After more than two decades since the interdisciplinary field of ontology emerged for information science, it is now poised to make a huge impact. The ontological approach aims at making intended meaning explicit and computable. By enabling better human-machine "understanding" across complex socio-technical chains, ontologies are facilitating the vision of co-evolution of humans and their tools. Applying ontology requires a very broad spectrum of disciplines and skills, and is therefore best tackled not by individuals, but by communities of people working collaboratively. This position paper attempts to trace the brief history of ontology communities from the author's vantage point, identifying some of the key dates and key players (mostly familiar names, but some unsung heroes as well) that have made things happen for the field of applied ontology. Inspired by Doug Engelbart's "bootstrap" strategy, the author has developed and operated (until his recent retirement) a virtual collaborative environment (CIM3.net), on which some ontology communities (such as Ontolog and Ontology Summit) have thrived. Observing that the funding and career opportunities have changed for the better in the past few years, the author reflects on how the ontology communities of practice might leverage what they have built so far, and take applied ontology into an even better future.