This episode explores the advantages and challenges of self-hosting versus cloud-based services for individuals and businesses. Against the backdrop of a long road trip to interview Wendell Wilson, a technology expert, the hosts delve into Wendell's personal approach to balancing on-premise infrastructure with cloud solutions. More significantly, the conversation highlights the increasing accessibility of self-hosting, enabled by technologies like containerization, even on resource-constrained devices like Raspberry Pis. For instance, Wendell discusses his use of containers for backups and his strategy of employing a hybrid approach, leveraging both local servers and cloud services for redundancy and security. As the discussion pivots to home automation and media management, Wendell details his sophisticated home setup, including a custom-built IoT system and a Plex server, showcasing the power of personal technology integration. In contrast to the convenience of cloud services, Wendell emphasizes the importance of offline backups and the reduced attack surface of self-hosting, particularly in the face of increasing cloud outages and ransomware attacks. Ultimately, this episode underscores the evolving landscape of technology infrastructure, where individuals and businesses are increasingly empowered to customize their solutions, balancing convenience with control and security.