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The Myth of the Maverick Founder

 2 years ago
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The Myth of the Maverick Founder

They’re still just people — and not always good ones

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Photo by Zac Durant on Unsplash

Over the years, I’ve met my share of CEOs, founders, entrepreneurs, and “visionaries.” What they all have in common is a deep, bottomless belief in their ideas and the will to make them happen.

They can be myopic, dismissive, unpredictable, but are also often charismatic, exciting, unusual. As they build their dreams, become successful, and gain notoriety, the public, if they see them — and they often do — start stripping away the things that make them average, human, and like us.

Steve Jobs might’ve been the best example. An average engineer, but brilliant designer and marketer, Jobs almost willed the Mac into creation. His failure soon after (ousted from his own company) was part of the Maverick journey and when Jobs returned in 1997, he soon willed more market-defining products, the new colorful Macs, iPod, iPhone, and iPad, into existence.

As adoring fans idealized Jobs, he modified his look, honing it into a uniform and presentation that was at once, completely recognizable but also enigmatic.

I think we all know that Jobs was much more complex than that. He could be harsh, angry, dismissive, self-destructive. He was just a man, perhaps an extraordinary one, but still flesh, blood, and bone.

Jobs and I never met, but I did have a few passing encounters with the Yin to Job’s Yang, Bill Gates of Microsoft. He was, in the 90s, similarly idolized by adoring Windows fans. I wouldn’t argue that he never rose to Jobs’ icon status. Jobs, who died in 2011, is frozen in time, his myth growing with each year since his passing. Gates lives and is revealed as more and more of the brilliant but utterly typical person he is.

Build up to break down

History is filled with founders and entrepreneurs who have built great things while preying on our weaknesses, and yet we’re constantly on the lookout for fresh inspiration, new leaders to idolize, and ultimately, tear down.

In recent years, our fascination with the maverick entrepreneur has shifted and with good reason. Where the legends of Steve Jobs and Bill Gates were built over decades, more recent founder stories are unfolding over the course of a decade, a few years, or even months.

And as quickly as we watch them develop and fly high enough to kiss the surface of the white-hot sun, their wings catch fire, and they tumble back to earth in a fiery ball of shame.

As an added benefit, we can read about them or watch them on countless mini-series either directly about them or in the thinly veiled versions of the failed entrepreneurs.

There’s the tale of WeWork and Adam Neumann, another charismatic founder who talked and talked his way into building a multi-billion-dollar shared space business until his tales collapsed around him and he was forced out.

People work in WeWork spaces to this day, but we’re already past idolizing the often-barefoot office space oracle and onto reading about his rise and fall in books and eagerly anticipating how Jared Leto will play him in an upcoming TV series.

I can still remember reading about Elizabeth Holmes and Theranos as far back as 2009. Back then, people believed the just-barely-an adult was on the precipice of saving thousands of lives. That she was emulating Steve Jobs was seen as a charming quirk and our desire for enigmatic leaders who would grow into icons seemed insatiable, especially in the wake of then-new stars like Facebook’s Mark Zuckerberg (always too nerdy to be a maverick), and Twitter’s Jack Dorsey.

Fast forward more than a dozen years and I’m watching Amanda Seyfried play the young Holmes in The Dropout as she transforms from an idealistic and hyper-ambitious inventor into a funding-obsessed mockery of Jobs.

The Hulu mini-series is, obviously, not the story of one college drop-out’s drive to save millions of lives with a unique blood-testing device. It’s a painful peeling away of the myth Holmes tried to build around herself and her company.

Over on Showtime, they’re screening Super Pumped, the tail of Uber and Travis Kalanick’s whipsaw rise and fall from entrepreneurial grace.

Uber was the simplest of ideas, an app-based ride-sharing management and transaction system that, for a time, people only needed a car and willingness to endure stranger passengers to use. Unlike some earlier idolized founders, there were signs early on that Kalanick was rougher around the edges than your average maverick. Like most, he didn’t suffer fools gladly, but he also assumed that he could remake the world in his vision of transportation without accommodating those that came before him.

When I saw him speak at a Code Conference in 2014, he was pressed on negotiating with taxi services, groups his business was undercutting on price and availability and hurting. He casually called them “assholes.” A few years later, his roughshod approach and charges of sexual harassment led to calls for his resignation and him eventually leaving the company he founded.

In Netflix’s Inventing Anna, which is the mostly true story of the fake socialite Anna Delvey, there is embedded in it another cautionary maverick founder tale.

The show depicts a guy named Chase launching a sleep and dream recording app, Wake. Like any good 21st-century tech visionary, Chase starts with a TED talk where he delivers his vision for Wake, an app that helps you track and record your dreams.

In the series, Chase globe-trots with Anna collecting investor funds until he disappears and reemerges in Saudi Arabia advising the Saudi Prince

Chase is loosely based on Hunter Lee Soik, who gave a TED talk in 2013 for his app, Shadow, which also helped people record dreams by slowly waking them up and asking them to put down fresh recollections from their dream states.

Soik’s app is long gone, and, like Chase, he ended up thousands of miles away from the app scene, in Dubai. Having failed to achieve Jobs, Holmes, or even Kalanick maverick status, he’s ultimately just a side character in the Delvey story.

Idol worship

All these tales are reminders of the dangers of idolatry. The sometimes strikingly similar stories depict our desire for visionaries to lead us forward and our failure to take note of or believe warning signs that reveal the mavericks for the flawed people they often are. Inevitably, this myopia leads them, and sometimes us, to ruin.

For all these tales of failed founders/leaders, there are many who operate and thrive and that we look at with a mix of admiration and concern.

Elon Musk whom I first met in 2012 is someone who walks a tightrope of concrete creation, innovation, and personal calamity. Unlike mavericks of the past, Musk’s personal life is almost always on full display to such an extent that it can obscure his very real accomplishments. Perhaps in another time, we might only have seen the booming Tesla, space-race-changing SpaceX, and moonshots like Neural Lace.

However, Musk and modern mavericks like him operate in a media-saturated landscape that will sweep up the important and the causal, the momentous and the embarrassing, the business, and the personal.

The new perspective on maverick founders is that they are less career and business exemplars than cautionary tales and fodder for our entertainment.

They’re also just people.


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