Our History

Bailey Financial Services, originally known as Bailey & Associates was founded in 1974 by Richard Bailey, whose vision for financial guidance was shaped by a deep respect for people, relationships, and community. Beginning as a small, hometown-based practice in Ada, Oklahoma, Richard built the firm on a simple but enduring belief: financial advice should be personal, trustworthy, and rooted in genuine understanding. That belief remains the cornerstone of the firm today.

As the firm grew, it remained intentionally relational. Richard’s approach emphasized listening first, taking time to understand each client’s circumstances, goals, and values before offering guidance. Originally focused on health and life insurance, the firm expanded its services over time to address the evolving financial needs of families, adapting thoughtfully as planning tools, investment options, and long-term strategies became more sophisticated.

Over time, the business naturally grew into a family-led firm as the next generation stepped in to continue its mission. Richard’s son, Ryan Bailey, joined the business in 2000, beginning a gradual transition rooted in shared values and long-standing relationships. In 2013, Ryan’s wife, Macy Bailey, also joined the firm, bringing additional depth and support to its client-focused approach.

In 2019, Richard formally entrusted the firm to the next generation, confident that the legacy he built centered on care, education, and thoughtful stewardship would continue to guide Bailey and Associates into the future. Ryan established Bailey Retirement Group, LLC, while Macy lead the day-to-day operations of Bailey and Associates, guiding the firm with professionalism, clarity, and a deep commitment to clients. Under the leadership, the firm has embraced modern tools and resources while preserving the personalized service that has defined it for more than five decades.

This transition allows us to provide enhanced resources and modern tools while preserving the personalized service, collaboration, and care that has defined Bailey Financial Services for generations.

What has not changed and will never change is our commitment to serving you and your family with integrity, consistency, and a long-term perspective.

Meet Our Team

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