Business Details
24 Years
experience
Your Trusted Partner for Retirement Planning Solutions
Founded in 2002, Howard Bailey has evolved from Davenport Financial Services into a nationally recognized leader in retirement planning. Our philosophy, rooted in the values of our namesakes Howard Weade and Ralph Bailey, combines conservative investment strategies with a commitment to client education and individualized service. With over two decades of experience, we specialize in creating purpose-driven retirement frameworks that address liquidity, income, flexibility, and estate planning. Recognized as *Best Financial Advisor* for six consecutive years by Fort Wayne Newspaper Readers' Choice and named to Newsweek's Top Financial Advisory Firms in 2025, our team of CFP professionals delivers transparent, fiduciary-driven advice.We prioritize long-term client relationships through our Retire With Purpose methodology, which integrates financial planning with life's non-financial aspirations. Our expertise extends to tax optimization, risk management, and legacy planning, supported by a 15-year track record of SEC regulation as a Registered Investment Advisor. This combination of technical proficiency, ethical standards, and client-centric philosophy establishes our authority in retirement planning while maintaining the trust of over 20,000 email subscribers and a growing client base nationwide.
Services
Retirement Planning
Medicare Planning
Retirement Coaching
Estate Planning
Tax Optimization
Investment Management
Legacy Planning
Risk Management
Financial Education
Wealth Transfer
Details
- Year established: 2002
Highlights and features
- We have CFP professionals with decades of retirement planning expertise
- Our Retire With Purpose framework personalizes strategies to individual life goals
- Transparent fee structure with no hidden costs
- Recognized by Newsweek as Top Financial Advisory Firm in 2025
- Client-centric approach combining financial and non-financial retirement planning
Associations and certifications
- Certified Financial Planner Board of Standards
- Securities and Exchange Commission (SEC)
What people say
Most attentive group
Very informative advisors
Smooth and painless transition
Awesome to work with
Caring and professional manner
Services
Retirement Planning
Our Retire With Purpose framework creates customized retirement strategies addressing liquidity, income, flexibility, and estate planning. We combine conservative investment approaches with tax optimization techniques to build secure financial futures. Our process emphasizes purpose-driven decision-making that aligns with clients' life goals and values.
Estate Planning
We develop comprehensive estate plans that ensure efficient wealth transfer while minimizing tax liabilities. Our approach integrates legal documentation with investment strategies to protect assets for future generations. Services include wills, trusts, and beneficiary designation optimization tailored to individual family needs.
Retirement Coaching
Our coaching program helps clients navigate retirement's non-financial aspects through workshops and personalized guidance. We focus on purpose discovery, relationship building, and creating meaningful post-career lifestyles. The program complements financial planning with practical tools for emotional and social transition.
Tax Optimization
We implement tax-efficient withdrawal strategies and investment approaches to minimize retirement tax burdens. Our planning considers Social Security optimization, Roth conversions, and income distribution sequencing. The service integrates with overall financial strategies to maximize after-tax wealth preservation.
Investment Management
Our investment approach combines risk management with growth potential through diversified portfolios tailored to individual risk profiles. We employ conservative strategies focused on capital preservation while seeking optimal returns. Regular portfolio reviews ensure alignment with evolving retirement goals and market conditions.
People
Casey Weade
Founder & CEO
Certified Financial Planner with over 20 years of experience, author of best-sellers 'Job Optional' and 'The Purpose-Based Retirement'. Developed the Retire With Purpose framework and hosts the award-winning podcast of the same name.
Isaac
Financial Advisor
Experienced retirement planner known for clear investment explanations and personalized client education. Specializes in creating tailored retirement strategies that balance financial security with lifestyle goals.
Les McDaniel
Advisor
Seasoned financial professional with expertise in retirement income strategies and tax-efficient planning. Recognized for his consultative approach and ability to simplify complex financial concepts for clients.
Ryan
Financial Advisor
Specializes in comprehensive retirement planning with focus on client education and long-term relationship building. Known for attentive service and expertise in purpose-driven financial strategies.
Marshal Johnson
Vice President
Certified Financial Planner with over 15 years of advisory experience. Joined Howard Bailey in 2013 after successful career in financial services. Focuses on portfolio management and retirement income planning for high-net-worth clients.
Questions
What makes your retirement planning different from other firms?
Our Retire With Purpose framework uniquely combines financial planning with life purpose discovery, creating holistic strategies that address both monetary and non-financial aspects of retirement.
Do you work with clients outside Indiana?
Yes, we serve clients nationwide through virtual consultations and have office locations across Indiana and Ohio to better serve Midwest clients.
What credentials do your advisors hold?
Our team includes Certified Financial Planners (CFP), Retirement Income Certified Professionals (RICP), and advisors with advanced training in estate and tax planning.
How are your fees structured?
We use transparent fee-only compensation with no hidden costs or commissions. Fees are based on assets under management and clearly disclosed in our ADV Part 2 brochure.
What retirement resources do you offer?
We provide free educational resources including our Retire With Purpose podcast, weekly retirement articles, webinars, and the Job Optional best-selling book on retirement planning.
How do you handle investment risk management?
We employ conservative, diversified investment strategies tailored to individual risk tolerance, with regular portfolio reviews and adjustments based on changing market conditions and client needs.
Videos
Reviews (5)
Jane Sasur
Nov 04, 2021
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I had reached out to the Howard Bailey financial planners via Casey Weade's very educational Podcasts. I was impressed with Casey's relationships and contacts with various industry experts in the financial planning world, as well as his personalized, purposed-based, one/stop approach to retirement planning. Even though my husband and I live in California and communicate with Ryan, our primary (and awesome) financial planner in Indiana via Zoom, our meetings still feel like in-person, face-to-face encounters. We could not find anyone locally with the holistic approach and expertise they possess
Douglas Arnold
Nov 01, 2021
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Positive:Professionalism,Responsiveness
It is rare that in this day and age a company put such an emphasis on customer service. Howard Bailey is such a company, and I've gotten very good results by employing them.
It is rare that in this day and age a company put such an emphasis on customer service. Howard Bailey is such a company, and I've gotten very good results by employing them.
Robert Haverstick
Oct 24, 2021
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We have been with Howard Bailey approximately 8+ years. They are extremely knowledgeable, professional and have a genuine interest not only as a financial planner but take a great interest in our family. We have quarterly meetings where they review our account with us and make recommendations.They meet our every need. We highly recommend them.
Dan Drabik
Sep 20, 2021
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We received an invitation in the mail for a free meal at Ruths Chris just to sit an listen to a presentation. My wife and I had ZERO intention of signing up for anything! That was until we listened to Reid Braun present on how taxes were on sale currently and around how much our 401k will actually cost us in retirement. My wife and I listened and realized everything Reid spoke about was exactly what we were facing. So we decided to give it a whirl and book an appointment. We figured what harm would it be just to sit down with Reid and listen to what he had to say. It is probably
Rich Mullins
Sep 11, 2021
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We absolutely Love the Howard Bailey Inc in Mishawaka (and Fort Wayne as far as that goes)
We had a financial group for 30 years. We thought they were "ok" but after meeting and switching to Howard Bailey, we couldn't be happier! The former financial group didn't even try to keep our business, after 30 years!! No contact, no letter, no nothing! Where as Howard Bailey was happy to get our business! Our only regret is that we didn't do it sooner... Rich and Carole Mullins
We had a financial group for 30 years. We thought they were "ok" but after meeting and switching to Howard Bailey, we couldn't be happier! The former financial group didn't even try to keep our business, after 30 years!! No contact, no letter, no nothing! Where as Howard Bailey was happy to get our business! Our only regret is that we didn't do it sooner... Rich and Carole Mullins
