Stop Fixing Things That Aren't Broken

Whiskey Web and Whatnot · Jun 5, 2025 · 1h 4m

This week, Robbie and Chuck talk about the unintended chaos of “move fast and break things” in both software and startups. From Riverside glitches to Tesla’s overengineered wipers, they explore how updates can derail otherwise stable experiences. They unpack the economics of getting laid off, the pressure to build a personal brand in tech, and the strange fate of dev tools. Plus, Robbie shares his latest app ideas.In this episode:(00:00) - Intro(02:27) - Whiskey rating and review: Old Grand-Dad 16 Year Straight Bourbon Whiskey(13:27) - When updates break what worked(20:21) - Are devs…