The Weekender, August 22, 2026: The Crazy Exes

First of all, in case you missed them, this past week we had Episodes 5 and 6 of Season 3 go live, and if there was a theme to those two episodes it was misconnections.

Here was Episode 5. Here was Episode 6.

This next week, we've got the coming-to-a-head of a theme that has been swirling around. Which is the Keegan-Laura-Cara dynamic that we've been developing since the middle of Season 2.

The thing to understand about Keegan, Oscar's buddy and IT genius, is he's a guy with an underappreciation problem.

Keegan is a computer nerd. It turns out that he's a budding tech bro, but he hasn't followed a typical tech bro path. Keegan got a job working for a health insurance company and rose to the head of its IT department, but before Oscar found him he'd gotten himself fired after sounding the alarm over the company's neglect of its network security.

And then he was proven right.

Keegan then launched a business making apps, which languished. He got together with Oscar, and Oscar put him to work on IT projects as a subcontractor to Oscar's consulting business. That got Keegan the day-job money he needed to pursue the app business, and eventually Keegan hooked up with a tech investor in town interested in marketing the apps he made.

So professionally, things worked out pretty well.

Except... Laura.