This document outlines a roadmap for a smart connectivity and interaction marketplace system that connects coworking centers, corporates, and events through an AI serendipity software. The system allows for online reservations, yield management, CRM capabilities, reviews, and integration with a Serendipity Machine. It has approximately 175 locations across 28 countries. The document discusses how a chaordic society is on the rise through internet, social web, and collaborative economy trends that will lead to an autonomous world characterized by volatility, uncertainty, complexity, and ambiguity. It proposes connecting coworking, coliving, coproducing, and coimpacting through community integration and by leveraging social capital, monetary capital, and shared open collaboration spaces