In the middle of the slick new TV series WeCrashed, WeWork founder Adam Neumann (played by Jared Leto) is asked by Masayoshi Son (Kim Eui-sung), CEO of Softbank, WeWork's biggest backer: "Who wins in a fight? – the smart guy or the crazy guy?"
Neumann doesn't take long to reply: "The crazy guy."
Son says: "You are not crazy enough. Do you understand?"
Spurred by Son's words, Neumann and his team go on a rampage: They burn through millions of dollars every day, buying up leases at above-market rates to eliminate WeWork's competitors and dominate the co-working sector. All these helped hasten the meteoric decline of the company once touted to be worth US$47 billion.
WeCrashed stars Jared Leto and Anne Hathaway as WeWork founder Adam Neumann and his wife Rebekah.
The conversation between Neumann and Son took place in March 2017 and was retold by Neumann to Forbes months later. It is now fully dramatised in Apple TV+ series WeCrashed, which chronicles the rise and fall of the co-working startup WeWork, using an all-star cast and splashy locations.
(For the record, Son eventually plotted to remove Neumann from his CEO position because Neumann had become "too crazy".)
WeCrashed isn't the only high-profile TV drama about startup disruptors to debut recently: Disney+ has The Dropout which stars Amanda Seyfried as Theranos founder Elizabeth Holmes, once hyped as the youngest self-made female billionaire. And Showtime has Super Pumped, centred on former Uber CEO Travis Kalanick, played by Joseph Gordon-Levitt. (Showtime is not available in Singapore.)
SATURDAY NIGHT LIVE -- "Elon Musk" Episode 1803 -- Pictured: Host Elon Musk during the monologue on Saturday, May 8, 2021 -- (Photo By: Will Heath/NBC/NBCU Photo Bank via Getty Images)
Elon Musk on Saturday Night Live last May, dressed in a Givenchy suit designed by Matthew Williams.
Startup founders don't just make for great cover stories in newspapers and magazines. They're also perfect characters for the screen, big and small. The best of them have mastered the art of public persuasion and media manipulation, and they exude a larger-than-life personality rivalled only by, well, movie stars.
As tech gurus like Elon Musk and Jeff Bezos appear on red carpets with glamourous arm candy, the leap from Silicon Valley to Hollywood has become a short one. And when their story arcs involve both rapid success and failure, they're catnip for the screen.
In the first episode of WeCrashed, Neumann is depicted as a struggling small-time salesman peddling baby clothes and women's shoes. But by the end of the episode, he's lucked out, making US$500,000 selling his first co-working space Green Desk with his partner Miguel McKelvey.
By Episode 2, he's married a beautiful yoga instructor, bought a five-bedroom apartment in Manhattan and attracted major investors with his vision of changing the "future of work" with WeWork. He's soon jet-setting around the world, having his lunch flown in from Michelin-starred restaurants, hiring rappers to perform at lavish office parties, and buying beachside properties to the tune of millions – despite WeWork's obscene cash burn rate.
In a dazzling performance that redeems his much-criticised one in 2021's House Of Gucci, Leto plays Neumann to the hilt, amplifying his narcissistic magnetism and eccentricities. The real-life Neumann is tall, handsome and confident – but Leto takes his charm to messianic levels, helping us understand why so many people bought into Neumann's vision in the first place.
But neither Neumann nor Leto could have done it without a woman beside them: Anne Hathaway gives a riveting performance as Neumann's tenacious wife Rebekah Paltrow Neumann. It is Rebekah, a New Age vegan yoga instructor, who provides Neumann with the spiritual guidance to convince people to buy into his dream. Neumann could talk about how WeWork could "manifest your dreams", "discover your superpower" and "elevate our global consciousness" without sounding false - because he genuinely believed what his wife believed.
Together with McKelvey, Neumann and Rebekah (pictured) were able to build a cult-like culture in WeWork where the staff spent long hours in the office in extreme dedication to a cause bigger than themselves. And while that culture was sometimes dressed up for the benefit of visitors, it fooled enough investors into giving millions and billions to WeWork.
Although WeCrashed doesn't go deep enough into examining why WeWork failed beyond the Neumanns' pride and greed, it's still the most lavish and caustic corporate satire of the year so far, poking fun at the wild pre-pandemic startup era that saw money sloshing around like an oil spill in the Gulf of Mexico
In contrast, The Dropout on Disney+ does away with the frills and flourishes in charting the rise and fall of Elizabeth Holmes (played by Amanda Seyfried) and her company Theranos.
While WeCrashed condenses Neumann's early struggles in favour of his glitzy subsequent life, Holmes' journey towards becoming a technopreneur is shown to be riddled with earthbound struggles – unpopularity at school, poor fashion sense and a general inability to vibe with people.
What marks her out from the other students is her all-consuming ambition to be the next Steve Jobs. When she drops out of Stanford University, she tells people that Jobs also dropped out of college. What she doesn't tell them is that she was sexually assaulted at a fraternity house, forcing her to leave Stanford.
Whereas Neumann is depicted as a preternaturally gifted spinmeister capable of whipping up messianic fervour among his listeners, Holmes is shown as an awkward young woman with a chip on her shoulder, shunned by peers and ridiculed by authority figures.
It is partly the romantic, emotional and professional support of Ramesh "Sunny" Balwani, a Pakistan-born businessman 19 years her senior, that pushes her to brush up on her public image and pursue her goals systematically.
She lowers her vocal register, starts dressing in elegant black turtlenecks a la Jobs, and maintains prolonged unblinking eye contact as methods of persuasion.
But her relationship with Balwani was also abusive and violent, which affected her ability to think through her decisions.
Seyfried (pictured), a performer not quite the calibre of Hathaway and Leto, is convincing, but far less charismatic than Holmes herself.
It's hard to think of an actress who can capture Holmes' hypnotic stare, which has single-handedly generated hundreds of online stories and comments. (Jennifer Lawrence, set to also play Holmes in an upcoming Adam McKay film, will certainly try.)
What The Dropout does particularly well, however, is depicting how much harder it is for a woman to succeed in Silicon Valley. In the early days of Theranos, Holmes is frequently asked to dress up for the job, or criticised for looking "tired".
The incident of sexual assault at Stanford is also never resolved, suggesting a deep unspoken trauma that Holmes has to deal with on her own, after her own mother tells her to "just put it away and forget it" because "men will take and take from (a woman)". Even after Holmes learns to use her gender to her advantage, it remains a double-edged sword.
Previous biopics of technopreneurs such as The Social Network (2010) and Steve Jobs (2015, pictured) do not depict the world of venture capitalists and big bankers who now crowd the startup space.
WeCrashed and The Dropout show Neumann, McKelvey and Holmes constantly negotiating with board members and investors, and it is to these shows' credit that the meetings in bland rooms are shaped and dramatised to be nail-biting affairs.
WeCrashed even has interludes featuring business professor Scott Galloway (from The Prof G Show) explaining concepts such as IPOs to non-financially inclined audiences – a la the interludes in Adam McKay's The Big Short (2015) where celebs like Anthony Bourdain and Margot Robbie explain collateralised debt obligation and sub-prime mortgages.
Amusingly, Katy Perry's songs loom large in both WeCrashed and The Dropout: In the former, Neumann listens to Perry's Roar to convince himself he's a winner; in the latter, Walgreens medical adviser Dr Jay Rosen listens to Perry singing "Do you ever feel like a plastic bag/Drifting through the wind…" before making an attempt to persuade his sceptical CFO Wade Miquelon to invest in Theranos.
He tells the latter: "There are kids here running billion-dollar companies. It's a new world. These kids don't overthink. They don't get bogged down in the way things used to be done… We're old, Wade. We're dinosaurs."
Walgreens ultimately invested – and lost – US$140 million in Theranos. There's a lesson here about trusting inspirational songs by Katy Perry.
Stories of hubris, greed and excess leading to a downfall have been told since time immemorial, from the tragedy of Adam and Eve to the myth of Icarus, from Macbeth to The Great Gatsby in the Baz Luhrmann's film adaptation). These disruptor stories are just the latest in a long line of cautionary tales.
The difference, however, is that we live in a new economy that allows these savvy 21st century losers to still emerge winners: Neumann walked away with US$480 million in settlement after playing a game of who-blinks-first with Softbank.
Holmes – the woman who hardly blinks – met hotel heir Billy Evans in 2017 and married him in 2019. In February 2022, they welcomed their first child.
A version of this article first appeared in The Business Times