Peter, Paul, and Martin, three Aussie innovators, launched an exciting e-marketplace in 2006, Redbubble. By 2018, the online platform was serving over 400,000 independent artists, bringing their artwork to clients through what had become a business-to-consumer platform. In 2015, Redbubble extended their activities decisively into the European Union in the hope this would provide greater learning and adaptation and further and deeper engagement with the communities they were keen on: independent artists and online-savvy customers with economic and cultural values similar to those in Australia. In early 2018, the Redbubble board and leadership team decided to review the global art and design marketplace’s international strategy and its impact. In particular, the team now pondered whether the increasingly challenging regulatory regime of the European Union would prove to become a competitive advantage or disadvantage in the global marketplace and influence expansion. The General Data Protection Regulation, enforced on 25 May 2018, proved to be a timely issue to consider when planning ahead. The team wondered how a highly sophisticated level of regulatory compliance and the cost advantages of doing business in a Single Market would influence Redbubble’s international future.