Today’s episode is about technical debt, not as a cautionary tale, but as a lens. We take a closer look at where debt comes from, how it quietly rewires teams, and why paying it off is rarely just a matter of “cleaning up code.” Along the way, we’ll examine two real-world stories: one where unaddressed debt led to a $440 million disaster, and another where a company used an infrastructure overhaul to rebuild architectural trust. This is about more than code. It’s about momentum, memory, and the systems we inherit.