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Talking Defective Visionaries And The Tebow Renaissance, With Reeves Wiedeman

WeWork CEO Adam Neumann, seen here contemplating our podcast logo and doing a bunch of crime.
Photo by Cindy Ord/Getty Images for WeWork

There is more than enough money out there in the world, which is heartening until you think about who has most of it, how they got it, what they tend to do with it, and the damage that all of the above can do to the vast swath of humanity that lives somewhere downhill. It is a very steep hill, and the houses on top of it are very large, and their drainage systems are very poorly installed, and the quality of the tap water down below has suffered notably, but what are you going to do? All the most satisfying and proactive answers to that question are banned under Twitter’s terms of service, and most of the other ones are honestly not great.

But there’s no harm in learning about and laughing at the delusions and tics and soaring gilded grifts that define the ambitions and doings of the very rich. Reeves Wiedeman’s book Billion Dollar Loser, which tells the story of the whole sprawling WeWork hustle and the grandiose founder who built, looted, and crashed that company, is a great primer on that front, and so we had him on to talk about it.

We did not just talk about that, although we could surely have filled this and a few other episodes with nothing but a catalogue of the things that founders Adam Neumann and Miguel McKelvey tried to and mostly succeeded in getting away with. We talked about how companies and hustles like this come to exist, how and why they tend to bust the way they do, and the perils of getting high on your own supply. In what is honestly not as big a leap as you might think, we talked about the things we will do to justify drinking beer outside and the last humiliating moment of Tim Tebow’s NFL relevance, which Reeves and I watched together from the press box in Foxboro, Mass.

Once Reeves left to do vital journalistic work, Drew and I cut loose and leaned into the usual idiocy. We talked about good NFL teams and bad ones, a bad baseball organization making a good executive hire, and the liminal state of Preparing To Fail that the Houston Rockets have righteously staked out for themselves. The righteous indignation of the show’s first half carried over somewhat into the second, at least in the sense that I remain indignant that Drew still sings the damn mash-ups and we agreed that Motley Crue’s “Kickstart My Heart” still sounds pretty fucking righteous. The rich people and their foolishness will hurt us again and again, but this is no reason not to embrace whatever foolishness amuses us in the moment. What are you going to do, if not that?

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