Rick Teska
Founder & CEO
Rick is the Founder & CEO of Strive Medicare, and at his core, he’s a relationship-first leader who believes Medicare decisions should be clear – not confusing.
After seeing how overwhelming Medicare can be for families, Rick founded Strive Medicare with one simple mission: to ensure no one feels alone or pressured when making healthcare decisions. He understands that turning 65 or changing coverage isn’t just paperwork – it’s personal. It affects your health, your finances, and your peace of mind.
That’s why Rick and his team take the time to truly listen. They sit down face-to-face with clients across La Crosse and the Midwest, explain options in plain language, and help each person choose coverage that fits their unique needs and budget. Because Strive Medicare represents multiple top carriers, the guidance is always centered on what’s best for the client – not a single company.
Rick believes trust is earned through honesty, consistency, and showing up for people when they need you most. Under his leadership, Strive Medicare has become known as a dependable local resource – a place where questions are welcomed, and decisions are made with confidence.
When he’s not serving clients, Rick treasures time with his family and especially his grandkids. Whether it’s attending events, sharing stories, or simply enjoying everyday moments together, family is at the center of his life. He also enjoys spending time outdoors hunting and fishing – activities that reflect the patience, preparation, and respect for tradition he brings to both his business and his relationships.
For Rick, this work is more than insurance – it’s about serving people well and building something his family can be proud of.
Rick Teska
Founder & CEO
Rick is the Founder & CEO of Strive Medicare, and at his core, he’s a relationship-first leader who believes Medicare decisions should be clear – not confusing.
After seeing how overwhelming Medicare can be for families, Rick founded Strive Medicare with one simple mission: to ensure no one feels alone or pressured when making healthcare decisions. He understands that turning 65 or changing coverage isn’t just paperwork – it’s personal. It affects your health, your finances, and your peace of mind.
That’s why Rick and his team take the time to truly listen. They sit down face-to-face with clients across La Crosse and the Midwest, explain options in plain language, and help each person choose coverage that fits their unique needs and budget. Because Strive Medicare represents multiple top carriers, the guidance is always centered on what’s best for the client – not a single company.
Rick believes trust is earned through honesty, consistency, and showing up for people when they need you most. Under his leadership, Strive Medicare has become known as a dependable local resource – a place where questions are welcomed, and decisions are made with confidence.
When he’s not serving clients, Rick treasures time with his family and especially his grandkids. Whether it’s attending events, sharing stories, or simply enjoying everyday moments together, family is at the center of his life. He also enjoys spending time outdoors hunting and fishing – activities that reflect the patience, preparation, and respect for tradition he brings to both his business and his relationships.
For Rick, this work is more than insurance – it’s about serving people well and building something his family can be proud of.