At Woolman Financial Group, we guide business owners, executives, and professionals through life’s most defining financial transitions. Whether you’re preparing to retire, exit your business, or plan for your family’s future, we help ensure your decisions reflect your vision, not just your balance sheet.
We offer specialized services to help you finish well, with clarity, confidence, and lasting peace of mind.
Create a Clear, Automated Plan for Every Dollar You Earn
Even high-income families can feel financial drift when income flows in without a clear plan.
Cash flow optimization replaces uncertainty with a simple system that aligns your earning, spending, saving, and investing. All income is first directed into a central account, then automatically allocated to lifestyle costs, tax reserves, savings, and long-term opportunities.
This structure protects against lifestyle creep, ensures consistent savings, and brings real-time clarity on what’s available to spend or invest.
The result is greater control, confidence, and progress without restrictive budgets or guesswork.
Secure Your Foundation and Grow Without Fear
Before building wealth, you need to protect it. Protection planning is about safeguarding what you’ve already built—your income, your business, your family—from risks that could undo it all.
Many clients come to us believing their current insurance coverage is "good enough" until we show them how fragmented or outdated their risk strategy has become. We evaluate every layer of exposure, including disability, liability, long-term care, health events, even lawsuits, to identify gaps and proactively close them.
Our strategies aren’t designed to sell products. They’re built to give you freedom: the freedom to grow your business, invest in your vision, and make bold decisions knowing your foundation is secure.
When you no longer fear the worst, you can confidently pursue your best.
Turn Your Assets Into Retirement Income Strategies Designed for Long-Term Reliability
You’ve spent your life accumulating assets. But retirement isn’t about accumulation. It’s about conversion. How do you turn what you’ve built into income that lasts?
Our retirement income planning process is designed to answer that question with precision. We don’t just map out withdrawal rates.
We build a visual income blueprint that shows how all your assets can work together to create consistent, tax-efficient cash flow. This includes investments, pensions, Social Security, annuities, business equity, etc.
And because market volatility doesn’t stop when you retire, we include strategic guardrails that preserve your plan when conditions shift.
You don’t want to guess your way through retirement. You want a strategy that frees you to live fully so you can enjoy retirement with greater clarity and confidence.
Secure Your Foundation and Grow Without Fear
You didn’t build your business to walk away from it casually. When the time comes to exit, you want to do it right, with dignity, clarity, and control.
We help business owners turn decades of work into lasting wealth. That means analyzing value drivers, preparing the business for transition, and creating a personal financial bridge that aligns with your future.
Whether you’re passing the company to family, key employees, or a third-party buyer, we coordinate with your CPA, attorney, and internal team to make sure the process honors both your financial goals and your personal values.
A successful exit isn’t just about selling for the highest number. It’s about finishing with the same intention that got you here in the first place.
Pass On More Than Wealth. Pass On What Matters Most.
True legacy isn’t measured in net worth. It’s measured in the impact your life continues to have after you’re gone.
We help families design estate strategies that reflect their deepest values and create harmony across generations. That starts with asking the right questions: What do you want your children and grandchildren to know? What causes matter most to you? What traditions should continue?
Our process integrates legal tools (like trusts, wills, and tax strategies) with relational elements like family governance, giving plans, and legacy letters.
Because your wealth should transfer more than assets. It should transfer wisdom, generosity, and purpose.
Manage Your Lifetime Tax Exposure with Strategies Tailored to Your Long-Term Plan
Taxes can quietly erode everything you’ve worked for. Not just this year, but across your lifetime.
Our tax diversification process helps rebalance your exposure across tax-deferred, tax-free, and taxable vehicles, giving you more control and flexibility in retirement.
We analyze your "tax buckets," coordinate Roth conversion timing, and design smart withdrawal sequencing to help you minimize your overall burden over decades, not just in the next filing season.
We also collaborate directly with your CPA to make sure every piece of your financial plan supports your tax strategy.
It’s not about avoiding taxes. It’s about managing them with wisdom, so you can use more of what you earn to live, give, and grow.
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.
CRN202504-2333515
