About Commonwealth Legacy Group

We're a firm working with business owners and families on business succession, retirement, life insurance, wealth transfer, and business insurance — in every state where we're licensed.

Cole Whitaker

Cole Whitaker

Founder

I came into this business by a practical route. After the Army I was studying at the University of Kentucky and left because I needed to earn a living. Insurance was the work in front of me, and it suited me better than I expected.

I am the third generation in my family to deploy with the United States Army. I served as infantry in the Army and in the Kentucky National Guard, and hold the Army and Navy Achievement Medals from that deployment. What I took from it was perspective — very little that goes wrong in an office qualifies as a hard day — and the discovery that I could carry more responsibility than I had assumed. I moved into leadership roles earlier than most, and that is where I learned what discipline actually means: people are depending on you to have thought it through before they arrive.

In my second week working on my own, I sat down with a man in Ironton, Ohio. He was carrying several policies with the same company, all priced well above what his situation called for. I consolidated them and returned about seven thousand dollars to him.

He called a month later. He had used it to take his children to a Dallas Cowboys game — their team — and wanted me to know it was the best weekend his family had had in years. I remember that case for the phone call, not the policy work. He is still a client, and a friend.

That conversation shaped how I work. This business is not won on credentials or on chasing commission. It is won on attention to detail — specifically, the details that matter to the person across the table. Do that consistently and the work follows.

I am also the third generation in my family to own a business. The questions this firm exists to answer — who takes it over, what it costs to hand down, whether it survives the transfer — are ones my own family has had to work through.

I built Commonwealth Legacy Group because I believed the standard could be higher. Most agencies rent their infrastructure from someone else, and most compensation structures quietly reward the policy that pays better rather than the one that performs — while doing very little for the agent placing it. I wanted a firm that supports doing the work correctly, and supports the people doing it. Not a recruiting funnel. A place where an independent agent can build something that is genuinely their own.

I grew up in Somerset and came back to build a legacy here. Most evenings you will find me on the back porch with Sera and our two dogs, Remington and Ruger.

How we work

  1. 1. We start with the situation, not the product.

    The first meeting is diagnostic. If there's no gap worth solving, we'll tell you that.

  2. 2. We coordinate with the people already advising you.

    Your CPA and your attorney should be in the room, or at least in the loop. Plans built in isolation fail at implementation.

  3. 3. We stay after the sale.

    Circumstances change — the business grows, children join or don't, tax law moves. A plan reviewed once a year is a plan that still works.

Wherever you're starting from.

A quote takes a few minutes. A planning conversation takes an hour. Either one starts here.