Spending money on your own account is a difficult psychological hurdle. Lots of small businesses get stuck in this chasm, happy to pitch, to network, to send out proposals and to work far into the night, but hesitate when it comes time to pay actual cash money for marketing, trade show booths or other sorts of media.
For the bootstrapper, for the woman who has worked so hard to get to positive cash flow, it feels dangerously daring, on the verge of insanity.
The question is: do successful businesses spend money on media, or does spending money on media make you successful?
(I think it's some of both.)