Books Read During a Year in Chicago

The last week of July marked my one year of living in Chicago. When friends visit my apartment, they tend to notice two things: The well-stocked bar my roommates and I maintain, as well as my massive book collection I leave laying in piles on my bedroom floor. Since I spend most of my free time reading paperbacks on a wide variety of topics, and people are always asking me about what I’ve read lately, I thought a quick review of every book I’ve read since I’ve moved to Chicago would be the best way to get all my book recommendations out to as wide an audience as possible.

I’ve ranked the books on a scale of five stars with five being the highest. At the end, I single out one book. Like any good article, I’ll start from the worst books I’ve read in the past year. If there is any book in particular you want to know more about, definitely reach out to me. I could write a whole essay on any of these.

One Star:

Atlas Shrugged by Ayn Rand:

I started this Ayn Rand 1000-page magnum opus while still in school and didn’t finish it until October 2012. The story features some great plot points, but is so painfully overwritten that I would not expect anyone to stick with it through to the end. It aims for an epic message yet struggles under the weight of the over-beaten dead-horse ideas it carries. Rand is supposed to be a writer, but her adjective abuse is appalling. Every other sentence reads: “The confident executive confidently gazed over the factory as a confident dictator looks over his country.” It’s simply too long and boring to recommend to anyone who doesn’t know what they’re getting into. If you’re looking for an interesting novel, there are others below I’d recommend. If you’re looking for a different perspective on philosophy or economics, read Hayek or Nietzsche.

Two Star:

The God Delusion by Richard Dawkins:

Probably considered the atheist’s bible, the God Delusion failed to answer the unanswerable. If you’re an atheist, the book probably doesn’t add anything you hadn’t already considered. If you’re a theist, then you can undermine the entire book by pointing out it does not provide an answer to the cosmological problem of infinite regress and the universe’s origins.

The Essential Drucker by Peter Drucker:

More like the Inessential Drucker (the jokes write themselves people). Peter Drucker is supposed to be a management expert. All I found in here was a lot of hand-wavy unscientific platitudes. The book is only redeemed by the fact that, since Drucker has been writing for half a century, it contains some interesting historical anecdotes.

Capitalism: The Unknown Ideal by Ayn Rand:

An Ayn Rand non-fiction book. I have no real complaints about the book. It contains a lot of solid rebuttals to socialism. However, nearly everything in it is better written elsewhere. Anyone who reads this would probably be better served reading Hayek and von Mises, whom Rand frequently cites.

Three Star:

Steve Jobs by Walter Isaacson:

Not the first Steve Jobs biography, but probably the best. Given the hype and exclusive access to Jobs himself, I was expecting a little more insight from Isaacson. Still a solid read and recommended to anyone who doesn’t know the background of the Apple cofounder.

Models Behaving Badly by Emanuel Derman:

I loved Emanuel Derman’s first book. Models Behaving Badly is an interesting mix of finance and physics short explanatory stories. Those looking for insights into flawed financial models will be underwhelmed.

The Shock Doctrine by Naomi Klein:

Naomi Klein does a tremendous job researching the dark side of the military-industrial complex and its self-serving nature. It’s a must-read for anyone interested in government corruption. The book loses me when she tries to use economic terms and butchers their meaning like the corporatists she’s denouncing. Clearly written by a journalist, not an economist, but she’s a good one.

How to Relax Without Getting the Axe by Stanley Bing:

Stanley Bing, my favorite author, manages to make me laugh again with this guide to getting paid without working. Compared to his novels and other business humor stories, this one is relatively thin.

Four Star:

The Mythical Man Month by Frederick Brooks:

This collection of essays is a must-read for anyone looking to manage large technology projects. A little dated (most of its lessons have been adopted by modern management), but for a book that’s forty years old, it still has a lot to teach its readers.

Boomerang by Michael Lewis:

Michael Lewis followed up The Big Short with this look into the brokenness of modern government budgets, particularly in Europe. Like all his other works, it’s fantastically written and reveals the complex problems of the world in simple language to the layman. My only issue with this book is that it’s thinner than most of his other books, lacking the deep research that makes his older books must-reads.

Venture Deals by Brad Feld and Jason Mendelson:

Almost shouldn’t qualify for this list, since it’s a textbook on how to raise venture capital. Brad Feld and Jason Mendelson do make the potentially dry material inviting and usable.

Who’s Your City by Richard Florida:

Professor Richard Florida provides an original perspective on what drives economic growth and personal happiness. His area of focus? Where you live. An educational mix of self-help feel-goodness and academic research helps individuals answer what he considers one of life’s major questions (where should you live?)

The Glass Bead Game by Herman Hesse:

Herman Hesse won the Nobel Prize in Literature in 1946. This book is cited as the primary reason. Set a few centuries into the future, a society of intellectuals exist in their own reclusive nation slowly reveals its weaknesses to the one man willing to think differently. At the same time, Hesse reveals himself to be as intelligent a writer as I have ever read. This doesn’t reach five stars as I wish there were aspects of the book that were explored further. Unlike Atlas Shrugged, this story certainly could have been longer and would have lost none of its luster.

Five Star:

What We Should Have Known by n+1:

This roundtable transcript by the writers of literary magazine N+1 is an enlightening window into the college experiences of now full-time writers. I bought it because I had read some articles by the staff and was impressed. The books premise is also intriguing (printing in book form the transcript of casual conversations between friends/coworkers). If you’re at all interested in our education system, literature, or the humanities, this quick read is easily worth its $9 price tag.

Too Big To Fail by Andrew Ross Sorkin:

Andrew Ross Sorkin’s book is probably the best (and thickest) retelling of the behind-the-scenes events which shaped the financial crisis during August and September 2008. Although it covers only a small portion of time, Sorkin’s detailed depictions of the personalities and stakes involved makes it a captivating must-read.

Andrew Carnegie by David Nasaw:

This is the definitive biography of one of the greatest businessmen in world history. David Nasaw went to great lengths to fact check everything, not even taking Carnegie’s own autobiography at face value. The result is tremendous insight into a uniquely gifted mind and the Industrial Revolution in which he thrived.

Dark Pools by Scott Patterson:

I’m biased toward loving anything finance related. Dark Pools deserves extra applause for providing a balanced perspective on the history of electronic financial markets. This story highlights the early pioneers of the field and their idealistic perspective on how markets should work, and how this utopia was corrupted into the broken systems we have today.

The Management Myth by Matthew Stewart:

This is the book I had been hoping to find for years. An ex-consultant lays waste to all the bullshit spun by the major management consulting firms. This enticing blend of historical research and anecdotes kept me immersed for all 300 hundred pages, leaving me with copious notes and confirmations of my biggest fears about how much of the corporate world operates.

Moneyball by Michael Lewis:

I was a little late to this party, considering the Brad Pitt movie was already on DVD by the time I got to reading the book. Nonetheless, it did not disappoint. The typical Lewis research and wit are present. The baseball theme allows this story to be the most welcoming of his books to a wider audience than his standard financial fare.

Hackers: Heroes of the Computer Revolution by Steven Levy:

This is the canonical history of hacker culture from the 1950s through the 1980s. Published in 1984, it’s a must read for anyone in the computer industry who wants to learn from their forebearers.

The Metamorphosis by Franz Kafka:

I had heard Kafka did most of his writing in the evenings after getting home from his day job pushing paper for an insurance company. His writing reflects his drab existence in surreal ways. Anyone working an office job will relate to his surreal stories.

The Black Swan by Nassim Taleb:

Nassim Taleb is one of the preeminent thinkers of our time. He admittedly isn’t explaining a whole lot that’s new knowledge. What he accomplishes is bringing old philosophical concepts into the modern age, applying them to concrete issues we face today, and then uses these principles to project into the future how people will behave. The fact that this book was published in 2007 predicting a financial crisis should be reason enough to read it.

Best Book I’ve Read in the Past Year:

Indecent Exposure by David McClintick:

One of my top three books of all time is Barbarians at the Gate. In its introduction, the authors credit Indecent Exposure as inspiring business journalists for generations to turn extraordinary business stories into gripping novels. Indecent Exposure is a hefty, 500 page tale of Wall Street and Hollywood. I finished it in a week. It sits in my personal pantheon of “Greatest Books Ever Read”. McClintick dives into the underbelly of two notoriously ego-driven industries and doesn’t surface for air for the length of the novel. When you hit what you think is the climax only 200 pages in, you realize that you’re in for a story grander than anticipated. And it’s non-fiction. I give this book the highest possible recommendation to anyone who has learned how to read.