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Podcast 29 min

How to be a legally compliant digital nomad with Sam Matthew

When it comes to digital nomadism, Sam Matthew has walked the walk. Today, he heads the legal team at OnDeck, a platform for entrepreneurs with a fully distributed workforce. Before that, he was general counsel for Remote Year, a company that facilitates travel for those working remotely. In this role, Sam witnessed many of the challenges of facilitating the employment of digital nomads firsthand: he himself worked across 20+ countries in a three year period, linking up with other Remote Year employees in Latin America, Europe, and Asia along the way. Here he shares with Job some of the key lessons he took from his travels, including the different approaches one can take toward tourist visas and work permits. He explains how countries across the world will have very different approaches to digital nomads, from some that are creating laws to encourage nomadism to others that legally oppose the practice. The conversation also turns to the legal difficulties companies can run into when hiring abroad, from complying with health and safety regulations to discovering the difficulties of terminating a contract.