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Finances Simplified • Future Secure

About O'Reilly Financial Services

Meet Dennis O'Reilly

Financial coach, educator, and lifelong learner—here to walk with you toward financial clarity.

Learn More About Dennis O'Reilly
Portrait of Dennis O'Reilly from O'Reilly Financial Services
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MEET YOUR COACH

Why I Do This Work

For more than 25 years, I worked in education—teaching math, leading schools, and serving families with clarity, trust, and accountability. Along the way, I developed a deep respect for the role financial understanding plays in people’s lives. I’ve seen firsthand how money impacts decisions, relationships, and peace of mind.

Financial coaching is a natural extension of that work. It’s not about formulas—it’s about people. I listen closely, ask the right questions, and help you move forward with practical steps and a clear sense of direction.

Read Dennis' Full BIO
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WHAT GUIDES MY WORK

Core Values That Shape Every Conversation

These values aren’t just principles I talk about—they’re the foundation of how I listen, coach, and build trust with every individual and family I work with. They guide my decisions, shape my conversations, and reflect what I believe matters most in this work.

Whether you think you can or you think you can’t, you’re right.

— Henry Ford

Core Values

  • Accountability
  • Active Listening
  • Compassion
  • Education
  • Empowerment
  • Encouragement
  • Honesty
  • Humility
  • Integrity
  • Partnership
  • Trust
  • Servant
  • Relational
  • Respect
  • Accountability
  • Active Listening
  • Compassion
  • Education
  • Empowerment
  • Encouragement
  • Honesty
  • Humility
  • Integrity
  • Partnership
  • Trust
  • Servant
  • Relational
  • Respect
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OUR STORY

A Lifetime of Lessons, Leadership, and Stewardship

I believe it’s only fitting to share about my parents if you are to get a clear picture of me and my financial background. My mom and dad grew up on the south side of Chicago. Gloria, my sweet mom, was a nurse for three decades of her life, graduating from Loyola Chicago nursing program. Before giving herself to nursing, she and my dad raised seven boys, and yes, there are some great stories to tell. My parents sacrificed much to send their kids to private schools. I helped with school tuition by working two jobs in the summer of my junior and senior years to offset the cost at Benet Academy, a college prep high school located in Lisle, Illinois. Some of the best learning of fiscal practices came during my high school years with the study of Econ I & II.

Richard J. O’Reilly, my dad, served in WWII as a sergeant in the U.S. Army, and upon returning home from the war, he was able to take advantage of the G.I. Bill that paid for his education at St. Joseph’s College in Collegeville, Indiana. My dad earned three different business degrees attending St. Joseph’s College: an accounting degree, finance, and economics degree. Dad spent some years working for the Formica Corporation, but most of his employed years of service involved helping businesses navigate financial distress, as well as restructuring companies to avoid bankruptcy. He proved quite successful using turnaround strategies, eventually putting those businesses back on the path of prosperity. A great deal of my financial aptitude I learned from my father, and the financial principles that guide me today were ingrained in me early by his wise counsel.

Picture of Dennis O'Reilly and his daughter

I have spent most of my adult years in education, starting in 1990 as a volunteer basketball coach while earning a secondary teacher cert and teaching, of course, Math for sixteen years. I earned an MA in Educational Leadership with Chapman University and worked in school administration for twenty-five years, with thirteen of those years as a Superintendent with two different school systems in Tucson. Even as an administrator, I was still in the classroom educating students on the intricate ways to understand and use numbers, enhancing their problem-solving skills and use of critical thinking in mathematics.

Dennis O'Reilly and his son

I was able to create and establish start-up budgets for a newly developed private school in 2000 and for a charter school system that started in the Fall of 2015 and later expanded to Colorado in 2018. I also had the privilege of serving on fundraising, development, educational and advisory committees over the years. Most significantly, I served on finance committees of three different school systems in Tucson, serving with business leaders, accountants, engineers and others who have an understanding of financial principles related to budgeting, financial aid, scholarship monies, grants, tax credits, assets, liabilities, capital improvements, insurance cost, contingency funds, tuition percentage hikes, salaries and benefits, etc...

Dennis O'Reilly and his family

No matter the role or responsibility, the best part of my work over the years has always been the people, young and old. Getting to know another person and their story, having honest communication, and with that open communication developing a relationship built on trust and respect, mutual understanding, and a positive, encouraging rapport with another. It stimulates the soul when a person establishes and nurtures a connection with another. I promise, our time together will be educational, encouraging, and enlightening. Most of all, I want to help you and your family so that you can feel financially secure about the future.

With hard work, perseverance and self-belief, there is no limit to what you can achieve.

— Roy T. Bennett

Ready to take the next step toward financial clarity? Let’s begin with a conversation.

Sometimes the first step is simply having someone to talk to. If you’re ready to explore what’s next, I’d be honored to walk with you through it.

Schedule Your First Coaching Session
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Finances Simplified • Future Secure

At O’Reilly Financial Services, we empower individuals and families to take control of their finances through personalized coaching rooted in integrity, encouragement, and practical wisdom.

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