What challenges did Brian Chesky face when pitching Airbnb to angel investors?

Brian Chesky encountered significant rejection when seeking angel investment for Airbnb. Out of approximately 15 angel investors he approached, nearly half didn't even reply to his emails. Among those who responded, many rejected the concept, claiming it didn't fit their investment thesis despite being consumer internet companies, or stating the market wasn't big enough. One investor simply wasn't excited about the travel category. The challenges culminated in a particularly awkward meeting with angel investor Mike Maples, where Chesky arrived without a presentation deck, planning to showcase their newly launched website. Unfortunately, the website didn't work during the meeting, leaving Chesky struggling to explain the concept for an hour while the investor had difficulty understanding the vision.