I think in Rand's case, it means "poor". He has tremendous value built up in his company, but nothing personally to show for it. He's still an unforseen string

I think in Rand's case, it means "poor". He has tremendous value built up in his company, but nothing personally to show for it. He's still an unforseen string of bad luck or hospital stay from being completely broke (or worse). That's why some people mention it's okay for him to take some money off the table if he raises additional funding.