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How To Decode The Sudden Boom Of Start-Up Failures On TV

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What’s with the rapid influx of dramatized series on collapsing start-ups? In the last couple of months, prestige series have aired on struggles at Uber, WeWork, and Theranos.

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Emily Jashinsky: What’s with the rapid influx of dramatized series on collapsing start-ups? In the last couple of months, prestige series have aired on struggles at Uber, WeWork, and Theranos, drawing top talent like Anne Hathaway, Jared Leto, Joseph Gordon-Levitt, and Amanda Seyfried. 

The shows are all captivating, too. Obviously, we’re in the midst of a true-crime boom and each series depicts some dubious legal behavior. And obviously when a lot of companies soar at once, a lot are going to crash.

There was something about the combination of the economic climate and technological advancements during the Obama years that seemed to fuel this cycle. So it just that simple? They rose, they fell, and now enough time has passed to make shows? 

Some people would say that cycle reflects the beauty of the American free-market system—for every success story you have a Theranos or a WeWork. Risk takers like Travis Kalanik are innovators and an inevitable part of the ecosystem. But is there something else going on here in 2022 with a lot of these fallen mighties in the rearview mirror? 

Madeline Osburn: I would suggest the boom is bigger than just Silicon Valley and start-ups, although that’s definitely a great place to find interesting characters. It’s really about the influx of high-profile fraudsters that seem to have dominated our news feeds in recent years. 

So in addition to multiple series about Elizabeth Holmes and WeWork, we are also seeing series like “Inventing Anna” and documentaries about Fyre Festival, “The Tinder Swindler,” and Operation Varsity Blues. In every case, the true story is more captivating and jaw-dropping than what any screenwriter could come up with, which is why there are as many documentaries as there are dramatized series. 

My theory is these fraudsters’ stories, especially in Silicon Valley, are entertaining little anecdotes for the larger themes about how elite society and institutions are cracking at the seams. Sure, we have big stories like Brexit, Donald Trump, Jeffrey Epstein, and Covid that all have their place in pulling back the curtain, but in some ways, the story of a single start-up founder’s dubious legal behavior is a much easier way to digest the collapse of society and the puppet masters behind it. 

EJ: Okay, you just made a great point. These stories captivate us 1) because they’re genuinely interesting but also 2) because they fit into this emerging broader narrative. 

As a country we seem to be working through exactly what that narrative is and what to do about it. One thing seems clear: It’s very American. It’s the “work hard, play hard” mentality, but with “playing hard” defined in the Fyre Festival sense. Luxury beyond our ancestors’ wildest dreams, potentially available to anyone with a college degree and a good work ethic. (Or, of course, a trust fund.) The LuLaRoe documentaries showed this too.

Anna Delvey wanted that life so badly, she put in a crazy amount of work just to fake her way to the top of New York City. She forged bank documents! The Tinder Swindler story isn’t American but it still showcases people’s desperation. Women wanted to go on a private jet so badly, they accepted the invitation from a stranger. 

All that is to say, so many of these lies are built on people’s bad investment decisions. Theranos is a great example of that. And when we have elites with obscene amounts of money swirling around and major industries increasingly relegated to screens, things almost start to feel like the Sims. And that’s where an Elizabeth Holmes comes in, scoops up tons of cash from easily duped rich people, and builds a house of cards. 

MO: Yep, and that’s why I would argue that out of all these crazy stories, (I mean—Lori Loughlin staging photos of her daughters on rowing machines to get into the University of Southern California is insane) the Theranos story is the most captivating, and the one that’s been retold the most with multiple documentaries, movies, and series. 

You have names like Henry Kissinger, James Mattis, and George Shultz who were all on her board, not to mention investors like Rupert Murdoch and Walgreens who overlooked their due diligence so they could get in on the “next thing.” If those names and institutions can be duped by Holmes’ “science,” then what else are our most elite leaders being duped by? 

And you’re right about screens. There is something ironic about how our screens and technological advancements are making us much more gullible as a species. 

EJ: It’s this sense that people like Adam Neumann are living off gains that feel like monopoly money, which also makes them more likely to spend it frivolously and lavishly. So much of the economy feels divorced from reality, and whether that’s mathematically accurate, it feels accurate. And I think that explains why these stories are so compelling. 

MO: Nobody does fraud, and then makes movies about that fraud, better than America.