The R.U.D.D.E.R. Method

Our Proprietary Planning Process
A Plan That Doesn't Just Sit in a Drawer

Most financial plans are built once, filed, and forgotten. The R.U.D.D.E.R. Method is different. It's a six-step, ongoing process that keeps your plan aligned with your life, not the other way around.

See if You’re a Fit

Review & Recognize

Uncover & Understand

Design & Develop

Discuss & Decide

Execute & Empower

Reassess & Refine

Close-up of a person in a red jacket gripping a wooden ship's wheel at sea.

Featured In

Close-up of a compass resting on rough ground with warm, blurry bokeh lights in the background.

Why Process Matters More Than a Single Plan

Most people don't fail financially because they lack smart advice. They fail because they never had a consistent, disciplined process: something that could adapt as their life changed.

Mark and Jeff built the R.U.D.D.E.R. Method over years of working with families navigating retirement, business transitions, estate decisions, and everything in between. It's not a checklist. It's a framework for how we think, how we communicate, and how we keep your plan working.

Every client relationship at Chesapeake Financial Planners runs through this method, from the first Fit Call to the ongoing relationship that follows.

Six — structured steps, each with a clear purpose and output
One — coordinated plan, across tax, investment, insurance, and estate
Ongoing — reassessment as your life, goals, and the markets evolve

Chesapeake Financial Planners

5.0

Based on 11 reviews

review us on

Joyce Ducksworth

2 weeks ago

I have had the pleasure of entrusting my finances with Jeff and Mark for many years. Their expertise and advice are invaluable. My portfolio has grown significantly and has allowed me to retire comfortably with tremendous financial security. Mark is always available to answer my questions and provide solutions. I highly recommend Chesapeake Financial Planners.

stephen kinsley

2 weeks ago

Mark and Jeff have been my retirement advisors since 2011 and I could not be happier with them. They are knowledgeable and easy to talk with. They respond quickly to any questions and clearly explain all my options. I have been retired for 5 years and am fully confident that my financial future will continue to improve as it has so far with them. I would recommend them to anyone, and I only wish that I had met them sooner.

Bob Burris

1 month ago

I have been working with Mark and Jeff for 10+ years. I recently asked for a review of my financial plan and was provided outstanding feedback that provided me a much better solution.

Kim Wright

2 months ago

I am delighted with LPL. They've stayed with me for years and Jeff Judge has been exceptionally helpful. I've gotten good advice. He's managed my assets professionally and has always been available answer my questions.

He helped me consolidate several accounts into one manageable asset. He took the guesswork out of what could have been a complicated process.

I trust him to be there and guide me through issues in which I have no expertise. But he does this all the time and has proven to be trustworthy.

I do recommend Mr. Judge. You will not be disappointed.

Sharon Lewis

2 months ago

My husband and I met Mark and Jeff in 2014 when my husband left his job after 23 years. We met with Mark and Jeff to decide where to invest his retirement money. Before that decision was made, they took their time to understand our entire financial picture and based on that they gave us several options on where we could invest. They were very easy to talk with and made the conversation easy to understand. They are easy to get in touch with if you have questions and provide answers quickly. When it came time for me to retire, I also rolled my retirement investments into accounts managed by Mark and Jeff. We have also setup our estate planning as well as long term health planning based on advice we have had in review meetings in the years following our initial meeting. We have even referred our daughter and son in law to them. Highly satisfied with the investment service and customer service.

Andrew Benner

3 months ago

I check in with Mark a couple times a year and he always helps me keep my money that he manages growing. He also helps us with general advise regarding the type of places our 401k money should be (growth vs value, etc)

Mark Gray

5 months ago

Jeff has been helping me since 2014 with life insurance and retirement investment products. After a bad experience with a big insurance company, I found Mark and I’ve been working with him ever since. I’m successfully retired now and will begin drawing on my investments this year. I highly recommend Chesapeake Financial Planners for your retirement planning. – Mark G.

David Carrington

6 months ago

Jeff has been my financial advisor/ planner for several years. He has always guided me in the right direction and I have seen my retirement account continuously moving in the right direction. During the current uncertainty of the financial world right now Jeff has given me peace of mind that I continue to be in a safe and secure position with my finances. Jeff is very professional and quick to respond to my emails. As I approach my retirement years it is comforting to know my finances will be there when I need them.

Matt Hurson

6 months ago

I have been working with Jeff Judge and Chesapeake Financial Planners for about 3 years. Jeff has provided timely and well considered advice and acted promptly when I've needed access and changes to my portfolio. Highly recommend their services.

John Komoroski

7 months ago

We have worked with Jeff at Chesapeake Financial Planners for over 10 years. Throughout that time he has provided valuable investment and retirement information. Our investments have navigated this turbulent market far better than expected. Thank you Jeff.

Charles Gaither

7 months ago

I've been working with Chesapeake Financial Planners for a little over six years, and it's been an outstanding experience. They're knowledgeable, responsive, and consistently provide clear, personalized advice that aligns with my financial goals. Their long-term commitment and reliability have given me real peace of mind.

How the R.U.D.D.E.R. Method Works

Each step has a specific role. Together, they produce a financial plan that's comprehensive, coordinated, and built to last.

1. Review & Recognize

We learn about your situation in full: income, expenses, assets, liabilities, goals, and more. We introduce our team, firm, and process, and determine whether there's a mutual fit. If we move forward together, we define the scope of engagement, complete onboarding paperwork, and give you a clear list of documents needed.

What happens in this meeting: Learn about your full situation / Introduce our team, firm & process / Decide if there's a mutual fit / Define scope & complete engagement papers / Review onboarding process & next steps / You receive your document checklist

What comes next: Schedule remaining R.U.D.D.E.R. meetings / Docs needed within 1 week

2. Uncover & Understand

We discuss your values, priorities, timelines, and how you envision retirement. We review the documents you've collected, confirm the data, and ask the questions that surface what's really driving your financial picture, including the risks and opportunities most advisors don't surface until it's too late.

What we do in this meeting: Discuss values, priorities & timelines / Explore how you envision retirement / Review collected documents & confirm data / Identify risks to a successful retirement / Identify areas of opportunity

What we surface: Constraints & non-negotiables / Areas for growth / High-level analysis / Quick optimizations that can be made now

3. Design & Develop

This step happens internally. Our team builds strategies that align your resources with your stated goals and priorities. We develop recommendations across all areas of financial planning, map the priorities and sequencing, assign task ownership, and produce a clear roadmap that connects every action to an outcome. The plan goes through peer review before it comes to you.

What we build: Strategies aligned to your goals / Recommendations across all planning areas / Priority & sequencing map / Task ownership assigned: you, Chesapeake & outside professionals

Output: Clear roadmap connecting actions to outcomes / Internal peer review completed / Plan ready for your review

4. Discuss & Decide

We walk through every proposed strategy together: what it is, why it matters, and what problem it solves. We compare options and tradeoffs (costs, complexity, risk, flexibility, and tax impact), answer your questions, and confirm priorities so the path forward feels clear and realistic. We also capture the risks of inaction and make final decisions on who does what, in what order, and when.

What we cover: Review each strategy: what, why & what it solves / Compare options & tradeoffs / Answer questions & confirm priorities / Capture risks of inaction

Output: Final decisions locked / Clear next steps: who, what order & when / Nothing moves without your agreement

5. Execute & Empower

We turn decisions into an implementation checklist with clear owners and dates. We coordinate account openings, reallocations, and transfers, implement agreed insurance and policy changes, and align paperwork and timing with outside professionals. Equally important: we provide the clarity and education you need on the "why" so you know what happens next and stay engaged without feeling overwhelmed.

Execution includes: Implementation checklist with owners & dates / Account openings, reallocations & transfers / Insurance & policy changes confirmed / Coordination with outside professionals

Empowerment means: You understand the "why" / You know what happens next / You stay engaged without feeling overwhelmed / No black boxes

5. Execute & Empower

Execution includes: Implementation checklist with owners & dates / Account openings, reallocations & transfers / Insurance & policy changes confirmed / Coordination with outside professionals

Empowerment means: You understand the "why" / You know what happens next / You stay engaged without feeling overwhelmed / No black boxes

With our R.U.D.D.E.R. method™, you gain a clear path forward—one that adapts with your life, not just your portfolio. First, we Review where you stand and Recognize the patterns and risks shaping your finances. Then we Uncover your priorities and Understand what truly drives your decisions. Together, we Design and Develop a strategy that aligns with your goals, before Discussing and Deciding on next steps that feel right to you. From there, you Execute with confidence and Empower yourself with tools and insight, not guesswork. As life evolves, we continually Reassess and Refine your plan, so nothing gets stale or out of sync. The result? You stay in control with a trusted guide beside you and clarity replacing the chaos.

Chesapeake Financial Planners R.U.D.D.E.R. Method™

Hover over a step below for instant details on that stage.

Hover Over a Step to Begin

Use the R.U.D.D.E.R. steps above to quickly navigate and review the key activities, focus areas, and deliverables for each of the six stages in our project methodology.

Quick Tip:

This panel will update dynamically as you move your mouse over the steps.

(Note: On touch devices, tapping a step will activate the hover state.)

The R.U.D.D.E.R. Method Works Best For:

This isn't a one-size-fits-all process, but it is designed to handle financial lives that have grown complex.

Pre-Retirees & Retirees - You're within 10 years of retirement or already there. The questions around income sequencing, RMDs, Social Security timing, Medicare, and estate coordination all need a coordinated answer, not five separate advisors.

Business Owners - Your business and your personal finances are deeply intertwined. Exit planning, business valuation, entity structure, and succession planning require a process that looks at both sides of that equation simultaneously.

Professionals in Transition - A career change, an inheritance, a divorce, the sale of a business: major life transitions require a financial plan that can be rebuilt around new realities quickly and without starting from scratch.

Families with Complex Estates - When multiple accounts, properties, trusts, or business interests are involved, coordination matters more than any single smart decision. The R.U.D.D.E.R. Method keeps all the pieces talking to each other.

Wooden letter blocks spell out 'PROCESS SUCCESS' on a light desk backdrop, conveying achievement goals.

What Working With Us Actually Looks Like

From first conversation to ongoing relationship, here's how it unfolds.

The Fit Call

A 20-30 minute call to understand where you are, what you're trying to solve, and whether we're the right firm. No pressure, no pitch, just a real conversation.

The R.U.D.D.E.R. Engagement

We work through the six steps together: gathering, uncovering, designing, deciding, implementing, and establishing the ongoing relationship.

Ongoing Partnership

Annual reviews, proactive planning, and access when you need it. The R.U.D.D.E.R. cycle continues as your life evolves.

What Sets This Approach Apart

There are a lot of financial advisors. Most of them are either product salespeople with a planning wrapper, or planners without a disciplined process. The R.U.D.D.E.R. Method is neither.

It's a structured, repeatable process that every client goes through because we believe the quality of the process determines the quality of the outcome, not just the quality of the market.

Fiduciary, always — We're a fee-based firm. We don't earn commissions on products we recommend. Our advice is aligned with your interest, not a product manufacturer's margin.

Coordinated, not siloed — Tax, investment, insurance, and estate planning are not four separate conversations at CFP. They're one coordinated plan, and the R.U.D.D.E.R. Method keeps them that way.

Built to evolve, not expire — The final step isn't implementation. It's reassessment. The R.U.D.D.E.R. cycle repeats because your life doesn't stop changing after the plan is built.

You decide, we execute — Nothing moves without your understanding and agreement. The Discuss & Decide step isn't a formality; it's where the plan actually becomes yours.

CFP^® and CPA^® credentialed advisors — Mark and Jeff both hold advanced planning credentials. The R.U.D.D.E.R. Method is grounded in the same disciplined frameworks that define professional financial planning practice.

Frequently Asked Questions

The R.U.D.D.E.R. Method is Chesapeake Financial Planners' proprietary six-step financial planning process: Review & Recognize, Uncover & Understand, Design & Develop, Discuss & Decide, Execute & Empower, and Reassess & Refine. Having a named, repeatable process matters because it creates consistency. Every client gets the same disciplined approach, not a plan that depends on which advisor you happen to draw, or how thorough a given meeting turns out to be. The method also makes it easier to know where you are in the planning process and what comes next, which reduces confusion and builds trust over time.

The initial engagement, from the Fit Call through the Execute & Empower step, typically takes 60 to 90 days, depending on the complexity of your situation and how quickly we can gather the necessary information. The sixth step, Reassess & Refine, is ongoing and continues as part of your regular advisory relationship. We don't rush the front-end steps to get to implementation faster. Moving too quickly through Review or Uncover is how planning mistakes get made.

Yes. Every client relationship at Chesapeake Financial Planners runs through the R.U.D.D.E.R. Method. It's not an optional add-on or a premium tier; it's how we plan. The method scales to the complexity of your situation: a pre-retiree with multiple accounts and a pension decision will have a more detailed Design & Develop phase than a younger professional just establishing their plan, but the framework itself is consistent. That consistency is part of what makes our advice reliable over time.

Fiduciary means we are legally and ethically obligated to act in your best interest, not in our own financial interest, and not in the interest of any product manufacturer or fund company. Chesapeake Financial Planners is a fee-based registered investment adviser. The R.U.D.D.E.R. Method was designed within that fiduciary framework, which means the Design & Develop step produces recommendations that are genuinely the best fit for your situation, not the recommendation that generates the most compensation for us. It's a meaningful distinction that's worth asking about with any advisor you consider.

Yes. We work with clients who are transitioning from another advisor, clients who have a partial plan built elsewhere, and clients who've never worked with a planner at all. The Review & Recognize step is specifically designed to assess what's already in place: what's working, what's outdated, and what's missing. If you have an existing plan, we don't discard it. We evaluate it honestly and build from what's worth keeping. The transition process is handled carefully to minimize disruption to existing accounts, positions, and beneficiary designations.

Tax planning is fully integrated into the R.U.D.D.E.R. process; it's not an add-on and it's not outsourced to a separate engagement. It's addressed in the Review & Recognize step (where we assess your current tax situation), incorporated into the Design & Develop step (where recommendations are built with tax efficiency in mind), and revisited in the Reassess & Refine step as laws change or your income situation shifts. We work closely with your CPA or tax preparer where appropriate, and if you don't have one, we can help you find one. We do not prepare tax returns ourselves, but tax strategy is a core component of what we do.

It includes annual reviews, but it's more than a scheduled meeting. The Reassess & Refine step means we're proactively monitoring changes that affect your plan, not just waiting for you to call. That includes changes in tax law, significant market moves, updates to estate rules, changes to Medicare or Social Security policy, and life events you've told us about. When something material happens, we initiate the conversation. We also conduct formal annual reviews where we revisit your goals, update your plan, and confirm that the strategies in place still make sense for where you are now versus where you started.

Both spouses are part of the process from the beginning. The Uncover & Understand step is specifically designed to surface each person's values, priorities, and concerns, not just the household's financial data. In our experience, one of the most common points of financial friction in marriages is when a financial plan is built around one spouse's perspective and the other never fully bought into it. The R.U.D.D.E.R. Method is built to create alignment between spouses, not just a plan for the household "lead." The Discuss & Decide step requires agreement, not just approval, from both parties before implementation begins.

Business exit planning is one of the most complex planning scenarios we work with, and the R.U.D.D.E.R. Method is well-suited to it because of its coordination requirements. In the Review & Recognize step, we assess business ownership structure, entity type, and how the business fits into the owner's overall balance sheet. The Design & Develop step can include exit strategy scenarios (sale to third party, internal succession, ESOP, gifting), income replacement planning, and tax impact modeling for different exit structures. We coordinate with your business attorney and CPA through the execution phase. For many business owners, the exit is the most significant financial event of their lives; we treat it that way.

The Fit Call. It's a 20-30 minute conversation with Mark or Jeff, no pressure, no sales script. We'll ask about where you are, what you're trying to solve, and what's made financial planning feel complicated or incomplete in the past. You'll leave the call knowing whether we're the right fit, and we'll know whether we can genuinely help. If we're not the right fit, we'll tell you, and if possible, point you toward someone who is. The call costs nothing and doesn't commit you to anything. It's just a conversation.

*Advisors are only obligated to apply the fiduciary standard in advisory relationships. They are not legally obligated to apply the fiduciary standard when working in Brokerage only relationships

**Mark Rossbach is the only advisor who has attained the RICP and CPA Designations and Jeff Judge is the only advisor who has attained the CFP, ChFC and CLU Designations

The R.U.D.D.E.R. Method

Our Proprietary Planning Process
A Plan That Doesn't Just Sit in a Drawer

Featured In

Why Process Matters More Than a Single Plan

How the R.U.D.D.E.R. Method Works

1. Review & Recognize

2. Uncover & Understand

3. Design & Develop

4. Discuss & Decide

5. Execute & Empower

5. Execute & Empower

Chesapeake Financial Planners R.U.D.D.E.R. Method™