A retirement plan you can actually live on — and feel good about.
Our mission is to work closely with our clients to design financial strategies that provide confidence and clarity while also helping to protect their future. Using customized plans that are created through a true partnership, we empower our clients to weather the inevitable changes that our complex financial world presents.
Gary D. Penn
Founder & CEO — Gary Penn Financial & Insurance Strategies
Gary D. Penn is the Founder and CEO of Gary Penn Financial & Insurance Strategies, a retirement-focused advisory firm dedicated to one mission: helping everyday Americans protect their money, protect their families, and protect their future.
Gary didn’t start his career in finance. After more than 20 years running high-end steakhouses — long hours, endless stress, and no true financial security — he made a major life change. Seventeen years ago, he walked away from the restaurant world to build something better: a business where he could serve people, make a meaningful impact, and create long-term financial stability without borrowing millions or taking huge risks.
He found that path through retirement planning, Medicare, life insurance, and safe-money strategies that protect people from market downturns and unexpected life events. Since then, Gary has helped thousands of seniors and families protect what they’ve built — using tools like:
- Fixed Indexed Annuities — to give clients growth without ever risking their principal to market loss.
- Long-Term Care & Hybrid LTC Plans — to help families avoid the emotional and financial devastation of long-term care expenses.
- Life Insurance with Living Benefits & Final Expense — to create tax-free legacies, protect spouses, and make sure no family carries a financial burden during life’s hardest moments.
A Personal Approach to Retirement Protection
Safe-money strategies, Medicare guidance, and income clients can count on.
- Indexed Universal Life (IUL) Strategies — to provide tax-free income, market-linked upside, and long-term wealth building, without the volatility.
- Medicare Planning — to guide clients through complex decisions and help keep them on the best plan year after year.
Gary built his business sitting at the kitchen table — listening to people’s stories, solving real problems, and helping clients understand options no one else ever took the time to explain.
He believes retirement planning shouldn’t be confusing. It shouldn’t be risky. And it shouldn’t be reserved for the wealthy. His approach is simple:
- Protect the client.
- Protect their income.
- Protect their family.
- Make every decision as if it were his own retirement on the line.
Gary once “retired” from the insurance business — but he came back for one reason: helping people brings him purpose. Whether he’s protecting someone from market losses, setting up tax-free retirement income, securing long-term care coverage, or helping a widow understand her options, Gary does this work because:
“If I can help one family avoid the financial pain I’ve seen others go through… If I can help just one person retire with dignity… Then this career is worth every minute.”
Today, Gary focuses entirely on serving clients, not recruiting agents. He partners with:
- Retirees and pre-retirees.
- Seniors needing Medicare guidance.
- Families wanting to protect income and assets.
- Individuals seeking tax-free retirement strategies.
- People who want guaranteed lifetime income.
- Adults planning ahead for long-term care.
- Anyone tired of losing money in the market.
He helps them build plans focused on safety, tax efficiency, guaranteed income, legacy protection, long-term care preparation, market-loss avoidance, and true retirement confidence.
Committed to Your Financial Independence
Personal service, clear guidance, and discipline—built to support your goals at every stage.
Gary Penn Financial & Insurance Strategies
Gary Penn Financial & Insurance Strategies was founded with the goal of assisting our clients in every aspect of their financial lives. We’ve provided the most personal service available, thus earning a reputation for excellence in our industry. For each of our clients we strive to help create financial stability and security to provide financial independence.
Our Commitment
Our staff consists of experienced professionals with a “hands on” approach to financial guidance. Not only do clients find our team members knowledgeable, but they also discover that our staff truly cares about making their dreams a reality. We do everything in our power to keep our clients focused on where they want to go, advise them on how to get there, and continually remind them of the importance of maintaining a disciplined approach to realizing their dreams.
Our Principle
Our company is based on the principle that education and understanding of one’s current financial situation is vital to successfully make prudent decisions concerning one’s future financial condition.
Our Mission
When we talk about the ways that wealth and financial stability can define the individual, it has little to do with a balance sheet, and more to do with a balanced life. True wealth is everything money can’t buy and time can’t take away.
Our mission is to work closely with you to design strategies that protect income, protect principal, and protect legacy — using plans built specifically for your goals, not generic templates.
