Dear Reader,
In March of 2022 we were served up not one but three high-budget limited series about start-ups that went off the rails – The Dropout (Theranos), Super Pumped (Uber), and WeCrashed (WeWork).
Why did they all arrive at once, like buses on a rainy day? Why did we get two volcano movies in 1997 (Volcano and Dante’s Peak) and two asteroid movies in 1998 (Armageddon and Deep Impact)?
Here’s a hint: in the early 2000s, shortly after The Osbournes had become a surprise hit, I remember reading the reaction of a top executive at a rival network, which was, essentially, “I love it. It’s amazing. It’s completely unique and original and I’ve asked my guys to come up with six ideas just like it.”
Whatever the reason, they arrived at the same time.
I wasn’t particularly interested in any of them at the time (I wasn’t alone, based on a quick poll of my friends), but I decided to watch Super Pumped when I was doing research for my newsletter about Uber earlier this year.
I don’t know if I’d have watched the whole thing if I hadn’t set it for myself as homework. I find it distasteful to watch somebody act appallingly and walk away with a huge windfall. Nevertheless, there was something absorbing about watching the car wreck and I found myself bingeing the other two shows over the subsequent weeks.
WeCrashed suffers from the same problem as Super Pumped.
Travis Kalanick and Adam Neumann are neither heroes nor anti-heroes – Neumann is always described as charming but I would bite my own foot off to get out of being stuck in an elevator with him, while Kalanick is a self-described ‘asshole’.
Unlike Tony Soprano, Walter White, or Jimmy McGill, you don’t find yourself rooting for them to succeed despite their transgressions. You find yourself waiting for them to get a well-deserved comeuppance that never arrives. Sure, both of them lost control of their businesses, but both walked away as billionaires.
The Dropout has the advantage in this regard because there are two clear villains, we can see what they’re doing wrong, we watch various characters try to figure out the scam and then expose them, at which point they each get sentenced to more than a decade in prison. In that respect the show is more like a true crime drama than a story ripped from the business pages, which perhaps accounts for it being the most popular and critically acclaimed of the three.
Watching the three shows side-by-side presented an opportunity to compare them not only as pieces of drama but also as business cases.
If this edition of the newsletter inspires you to take a second look at one or two of these shows, great. If not, you can file it under “I watched these shows so that you don’t have to.”
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