Building a company is messy. Most of it never makes the highlight reel.

Imperfect Company is a podcast from Glitch Capital where Leigh Jasper and Sam Kroonenburg, two founders who’ve built billion-dollar exits before and are going again, sit down with founders to talk about the strategic decisions nobody puts on the pitch deck: the false starts, the bad hires, the pivots that needed to be made, and the unglamorous calls that actually built something real. In this episode,

Leigh and Sam talk through what’s actually different about building in an AI-native world — and what hasn’t changed at all.

They get specific about how AI shifts team shape (engineers running ahead of PM/design), why outcome “harnesses” matter more than prompts, and why taste and coherent UX might be the real bottleneck.

They also zoom out to the investor lens: if software is cheap and fast, what’s defensible now? Data, networks, compliance, and “hard things” (sometimes even hardware) start to look more interesting — and simple feature velocity starts to look less like a moat.

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