Three factors democratize society: technology, legislation, and periods of duress. This year, we have witnessed the effects of each.

In August of 1965, Section 2 of the Voting Rights Act prohibited the infringement, denial, or delay of the right to vote in American elections nationwide. No longer would African-American voters in the South be tasked with literacy tests, puzzles, or memory exams. When President Johnson signed the legislation, it came to the rescue of women like my grandmother. A well-educated woman, she could read and write and calculate. And yet my grandmother cast her first vote for President in 1968 at the age of 44. Until Section 2 was passed in 1965, her own state’s laws and practices prevented her liberty. By then, she’d had all six of her children; two were in college. The Voting Rights Act made it possible for her to safely travel to her local polling station and cast her vote. The simple act of electing one’s government emboldened my grandmother, Dorothy Smith. Legislation democratized citizenship in the American South.

In April of 2003, Jack Ma’s fledgling Alibaba was faced with a crisis. China’s annual Canton Fair was severely hindered thanks to a dangerous SARS epidemic. The year prior, the Canton Fair featured 135,000 exhibitors and $19.7 billion in business-to-business goods traded. This particular year, the fair saw an 85% drop in attendance with just $3.8 billion traded. Ma determined that it was in Alibaba’s interest to attend the event but it did not meet the management’s revenue expectations.

Ma used the pandemic to directly address two concerns. Ebay was beginning to encroach on Alibaba’s growth. Through the frustrations of that year’s Canton Fair, Ma understood that too much of commerce was dependent on traditional retail channels. In that eight days of quarantine, the Alibaba team engineered the solution. Alibaba launched Taobao, its peer-to-peer marketplace, and Alipay. The two systems remain pivotal to the corporation’s growth to this day. This moved Ma’s original vision for Alibaba away from a traditional B2B company and towards the marketplace of today.[1]

In just two years, China’s eCommerce ecosystem outflanked America’s. Ma is to thank for this. A period of duress democratized commerce in the Guangzhou region of China and then its entire nation.

In January of 2020, Hal Lawton decided to take on a unique challenge. When Lawton left Macy’s to lead Tractor Supply, it was to snide remarks and laughter. But what Lawton has accomplished since January of 2020 has been nothing short of remarkable. The nation’s largest rural lifestyle retailer increased third quarter revenue from $122.1 million in 2019 to $190.6 million in 2020.

Tractor Supply made fast delivery to rural customers a priority by working with Roadie, a same-day delivery service. With the partnership, Lawton scaled same-day delivery from 20% to 100% of Tractor Supply’s stores. In doing so, Tractor Supply gained an advantage over Amazon, Home Depot, Lowe’s, and Walmart. Last-mile availability proved that online retail wasn’t for urban America alone. Rural citizens now have access to many of the supplies and practices that urban and suburban homeowners take for granted. Technology democratized retail in the rural United States.

The New Digital Electorate

At the core of democratization is the work of making difficult tasks simpler. The act of democratization turns the impossible into the ordinary and the undesirable into the customary. Technology, catastrophe, and (often-divisive) legislation have long played a role in the progress that arises out of moments like the ones we’re in. With each passing year, we see more of these examples. In 2020, all three converged at once. And in each case, a direct-to-consumer philosophy was at its core.

With a pandemic raging on, citizens voted by mail from the comforts of their homes. For a number of reasons that will not be covered here, this translated into a shifting electorate. More Americans voted than ever, thanks in part to this cycle’s emphasis on mail-in ballots to promote safety, voter participation, and ease. Forward-thinking legislation produced a solution for a period of duress.

These disparate worlds intersect.

At the same time, digital-first technologies like Zoom, Amazon, Netflix, OpenDoor, Instacart, Carvana, and Shopify expanded their roles in daily American life. Like voting rights legislation, these technologies produced a solution during a period of duress. These disparate worlds intersect.

We are beginning to see the early signs of a shifting electorate that will be influenced by digital real estate more than its physical counterpart. According to a report in July 2020 that referenced the response to the COVID-19 outbreak, Pew Research Center noted that 22% of US adults have changed their residence or personally know of someone who did.[2]

As students continue to distance learn and adults shift to remote work, the household becomes a secondary location for education and occupation rather than a respite from it. The largest technology companies in America have built employment strategies around this new normal. Meanwhile, the largest entertainment companies are building direct-to-consumer strategies to reach customers where they are: in the home. Local governments are already competing for new citizens while working to retain the existing ones.

To attract a new generation of Tulsans, the city launched a  philanthropy-funded incentive scheme in November 2018. The program, Tulsa Remote, awards $10,000 grants to digital nomads who land in Tulsa and stay for at least a year. Along with the cash, the George Kaiser Family Foundation provides amenities like co-working space, and a connection to a thriving (and growing) domestic ex-pat community. [4]

The shift to online education, remote work, gaming, live conferencing, and leisure is a new form of agglomeration. A leading indicator, consumers have contributed to the first period of inflation for electronic products in over a decade. Over quarantine, these purchases provided gateways to work, socialization, and play. But if these behaviors become more permanent, cities will struggle to account for them. [3]

What may we observe over the next five to 10 years as a result? The United States may see a complete reconfiguration of states that were once reliably “blue” or “red” as urbanites migrate upstate or out of state. Or retirees will take advantage of incentivized urban living. Americans have become less reliant on their physical surroundings for community, work, education, and entertainment. And our post-vaccination future will still reflect the lingering changes caused by this year-long season of democratization. One thing is for certain: agglomeration is no longer a physical manifest of human resources, housing, and retail. Agglomeration is digital now. And that means that where we live follows our virtual loyalties and not our physical ones.

The second-order effect of the mass adoption of streaming and remote technologies is a digital electorate that may be unpredictable for quite some time. The American political industrial complex will have new behaviors to account for.

By Web Smith | Art: Alex Remy | About 2PM 

When I published this, I knew that it would be of the most tumultuous weeks in America’s recent history. As such, I decided to take a different approach to this week’s memo. Though there remains political uncertainty, there is still an opportunity to invest in foundational education. By November’s end, things will again resemble our new normal. Colleagues will return to Zoom conferences and children will finish up their fall semesters. Millions of service workers, public servants, and other essential personnel will have carried on as if America’s federal elections were any regular week.

So I chose to focus on something more foundational than the analyses of modern commerce trends, digital agglomeration, or the historical context behind the evolutions of our industries. Thanks to countless conversations with 2PM’s varied community over the past year, a number of books have been shared with or by me. The texts are diverse in their subjects, their agendas, and their authors.

Upon reviewing the 50 or so books or documents that I have read or reread in 2020, these are the 20 that made the greatest impact. I took copious notes for my own consumption. The notes allowed me to synthesize different ideas, the motivations of different people, and the durability of ideas throughout different decades. I found that the ideals were more similar than not, history often rhymed, and we have more in common than we would like to believe.

This is an eclectic list, yes, but it is a beneficial one. You may snicker at some, you may glaze over others. That’s by design; read them anyway. Learning how others understand their own worlds is a skillset that we could use a bit more of. In David Epstein’s Range, a book on the practice of generalism, he wrote:

The more varied your training is, the better able you’ll be to apply your skills flexibly to situations you haven’t seen.

Or consider this one-liner from a 2018 Harvard Business Review article:

Many studies have found that the best ideas emerge from combining insights from fields that don’t seem connected. [1]

But frankly, while there is a professional advantage to consuming this collection, most of the advantage will be more personal. Commit to reading this list and you’ll gain the advantage of context. You’ll better understand those next to you. You will be able to empathize more with those who you’ve never worked with, lived beside, or voted with. So without further adieu, here are the 20 books to read heading into 2021 and why they are relevant.

High Output Management — The walk from Shopify CEO Tobi Lutke’s office takes you down a set of stairs in the Ottawa headquarters. On the way down, you’ll pass a little bookshelf with texts that you can take, borrow, or give. I was late to reading Andrew Grove’s legendary book on management, but it’s worth it. The copy that I keep was gifted by one of the public market’s finest CEOs. The book itself is a must-read. Authored by the former chairman and CEO of Intel, the book explains a number of key management strategies, including leverage in the gathering of information, decision making, and the “nudging” of others.

Zero to One — The irony of my first visit to Silicon Valley was that it was for a launch event hosted by prolific angel investor Jason Calcanis. At the end of the event, another successful investor was signing the inside covers of his new book. Back then, I didn’t know much about Peter Thiel beyond his contributions to Paypal and his Facebook investment. But for anyone building anything, the book is a must. He’s an unparalleled thinker. One of his original thoughts continues to stand out: most people act as if there are no secrets left to find.

Shoe Dog — There are few brand founders as accomplished as Phil Knight, the man behind Nike, which now has a market capitalization of $152 billion. Shoe Dog explains how Knight accomplished what he did. By all accounts, he was a tyrant in the process. Consider this quote:

The cowards never started, the weak died along the way — that leaves us.

Knight embodied the spirit of the athletes that Nike sponsored. A ruthless leader with a work ethic that the shoe industry’s leaders, whether American or Japanese, could not account for. If Shoe Dog was foundational text, Swoosh is as well. Gifted to me by Casey Armstrong, the Chief Marketing Officer of ShipBob, this unauthorized version tells more of the story. If Shoe Dog is the important Disney version, Swoosh is its Wolf of Wall Street. Yes, read that one too.

The Man Who Solved The Market — This inspiring Jim Simons story transcended investments. I read this book as a primer for my renewed enthusiasm for mathematics. Simons used it to his advantage by quantifying markets in automated ways before anyone else knew to do so. Not only does this cover the rise of Renaissance Technologies, it explains how the fund influenced our markets first and then our politics. One of the world’s most accomplished investors built a culture that built wealth, that wealth built new industry magnates, those magnates helped America’s 45th president get elected. Robert Mercer is the former CEO of Renaissance Technologies and the principal investor of Cambridge Analytica and partner to Peter Thiel’s Palantir. His daughter is Rebekah Mercer. Simons and his hedge fund are major donors to another candidate.

A Most Beautiful Thing — A recount of the first all-black high school rowing team, Arshay Cooper’s book touched me deeply. Chicago’s West Side was an extremely difficult place to grow up. It is the story of someone without the bottom rungs of Maslow’s Hierarchy of Needs building his own safety and psychological support through sports. This book is especially close to me. Sponsored by Rowing Blazers, an early investment of 2PM’s, the story became a documentary executive produced by John Carlson, father of Rowing Blazers founder Jack Carlson, and directed by Mary Mazzio. Narrated by Common, the book and documentary shows the depth of ingenuity and the ability to overcome the most extreme of circumstances: poverty, violence, and neglect.

American Rule — Jared Sexton Yates covers 300 years in 300 pages. His ambition is to completely reexamine American history and the myths that we now believe to be law. It’s an uncomfortable read for some. Of course, some will view it as partisanship but when you do read it, look beyond that. Understand the greater themes at play and how they interact with our lives today. Sexton identified blind spots that I didn’t consider. For instance, when we discuss complicity, we rarely mean our own. This book makes you look inward. The book topples giants and raises the forgotten. This excerpt is one that I will never forget:

[I]t becomes obvious that the march on Selma, the Stonewall uprising, Frederick Douglass’s fearless turn as America’s conscience, the perpetual struggle by women and vulnerable minorities to seek equality, and even the ability of people to continue striving, dreaming, and just surviving in a system designed to hinder them at every turn, are just as inspiring as a band of eighteenth-century revolutionaries defeating Great Britain, the world’s foremost empire.

Something to consider.

Empire of Cotton — Harvard historian Sven Beckert’s book on the global history of the cotton trade sat on my desk for months before I had the courage to pick it up. And this one is of the most personal to me. I am the descendant of Nigerians and the English. Half of my family worked in North Carolina only to meet the other Louisiana half in 1979. I’d be born four years later. Beckert’s book is another uncomfortable read. He paints the world’s penchant for war capitalism as a fact as common as the air that we breathe. Consider this excerpt:

When “free trade” was imposed upon the Ottoman Empire in 1838 and British cloth “flooded the market in Izmir,” local cotton workers lost their ability to maintain their old production regime.

Free trade, the economic principle that many of us cherish, was at the root of the rise in capitalism and free labor. It wasn’t a uniquely American problem. The entire world was aided by American labor. Beckert’s words are as objective as you’ll find on the matter.

The Righteous Mind — As a native Texan who now lives in Ohio, navigating religion and politics may as well be part of my job description. Given the entrenched divisions that we find ourselves standing behind, this 2012 book by Jonathan Haidt is one that should have been read by more of us before now. The book sympathizes with Haidt’s liberal politics but it does paint a clear picture that, regardless of what you believe, our perspectives on morality are often wired from birth. This can be blinding to others and Mind implores readers to consider their own blind spots.

Einstein’s War — Arthur Stanley Eddington was the star of this book written by Matthew Stanley. It is a parallel biography of a scientist and thinker who partnered with Einstein to evangelize his scientific breakthrough. Eddington and Einstein were both pacificists, teetotalers, and bohemians but Einstein’s theories fueled Eddington’s practical science and expeditions. The result was both of them rising through the ranks of British astronomy. Merit was not enough; it was Eddington’s marketing and communications expertise that turned an unknown scientist into a legend, almost overnight.

Extreme Ownership — By now, the business world is aware of former Navy SEAL Commander Jocko Willink. I was introduced to this book, written by Commander Willink with Leif Babin, through a few mutual friends. While it can be predictable at times, the knowledge that radical accountability can be a competitive advantage takes all 288 pages of the book to break through. It’s chock full of takeaways like this:

When setting expectations, no matter what has been said or written, if substandard performance is accepted and no one is held accountable — if there are no consequences — that poor performance becomes the new standard. Therefore, leaders must enforce standards.

The Restless Wave — I didn’t always agree with his politics, but the late Naval officer, prisoner of war, and U.S. Senator John McCain was a hero of persistence and reinvention for me and many others. There was a moment or two in the senator’s 2007 presidential campaign that I believe many of us would respect a great deal more today. He wasn’t the perfect politician but he had a civility about him that we could use more of today.