In April 2014, Josh and I started Underdog.io as a side project to help pay the bills and buy some time to finish another product that we had been building. The premise behind Underdog.io was simple. If the hiring/recruiting spectrum is bookended by job boards on one side and agency recruiters on the other, we saw an opportunity to build something in between the two that struck a balance between the effectiveness of a good recruiter and the simplicity and inexpensiveness of a job board. Sixteen months later, we’re a team of five that’s closing in on $1 million in annual recurring revenue. Aside from a $20,000 “loan” from a friend, we haven’t raised any money. We thought it would be helpful to share how we’ve made it work so far and some of the things that we’ve struggled with.