How COVID-19 Redefined the Entrepreneur

David Sax remembers the exact day he knew he might be screwed: Tuesday, March 10th, 2020. His book, The Soul of an Entrepreneur, was scheduled to come out a little more than a month later, but the scope of the coronavirus pandemic had already started to come into shattering focus.

“I spent the first week frozen, unable to move or do anything and generally freaking out,” Sax told Squarespace. “And then I talked to my agent who said, ‘The entrepreneurs and business owners you write about are bearing the brunt of all this. You have to talk about that.’” So Sax went out and talked about his book wherever he could, however he could, even if that often meant discussing his thesis from behind a laptop, looking into a webcam.

This ad hoc publicity tour wasn’t exactly what the bestselling author had in mind. Sax had spent the better part of a decade writing about everything from Jewish delicatessens to asking why a generation of digital natives have returned to buying “analog” items like vinyl records and beautifully crafted stationery. Those books and their life cycles had a familiar contour: Research, write, publish, promote, (hopefully) repeat.

The mythos of the American entrepreneur was his newest investigative target, and Sax had spent years talking to people with modest, enviable ambitions of making enough money to be happy. Another promotional circuit was on Sax’s horizon when the coronavirus pandemic emerged, and the worlds of both entrepreneurship and book publicity were smashed to bits. 

Launching a new book typically means a whirlwind tour with an itinerary that rivals most rock bands: A new city every day for weeks on end where you’re faced with a packed schedule of public readings, Q&A sessions, and interviews. For authors like Sax, those can stretch on for weeks at a time as you attempt to maintain buzz around something you spent years researching and writing—and to lay the groundwork for any future projects you may have in mind. He had successfully navigated the complex world of publishing PR several times before, but COVID-19 took that traditionally intimate—and at times chaotic—process off the table, and Sax was forced to do what so many other entrepreneurs do: Improvise. 

After his initial shock wore off, Sax started sussing out opportunities and looking into unorthodox ways of connecting with his audience. His plan was cobbled from necessity and inertia, a familiar construction to any entrepreneur who was impacted by COVID-19. He found libraries and bookstores who would let him do remote readings, and dealt with the digital dearth of direct interaction that he was so often energized by during speaking engagements. (“I am someone who thrives on an audience,” Sax told Squarespace.)

The result was a marketing strategy taped together with spare parts, like a soapbox derby car built from scrap. But boy, did it run. 

“There’s this incredible sort of beauty to it all,” Sax says. “There's this interaction, this engagement. You're able to talk to the people directly.” He’d done nearly a dozen remote events at the time of writing, and learned how to lean on the intimacy of the event to create new connections with readers on a new, potentially global scale.

“I still believe the in-person experience is the highest value one,” Sax says. “But the ability to talk to people all over the world and make a connection with someone quickly and easily? That's exciting. That's incredible. That's just a great opportunity.”

There’s no doubt the entrepreneurial spirit was warped by the COVID-19 pandemic. The rate at which Americans lost their jobs during the worst period made every unemployment chart look like a Cartesian Half Dome, a staggering rise seemingly summoned up from nothing.   

But, that mutation of entrepreneurial essence shouldn’t be mistaken for a vacancy. Business owners of all sizes simply fell back on entrepreneurial ingenuity to adjust to a new normal. Think of the restaurant owners who converted their businesses into makeshift grocery stores or the fitness instructors figuring out how to lead digital sweat sessions on the fly.

The agility to make those decisions quickly is at the heart of entrepreneurship, something Sax explored as he navigated his own makeshift methods. “There’s a deeper meaning of what it is to be an entrepreneur is something I’ve been focusing these conversations on,” says Sax. “The two essential truths of being an entrepreneur, which is freedom and risk. Every entrepreneur has the freedom to decide what they're going to do today with their business, with their life, and they can change that on a whim.” 

He sympathizes with entrepreneurs who have been laid low and may be at a loss at what to do next, though. Research shows that there’s something deeply personal about failing when the business is your own. We tend to assign senses of self-value and worth to entrepreneurial ventures, and saddle them with our insecurities and prides. Losing your own business goes beyond financial consequence, it can get at your very being. “Who am I if I'm not the owner of David's gym or David’s cruise ship line,” Sax told me. “That loss can trigger a deep spiral.” 

There’s a chance this upheaval transformed the jobs market for good. When Sax was researching his book, he assumed that America was already in an entrepreneurial Golden Age. It wasn’t until after an illuminating conversation with an economist friend that Sax rethought his entire hypothesis. 

They were having breakfast together one morning when Sax brought up his Golden Age hypothesis. “I started talking about all the startups and articles about entrepreneurs and pitch competitions and accelerators,” Sax said. “And he stopped me and said, ‘You should look at the data.’” So Sax did, and found that America had in fact been in an entrepreneurial ice age for the better part of 40 years. 

“When you measure entrepreneurship by the metrics that actually matter, like how many people every year in a country like the United States go out and work for themselves and start a new business and so on, entrepreneurship has been declining for the better part of my lifetime,” Sax said. The contradiction between the media narrative and reality was a sign that Sax was on the right path, and he decided to dig into why we’ve settled onto a monolithic definition of entrepreneurs and why people have shied away from working for themselves for decades. 

The COVID-19 pandemic could have been something of a vicious wake-up call for that slumbering population of potential entrepreneurs, similar to how the last recession served as an incubator for several world-changing ideas. There’s a chance this crisis forced people to reimagine what an entrepreneur looks like and define success on their own terms.

“There are not going to be jobs for everybody who has lost one,” Sax told Squarespace. “There are going to be millions of people figuring out what they're going to do, and some of these ventures will be small and just about being able to pay for food and keeping a roof over the family's head, and that's okay. That's what we need right now.”

The term entrepreneur has taken on a specific contour in the last few decades. When the word emerges in conversation, it speaks into being a very specific image, courtesy of Hollywood technothrillers dating back to the 1990s: white, male, perched next to an early model computer or smiling awkwardly in front of a screen plastered with code. It’s easy to think of entrepreneurs as a single species because, as Sax says in The Soul of an Entrepreneur’s introduction: “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.”

Letting a single definition dominate entrepreneurial taxonomy has done the rest of us a disservice, though. Billionaire startup wonderboy founders aren’t the only entrepreneurs out there. Not by a long shot. The reality of entrepreneurship was reflected in the people who started businesses because they had to, because that was the option that gave them the most independence and meaning. The clear-eyed vision of that world is at odds with what we see on the covers of business magazines, and that bias was doing the world a disservice. Says Sax:

“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 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.”

Dispelling that Silicon Valley stereotype and investigating the motivations of entrepreneurs beyond a chance to strike it rich are two of the underpinning goals of Sax’s book. He spends the better part of 300 pages interrogating a single, vital question: What does it mean to be an entrepreneur? 

The answer, Sax found, is deeply personal, and even though he says that no two entrepreneurs are the same, they all have a singular, timeworn desire to work for no one and bet on themselves. At times that works out, as in the case of the dozens of Silicon Valley wunderkinds who face down serial bankruptcies before hitting the jackpot. (Never mind that those speed bumps are what one bankruptcy attorney Sax interviewed calls “OTP” [“other people’s money”]— bankruptcies.) 

But other times, entrepreneurship can take a psychic toll on its adherents. There’s the tale of a rancher in Mariposa County, California, who spent his savings on purchasing a few head of cattle with visions of starting a grass-fed beef farm. “As an entrepreneur, he was neither a clear success nor a failure,” Sax writes. “Like most people who start their own business, he was doing work that he truly loved and making a living at it, but he also felt stuck, with no clear path on how to move things forward.”

The rancher serves as both a mirror for Sax’s own path to professional independence as well as the embodiment of the yeoman entrepreneur that wasn’t plastered on the cover of magazines or used as shorthand for meteoric success. Like so many other people, he just didn’t want to work for anyone but himself. The rancher’s nightmare is selling insurance in a suburban wasteland somewhere, and he’d rather fight tooth-and-nail to maintain his and his family’s independence than marginally thrive working 9-to-5. 

Freedom, then, may well be what defines the soul of an entrepreneur. The freedom to pivot on a dime when circumstances demand it, or find a new path that would have been obfuscated if you worked in a corporate setting. It’s the freedom to do what David Sax did when the pandemic threw a stick of dynamite into the world of book publicity. “Everything happening right now has reinforced the idea that you have a duty to change things if you don’t like the way they’re going,” Sax said. “It’s always been up to me. That's my truth as an entrepreneur, and I have to go with that. I have to work with it wherever it takes me.”