Personal Financial Management Oversight

Because Having a Plan Isn’t the Same as Sticking to It

See if You’re a Fit

Featured In

You’ve built a successful life and with it, a complex financial landscape that demands more than a one-time plan. You want to feel in control, make the right decisions, and know that nothing important is slipping through the cracks. That’s where our personal financial oversight comes in.

You stay in the driver’s seat; we help navigate. Using our R.U.D.D.E.R.™ method, we bring structure, clarity, and ongoing accountability to your entire financial life so you can move forward with confidence, not second-guessing. With us as your guide, you’re not just planning you’re following through.

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.

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.)

Scope of Service Options ✓AUM ✓Core ✓Advanced

Investments

Portfolio Reviews & Investment Advice
Asset Allocation & Rebalancing Strategies
Risk Tolerance
Dollar Cost Averaging Strategies
Concentrated Stock Positions Strategies
Withdrawal Strategies
Stock Option Analysis
Alternative Investment Strategies

Cash Flow

Contributions & Savings Strategies
Income & Expenses Analysis
Emergency Funding
Debt Management
Large Purchase Funding
Lending & Financing Analysis
Advanced Strategies for Irregular Cash Flow

Retirement

Retirement Outlook & Timing Analysis
Retirement Plan Contributions
Retirement Income Strategies
Social Security Optimization
Medicare Analysis
Stress Testing
RMD Planning & Execution

Insurance & Risk Protection

Review Existing Policies
Life & LTC Insurance Needs Analysis
Health Care Planning
Disability Needs Analysis
Property & Casualty Analysis
Creditor Protection
Complex Insurance Trust Strategies

Income Tax

Portfolio Gain/Loss Review
Tax Optimal Withdrawal Strategies
Roth Conversion Strategies
1040/1041 Analysis
CPA Coordination
Passive Income Analysis
Business/Real Estate Purchase & Sale Analysis

Estate & Charity

Beneficiary Audit
Guidance for Basic Estate Docs
Detailed Estate Flow Analysis
Charitable Gifting Strategies
Estate Attorney Coordination
Estate Tax Mitigation Strategies
Private Foundations & Endowments
Generational Transfer Planning

Family Wealth

Net Worth Statement
College Education Planning
Gifting Strategies
Lifestyle Change & Relocation Analysis
Caring for Aging Parents
What-If Scenarios
Special Needs Planning
Family Financial Counseling & Education

Business

Self-Employed Income Planning
Self-Employed Retirement Plan Selection
Entity Structuring & Asset Titling Review
Buy/Sell Agreement Analysis & Business Use of Insurance Strategies
Business Cash Flow & Debt Restructuring Analysis
Business Transition Options & Timing Analysis

Frequently Asked Questions

At minimum, you should meet with your financial planner at least once or twice a year, but the right frequency depends on the complexity of your life and how much is changing.

At Chesapeake, we don’t believe in “set-it-and-forget-it” planning. We build long-term relationships with regular check-ins and ongoing access between meetings.

Here’s what our clients can expect:

Regular reviews (typically 1–4 times a year, depending on your needs)
Proactive outreach when tax laws, markets, or your situation changes
Access to us year-round, you’re never waiting months to get help

Big life changes (retirement, a business sale, divorce, inheritance, career shifts) often call for more frequent check-ins. And we’re here for those.

Bottom line? We’re not just here when you need something. We’re here to make sure nothing falls through the cracks in the first place.

Probably less than you think.

At Chesapeake, we don’t believe financial planning should be reserved for the ultra-wealthy. We work with busy professionals, business owners, and families who are ready for clarity, whether they’re managing six figures or navigating a major liquidity event.

Our personal financial management and oversight starts at $2,500 to $7,500 per year, and investment management fees scale with your assets—starting around 1.30% for smaller accounts and decreasing as your portfolio grows.

We'll always be upfront about costs before any commitment, and we'll walk you through exactly what you get: proactive planning, real accountability, and a collaborative partner who's just a phone call away.

Inflation affects everything, from groceries to long-term retirement income. But with the right plan, it doesn’t have to derail your goals.

Here’s how we help clients adjust for rising costs:

Reassess your spending projections

Small annual increases can compound quickly. We stress-test your plan with higher inflation assumptions so there are no surprises later.

Optimize your investment strategy

Certain asset classes, like equities, real assets, or inflation-protected securities—may play a more important role when prices rise.

Review your cash reserves

Too much cash loses purchasing power in high inflation. Too little leaves you vulnerable. We help strike the right balance.

Evaluate income sources

Pensions, annuities, or fixed income might need to be supplemented with more flexible strategies that grow over time.

Tax efficiency matters more than ever

Inflation erodes returns, don’t let unnecessary taxes eat into them, too.

At Chesapeake, we don't just build a plan, we adapt it as life and the economy change. That's how you can work to stay ahead of inflation, instead of chasing it.

Yes, big life changes almost always mean big financial shifts.

Whether it’s getting married, having a child, changing jobs, selling a business, going through divorce, or losing a loved one, your financial plan needs to evolve with your life.

Here’s why updates matter:

Your goals may shift and your strategy should reflect that
Income, taxes, or benefits may change
You may need new insurance, estate planning, or cash flow strategies
Timing matters, the earlier we adjust, the more options you have

At Chesapeake, we don’t just build a plan, we walk with you through life’s transitions. When something big happens, you’re not starting from scratch, you’re simply refining the course.

Financial planning is the big picture.

Investment management is just one piece of it.

Here’s how they break down:

Financial planning looks at your entire financial life:
Cash flow and budgeting
Retirement timelines
Tax planning strategy
Insurance and risk management
Estate planning
Big life transitions (like selling a business or starting a family)

It’s about aligning your money with your goals and adjusting as life changes.

Investment management focuses on your portfolio:
What you’re invested in
Asset allocation and diversification
Performance monitoring and rebalancing
Aligning risk with your timeline and goals

At Chesapeake, we provide both, because your investments don’t exist in a vacuum. They should support your life, not lead it.

A lot more than most people realize.

Financial planning isn’t just about investments, it’s about helping you make smarter decisions with everything money touches. That includes:

Clarifying your goals so your money is working toward what matters most
Creating a retirement income strategy that balances taxes, longevity, and lifestyle
Navigating big life events like a job change, inheritance, business exit, or divorce
Planning for healthcare, education, or legacy
Coordinating with your CPA, attorney, and insurance pros so nothing falls through the cracks
Keeping you accountable when life gets busy or decisions feel overwhelming

At Chesapeake, we’re more like a financial concierge than a stock picker. We help you get organized, stay on track, and move forward with clarity—through all of life’s twists and turns.

Think of it as a deep dive into your financial life, with a clear, actionable plan coming out the other side.

At Chesapeake, our planning reviews aren’t cookie-cutter or one-and-done. They’re built to uncover opportunities, identify risks, and move you closer to your goals.

Here’s what we typically cover:

Goal clarification

What matters most to you right now and what’s changed since our last review?

Cash flow and savings check

Are you saving enough, spending smart, and using the right accounts?

Investment review

Are your investments aligned with your goals, timeline, and risk tolerance?

Tax Planning strategy

Can we lower your tax bill now and in the future?

Insurance and risk

Are you protected from financial curveballs without overpaying?

Retirement and income planning

Are you on track, or do we need to fine-tune your timeline or withdrawal strategy?

Estate and legacy considerations

Are your documents, beneficiaries, and intentions up to date?

You’ll leave with clear answers, prioritized next steps, and ongoing accountability, not a pile of paperwork.

Absolutely—because investments are just one piece of the puzzle.

Having a portfolio is great, but that doesn’t mean you have a plan. Financial planning connects the dots between your money and your life.

Here’s what planning helps with beyond investing:

Are your investments aligned with your goals and timeline?
Are you minimizing taxes across all your accounts not just earning returns?
Do you have a withdrawal plan for retirement or a future transition?
Are you saving the right amount and in the right places?
Are you protected if something unexpected happens?
Are you making the most of your current income and opportunities?

At Chesapeake, we bring it all together with your goals at the center. We don’t just manage portfolios, we manage financial lives.

The good news? You have options.

Just because the original student didn’t use all the funds doesn’t mean the money is lost—or automatically taxed. 529 plans are more flexible than many people realize.

Here’s what you can do with leftover 529 money:

Use it for other qualified education expenses

You can still use the funds tax-free for:

Graduate school or professional programs
Community college, trade schools, or certain certifications
Up to $10,000 per year in K-12 tuition
Up to $10,000 (total lifetime) toward student loan repayment for the beneficiary or their sibling

Transfer it to another beneficiary

529 plans allow you to change the beneficiary to another eligible family member, without taxes or penalties. That includes:

Siblings, children, grandchildren, cousins, parents, even yourself

This can be a great option if you have younger children or relatives who still have educational costs ahead.

Roll it into a Roth IRA

Thanks to SECURE 2.0 in 2024, you may now roll up to $35,000 of unused 529 funds into a Roth IRA for the original beneficiary, tax- and penalty-free, as long as:

The 529 account has been open at least 15 years
The Roth IRA contribution limits and income limits are met
Annual rollovers don’t exceed the IRA contribution limit

This gives leftover 529 money a new life as retirement savings.

Withdraw the funds (with taxes and penalties)

If you withdraw money for non-qualified expenses:

You’ll owe income tax on the earnings portion (not contributions)
You’ll also face a 10% penalty on the earnings

However, there are exceptions to the penalty if:

The student receives a scholarship (you can withdraw up to the amount of the scholarship penalty-free)
The beneficiary dies or becomes disabled

Keep it for future use

There’s no deadline for using 529 funds. You could save the balance for future education needs, a career change, or even a grandchild’s education down the road.

Want help deciding what’s best for your leftover 529 funds?

A financial planner can walk you through each option, estimate taxes and penalties (if any), and help you make a smart, low-stress decision that aligns with your family’s goals.

Yes, if it’s the right plan, with the right partner.

A real financial plan isn’t just a one-time document. It’s a strategy, a system, and a roadmap that helps you:

Avoid costly mistakes (like tax missteps, missed opportunities, or emotional decisions)
Make smarter, faster choices with less stress and second-guessing
Stay focused on your goals, even when life gets messy or markets get noisy
Create momentum because progress compounds over time

The truth is, most people don’t reach their financial potential because they don’t have a plan or they have one that’s gathering dust.

At Chesapeake, we combine data-backed strategy with real accountability. So yes, the right plan can change your future because it keeps you moving toward what matters most.

*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

Personal Financial Management Oversight

Featured In

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

Hover Over a Step to Begin

Investments

Cash Flow

Retirement

Insurance & Risk Protection

Income Tax

Estate & Charity

Family Wealth

Business

Frequently Asked Questions

Ready to stop second-guessing and start feeling in control?

Contact

About

Financial Planning

Perspectives

Resources

Services

Compliance