Open source geospatial technologies have been witnessing exponential growth in their maturity and adoption in the past number of years, in particular within the domain of delivering mapping content through web technologies. DM Solutions Group (DMSG) has been one of the primary developers of these technologies during the past 10 years. One of the challenges of developing open source technologies is identifying how open source can be an effective strategy within a software company's overall business plan. MapSherpa.com is the culmination of DMSG's experience discovering this balance to achieve a successful commercial offering. This presentation will focus on some of the technologies that have become critical to MapSherpa.com's success and the lessons learned in terms of applying an open source strategy to a successful business endeavour.