Defining Purpose in Retirement

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A name rooted in family values

A name rooted in family values

Howard Bailey was originally founded as Davenport Financial Services in 2002. In 2011, we changed our name to something that better reflected our 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.

Howard Weade

Howard Weade, father of Davenport Financial Founder Ron Weade and grandfather of President Casey Weade, has been the greatest influence on our philosophy about investments and saving...

Ralph Bailey

Those in the Indiana education field have likely heard of the inspirational and outspoken Ralph Bailey. He has been, and is still known as, a mentor, teacher, principal, superintendent, leader, father, grandfather, great-grandfather, motivational speaker and much more...

Company Timeline

Ron Weade, father of Casey Weade, founds Davenport Financial Services.


Upon taking ownership of Davenport Financial, Casey and Chelsie rename the company to Howard Bailey Financial in honor of Casey’s grandfathers and two biggest childhood mentors, Howard Weade and Ralph Bailey. Howard Weade instilled the conservative investment approach to Casey as a child, while Ralph Bailey influenced the mentality of education and serving others, both key philosophies we hold on to today.


Casey begins providing retirement guidance to Midwest radio listeners on Fort Wayne’s local WOWO radio “Financial Safari” segment.


Casey authors and publishes his first book, “The Purpose-Based Retirement,” which provides an inside look at the Howard Bailey retirement planning philosophy, and Casey’s belief that it all begins with Purpose.


Marshal Johnson, CFP®, joins the Howard Bailey Team as Vice President after working as a financial advisor for 6.5 years.


Casey lands his first ongoing TV segment on Fort Wayne’s ABC21 to educate individuals on planning for a secure and independent retirement during the “Insight” segment for Financial Fridays.


Casey and Marshal Johnson partner together and launch “The Purpose-Based Retirement” radio hour on WOWO.


Casey begins hosting his TV show, “The Purpose-Based Retirement,” Live on Fort Wayne’s ABC21, co-hosted with Lee Kelso.


Casey speaks to 250 advisors from around the country at Advisor Excel’s annual event in Salt Lake City on best practices.


Howard Bailey moves into its first official “home,” located at 6526 W. Jefferson Blvd. in Fort Wayne, containing 4 conference rooms, as well as a front and back office.


After continued growth and reaching $100 million in regulatory assets under management, we become federally regulated by the SEC as a Registered Investment Advisor (RIA), and continue our dedication to following our Fiduciary standard for our clients and always making it a priority to act in their best interest.


Howard Bailey expands to its second location in the Midwest: first at 1251 N. Eddy St. in downtown South Bend, then to its current location, a 3-conference-room office at 1736 E. Day Rd. in the heart of Mishawaka, IN.


After 15 years with the company, our very first Howard Bailey employee retires. Barb Campbell joined the team with Ron Weade in 2002.


As an avid golf fan and participant in the Indiana Junior Golf Program throughout his childhood, Casey partners with the Indiana Golf Foundation to sponsor what is now titled the “Howard Bailey Junior Golf Tour.”


Retire With Purpose becomes our company tagline and is implemented into our logo, as well as TV and radio shows.


Inspired to continue helping individuals retire with meaning and purpose, Casey launches the “Retire With Purpose Podcast.” What began as a local program quickly turns into a national, and now world-wide platform that features top financial experts, authors, entrepreneurs and inspirational leaders.


Casey publishes his first best-seller, “Job Optional,” where he explains the Howard Bailey retirement planning philosophy, how it ties into your purpose and why we’re so passionate about bringing you to your best retirement. On July 2, the book lands on #1 for Amazon’s Hard Cover Hot New Releases in Retirement Planning. On August 9, it reaches #5 on the Wall Street Journal’s Best Selling Nonfiction E-Book list. From July 29 to July 30, “Job Optional” hits #1 on Barnes & Noble’s Business E-Book Nook list


The Howard Bailey Team moves into our current “home,” where we will continue to grow, evolve, educate and develop retirement plans driven by meaning and purpose.


After releasing over 100 episodes, the Retire With Purpose Podcast reaches 100,000 worldwide downloads.

A step above

Your Howard Bailey Financial includes three CERTIFIED FINANCIAL PLANNER™ (CFP®) professionals, as well as CFP® candidates.

As a potential or current client, collaborating with a CFP® professional provides you with the reassurance of attaining your financial goals. In addition to meeting a high standard of education and career experience requirements, CFP® professionals possess credibility at both an ethical and professional standpoint.

Prior to certification, CFP® practitioners must complete a CFP Board-approved financial planning curriculum—mastering almost 100 integrated financial planning topics (investments, insurance, retirement planning, risk management, etc.), while also committing to continued educational classes, including a code of ethics course.


Furthermore, CFP® professionals are required to pass a 10-hour CFP® Certification Exam that tests their financial planning knowledge on an integrated level and accumulate at least three years of personal financial planning experience.

In the final step, CFP® practitioners concede to a strict code of professional conduct, known as CFP Board’s Code of Ethics and Professional Responsibility. This clause lays the groundwork for an advisor’s commitment and ethical responsibility to the public, clients and employers. In addition, the Code of Ethics prompts CFP® professionals to remain fair and diligent when providing financial planning advice and services, putting your interests first.

Source: Certified Financial Planner Board of Standards, Inc.

“CFP® Certification: The Standard of Excellence Copyright ©2017, Certified Financial Planner Board of Standards, Inc. All rights reserved. Used with permission.”

Updated job optional book stack
Are You Job Optional*?

Casey Weade, Certified Financial Planner® and President of Howard Bailey, breaks down how to utilize our Retire With Purpose planning framework to customize a retirement roadmap that mirrors your values, goals and passions.

How can we make your day better?

Your Howard Bailey Financial includes three CERTIFIED FINANCIAL PLANNER™ (CFP®) professionals, CFP® candidates, and an entire support staff — all working hard to help you through one of life's biggest transitions.

Meet the Team
Careers with Purpose

Join our modest, nimble and goal-driven group of advisors, client services, operations and marketing professionals who thrive on building relationships — with each other, and with our clients.

Big Payback

We welcome our Howard Bailey friends and family to join us at the upcoming charitable events. This is our time to give back — won't you join us?