Books Read in the First Half of 2020

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

Two Stars: Not recommended, except for those very interested in the subject.

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.

Themes from these six months:

  • Technologist Gene Kim: The cofounder and CTO of TripAdvisor now dedicates much of his time to writing books about how to best run technology organizations. Applicable to large companies and startups alike.
  • Uber and How We Work: As part of my research for working at Bluecrew, I delved into the temporary staffing industry, modern “gig economy” companies such as Uber, and some general history of labor.
  • N+1 Magazine: I’ve reviewed books written by the staff of literary magazine n+1 in the past, and this year I’ve added three more to that list.
  • Bill Simmons Colleagues: Simmons is best known as a founder of two successful online media brands (Grantland and The Ringer). After I learned he’s good friends with Chuck Klosterman, I’ve dived into books by more of his colleagues.
  • Adult Entertainment: The confluence of Dave Chappelle Netflix special, a new book by one of my favorite authors, working for Tinder’s parent company, and Hugh Hefner’s semi-recent death all converged into me reading a lot of material around sex. Readers are forewarned.

Two Stars

Breaking Through: Leadership Disciplines from Top Performing Staffing Firms – by Mike Cleland and Barry Asin

Read this as research for my work at Bluecrew, a subsidiary of InterActive Corp trying to disrupt the blue-collar hourly staffing industry. I was disappointed to find that half of the book is the generic advice one would find in any issue of the Harvard Business Review. There are a handful of lessons specific for those interested in the temporary staffing space, but it fails to serve as either a general business guide or a comprehensive analysis of the industry.

The Day the Bunny Died – by Victor Lownes

Little-known fact about Playboy: although the company is most well-known for the magazine, the most profitable part of the business through the 60s and 70s was its British casino business. And the man behind Playboy’s business success was Victor Lownes.

An early friend of Playboy founder Hugh Hefner, he held a variety of executive roles at the Chicago headquarters before asking Hef for the responsibility of expanding to England. Lucky timing landed him there shortly before the British government deregulated casinos, and it was Lownes’ shrewdness to associate the Playboy brand with casinos. The profits were so overwhelming, so quickly, that for a time, Lownes’ was the highest paid businessman in all of England.

There are three main problems with this autobiography: First, his overt sexualization of women, in his own words, I don’t think ages well even to the sexually liberated. Second, his chapter on his friendship with controversial director Roman Polanski would also be deemed questionable today. And lastly, it’s oozing with his own ego, which is not at all appealing except in the context of managing the casino business. Though, for anyone interested in understanding Playboy as a business, Lownes’ story is a necessity.

Three Stars:

Pimp: The Story of My Life – by Robert “Iceberg Slim” Beck

In Dave Chappelle’s standup hour The Bird Revelation, he tells a dark story implicitly comparing his time in Hollywood with being a prostitute controlled by a brutal pimp. It is this book he holds onstage and uses one of its stories to make his analogy.

Out of morbid curiosity, and as a devout Chappelle fan, I picked up a copy to see if the stories he told onstage were really in it (they are). And the depiction Chappelle gives his fans is not dark enough.

Pimp is a brutal book written by someone who lived a rough life. Iceberg, a native Chicagoan, escaped a broken home with a mom being serially abused by the men in her life. Striking out for himself as a black man in the late 1930s with no education, he learns viscerally on the streets and from older men how to break into the pimping business, and break women down in the process.

There are graduate theses written about the role Iceberg has played in our cultural understanding of pimps, its influence, and ultimately our numbness to its realities. It all stems from what is, by biography standards, a short book. But it’s a brutal one, and Beck’s honesty about himself and the life of many black people in that era is why it still resonates.

Uberland: How Algorithms are Rewriting the Rules of Work – by Alex Rosenblat

Journalist Alex Rosenblat spent years compiling this sociological study of Uber’s relationship with its drivers. She does a great job of calling Uber out as a pioneer in newspeak: a self-proclaimed “tech” company that’s a taxi service with GPS. If it were truly a tech company, it wouldn’t have had the problems making money that it’s had.

This isn’t to say Uber is evil. Rosenblatt outlines the differences between all the different constituents Uber has to keep happy, such as the heterogeneous base of part time and full time drivers. A lot of their legal and public relations issues would be handled a lot easier if Uber used software to yield decision-making over to these drivers. Of course, letting drivers set their own rates and regular customers would make the Uber entity itself less valuable.

And this is the crux of Rosenblat’s critique: Uber claims to be a software provider to its drivers, not a taxi service, and therefore the drivers are not employees. But when the Uber software dictates how much drivers make and who they can drive, the algorithms are as much of a manager as a real boss would be.

Humans as a Service: The Promise and Perils of Work in the Gig Economy – by Jeremias Adams-Prassl

Prassl’s book is way more academic than I expected, without becoming verbose or boring. His history of global employment law and economics provide great context for the debates happening today. Particularly astute is the connection between the algorithms used by companies like Doordash and Uber to manage their gig workforce and the philosophy of Frederick Winslow Taylor. The former is an even more ruthlessly efficient form of the latter, without incorporating the criticisms Taylorism has faced.

What’s helped Uber and Lyft succeed to the degree they have is because their competitor, the traditional taxi industry, was as intertwined with regulators as they are and as equally hated. This is one way in which the rideshare cases are unique from, say, house cleaner apps.

Lastly, the best critique, and why this book leans anti-tech, is because most gig economy apps call themselves “disruptors” in a misleading use of the term. Popularized by Clayton Christensen, “disrupting an industry” was about new science and engineers techniques. What these mobile apps are “disrupting” is government laws. Whether that is good or bad is up to you to decide.

The DevOps Handbook: How to Create World-Class Agility, Reliability, and Security in Technology Organizations by Gene Kim, Jez Humble, Patrick Debois, and John Willis

For the uninitiated, “DevOps” (short for “Developer Operations”) is a field of work and study that broadly covers tools and practices for how software gets coded and the process by which it can get used by customers/users. I leave that definition purposely vague because comprehensive guide compiled by experienced practitioners covers what you need to understand the core DevOps concepts.

It’s less about specific tools (although they are mentioned) than about key ideas to simultaneously improve a software team’s execution speed and safety, a seemingly impossible win-win scenario. The evidence for their ideas comes from case studies and interviews with leading technology managers at companies such as Target, where there is very real business results driven by the success or failure of their technology.

The Unicorn Project: A Novel About Developers, Digital Disruption, and Thriving in the Age of Data

It is not unusual for people to think their company is underperforming, especially when the media is filled with stories about hot tech startups or massive monopolies that seem to make everyone else look like losers. The hard part is responding: how do we improve the company we’re already in?

Gene Kim, cofounder and CTO of Tripwire, has written a sequel to his prior Phoenix Project, covering similar ground as its predecessor. Maxine, a senior software engineer unjustly blamed for another team’s software failure, is moved to another failing software team at her employer Parts Unlimited, an automotive repair and parts retail chain.

What she discovers is an underground team of technologists and a retired board director who are trying to implement new ways of working faster and smarter in hope of turning an old brick-and-mortar business into a digitized, omni-channel customer-pleasing experience. Kim captures corporate politics accurately, as a manipulative marketing executive trying to prevent the technologists from gaining power provides the necessary narrative thrust.

Unsurprisingly, the story is a little cheesy. But it’s both very relatable for anyone who has dealt with business politics, and practical for anyone who has worked around software teams that just didn’t seem to be performing as well as they should.

Four Stars

Not Pretty Enough: The Unlikely Triumph of Helen Gurley Brown – by Gerri Hershey

I don’t read Cosmopolitan, but I know what it is. Or at least I thought I did until I read the life story of HGB.

Hers was a name I’d vaguely recalled from documentaries about the middle of the last century. She was famous for two major achievements: First, writing a blockbuster book Sex and the Single Girl forty years before Carrie Bradshaw but very much an influence. Then she was able to leverage her potential one-hit wonder into an enduring role as the 35-year Editor in Chief of Cosmopolitan, remaking a fledgling fiction journal into the powerhouse women’s magazine of our lifetimes.

Gerri Hershey should possibly be most proud of is the impressive journalistic effort she’s made to unveil the complex person underneath the bubblegum glam. What lies beneath Helen is a beautifully complex mixture of childhood trauma growing up in Ozarkian poverty, an innate ambition which led to her spending her twenties in Los Angeles leading a Peggy Olsen-esque secretary-to-copywriter career, before becoming a fully-realized celebrity in Manhattan.

One of her friends said that what made Helen, her books, and Cosmo so successful was not that she wrote about sex for titillation’s sake. It was a Midwestern earnestness to give the Big Sister guidance to women everywhere that she had learn herself the hard way. As with many innovators, if her work now seems cliche, its because she made the mold from which so much of our culture is now mass-produced.

Mr. Playboy: Hugh Hefner and the American Dream – by Steven Watts

It’s hard to review a biography of someone who, until quite recently, was still a public figure (through venues like the show The Girls Next Door). Hugh Hefner and his creation, Playboy, have been omnipresent in the zeitgeist as long as I’ve been alive. What I’ve learned, unsurprisingly though, is that he was much more than the media’s depiction of him.

Watts does a tremendous job in chronicling the evolution of Hef’s complex psyche. Hefner is a man whose reputation as a polygamous womanizer was possibly caused by his first wife cheating on him. He would respond to this by creating a magazine featuring naked women whose first investor was his mother (supporting her son above all else). For my generation, he may have seemed like a socialite, yet the young Hef avoided any drugs harder than dexedrine, an early Adderall alternative to help him work on his business empire through sleepless nights. His commitment was to his business and philosophy of life, not to shallow celebrity fame.

The rocket-ship story soars from there through the 1950s and 60s. Playboy’s cultural significance and profitability are business legend. And even once its power plateaued by the end of the 60s, the sustained relevance of Playboy and Hefner in American discourse (as participants in the women’s liberation movement and AIDS epidemics as a couple examples) is a testament to how Hefner tapped into something deep and permanent about America. As author Watts concludes, how we feel about Hefner is a reflection of how we feel about ourselves.

Cubed: A Secret History of the Workplace – by Nikil Saval

Architecture is not a field I know much about. But I have worked in cubicles. When I came across Cubed during my research on how we work, and when I saw the author had written for n+1, it moved up my reading list.

I was not disappointed. Saval weaves together multiple intellectual heritages (architecture, economics, media, interior design, etc.) into a retelling of the evolution of offices. From the small, pre-Industrial offices for bookkeepers, through the Skyscraper and “office parks” revolutions, Saval explores how our innate needs for labor and art converge in the aesthetics of our workplaces. Simply put, I give Cubed high praise for telling an interesting history of office spaces, which would surely be a boring read if written by a lesser author. 

No One Man Should Have All That Power: How Rasputins Manipulate the World – by Amos Barshad

Rasputin is one of those historical figures whose name is recognizable, but most people couldn’t really recite the story of why he’s famous. Barshad, a journalist and former contributor to Grantland, pulls this shadowy persona into modern context.

Following a recap of Rasputin’s life (a possible con artist who had an unusual but very real manipulative relationship with the Czar of Russia, his wife, and their hemophiliac son), subsequent chapters explain current day examples of behind-the-scenes manipulators of power: music agents, Mexican drug lords, and political power brokers.

Although some of the later modern political chapters are a bit long and less interesting than some of the non-obvious fields, Barshad’s journalistic capabilities combined with concise storytelling are impressive. It is a brave soul who goes to meet with Putin’s assistants with the purpose of writing a book about them.

Movies and Other Things: A Collection of Questions Asked, Answered, and Illustrated – by Shea Serrano and Illustrated by Arturo Torres

Ringer writer Shea Serrano got me hooked with his “Top 15 Gangster Movie Moments” (as I am a sucker for the genre). It was through this that I discovered this new book in his straightforwardly named “…and Other Things series”.

The book is an essay collection of Serrano’s musings on movies, interspersed with comic-style illustrations. Alongside the gangster movie moments are chapters on: fixing incorrect historical Oscars awards, which films would be improved if they featured Dwayne “The Rock” Johnson, and an interview with his kids about why they like the Marvel Cinematic Universe.

Adding to the lighthearted content is a unique (to me, at least) binding and hardcover shape that sticks out on a shelf. I don’t own a coffee table, but if I did, this would be the first book on it.

Also, he purposefully buries the lede; Don Cheadle writes the closing afterword and it’s awesome.

Super Pumped: The Battle for Uber – by Mike Isaac

If you’ve followed the tech industry the past few years, much of the Uber story is well-known: Co-founder Travis Kalanick takes his friend’s idea (with permission) for ordering cars from an app and turns it into one of the iconic companies of the 2010s. He accomplishes this essentially through a disregard for people: misclassifying the employment status of drivers, supporting a culture of the kind of “tech bro toxic masculinity” that wouldn’t have to be a cliche buzzword if Uber employees didn’t embody it, and wasting billions of dollars of investor and eventually public money.

Much of what I just wrote is not news and comprises the first half of the book. So some readers might be tempted to cast this aside after an hour if they haven’t learned anything.

It’s in the second half where Isaac’s journalism shines. As Uber’s internal cultural issues leak, the “battle for Uber” occurs between the investors trying to redeem the money they’ve invested in Uber and Travis, detached from the reality that he’s flying his company into a cliff. Isaac’s inside sources got him access to never-before-seen documents that are a testament to both his ability to cultivate relationships, protect sources, and the dysfunction at Uber.

As I suggested earlier, the first half may seem like a slow retelling of old news. The second half was an adrenaline rush I had to finish in one sitting.

Whistleblower: My Journey to Silicon Valley and Fight for Justice at Uber – by Susan Fowler

Fowler exploded into the tech world’s consciousness in 2017 with her bombshell blog post “Reflecting on One Very Strange Year at Uber”, chronicling Uber’s self-destructive culture of misogyny and abuse, ultimately leading to the CEO’s dismissal.

This book (which is, important to note, not her first since she had previously published a software engineering textbook) expands upon the Uber blogpost with her backstory, and the events that happened following the post.

In fact, she does not get to Uber until halfway through her story, which chronicles her unglamorous homeschooled childhood in the Arizona desert and her stint in academia which she purposefully cuts short after her sexist experiences with colleagues in her pursuit of a physics Phd. These earlier stories are crucial for understanding why she ultimately wrote her Uber blog, and is emblematic of so many public outcries occurring in the current culture: when people have been proverbially stepped on and felt discarded for so long, the psychological buildup is going to cause an explosive pushback.

Whistleblower pairs well with Edward Snowden’s Permanent Record (reviewed last year), as they’re similar stories written in similar styles; they slowly build to a quick, chaotic climax when their lifetime of preparation converges with the right moment in history. Is it perhaps a bit hagiographic by the authors? Sure, but that doesn’t make it any less true. I and many others have come to the similar breaking points Fowler describes, and she conveys the important psychology of a whistleblower well.

Uncanny Valley: A Memoir – by Anna Weiner

Anna’s story is a relatable one for many people I know: an intelligent, educated, English major millennial takes her stab at breaking into the book and media industry in NYC only to find it underpaying and overly-elitist. Thus, in the pursuit of being able to pay her bills, she crosses the country to Silicon Valley, a land she knows little about except that some of her college connections were able to make a living being funded by the tech industry.

What ensues, and what she chronicles with an incisive touch, is her wanderings through some of tech world’s hottest startups (Mixpanel and Github) as a non-computer programmer. Which in her case meant copywriting and customer support, people-facing roles often assigned to women and minorities to undermine their voices. “Instead of being an artificial intelligence, I was an intelligent artifice, listening comfortingly” is one of my favorite astute aphorisms.

Having taken Wall Street’s crown as the money-making outlet for the young and ambitious, she fairly skewers the institutions which give vast responsibility to inexperienced and uncaring company founders who are developing their moral reasoning at the same time they are given control of employee’s livelihoods. 

She does not name any companies or many prominent power players she comes across. For the insider, you’ll still know who she is talking about, and for the uninitiated, it’ll likely give a dual sensation of mystique and interchangeability, as all the important-sounding-people are more of a hivemind than they typically admit. 

When someone asks me what tech startup culture is like, this is the book I recommend (alongside Antonio Garcia-Martinez’s Chaos Monkeys).

Someone Who Will Love You in All Your Damaged Glory: Stories – by Raphael Bob-Waksberg

From the creator of my favorite Netflix original Bojack Horseman comes a set of short stories all revolving around relationships. 

Raphael illustrates well the wide variety of relationships in our lives. Many are not strictly romantic: “Rufus” (about the relationship of humans and dogs told from the perspective of the dog) and “These Are Facts” (on the complexities of step-siblings who don’t understand why one kid might like their father and the other doesn’t) were two of the hardest hitting stories, and I have neither step-siblings nor an affinity for dogs.

However, the heart of the book is romance, and mostly failures. “Lunch with the Person Who Dumped You” and “Lies We Told Each Other” are such sharp, relatable observations of human nature that they don’t feel like fiction.

Bob-Waksberg has an incredible gift: Other than Soprano’s David Chase and Mad Men’s Matthew Weiner (and their writing teams), there are very few others with a philosopher’s insight into our animalistic nature, a comedian’s levity about this fact, and a dramatic writer’s ability to turn realities into narrative. The best collection of short stories I’ve read.

The Player’s Ball: A Genius, a Con Man, and the Secret History of the Internet’s Rise – by David Kushner

David Kushner wrote my favorite book of all time which I read 15 years ago (Masters of Doom, which I haven’t reviewed but blogged about once). Then last year I started working for a subsidiary of InterActive Corp, the longtime owner of So when I saw David Kushner had written about the founder of, I considered it a must-read.

I was not disappointed. Kushner continues to nail his niche, telling the true stories from the shadowy or less glamorous, yet highly lucrative, sectors of the technology revolution.

At the time dot-com entrepreneur Gary Kremen started the website, he purchased the name as well. Unbeknownst to him, a con artist by the name Stephen Cohen had swept in and convinced the internet gatekeepers that he was the owner of

What unfolds is a cross between Skinemax and Catch Me If You Can. Kremen attempts to use his matchmaking wealth to reclaim his rightful ownership of, while Cohen hustles around the world with his growing pornography empire.

Without spoilers, these very real events take on bizarre, Breaking Bad-esque turns. In the category of “truth is stranger than fiction”, Kushner captures the characters perfectly and keeps the adrenaline pumping.

Five Stars

A Terrible Country: A Novel – by Keith Gessen

In college, I took a quarter of Russian 101 after reading a prediction that Russia would have a resurgence in the 2010s (and my degree required four credits of foreign language classes). It was tough and I was ill that quarter, so I ultimately bailed back to Spanish as many Americans tend to do. But even sitting in that room with the Eastern European teaching assistants and eccentric classmates taught me a lot about this literally and figuratively foreign culture. Keith Gessen’s A Terrible Country has given me a new lesson.

Gessen, who wrote one of my top ten favorite books I’ve read since moving to Chicago, fictionalized his experience as a Russian-America intellectual trapped between two worlds. 

Our protagonist, Andrei, is a Russian descendant slumming his way through American academia as a post-doc when his brother in Moscow requests his assistance caring for their dementia-struck grandmother. A short stint turns into a one-year tour of his family’s homeland.

One year away from home, living in an ancestral land, forces Andrei to confront his notions of what it means to identify oneself with a land or culture. The struggle between socialism and capitalism can’t be easily settled in one’s mind. His hodgepodge of Russian acquaintances don’t make this internal dialogue any lighter. This underlying conflict throughout the book is the title’s subtext: Is it Russia or America which is the terrible country? 

A New York Times reviewer captured the mood perfectly, as it’s written with “plenty of self-deprecation, but we aren’t given much reason to assume this is parody.” The subtext seems to be that these are thoughts and feelings with which Gessen himself struggles. We all would be better off if we all had, or better yet expressed, the complexity of Keith Gessen.

Dear Committee Members: A Novel – by Julie Schumacher

Many of us are familiar with the degrading process of asking a teacher or boss for a letter of recommendation. If it makes you feel any better, most of them don’t enjoy the rigamarole any more than you do.

Professor Jason Fitger, a literature professor at the fictional Payne University, is such a teacher. Disgruntled by his departments dwindling budget, his ex-wife, his own writer’s block, his nagging students, and his jaded disposition, Fitger spends all his working hours writing reference letters.

Therein lies the story’s gimmick; every chapter is itself a letter of recommendation. Some to students applying to grad school, some to colleagues looking for promotions, all slowly torturing Fitger via bureaucratic boredom.

I suspect most readers will find at least one of the letters relatable, for we’ve all at some point felt stuck in a dead-end situation (perhaps quarantining at home). For that dark reason, I think it’s the funniest novel I’ve ever read.

Best Book Read in the First Half of 2020

Skunk Works: A Personal Memoir of My Years at Lockheed – by Ben Rich and Leo Janos

Much like mythology, I had heard of the “Skunk Works” before I ever really knew the story. The phrase has become a bit of business and engineering legend, harkening back to a time in history fewer people remember firsthand.

The term, now synonymous with “secret research lab funded by a private corporation”, has expanded its origin. Founded in 1943, the Skunk Works was Lockheed Martin’s secret intellectual weapon against the Cold War-era Soviet Union. This book tells two primary stories: author Ben Rich retelling the Skunk Works origin story under its founder Kelly Johnson, and Rich’s own time at the helm once Johnson passed the torch.

Across the two reigns came some of the most important engineering advancements in history, particularly the U-2 spy plane and F-117 “stealth fighter”. Lockheed’s introduction of stealth technology could arguably be the leading reason why the United States was able to win the Cold War, and thus one of the most important engineering teams in American history.

Interspersed between the tech talk are interviews and essays by those around Rich during the war: presidential cabinet members, military brass, and Rich’s engineers. I don’t recall reading a memoir that’s half autobiographical and half-written by observers. I hope to see more of them.

As much as this is an excellent engineering story, it’s also a deeply American one. The growing vitriol in social discourse is depressing all around. However, when modern politicians talk about returning America to its alleged glory days, the Skunk Works story is the best version of what they mean. It was a time when America had principles it stood for that could be honestly and intelligently defended. And the defenders, protectors, and ultimate embodiment of those values were scientists and engineers at the Skunk Works who won a war with their intellect and work ethic. That is an American spirit we should all support.