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.
Founder
Cole Whitaker
Chapter I
I’m Cole Whitaker, founder of Commonwealth Legacy Group and a third-generation business owner in Somerset, Kentucky.
My grandfather ran a mechanic and towing business here. My dad spent more than 20 years in law enforcement before starting a business with my mom.
I grew up seeing how much work goes into building something that can give the next generation a stronger start.
Chapter II
That’s why I founded Commonwealth Legacy Group: to help families protect what they’ve worked for and make thoughtful decisions about what comes next.
My work starts with listening.
I want to understand your goals, what matters to your family, and what you need your money to do.
Chapter III
From there, I personally build a financial strategy around those priorities, looking at how retirement income, wealth preservation, and legacy planning fit together.
My goal is for you to leave our conversations with clarity—a practical understanding of your options and the steps toward the future you want.
How we work
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. 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. 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.