13 min · November 5, 2026
Your First Hire Should Probably Be a Mistake
Jason argues most founders hire too early for the wrong reasons — and Sarah pokes at where that logic breaks down. A long, wandering talk about staying solo, the real cost of a headcount, and the one hire that actually saved him.
Jason: Okay, hot take to start: I think your first employee should almost always be a mistake. Like, you should hire slightly too late and slightly wrong, and that's the correct outcome.
Sarah: Wait, really? You're telling founders to aim for a bad hire? That's a weird thing to put on a podcast, Jason.…
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