From Microsoft to Startups: Building a Career That Moves

In this episode of Career Flair: Are You Business Ready?, host Ryan Foland sits down with Miguel Caballero, a software engineering manager at the AI startup Harmonic, to explore what it really means to build a career across big tech and entrepreneurship. Miguel shares his journey from competing in the Microsoft Imagine Cup to landing an internship that moved him from Spain to Ireland and eventually the United States. He reflects on working on products like Office, Visual Studio, and Skype and why he ultimately felt pulled back toward the startup world. The conversation moves beyond titles and into mindset. Miguel opens up about building his own travel app, the mistakes he made by skipping validation, and how the lean startup approach reshaped how he thinks about risk, ownership, and execution. They also unpack what startup hiring actually looks like today. Miguel explains why culture alignment, attitude, and ownership often matter more than raw technical skill — and how candidates can use storytelling, vulnerability, and clarity to stand out in interviews. Whether you're aiming for big tech, curious about startups, or figuring out how to grow without getting stuck in one lane, this episode offers a grounded look at what it takes to build something meaningful — including your own career.