The Dropout, Super Pumped, and WeCrashed: How Silicon Valley scammed spring TV

Three new docudramas about Big Tech scandals share a premise—and a paradox

TV Features Super Pumped
The Dropout, Super Pumped, and WeCrashed: How Silicon Valley scammed spring TV
From left: Jared Leto and Anne Hathaway as Adam and Rebekah Neumann in WeCrashed Photo: Apple TV+

If good things should happen to good people–and bad things should happen to bad people–then whose lives should be made into TV shows? That’s the question posed by three splashy (and equally problematic) Big Tech docudramas playing out this spring.

Disgraced disruptors Elizabeth Holmes, Travis Kalanick, and Adam Neumann are making headlines again as Hulu’s The Dropout, Showtime’s Super Pumped: The Battle For Uber, and Apple TV+’s WeCrashed adapt the ex-CEOs’ oustings into episodic character studies—all starring A-list actors.

Amanda Seyfried anchors The Dropout as Theranos founder Holmes, whose medical testing company doubled as a dangerous fraud. Joseph Gordon-Levitt stars in Super Pumped as former Uber CEO Kalanick, who resigned amid allegations at the height of #MeToo. As for WeCrashed, Jared Leto and Anne Hathaway appear as the hard-partying Neumann and his wife Rebekah, whose shared narcissism all but destroyed their co-working startup WeWork.

If good things should happen to good people–and bad things should happen to bad people–then whose lives should be made into TV shows? That’s the question posed by three splashy (and equally problematic) Big Tech docudramas playing out this spring.

Each limited series (or, in the case of Super Pumped, self-contained season of a planned anthology) adapts a book or podcast, summarizing months of news stories and market mania that unfolded in real-time not so long ago. To make matters even more redundant, The Dropout and WeCrashed were beaten to market by documentaries The Inventor: Out For Blood In Silicon Valley and WeWork: Or The Making And Breaking Of A $47 Billion Unicorn, released in 2019 and 2021 respectively.

This sort of narrative double-dipping tends to dilute source material and alienate audiences. But the promise of highly skilled TV stars skewering Silicon Valley helped transform the scheduling coincidence into something of a pop culture event. First-looks revealing outrageous prosthetics and trailers teasing unblinking eyes arrived like sideshow advertisements, all but commanding: Come see the altruistic heroes of Hollywood fight the fiendish freaks of big business–now via caricature!

Seyfried, Gordon-Levitt, Leto, and Hathaway are the right actors to do it, to be sure. Their performances are funny, well-informed, and smart (as was to be expected from these award-winning ringers). And yet, there is an underlying paradox in this trio of titles: By putting some of Silicon Valley’s most notorious wrongdoers back on screen, isn’t Hollywood celebrating their misdeeds–even unwittingly?

For every boardroom embarrassment, there is a spare-no-expense rager; for every crisis of confidence, a self-assured jam session; for every fall from grace, a view from the top of the world.

Storytelling requires highs and lows, meaning that characters (no matter how detestable) must experience change. Here, that means audiences must watch as true-to-life tyrannical titans of industry rack up as many brag-worthy wins as they do cataclysmic losses. For every boardroom embarrassment, there is a spare-no-expense rager; for every crisis of confidence, a self-assured jam session; for every fall from grace, a view from the top of the world.

To get to the declines of Holmes, Kalanick, and the Neumanns, we must first weather their reward-laden rises—a frustrating way to ensure some viewers only ever see the victories. Super Pumped’s third episode, for example, centers on Uber’s never-ending pissing contest with Lyft. It’s practically an end-zone dance for Kalanick, whose business strategies worked wonders on that one problem at that one time.

Similarly, when we are taken back to the entrepreneurs’ origins–namely, the impassioned speeches in which they first made utopian promises to their employees and investors–these would-be Bill Gates look less like liars and more like wunderkinds led astray. The revolutionary ideas they first spoke to are extra compelling against the backdrop of the ongoing Great Resignation. Think Mark Zuckerberg’s relentless refusal to accept the Harvard establishment, as seen in David Fincher’s (increasingly out-of-touch) The Social Network, and you get the idea.

You don’t root for Holmes, Kalanick, or the Neumanns in quite the same way you might have once admired the flip flop-wearing wunderkind played by Jesse Eisenberg. But that’s because each show grapples with the ethical slipperiness of its subject matter differently—and with varying degrees of success.

You can almost picture Kalanick cracking open a cold one while marathoning JGL’s meanest monologues.

WeCrashed morphs the Neumanns into farcical creatures of high-camp, making their happiest moments into cringe-inducing displays of tone deafness. Super Pumped blurs the lines of reality and fantasy, letting Kalanick’s Goliath vision of himself give way to a fighter not half as smart as David. The Dropout plays Holmes as a hyper-driven sociopath, giving Theranos’ intense business arc the breakneck pacing needed to match her rapid psychological unraveling.

These strategies toward nuanced portraits of interesting figures work some of the time. Still, it’s painfully easy to imagine the shows’ living-breathing inspirations enjoying lighter scenes and even being happy they exist at all.

You can almost picture Kalanick cracking open a cold one while marathoning JGL’s meanest monologues—or envision the Neumanns, lounging in their still-perfectly agreeable living quarters and soaking up comparisons to WeCrashed’s very good-looking lead actors. Maybe Holmes is the odd one out, considering she’s still facing prison time. But an exciting new personal connection to Mamma Mia! counts for something, right?

These heavy silver linings for Holmes, Kalanick, and the Neumanns reflect an irritating imbalance inherent to Silicon Valley villains. Self-important public figures with this much power tend to play outsized roles in their victims’ lives—a dynamic that too often continues even after the evil-doers’ comeuppance. Now, Hollywood is forwarding that regrettable reality by retelling these all-too-recent true stories as glossy portraits that prioritize the villains over the people they harmed—when it should probably be the other way around.

22 Comments

  • killa-k-av says:

    To paraphrase David Harbour, “Yeah, you’re right. We should only make TV shows about nice people.”The only “docudrama” of the three above that I’ve gotten a chance to see so far is WeCrashed, and so far I’m enjoying it a lot. Leto and Hathaway are turning in great performances, but Jared Leto is kinda’ creepy-lookin’ with Adam Neumann’s signature long hair. I’m not sure if his age plays a part, because more than once I’ve been reminded of Tommy Wiseau.

    • bcfred2-av says:

      I haven’t seen it yet (did listen to WeCrashed), but that one stands a bit aside for me because the Neumanns weren’t perpetrating frauds on their customers or investors, or sexually assaulting employees. They were just delusional egotists who thought their office subleasing business was really a tech, lifestyle and education company all rolled into one – and somehow got other people to believe it. They burned insane amounts of cash expanding the business using a terrible business model (I know a guy whose small company resided rent-free in two different WW locations for a year on new tenant promotions) but ultimately it feels more like a story about a cult.

      • killa-k-av says:

        That’s the same sense I’m getting. It’s kinda’ funny; I watched a trifecta of documentaries around the same time last year – the Hulu WeWork documentary, the Netflix Fyre Festival doc, and a Theranos doc – and it was jarring to see people talk about Billy McFarland and Elizabeth Holmes as if they are these spell-binding, persuasive hucksters. The documentaries show footage of them and neither of them seem particularly charismatic or likeable. They almost seem meek. But the footage of Adam actually conveys how he could seem charming in person.What I like about WeCrashed is that it shows why someone would invest in him in a much more intimate way than the documentary can show. But if you take a step back and examine how, he’s absolutely using the same techniques as a cult leader.

  • adamtrevorjackson-av says:

    i think ‘the dropout’ is shaping up to be an excellent season of tv but the fact that all 3 of these are running concurrently is so funny. 

    • ohnoray-av says:

      The Dropout is amazing, and I think it is examining the people Elizabeth hurt more and more with each episode. It wants the audience to buy in as well to a degree to Holme’s, and then remind you that this person caused a lot of hurt.

  • hiemoth-av says:

    While I think overall this is a valid criticism and I do think this certainly applies to Super Pumped where it does juggle more about who Travis is. However, I would argue The Dropout is absolutely brutal towards Holmes from the very first episode. Even to the degree that in their version they present it ultimately all being Elizabeth and her need to be great. What I think separates it from the other two is that it also focuses on a lot on the lives she destroyed and thus never allows you to look away from the wreckage she left behind. That’s where Super Pumped falters a bit as it seems to be holding back on the negative side of Travis.
    Seriously, that Apple Genius bar speech in episode 3 was such a chilling revelation on who the show saw Elizabeth as.

  • bcfred2-av says:

    Curious how The Social Network is increasingly out of touch. I felt it did a great job of showing that Zuckerberg was very much the asshole that Holmes and the like later presented to be. He did steal the Winklevoss brothers’ idea, piggybacked off Eduardo’s math skills and seed funding, and then threw the latter under the bus as partner and CFO to secure a better financial deal for himself. There are some moments where he impresses (the attorney meeting is absurdly well-written) but by the end he’s sitting alone in Facebook headquarters updating the total users count. If the implication is that Facebook has morphed into something different that is probably a net negative to society, you’ll get no argument from me.  But overall I’d call TSN very much a companion piece to these shows.

    • teageegeepea-av says:

      I think TSN is out of touch because it’s Sorkin’s concerns rather than Zuckerberg’s. It’s ending is fictional and Zuckerberg was fine with how things turned out, although he also appears to have gotten bored with success and itched to move on to new fields to conquer.

    • captain-splendid-av says:

      The Social Network is horror movie, not a docudrama.And it still holds up, IMO.

      • cowabungaa-av says:

        It holds up but desperately needs a sequel. Facebook as a company, and probably the whole corporate structure and whatnot, is nothing like what we see in The Social Network any more.

    • dinoironbody1-av says:

      I’d say the movie is less out of touch than the reactions of people who thought it’s depiction of Zuckerberg was too harsh.

  • hootiehoo2-av says:

    I’m so fucking old that I had no fucking clue what WeWork is and I have lived in New York for 48 years and work near Wall Street for almost 15 years and there is a WeWork near my office and I still have no fucking clue what the fuck this place is. My buddy explained it to me saturday night and I still go “wait what?”

  • teageegeepea-av says:

    Uber seems like the odd company out in that it hasn’t crashed but it still going on without its former CEO.

    • snooder87-av says:

      Probably because unlike the other two, Kalanik’s problem was being too much of a techbro dick rather than being a fraudster or a liar.

  • scortius-av says:

    Whatever. Fuck all of these people. I never need to hear about any of them ever again. They are horrible in too many ways to list here. But also, they wasted billions of dollars of rich people, hedge funds and VCs. So HA HA on those people. I’m slightly torn.

  • maulkeating-av says:

    Series about techbro douchebags, eh? When are we getting one about this dude?

  • windshowling-av says:

    Haven’t seen Super Pumped or WeCrashed yet, but The Dropout pulls no punches. It buries Holmes as a flat-out evil sociopath who was only able to succeed because of the stupidity of the money-men around her. Its both an indictment on her and on the culture of Silicon Valley without a single moment I interpreted as being sympathetic, within the first 5 episodes so far. 

  • volunteerproofreader-av says:

    unfolded in real-time —> unfolded in real timethese would-be Bill Gates —> these would-be Bills Gatesfarcical creatures of high-camp —> farcical creatures of high campevil-doers’ comeuppance —> evildoers’ comeuppance

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