In times of uncertainty, new ideas, concepts and business solutions are born. The crisis caused by the Coronavirus disease 2019 (COVID-19) pandemic has had a wide impact on the tourism sector, from small-scale to multinational companies. Based on an explanatory case study of a tourist guides venture, the paper seeks evidence on how conditions such as social capital, the use of information technologies and the application of new organizational solutions can support entrepreneurship at times of crisis. The paper provides insight into the functioning of Guides without Borders—a venture bringing together over 50 tourist guides. The research is based on the case study methodology supported by semi-structured interviews and questionnaires. Findings indicate that despite harsh times, social ties, trust and technology can leverage an organization. The research also confirms that the application of an innovative approach to the organizational structure and processes (in accordance with the concept of teal organizations) is beneficial at times of crisis. Thus, the organizational approach adapted by the studied organization can serve as an example for future tourist guides and other professionals’ undertakings in uncertain times.