Every company hits a moment where the thing that worked at ten customers breaks at a hundred. What Breaks First sits down with founders, operators, and industry voices who have lived through that fracture: the hire that came a year too late, the process nobody thought to build until it was too late not to, the handoff from founder instinct to operator discipline. Hosted by Ian, joined by Matt & Ben, each episode trades the highlight reel for the honest account. No case study gloss. Just what actually broke, what it cost, and what replaced it. For founders, operators, and anyone building past the point where duct tape stops working.