We have a long-time investor that went through a peculiar phase of refusing to pay for coffee. He still wanted his daily espresso, he just decided he wouldn’t pay for it. Not that he carried some sense of entitlement or was protesting the cost, his motivation was something altogether different.
It made for awkward theater, but that was his point.
Part of his interest in real estate is as a method to shake the world by the lapels, so with any of our projects he’ll ask questions like: “have you considered painting the building neon pink?” or “what about adding an oversized peace sign, you know, just to stir it up a bit?".
During the free coffee phase - one he'd only spring at busy places - the charade went like this: when he got to the front of the line he’d request some over-involved double-this half-that coffee preparation and then, with a compassionate nod, inform the cashier he wouldn't be paying.
An uncomfortable smile would form on the cashiers’ face as they wondered what was up with the jackass.
Soon afterwards, as the line stalled and the consumer zombies sensed disruption to the shuffle cadence, heads would bob up from phones. They’d see him standing there, beaming with confidence, and to the manager who had stepped in by then, repeat “thank you, but I won’t be paying”.
In that pause - when discomfort peaked - a slow smile would cross the cashier’s face as they realized it wasn’t their problem and they could instead be an accessory to the emerging civil disobedience. They’d often take a step back and nod, watching the bizarre scene unfold as this weirdo - who by any other metric would appear to be “the man” - was himself sticking it to the man.
Sometimes the manager would crack first "fine. sir there’s no charge".
Sometimes another customer would pay out of passive aggressive annoyance "hey, guy, um, it’s fine just let me pay for that or whatever".
Sometimes another customer would pay out of exasperation "c’mon dude".
But the resolution, whatever it was, only came after deep discomfort - the cringey kind that woke people up.
The scene would end with him stuffing some jaw-dropping cash tip into the jar and paying for everyone else’s coffee after giving a short speech about how we should all wake up and suck the marrow from the bones of life.
Who knows if the coffee shenanigans changed anyone’s life, other than costing them some time in their morning routine wondering who this strange man was, but I’ve got to believe someone got pushed just enough to see they weren’t living in the moment. And maybe it registered with a few folks that maybe we shouldn’t take life for granted and that the only life we have is in the here and now. And what a gift that would be, despite how annoying the delivery.
He's an odd and wonderful friend - a genius businessman that also knows how to live. It’s a rare combination, and something we can all aspire to, at least the living part.
And we can even do it while still paying for our coffee.
Great story. Some are born without a fear of awkwardness, and some learn to suppress their discomfort. But either way, it’s a powerful trait.