“Bootstrapping vs Raising Capital” are the binary terms that many people view the continuum of fundraising options. In my many years of experience, this is a gross misunderstanding of what lies ahead for new founders. Money doesn’t usually fall from the pockets of the well informed investor like rain in a storm. A more likely title should be “you are going to be bootstrapping because most people won’t give you a lot of money for a long time.”. Not quite as appealing of a title?