Founder
Cole Whitaker
- Licensed insurance producer
- NPN 20771620 (Life)
- Commonwealth Legacy Group · Kentucky DOI #1475734
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.
Areas of practice
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.
- Business succession
- Retirement
- Life insurance
- Wealth transfer
- Business insurance
Insights
- How Much Life Insurance Do You Actually Need?
- Term vs. Whole Life vs. IUL: What’s the Difference and Which One Makes Sense?
- The Five Biggest Risks to a Retirement Plan That Most People Ignore
- How Much Retirement Income Will $1 Million Actually Produce?
- When Does an Indexed Universal Life Policy Actually Make Sense?
- What Happens to Your Business if You Don’t Show Up Tomorrow?
- Your Business May Be Your Biggest Asset. It Shouldn’t Be Your Only Asset.
- The 10-Point Financial Checkup Every Family Should Complete Each Year
- Retirement Planning in Kentucky and the South-Central U.S.: What Families Should Know Before Retiring
- What Happens Financially When Someone Dies? A Checklist for Families
- What Does "Max Funded" Actually Mean?
- What Is a 7702 Plan?
- Infinite Banking: What It Is and What It Isn't
- IUL vs 401(k): Comparing Two Things Built for Different Purposes
- Mortgage Acceleration Strategies, Compared
Wherever you're starting from.
A quote takes a few minutes. A planning conversation takes an hour. Either one starts here.