Can you tell I liked me some Charles Dickens?
In professions
[1] A supervisor or superintendent; one who keeps watch over and directs the work of others, often in the context of forced labor or slavery
[2] In law, a person appointed by the testator to supervise or assist the executor(s) of a will (mostly obsolete)
[3] Overseer of the Poor, an official who administered poor relief
It's muddled at best, but the usage in reference to a supervisory role in a professional context [1] is distinct from what you allude to [3], and [1] has the qualifier "often in the context of forced labor or slavery".
My cautious rebuttal...
Startups are generally poor when they arrive at YC. Maybe that's just Sam injecting a little sly humor like he did with that last line?