Many of the leaders in the Ruby community are business founders. As a basis for this talk, I will interview a number of founders who are also key influencers in the Ruby world. How has working with Ruby helped shape the products they build? How have needs and constraints of the business impacted on their software and the code they've written? What are the benefits of being a hacker and an entrepreneur? What are the downsides? Through consideration and curation of these interviews, I will present an insightful look into the relationship and interdependence between business and code. This talk will appeal to anyone who is bootstrapping their own startup using Ruby, or who is interested in doing so.