The Soul of an Entrepreneur

Introduction

A FEW YEARS ago I saw two things that changed how I look at my life.

The first revelation appeared to me from the magazine rack of a Hudson News store in Montreal’s airport. Amid the sports, news, and cooking publications, the cover of Maxim stopped me in my tracks. The magazine was dominated by a black-and-white photograph of Heidi Klum, the forty-five-year-old German supermodel, who appeared completely nude from the waist up. Klum’s eyes gazed down seductively, and her streaked blond hair fell just enough over her perfect breasts to obscure her nipples. But it wasn’t Klum’s flesh that held my gaze and had me pull out my phone to snap a picture (regardless of how creepy I looked). It was the words that appeared atop it. There, splashed across her bosom in bright red script, read the headline:

Heidi Klum
Inimitable
Entrepreneur

A few days later, back home in Toronto, I drove to a cemetery with my wife, Lauren, to visit her father Howard’s grave on the eighth anniversary of his death. After a few minutes of standing there, I spotted the gravestone of a man named Freeman, who was buried in the row behind Howard’s. The engraving on his stone listed the usual details; the dates of Mr. Freeman’s birth and death, and the fact that he was a devoted husband, father, and grandpa, who made the world a better place. But below that, permanently etched in black granite, was the sentence that had me reaching for my phone again:

Brilliant salesman and entrepreneur until the end.

I have spent half of my life so far working for myself. Writing stories and books. Giving talks to whoever will pay me. Working from home, in shorts or sweatpants. Shaving once a week, unless I have to meet someone. I have no idea where the next payment is coming from, or how much money I will make this year, or what I am going to do the day after I finish writing this book. I haven’t seen a regular paycheck or had a boss since I held a brief, miserable office job as a copy boy during the summer of 1999, and the only other jobs on my résumé are stints as a ski instructor and camp counselor (qualifying me for roles in an ’80s comedy, but nothing else). I am certain that I will never work for anyone but myself for the rest of my life.

This is my reality. I am my own boss. A freelancer. Self-employed.

I am an entrepreneur.

A few years ago I doubt I would have used that term to describe myself. I employ no one, have never invented anything, or really innovated in any way. But something changed the week I saw that same word splashed across Ms. Klum’s bosom and Mr. Freeman’s grave.

I began to realize that something crucial was happening with entrepreneurs at this moment in time, which these two wildly contrasting visions of entrepreneurship represented. On the one hand, you had the sexy public image of entrepreneurship in the form of a celebrity who had parlayed runway, advertising, and television success into several clothing brands, ranging from baby wear to lingerie, turning her from a multi-millionaire into a multi-multi-millionaire. On the other you had the grave of an octogenarian businessman, whose legacy was forgotten except to his family and those who knew him, one of countless entrepreneurs in my city and in this world who identified with that title so much, that it followed him to the grave. Here was the tomb of the unknown entrepreneur.

I have always been fascinated by entrepreneurs. The articles I’ve written over the years almost exclusively focus on people who work for themselves, from a cohort of young bankers who went out on their own during the financial crisis (starting yoga studios, robotic toy companies, and solar finance firms), to the tribe of freelancers who plug their laptops into a Brooklyn café every morning. My books all focus on entrepreneurs. Save the Deli, which chronicles the rise and fall of the Jewish delicatessen, isn’t as much about pastrami sandwiches as it is about the men and women who built the businesses that served them. The Tastemakers, which is about food trends, is told through the eyes of the dreamers who passionately believed that their cupcake shop, food truck, or new breed of apple was going to change the way people ate. The Revenge of Analog is riddled with analog entrepreneurs, from the plucky bookstore owners who faced down Amazon, to a pair of half-crazy Italians revitalizing a mothballed film factory.

I rarely wrote about big corporations and organizations, and when I did, I regretted it. They were cold and impersonal, and the people who worked there were always worried about saying the wrong thing. I was drawn back to entrepreneurs again and again; their stew of personal passion and hustle, a work life inseparable from their self, and a sense of purpose to everything they did.

Was it surprising? Not when I thought about it. After all, I was the product of entrepreneurs, from the immigrant ancestors who found their way into some corner of Montreal’s garment trade a century ago, to my grandfathers, who both owned their own businesses. My paternal grandfather, Poppa Sam Sax, had a series of never quite successful companies in the schmatte business, while my mother’s father, Stanley Davis, built a hardware company with his brother that continues to supply screwdrivers, pliers, and other tools across Canada. My father has spent his entire career since law school working for himself as a lawyer and investor, and even my mother ran a side business with her best friend Paula, selling wholesale women’s clothing twice a year out of our basement for nearly two decades.

My wife Lauren’s family was no different. On her father’s side were Polish immigrants who founded a truck parts distribution business, while her mother’s parents were Holocaust survivors who’d arrived with nothing and dabbled in everything, from stationery stores to feather collecting. My beloved mother-in-law, Fran, may hold one of the first MBAs in the country awarded to a woman, but she has spent her professional life at folding card tables in hospitals and at flea markets, selling all sorts of things: macramé planters, rattan furniture, and whatever inexpensive women’s accessories China’s sweatshops can churn out that season.

Each month I had friends leaving careers and steady jobs to build branding agencies, law firms, software startups, rug stores, cafés, bike shops, yoga studios… even a chopped liver company. My brother Daniel recently quit his job at a mortgage brokerage to launch his own real estate investment company in Canada’s booming cannabis industry, while Lauren began her own career coaching business, after working as a corporate headhunter for a decade.

Outside my own world, something bigger was happening with entrepreneurs that drove my curiosity. There was already an inescapable buzz in the air about entrepreneurs: the crowded coffee shops packed with laptop wielding dreamers working on their ideas, the blossoming of coworking spaces to house all sorts of freelancers and new companies, the decline of the steady job and the eagerness of younger generations, like the Millennials, to go out on their own. And of course, the inescapable startup fever, which had spread far beyond Silicon Valley to inspire millions around the world to launch businesses like never before.

There was a noticeable change in the entrepreneur’s value to society, which altered the way we spoke about them as a group. Entrepreneurs were cool. Entrepreneurs were brilliant. Entrepreneurs were in demand. Entrepreneurship had entered the core of the zeitgeist, not just in the contained world of business and economics, but out in the wilds of popular culture.

Newspapers and magazines regularly featured entrepreneurs on their covers, spinning exciting tales about their transformational businesses and thrilling lifestyles. They published endless lists of the top entrepreneurs to watch: the fastest-growing ones, the most inspiring, those who would change the world, the twenty under twenty, thirty under thirty, and so on. Headlines proclaimed entrepreneurs as the new rock stars, a group who were downright sexy, even if they weren’t actually posing topless.

The bestseller lists became dominated by heroic books about the most famous entrepreneurs: biographies of Elon Musk, Richard Branson, Steve Jobs, Peter Thiel, Jeff Bezos, Nike’s Phil Knight, and others, while airport bookstores featured a rotating selection of how-to books on entrepreneurship, ranging from online wine pitchman turned motivational guru Gary Vaynerchuk (Crush It! and Crushing It!), to less recognizable names like Miki Agrawal, a media fixture of New York’s startup scene who had started a pizzeria, an underwear company, a bidet toilet seat company, a series of early morning raves, and whose book, Do Cool Sh*t: Quit Your Day Job, Start Your Own Business, and Live Happily Ever After, boldly sold the dream of entrepreneurship for all.

Who wouldn’t want to do cool shit, especially when social media entrepreneur influencers like Agrawal were cheering you on, posting inspirational quotes and streams of advice on Instagram, lists of instructions on LinkedIn (Five Secrets to Hack Growth You Need NOW!), Snapchat videos filmed in cars, and a growing series of hashtags, from #startuplife and #founder to #entrepreneur and more specific ones, like #solopreneur, #serialentrepreneur, #mompreneur, or those meant to encourage entrepreneurs through the slog ahead: #wontstop, #beyourownboss, and the endlessly deployed #hustle (or its less committal sibling #sidehustle).

Podcasts? How about Startup, The Foundation, The Introvert Entrepreneur, Eventual Millionaire, All In, Ambitious Entrepreneur Show, and Entrepreneur on Fire, to name a few of the thousands out there. Turn on your TV and you could spend all night watching shows about cake-making entrepreneurs and matchmaking entrepreneurs, storage locker hustlers and bounty hunters out to grow their businesses. Willie Robertson, the star of Duck Dynasty, even authored a book called American Entrepreneur, a history of American entrepreneurship, told from the perspective, mostly, of Duck Commander’s journey, while Kylie Jenner, of Keeping up with the Kardashians fame, was declared the youngest “self-made” female billionaire by Forbes at age twenty-one, following the success of her makeup company.

Then there is Shark Tank, the American version of the global franchise Dragons’ Den (airing in more than thirty countries), where a panel of aggressive investors are pitched business ideas by a series of budding entrepreneurs, in the hopes of securing coveted funding. Shark Tank is over the top, as you’d expect of a show where Jeff Foxworthy is being pitched a Mafia-inspired money clip called the Broccoli Wad, but it has become so successful that Sharks like Barbara Corcoran and Chris Sacca have become household celebrities, on par with Hollywood actors like George Clooney and Jessica Alba, who now sell their own tequila and diapers, and Drake, who not only hawks clothing through his OVO brand, but joined forces with Canada’s largest bank to host his own entrepreneurship conference (one of thousands put on every year around the world).

In the public mind, entrepreneurs had become a force for unquestionable, unalloyed good in the world. They brought the necessary innovation and disruption that made economies competitive, spurning growth, creating jobs, and giving birth to whole “ecosystems” of startups around them. Entrepreneurs were hailed as creative and agile, able to think outside the box and tackle any problem with more efficiency and determination than even the most well-funded and experienced incumbent. “We don’t know what the problem is, but the solution is entrepreneurship,” joked Howard Stevenson, an entrepreneurship professor at Harvard, when I asked him to characterize this cultural shift, which he had witnessed in recent years. In a way he was right. The entrepreneur had come to symbolize the loftiest angel of our human nature.

Social and Economic Inequality, Labor Relations, Hunger, Homelessness, Public Transit, Incurable Disease, Climate Change, Failing Schools, Gun Violence… suddenly these intractable issues that had dogged our brightest political leaders and institutions were best tackled by young, eager entrepreneurs, who were rightly celebrated for their efforts. I never fully realized the extent of this shift until I was walking in the hallway of a conference center a few years ago, which featured framed portraits of inspiring leaders and their quotes. Alongside the faces of Albert Einstein, Winston Churchill, Mother Teresa, and Martin Luther King Jr. were those of Mark Zuckerberg, Jeff Bezos, Elon Musk, and Peter Thiel. The more entrepreneurs we encouraged, embraced, and set forth, the better we would all be… economically, but also socially, politically, and most important, personally.

Entrepreneurship studies were already transforming education, as universities rushed to set up and expand entrepreneurship departments, producing a growing trove of research on every aspect of the topic, while simultaneously encouraging students to start companies, with investment funding available from their in-house network of venture capitalists, and freshly built incubators, accelerators, and innovation zones to house those companies. To prepare your child for this future, there were now courses on entrepreneurship being offered in high schools and elementary schools, and if those were insufficiently motivating, you could send them to Young Entrepreneur learning labs, which taught children how to start businesses far more disruptive than a lemonade stand, then pack them off to Camp Inc. for the summer, where they could roast marshmallows and write business plans!

From nonprofits and arts organizations to government agencies, word went out across the land that acting, thinking, and working like an entrepreneur was the only thing standing between success and failure. Reid Hoffman, the CEO and founder of LinkedIn, suggested that every career should be treated as its own startup. Corporations, previously seen as the antithesis of entrepreneurs and all they stood for, eagerly embraced the importance of entrepreneurship with a vigor not seen since they discovered the open office. Suddenly blue chip firms like General Motors and Deloitte created official entrepreneur jobs (Entrepreneur in Residence, Disruptor in Chief), with offices, staffs, and executive salaries to match.

I got why this cultural shift made sense. Thanks to innovations ranging from cloud computing and smartphones, to coworking spaces, crowdfunding, overseas manufacturing, and social media, it was now easier to start your own business than anytime in history. Technology had put the tools of scale at everyone’s fingertips, and drastically reduced the time and cost of market entry for any firm. At the other end of things, the allure of the nine-to-five salaried job was rapidly dissolving, especially in the decade following the Great Recession. Job security was a relic. The jobs that existed were being stripped down to the bare minimum in terms of upward mobility, benefits, and engagement. Was it any wonder that the Millennials were widely predicted to become the most entrepreneurial generation of all time?

“There are more entrepreneurs operating today than at any time in history,” wrote Eric Ries, in his bestselling book The Lean Startup. “The side hustle is the new job security,” wrote Chris Guillebeau, in Side Hustle. “You’re lucky because you live in an age of unmatched opportunity for anyone with enough hustle, patience, and big dreams,” wrote Gary Vaynerchuk in Crush It!, extolling readers, in his next book, Crushing It!, to “eat shit as long as you have to” in order to grasp the “brass ring of adulthood” (entrepreneurship) because there has never been a better time to… (wait for it)… Crush… It! The Freelancers Union, a newly formed group that provided benefits to self-employed workers, predicted that the majority of American workers would be freelance in some capacity by 2027. We were living in the midst of a golden age for entrepreneurs and I wanted to chronicle what that looked like.

But when I began looking at the data on entrepreneurship and speaking with the academics who studied it, what I found stood in complete contrast to everything I had assumed to be true. There are fewer people going into business for themselves today than there were twenty or thirty years ago. When Ronald Reagan was in office, two out of ten Americans worked for themselves in some capacity. Today that number is one in ten. This counted for individuals going out to work as unincorporated and self-employed (like me), as well as those starting up formally incorporated businesses.

But what about the Millennials? Turns out that the group that gave us Mark Zuckerberg is the demographic least likely to start a business and work for themselves in nearly a hundred years, a phenomenon that a US Small Business Administration report dubbed “The Missing Millennials.” One study found that college graduates with advanced degrees were half as likely to start a business that employed at least ten people in 2017 as they were in 1992. In fact, the density of startups around the country (the number of new businesses created in a given time period, for every thousand businesses that already exist) was down by more than half of what it was in 1977, when those statistics were first compiled. The data were riddled with all sorts of incomplete information, and these studies contradicted each other regularly, but even the best-case scenario had entrepreneurship flatlining in America and in much of the developed world. Entrepreneurship was not ascendant. In fact, it was declining and had been doing so for years.

Expecting to chronicle the golden age of entrepreneurs, I now found myself reckoning with something far more complicated. How could entrepreneurship be more revered, romanticized, and valued on a broad economic, political, and cultural level, yet when measured by the numbers that mattered (people going into business for themselves), it was stagnant, and in many areas, appeared to be dying? How had we come to revere entrepreneurship so highly, yet gotten it so wrong?

I started asking questions, beginning with academic experts on entrepreneurship. But within a few interviews, I noticed something at the start of these conversations that deepened my curiosity. “What do you mean by an entrepreneur?” they would ask me. I was surprised to learn that there was no single universally accepted definition of the word. An entrepreneur can be described as broadly as anyone who works for themselves. Or it can be as specific a definition as the founder of a business based around a particular kind of innovative technology that they personally invented, with a minimum number of employees, specific rates of growth, and particular financial structures. Some believed that being an entrepreneur had nothing to do with self-employment and described a series of behaviors that could take place anywhere, even in a salaried job. Others cast the word as a mold for a hero of modern-day capitalism, an Übermensch whose goals were nothing short of saving the world through business.

I quickly realized that this one question—What is an Entrepreneur?—was the key to understanding the seeming divide between our rosy perception of entrepreneurs and the more complicated reality of their decline.

And what I saw from the answers was an echo of the inequality of wealth and opportunity present in the rest of the economy. At the top, you had the popular image of entrepreneurship that had inspired all that “entrepreneur porn,” a wonderful term from a 2014 Harvard Business Review article used to describe the way the media pushed an idealized lifestyle about entrepreneurs well past its reality. This was the startup myth forged in Silicon Valley, a well-oiled machine of entrepreneurship with defined roles and rules, sources of investment, and paths to success. This myth drove the headlines, captivated the public consciousness, and made household names out of its icons.

The startup myth dominated discussions of entrepreneurs in the media, institutions, government, and academia, and increasingly defined what an entrepreneur was supposed to look like, how they behaved, and what they did. It established that entrepreneurs were brilliant and young, mostly male and white, highly educated lone geniuses who frequently dropped out of college because they were so singularly focused on a brilliant innovation that would transform industry, and maybe even the world, through economic disruption driven by blitzkrieg growth and fueled by venture capital. These entrepreneurs were deemed the most valuable, because they held the promise of quickly creating the greatest economic benefits… jobs, investment returns, and new lines of business.

But like that airbrushed cover of Heidi Klum, Silicon Valley’s entrepreneurship was far from reality for most of the entrepreneurs I knew. My entrepreneur was someone starting a business that ranged vastly in size, spanned every conceivable industry, and was inherently personal. It was the entrepreneurship of my father, grandparents, friends, and neighbors. It was more often self-financed and grew at a variety of speeds. It was entrepreneurship over the long term, sometimes spanning generations, and it wasn’t captured in slogans or hashtags.

None of this fit into Silicon Valley’s narrow definition of an entrepreneur. Not businesses run by women or minorities or immigrants or seniors. Not people in poor neighborhoods or rural areas, making things with their hands, or selling services that served a local market. Not someone who wanted to stay small so they could pick up their kids from school every afternoon, provide for a family, realize their values, or to scratch a need to do their own thing, in their own way. That was a problem, because out in the real world this broader group of entrepreneurs still made up the overwhelming majority of people going into business for themselves. They fixed holes in my roof and baked my bread, designed my website, changed my tires, and cut my hair. For men and women like Mr. Freeman and the hundreds of millions like him around the world, who toiled in relative obscurity running all sorts of businesses, and yet rightly saw themselves as entrepreneurs until the end, there was a deeper, more meaningful truth to being an entrepreneur that the popular mythology missed.

I came to realize that the way you define an entrepreneur has meaning. It establishes the story we tell ourselves about the inherent promise of economic opportunity and sets us up with the metrics by which we measure success. If that definition is becoming increasingly narrow and rarefied, and casts out the majority of the people in this world who are their own bosses, then what you get is an inequality of entrepreneurship that makes being an entrepreneur less accessible, realistic, or desirable. The system becomes rigged and exclusionary. The benefits and glory accrue to those at the top, and dangerous resentment builds below. The illusion of economic opportunity gives way to the reality of hopelessness. The so-called golden age becomes a veneer.

Over the months that I began having these conversations, my own thoughts about being an entrepreneur were rising to the surface. My wife, Lauren, had finally launched her career coaching business and, for the first time, was completely on her own. I was now witness to an individual’s transformation from a salaried employee comfortably earning six figures, to an entrepreneur starting from scratch, who had to be taught during her first week of working from home that she no longer had to eat a can of sardines by her computer (Self-Employment 101: lunch is sacred). At the same time my brother Daniel worked to launch his own business, with much higher financial risks, in an industry on the cutting edge of uncertainty, and I watched the two of them weather the initial thrills of starting up together.

And then there was me. Nearly two decades into being my own boss, and still figuring it out. Still unsure about where that next check was coming from. Still nauseated by the fear of not enough work, or the stress of having too much. Always chasing that nagging question “What the hell am I doing with my life?” day in and day out. And now… “Am I really an entrepreneur? And if not, then who am I?”

This book is my search for the soul of an entrepreneur, and what that soul looks like today. If you are an entrepreneur, a family member of an entrepreneur, or just someone interested in entrepreneurship, I hope you get a sense of what that soul looks like, the different forms it can take, and why nurturing it across a wide spectrum of entrepreneurship is crucially important now. 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.

Unlike most books on entrepreneurship, I’m not at all concerned with the How (how to become an entrepreneur, start a company, or get rich), but Why.

Why do entrepreneurs do it? Why do they keep at it, even in the face of tremendous odds, and the daily personal sacrifices, and the imminent threat of financial failure? Why does the entrepreneur matter, why do different types of entrepreneurs matter, and what’s at stake if we lose sight of their value?

My search for the soul of the entrepreneur led me to read stacks of books, articles, and research papers on seemingly every aspect of entrepreneurship, in addition to interviewing countless academic experts around the world. But at its heart were the conversations I had with more than two hundred different entrepreneurs over the past two years, on the phone and in their businesses and homes, when times were good and times were bad. I chose these entrepreneurs because their lives and experiences covered a wide diversity of backgrounds, industries, and economic circumstances. This book is a result of those conversations, and the journey that drove them.

Of course, every entrepreneur has her own story, and I found that each person’s idea of entrepreneurship was closely tied to her identity. My own definition of the word evolved over the course of researching this book, and I’ve tried to replicate that experience in its pages. The first group of entrepreneurs described here were those just starting out: an immigrant story about beginning a new life; a woman who built her business around the life she wanted, rather than the other way around; and someone who found success, then turned it to the benefit of the community she came from. The second group was wrestling with their growth: a business owner who discovered what was important to him long after he started his venture; a family dealing with a legacy across generations; and an individual struggling with the personal cost of entrepreneurship for himself and those around him. Finally, I sought out someone reflecting on a life defined by bringing his entrepreneurial ideas into the world, and what that ultimately meant for entrepreneurs everywhere.

Yet I also found it nearly impossible to make sense of these stories without dealing with the singular narrative that still dominates our collective obsession with entrepreneurship: Silicon Valley’s startup myth. This myth had so skewed our understanding of who an entrepreneur was, and what they did, that we had lost sight of its very essence. Before I could move beyond Silicon Valley to search for the entrepreneur’s deeper soul, I needed to face the startup myth head-on. I wanted to understand what it looked like and why it had grown so prominent, what the startup myth’s complications were, and why the imbalance between the myth and the greater truth of entrepreneurship mattered. So I began my journey in the valley, town, and campus where entrepreneurship has a particular name and meaning, defined by its own models and heroes, where the transformational act of becoming an entrepreneur is simply called starting up.

PART I

THE MYTH