Ryan is a seasoned professional in all things finance and ran a successful investment blog and podcast while in college. Ryan is a Cincinnati native and attended St. Xavier High School, an all-male college preparatory school, where he won multiple awards and honors for his community service while there, including the "Aruppe Senior Service Award", which is given to one senior at graduation for their volunteerism during the last four years. Ryan considers this award to the biggest honor in life because St. Xavier has a motto of "Men For Others" and he wanted to embody that motto in everything he did.

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Post graduation, Ryan attended the University of Dayton on a full-academic scholarship where he majored in engineering and finance. Ryan did engineering research for the Air Force Research Laboratory. He was also Vice President of his fraternity, Phis Sigma Kappa, and was also on the Executive Board of the Interfraternity Council where he was the Community Service Chair. After a successful four years at the University of Dayton, Ryan transferred to the University of Cincinnati where Ryan graduated Magna Cum Laude with Bachelor of Business Administration in Finance. Ryan was part of Johnson Investment Council while there and "spent most of his time in the investment lab" on campus.

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Professionally, Ryan has worked at Reynolds & Reynolds in Dayton, Ohio doing corporate finance. He then had a stint in Atlanta, Georgia working for Synchrony Financial as a part of their Business Leadership Program before leaving to come back to his roots in Cincinnati where he worked at U.S. Bank in their Cincinnati headquarters. Before starting Cullen Investment Group, Ryan was doing wealth management at Morgan Stanley where he did much of the financial planning for the "great lakes region". However, Ryan knew that is not what he was called to do, because while there is nothing wrong with helping the ultra-wealthy, he didn't want to ONLY help them and he felt that there were so many people out there who didn't necessarily have tens of millions of dollars but could use his help, so Cullen Investment Group was born.

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Ryan sits on the Board of Directors and is the Treasurer of RENEW, a non-profit that provides resources to low-income individuals in eight key areas in things like affordable healthcare, housing, childcare, reliable transportation, job training and education and financial literacy. Ryan conducts free financial planning and financial literacy lessons to these individuals because these are oftentimes the most overlooked people by big financial services firms. Additionally, Ryan serves on the Board of Directors of AchievePoint Academy, which is a blended learning school for many low-income, minority, or disadvantaged students. Many of these students have either dropped out of school, struggle in the traditional school system, or have "termed out" aka they're too old to re-enroll into the public school system. This school helps students receive their high school diploma while also teaching them valuable life skills.