This checklist helps successful families uncover blind spots
before they turn into costly regrets.
You want to do more than retire. You want to finish well, with clarity, purpose, and a plan that honors everything you've built. If that's you, you're in the right place.
We help:
Legacy-Focused Business Owners nearing retirement, looking to protect your company and unify your family.
Corporate Executives approaching the next chapter in life, seeking clarity, income confidence, and tax efficiency.
Medical Professionals with complex financial lives, needing protection, simplicity, and long-term strategy.
Faith-Based Stewards who see money as a tool to bless family and community with eternal impact.
Early in his career, our founder Gary Woolman met a promising young doctor and his wife. They were living the dream” a new home, a growing family, and a future full of potential. But they had no protection in place. Despite warnings, they declined life insurance.
Two years later, the doctor died suddenly.
The emotional grief was compounded by financial ruin: repossession, foreclosure, and a complete collapse of what they had built. Gary tried to help. But he was working at a financial institution that valued numbers over people. The moment broke something in him—and built something, too.
It built a calling: to protect families from preventable pain. To help them build wealth that lasts. To create plans with foundations, not just walls.
That mission still drives us today.
At Woolman Financial Group, we don’t just grow wealth. We shape it into a tool for lasting good. Our services are designed to protect what you’ve earned, provide clarity about the future, and multiply your impact across generations.
Cash Flow Optimization
Replace uncertainty with a clear, automated plan for spending, saving, giving, and investing.
Protection Planning
Safeguard your income, business, and family from life's most significant risks.
Retirement Income Design
Turn assets into strategies for predictable income throughout retirement.
Business Exit Planning
Exit with confidence, honor your life’s work, and minimize taxes.
Legacy & Estate Planning
Pass on more than money. Pass on values, wisdom, and harmony.
Tax Diversification Strategies
Keep more of what you’ve earned by managing lifetime tax exposure.
You don’t need a pile of products. You need a trusted guide. That’s why we developed a process that brings order, clarity, and purpose to your financial life.
Quality Control Check
We begin with a 20-minute conversation to explore your goals, fears, and fit.
Discovery
We dive deep to understand not just your finances, but your values, family dynamics, and vision.
Clarity Session
We share findings, reveal blind spots, and offer direction rooted in what matters most to you
Custom Design
You receive a plan crafted specifically to align your wealth with your purpose.
Implementation
We work alongside your CPA, attorney, and other professionals to put the plan into action.
Lifelong Partnership
We review and refine as your life evolves. Your plan stays aligned. Your legacy stays intact.
Here's how real clients moved from complexity to clarity, from worry to confidence.
“Gary transformed my financial future starting in 1989... I thank God for leading me to him. He has never let me down.”
— Doug Miller
“Gary consistently understands our values and goals… His integrity is evident.”
— Greg & Robyn Rauen, Founders of World Compassion Network
“You taught us not just about finances, but about vision and purpose. Your care and wisdom are rare.”
— Rex Bruick, Founder of Foot Solutions
Let’s build a financial foundation rooted in your values, designed for your future, and strong enough to bless generations.
20 minutes to discuss what matters most and ensure you’re on the right track.
The information provided on this site is for educational purposes only and is not intended as investment, tax, or legal advice. Please consult your qualified professional before making any financial decisions.
Testimonials represent individual client experiences and do not guarantee similar outcomes. No compensation was provided for these testimonials.
Securities and investment advisory services offered through qualified registered representatives of MML Investors Services, LLC. Member SIPC. Supervisory Office: 900 East 96th Street, Suite 300, Indianapolis, IN 46240, (317) 469-9999. Woolman Financial Group is not a subsidiary or affiliate or MML Investors Services, LLC or its affiliated companies.
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