What WeCrashed and Super Pumped highlight about TV’s love for the big bad entrepreneur

Anne Hathaway isn’t stupid.

Even a few seconds into an interview for WeCrashed, she knows what we’re thinking. It’s the same thing everyone’s thinking: The miniseries about Adam (Jared Leto) and Rebekah (Hathaway) Neumann’s $47-billion US company WeWork and its precipitous fall is eerily similar to all of the other miniseries coming out about what is essentially the exact same thing.

Inventing Anna, Netflix’s take on a phoney German heiress and attempted founder of the so-called Anna Delvey Foundation, was released in early February. Super Pumped, about the embattled CEO of Uber, premiered only a couple of weeks later. The Dropout, which told the true story of Elizabeth Holmes’s fake blood testing company, arrived on Disney+ on March 3.

And Hathaway’s, another series about a madcap entrepreneur ranting about their ability to change the world, followed in their footsteps on Friday.  

“You’re crushing my soul,” she said when it’s pointed out. “But thank you.” 

WATCH | Anne Hathaway on WeCrashed and TV’s startup obsession

Anne Hathaway on WeCrashed and TV’s startup obsession

Actor Anne Hathaway describes how the Fyre Festival documentary convinced her to star in WeCrashed, and explains why the WeWork story piqued her interest. 1:09

With so many major studios betting big on these stories, it’s a hard trend to miss. Something about the charismatic manipulator sweet talking their way into — and unsuspecting dupes out of — unimaginable wealth, before crashing spectacularly down to Earth, has us hooked. 

And while the idea isn’t exactly new, it’s worth asking: Why are we virtually drowning in these stories now? What about them makes creators (and, arguably, viewers) so obsessed? And are they even getting any of it right?

Entrepreneurs make great TV

In terms of getting it right, in many ways they’re pretty close. The idea of a multibillion-dollar company built almost entirely around the personality of a single individual before — or even instead of — an idea is based in reality.

Penelope Trunk — businesswoman, author of numerous books on entrepreneurship and a five-time startup founder — said the thing investors usually look for in a founder is the same thing that makes great TV: someone so preoccupied with a goal that they’re not only willing to but forced to focus on the success of their idea against basically anything else in their life.

Trunk explained all of that on the phone while yelling at someone nearby who was apparently yelling right back at her.

Julia Garner stars as Anna Sorokin in the Netflix series Inventing Anna. It’s another story about an (attempted) entrepreneur with near super-human drive. (Nicole Rivelli/Netflix)

“You hear my life? This is my life,” she said. “I can’t do life. All I can do is startups.

“But that’s what investors invest in. They don’t invest in that I can function for one minute in my life, because I can’t. They don’t go together. Like, of course, if you can function in your life, you wouldn’t destroy your life to do a startup.”

That makes for inherently good TV and interesting characters for actors to brush up their reels. With method acting on the ropes and portrayals of real people a seemingly surefire way to success on the awards circuit, echoing the neurotic actions and apparently necessarily outlandish accents of any of these characters is an appetizing opportunity.

And the fact that it’s all somewhat true is just a bonus.

The generally weird behaviour of the characters is well established as well. Adam Neumann did often go barefootBad Blood author John Carreyrou argued Elizabeth Holmes “absolutely has sociopathic tendencies” in a Vanity Fair interview; and Anna Delvey truly did refuse to appear at her trial (multiple times, in fact) because her wardrobe didn’t suit her preferences.

Trunk said oddities and self-destructive tendencies among this group is common in real life as well. Trunk, who herself has autism, said neurodivergence is overrepresented among entrepreneurs. And though none of the mentioned founders have been diagnosed (or shared their diagnoses) with similar disorders, similar associations have been observed — and even Tesla-founder Elon Musk recently shared he is on the spectrum.

Trunk said that’s because traits like ADHD and autism draw in single-minded, particularly driven individuals who struggle to fit into traditional workplaces.

“When people look at all the founders who fail,” she said, “those founders have been failing at everything except big ideas and [have been] super-focused their whole life.”

TV shows often ‘amplify the extremes’

Then there’s the other side. Where these series show entrepreneurs building something from nothing, they’re doing so at the expense of duped investors.

Andre Charoo, a Canadian venture capitalist (VC) and founding partner with Maple VC, said aside from the fact that writers and creators clearly picked extreme cases for their shows, the events themselves are emphasized in specific ways, for a specific effect.

While investors often start out investing in ideas and a business can fly by the seat of its pants, things quickly even out as VCs demand more oversight. As businesses naturally grow, they quickly move from the ideas and salesmanship phase, and rooted directly in the manic but effective personality of the founder, it quickly becomes more about the business than what the leader can sell.

Amanda Seyfried appears as Theranos founder Elizabeth Holmes in a scene from The Dropout. Holmes was convicted of conspiracy to commit fraud after misrepresenting the abilities of her company’s tech. (Disney+)

While audiences get a thrill from seeing oblivious fatcats talked out of their money by a rags-to-riches type, Charoo said these shows often elide these highs and lows, “amplify the extremes of both spectrums” and make the whole journey look like a deck of cards ready to topple at any moment rather than just the beginning stages.

For example, Charoo was one of the first 25 employees at Uber and helped to eventually bring the company to Canada. While he saw the order of events in Super Pumped was clearly manipulated, what stood out to him the most was Uber’s office.

In the beginning, he said, nothing looked as clean or professional as it’s depicted in the show — an image of efficiency that pitches CEO Travis Kalanick as a Steve Jobs-esque hero of the tech movement before they’d even gotten started.

“There was so much written about the story and the journey and both highs and lows,” Charoo said. “And so those highs and lows are being packaged in a story made for television that puts the timeline out of whack, the characters out of whack. Like, it’s not a full representation.”

An old archetype

That framing is nothing new. While Charoo said we’ll likely get more such stories because business “unicorns” (private companies valued at more than $1 billion) are more common in the digital age — while the companies that do reach these enormous prices are also more a part of our daily lives for the same reason — the archetype is already well established.

When The Wolf of Wall Street first premiered (as critic Esther Zuckerman wrote at the time), the more Leonardo DiCaprio played up the debauched acts of his fraudster lead, the more audiences seemed to root for him. And while he was beloved in Catch Me If You Can for portraying the real-life Frank Abagnale Jr., ingeniously eluding the FBI for years, a recent investigative book argued that almost all of Abagnale’s claims were inflated to earn fame and adulation. 

So why do we love the startup story? 

Dr. Michael Freeman is an entrepreneur, author and clinical professor of psychiatry at the University of California San Francisco School of Medicine who conducts research on the mental health of entrepreneurs. He said that while their mindset is often “systematically different” from job-holders, that’s not the reason we’re drawn to the startup story.

We’re drawn because the way it’s shown isn’t true to life.

“What’s true about entrepreneurship is that it does tend to be an emotional roller-coaster,” Freeman said. “These shows are really about characters who are much more spectacular … messianic or sociopathic or something like that, which is not true of most entrepreneurs.”

Instead, the startup shows are just riding a wave of high-profile stories available to adapt — and our unique, but strange, tendency to root for a hustler as long as they’re confident, no matter how many lives they destroy.

As to why we like that? That’s for greater minds to consider.

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