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Santiago Jaramillo on entrepreneurship, inner work, and AI transformation

Oct 23, 2025 6:30:00 AM

The Edge Podcast Santi Jaramillo HS FT image quote 2

On this episode of The Edge, host Tim Leman sits down with entrepreneur and former CEO turned executive coach, Santiago “Santi” Jaramillo. Santi shares the arc of his journey—from growing up in Cali, Colombia, to building Emplify, to coaching leaders—and how those experiences shaped his approach to leadership, culture, and now AI adoption. They explore the importance of inner work after achieving external success, and Santi opens up about learning to separate self-worth from productivity, as well as the power of leading from love rather than fear. They also dig into why AI is first a cultural transformation, not just a technical one.

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Topics: Executive
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Gibson is a team of risk management and employee benefits professionals with a passion for helping leaders look beyond what others see and get to the proactive side of insurance. As an employee-owned company, Gibson is driven by close relationships with their clients, employees, and the communities they serve. The first Gibson office opened in 1933 in Northern Indiana, and as the company’s reach grew, so did their team. Today, Gibson serves clients across the country from offices in Arizona, Illinois, Indiana, Michigan, and Utah.