Hi Scott !
The saying " you need money to make money " is completely true, what confuses or dissappoint people is the mistaking or wrong perception of that saying . The saying is always meant to target people who are the second level of the business already now want to move to the next level or higher levels but strictly not to underground level or first levels.
At underground level or initial level to do business more concern is better preparation such enough knowlege of the business you plan to do,skills , good communications , partners or even get employed to accumulate some money for couple of months. And you can either sell your talents, skills or experience to get money before using your own money. This is what I call preparation. Simply to make preparation for starting a business not necessarily to have money but moving to the higher level of the business money is mostly required .

Thanks .