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Howard Bailey Announces Toledo Expansion and New Advisor 

FORT WAYNE, INDIANA, May 13, 2022 – Howard Bailey Financial, Inc., an independent retirement planning firm headquartered in Fort Wayne, announced the hiring of James “Jamie” Dewese as a Financial Advisor for their new Toledo office location.

In this role, Dewese will provide customized financial and retirement guidance to clients utilizing Howard Bailey’s proprietary planning process, the Retire With PurposeTM Framework. He will focus on helping clients define their unique purpose, coach them through their financial goals and develop financial strategies that align with the four key pillars of their L.I.F.E. plan.

At age 15, Dewese began working in retail, and following high school graduation, he continued building his own business over the course of 12 years. Dewese then went on to pursue a career in bank management, followed by five years specializing in investment and financial planning with an Ohio- based investment firm. These experiences sparked Dewese’s passion for helping others reach financial independence and prompted him to step into his current career of retirement planning.

Dewese graduated from Terra State Community College with a degree in Business Management. Additionally, he is an Investment Adviser Representative, and holds his Series 6, 63, 66 and 7 certifications. Dewese also possesses unique knowledge around the state of Ohio’s pension systems, specifically around the STRS, SERS and OPERS retirement accounts.

Casey Weade, Founder and CEO of Howard Bailey Financial, Inc., is excited to bring Dewese onto his growing team. “As a firm, we are in the process of expanding our footprint into the Toledo, Ohio, area with the addition of a new office location. By incorporating Jamie Dewese into the Howard Bailey advisory team, this not only means growth for us all personally, but further opportunity for us to continue our mission of helping others gain financial confidence. With his extensive career background, I am ecstatic to see Jamie carry that mission forward.”

“Joining Howard Bailey Financial presents an amazing opportunity for me to elevate my passion for connecting with others, building long-lasting relationships and creating a positive impact,” Dewese added. “I am excited to grow personally and professionally while helping clients plan their path to retirement with purpose,”

Dewese is married to Angie, and together they parent their two children: Michaela (22) and Zach (19).

Howard Bailey’s new Toledo office is expected to open early summer in The Town Center at Levis Commons.


Our mission is to elevate the meaning and purpose in the lives of others, allowing them to focus on where they can make the biggest impact today.

Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures.

And while we can't work with everyone, our goal is to provide value to everyone we meet. Our Retire with Purpose Podcast, TV Show and Radio Hour cover trending topics with some of today’s most successful retirees and experts in the field of finance. You can see those resources here.

We are a fee-based independent advisory firm. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here.


Howard Bailey was originally founded as Davenport Financial Services in 2002. In 2011, Davenport's name changed to something that better reflected the firm's business and philosophy — a combination of two great men who helped shape what Howard Bailey Financial, Inc. is today.

Howard Weade is the grandfather of Casey Weade. Howard lent much to the conservative investment approach that was ingrained in the mind of Casey, as well as the approach that the Howard Bailey team utilizes today.

Ralph Bailey is the grandfather of Casey Weade and father of Diann Weade. Ralph lent much to the character that Howard Bailey upholds every day, focusing on educating our clients and treating each as an individual.

Our name also reflects our family values. Casey founded Howard Bailey as a family company built upon developing a secure, independent retirement for each and every client. Our logo is a family tree that reflects strength, persistence, growth, resilience and, of course, the strong family values upon which we were founded.


Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment advisor. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. Certified Financial Planner Board of Standards Inc. owns the certification marks CFP®, CERTIFIED FINANCIAL PLANNER™ and CFP® (with flame design) in the U.S., which it awards to individuals who successfully complete CFP Board’s initial and ongoing certification requirements. The CLU® and ChFC® marks are the property of The American College, which reserves sole rights to their use, and are used by permission.