Aleshire Insurance Group

“Ale” like beer, “Shire” like county.

A happy family of four sitting outdoors on a stone wall in a park, smiling at the camera, with trees and sunlight in the background.

At Aleshire Insurance Group, we’re licensed and contracted Medicare insurance professionals with a passion for putting others first.

We understand how overwhelming Medicare can be for those who are new to it. So we set out to make the process simple and stress-free. We treat everyone like family, offering a zero-cost consultation with no risk to you. Unlike others, we don’t work for the insurance companies—we work for you.

Our goal is to help you find the right coverage with confidence and peace of mind.

Schedule Consultation

Or Call 1-800-432-9757

Proudly licensed in and serving the following States:

TEXAS

LOUISIANA

OHIO

NORTH
CAROLINA

KENTUCKY

Our Approach

At Aleshire Insurance Group, we follow what we call “The Mom Test."

If we wouldn’t confidently sign up mom for it, we don’t recommend it to our clients.

This test makes our job easy. We guide every decision with the same care and attention we would give to our own mothers. We approach each client interaction as if we were helping a loved one, ensuring that the advice we offer is grounded in trust, empathy, and integrity. Our goal is not just to sell insurance but to provide genuine peace of mind, helping clients navigate their options with clarity and confidence.

We recognize that many clients, especially seniors, face complex and overwhelming insurance choices. Knowing how easily someone in that position could be misled, we make it our mission to act with honesty and responsibility at every step. For us, it’s never about sales goals or profit margins—it’s about building lasting relationships rooted in trust. Every recommendation we make reflects what we believe is truly best for our clients, just as we would want for our own family members.

A woman with brown hair smiling at a social gathering, wearing a purple dress, with a note pointing to her saying 'That's Mom!' and another note saying 'Mom deserves the best!'
Two women, one middle-aged and the other young, hugging and smiling at the camera. The older woman wears glasses and a blue shirt with text that reads "Mother of the Bride." The younger woman wears a white shirt with text that reads "Bride." Handwritten annotations say "AU'S MUM!" with an arrow pointing to the older woman and "Every client, like family." at the bottom of the image.
Get Treated Like Family

Aleshire Insurance Group

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144 Years of Helping Others

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Aleshire Insurance Group — 144 Years of Helping Others —

Helping Others

A Family Tradition

Paul Aleshire - Back row, fourth from left in White button-down shirt.

For generations, our family has been dedicated to serving communities through the insurance business, a tradition that spans over a century. Starting with Douglas Aleshire, who survived the Gasconade Bridge Disaster and built an insurance agency with his seven sons, our family's commitment to helping others has been passed down through the generations. Charles Aleshire, Douglas' son and my great-great-grandfather, carried this legacy forward, as did my great-grandfather Damon and my grandfather Paul Damon Aleshire.

Black and white photo of two men sitting at a table, shaking hands. The man on the left is smiling and wearing a light-colored jacket with a tie. The man on the right is older, with a serious expression, and is also dressed in a light-colored suit with a patterned tie. The table has a checkered tablecloth, and a newspaper labeled "KOBO" is visible on the table. The background shows floral wallpaper and a small vase with flowers. 
Paul Aleshire (My Grandfather, Left) and Damon (My Great-Grandfather, Right) likely speaking about Insurance, April 1953.

A lasting legacy

Today, we continue to honor this family tradition by specializing in Medicare insurance, focusing on providing guidance and peace of mind to those turning 65 and beyond.

Our family's rich history and dedication to service have shaped who we are today, and we remain committed to supporting you in your insurance needs with the same integrity and care that has defined our family for decades.

Black and white photo of a man sitting at a cluttered desk in an office. The man is smiling and wearing glasses, a suit, and a tie. The desk has papers, books, and office supplies, with a computer mouse and a set of headphones on top. The background features patterned wallpaper and framed pictures on the wall. 
Damon Aleshire, at his desk, Circa 1950.
A black-and-white historic photograph of ten people, five men seated in the front row and five standing behind them in a studio setting. 
Douglas Damon Aleshire - Front row, holding cane. Charles Aleshire (Father of Damon), far right bottom row.
A portrait of an older man with a long white beard and light-colored hair, wearing a dark suit, against a warm background. 
Charcoal Drawing of Douglas D. Aleshire Circa early 1900's.

Medicare Resources