An exploratory study analyzed Meetup groups in Boston, Silicon Valley, and New York City to understand differences in their technology and business community ecosystems. Machine learning was used to categorize groups, which found that Boston had more programming language groups while New York had stronger business networking groups. Social network analysis identified central groups in each city. Comparisons across cities found similar but not identical group types. Member interests were also analyzed to identify recommendations for new groups. The goal was to develop a system to recommend new or related groups to improve regional community landscapes.