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In this episode of That Tech Pod, Kevin and Laura sit down with IT entrepreneur Rob Calvert, founder of Second Son Consulting and a longtime leader in the Apple enterprise ecosystem. After being laid off in the early 2000s, Rob built his consulting firm from a home office into the largest member of the Apple Consultants Network in Los Angeles and one of the top firms in the country. Drawing on more than 25 years advising companies across dozens of industries, he shares a grounded look at what actually makes technology succeed or fail inside real organizations. The conversation even opens with an unexpected detour into “Punch the monkey,” a viral zoo story that sparks a debate about how easily people question or misread what they see online in the age of AI (Laura swears this is a real monkey while Kevin thinks its GenAI to sell toys).
From there, the conversation explores why most people only notice IT when something breaks and how that mindset leads to bad leadership decisions. Rob argues many “tech problems” are really culture and workflow problems, pointing to common mistakes like letting experimental tools quietly become production systems or constantly chasing new platforms without fully implementing the ones already in place. The result is wasted budgets, burned-out IT teams, and systems that drift away from how people actually work. They also get into the Mac vs. PC debate in the enterprise, the subtle ways companies waste millions in IT spending, and the gap between AI hype and real business impact. Rob says many small and mid-sized companies are spending a lot of time evaluating AI tools but seeing very little return so far, while larger organizations may eventually benefit through heavy customization. At the end of the episode, Rob finally agrees to go look up Punch the monkey. 🐒
Rob Calvert is an entrepreneur and IT leader who has spent more than 25 years helping businesses make technology actually work for the people using it. After being laid off in the early 2000s, Rob Calvert built Second Son Consulting from his home office into the largest member of the Apple Consultants Network in Los Angeles and a top-ten firm nationwide. His work focuses on aligning technology with workflows and culture rather than treating IT as a standalone function, and his team has created widely used open-source tools for the Mac admin community. Rob has advised companies across more than 15 industries, managed millions in IT budgets, and is known for challenging cookie-cutter approaches to IT in favor of systems that support how people actually work.
