Inside the Longlist: Entrepreneurship

A fascinating and helpful byproduct of the awards process is being reminded of business’s incredible spectrum. Though every business falls on a type spectrum with constantly moving bookends might be obvious, we (the royal we) tend to unwittingly slink into binary thinking—business is big or small, corporate or independent, innovative or traditional. But that’s not how the world really works, a fact made clearer after sifting through, then drilling into, dozens of books that fit the Entrepreneurship billing each year.

A simple way to think about the Entrepreneurship category is to think about a stack of books that encompasses everyday life. In one day we might interact with the world’s largest institutions by communicating and shopping online and minutes later grabbing Bánh mì from a food truck owned by a single person. At breakfast we brewed coffee roasted by a growing independent chain with a hundred employees, after which we stopped by the credit union serving a mid-sized town’s worth of customers, followed by a quick check-up on a donation we made to a friend’s and aspiring entrepreneur's crowd-sourced funding campaign.

This year, like most years, the five category finalists for Entrepreneurship represent this incredible cross-section of what business is, and going even further, what business can be.

As someone whose late teens and early- to mid-twenties were in part spent embracing a naive blue-collar romanticism and in part cutting my teeth at 800-CEO-READ, my eyes grew wide from the the second paragraph of the Preface of Paul Downs’ memoir Boss Life:

When I began, I had no training as a businessman and no mentors to help me. I just wanted to make stuff and have fun.

Boss Life is, to say the least, refreshing, in that Downs doesn't pretend he has a blueprint for small business success. Rather, he painstakingly walks readers through his actual experiences, revealing what too many business books gloss over: running and growing a successful small business is really, really hard, full of gut-wrenching decisions, and littered with frustrating mistakes. Aspiring entrepreneurs might glean lessons from Downs' story—both his failures and successes—but the real power of this book is simply that it mirrors not only a select few IPO chasing dreamers, but the experience of millions of business owners just looking for a solid life.

Far on the other side of the constantly evolving entrepreneurship spectrum is Edward Tse’s deep dive into China’s exploding tech sector and those leading its charge. The most publicized example of fast-rising entrepreneurial tech success in China has been Alibaba’s Jack Ma, but as China’s Disruptors reveals, Ma and Alibaba are just one in a growing club of forward thinking, success hungry, and innovative Chinese businesspeople having a big impact on the global economy. What pulls this book into category finalist territory is that it doesn’t simply document success, it employs case studies, interviews, and a deep and intimate knowledge of how Chinese capitalism comfortably yet delicately co-exists with what is officially still a communist country to reveal how and why Chinese entrepreneurs are neck-in-neck in the race for what most U.S. tech innovators are ultimately credited for seeking: progress.

From young idealist with an insatiable desire to help those much less fortunate through charity and volunteerism to realized entrepreneur actively fighting global poverty, Jessica Jackley’s perspective on entrepreneurship is special. Her book, Clay Water Brick, is doubly impressive because it contrasts her own challenging entrepreneurial journey with the unflinching entrepreneurial spirit of so many with so little, people living in the world’s most challenging economic conditions who all share a sheer determination to make their, and their community’s life, a little bit better each day. And what really brings this book home is that it isn’t written from an ivory tower. Jackley is not an enlightened Westerner liberating poor third-world inhabitants. She’s not imparting wisdom and a series of lessons upon those whom she has helped through her microfinancing organization, Kiva. No, Jackley is taught and helped as much by those she intends to help as they learn from her.

If Jessica Jackley’s book is the on-the-ground, experiential, and story-based book about doing good through entrepreneurship, Roger Martin’s and Sally Osberg’s book Getting Beyond Better is it’s highly structured and academic-in-the-best-way companion. Martin and Osberg, who both hold important positions with the Skoll Foundation, originally set out to differentiate between Social Entrepreneurship and Social Advocacy in order to properly identify those most deserving of the foundation’s social entrepreneurship funding. What the authors ended up with in this book is not only that clear delineation, but a clear and transparent structure for what constitutes social entrepreneurship and how best to make change in the world. Because ultimately, while social entrepreneurship relies on advocacy, nothing truly changes without what the authors have determined are stages three and four of transformation: building a model for change and then scaling the solution. That’s how the world changes, and this books is essential to that understanding.

And finally, if you’ve been following along with our awards so far this season, you surely remember our General Manager Sally pointing out overall trends:

Whereas in years past we’ve seen books about how technological innovation is changing the world and shaping our future for the better, this year, perhaps the most optimistic books on our future are those that focus on social entrepreneurship (Getting Beyond Better), narratives of classic industries and bricks-and-mortar business striving to reinvigorate their culture through humanistic management practices (Everybody Matters, We Are Market Basket), and even books about devising new accounting metrics (Six Capitals, Or Can Accountants Save The Planet?), instead of laudatory accounts of tech companies. Even the tech startup book on the list—Startupland—is about a business that builds customer service tools.

Exactly.

China’s Disruptors is surely about about technological innovation shaping our future (among the many other things it is), but the best books we saw this year focused on humans and change and being better. And yes, “Even the tech startup book on the list—Startupland—is about a business that builds customer service tools.”

The Startupland story, or at least the general outline of the story, is not new. We referenced the story outline in discussing Clay Water Brick above—hardship, belief, risk, perseverance, more risk, success. But every story is not the same and what separates them are the hows and the whys and ability of the author to translate those hows and whys into a well-written, purposeful book. Mikkel Svane, one of three Zendesk founders chronicled in the book, does a wonderful job with that translation. He also articulates beautifully where Zendesk bucked convention both in strategy and philosophy. My favorite two paragraphs of any entrepreneurship book this year are:

In Silicon Valley there’s a lot of talk about failure—there’s almost a celebration of failure. People recite mantras about “failing fast,” and successful people are always ready to tell you what they learned from their failures, claiming they wouldn’t be where they are today without their previous spectacular mess-ups. To me, having experienced the disappointment that comes with failure, all this cheer is a little odd.

The truth is, in my experience, failure is a terrible thing. Not being able to pay your bills is a terrible thing. Letting people go and disappointing them and their families is a terrible thing. Sure, you learn from these ordeals, but there is nothing positive about the failure that led you there.    

Combine those two paragraphs with the belief that giving back to the community is as important as the bottom line, as well as the idea that boring can be beautiful in service to a mission like Zendesk’s, “remove friction, barriers, and mystery in order to make customer service easier and more approachable”, and yeah, Startupland is worth every entrepreneur’s time.