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Heart and Solo

Beyond the Silicon Valley fallacy

Rob Csernyik

The Soul of an Entrepreneur: Work and Life beyond the Startup Myth

David Sax


304 pages, hardcover, ebook, and audiobook

As the former owner of a retail store, I’ve done my share of soul-searching — a weighty, agonizing task I wish only on enemies. Having closed my shop in one market and moved it to another, where it met the same fate, I’ve experienced the full life cycle of a business. I once believed going it alone meant a world of endless possibility. But in the actual trenches of entrepreneurship, I experienced the limitations of financing and the reality of how much a sole proprietor can reasonably accomplish in a given day.

Even though small businesses like the one I owned make up a large swath of the economy, our image and struggles aren’t reflected when talk turns to entrepreneurship. That’s why, in the years since closing, I’ve grown increasingly frustrated with how entrepreneurs are framed. Instead of hearing the modest mom-and-pop success stories, we’re bombarded with praise for a hustle culture that lionizes endless workweeks and unhealthy sleep patterns. The idea of building a sustainable career has been usurped by the dream of netting a quick fortune or becoming a celebrity thought leader. Failure has also been gentrified as a mere hiccup or narrative device in the prototypical entrepreneurial journey, instead of the traumatic and costly experience it actually is.

Much of this framing centres on the sexy stories of Silicon Valley start-ups that have made it big: Steve Jobs and Steve Wozniak with Apple, Larry Page and Sergey Brin with Google, Elon Musk with Tesla. The list goes on and on. But those, the Toronto-based business writer David Sax writes, are scenarios that actually happen to “very rare, very specific” individuals. What we end up with is a myth that leaves most entrepreneurs high and dry.

The Silicon Valley entrepreneurship fallacy is taught in business schools. It’s become the yardstick for worthwhile investments. It’s reshaped how we measure success. Although we live in a supposed golden age of entrepreneurialism, the actual statistics suggest the number of people working for themselves is stagnant at best.

So if it’s a myth that drives the headlines, what actually drives real entrepreneurs on the ground? This question is Sax’s starting point in The Soul of an Entrepreneur. He believes that a corrective shift from flashy tales to entrepreneurship’s “soul” can make the entire business field more equitable and satisfying: “Because no matter what kind of entrepreneur you are, from the modest side hustler to the most ambitious captain of industry, entrepreneurship is a constant process of soul searching.” Unfortunately, the fluid and intangible nature of the soul makes it very difficult to pin down, particularly in a data-driven world.

Sax follows individuals — from the beauty guru in New Orleans to the Syrian restaurant owners in Toronto — whose stories, he thinks, will bring us closer to understanding the entrepreneurial spirit. Take, for example, Tracy Obolsky, who starts most days with a bong hit and some surfing before opening her Rockaway Beach bakery, in Queens. She works long hours but enjoys a beach-bum lifestyle rich with community. In choosing to profile her, Sax passes over the usual fatigue and mess of food service, the endless monotony of a six-day week, and the financial burden of doing business in New York. Obolsky’s comfortable enough with her bakery’s performance that one day she shuts early to catch some waves. Precious few sole proprietors could possibly join her in such spontaneity.

Often absent from Sax’s account, yet omnipresent in the life of an entrepreneur, is the looming threat of failure. Even without a pandemic causing innumerable business collapses, large and small, overlooking failure seems strange. Because avoiding it, fearing it, and recovering from it are part and parcel of the lifestyle.

The closest we get to this hard truth is with a rancher in California who struggles to make ends meet. “Did you see that article on Business Insider about grass-fed billionaires?” the rancher asks Sax. “That’s because it was never written.” As Sax outlines the rancher’s challenges, readers see a dead man walking — or rather spending his days driving from pasture to pasture to check on his cattle, because his attempt to purchase a single larger ranch fell through. It is here and in the book’s final chapter, about an older entrepreneur chasing the last big project, that Sax draws near the intangibles that he seeks to illuminate.

For many, it makes perfect sense to get out of the cattle business before the financial and personal losses become insurmountable. It also makes perfect sense for a seventy-five-year-old to retire, rather than chase after a blockchain-powered renewable energy trading platform. But entrepreneurs are a different breed than those who seek comfort in consistent paycheques.

In recent years, social entrepreneurship has gone from a fringe theory to its own discipline; by creating social, environmental, or cultural change, it has an additional mission beyond traditional business activities. The examples of social entrepreneurship are many, from Grameen Bank’s microlending to Tentree’s planting of ten saplings for each item of clothing it sells. But Sax largely resists such narratives: “I would speak with experts on social entrepreneurship or entrepreneurs who had created companies that sold t-shirts to fund eyesight research or made clothes where you could trace the working conditions of their factories, and I felt I was only scratching the surface of an entrepreneur’s deeper values. I wanted more.” Instead, in his least convincing chapter, Sax illustrates values-driven entrepreneurship with a business owner selling his company to employees through an esoteric financial mechanism.

Sax’s personal story ebbs and flows throughout The Soul of an Entrepreneur. At one point, he interrupts his most fascinating discussion, of a troubled family-owned winery in Argentina, with a three-page personal digression. As he muses about his own entrepreneurial activities, as a speaker and a writer, we learn various trivia about him and the enterprisers in his family. But we don’t learn anything profound about what drives them. Sax could have grouped these intermissions together, perhaps in the introduction or a stand-­alone chapter; he could have mined the material he knows best more deeply.

Ultimately, Sax’s success in uncovering an entrepreneur’s soul will be judged differently by readers who have been entrepreneurs than by those who have not. In his final pages, he offers something of a revelation: that all business owners can brand themselves entrepreneurs, that the word is not an exclusive term for rarefied individuals. And while that epiphany may surprise some outsiders, it will fall flat for those of us on the inside.

History is littered with more failed businesses than successful ones, yet people still believe that entrepreneurship can change their lives, that it can scratch an itch that traditional employment can’t. Perhaps for us, this book will prompt some soul-searching of our own. What drives us is not actually a question I’ve spent much time considering until now. If pushed to say why I opened a business, I would drum up reasons like a willingness to accept risk, a desire for self-determination and flexibility, or the belief I could succeed in a fickle industry. But I see these as calculated, practical considerations — nowhere close to the core of my soul.

What drives the entrepreneur is a more pertinent issue than ever, as business owners around the world face a reality far from the glossy myths of Silicon Valley. In the journey with Sax and those he meets, there’s hope to be found, even if the most pressing questions remain unanswered.

Rob Csernyik, a freelance journalist in Saint John, edits the website Great Canadian Longform.