12 min · October 1, 2026
Underpricing Is a Tax You Pay Yourself
Jason argues that the discounts founders give themselves in year one and two quietly bankroll their competitors. Sarah pushes back, digs in, and they trace where all that missing money actually goes.
Jason: I'll say something that's gonna sound insane. The most expensive decision I've ever made across all four companies wasn't a bad hire, it wasn't a failed product. It was charging too little for the first two years.
Sarah: Wait, really? More expensive than a bad hire? I've watched you eat a bad hire that cost like six figures. You're telling me undercharging beat that?…
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