Developing personalized strategies to pursue better financial outcomes

Welcome to

Chesapeake Financial Planners

Working together to clearly define your personal, financial, and business goals.

Chesapeake Financial Planners is a financial planning practice that specializes in developing personalized strategies for closely held business owners, public/private corporate management, pre-retirees, and retirees.

Our purpose is to help our clients achieve better financial outcomes. This is pursued by working together to clearly define your personal, financial, and business goals, and holding you accountable every step of the way.

Our goal is to provide you the security that comes from knowing your family is prepared and protected, no matter what the future brings. By simplifying complex financial concepts, we provide the tools and resources to that aim to help you make better decisions for those who depend on you.

Connect with us today and find out how we can help you, your business, and your family thrive!

Our Team

Jeff JudgeManaging Partner

Mark RossbachManaging Partner

Eric ParnellChief Market Strategist

Nick DalessandroSenior Associate, Asset Management

Kaela FrenchmanAssociate, Asset Management

Evan CoffeyAssociate, Asset Management

Who We Serve

For decades, we've helped employees at several corporations maximize their employee benefits. We often find that executives know of their benefits but haven't had the time to create a thoughtful plan to capitalize on them.

What Sets Us Apart

Guidance on maximizing your benefits
Analysis of ESOs (employee stock options) and RSUs (restricted stock units)
Exploration of existing portfolio and recommendations for diversification
401(k) analysis to maximize contributions and after-tax Roth conversion strategies
Establishment of a cash contingency plan
Retirement prior to 65: health care coverage and retirement income plan

Helping You

We will thoroughly evaluate your retirement plan and other benefits and provide recommendations so you can take full advantage of your employer's offerings. You work hard every day and strive for excellence in your career. Let's work together to put a plan in place to make sure your financial and retirement plans work just as hard for you. Contact us today to start the conversation.

As an educator, your students are your priority. You work hard daily to give them the knowledge and skills they need to succeed. Unfortunately, it's all too easy to place financial and retirement planning at the bottom of your to-do list. Our team has worked with hundreds of educators and their families to help mitigate this burden from their shoulders. Let us be your financial and retirement planning advocates to guide you through your options and set a path to reach your goals.

What Sets Us Apart

Over two decades' worth of experience working with educators
403(b) retirement plan analysis and recommendations
Pension education and plan management: TRA, PERA, MSRS and others
Social Security analysis, demonstrating how these funds fit into your overall retirement picture

Helping You

We aim to help you maximize your often-complex benefits as an educator so you can focus on your career and family. If you're looking for guidance on your financial and retirement plans, and a better understanding of how all your benefits work together, you've come to the right place. Contact us today to start the conversation for a better tomorrow.

Not all advisors know the unique challenges small businesses face. Running your own business can be a lot to manage, including keeping your finances in check. We understand that you may not have the time to weigh your options or have the knowledge you need to make an informed decision. That's where we come in.

What Sets Us Apart

Recommendations on accounts for operating your business
Cash flow management strategies
Employee 401(k) retirement plan implementation and management
Selling your business
Tax minimization with access to CPAs

Helping You

Our mission is to help you maximize the capital that goes into running your business. Look to us to help you save time, better position your money, evaluate market trends, execute your business plan, manage your and your employees' investment and retirement plans, and more. If you're looking for a partner who has your back, contact us today to start the conversation.

As you transition from worker bee to retiree, you need a knowledgeable partner to help you determine how best to spend the money you worked hard to acquire. Look to us as your go-to retirement resource as you navigate the various situations that make this phase unique.

What Sets Us Apart

Withdrawal strategies: 401(k), 403(b), IRA, Roth IRA
Health and long term care
Required Minimum Distributions (RMDs) from retirement accounts
Tax bracket analysis with access to CPAs
Estate planning and philanthropy
Social Security decision making

Helping You

Our mission is to guide you through the often-complex transition into retirement. We will develop and help you execute a strategy that strives to help mitigate the stress of this unique stage of life and help you pursue sustainable results that meet your financial objectives. If you are looking for a partner who has helped hundreds of clients transition into retirement, contact us today.

Whether you saw it coming or were taken by surprise, any sudden life change can leave you with unanswered questions. For those going through a divorce, newly widowed, or facing high emotional stress, it's essential to take some time before making significant decisions. Look to us as the partner to rely on who can provide you with the unbiased and objective perspective you need.

Or maybe you've come into newly acquired wealth? One of the biggest mistakes we see as financial advisors are mishandling an unexpected windfall event. We are here to guide you through the uncertainties that come with inheritance or other instances of sudden wealth, bringing clarity, understanding, and intention to your new reality.

What Sets Us Apart

Your advocate in helping you determine how much you need to continue living comfortably for the rest of your life
Guidance on investing divorce settlement money which strive to generate a lifetime income
Experienced advisors in navigating a sudden inheritance, wealth from a newly sold business, or recently sold stock options
Knowledgeable in managing profits from an estate sale or an investment
Creating a new financial plan for your next chapter in life

Helping You

Our mission is to guide you through each step, ensuring you feel confident about your changing circumstances. We will develop and help you execute a new financial strategy based on your unique situation to work toward sustainable, long-term, real-life returns that meet your financial objectives. If you are looking for an advocate who has your back, contact us to start the conversation.

Our Services

We believe that no one person can know everything and it's for this reason that when you work with us, you have a team of advisors at your service.

Financial Planning

Financial planning helps you understand where you are today and create a roadmap to get you where you want to be. Our recommendations are personalized to you, whether you’re saving for retirement or need comprehensive planning and wealth management.

Our advisors have years of experience and will help you establish your goals, consider all aspects of your financial circumstance, identify action steps, and tailor an investment strategy to your goals.

Investment Management

Our goal is to meet you where you are today and make plans to get you to where you want to be tomorrow. Our advisors are dedicated to developing a strategy that will help you pursue your financial goals. We provide ongoing assessments, management, and adjustments to your investments as you go through life and your needs shift.

Our wealth management services will provide you with comprehensive planning and implementation of strategies for retirement, family, inheritance, insurance, estate, charitable giving, and tax planning. Working with one of our experienced financial professionals allows you access to thousands of investment and insurance options to fit your needs.

Retirement Planning

We can develop a clear financial plan to help you gain an understanding of how your investments, Social Security, and savings can all work together. Planning for retirement is not something that happens overnight.

Many of us have been saving for retirement since we began our careers, while others started later in life. The important thing to remember is that the nest egg you have saved needs to provide comfort and confidence, well beyond your working years.

Tax & Estate Planning

An effective estate plan ties together even the most complex financial scenarios. This means considering matters of both life and death that may involve incapacity, gifting, and charitable giving in addition to wealth transfer.

Taxes are often an afterthought but have a significant impact on virtually every aspect of a financial household. Proactive planning means that we’re carefully watching what may easily be a client's biggest expense.

Small Business Owner Strategy

You work hard every day to build a strong future for your company and its employees, and your dedication shows in the results you deliver to your customers and stakeholders.

We’re equally dedicated to the financial well-being of both you and your business. We offer access to quality investment and insurance strategies customized to address the individual needs of businesses of every size and in all stages of development.

Based on our thorough understanding of both opportunities and challenges you face, we can provide comprehensive strategies to address your business needs while delivering a high level of customer service.

Our Process

Our team works together to understand your situation, develop a plan to fit your goals and needs, perform periodic reviews, and provide the comprehensive ongoing service that makes our clients confident to recommend us to their family, friends, and colleagues.

Introduction

This is the first part of establishing a fruitful partnership, so be prepared! Our goal is to mutually establish our expectations and whether an ongoing relationship is a good fit. In this phase, we will identify your goals, priorities, preferences, and potential obstacles.

Exploration

Based on our first meeting, we now take a deeper dive into your individual financial situation. During this session, we begin to sketch a preliminary plan as we discuss your personal and financial goals more comprehensively. This phase is essential to developing a customized, comprehensive plan.

Planning

In this phase, we deliver an easy-to-follow roadmap that will help you work towards your financial goals. We will specifically address the areas most important to you, ensuring your customized plan is tailored to help address your goals. We also explain and educate you on the plan so you feel confident.

Ongoing Support

As your life circumstances facilitate a different approach to financial planning, wealth management, and savings options, we will be a constant presence to ensure that your plan transitions along with you. Your goals will inevitably shift over time, which is why we are here to update and evolve your financial plan proactively.