Table of Contents
At 75 books read a year, Stephen King considers himself a slow reader. By his scale, my reading speed would be closer to a sloth. That said, I do read more than five books a year. What follows is a subset from this year that I believe would benefit any startup leader.
I don’t have any hard & fast rules on the books I read, except that I stay away from reading books in the year they were published. It’s more of a personal self-defense mechanism against FOMO than any grand vision for knowledge discovery or a quick hack to learn more. It reduces friction in my life, and that works for me.
For this list, the litmus test is very much like my previous listicle on the Openview blog: would I recommend this book to my younger self? Listed below are 2021’s recommendations and in no particular order.
Tape Sucks – Frank Slootman
If increasing shareholder value is the singular dominant metric for a CEO, Frank Slootman walks on water. He is three for three in terms of profitable exits, each exit bigger than the last. Currently the CEO of Snowflake, he has accomplished this feat by relentless focus and innate competitiveness.
About Slootman’s first exit, Tape Sucks has a candid and impatient narrative. Much like, as media articles suggest, he is in real life. The book reminds me of Lou Gerstner’s turnaround tale in Who Says Elephants Can’t Dance. Lou, while polished and direct, was notoriously impatient with cruft and other time-wasters. Tape Sucks is for the leader who, having solved product-market fit, is trying to accelerate growth.
On a side note, a book based on his essay Amp It Up will be released by Wiley in 2022.
“Big companies are stable by their own inertia: it is hard to get them to change. A startup is the polar opposite, which is both a strength and a weakness—it wants to change all the time and there is little to keep it in a groove.”
(Frank Slootman, Tape Sucks)
The Infinite Machine – Camila Russo
Ethereum, like its crypto siblings, is hot, controversial, and complex. However, the human spirit that drives those who build it hasn’t changed. The Infinite Machine is their story. It documents the startup-like movement that founder Vitalik Buterin created. At one point, everyone was living in the same house for months, racking up personal debt to find a new way to do whatever it is that Ethereum does.
The book is a play-by-play of what happened in a story that is still incomplete, and it shows. Towards the end, you can sense Russo looking for a good ending, perhaps making the book a bit longer than it needs to be. But it doesn’t take away from the revealing narrative about the people behind the movement. The book is a must-read for the leader who needs to inspire smart people to change the world.
“Visionaries like Vitalik dream of traveling to the moon and beyond, frequently underestimating the gravitational pull that mundane forces like human ambition, greed, and fear can exert. It turns out that revolutionizing financial systems may be easier than overcoming human frailty.” (Camila Russo, The Infinite Machine)
Common Stocks and Uncommon Profits – Philip A. Fisher
It would be odd to recommend a book about investing in public markets to a startup leader. However, if you look past the dense antiquated language, the book is a comprehensive view on how to look at sustainable high growth. Surprisingly looking at the financials is only a part of the puzzle; a lot of it comes to the integrity and competence of the leadership team.
Fisher advises the reader to stay away from investing in startups. Yet every startup leader must read Common Stocks and Uncommon Profits to understand what it means to be a sustainable growth company.
“There must always be a conscious and continuous effort, based on fact, not propaganda, to have employees at every level, from the most newly hired blue-collar or white-collar worker to the highest levels of management, feel that their company is a good place to work.”
(Philip A. Fisher, Common Stocks and Uncommon Profits and Other Writings)
Leadership in Turbulent Times – Doris Kearns Goodwin
All great leaders go through personal trials that, if they succeed, make them better leaders. Doris makes this case by profiling some of the transformative US Presidents in history, from Lincoln to LBJ, from Teddy Roosevelt to FDR. It is a must-read for any leader going through a personal trial, who is questioning their ambition, and unsure if they’re going to get through it.
“Scholars who have studied the development of leaders have situated resilience, the ability to sustain ambition in the face of frustration, at the heart of potential leadership growth.” (Doris Kearns Goodwin, Leadership in Turbulent Times)
The Last Thing He Told Me – Laura Dave
Set in modern-day tech hotspots, Laura Dave wastes no time sucking you into the world of her creation and yet takes her time to reveal the plotline. Her storytelling style is tight and yet evocative. In the first five minutes, you’re hooked.
Long before Austin became the white-hot Mecca for all things tech, I helped open two offices in Austin. Even back then, Austin hit every mark on the talent, tenancy, and taxation checklist. It had a seemingly endless supply of college-educated talent. Real estate was plentiful and cheap, and there were no state taxes. As Dave described the city, I found myself nodding and transported Austin’s streets and landmarks. It was a great way to revisit without leaving home.
Sometimes the only way to disconnect from your world is to get sucked into someone else’s. So this holiday break make this book your guilty pleasure. Block out your calendar, uninstall Slack, pour a beverage of your choice, and start reading. You will enjoy it.
And to my bevy of sisters-in-law who claim I read nothing fun, here is proof to the contrary.
“In one way or another, this is the deal we all sign when we love someone. For better or worse. It’s the deal we have to sign again and again to keep that love. We don’t turn away from the parts of someone we don’t want to see. However quickly or long it takes to see them.” (Laura Dave, The Last Thing He Told Me)
The Biggest Bluff – Maria Konnikova
About her quest to become poker world champion, Konnikova has written the perfect memoir. The Biggest Bluff is time-boxed, intensely personal, and focused. Her journey is a showcase on dealing with ambiguity with humility, hard work, patience, and curiosity. It is a must-read for a leader who is getting comfortable with uncertainty.
“If you’re skeptical of any prescriptive advice to begin with, if “less certainty, more inquiry” is your guiding light, not only will you listen; you will adjust. You will grow. And if that’s not self-awareness and self-discipline, I don’t know what is.”
(Maria Konnikova, The Biggest Bluff)
The Fixer – Bradley Tusk
While no Bradley Tusk, I spent the better part of a decade at the intersection of software, telecommunications, and regulatory policy. At times the hard way, I learned that to beat the incumbent, it is not enough to write excellent software that people want. And that with incumbency comes with ingrained power to perpetuate itself, especially when that power is political.
Tusk has written a book filled with stories and checklists for anyone doing anything to stir up the status quo. This book is for anyone who’s hitting regulatory headwinds and trying to make sense of the messy world of political advocacy.
“The best spin is no spin. Rather than triaging and obfuscating and boasting and attacking, just answer the question honestly, thoughtfully, and simply.”
(Bradley Tusk, The Fixer)
Finally
When I first started writing this list, I intended to limit it to 5, as it is an excellent way to instill focus. In 2021, I found this very hard to do, and hence the seven you see above. The list expansion got me thinking of another book I read last Christmas: Guy Raz’s How I Build This.
Detailed and comprehensive, Guy Raz has created an encyclopedia of business leaders from all walks of life. It breaks down the biggest myth of successful entrepreneurship: the supposed simplicity of success told from a post facto lens. It will be on my “must-read” list for years to come.
“Because while you can never fully know what you’re getting yourself into when it comes to building a business, you should at least know whether you can get yourself out of it if everything goes south. That is the difference between dangerous and scary.”
(Guy Raz, How I Built This)