When I first tried to raise money — in 1998 for a company called 360merch — a handful of plucky angel investors agreed to trust me with one million of their dollars. I wore my fingers to the bone in that business, hawking lenticular stickers and logo’d baby doll t-shirts using affinity marketing models — and then promptly lost them all of their money when the market crashed.
Image: Dave Balter, founder of Mylestoned - http://www.businessinsider.com