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. Featuring Ian MacKinnon Co-founder Later.com Ian MacKinnon is a serial entrepreneur and cybersecurity expert currently serving as Founder of Stingray Security, where he focuses on protecting users from online scams and phishing threats. He previously co-founded Later.com, transforming a 2014 hackathon project into the leading Instagram marketing platform serving over 6 million brands before its acquisition in 2022. A CISSP-certified professional, Ian holds a Bachelor's and Master's in Computer Science from the University of Waterloo and a Master's in Management Science & Engineering from Stanford. He actively mentors startups and continues to teach coding at bootcamps. Hosted by Mo Dhaliwal CEO Skyrocket Digital Software engineer turned marketer, Mo is an entrepreneur, cultural curator and technologist. In his role as founder and CEO of Skyrocket Digital, he helps clients with business, brand and technology to launch new ideas and grow their businesses. — High Agency: Conversations that Drive Growth and Transformation Instagram: https://www.instagram.com/highagencypod/ LinkedIn: https://www.linkedin.com/showcase/high-agency-pod X: https://x.com/highagencypod TikTok: https://www.tiktok.com/@highagencypod — Presented by Skyrocket Digital Skyrocket is the digital agency for ambitious leaders. Our capabilities empower business and marketing leaders with the confidence to launch new initiatives, grow their brands, and undergo the transformation necessary to achieve breakthrough results.