Katya Sarmiento’s time in college certainly gave her a well-rounded education. She embarked on a number of options including air traffic control before realizing a life of travel and entrepreneurship was her true passion. She dropped out of college, quit her part-time job and started her own online business intent on building her future. Through online contacts and Facebook groups she built relationships and helped others. In return they offered her a place to stay when she visited. She soon realized that the sharing world of digital entrepreneurs not only provided her with knowledge and friendship but new places to call home. She now spends most of her time traversing America attending events and hooking up with her digital buddies. Her accommodation is largely free and she gets to experience new locations like a local. We interviewed Katya back home in Miami over the holidays where we discussed her decision to leave traditional education, what life is like as a “digital homeless” and how we need to learn to accept the generosity of others or risk depriving them of the feelings of helping a fellow human.