Meet Ryan

Ryan Chupo is a dedicated real estate professional serving San Mateo and surrounding Bay Area communities. With over five years of experience in sales and client success, Ryan brings a calm, patient, and consistent approach to every client interaction—earning trust through his follow-through and genuine care.

Originally drawn to San Mateo for its great weather, family-friendly neighborhoods, and strong schools, Ryan made the move with his daughter in mind—and that mindset of building a solid future carries into his real estate career. He doesn’t come from a flashy or traditional real estate background. Instead, his foundation is real-life experience, discipline, and the belief that success comes from showing up—even when it’s hard.

Ryan was inspired to enter real estate after seeing close friends and family experience the life-changing moment of homeownership. That impact stuck with him, and now he’s focused on helping others—especially first-time buyers—feel confident and supported throughout the process.

Outside of real estate, Ryan is a proud father, future husband, and active volunteer at his daughter’s Catholic school. He’s also currently training in calisthenics, enjoys gaming, EDM, and believes in steady growth—personally and professionally.