Books Read in the Second Half of 2017

After a particularly busy year, I am playing catchup on the book reviews. Yes, I do realize it’s almost the end of 2018, but I still have 2017 books to write about.

Two Stars (Recommended only for those interested in the subject)

The Inevitable: Understanding the 12 Technological Forces That Will Shape Our Future by Kevin Kelly

Futurist Kevin Kelly’s book covers twelve technological trends (each described with one abstract term, starting with “Becoming” and ending with “Beginning”). Each chapter reads like a blog post on the subject. I’m probably a bit biased against the book because I already read a lot about technology, so none of the material seemed surprising to me. So the ideal reader is probably someone who doesn’t following the tech industry very closely but would like a readable overview of what’s to come. For everyone else, I’d recommend Kevin Kelly’s interview on EconTalk.

Three Stars (Recommended)

Grammar Girl’s 101 Misused Words You’ll Never Confuse Again by Mignon Fogarty

Mignon “Grammar Girl” Fogarty has been running her popular writing blog seemingly as long as I’ve been writing online. This pocket-sized guide provides “quick and dirty tips” to avoid misusing commonly swapped words. While about half of the 101 examples are known to most educated people, the surprising subtle lessons (like the difference between “purposely” and “purposefully”, or the controversial idea that “supposably” is a real, defined word separate from “supposedly” accepted in America but not British English) are worth the couple of bucks for this grammar pamphlet.

The Old Fashioned: The Story of the World’s First Cocktail with Recipes and Lore by Robert Simonson

Compared to most of my friends, I am nowhere near being a mixologist. I openly admit I only started drinking this cocktail because it was the drink of choice for Mad Men’s leading man Don Draper. Thankfully, “The Old Fashioned” acknowledges I’m not alone.

“The Old Fashioned” book has two ingredients: It starts with the lore and ends with the recipes. Simonson, whom is probably the foremost expert in The Old Fashioned and therefore has the coolest job in America, journalistically traces down the history and origin of the Old Fashioned cocktail as best he can. He freely admits that trying to pinpoint a creator is “a bit like saying a single person invented jazz.” The concise history is a fun read through alcohol’s relationship with various periods of American history and insight into mixologists’ minds.

Angel: How to Invest in Technology Startups – Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 by Jason Calacanis

I have a brief and long-forgotten history with Mr. Calacanis (and he surely won’t remember this story). While I was in high school, I AOL instant messaged Jason a question about the tech industry, when he was mostly a prominent blogger and not yet the investing and industry kingpin he is today. Without posting a copy of the conversation publicly, Jason responded and was super supportive of my tech industry ambitions at the time.

A decade later, I picked up his first book Angel about the art of investing as an individual. For those unaware, the gist of angel investing is a rich person investing their personal money into companies. Calacanis explains how to do this effectively, based on his experience as an early investor in hits like Uber: studying business, particularly technology startups, for a while before committing any money, spreading it around, combining your money with other individuals to create small investment funds, and expecting numerous failures and lost dollars along the way.

Calacanis, who also hosts the popular and entertaining This Week in Startups podcast, is known for his bombastic communication style. It may turn off some readers, but they’re probably missing the point. His point isn’t to sensationalize as much as, I think, it is to emphasize simple, blunt points and reality checking the wannabes who don’t really have the stomach for the failure it can require to make it in the startup life, even as an investor.

While the topic of Angel is very specialized, I can personally attest that Jason is genuinely out to help people and this is probably the best book on this niche.

Heather, the Totality by Matthew Weiner

The first novel by the creator of one of my favorite shows, Mad Men, is a brief, well-paced read. Written in short, simple sentences similar to Hemingway, this is a seamless read. Weiner’s pacing is perfect; he’s able to cover long periods succinctly and the story seems to speed up as it reaches its climax. Heather tells the story of a seemingly generic, middle-class white family and the dark secrets each of its members keep. The genius of the writing is that more average families hide dark secrets than they admit. A deceptive buildup to the twist ending helps make the book more memorable.

Digital Gold: Bitcoin and the Inside Story of the Misfits and Millionaires Trying to Reinvent Money by Nathaniel Popper

This is a book about Bitcoin, a concept whose popularity and general understanding has changed drastically since this book was written in 2015, since I read it in 2017, and since this review is published at nearly the beginning of 2019.

Author Popper captures the origin story of Bitcoin through extensive interviews with early Bitcoin programmers Hal Finney and Gavin Andresen and continues on to chronicle the obscure technology’s rise to fame through a colorful cast of characters, including: South American financial entrepreneur and early Bitcoin Wences Casares, the Winklevoss Twins of Facebook infamy, and Ross “Dread Pirate Roberts” Ulbricht of the Silk Road drug marketplace.

It’s interesting to consider to what extent books like Digital Gold contributed to the cryptocurrency mania that took over the technology news cycle in 2017. Regardless of where you fall on the spectrum of skeptic to utopian technologist, Digital Gold is a thorough and consumable read for anyone curious on where the hell Bitcoin came from and why people care.

Four Stars (Highly recommended for those interested in topic, or generally recommended for anyone)

Product Leadership: How Top Product Managers Launch Awesome Products and Build Successful Teams by Richard Banfield, Martin Eriksson, and Nate Walkingshaw

Surprisingly, there are still not many books on the important no-longer-burgeoning field of Product Management. I’ve previously reviewed the popular Marty Cagan book “Inspired”, which is a decent “Product Management 101” introduction to the field. Product Leadership is a very solid “PM 201” level course, this time focusing much more on the “management” aspect than the tactics of product development. A lot of the content in this short book is interviews with product managers about their experiences, primarily team management and cross-department collaboration.

The Startup Way: How Modern Companies Use Entrepreneurial Management to Transform Culture and Drive Long-Term Growth by Eric Ries

Eric Ries rose to prominence less for the success of his own startups, which has varied, but for codify the methodology he developed for building tech startups along the way in his 2011 classic “The Lean Startup”. Now, after years of consulting with large companies like Intuit and General Electric, he is back with this sequel, expanding upon his theories to fit the demands of big businesses.

While this book certainly isn’t as groundbreaking as his first book, it has the potential to be more impactful over the long run. It provides another take on the “business transformation” industry which is peppered with talks about how companies need to “innovate”, “become agile”, and . What Eric Ries tend to do be good at which separates him from sketchier self-promoters are two main things present in this book: provide examples and interviews from actual business and clients (not hypotheticals), and try to create a playbook method people can practically use.

The main new theory here that stood out to me is Ries’s “Innovation Accounting” method which bridges the gap between venture capitalists and traditional private research and development into a more cohesive model for turning new ideas into businesses from within an existing structure. If there’s any problem with the book it’s probably that it’s lighter on content than The Lean Startup, but I’ve seen enough organizations that could still use the advice here.

Startup CEO: A Field Guide to Scaling Up Your Business by Matt Blumberg

Author Matt Blumberg is the CEO of Return Path, an email delivery technology company, which has seen its fair share of tough times since he founded the company in 1999. Former Twitter CEO Dick Costello writes in the forward, “Most companies don’t survive that many changes in direction over that many years. Return Path, by contrast has survived and thrived…. How did they do it? By focusing on all the unglamorous bits and building a company resilient enough to weather major pivots, the occasional divestiture and (most recently) a global economic crisis).”

So Matt knows pretty well what he’s talking about when he compiles a collection of advice for aspiring entrepreneurs. It’s a great checklist of a CEO’s responsibilities (pitching internally and externally, investor relations, strategy and operations, etc.), with each area getting a concise chapter, often paired with a guest author essay who has particular expertise on the subject. This is a handy reference book for new CEOs to keep near their desk.

The Big Sleep by Raymond Chandler:

One of the surest ways to achieve immortality is to create or define something. With this first novel, Chandler founded, or at least popularized, noire as a new genre.

Like reading Shakespeare or listening to Beck, The Big Sleep can seem cliched if you don’t keep in mind that it’s the originator of its style. This detective story features all of the hallmarks of the genre: the brooding detective, gruff bureaucratic police officers, and loose women.

The story organically unfolds into unexpected complexity, which is just what one wants from a detective story. With sharp dialogue and snappy 1940s action, reading the The Big Sleep in the 21st century explains why Chandler is considered one of the great American writers of the 20th century.

Sex, Drugs, and Cocoa Puffs: A Low Culture Manifesto by Chuck Klosterman

Although this is not the first Chuck Klosterman book I’ve read, it was the first one I saw (which is not surprising considering it’s by far his best seller and largely made his career). I first came across the indelible cover photo (an image which Klosterman himself suspects played a large role in the books popularity) in the bathroom of my friends’ off-campus college house in 2010, which feels like the most appropriate and/or stereotypical place to find it.

This collection of essays, published in 2003, made an impact for living up to its subtitle. In a year when Ev Williams sold Blogger to Google, Klosterman’s writing style and topic choices are oft-cited for inspiring much of blog culture; that is, writing thoughtfully about topics considered too low-brow for academia. If you have a passion for an under-appreciated niche that you think is artistic and important and want to tell the world, Klosterman gave you a template for how to do so.

The essay topics have some common themes, including but not limited to: sex (Why did the concept of MILFs become so popular in the Internet age? Is Pamela Anderson the Marilyn Monroe of the 90s? Did John Cusack’s early movies ruin relationships by giving women unreal expectations about men?) and the definition of “cool” (people who say they dislike country music are trying too hard to be cool, cereal brand marketing are kids first taste into using external culture for self-definition, the relevance of the term “cool” in the history of Rock and why Billy Joel’s coolness void does not impact his artistic greatness).

I don’t agree with everything he claims (his stance on soccer sucking and videogames not being art are two examples), but I agree completely with the way he writes about them. He’s the broader cultural embodiment of Roger Ebert’s maxim: “It’s not what a movie is about, it’s how it is about it.”

Lastly, Klosterman wins extra kudos for this paragraph on Cheap Trick, which is, in my humble opinion, the most underrated rock band:

“Retrospectively, the unilateral Cheap Trick fixation made perfect sense: Cheap Trick was good at being cool for everybody. They rocked just hard enough to be cool to metal kids, they looked just cool enough to be New Wave, and Robin Zander had the kind of hair that semi-mature teenage girls wanted to play with. Even today, the Cheap Trick logo stands as the coolest-looking font in the history of rock.”

The Spider Network – The Wild Story of a Math Genius, a Gang of Backstabbing Bankers, and One of the Greatest Scams in Financial History by David Enrich

This incredible work of journalism covers the largest fraud in financial industry history: the infamous LIBOR manipulations of the late 2000s and early 2010s. The story centers around Tom Hayes, a man portrayed as a nearly-stereotypical introverted math nerd who naturally becomes wealthy in the financial industry because that’s precisely what quantitatively advanced people did in the 2000s if didn’t stick around in academia. Hayes’s very specific niche of the financial industry, trading financial assets based on the London Interbank Offered Rate (LIBOR), connects with him a very real, very seedy underbelly of international fraud.

The Hayes character adds an unexpected humanity to the story. As the quintessential fall guy, author Enrich does an incredible job chronicling how the bankers and brokers throughout the international financial system conspired to route fraud through Hayes in a manner that shields. What’s most special about this story is what I describe as a narrative reverse head fake. That is, without complete spoilers, the story seems to build to a too-predictable ending which makes one expect a plot twist. But there is no twist; you get exactly the ending you expect, and it’s all the more heart-wrenching because it was inevitable. His story would be tragic if he didn’t make so much damn money along the way.

Five Stars (Highly Recommend to Everyone)

The Goal – A Process of Ongoing Improvement by Eliyahu Goldratt and Jeff Cox

I hadn’t heard of The Goal until it was recommended to me by the hardware engineer at Hologram. I suspect a lot of people in my generation have not heard of it, despite it being one of the best management books I’ve read.

The Goal is a novel starring Alex Rogo, the fictional manager of a UniCo Manufacturing plant which produces unidentified widgets. When his division manager tells him he has three months to make his plant profitable or else face layoffs, and his wife leaves him for working too much, Rogo reaches out to an old professor for guidance. What ensues is an enlightenment journey to the promise land of effective management.

The core ideas are simple, yet I’ve seen first-hand way too many organizations screw up the basics. Identifying and alleviating bottlenecks in any process, while not comprehensive, are such simple steps with outsized impact that they’re routinely overlooked. Goldratt’s Theory of Constraints is a great example of a memorable heuristic that can apply to work and life.

Adaptive Markets – Financial Evolution at the Speed of Thought by Andrew Lo

Professor Lo has written the finance book I wish I could have written.

The book’s title is central to the story, but not the story entirely.

Adaptive Markets is split into thirds:

First, a history of not only the study of finance, but also neuroscience, biology, and evolutionary theory, explaining how the latter inform the former.

Second, these disparate fields of study culminate in Lo’s “Adaptive Markets” hypothesis, which is summarized by these five principles (verbatim from page 188 of the hardcover):

“1. We are neither always rational nor irrational, but we are biological entities whose features and behaviors are shaped by the forces of evolution.

2. We display behavior biases and make apparently suboptimal decisions, but we can learn from past experience and revise our heuristics in response to negative feedback.

3. We have the capacity for abstract thinking, specifically forward-looking what-if analysis; predictions about the future based on past experience; and preparation for changes in our environment. This is evolution at the speed of thought, which is different from but related to biological evolution.

4. Financial market dynamics are driven by our interactions as we behave, learn, and adapt to each other, and to the social, cultural, political, economic, and natural environments in which we live.

5. Survival is the ultimate force driving competition, innovation, and adaptation.”

The final third concludes with Lo’s analysis of the current state of the financial industry and how to improve it. Regulatory examples, such as the National Transportation Safety Board (NTSB) model, provide routes for root cause analysis without finger-pointing. The concluding chapter on financial innovation for good is the material every wannabe-investment banker should read before beginning his or her career. There is so much great intellectual content in Adaptive Markets that it’ll be one of the very few books I reread.

Between the World and Me by Ta-Nehisi Coates

Written as a biographic letter from father to son, Between the World and me is brutally insightful into the mindset of modern African Americans. Coates spends the first third of his book describing his youth on the streets of Baltimore to his son. This section is impactful, profound, and has sheering insight for white readers into how ingrained a different definition of “normal life” is for black people, as well as all the contradictory messages the world (through schools and media) send to black youth.

The second phase of the book moves the story toward Coates’s adult years, where he begins his intellectual awakening, first by exposure to new things in college, and then growing wiser by finding the conflicting ideas between the intellectuals he respects. He gains broader understanding of emotions and love as he finds his son’s mother.

This personal story is embedded in the deeper context of what Coates calls “The Struggle” and why black people must continue to beat back against societal tides which hold them back. After finishing this remarkably told parable, I don’t think I’ve “learned” anything per se, because I’m not sure a white male can really say he “learned” from something this personal and outside his life experience. But I’m left with an impression that makes me stop and think, longer and harder than I did before. For a story like this, I think that’s the minimum an author would hope to convey to me, and Coates accomplished this.

Best Book Read in the Second Half of 2017

Life and Work Principles by Ray Dalio

What Life and Work Principles has in common with my last semiannual “best book”, Stephen King’s On Writing, is that it’s a combination how-to manual and autobiography written by someone who has succeeded with the advice given.

Billionaire investor Ray Dalio lays out his rules for managing life and work in a straight-shooting list format. I’m surely biased in my feelings for this book because the advice resonates with me, I agree with nearly all of it, and the average person would disagree with my last two statements. This is also why Ray Dalio is not the average person. Most people aren’t used to describing other humans as “enemies” and worthy of metaphorical “public hangings” for failing at work (at least, I think Dalio means this metaphorically). But sometimes, when you want to do great things, there can be no wasted spacetime.

Top 15 Books Read in Five Years in Chicago

15. Zen and the Art of Motorcycle Maintenance: An Inquiry Into Values by Robert Pirsig

The only work of “fiction” cracks the list at number fifteen. I put fiction in quotes at its really a philosophical textbook intermingled with a novel about a father and son cross-country roadtrip. It’s worth noting that the author just passed away a few months ago. The New York Times obituary and retro-review of the book do it justice, and concludes with the epilogue Pirsig himself wrote for the novel:

“There is a Swedish word, kulturbärer, which can be translated as “culture-bearer” but still doesn’t mean much. It’s not a concept that has much American use, although it should have….

Culture-bearing books challenge cultural value assumptions and often do so at a time when the culture is changing in favor of their challenge. The books are not necessarily of high quality. Uncle Tom’s Cabin was no literary masterpiece but it was a culture-bearing book. It came at a time when the entire culture was about to reject slavery. People seized upon it as a portrayal of their own new values and it became an overwhelming success….

This book offers another, more serious alternative to material success. It’s not so much an alternative as an expansion of the meaning of “success” to something larger than just getting a good job and staying out of trouble. And also something larger than mere freedom. It gives a positive goal to work toward that does not confine. That is the main reason for the book’s success, I think. The whole culture happened to be looking for exactly what this book has to offer. That is the sense in which it is a culture-bearer.”

14. Bubble Logic: Or How I Learned to Stop Worrying and Learned to Love the Bull by Cliff Asness

I was hesitant to even review this because it’s a long paper (about 50 pages), and wasn’t published as a book. But it’s length just passes my threshold, and it’s such an important read that I had to share it. The author is a billionaire investor only occasionally recognized outside the financial industry. This paper, written at the height of the 1990s dot-com bubble, served as not only an accurate predictor of the bubble-burst, but a precise one. Asness’s mathematical takedown of bubble logic is swiftly and decisively deconstructs human’s poor decision making abilities. Given what we have seen in the past year in the cryptocurrency markets and in the mid-2000s real estate bubble, it’s as relevant as ever.

13. The Black Swan: The Impact of the Highly Improbable by Nassim Taleb

Taleb is a bit of a cult hero these days, and this book is what started it. While I was in college (2008-2012), this book (published in 2007) became a sensation in the financial community for its ability to not only predict the financial crisis, but provide a mathematical and philosophical framework (informed from the author’s own experience in the financial industry in the 1980s) for understanding its causes and consequences. While not everyone likes his writing style, his messages are too important to be ignored.

12. The Management Myth: Debunking Modern Business Philosophy by Matthew Stewart

This two-part tale shines a bright light on the dangerous, long-held myths about “business management”. A former management consultant recounts his own time in the industry (both at top name-brand firms and spin-off independents) and researches the history of “management theory” starting from the industrial revolution. What he finds is obvious to those least empowered to change these practices: most of traditional consulting industry theory is either outdated or was never accurate to begin with, are filled with scientism, and the real answers are much closer to social science and philosophy than business school. It’s a fantastic insider expose on an industry which exists to capitalize on people’s weaknesses inside large organizations.

11. Fooling Some of the People All of the Time: A Long Short Story by David Einhorn

Often, doing the right thing is hard. It’s even harder when “the establishment” is completely against you. David Einhorn, professional investor and unintended detective, writes his memoir of his hunt to take down corrupt and shady business loan provider Allied Capital. It covers all my favorite topics in a non-fiction story: An underdog raging against the machine, simple explanations of complex financial industry minutiae, and a detective story of real-world big business corruption. I thank David for documenting his service to society.

10. Zero to One: Notes on Startups or How to Build the Future by Peter Thiel and Blake Masters

In a brief 100-or-less pages, venture capitalist Peter Thiel and his protege succinctly convey Peter Thiel’s worldview. The books’ title has become a tech startup cliche shorthand for bringing new innovation to the world. This ranks so highly in my list as I don’t think I’ve read a book with a higher value-per-word ratio than this, so I’d recommend everyone take an evening or two to complete it.

9. Indecent Exposure: A True Story of Hollywood and Wall Street by David McClintick

When I recently reviewed another book, I wrote: “My favorite genre is probably “business epics”, a category label I just made up to cover longform biographies done of companies. The historical leaders of this genre (and some of my all-time favorite books) are Barbarians at the Gate, Indecent Exposure, and The Smartest Guys in the Room.”

Indecent Exposure is the oldest of the group and served as an inspiration for many business journalists who followed in McClintick’s footsteps. It’s the “All the President’s Men” of business dramas. It’s not short, but the true absurdity gripped me all the way through this masterpiece on the greed and egos running high-profile industries.

8. What Do You Care What Other People Think?: Further Adventures of a Curious Character by Richard Feynman

I had already read the classic “Surely You’re Joking, Mr. Feynman” in college. This spiritual sequel is a collection of fewer essays, but contains a couple of much greater emotional and intellectual impact. Specifically, there are two must-read tales: First, Feynman’s reminiscing on the last year of his wife’s life leaves an impression for its emotional honesty. Second, and the largest chunk of the book, is his now-infamous Challenger story, where Feynman uncovers and explains to the government why the space shuttle exploded after launching. These two stories, emotional and intellectual, paint a fuller picture of one of the greatest minds humanity has seen.

7. Diary of a Very Bad Year: Confessions of an Anonymous Hedge Fund Manager by Keith Gessen and n+1

Possibly the best book written on the 2008 financial crisis. Keith Gessen, a fantastic writer at n+1 magazine, serves as the everyman while interviewing a friend-of-a-friend who happens to be a professional investor during the Great Recession. Each chapter is a new interview occurring about every three months, spanning a two year period. Over the course of time, The Anonymous Hedge Fund manager educates Gessen (and by proxy, the reader) on the high-level philosophy of financial industry, and the brutality of the day-to-day workings on an industry in disarray. The concept (collecting these interviews over a long period during tumultuous times) is brilliant and the execution is flawless.

6. Antifragile: Things that Gain from Disorder by Nassim Taleb

“Wind extinguishes a candle and energizes fire.” So begins Taleb’s magnum opus (although he does have a new book coming out in 2018, so he may disagree with that description). Where his prior books highlighted problems, Antifragile moves closer to prescribing, or at least describing, solutions. I prefer not to try and summarize nuanced ideas into a one-liner. This book is for anyone who wishes to be more like fire and less like a candle (or more broadly be able to adapt and thrive in an uncertain world).

5. High Output Management by Andy Grove

As I did in my 2016 review, I’ll just repeat Ben Horowitz’s quote on this book and the amazing man behind it:

Andy himself was a legendary figure. He had grown up Jewish in Hungary during a time when the country was occupied by the Nazis and, later, by the Soviet Communists. Arriving in New York, he spoke no English and had almost no money. He enrolled himself at the City College of New York, overcame his language deficiency, and went on to get a PhD from UC Berkeley. This nonnative English speaker would then write an important textbook on semiconductors in English while working at Fairchild Semiconductor. As a result, he was considered a scientific pioneer even before helping to launch Intel in 1968, building it into the seminal technology company of the era. Later, in 1997, Time magazine would recognize his nearly impossible accomplishments and name him Man of the Year. This is in part what made High Output Management so extraordinary. Andy Grove, who built himself from nothing to run Intel, stopped what he was doing to teach us his magic. And not through some ghostwriter either — Andy wrote this book himself. What an incredible gift.

4. Born Standing Up: A Comic’s Life by Steve Martin

The best biography I’ve read since college. Much like Dave Chappelle in the early 2000s, Steve Martin stepped down from the standup comedy industry while he was still at the top of the field. But that’s not the noteworthy part. What Steve Martin conveys is the struggle required to reach greatness. The years of performing in front of empty rooms, working odd jobs to make ends meet, and grinding toward an unknown future. It’s told in a compact, straightforward style that is accessible to anyone. If you read it, just maybe it will inspire you to leave all your blood, sweat, and tears on your metaphorical field of dreams.

3. Enough: True Measures of Money, Business, and Life by John Bogle

As the founder of the sensational money management firm Vanguard, Bogle has a unique vantage point on how the financial industry is designed to stealthily steal money from the rest of society. In this concise, consumable manifesto, Bogle lays out important principles for improving our financial industries, corporate America, and our personal lives.

2. But What If We’re Wrong? Thinking About the Present As If It Were the Past by Chuck Klosterman

When I previously described Klosterman as a “cultural philosopher”, I meant that not only were the topics about pop culture, but Klosterman writes in a uniquely intelligent way that’s palatable for anyone (the closest comparison to this style I can think of is the scripts from Frasier and The Twilight Zone). The ideas discussed in “But What If We’re Wrong” are simultaneously thought-provoking, relatable, profound, and accessible.

1. Command and Control: Nuclear Weapons, the Damascus Accident, and the Illusion of Safety by Eric Schlosser

The “Illusion of Safety”, as Schlosser subtitles it, is such a profound point that it can’t be understated. As I alluded to in my review of this book, there is essentially no grander story that can be told than the true story of how humanity could have created its own nuclear apocalypse, and the slim margin of error by which we’ve avoided it thus far

This review is kept short because there aren’t enough bits in our collective computers to capture all the superlatives I’d use to describe it. I rarely find a new book that both breaks into my personal pantheon of favorites and is something that I’d recommend to everyone.

“An entire generation has been raised without experiencing the dread and anxiety of the Cold War, a conflict that lasted almost half a century and threatened to annihilate mankind. This book assumes that most of its readers know little about nuclear weapons, their inner workings, or the strategic thinking that justifies their use. I hope readers who are familiar with these subjects will nevertheless learn a new thing or two here. My own ignorance, I now realize, was profound. No great monument has been built to honor those who served during the Cold War, who risked their lives and sometimes lost them in the name of freedom. It was ordinary men and women, not just diplomats and statesmen, who helped avert a nuclear holocaust. Their courage and their sacrifices should be remembered.”

On Books – Where I’ve Changed My Mind

Overrated

  • Catching the Wolf of Wall Street – Nowadays I’d give this two stars instead of the three at the time. It’s really only interesting to those who probably saw the “Wolf of Wall Street” movie, and it’s less exciting than the first book.

Underrated

  • Work Rules: Insights From Inside Google That Will Transform How You Live and Lead – Today I would probably bump this up to four stars, as it’s got great business lessons and Google stories that anyone might find interesting. I probably only gave it three stars in an attempt to not grade too easily. During that set of reviews, I gave only one four star score.
  • Dead Companies Walking – Received four stars, but in hindsight I think the lessons on evaluating shit businesses and it’s efficient short structure make this worthy of five stars.
  • Diary of a Very Bad Year – Even for a five star book, this one is exceptionally good. It would’ve been a “Best Book of 6 months” if it wasn’t read around the same time as “Command and Control”.
  • Lolita – Gave it four stars. The writing style might make it five star-worthy and I only held back due to the subject matter.
  • The Score Takes Care of Itself – This should’ve been five stars. Walsh’s “standard of performance” concept is a framework I’ve referenced a lot since reading it.
  • Atlas Shrugged – I gave this a one star rating at the time due to its length. There are enough interesting plot points and enough minimally thought-provoking philosophy to warrant two stars.
  • The Management Myth – Was a five star but should’ve been even higher. Its philosophical lessons apply beyond the management consulting industry and generally encourage everyone to be more thoughtful individuals.
  • The Mythical Man Month – Was the lowest rated of the four stars that semi-annual post. I would move that higher now, nearly five-stars, as its an engineering management classic that I have found to be increasingly relevant as my career has continued.

Other Neutral Notes

  • Chaos Monkeys – Seemed to be the most divisive solely due to the author’s personality (which comes through in the writing style). When I gave this book five stars, I received multiple emails, texts, and Slack messages from friends saying they couldn’t/wouldn’t finish the book as the author’s pomposity overwhelmed any story he was trying to tell. While I can see where this complaint was coming from, I stand by the five star rating because I interpret the author’s stance as being a particular brand of unabashed calling-it-as-he-saw-it, and is still one of the best descriptions of Silicon Valley.
  • The Alliance by Reid Hoffman – I probably only gave this three stars and not four due to its length, but it contains some very important messages for managers of people.
  • Slaughterhouse Five – Considering this is one of my favorite works of fiction in the past five years, this deserved a longer review (the one at the time was written in a rush to get the blog post out).

Analyzing Five Years of Reading

Some Summary Stats:

Total Books Read in Five Years: 142.

This averages out to about one book every two weeks.

Average Book Review Score: 3.8

Average review score makes sense when I reflect upon the two major influencing factors: The sample of books I’ve read (and how that’s selected), and how I grade.

I typically read books that I already know I will like or have come recommended, which will naturally bias the set. The exceptions are the impromptu airport or used bookstore buys, or books that are well-known that I’ll read for the sake of having said I’ve read it (like Atlas Shrugged and Isaac Asimov’s Foundation).

Then, I try to grade using a normal distribution (where a 3/3 is “average but recommendable”) as opposed to the “letter grade” scale (where anything less than 75% is bad).

These two factors show up in the average. I’m naturally inclined to read things I already know I’ll like (which would push the average score up), but then try to consciously grade on a somewhat normal distribution (which would anchor the average around three out of five).

Number of Books Read Over Time:

Stacked Columns

Clustered Columns

Length of Books Read Over Time

Following the overall quantity numbers, the next question to come to mind was whether the lengths of the books affected the quantity read in a given time period. Since books vary by length (mostly measured by number of words), it’d really be more precise to track “words read per six months”. But since that’s not really practical, the combination of books by quantity and then estimated length per book are the next closest thing. One could also suspect that, if I were reading at a consistent pace all five years, that periods with low book quantity would be balanced by the fact that the books read were longer/had more words.

StackedColumns - Books by Length

I have only categorized books into three sizes (short, medium, and long lengths), and it’s an imprecise categorization, but it does provide some insights.

  • It’s clearly noticeable that in my first six months in Chicago reading longer books (Atlas Shrugged on the bus trip moving to Chicago) that took up most of that time.
  • The periods with the highest total quantity read were packed with many shorter books.

Fiction, Biographies, and Other Non-Fiction Split Over Time

Fiction vs Nonfiction

Most Read Authors

Below is a list of authors I read at least two books from during this time period:

  • Michael Lewis – 7
  • Nassim Taleb – 4
  • n+1 – 4
  • Chuck Klosterman – 2
  • Edge Magazine – 2
  • David Ogilvy – 2
  • George Soros – 2
  • Tyler Cowen – 2

Next is a list of authors I wanted to highlight authors who I read before moving to Chicago who also had books read in these five years.

  • Emmanuel Derman
  • Stanley Bing
  • Jordan Belfort
  • Thomas Cathcart and Daniel Klein
  • Richard Feynman
  • Russ Roberts
  • Joe Nocera
  • Bethany McLean
  • Sarah Kay

Revisiting Books Read in Five Years in Chicago

This past July marked my fifth year in Chicago. It’s an arbitrary milestone, yet feels like a natural reflection point. Upon reflecting, what stands out most to me is the wide variety of great people this city has brought into my life throughout the years.

But this is not a blog about relationships, it’s a blog about books. And many of those people have not followed my reviews all five years, so now is as good a time as any to revisit everything I’ve read since I’ve lived in Chicago.

I’ve split this reminiscing into three posts:

A full list of all the books is available in Google Sheets.

Books Read in the First Half of 2017

In putting together this set of reviews, I noticed my reading material in 2017 had some very specific patterns:

  • Biographies: Seven out of 18 books count as biographies, either of individuals or individual businesses.
  • Warren Buffett: Two books on Warren Buffett, one investing-oriented and one biography.
  • Advertising: Three books about the advertising business, including the two premiere books by ad legend David Ogilvy.
  • Sales and Marketing (excluding advertising) for Business: Three books, aside from advertising, specifically about sales and marketing, primarily for software companies.

Hopefully any of these themes or some of the other surprise recent reads are of interest to you.

Two Stars (Recommended only for those interested in the subject):

Hacking Sales – The Playbook for Building a High-Velocity Sales Machine by Max Altschuler:
Author Altschuler has taken the popular “growth hacker” term and given it a more sales-oriented bent while sharing some of its same principles. Primarily this revolves around using data and tools to quantify and operationalize the sales process. This is also the book’s weakness: It’s so tooling-centric that it’s almost certainly going to be deprecated in five years, and the abstract ideas that might hold up over time are only briefly highlighted.

Three Stars (Recommended):

Adulthood is a Myth – A Sarah Scribble’s Collection by Sarah Anderson:
I hadn’t heard of Sarah Anderson until a friend came into town and lunged toward this book at a bookstore. It’s hard to tell if the “Sarah Scribbles” webcomic-turned-print-comic speaks specifically to millennials or would’ve worked for twenty-somethings of every generation, but they’re quick and clever and can make you chuckle.

Predictable Revenue – Turn Your Business Into a Sales Machine With the $100 Million Best Practices of Salesforce.com by Aaron Ross and Marylou Taylor:

Predictable Revenue, written by a former sales leader at Salesforce, is a guide to building sales departments within businesses. It won’t apply to all companies, but it’s got enough thoughts on both structuring a sales organization and tactics for improving sales processes that it’s worth the hour or two it takes to complete.

Oxymoronica – Paradoxical Wit and Wisdom from History’s Greatest Wordsmiths by Dr. Mardy Grothe:
If you’re a sucker for witticisms like I am, or just a fan of Yogi Berra you’ll enjoy this collection of paradoxical aphorisms. I’m mostly impressed by the unique angle of this compendium. It’s one thing to compile a list of great quotes; it’s another to collect only oxymorons. I wish I was clever enough to be in this book.

Ogilvy on Advertising by David Ogilvy:
While Ogilvy’s “Confessions of an Advertising Man” is more of an autobiography, this is more like a how-to manual for advertising. Each chapter, featuring aging yet still colorful ad images, focuses on a different area of the advertising business: how to create effective ads for different mediums, managing clients, and the history of the industry. There is plenty of food for thought here for anyone trying to use advertising to grow a business, even if you have to filter for what’s still relevant in today’s technological world.

Hacking Growth – How Today’s Fastest-Growing Companies Drive Breakout Success by Sean Ellis and Morgan Brown:
Author Sean Ellis, who coined the phrase “growth hacking” and runs a company espousing its concepts, has compiled a solid foundational textbook for modern business “growth”, which distinguishes itself as a distinct discipline crossing product and marketing.

It’s split into two major parts: “The Method” defines what a “growth” department is and then how they do it. The second half of the book is the “playbook” with detailed tactics and testimonials from modern (primarily software) businesses. These methods and techniques share the general philosophy of mixing creative marketing ideas with scientifically-inspired, experiment-driven execution to generate unique results.

This combination can generate either lots of small improvements that cumulate into big impact, or that “aha” moment that provides a business’s great leap forward. Regardless of which approach ends up working for your business, “Hacking Growth” can both spark ideas to try and serve as a reference whenever you’re suffering from “business owner’s block”.

More Awesome Than Money – Four Boys and Their Heroic Quest to Save Your Privacy from Facebook by Jim Dwyer:
Diaspora was a flash in the pan attempt by four NYU students to overthrow Facebook’s monopoly on social networking by giving individuals control of their online data.

With unique, early access, journalist Jim Dwyer was able to build this story over many years and direct interactions with the young cofounders and the Silicon Valley-ites they bumped up against. Without too many spoilers, the project fizzles as the Diaspora team comes to grips with their own lack of knowledge and lack of direction. This is a tragic tale, where young, unsophisticated idealists crash against the realities of owning and building a tangible business and the sociopolitical dynamics of Silicon Valley.

Four Stars (Highly recommended for those interested in topic, or generally recommended for anyone):

End of Advertising – Why it Had to Die and the Creative Resurrection to Come by Andrew Essex:
This is a tricky one to review. Picked up due to its catchy title and my interest in advertising, it’s a pretty thin, quick read. Author Andrew Essex, a former Drogan and now head of Tribeca (known for its film festival), opines on ad-blocking technology as the killer of traditional advertising. That alone wouldn’t really warrant a four-star review, but his two insights into potential futures for the ad industry so stuck in my mind that I had to give this a four.

Those ideas are:

  1. Advertising is not compelling content which is why people hate it. If companies made entertaining, educational, or otherwise valuable content instead of “advertising”, then people would watch it. The Lego Movie is a mainstream data point.
  2. Companies/brands that used to advertise could spend that budget in better ways to build goodwill with consumers. Essex’s interesting recommendation is for companies to lead the charge in privatizing America’s failing infrastructure (at a time when government budgets are a mess). Some companies have started doing this through means like sponsoring bikesharing programs in many cities. What if your street’s pothole got filled next week, but had your bank’s logo on it? Or more boldly, if new high-speed trains connecting major cities were built, funded by McDonald’s and Coca-Cola? It’s quite likely people would welcome the new improvements to their daily commute or vacation in exchange for the Golden Arches on the side of the hyperloop.

While the first idea is increasingly well-known, I found the second one pretty novel and have been mulling on it ever since.

An alternative description of this book was also provided by the author when asked by the New York Times to pitch it: “It’s the only place where you can learn about the origins of heroin and Ivory soap and the future of the internet in one tight little 200-page package. And also, hardcover is the new black.”

The Undoing Project – A Friendship That Changed Our Minds by Michael Lewis:
Michael Lewis, probably the author I’ve read the most in the last five years, has written his best book since The Big Short. The Undoing Project documents the lives of two of the most influential social scientists of the last century: Amos Tversky and Daniel Kahneman.

Both Israeli, their forced time as youths in the military shaped their unique views on how people think about problems. Eventually they find themselves in American academia, where there work, undervalued for decades, slowly spreads through word of mouth and Tversky’s inclination to accept speaking gigs. Their work formed the basis for an entirely new field now commonly called behavioral economics, which counters the heavily mathematized theories of most of the 1900s with an emphasis on observing how people actually make decisions rather than solely theorizing about it.

Their influence can not be understated and was cemented with Kahneman’s 2002 Nobel Prize coronation (Tversky prematurely passed away in 1996). Lewis successfully captured how the youths and personalities of these two friends shaped their perspectives and enabled them to provide unique insights into the human mind and encapsulate these insights into an incredible body of work.

Confessions of an Advertising Man by David Ogilvy:
When I would read this book in coffee shops and bars, staff and strangers only occasionally recognized the name “Ogilvy”. Considering he was the leading practitioner of advertising, he should really still be household name.

I expected Confessions to be a memoir, but it’s a more of a how-to manual for working in advertising (and really any business). The writing is just like one of his ads: High value-per-word (one personal metric I use when reviewing books) and short sentences composed of articulate, yet plain speech. As mentioned in my earlier reviewed book “The End of Advertising”, some of the concepts may be outdated (no surprise given it’s fifty years old). However, every other line is quotable, highlight-able, or whatever method of bookmarking you prefer, so you should give it a skim.

1984 by George Orwell:
This is one of those “classic” works that I delayed reading because I felt like I already knew too much about it.

After completing it, my first thought was that having epic, multi-page “John Galt”-esque speeches three-quarters through must’ve been much more popular a century ago and feels really bloated today.

Despite the negative tone to the review, this is still a monumental piece, painting the image of a dystopia enforced through ubiquitous paranoia. It only receives a four, not a five, because I’m comparing it to “Brave New World”, which was shorter, was more eloquently written, and is possibly more accurate depiction of how humanity could end up in a dystopia.

Radical Candor – Be a Kick-Ass Boss Without Losing Your Humanity by Kim Scott:

This book reminded me of Reid Hoffman’s “The Alliance”, which was about the flexibility of people’s roles and tenures within modern organizations. These two have what I think are important theories that are relatively fresh in management theory, yet feel more natural to my millennial cohort and therefore less surprising or informative.

Despite feeling like I didn’t “learn” much new, per se, Kim Scott has done a terrific job codifying what good management is: Honest constructive criticism, not making work issues personal while still enabling everyone to display their personalities, and many more aspects of mixing humanity with the workplace. I’d consider Radical Candor to be required reading for anyone in position to manage people, and still recommended for anyone in a profession which requires personal interaction.

Inside the Investments of Warren Buffett – Twenty Cases by Yefei Lu:
There have been many books written about investment strategies loosely based around Buffett’s philosophies. I have not yet read a book quite like Lu’s.

He takes an interesting approach. He has taken twenty of Warren Buffett’s investments and goes through the following steps:

  1. Describe the company, including its history and how the business works.
  2. Explain what most ordinary investors would have seen when looking at that company at the period of time when Buffett was investigating it.
  3. Provide his own analysis on what the business was likely worth.
  4. Explain where Buffett was in his career at the time
  5. Ultimately show how Buffett invested in the business and why

Lu outlines these investments with the appropriate amount of financial detail (while providing appendices for those who want to look themselves) and through multiple perspectives (the typical investor and Buffett).

Lu extracts important lessons from Buffett’s body of work, many of them are often lacking from conversations about Buffett’s investment style. In particular, his strategies are not as simplistic as many think, have evolved (by necessity) over time as his fortune has grown, and that many of his opportunities in recent decades would not have been available to many individual investors.

The Complacent Class – The Self-Defeating Quest for the American Dream by Tyler Cowen:
Cowen comes out with a new book seemingly every year, and each one contains a concise thesis. “The Complacent Class” covers what I consider to be an underreported topic: The rise of complacency throughout American life.

This modern complacency is caused, according to Cowen, by two forces: the rise of bureaucracy post-world wars, and technology which makes it easier to “match” a person to their existing interests (food, friends, jobs, etc.), thereby reducing dynamism and progress in society.

The end result of this complacency is almost inevitably major shocks to the system, such as the 2008 financial crisis and the 2016 election, as systemic problems build to breaking points and violent reactions. If you are looking for explanations for the volatility of the past decade, Cowen has some intriguing theories.

Five Stars (Highly Recommend to Everyone):

Weapons of Math Destruction: How Big Data Increases Inequality and Threatens Democracy by Cathy O’Neil
What Cathy O’Neil has written here with is a public service announcement against the abusive algorithm practices in our society. It is too infrequent that an insider speaks out against the hand that has fed them. O’Neil, whose credentials include stints as a Wall Street quantitative analyst and mathematician for an advertising technology firm, calls out the most damning argument against much of the math applied in our modern world: the mathematical modeling itself is poorly implemented. This is only one of her many arguments made against the widespread abuse of math, but it’s the one that bothers me most deeply because it requires someone with a certain level of knowledge and experience such as Cathy to credibly call out poor industry practices.

The above is the broader theme of the book. The literal content is: Poorly constructed and implemented algorithms are being used to further divide our world by either unintentionally discriminating against the poor (such as job application tests and insurance companies analyzing data to deny people jobs and insurance, respectively), or more heinously profiting explicitly from the exploitation (for-profit colleges and some payday loan companies).

For potential readers who would normally shy away from anything that advertised itself as a book about math, fear not. WoMD features no equations and the problems described are understandable for everyone. While Cathy does sound the alarm on many terrible practices, she provides her own upbeat solutions where math and humanity meet.

If you read WoMD and enjoy it, or want to preview O’Neil’s writing style and topics covered, she actively blogs at MathBabe.org.

The Snowball – Warren Buffett and the Business of Life by Alice Schroeder:
The number of books written about Buffett could fill its own bookshelf. Snowball is unique among them because author Alice Schroeder had unique, authorized access to Buffett, making this as close to an autobiography as we’ll ever get on this living legend.

I delayed reading Snowball for years because I had already read so much material on Buffett before, including Roger Lowenstein’s “Buffett” biography. Lowenstein, a fantastic financial journalist, focused more on the evolution of Buffett’s fortune than his personal life. Schroeder does the inverse, focusing less on the investing and more on the making of the man.

This kind of book is generally a lay-up for a great rating: The inside scoop on one of the richest man in the world, operating out of a modest home in Omaha, Nebraska, who will be remembered more for the way he accumulated his wealth than just its size.

A Man For All Markets – From Las Vegas to Wall Street, How I Beat the Dealer and the Market by Edward Thorp:
Ed Thorp is a contender for the title of “most influential man that’s not a household name.” In this autobiography, a legend walks us through his world-changing life with the humility of a man who has come, with time, to understand the gravity of his accomplishments.

For those unaware, Thorp’s resume includes creating the groundbreaking card counting system which then broke the Las Vegas casinos (until they changed all their game rules), created the first wearable computer with Claude Shannon, and being an early acquaintance with Warren Buffett. Not a bad resume.

While the subject matter (academia, Las Vegas, and Wall Street) may not appeal to everyone, the way in which one man managed to disrupt so many fields should be inspiration for anyone.

Eccentric Orbits – The Iridium Story by John Bloom:
My favorite genre is probably “business epics”, a category label I just made up to cover longform biographies done of companies. The historical leaders of this genre (and some of my all-time favorite books) are Barbarians at the Gate, Indecent Exposure, and The Smartest Guys in the Room.

Eccentric Orbits is nearly in the same league as that triumvirate. What Eccentric Orbits doesn’t quite have, by comparison, in dramatic characters, it makes up for with (spoilers) a more uplifting ending than most business dramas.

Eccentric Orbits is the history of Iridium, which if I were to describe as a “satellite company” would be under-selling its accomplishments as the only truly global telecommunications infrastructure.

The story consists of four major parts:

  1. In the 1980s, Iridium is born from humble beginnings by a few men in a Motorola research lab in Arizona. They concoct the ambitious idea of truly worldwide telecommunications via satellites, beyond any existing cellular phone technology in remote parts of the deserts and poles of the Earth.
  2. With the engineering underway, the business and legal teams at Motorola go on an international scramble to get hundreds of countries and governments, literally covering the entire world, to allow a private company to build a worldwide communications infrastructure and surround the Earth with satellites.
  3. Macroeconomic factors and the egos of Motorola’s upper management sabotage the launch of the Iridium company and satellite system by milking it for so much money and not promoting it, nothing is left to continue to operate the business.
  4. Finally, a lone, retired businessman reading about all this in the newspaper takes it upon himself to rescue the near-bankrupt satellite company with the unexpected help of Black Entertainment Television and the Prince of Saudi Arabia.

The entire saga seems so unlikely at so many junctures, and Bloom describes it all with both parts humor and Tom Clancy-esque action. In telling the story of one just one company, the author manages to teach much about the history of technology and communications in the past century. It was certainly a story worth telling and one I recommend reading.

Best Book Read in the First Half of 2017

On Writing – A Memoir of the Craft by Stephen King:
There’s something special about someone at the top of a field writing the canonical text on how to contribute to said field. Stephen King has done that for aspiring writers.

The book is broken into multiple parts, with the first third being an autobiography of his life. He discusses his lower-middle class upbringing, his youth where he discovered comic books and horror movies which gave his art its unique flavor, his life with his wife, and his struggles with alcoholism.

The heart of the book is where King gets down to brass tacks, laying bare what he knows about being a professional writer. Some of it is technical; King espouses his disdain for overly-architected plots, adverb abuse, and many more recommendations for fiction writers. And some of it is philosophical, emphasizing that achieving greatness in writing is the same as in any field: you have to enjoy what you do, and then do it a lot.

I haven’t read any Stephen King novels before, but I may have to start. King found that he enjoyed writing at a very young age, and like many greats, quickly committed his life to his craft. I am grateful that someone who devoted his life to his craft wrote a how-to manual on a subject which is really universal.

Books Read in the Second Half of 2016

Due to a very busy start to 2017, it’s taken a couple months to play catch-up on writing the latest set of reviews. My reading material in second half of 2016 was heavily influenced by career changes throughout the year, moving into product management, marketing and analytics. For everyone who reads my book reviews looking for something novel and/or thought-provoking, there are still a couple of hopefully unexpected picks (often picked up during my random but frequent stops at local bookstores).

One Star (Not Recommended):

Growth Hacker Marketing- A Primer on the Future of PR, Marketing, and Advertising by Ryan Holiday:
I picked this up mostly due to Holiday’s online reputation as a prominent “growth hacker” blogger and marketer. This book in particular was disappointing as Holiday admits it was basically compiled from blog posts and smaller eBooks he’s already written. It’s very thin, repeats some already well-known online viral marketing tales. The target for this book really old-school marketers who haven’t figured out the digital era. For anyone in the demographic of having an active online life, Growth Hacker Marketing really doesn’t have much to teach.

Two Stars (Limited Recommendation for those interested in subject):

Straight to Hell – True Tales of Deviance, Debauchery, and Billion Dollar Deals by John LeFevre:
When I was taking finance and economics classes in college, the Goldman Sachs Elevator twitter feed was all the rage with the bankers-to-be. LeFevre was able to leverage his viral Twitter feed into a book deal, though not without controversy regarding the accuracy of the content and the author’s employment background. Straight to Hell reads like the twitter account (including excerpts from the feed). The problem is the online material lends itself better to pithy one-liners than a full-length book. Compared to “Monkey Business” and “Liars Poker”, it’s not as informative on the actual going-ons of investment banking, and the coke-and-hookers antics are less extreme than “The Wolf of Wall Street”.

Inbound Marketing – Attract, Engage, and Delight Customers Online by Brian Halligan and Dharmesh Shah: Halligan and Shah are the co-founders of Hubspot, a marketing software company that helps any company grow their business through “inbound” marketing. What this means is figuring out how to attract customers into seeking you out, instead of a company having to do paid advertising or have sales teams.

This book is Hubspot’s introductory guide into the digital techniques for inbound marketing, and it’s a disappointment. Published in 2014, much of the content is either already outdated (use the StumbleUpon browser plugin bar), oversimplified (the definition of a prospective customer funnel), or obvious (how to set up a Twitter account). I picked this up to see if it provided any insights for my work in online marketing, and while it’s not really incorrect on anything and has some ideas worth thinking over, there’s not much value here you can’t find elsewhere.

Three Stars (Recommended):

Inspired – How to Create Products Customers Love by Marty Cagan:
Purchased by my boss’s boss for the product management team at my last job (iLoan.com), Inspired seems to be one of the most popular books on the role of Product Management. Given the content, I’m a little surprised by this fact and I feel like there’s a market opportunity for a deeper guide or story about product management. Inspired works much better as an introduction to product management for the uninitiated than a textbook for teaching expert-level PM techniques to those already in it. Most of the material covers what someone who has knowledge or has worked as a PM would/should already know (the difference between “product” and “project” management, balancing tradeoffs between design, engineering, and business, customer and market research, etc). It’s also a surprisingly quick read. If you’re someone who works with product managers (as an engineer, designer, or marketer), this is a helpful read which will educate you on what these people do (or should be doing).

Winning with Data – Transform Your Culture, Empower Your People, and Shape the Future by Tomasz Tunguz and Frank Bien:
Written by the CEO of business intelligence company Looker and one of his investors, Winning With Data is clearly self-promotional. But it’s not without value. Tunguz and Bien’s brief guide to building a “data-driven” organization has a couple of novel chapters (data applied to human resources and sales departments). But for the most parts, the chapters and examples are all centered around Looker’s own customers, and the briefness of the book really make it feel like marketing material. Because of how thin it is, I’m inclined to say it should be picked up in a cheaper e-book format and read on a flight.

Traction – How Any Startup Can Achieve Explosive Customer Growth by Gabriel Weinberg and Justin Mares:
A good skim for anyone working in a startup wanting to experiment with new ideas for growing your organization. Weinberg and Mares, through dozens of interviews with entrepreneurs and marketers, have compiled a collection of diverse methods for new customer acquisition. The only catch is that they’ve done such a good job blogging their work, you can get a good chunk of the knowledge for free online!

Crossing the Chasm – Marketing and Selling Disruptive Products to Mainstream Customers by Geoffrey Moore
Considered one of the canonical books on marketing, particularly for technology products, Crossing the Chasm describes a common dilemma new companies face: How do I grow my business beyond early enthusiasts who will experiment on untested technology and into mainstream markets expecting polished products? Moore’s prescribed solution is a combination of defining a subset of the mainstream that you can land on as your “beachhead” and then what additions you need to make to your early technology to make it a complete solution to that beachhead’s problems to the point they’ll pay you for it.

The rest of the book delves into the details of the decisions that go into all of this (product development, pricing, marketing tactics) paired with numerous case studies. It’s got enough business jargon (“Positioning is a noun, not a verb”) that might turn off readers not interested in the topic. Due to originally being published in 1991, it also suffers from most aspiring tech entrepreneurs already having learned it’s insights through osmosis elsewhere. But I personally always enjoy reading the original sources.

The Death of WCW: 10th Anniversary Edition by Bryan Alvarez and R.D. Reynolds:
A lot of people in modern America forget just how popular professional wrestling was in the late 1990s, which were the peak adolescent years for my generation. And during what the industry has coined “The Monday Night Wars”, WCW became the only wrestling company, for a brief couple years, to make more money and be more popular than the now monopolistic World Wrestling Entertainment. In fact, WCW would at one point in 1997 be not only the most popular wrestling company in the world, but the single most-watched television show in all of cable television. This is a fact that seems lost on people today due to how far wrestling has fallen in pop culture. But there was a time only 15 years ago when wrestling was the most popular show on cable television.

“WCW” stands for “World Championship Wrestling”, which was a wrestling company created by media mogul Ted Turner through an acquisition of another failing wrestling business based in the American South in the late 1980s. Off the back of creative storytelling and large investments by billionaire Ted Turner, it would rise to a valuation (based on proposed acquisition offers from other media companies) of $500 million in 1999, mirroring the rise of the dot-com boom in that same era. It would turn out that the dot-com boom would lead to WCW’s bust, as a series of corporate deals led WCW to be owned by America Online (yes, AOL at one time owned a professional wrestling company), whose new public company status could not support the $60 million WCW lost in the year 2000. AOL would pull the plug on WCW by selling its assets to the WWE for a mere $3 million, a stunning plummet for a business in a year and a half.

“The Death of WCW” is a business book as much as it is a wrestling book. The overarching business lesson is that customers of any business just want a good product, and if you start sacrificing on the core quality of your offering, no other antics or promotions or salesmanship will keep them. And if things are going well, limited success will cover a lot of internal mistakes. Once business turns for the worse, the whole house of cards collapses so quickly, there is no time to wait for a rebuilding.

I first came across this book when it was originally published in 2004. This 10th anniversary edition is double the size and almost goes into too much detail of the week-to-week changes in the wrestling industry for the uninitiated. However, this is also a testament to the work Alvarez has done in thoroughly researching and documenting the story of a company who, most importantly, played a significant role in the childhoods of tens of millions of Americans in the 1990s.

Disrupted – My Misadventures in the Startup Bubble by Dan Lyons:
Dan Lyons made a name for himself with his sardonic parody of Apple’s cofounder via his blog Fake Steve Jobs. Since winding down the blogging, his career has taken a series of unexpected turns. Laid off from role as a Newsweek reporter, Dan decided to take his wordsmithing into the startup land he once covered.

The company he lands at is Hubspot. For those unaware, Hubspot is a billion dollar company which sells marketing and sales software for businesses (it’s a mix of basic website form builders, customer relationship tracking, and some other minimum odds and ends a business might need to manage its online presence).

Dan’s year there turns into a nightmare for himself and the company, and Lyon’s journalistic roots motivated him to write this scathing expose of the company and startup culture at large. Dan, in his mid-50s, has immediate cultural clash with a company staffed by twenty-somethings. I’m an old soul, so I particularly enjoyed relating to the young startup employees working for low salary but free beer and candy and team praise in the form of emails ending in exclamation points, while at the same time understanding Dan’s insight into how vapid and fleeting a culture like this is. It may be surprising if even 50% of Hubspot’s current full time employees are there five years from now, and Disrupted does an adequate job of juxtapositioning this against the employment world Dan grew up in.

On one hand, Hubspot clearly has operational issues. Specifically, it seems like they’re growing their “inbound marketing” business through traditional “outbound” sales methods of having call centers staffed with low wage phone jockeys calling up small businesses and pushing them to buy a $10,000 piece of software they may not need.

If I have any issue with this story, it’s that it does seem somewhat sour to very publicly trash a company’s reputation that did pay you for a year and hired you when you were unemployed.

However, when it came to light that Hubspot executives were using illegal means to try to hack Lyon’s life and prevent this book from getting published, the company surely deserves the public relations hit it has taken since Disrupted was published.

Four Stars (Highly recommended for those interested in topic, or generally recommended for anyone):

Seinlanguage by Jerry Seinfeld:

I found this 90’s gem in the discount bookshelf at a thrift store somewhere in the Lakeview neighborhood of Chicago. Seinlanguage is a collection of essays Jerry wrote before starting his famous sitcom, and the stories served as the basis for many of his standup routines and TV episodes. So if you’re a fan of Seinfeld (the man or the show), much of the material will be familiar, yet I found enough original bits which made me genuinely laugh out loud. Seinfeld’s legendary abilities as an observational comic have been discussed ad nauseum elsewhere, so I’ll just reiterate that his insights into human behavior or so keen, and so clearly conveyed in Seinlanguage, it’s absolutely worth the $7 it costs for a copy online.

Seven Brief Lessons on Physics by Carlo Rovelli:
One of the greatest joys in life is walking into an old, small bookstore in an unknown land with no deadlines and no worries. While in New Orleans last Autumn for a family wedding, I had a lull in between festivities where I got to walk around the city and stumbled upon Faulkner House Books, a cozy floor-to-ceiling packed store. Befitting the store where I found this book, Rovelli’s brief history of physics was a fantastic find. It’s a sub-100 page, double-spaced explanation of the major concepts of physics since Einstein. One might not expect a physicist to be so eloquent. Rovelli’s writing (likely aided for American readers by translators) is clear and clever. He’s also demonstrably a deep thinker, sprinkling philosophical thoughts throughout the physics. It was such a perfect breezy read I flew through it in one coffee shop trip and on the flight home.

Creativity Inc – Overcoming the Unseen Forces That Stand in the Way of True Inspiration by Ed Catmull and Amy Wallace:
Ed Catmull may not be a household name, but his work certainly is. As the President of Pixar since it’s inception (when the Pixar team and technology was purchased from George Lucas by Steve Jobs), Catmull and his team have had an immeasurable impact on the happiness of humanity.

This is his half-personal, half-business biography, with the book itself split into two major portions: The first half is the biography of Catmull’s childhood and education breaking into the burgeoning field of computer graphics, working for George Lucas at Lucasfilm, and then founding Pixar with the support of Steve Jobs. The second half is a collection of lessons learned over his 30+ year career at Pixar as they faced specific challenges ranging from the technological, financial, and personal.

The book this most reminded me of is the previously reviewed Ben Horowitz’s “The Hard Thing About Hard Things”. They both follow the same format described above, and it’s a format I enjoy. When it comes to “business books”, I think it’s much more meaningful if the authors take the approach of “Here are problems I faced and how I dealt with them at the time. In retrospect, I maybe should’ve done this differently,” as opposed to the direct, infomercial-ly, self-help approach of, “This is how you can make a million dollars!”

Creativity Inc is a solid read for anything interested in working in any business or creative profession.

The Song Machine – Inside the Hit Factory by John Seabrook:
I think a majority of people have an instinctual knowledge that modern mainstream music is formulaic in sound and structure. But most haven’t delved into why music all sounds the same, when it started (The Beatles certainly didn’t sound like our current pop and hip hop stars) and how it got this way.

Seabrook’s “Song Machine” unveils the history of the greatest hit song machine in musical history, as measured by quantity of Top 100 hits (only behind The Beatles), length of time (30 years), and variety of artists. The machine? Swedish record studio Cheiron Studios was founded by Denniz PoP and taken to greater heights and legendary status by his protege Max Martin.

Their resume as song makers is unprecedented, starting with the major hits for both the Backstreet Boys and N’SYNC, followed by Britney Spears, Kelly Clarkson, Usher, Avril Lavigne, Pink, Katy Perry, Ke$ha and Taylor Swift. And what made them so special was nailing the modern formula: 80s stadium rock mixed with hip-hop dance-ability and rhythm mixed with choruses that can be both sung and danced to.

Along with the mythic story of Cheiron Studios’ creation and steady growth to industry powerhouse, “Song Machine” follows the beginning of the careers for the 90s major boy bands, Rihanna, and Ke$ha, along with the colorful and volatile personalities of their managers and producers.

Overall, it’s a succinct look at the history of modern pop told through the lens of its primary rainmakers. I am always personally fascinated by stories of how a small group of people (a few guys in a recording studio in Sweden) can have an inordinate impact on culture worldwide. It is profound to think that this handful of people essentially created the soundtrack to my generation, and the legend of their music factory, with the help of this book, will not be forgotten.

Five Stars (Highly Recommend to Everyone):

Chaos Monkeys – Obscene Fortune and Random Failure in Silicon Valley by Antonio Garcia Martinez:

This book is the best representation and explanation of current Silicon Valley. Chaos Monkeys, named after a technical tool from Netflix, is a memoir of Antonio’s professional career from 2010 to 2014 which included stops at many of the brand names of the Valley: Quant at Goldman Sachs and an adtech firm, starting his own adtech company funded by Y Combinator, selling that company to Twitter, and landing at Facebook.

What stood out to me is that someone so seemingly ingrained in the system would be willing to write a tell-all, including naming names, at a still relatively young age, when he could seemingly still milk it. However, two points become apparent while reading:

  1. The easy money is not as easy, or large, as headlines make it sound.
  2. In the machine of Silicon Valley, people’s memories are short and he’ll have little trouble remaining in the system.

Since it is a memoir, the reader’s reaction to the book will largely be influenced by their perception of the author. Antonio seems like someone who is not honest in the sense of strict truth-telling, but is honest with himself and his worldviews. His own opinionatedness and outspokenness comes through clearly, as does his self-awareness.

Beyond the author’s life story, readers are treated to inside scoop on the machinations of America’s glory industry: web businesses. The acquisition dance between startups and tech giants, and the inner managerial dysfunctions of Twitter and Facebook are elaborated from Antonio’s quasi-insider vantage point.

Chaos Monkeys and Silicon Valley as a whole is well summarized in this book excerpt, surely written to be quoted in reviews such as this:

“Investors are people with more money than time.
Employees are people with more time than money.
Entrepreneurs are simply the seductive go-betweens.
Startups are business experiments performed with other people’s money.
Marketing is like sex: only losers pay for it.”

Why We Get Fat – And What to Do About It by Gary Taubes:
Nowadays the dangers of sugar and excess carbohydrates are increasingly household knowledge. This was not nearly as true in 2010 when Taubes published “Why We Get Fat”, and the knowledge contained within is still not pervasive enough in American society.

“Why We Get Fat” is essentially a slimmer, more consumable take on Taubes’ 2008 book “Good Calories, Bad Calories”. He does a concise yet convincing job of disproving many of the common theories around weight gain and loss, particularly the ideas of calories-in versus calories out (the biology and chemistry of what kinds of calories consumed does influence on fat creation/destruction), overeating and laziness as causes of obesity (anecdotal and genetic evidence says otherwise), and that socioeconomics factors cause obesity (supporting academic research from both the humanities and natural sciences can demonstrate the social/economic evidence is symptomatic, not causal, of obesity).

Next, Taubes takes the time to explain the real causes of obesity, which delves into the specifics of hormone chemistry and how the body metabolizes different sugars. Thankfully Taubes is a journalist by trade (with a graduate degree in engineering) and has the ability to make the complex readable, while providing extensive references for those requiring scientific sources.

This isn’t a diet book (though it does contain an appendix with food suggestions). It isn’t a biology textbook. It’s just a well-written, high-level read for anyone who wants to improve his or her own health.

Best Book Read in the Second Half of 2016

How Doctors Think by Jerome Groopman, M.D.:
I first started this book in 2012, when I decided to buy it on a whim during a random trip to Barnes and Noble senior year of college. A few months later, it was one of the few items I packed in my bag carried with me onto a Megabus as I moved to a new city to start a new post-college life. On that 8 hour bus ride from Columbus to Chicago, I got through a majority of the book and purposefully set it aside because I didn’t want to finish it until I was ready to write a review for it and wanted the content to be fresh in my mind when I did. A few months ago, as 2016 was ending, I was ready to revisit this book and complete it knowing it would receive my highest recommendation in this set of reviews.

How Doctors Think covers a lot of examples of one overarching theme: how do doctors make decisions? As the back cover adds, the major sub-topics include why doctors succeed in decision-making and diagnosis (where expertise comes is useful), where they make errors (where expertise and experience blinds them), and how patients can influence their doctors (emphasizing that individuals can both take control of their health while also avoiding their own set of cognitive biases).

Groopman tells a story familiar to anyone interested in economics such as myself. It’s the story behavioral economics (Nobel-winning psychologists Kahneman and Tversky are cited early in the book) and fallibility of the human mind. The author does a few things tremendously well here:

  • Apply the academic work of behavioral economics to a different domain
  • Turning intellectual questions into a narrative
  • Creating this narrative out of real world anecdotes.

It is this third bullet where How Doctors Think really makes a profound impression on the reader. It is one thing to discuss human biases in academic exercises and brain teasers. Mental errors take on a deeper meaning when the results are doctors missing cancer in someone’s body because they ignored certain symptoms, or suggesting a surgery that kills someone who didn’t need to cut open. These heart wrenching stories of debt and death in our medical system due to human error should concern everyone. Luckily, Groopman summarizes these stories with lessons and suggestions to doctors and patients for improving decision-making and ultimately healthcare. I’m not listing these lessons here because you might not internalize them without the profound emotional impact How Doctors Think conveys.