The Fetishization of American Entrepreneurship

The Psychology of the Icarian Entrepreneur

America has a grotesque fascination with entrepreneurs, with our love to hate ogling and borderline-style adoration.

Tracking the Icarian rise and concomitant plunges of entrepreneurs has become an American pastime with nearly as much grip as royal family tabloids, revealing our peculiar desire to make heroes and villains out of what was once a sublimely unglamorous profession. A new kind of gawkable aristocracy, interest in entrepreneurial gaucheries is at an all time high, even and perhaps especially as the tech sector continues its downward financial descent. 

Look no further than streaming platforms to divulge our captivation. In 2022 alone, tongues wagged as WeCrashed chronicled the hypnotizingly bizarre Adam and Rebekah Neumann of WeWork, The Dropout captured the treacherous charms of voice actor Elizabeth Holmes, Super Pumped tracked Uber’s Dantean Travis Kalanick, and category strange bird Inventing Anna followed Anna Delvey’s breathless desperation for founder fame.

Add to the list earlier flicks, including two laugh out loud absurd documentaries on the Fyre Festival founder (with the ill-famed cheese sandwich) and myriad portrayals of everyone’s favorite tech bad boy, Steve Jobs, and we’re left with a cram-full portfolio of titillating startup pornography. Or more specifically, erotica featuring the salacious behavior of its participants. 

Before we go further, it’s important to realize: Generalized naughtiness is central to the functioning of the innovation ecosystem and is wired directly into the entrepreneurial spirit. Personality research has shown that entrepreneurs score lower in agreeableness (think: more brash, stubborn, and illicit) than managers, with this low agreeability contributing to their innovative potential.

In fact, low agreeableness likely encourages self-selection into entrepreneurship, as it confers adaptive advantages in the entrepreneurial context, like the willingness to go against the grain, risk social disapproval, and tolerate confrontation and rejection. In other words, entrepreneurship is possible because of, not despite, disruptive behavior.

But something has gone awry in our conception of entrepreneurship — in particular, our valuation of the individuals behind the businesses. We no longer celebrate the feisty American spirit, a temperament distilled from a genetic pool filled with risk tolerant people who largely self-selected into the immigration process, but instead glorify a tacky talent show of cowboys and rock stars with Dark Triad personalities.

An ecosystem that was once filled with nameless women and men who opened storefronts, carved stone, and baked pastries of their homeland has transformed into a fountainhead of film fodder and clickbait headlines. Suffice it to say, we’ve lost the plot — only to gain a cheaper, though undoubtedly more entertaining, storyline.

This fetishization of entrepreneurship has come at a high cost, in every sense. While the magnified sex appeal of the tech industry has led to the weed-like growth of venture firms, check sizes, valuations, and media attention, it has also allowed for the engorgement of the entrepreneurial ego.

The glamorization of entrepreneurship has tolerated — nay, encouraged — those with a God complex into the spotlight under the guise of talent, vision, and confidence, much to the peril of investors, employees, shareholders, and consumers. We are now faced with the aftereffects of these ill-advised human investments, as more and more moral and criminal failings roil to the surface. See here and here and here and here and here and here.

How do we fix an ecosystem in such disrepair? Like any ecosystem that has been overtaken by an invasive species, balance must be sought. Fidgety questions must be asked of investors, like why rigorous diligence efforts miss, ignore, or actually select for these dark personality types.

Investing in founders who value both power and benevolence is not an antithetical quest, and, contrary to popular expectation, is also not a matter of betting on explicitly impact-driven companies. Instead of focusing on the righteousness of a company, firms might consider aligning their incentives such that founder integrity is compatible with their investment thesis.

Triggering prompts must also be pointed at founders themselves, barbed most sharply at entrepreneurial culture. Entrepreneurship in the 20 and 21st century has been largely dominated by masculine norms, and has thus picked up bad habits of the boy’s club. With its undulating stone cold or boiling hot founders, the tech sector’s emphasis on cutthroat and hyper-productive work, along with its glorification of the hustle (see synonyms: fraud, swindler, unscrupulous), has bred a culture that further exacerbates problematic personality traits.

And of course, we must also ask ourselves as consumers why we are so captivated by their rise and fall, and if we’re willing to further endorse that arc. 

Critical snark aside, the entrepreneurial spirit — with all its peccadillos and shadows — is a forcing function in the trajectory of our human history, with the butchers, bakers, and candlestick makers of yore reflecting the startup founders, freelancers, and Etsy shop owners of today. Placing one’s iron in the fire of the creative economy, whether through a venture backed app or a cupcake shop, directly contributes to our social, psychological, and societal flourishing, and is a tradition that must be protected with the same vigor as any other conservation effort. 

While disagreeability will and should always be a part of this age-old tradition, this moment presents itself as an inflection point. Looking back on the last ten years, we can admit without hesitation: Mistakes have been made. And, as underscored by our pop culture fascination, the mistakes that will become legacy are not business mistakes, but human mistakes.

Mistakes like betting on the wrong horses and then doubling-down, even in the face of narcissistic, Machiavellian, and even psychopathic personalities. Or allowing toxic behavior — particularly of the masculine sort — to determine a company’s destiny. The time to rebalance the ecosystem is now, as the investments of today will become the headlines of ten years from now. 

So, pop your corn and derive some schadenfreude — a feeling of satisfaction in another’s failures — as the media chronicles what will inevitably be an ongoing series of meltdowns and downfalls. But keep some hope that we’ll soon kneel before a slightly more benevolent kind of American royalty.