Our Story
A legacy of service, four generations strong
Our Story
Caldwell Insurance Services is part of a proud, four-generation family tradition. It all began with Sherman Robert Caldwell, whose honest, neighbor-first approach inspired Robert Caldwell to follow in his footsteps.
That legacy carried forward through Kent Sherman Caldwell, who served Southern California families and businesses for over 30 years with the same belief: insurance should always put people first.
Today, that promise continues with Tyler Caldwell, the fourth generation of Caldwells dedicated to protecting what matters most with honesty, care, and a personal commitment to every client.
Why Choose Us?
✔️ Independent: We work for you, not one carrier.
✔️ No Added Cost: Our help costs you nothing extra — just honest guidance.
✔️ Family First: Four generations of putting clients ahead of profit.
A Trusted, Family-Owned Business
Kent Caldwell, the third generation of Caldwells to serve our community, built this business on one simple promise: help first, self second.
For over 30 years, Kent went above and beyond for every client who walked through his door — searching tirelessly for the best possible rates, better plans, and honest answers at every turn.
He believed that trust is earned through hard work and genuine care — not sales talk. That’s why generations of families and small businesses came to rely on him for guidance they could count on.
To Kent, no question was too small, no client was ever just a number. His legacy lives on through every conversation, every policy, and every new family we serve today.
Carrying the Caldwell Legacy
As the proud fourth generation of Caldwell Insurance, I, Tyler Caldwell, carry forward my father’s mission — and the Caldwell promise that started with Sherman Robert Caldwell generations ago.
Growing up, I watched my father Kent work day and night to protect his clients — treating them like family, fighting for better coverage, and doing whatever it took to put people first.
Today, I’m proud to continue that same promise: to guide you with honesty, fight for the best possible solutions, and stand by your side through every life stage — just like my family has done for over 70 years.
From Medicare guidance to individual health plans to small business benefits, my goal is simple: to protect your peace of mind with the same care and dedication that only a Caldwell can deliver.
Our Clients Say It Best
Don’t just take our word for it — here’s what families and small businesses across Southern California say about working with Caldwell Insurance.