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.