The 10 Smartest Reads for Entrepreneurs From 2016

Not every business book that thumps onto your desk is a worthwhile read. But just a cursory glance at the year’s endless stream of flaps, blurbs, and press releases suggests a few trends in 2016. Among them: fewer leadership titles. More niche or skeptical perspectives on data and technology. An interest in the wilder side of entrepreneurship.

Here, in alphabetical order, are 10 of the smartest or most purely entertaining books to read this year–or next year if you’re not a speed reader.

1. Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley

Antonio García Martínez
Harper

In this, chewy, insouciantly candid digital-age memoir, Wall Street refugee Martinez recounts his adventures at his own startup, AdGrok, and within the self-important halls of pre-IPO Facebook. Torching bridges as he goes, Martínez–who also worked at Twitter–describes “the tech whorehouse” of Silicon Valley as a place of mendacity, cultish-ness, and debilitating inside politics. There’s an educational aspect to the book: You’ll learn a lot about ad technology and pick up advice about company building and navigating unfriendly organizational cultures. But Chaos Monkeys is chiefly a story of blood, flop sweat, and tears. Martínez himself isn’t noble–he’s not even nice. But he is a pungent, very funny writer. As he anatomizes corporate pathologies, no telling detail is too small. At one point, he describes using a men’s room at Facebook, where he spots toothbrush wrappers in the trash and hears someone loudly pounding a keyboard inside a stall. “People coded while they shat and needed to be provided with toothbrushes at work,” writes Martínez. “They had my attention.”

2. Deep Work: Rules for Focused Success in a Distracted World

Cal Newport
Grand Central Publishing

The dangers of distraction–ooh … shiny!–are limitless in the digital world. We try to resist that siren social media, but cannot help ourselves. That’s especially harmful when we’re engaged in what Georgetown University professor Newport calls “deep work,” cognitively demanding jobs that deliver high value and require extreme focus. Like any business author worth his salt, Newport lays out a program of mental self-discipline: Track focused time on a scorecard. Schedule periods when you’re allowed to go online–otherwise steer clear. Embrace boredom, so as not to succumb to electronic stimuli when mental activity flags. If necessary, check into a hotel. Unlike other writers in the take-back-your-life genre, however, Newport also writes compellingly about the profoundly worthwhile labor that technology disrupts. Becoming a member of the “focused few” is transformative, a noble goal. By relearning to lose ourselves in work, perhaps we may “connect this sacredness inherent in traditional craftsmanship to the world of knowledge work.”

3. Magic and Loss: The Internet as Art

Virginia Heffernan
Simon & Schuster

Depending on whom you talk to, the internet creates omniscient, über-productive superbeings or uncritical idiots with the attention span of a gnat. Cultural critic Heffernan approaches this era’s capital-D Disrupter with a thoughtfulness and nuance typically lacking in such debates. She treats the internet as its own kind of protean civilization and celebrates its extraordinary capacity to express–or at least to represent–human feeling and creativity. In that vein, she relishes the primal revenge tale of Angry Birds; praises binge-watching for sharpening our critical faculties, and enthuses over “achingly beautiful apps, many of which could pass for objects of Italian design or French cinema.” Yet she also mourns some tender trappings of analog life: the paucity of white space and line breaks in text. The “material reality” of music that is flattened with digitization. “The internet has a logic, a tempo, an idiom, a color scheme, a politics, and an emotional sensibility all its own,” Heffernan writes. “Tentatively, avidly, or kicking and screaming, nearly two billion of us have taken up residence on the internet, and we’re still adjusting to it.”

4. Originals: How Non-Conformists Move the World

Adam Grant
Viking

Grant, a Wharton professor, champions those who zig while others zag. Grant himself zigged in his first book, Give and Take, the influential bestseller that advocated using small, non-quid-pro-quo favors to get ahead. His new work–a characteristic fusion of evidence and anecdote–is about divergent thinkers. These are not wild-eyed status-quo topplers but rather curious, skeptical, creative people who–rightly or wrongly–push against the grain, with all the potential for humiliation, rejection, and loss that entails. Grant shores up aspirational deviants with advice on maneuvering past the inevitable resistance (for example, one entrepreneur with an audacious plan to generate wireless power enlisted top collaborators by cloaking her ultimate goal). And he examines the roles of gatekeepers and critics, whose judgments may be flawed because they know too little about a subject (Steve Jobs predicted great things for the Segway) or because they know too much (many NBC executives at first rejected Seinfeld, which didn’t fit their mental model of a successful series). “In reality, the biggest barrier to originality is not idea generation,” writes Grant. “It’s idea selection.“

5. Pre-Suasion: A Revolutionary Way to Influence and Persuade

Robert Cialdini
Simon & Schuster

Cialdini, a psychology professor, is our most influential expert on influence. His research over 40 years has helped millions of marketers and negotiators get to yes, while alerting consumers to their own psychological Achilles’ heels. Cialdini’s new book pans back to the moments before the pitch to explain how effective persuaders tee up messages through words and actions. Like gardeners, such persuaders “spent much of their time in cultivation,” he writes, “in ensuring that the situations they were facing had been pretreated and were ready for growth.” Much of that pretreatment involves guiding preliminary attention strategically, so that persuadees start agreeing with a message before they even hear it. So, for example, Volkswagen successfully introduced its “Bug” to the United States by admitting up front to the car’s lack of aesthetic appeal–and then weaving ugliness into the sales pitch about simplicity and economy. Refreshingly, Cialdini devotes an entire chapter to ethics. Just because we have the power to sway someone’s opinion, should we?

6. Small Data: The Tiny Clues That Uncover Big Trends

Martin Lindstrom
St. Martin’s Press

Ask entrepreneurs where they get their ideas, and most will cite some epiphany sparked by the simple observation of a person struggling with a problem, or a comment dropped by a neighbor. Such small data are often more revealing than databases bulging with customer information, argues brand consultant Lindstrom. Big data is useful for understanding correlations. Small data illuminates causes: why people do what they do. So Lindstrom urges readers to get out into the field, visiting the homes and workplaces of customers. Once there: Listen and observe. On one such visit, marketers for Lego noticed the scuffed sneakers that a teen-aged skateboarder wore with pride. They concluded that making their bricks smaller and the projects more complex would elicit a similar sense of achievement in many customers: an insight that produced substantial market gains. But devoting resources to field research isn’t enough. Observers must also be fully present to detect telling details. “No matter how insignificant it may first appear,” writes Lindstrom, “everything in life tells a story.”

7. Smarter Faster Better: The Secrets of Being Productive in Life and Business

Charles Duhigg
Random House

Duhigg’s The Power of Habit was, justifiably, a mega-bestseller that offered a path out of destructive patterns of thought and behavior. The journalist’s sophomore effort tackles a broader subject: how to gin up performance in everything we do. Whole books are written about subjects that Duhigg digests colorfully and efficiently into single chapters. Smarter Faster Better is dense with self-help tactics like telling ourselves stories to sustain our focus and attention, setting goals that are both aspirational and realistic, and thinking about the future as a range of potential outcomes. Some of Duhigg’s best material delves into organizational behavior: for example, Google’s research-based effort to build the perfect team. The key, that company discovered, was psychological safety: reassuring members they could speak freely and be listened to patiently. “Are you demonstrating a sensitivity to what people think and feel,” writes Duhigg, “or are you letting decisive leadership be an excuse for not paying as close attention as you should?”

8. Superbosses: How Exceptional Leaders Master the Flow of Talent

Sydney Finkelstein
Portfolio

There are almost as many definitions of leadership as there are books on leadership. Finkelstein, a professor at Dartmouth’s Tuck School, smartly focuses on one of the most overlooked: the leader as a spotter and developer of talent. When you look at stars in a given industry, Finkelstein says, you often find they worked for the same star maker: people like Jay Chiat in advertising, Lorne Michaels in comedy, and Alice Waters in restaurants. Finkelstein set out to discover what those star makers have in common: how they transform their protégés into apprentices and then set them on a course to become supernovas. Through his research, he identified three categories of superboss: iconoclasts, nurturers, and–we’re looking at you, Larry Ellison–glorious bastards. None of them practices drive-by mentoring. “Superbosses can be fierce or gentle, belligerent or self-deprecating,” writes Finkelstein. “But whatever their style, they do a much better job inspiring and teaching because they get in the trenches with protégés, leading by example and giving them the personalized attention they require to move up quickly.”

9. A Truck Full of Money: One Man’s Quest to Recovery From Great Success

Tracy Kidder
Random House

Journalist Kidder first chronicled the intersection of starry-eyed technologists with brutal business demands in his Pulitzer Prize-winning The Soul of a New Machine. Rock star techies abound in his new book, as well, including its hero: Paul English, serial founder of companies such as the travel site Kayak. English’s struggles with bipolar disorder ratchet to the nth degree his otherwise recognizable entrepreneurial traits: creativity, drive, ambition, appetite for risk. Had hypomania “helped him in his role of entrepreneur, boosting his energy and boldness?” writes Kidder, “Or had he made his way in spite of hypomania?” This startup-based version of Lust for Life, is a great entrepreneurial yarn, but also a love story about a fascinating, flawed leader and the loyal team who would follow him anywhere. English–as generous as he is difficult–is at once the embodiment of what we value in a founder and the entrepreneurial archetype run amuck.

10. Wonderland: How Play Made the Modern World

Steven Johnson
Riverhead Books

Johnson’s lovely work of social and technological history explains that innovations–typically viewed as the work of resolute problem solvers–also arise from people simply having fun. We are a species that craves amusement, and often those amusements influence change as much as do utility-focused solutions. So, for example, our desire for music in the form of instruments and music boxes engendered later advances in mechanical engineering. The global marketplace developed around a search for exotic spices. Games played an integral role in the evolution of statistics and artificial intelligence. Charles Babbage, the 19th-century inventor of an early programmable computer, was inspired by the automatons he saw at Merlin’s Mechanical Museum in London. “Everyone knows the old saying, ‘Necessity is the mother of invention,'” writes Johnson, a popular science author. “But if you do a paternity test on many of the modern world’s most important ideas or institutions, you will find, invariably, that leisure and play were involved in the conception as well.”