Airbnb absolutely should have died long before it got close to Y-Combinator. Why they didn’t is a story of $40,000 in maxed out credit cards, dozens of rejections, a lost cell signal that almost tanked the company, burned fingers, a high fiber diet of “Cap’n McCains”, and everyone thinking they were nuts. One things for sure—No matter how screwed your startup may seem... The early days of Airbnb was even worse.

Andy Dunn has spent the past ten years building Bonobos. He’s funded about 15 other ecommerce companies, advises even more, and serves on the board of three others. In this interview, he shares his thoughts on better fitting pants, 100M in capital, and why men should embrace a world run by women.