizen, as it involves projections based on the value-added tax, as well as on economic growth via this infusion of income that most Americans will spend quickly on every-day consumables. Nonetheless, I’m officially #YangGang, as I think these are the important conversations that we should be having in politics today.

The Dictator’s Handbook

This book presents an interesting discussion around incentives and how leaders create socio-political barriers to insulate themselves from accountability. The book touches on true dictatorships, democracies that disenfranchise their voters, and CEOs that insulate themselves from their board of directors. I’m not sure how much of the book is truly scientific, so perhaps take it with a grain of salt. But an interesting read nonetheless… made me think a lot about organizations and how bad behavior arises.

The Case Against Education

I suppose it’s kind of ironic that a university professor would be reading (and promoting) this book, but the book is AFAIK pretty scientific in its claims. The idea that a substantial fraction of the value of education is due to signaling rings true to me (the values range ~25% to ~75%, depending on the analysis). The upshot is that, because signaling is such a big part of the education value proposition, people feel compelled to go to university despite often learning very little of value. I don’t think anyone will deny that credentials creep is real in our society, and (circling back to Andrew Yang’s book) that our increasingly winner-takes-all economy strongly incentivizes getting a brand-name education. I hate to implicitly be a part of the problem, but I hope also to be a part of the solution someday.


This book documents the Peter Thiel backed lawsuit that Hulk Hogan filed and won against Gawker Media, which ultimately led to Gawker Media’s bankruptcy and the discontinuation of its flagship Gawker website. To the extent possible, the book tries to get at the motives of Peter Thiel, and describes an odd (but seemingly consistent) code of conduct that Thiel abides by. All in all, a fascinating story.

The American Slave Coast

This book discusses American chattel slavery from a primarily economic point of view, but also with a healthy dose of political issues sprinkled in. Like many things, money, power, and greed were principal drivers in institution of slavery. The book also describes the history of slavery and how it evolved to become so institutionalized in the United States, touching on (1) the realization of vast untapped potential of (what is now) the Southern US for farming, (2) the race to turn find cheap labor to fill the labor market (gotta love the “free” market), (3) the enthusiasm of West Africans to raid their neighbors and sell slaves to the European traders, (4) the relatively easy access to the slave market in West Africa due to maritime trade routes and Gulf stream effects, and (5) the eventual realization that slaves themselves are profitable financial instruments (since they provide interest via “natural increase”). By that point, the argument goes something like “slavery is too big to fail.”

By the time the US gained its independence, slavery had already been around for over 200 years, and was very institutionalized. The drafting of the US Constitution showed the incredible capacity for human beings with vested interests to de-humanize others and maintain cognitive dissonance. The structural weakness of the US Constitution around the issue of slavery all but ensured that a Civil War would come to pass. Anyone who believes the US government does not owe reparations to African Americans might do well to read this book.

Bad Blood

This book documents the rise and fall of Elizabeth Holmes, founder and CEO of the now defunct Theranos blood testing company. The book simultaneously tells three stories. The first is a cautionary tale of how the Silicon Valley mindset can backfire when dealing with potentially life-threatening errors such as a medical mis-diagnosis. The second is about ability of a single person to silence dissenters within an entire company, as well as keep the board of directors fooled (see above commentary on The Dictator’s Handbook). The third is about the (irrational) beliefs held by Elizabeth Holmes herself, and her treating criticisms of her technology as personal attacks (presumably because they threatened her self-narrative of ascendance). According to the book, she apparently never bothered to pause and reflect on how much harm she was causing others in pursuit of this narrative.

We humans love to build narratives about ourselves. These narratives can work well for a time, and bring others on board. But when we cling so tightly to a narrative that cannot withstand scrutiny or evolve when faced with new evidence, then we have a tendency to become (violently) defensive. Interesting species we are.