Table of Contents
“Unprecedented,” “never before,” “for the first time” are some of the terms used when describing current times. But when every unforeseen event is catastrophic and every catastrophe is unique, one has to wonder if things are really that bad or if our frames of reference are unformed. The answers to this and other questions fed my 2022 reading queue and the recommendations on this list. 2022’s recommendations include a historical narrative by a non-historian, a treatise on risk, a freedom fighter’s autobiography, and two homages to contrarianism and decentralization.
Against the Gods — Peter L Bernstein
The current market is laying bare many startups’ risk management abilities. Some have already flamed out, some are barely staying afloat, and some are going to make it. More than gumption, the ones that do make it will be the ones that can manage and respond to risk.
Against the Gods is the story of risk.
Historians, Napoleon once said, must persuade. Bernstein convinces us to look at risk as being as inevitable as the human experience. By tracing the story of uncertainty and mankind’s attempts to deal with it, he challenges us to treat risk management as necessary for agency and self-determination.
In a world where a whole new generation is claiming “This has never happened before,” here is a book that shows that the answers are all around us.
Without the venturesome, the world would turn a lot more slowly. Think of what life would be like if everyone were phobic about lightning, flying in airplanes, or investing in startup companies. We are indeed fortunate that human beings differ in their appetite for risk.
The Changing World Order — Ray Dalio
We like our movies in 8k gorgeous tones, our thoughts in 160-character tweets. The public debate that Dalio’s latest work incites is a classic example of this mismatch. Almost every tweet, for or against the book, doesn’t capture the nuanced argument that Dalio makes. If a tweet would do, then I suspect Dalio would have just done that instead of writing a 400-page book.
Dalio isn’t a politician, a bureaucrat, a statesman, or a historian. He is one of the best macroinvestors in history. And until he stepped down this year was spending $100 million a year to manage $140 billion in funds. When he writes a story about international trends that you don’t like, you have to ask yourself what he knows that you don’t.
If there is any similarity between Dalio and the startup leader, it is that both are deploying capital. Dalio’s world view is important, as it shows that you have to build a framework, even if the information is incomplete or unverified. One can be forgiven for not having enough information, but indecision is inexcusable.
The most painful lesson that was repeatedly hammered home is that you can never be sure of anything: there are always risks out there that can hurt you badly, even in the seemingly safest of bets, so it’s always best to assume you’re missing something.
No Rules Rules — Reed Hastings and Erin Meyer
Netflix is iconic. In this book, Hastings and Meyer remove the aura of magic and break down the simple decisions that allow Netflix to make magic. If you’re building for the long term, this is a book you must read. Fair warning: what the authors share is simple, but by their own admission, it is not easy.
Dispersed decision-making can only work with high talent density and unusual amounts of organizational transparency. Without these elements, the entire premise backfires.
Proof of Stake — Vitalik Buterin
Changing from “Proof of Work” to “Proof of Stake” is the biggest change that’s happened to Ethereum this year. In this collection of his writings, Buterin unpacks the complex technical, social, and moral issues that drove the change. He discusses the issues that have to be resolved if open-source cryptographic platforms are to become commonplace.
Visionary founders are great at clarifying complex causal models, and Buterin shows great finesse when explaining his. He is trying to build an adaptable system for an imperfect world. This book shows him as a pragmatic, mission-oriented leader of one of the most important “startups” in the world. He displays a nuanced world view that not even his most acerbic detractors or blind followers give him credit for.
In the long tail, blockchains are not necessary; they are convenient. They are simply marginally better than the next available tool for the job. And yet, because these applications are much more mainstream and can benefit hundreds of millions of users, the total gain to society (which can be seen from the area on the above chart) is much larger.
Originals — Adam Grant
A startup leader is a contrarian, making bets against naysayers, the status quo, and perhaps their own doubts. Grant’s book makes it OK to be one. If you need a shot in the arm to continue on a path, or to bet on yourself, this is the book to read.
They practice brutal, nonhierarchical honesty. And they act in the face of risk, because their fear of not succeeding exceeds their fear of failing.
The Outsiders — William Thorndike
Tough times show you what’s superfluous and what matters. Fancy offices, titles, retreats? Not so much. Treating your employees well and focusing on the customer? Yes. It sounds simple, but it’s common in good times to lose sight of what’s important. Taking time to treat your employees well is better than fighting bad Glassdoor reviews. Spending on R&D is more important than executive off-sites. And shipping products is more important than managing PR.
This book is a collection of CEO profiles who did just that but in good times and bad. They somehow knew how to resist the temptation to shoot from the hip. They were measured, quantitative, and intuitive. And most of all, they somehow knew what mattered.
Any business leader, at a startup or not, can learn from them.
They were generally frugal (often legendarily so) and humble, analytical, and understated. They were devoted to their families, often leaving the office early to attend school events. They did not typically relish the outward-facing part of the CEO role. They did not give chamber of commerce speeches, and they did not attend Davos.
One From Many — Dee Hock
One of the many projects I worked on this year was to help a rapidly growing team expand without losing what it is that makes them special. The research took me down many rabbit holes, and at the end of one I chanced on Dee Hock, his personal story, and how it was intertwined with the rise of Visa.
In a world before dialup connections, when a merchant had to call a number to confirm your good credit, Dee managed to create a self-sustaining and self-scaling organization where “mistakes died a quick death and good ideas spread like wildfire.”
The book is a reminder that a mature bureaucracy is a minimal one, and one that finds the balance between chaos and order.
There is nothing more difficult to take in hand, more perilous to conduct or more uncertain in its success, than to take the lead in the introduction of a new order of things.
High Output Management — Andy Grove
In 1997, Andy Grove was Time Magazine’s Man of the Year, and rightfully so. During his tenure, he made Intel the global chip juggernaut. The way Intel ran its organization was and continues to be folklore. I still run into Intel alumni who speak glowingly about working at Intel and the accountability, respect, and camaraderie it engendered. Today Intel, while on a path of recovery, is a shadow of its glory days. Yet, Andy’s tome toward management as a science and his message of sweating the details is as relevant as ever.
To use your calendar as a production-planning tool, you must accept responsibility for two things: 1. You should move toward the active use of your calendar, taking the initiative to fill the holes between the time-critical events with non-time-critical though necessary activities. 2. You should say “no” at the outset to work beyond your capacity to handle.
Long Walk to Freedom — Nelson Mandela
There are endeavors that take lifetimes. Creating a company can be one such endeavor. It however pales in comparison to fighting for one’s own freedom, let alone that of an entire race. Mandela’s story is for the startup leader doubting their mission, wondering if the success is in sight, or if time will ever vindicate them. The activity is relentless and with no respite, requiring the protagonist to dig deep and keep moving forward.
I never seriously considered the possibility that I would not emerge from prison one day. I never thought that a life sentence truly meant life and that I would die behind bars. Perhaps I was denying this prospect because it was too unpleasant to contemplate. But I always knew that someday I would once again feel the grass under my feet and walk in the sunshine as a free man.
The Housekeeper and The Professor — Yoko Ogawa
Speaking of time, here’s a work of fiction about building relationships through time, math, and baseball. There is no hidden theme that reveals how to build your idea or scale your company. It is not a leadership tome. It’s a simple human story about the unlikely friendship between a math professor and a housekeeper and her son. It is a tale of caring and staying in the moment, and sometimes that’s plenty.
Eternal truths are ultimately invisible, and you won’t find them in material things or natural phenomena, or even in human emotions. Mathematics, however, can illuminate them, can give them expression—in fact, nothing can prevent it from doing so.
This Is Personal
A litle about the two rules I followed to build this list: one to help myself and the other to respect my audience.
The No-FOMO Rule
As I’ve said before, I have serious FOMO around books. For many years, I clicked “Buy” on any new book that got released, and it would sit on a dedicated shelf along with other books in my reading queue. So, I came up with a rule: Never read a book the year it comes out. It’s not an absolute rule, and I do make exceptions, but only after much deliberation. Given the frenetic pace of life and the FOMO around other aspirations, a rule that conquers one is a great place to be.
The Respect-the-Audience Rule
Who the list is for matters: a time-crunched startup leader. This automatically disqualifies the Pulitzer Prize–winning memoir of Katherine Graham, the very engaging and honest memoir of Michelle Obama, and Andrew Roberts’ persuasive biography of Napoleon. Each of these books is a great read and one that I’d highly recommend if you have the time (or inclination). But a startup leader is a different beast. She must find time to read short-form tweets and long-form books, all to keep her business alive and herself relevant. So is Graham’s biography a gem in describing a rich life borne out of resilience? Yes. Is Michelle Obama’s effortless candor inspiring? Yes. Is Andrew Roberts’ portrayal of Napoleon both inspiring and cautionary? Yes. This audience filter, however, automatically precludes these and other riveting but irrelevant reads.
Finally
We all need mentors. In fact, the older we are, the greater the need for diverse mentors from interesting backgrounds and different fields. Books, for me, are a great source of such mentorship. Though the tenets of leadership are simple and self-evident, you have to continue reading exhaustively and extensively, even if it’s just to remind you of what you already know.
Happy reading!