The Legacy of Jack Lambert

Everyone has had some hero, or at minimum an influencer, in their life at some point. For a lot of entrepreneurs and technologists of my generation, that inspiration has been Paul Graham. The follow-up question I ask, like reading source papers referenced in an author’s bibliography, is: who was my inspiration’s inspiration?

Graham documented his heroes in an essay in 2008. This was right around the time I first started getting interested in the NFL, primarily due to a ten hour video series NFL Films created documenting the Top 100 Football Players of All Time.

It’s interesting to me that, like many men, one of Graham’s earliest heroes was an athlete.

Jack Lambert, ranked 29th on the NFL Films list of the greatest players in football history, was the middle linebacker behind the 1970s “Steel Curtain” defensive line that won four Super Bowls in six years.

The impact that those 70s Steelers had on America is slowly receding from culture, which tends to happen over time. However, the spirit of players like Lambert influenced Paul Graham who in turn influenced the modern world in ways that are hard to overstate.

Graham wrote of Lambert:

“I grew up in Pittsburgh in the 1970s. Unless you were there it’s hard to imagine how that town felt about the Steelers. Locally, all the news was bad. The steel industry was dying. But the Steelers were the best team in football—and moreover, in a way that seemed to reflect the personality of the city. They didn’t do anything fancy. They just got the job done.

Other players were more famous: Terry Bradshaw, Franco Harris, Lynn Swann. But they played offense, and you always get more attention for that. It seemed to me as a twelve year old football expert that the best of them all was Jack Lambert. And what made him so good was that he was utterly relentless. He didn’t just care about playing well; he cared almost too much. He seemed to regard it as a personal insult when someone from the other team had possession of the ball on his side of the line of scrimmage.

The suburbs of Pittsburgh in the 1970s were a pretty dull place. School was boring. All the adults around were bored with their jobs working for big companies. Everything that came to us through the mass media was (a) blandly uniform and (b) produced elsewhere. Jack Lambert was the exception. He was like nothing else I’d seen.”

Fast forward a decade later. Readers of my book reviews will notice I’ve been on a Chuck Klosterman kick, reading through his collected works. Klosterman also happened to be the narrator for Lambert’s entry into the NFL’s Top 100 of All Time list.

I paired Graham’s and Klosterman’s thoughts on Lambert together because I find it exciting and a bit amazing when two people I consider great in their separate fields both took inspiration from a seemingly unrelated third forebearer.

Below is Chuck Klosterman’s commemoration of Lambert for the NFL Network:

“Over time now there’s kind of become this understanding that small running backs have an advantage because a lot of times linebackers can’t see into the backfield. His height at middle linebacker may have been a positive in the reverse. He may have had a better view of what the offense was doing and that might explain why he seemed to be one step ahead of things. He just seemed to make every tackle.

If the best player in the middle of the field is making all of the plays on the best team, maybe this is the best defender in the league?

On a “Team of the Decade”, I don’t know even who is number two for the idea of being the middle linebacker on that roster.

He was an extremely intellectual linebacker, which I don’t think was the association with him at the time probably because he was toothless, and probably because he looked kind of like a madman. His greatest strength was his mind, so he’s like John Rambo I guess.

He was certainly the most intimidating player on a pretty intimidating team.

It’s possible that Jack Hamm was a greater outside linebacker than Jack Lambert was as a middle linebacker. But I don’t imagine opponents fearing Jack Hamm the way they would fear Lambert. Pretty much every play, the quarterback was staring directly at Lambert, who had not only this very scary appearance, but this incredibly active appearance.

Pittsburgh likes to sort of perceive itself as having a certain kind of toughness, having a certain kind of team. Lambert really represents that, and there’s never going to be a guy that replaces that in Pittsburgh. He will always be perceived as the greatest personification of what Steeler football is supposed to be like. That’s what Lambert represents: the Steelers at their highest point.”

Books Read in the First Half of 2018

As a reference, my grading scale is (without any one or two star books this time):

Three Stars: Recommended, may cover too niche a topic to get a stronger recommendation for a broad audience, is only high-level coverage of its theme, or just moderately interesting fiction.

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

Five Stars: Strongly recommended to everyone.

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

Three Stars (Recommended)

Things You Should Already Know About Dating, You F**king Idiot by Ben Schwartz and Laura Moses

I picked up this comic book off the shelf at some bookstore for two reasons. First, if I’m still going to buy any physical books, they might as well be comic books. Second, it recommendation from Justin Timberlake on the cover which reads: “This book is so funny. Read it and you’ll 100% find love–if you’re into that kinda thing…happiness or whatever.” These authors must have great agents to get a JT quote. If the title didn’t tip you off, this isn’t high-class literature, but it’s not bad for a $5 comic book satirizing millennials.

If Ignorance is Bliss, Why Aren’t There More Happy People? Smart Quotes for Dumb Times by John Lloyd and John Mitchinson:

Like Oxymoronica reviewed in 2017, If Ignorance is Bliss is a book of quotes. They’re mostly comedic and organized alphabetically by theme, starting with “Acting” and ending with “Zen”. A few select favorites below:

“Every society honors its live conformists and its dead troublemakers.” – Mignon McLaughlin, a writer for Vogue and Glamour whose two Neurotic’s Notebooks became bestsellers in the 1960s

“They say hard work never hurt anybody, but I figure why take the chance.” – Ronald Reagan

“An idea isn’t responsible for the people who believe in it.” – Don Marquis

The Curriculum – Everything You Need to Know to Be a Master of Business Arts by Gil “Stanley Bing” Schwartz

“Stanley Bing” just recently announced his resignation as the Head of Communications for CBS. The Curriculum is his most recent work of satire, formatted as a faux “curriculum” mocking business schools by offering the truth-is-stranger-than-fiction kind of advice people really talk about at work. Your personal rating for this book will probably correlate with how you feel about drinking during weekday lunches and Dr. Strangelove.

Go Figure – Things You Didn’t Know You Didn’t Know by Tom Standage

Another pocket-sized airport book, Economist editor Tom Standage has compiled about 100 one-or-two page articles on random trivia, such as how modern tropical volcanoes are still creating new islands today and humanity’s opportunity cost from all the time spent watching Gangnam Style. Recommended if you want to learn ideas for Trivial Pursuit in the form of infographics.

Girl Logic – The Genius and the Absurdity by Iliza Schlesinger

Comedian Iliza Schlesinger has had a tremendous run the past couple years, starting with being the first woman to win the TV show Last Comic Standing, followed up with four stand-up comedy specials on Netflix and now her first book. This review is probably as much about her standup as it is about this book, but they’re pretty closely related. The content of Girl Logic is pretty similar to the topics covered in her shows Elder Millenial and Confirmed Kills, with more serious personal anecdotes and a bit less, but some, comedy.

If you’re unfamiliar with Iliza, I’d recommend any and all of her Netflix comedy specials and the below half an hour talk on her book:

Immortal Life – A Soon to be True Story by Gil “Stanley Bing” Schwartz

I’ve previously written about how great an influence Stanley Bing has been on my worldview. He recently wrote his third novel, Immortal Life, which tells the tale of a trillionaire tech executive using his wealth to discover a path to mental immortality. The novel has all has all the hallmarks of a Bing book, primarily his sophomoric (meant as a compliment) way of humanizing the rich and famous.

I did not enjoy it as much as his first two novels, which I think is because Immortal Life has more of a science-fiction bent than “You Look Nice Today” and “Lloyd: What Happened”, making it a little less relatable. I read “Lloyd: What Happened” in high school and it remains one of my favorite works of fiction, deserving of its own five-star review.

Who Reads Poetry – 50 Views from Poetry Magazine edited by Fred Sasaki and Don Share

To answer the title’s implied question, I don’t really read poetry (other than The Road Not Taken which I probably misinterpret). Who Reads Poetry is published by the University of Chicago Press and is therefore heavily influenced by the Chicago/midwestern community. It includes essays from authors of various walks of life and professions (writers, military, economists, et al.), including some celebrities (Christopher Hitchens, Roger Ebert, Roxane Gay).

Probably the most memorable segment for me was when Jeffrey Brown of PBS Newshour asked two cadets in military school about why poetry is taught to soldiers.

Cadet One: “Poetry is directly related to our function as a military officer because, at the bottom level, we’re all here training to take lives. And that’s a concept that you really can’t approach without art, without some sort of deeper understanding of the human condition, which is exactly what poetry is.”

Cadet Two: “That’s a clumsy way to say that. We’re not here to take lives and destroy things. Perhaps those are the tools of the army and the military, but really we’re here to learn how to be leaders. And…poetry has a direct influence on how I think about leadership and how people view leadership.”

Fire and Fury – Inside the Trump Whitehouse by Michael Wolff

Fire and Fury got a ton of press when it was released (google it to confirm for yourself). It’s not exactly All the President’s Men (a personal all-time favorite of mine) and Wolff isn’t exactly Bob Woodward. However, it is a fun read in the sense that I don’t usually read a lot of tabloid-esque salacious kind of material.

Not to say this isn’t good reporting. It clearly has one primary source, who seems to clearly be Steve Bannon given how much attention he gets in the book (and the story ends when Bannon’s tenure did).

There are a few insights into the Trump administration I didn’t know much about going in. First, the bulk of the book is about the dynamics of three warring camps vying for Trump’s attention: The traditional Republican establishment, the far-right populist extremists led by Steve Bannon, and Trump’s family members. Second, the very significant role the Mercer family plays as Republican power-players. For these perspectives alone, this book was worth reading, and probably more so if you like following the news as entertainment.

Brotopia – Breaking up the Boys’ Club of Silicon Valley by Emily Chang

Silicon Valley has not been immune to the #metoo wave upending industries over the past couple years. If anything, Emily Chang unveils ways in which the tech community is as bad as the entertainment industry, partially attributable to technologists’ increased wealth accumulation.

My favorite part of this story is the book’s early chapters that are very well researched histories of how computer programmers and academics self-selected people (white dorky men) to be the stereotype of what a computer programmer should be because of very flimsy science and general laziness. Chang’s first couple chapters explain how the implicit misogyny of mid-century academia created an inescapable cycle for women who couldn’t be taken seriously in computer science. This opening material of Brotopia was its most informative.

The the middle chunk of Brotopia covers either a lot of stories well-known in the tech media (like Uber’s sexual discrimination and harassment issues). Aside from the varying information levels between chapters, Chang has compiled a thorough, informative summary of the too-frequent sexism in the tech industry.

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

Astrophysics for People in a Hurry by Neil DeGrasse Tyson

I picked this up at an airport and the title lives up to its name. You can pretty much knock this short read in one cross-country flight. Beginning with the “Big Bang”, it expands out to the known limits of the universe, and concludes with an overview of humanity’s tools for understanding everything in between. It’s the perfect plane read: short, to-the-point with just the right amount non-academic commentary, and will leave you feeling just a little smarter than before you left.

At the Existentialist Cafe – Freedom, Being, and Apricot Cocktails by Sarah Blakewell

“Existential” is one of those words that people abuse without knowing what it means, and only refer to when talking about when reflecting upon the insignificance of their own lives. So when Bakewell’s book got good press for being a welcoming introduction to philosophy without Wittgensteinian jargon, I had to pick it up if I wanted to pursue being an amateur philosopher myself.

At the Existentialist Cafe weaves together a story broader than I expected by putting the advancement of philosophical ideas in the 20th century against the backdrop of greater cultural history, primarily the impact World War Two had on European culture and thinking. In this way, this book is as much a biography of humanity in the 1900s as it is a textbook on existentialism. The biography part is emphasized by focusing chapters on specific individuals who led the existentialist movement, primarily lovers Jean-Paul Sartre and Simone de Beauvoir. A touch of the author’s personal journey (because phenomenology is a personal philosophy) toward a life dedicated to studying philosophy supports a casual, welcoming tone. I recommend as a solid first book on philosophy.

Jim Brown – Last Man Standing by Dave Zirin

“We always lament in the superficial media culture that there are no heroes, but that presupposes that a hero is perfect. And what the Greeks have told us for millennia is that a hero isn’t perfect. Heroism is the negotiation between a person’s strengths and weaknesses… and sometimes it’s not a negotiation. It’s a war.” – Ken Burns quote to open the book

Jim Brown is the greatest football player of all time (I stand by this even with Tom Brady’s sixth Super Bowl ring and Jerry Rice’s records). And it is a name that, while fading from memory for new generations, still resounds in sports lore.

As NFL Films states in the above highlight video, in nine-record setting seasons, Jim Brown led the league in rushing yards eight times. Brown was a three-time league MVP. He is the only runner ever to average over 100 yards per game and over 5 yards per carry for a career.

“Jim thought on Sundays, and these are his words, that he was a god. That nobody could hurt him, that nobody could touch him, that nobody was better. And he proved it every Sunday…. That so called ‘macho’, which I hate that word, but he embodies it.” – Burt Reynolds

“I played nine seasons and never missed a game and I never laid out on the football field. I might not have the greatest ability of everybody, but the one thing that stands is that when it was time to play, I was there.“ – Jim Brown

I got to meet author David Zirin at the Volumes Bookcafe in Chicago’s Wicker Park district, where he spoke about his time interviewing Brown at his home. Zirin noted that even in his 80s, Brown is an imposing figure, still moving his gigantic frame with the help of a cane which resembles a tree trunk more than a stick.

What I really love about this biography is that it’s the perfect length, not an Odysseyian-sized epic like many biographies. It’s just long enough to devote efficient chapters to the many phases of Brown’s life: His fatherless youth, his career as the greatest football player ever and the last man to lead Cleveland to a major sports championship before Lebron James, his subsequent Hollywood film career, and his subsequent life promoting black rights alongside Muhammad Ali and Malcolm X and suppressing gang violence by encouraging black youth to compete economically, not violently.

As the opening Ken Burns quote foreshadows, there is another side to all the great things Brown accomplished. Zirin devotes a chapter to Brown’s history of under-reported domestic violence against the women in his life. Sociologists today could easily say that someone like Brown is the epitome of the modern term “toxic masculinity”.

Regardless of where you fall on the spectrum on judging Brown, in a today’s time where Malcolm X and Ali are gone, there remains gravitas to Jim Brown still standing.

Powerful – Building a Culture of Freedom and Responsibility by Patty McCord

How did the DVD-by-mail startup bankrupt Blockbuster and become (as of publishing this post) a $100 billion entertainment behemoth? It’s largely attributed to the innovative culture the company developed, led by Patty McCord.

This book pairs really well with Ray Dalio’s Principles because they both pull no punches. They attribute the success of their organizations to honesty, the removing of pretense, and saying what others won’t. Powerful’s chapter titles reflect this (“Human Beings Hate Being Lied To” and “The Art of Good Good-Byes: Make Needed Changes Fast and Be a Great Place to be From”). I personally believe that if more companies should follow something closer to the Netflix model explained in Powerful, the business world would be a better place.

To get a feel for Netflix’s perspective, you can revisit the original “Culture Deck” presentation Patty created at Netflix which helped inspire this book.

The Phoenix Project – A Novel about IT, DevOps, and Helping Your Business Win by Gene Kim, Kevin Behr, and George Spafford

So many companies have moved from the “IT” department from being a cost-center to business-critical. And yet the horror stories of software products taking too long to ship and always breaking is still the norm.

In 2013, developer operations (“DevOps”) pioneers Kim, Behr, and Spafford codified what they had learned about integrating business deadlines, agile software development, and software-infrastructure-as-code into a novel. The Phoenix Project’s story and structure are based on Eli Goldratt’s The Goal (which I previously reviewed), which translated his own Theory of Constraints mixed with Toyota’s legendary manufacturing philosophies into a story that generalized to many businesses.

As I followed our protagonist Bill and his IT team at “Parts Unlimited” drowning in deadlines and marketing team demands, it reminded me of all numerous project and process failures I’ve seen in my own career. Optimistically, the happy ending and how Bill arrives there provides a generally useful template more companies should try to learn from when trying to figure out how to move faster with increased effectiveness.

Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs by John Doerr

Doerr, a legendary venture capitalist involved in Google and Twitter, has written the guide to Objectives and Key Results (OKRs), the performance management process used by many of the top technology companies (and increasingly outside computers). Measure What Matters interweaves chapters written by entrepreneurs who have used the system to success with Doerr’s practical and specific advice for how to align all employees in an organization to achieve collective goals via individual contribution.

This absolutely earns a spot in the canon of handbooks aspiring business-people must read. Without avoiding replicating the entire book here, I’d just recommend that every company without a performance management system send a copy to every employee.

Skin in the Game: Hidden Asymmetries in Daily Life by Nassim Nicholas Taleb

“Skin in the game is about honor as an existential commitment, and risk taking (a certain class of risks) as a separation between a man and machine.”

That’s the description of the book’s core concept (from page 35 of the hardcover). Primarily, Skin in the Game thoroughly explains the philosophical and tangible importance of personal risk-taking to humanity. From bankers and wantrepreneurs losing others people money and going back to their taxpayer funded beach houses or the nefariousness of wage-slavery, Taleb uncovers “asymmetries” throughout society. In other words, areas of life where people are taking more than they’re giving, and how to not be one of them.

Taleb extends this study of social asymmetry to other areas, including a fascinating chapter on minority rule (relevant for liberals who were astounded by Donald Trump’s presidential win, which Taleb essentially predicted and explains). Antifragile is still my favorite of Taleb’s books since I find its ideas even more insightful, but this is still a must-read. Taleb’s insights are still well-understood in culture, and they should be.

Five Stars (Highly Recommend to Everyone)

Bad Blood – Secrets and Lies in a Silicon Valley Startup by John Carreyou

This book comes at an important time in American culture when journalism and media is under attack. Journalist John Carreyou has given the field its best defense by uncovering the most blatant and diabolical American corporate fraud since either Bernie Madoff or Enron. The various financial institutions may have done more damage in the 2000s, but you’d be hard pressed to find a much clearer link between knowingly putting people’s health at risk for the sake of greed and fame as what happened here.

Carreyou tells the inside story of Theranos, a much-lauded biotech startup started by the psychopathic founder Elizabeth Holmes. The psychiatric accusation may seem strong until you read what she did in verbally abusing employees, hiring private investigators to watch employees at their homes, and ultimately risking people’s lives by faking and lying about blood test results from her company’s products.

It’s the kind of story I imagine splits a journalist’s psyche: it’s the kind of criminal story that makes a journalist’s career, but wouldn’t be possible without others having suffered from the crimes. Carreyou has done a tremendous humanitarian service by telling this story.

The Best Books Read in the First Half of 2018

For the first time on this blog, I am giving this nod to two books that were both so supremely written and whose stories are so intertwined that it made sense to give them both the honor.

The Gene – An Intimate History by Siddhartha Mukherjee

The Gene Cover

Siddhartha Mukherjee, a Pulitzer Prize winner, cancer physician, and professor at Columbia University, has written the canonical history of the gene. The concept of the “gene”, along with related ideas of “heredity” and “evolution”, is one of those ideas that most people are vaguely familiar with but don’t know much beyond what they can recall from high school.

Mukherjee has written the most readable and still comprehensive history of evolutionary science, focusing on the gene as its core.

Forget the science, which is taught with clarity I’ve only encountered in Feynman’s stories. The Gene is as intellectually inspiring as it is emotionally energizing. The author went into medical research and genomics to uncover the root of his family’s dark secret: everyone in his family and their local Indian village knew his family was cursed with schizophrenia, which consumed the life of his two uncles and a cousin.

The book opens with this powerful prologue:

“My father is the youngest of five brothers, and Moni is his first-born nephew–the eldest brother’s son. Since 2004, when he was forty, Moni has been confined to an institution for the mentally ill…with a diagnosis of schizophrenia. He is kept densely medicated–awash in a sea of a sorted antipsychotics and sedatives–and has an attendant watch, bathe, and feed him through the day….

Moni is not the only member of my father’s family with mental illness. Of my father’s four brothers, two–not Moni’s father, but two of Moni’s uncles–suffered from various unravelings of the mind. Madness, it turns out, has been among the Mukherjees for at least two generations, and at least part of my father’s reluctance to accept Moni’s diagnosis lies in my father’s grim recognition that some kernel of the illness may be buried, like toxic waste, in himself….

In 2009, Swedish researchers published an enormous international study, involving thousands of families and tens of thousands of men and women. By analyzing families that possessed intergenerational histories of mental illness, the study found striking evidence that bipolar disease and schizophrenia shared a strong genetic link. Some of the families described in the study possessed a crisscrossing history of mental illness achingly similar to my own: one sibling affected with schizophrenia, another with bipolar disease, an a nephew or niece who was also schizophrenic….

The study provided a strange interior solace–answering some of the questions that had so haunted my father and grandmother. But it also provoked a volley of new questions: If Moni’s illness was genetic, then why had his father and sister been spared? What “triggers” had unveiled these predispositions? How much of [Moni’s] illness arose from “nature” (i.e., genes that predisposed to mental illness) versus “nurture” (environmental triggers such as upheaval, discord, and trauma)? Might my father carry the susceptibility? Was I a carrier as well? What if I could know the precise nature of this genetic flaw? Would I test myself, or my two daughters? Would I inform them of the results? What if only one of them turned out to carry that mark?

This book is the story of the birth, growth, and future of one of the most powerful and dangerous ideas in the history of science: the ‘gene,’ the fundamental unit of heredity, and the basic unit of all biological information.”

Modern Prometheus – Editing the Human Genome with CRISPR-Cas9 by Jim Kozubek

Modern Prometheus Crispr-Cas9 Cover

For those who have heard the term “gene editing” but don’t really know much biochemistry, CRISPR-Cas9 is the technology behind one of the most important scientific revolutions of our time. Author Kozubek not only explains this innovative tool with readable scientific precision, he elevates its significance. His unique background of journalist-turned-scientist gives him the perfect skillset to tell this story.

CRISPR is an important inflection point in human evolution, enabling us to change who we are at our most fundamental genetic level. Modern Prometheus impresses this importance upon the reader by spending as much time on the political and capitalistic implications of the technology as the underlying science.

Kozubek acknowledges, with great respect, the tough choices that have been and will continue to be made by the brilliant scientists who have increasingly dangerous power over everyone not seen since the creation of the atom bomb:

“Heroism, at least as I use it in my own text, does not emphasize scientific valor as a series of achievements by right-minded people. Rather, to be a hero means to be immersed in a life-world, or lebenswelt, as the philosophers call it, to navigate complicated social, cultural and biological strata where there are no fundamentally right actions. Whereas we once had the archetype of the ‘Greek hero,’ who confronted binary decisions of whether to adhere or break with authority, the ‘Western Hero’ evolved into a pragmatic model. He knows his own moral character is not higher than his peers, but that does not stop him from enforcing justice or an ethic through a policy of pragmatism.

“In effect, to be a hero means to pursue one course of action at the expense of another course. Every ‘scientific hero’ knows he was just following one of many hypotheses and lines of thought. And, just like the valiant hero who steps into traffic to save a child, he denies it was a special act, because he is not entirely confident that he would have done it again. A genuine hero knows full well he could have easily acted otherwise.”

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.