Schedule first, secure later

In this episode of High Agency, we sit down with Ian MacKinnon, serial entrepreneur and cybersecurity expert, to unpack the realities of building and protecting products at scale. Ian traces his journey from a scrappy 2014 hackathon project to co-founding Later, which grew into one of the most widely used Instagram marketing platforms in the world, serving over 6 million brands before its acquisition in 2022. He reflects on the early chaos of startup life, including a near-catastrophic database failure that forced him to confront the fragility of fast-moving systems, and how that moment reshaped his thinking around risk, resilience, and responsibility. We explore the tension between speed and security, and why many high-growth companies underestimate the cost of getting it wrong. Ian introduces his current work at Stingray Security, where he’s focused on protecting users from increasingly sophisticated scams and phishing attacks. The conversation expands into the evolving threat landscape, the psychology behind social engineering, and why people remain the most exploited layer in modern systems. This episode also examines the mindset required to move between building and defending technology, the discipline of anticipating failure, and the importance of embedding security into products from the very beginning. At its core, it’s about navigating growth with awareness, understanding where systems break, and building with a deeper sense of accountability in an increasingly risky digital world.