Broker Check
Ryan Bailey

Ryan Bailey


Born and raised in Ada, Oklahoma, Ryan took an interest in the world of financial services from an early age, starting his career in his father’s business, Bailey & Associates Financial Services. “If it wasn’t for my father, I wouldn’t be doing what I’m doing. [His] hard work and sacrifices were a solid example of how to support your family.”

Ryan and Macy married in 2013 and, combined, have three children: Shani, Austin and Jayci.

Devoted to his family, Ryan has spent many years cheering on the sidelines at sporting events for his now-adult son, previously a baseball player, and his youngest daughter who plays tennis. Ryan enjoys family gatherings and spending time outdoors, finding peace in all nature has to offer. “I could be on the lake all day long and not catch a single fish, and still have a great time,” he says.

Having earned his insurance license in 2006, Ryan’s own goals of building a fulfilling life for his family and his experience during the financial recession of 2008 defined his career trajectory. When he saw people losing their retirement savings that they had worked so hard for, he found that certain investments protected and grew the clients’ assets, and other products could provide a guaranteed lifetime income. Ryan recognized that his investment preferences were more conservative and focused in on a set of products and clients aligned with that approach.

In 2019, Ryan and his wife, Macy, bought Bailey & Associates Financial Services from his father, Richard. 

Ryan says he owes his success first and foremost to God. “Both my parents were instrumental in teaching me the importance of a relationship with God. Without that, I wouldn’t be where I am today. 

Protective, hard-working and humble, Ryan strives to educate clients as he would his own family. “The products are always changing,” he says. “My goal is to always understand what’s changing and how it effects the clients’ needs and wants.” In so doing, Ryan empowers clients, giving them the confidence to make good decisions and achieve fulfillment in the retirement of their dreams.