AirBNB was rejected by seven investors who could have had 10% of the company for $150,000 in 2008.
Fred Wilson of Union Square Ventures wrote on his AVC blog an honest account of passing on an opportunity to invest in AirBNB early.
He wrote in his article of 16 Mar 2011, "We made the classic mistake that all investors make. We focused too much on what they were doing at the time and not enough on what they could do, would do, and did do."
He was forewarned by Paul Graham of Y Combinator who wrote in an email to Fred that "Once something becomes a big marketplace, you ignore it at your peril".