In this episode of the Online Reputation Management Podcast, host Jason Mills sits down with digital landlord and entrepreneur James Dooley to unpack the mindset, systems and ethics behind building one of the UK’s largest portfolios of digital real estate. The conversation follows James’ journey from quantity surveyor in offline construction to owning hundreds of rank-and-rent sites, showing how resilience, testing and strategic failure shaped his growth. They explore why James prioritises freedom, happiness and relationships over vanity revenue targets, and how his vision of “doing things I love, with people I love, in a way I’m proud of” guides every partnership decision. Jason and James dig into delegation, culture and leadership, including why James now sees himself as a “cultural architect” who builds empowered middle management instead of micromanaging staff. They discuss the power of networking, giving value first, and surrounding yourself with partners who complement your weaknesses rather than mirror your strengths. Throughout, James stresses that true success is about integrity and long-term trust—especially when clients become dependent on his leads—and warns against chasing a fixed “end goal” that often leads to emptiness. The episode frames online entrepreneurship as both opportunity and responsibility, offering practical insight for anyone wanting to scale without losing their values.
