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We Help Values-Driven Families Finish Well

Strategic Guidance for Business Owners, Executives, Professionals, and Stewards Who Want Their Wealth to Reflect Their Purpose

We work with people who have spent their lives building something meaningful-a business, a career, a family, a future. Now they're ready to protect what they've built, enjoy what they've earned, and ensure it benefits generations to come.

Our clients come from a range of industries and life stages, but they share a deeper perspective. They are builders. They value clarity, trust, and wisdom. And they want their financial decisions to reflect something more than returns. They want them to reflect purpose.

Whether you’re growing a business, preparing for retirement, or planning your family’s future, we meet you at life’s defining transitions and help you move forward with confidence.

The People We Help

Legacy-Focused Business Owners

You’ve built more than a company. You’ve built a way of life. Not just for you, but for your family, your employees, and your community. But as you approach succession or exit, the weight of stewardship grows heavier.


You want to make the right decisions. Not just for tax strategy or valuation, but to protect your legacy, your people, and your family harmony.


That’s where we come in. We help you clarify your goals, structure your exit intentionally, and design a legacy that carries your values forward.

As one of our clients said,

"Gary consistently understands our values and goals... His care and concern for his clients and his integrity are evident."

Approaching-Retirement Executives

You've climbed the ladder, managed complexity, and achieved success. But now, as you approach retirement, the question shifts from "How do I grow?" to "How do I protect and enjoy what I've built?"

You don’t want guesswork. You want predictable income, a clear tax strategy, and the freedom to focus on what truly matters next. We help executives transition from earned income to retirement income with clarity and intention. We help you integrate your retirement accounts, Social Security, stock options, and benefits into one cohesive strategy.


You’ve led others. Now, let someone lead you through this next chapter with wisdom and care.

Wealth-Building Medical Professionals

You're driven by excellence, but your time is limited. You face a unique financial landscape: high income, high liability, and a maze of disconnected advice.

We understand the need for clarity and protection without complexity. Our work with physicians and professionals centers on streamlining strategy, shielding assets, and aligning your plan to the life you're working so hard to build. We speak your language: diagnostic, preventive, efficient.

You take care of others. We help take care of the future you’re building.

Faith-Based Family Stewards

Your faith is central to how you live, give, and plan. You want your wealth to serve a greater purpose: to reflect your beliefs and bless the generations to come.

You may be asking: How do I give generously without jeopardizing family security? How do I pass on values, not just valuables? We help you answer those questions with grace and wisdom.

From values-based estate planning to purposeful giving strategies, we help ensure that your stewardship leaves both a financial and spiritual legacy.

Your Questions, Understood

No matter where you are in your journey, the questions you face are deeply personal:

  • Will my family be secure if something happens to me?

  • How do I leave my business or career in a way that feels complete?

  • Is my financial strategy flexible enough to adapt as life evolves?

  • What will my children and grandchildren remember about my legacy?

At Woolman, we don’t rush to answers. We start with listening. And we stay with you for the long haul.

What You're Really Seeking

You want more than a portfolio. You want peace of mind. You want:

  • Confidence in a strategy designed to support income throughout retirement.

  • A business exit that preserves relationships and maximizes impact.

  • A plan that protects your family and honors your values.

  • The ability to give generously and live freely.

Many of our clients come to us after trying other solutions. They’ve worked with CPAs, attorneys, or financial advisors who operated in silos. They've used DIY tools or cookie-cutter plans. But they still feel uncertain.

You deserve a better way that integrates every piece of your financial picture with purpose.

If This Sounds Like You, You’re in the Right Place

Our clients are thoughtful, intentional, and values-driven. They seek clarity over complexity and purpose over hype. They want a guide who sees the whole picture, not just the portfolio.

If you value collaboration, integrity, and long-term relationships, we may be a strong fit. But if you're chasing the next hot trend or looking for someone to "just do what you say," we may not be the right advisor.

We serve best when there is trust, shared vision, and a desire to build something that lasts.

Let’s Begin the Journey Together

The decisions you make today will echo for generations. Don’t leave your financial future to chance or continue with strategies that haven’t delivered peace of mind.

Start with a simple 20-minute "Quality Control Check." No pressure. No obligation. Just a meaningful conversation about your life, your values, and your goals.

20 minutes to see how well we align and how we can help you achieve your goals.

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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