Founders' Tales - Building AI That Prevents Website Outages Before They Happen

In this episode of Founders’ Tales, we sit down with Aaron "Checo" Pacheco, founder and CEO of OtterMon AI, to explore how his team is rethinking website monitoring and reliability in an increasingly complex tech landscape.

With more than fifteen years of experience in the Boston tech ecosystem, Checo shares how repeated exposure to alert fatigue, monitoring noise, and preventable outages led him and his co founders to build OtterMon AI. Their mission is simple but ambitious. Make monitoring proactive instead of reactive, and turn it into a true partner for developers rather than another tool they have to manage.

Checo walks through the evolution of OtterMon’s MVP, from an early chatbot concept to a platform that continuously analyzes signals to surface risks, highlight optimization opportunities, and help teams prevent incidents weeks or even months before they occur. He also explains how close collaboration with design partners shaped the product and helped refine what real customers actually needed.

The conversation goes beyond product development and dives into the realities of startup life. Checo shares lessons learned from customer validation, fundraising, hiring for true startup DNA, and building momentum through trust, social proof, and strong relationships. He also reflects on the Boston startup ecosystem, highlighting the importance of community, local resources, and founder support.

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