Trump the Entrepreneur: Why Startup Culture Is Failing Us

Founders. Entrepreneurs. Change-makers. Rockstars.

These terms have become virtually-interchangeable monikers for a lionized breed of “self-starting”, “scrappy” “visionaries” who are the heroes of the moment, at least insofar as they are concerned.

Entrepreneurial aggrandizement is both ubiquitous and well-documented. The American Dream has been reborn in countless guises, and tech entrepreneurialism is merely the latest. We want to believe entrepreneurs are special. We tell ourselves that they take risks no one else would take, endure stresses others avoid, have to solve problems that are too hard or too terrifying for others to confront.

Sure, they can be a little self-involved — and when they’re brilliant, outright assholes (a la Steve Jobs) — but it’s just a charming function of their unique constitutions and compositions. It’s what allows them to be great. All is forgivable, if the business grows.

In reality, the ruthless lionization of startups and startup founders has become completely toxic. Society has come to view the hope and change they represent as so precious and meaning-rich that their efforts somehow assume a rarefied form, exempt from established moral frameworks.

And it is within this troubled frame that Donald Trump is, in many ways, the ultimate “entrepreneur”. For Donald, as with so many tech founders, it’s about “results” — not ethics, or representation, or rule of law. And when we say results, what we really mean is the apperception of results. Trump has continually bankrolled the notion that he is “successful” into more money — which, by the way, is exactly how entrepreneurs are encouraged to grow their companies. Is he actually successful? He won’t actually tell us, and many don’t seem to actually care.

Fake it until you make it. Raise money against dream. Outmarket, outsell, and pick up the pieces later. Sure, Trump resides in the theater of our political discourse now, but it’s not a particularly far cry from the theater of venture-backed entrepreneurialism. Self-important founders raising millions of dollars with a rickety balance sheet and a PowerPoint. Fueling anticipated breakthroughs and overcoming “rough spots” with yet another cash injection. Chasing PR and general recognition above all else. Letting sales drive your roadmap.

It’s all the same approach, the same method of value creation, “results” fueled by fake money and self-important visions. Just as Trump took the presidency through absurd, self-aggrandizing bombast and bullshit, companies like Theranos secured hundreds of millions in funding, built partnerships with massive companies like Walgreens, and legitimately put lives at risk — all without ever putting themselves through a peer-review, or anyone (investors, advisors, or executives) pulling the emergency brake.

Trump’s now “legitimate” bloviating grandiosity is not a far cry from those of the tech industry’s success stories. We have founders and investors who believe they are above the press. Founders who build hostile work environments that demean and terrorize employees. In today’s startup world, women and minorities can feel equally under threat by their government, and the white, male-dominated milieu of the glittering “unicorn” or fledgling startup at which they work.

And both Trump’s presidency and entrepreneurial ventures consciously position themselves as inherently populist, while ultimately implying a more insidious form of absolute power. Trump ascended to the presidency on a platform predicated on creating jobs, disrupting the status quo, alleviating poverty, being more “agile” by doing away with unnecessary bureaucracy. In reality, he has done little besides dismantle frameworks designed to protect and support the needy, while transparently advancing legislation that results in his own enrichment, and that of his close family, friends, and class.

Sound familiar?

Venture-backed startups also sell the dream of shared enrichment and “greatness” — which, for a fortunate few, does occur — while leaving the vast majority of startup employees with below-market salaries and worthless stock options. Nine in ten startups fail. For those that manage to muddle through, it is ultimately almost always the founders who become obscenely wealthy and famous on the backs of their underappreciated employees. Too many startups have been acquired under terms that leave their employees behind, restarting their equity clocks or rendering their shares outright worthless.

More recently, startups attached to the “gig” economy have created an even more unstable and dehumanizing work environment, in which everyone is a contractor and equally expendable relative to the brand and technology. This entire dynamic creates a fundamental hubris that feels particularly “Trumpian” — a world in which one’s success — or “success” in business somehow creates a legitimate platform for solving any problem.

For example, a friend of mine runs a non-profit focused on gun-control. He and his team went to major cities — Chicago, NY, Miami, etc — and raised money from the usual suspects there. Super high net worth individuals looking to give back to a particular cause. These conversations, he noted, were often characterized by the signing of a check and genuine curiosity about the best way to help.

When they arrived in SF, they met with a group of wealthy “technorati” that were interested in supporting the cause. And what stood out to him is how a.) poorly informed they were and b.) how interested they were in telling him exactly what he was doing wrong. This sort of self-determined, woefully-misguided faux omniscience is exactly what we see in Trump’s bearing and approach around critical issues like health care. Because I have money, because I get “results”, I am correct and I can do what suits me. Facts do not matter. Intelligence does not matter. Actual results do not matter. “Results” matter. My brand of succeeding and getting those results, matters.

This is not to say, of course, that entrepreneurs as a general rule are as depraved as Trump, as toxic as Trump, or as likely to realize societal harm. However, as we collectively continue to reckon with the horrifying potential of a Trump presidency, there has been significant soul-searching about what conditions may have given rise to his election. I would suggest that those of us in the world of technology take a long, hard look at the behavior we encourage, the way we treat those around us, the dynamics we promote, and the level of personal responsibility we take. We might find that there is substantial room for improvement.