8 min · July 13, 2026
When to Hire Your First Employee (or Don't)
Jason argues most founders hire too early to feel less lonely. His co-host isn't buying it. A real fight about when a second set of hands actually pays off.
Co-Host: Okay, so I want to start with something you told me off-mic last week that kind of annoyed me.
Jason: Great, love that energy.
Co-Host: You said most founders hire their first employee about eight months too early. And you said it like it was obvious.
Jason: Because it is obvious to me. Not because I'm smart — because I've done it wrong. Twice.
Co-Host: Okay, so define "too early." Too early relative to what?…
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