Our primary objective is to provide you with a comprehensive roadmap that consolidates all of the various financial components of your life into a centralized, integrated plan. We believe that financial planning is a process, not an event. As the markets, economy, opportunities, or personal circumstances change, we provide ongoing guidance to ensure your plan stays aligned with your goals. We offer practical insight, backed by analytical rigor, colored with the human aspects of investing, tempered with the reality of risk, combined with our unique approach of consolidation, integration and simplification.


  • Assessment of your goals, time frames, and risk tolerance
  • Asset allocation recommendations
  • Portfolio design and construction
  • Continuous portfolio monitoring, rebalancing, and maintenance
  • In-house trading team
  • Investment Policy Committee regularly meets to identify risks and opportunities to position portfolios accordingly
  • Ongoing portfolio manager evaluation


Through our individualized approach, we’ll gain an understanding of your specific goals, time frame, and risk tolerance. We’ll be by your side to guide you through historical evidence supporting various investment methodologies, allowing you to make confident, educated decisions. Together, we’ll determine the balance of risk and potential return that you’re comfortable with. As an independent fee-based firm, we are not limited to a specific pool of investments to choose from or restricted to proprietary funds (as is the case with many Wall Street firms and insurance companies).


Many advisory firms outsource their investment research. At Cassaday & Company, Inc., we have a robust, analytical process in place to ensure we are in complete control of our investment selections, asset allocations, models, and overall investment strategies. Our Investment Policy Committee (IPC)—consisting of over a dozen senior professionals—regularly reviews our clients’ holdings and asset allocation, market conditions, research studies, economic analysis, and other areas relevant to the investment process. This approach encourages regular collaboration and ongoing research to ensure that strategic decisions are vetted and thoughtfully considered before they can impact your portfolio.



  • Patented portfolio withdrawal strategies (DIESEL®)
  • Social Security analysis
  • Medicare analysis and private healthcare planning
  • Comprehensive retirement plan review
  • Employee benefits and pension plan analyses
  • Assessment of continuing care communities


  • Financial goal analyses and recommendations
  • Education planning:
    • Complimentary
      529 plan management
    • Ownership strategies for college savings plans
    • Financial aid guidance
  • Access to concierge medicine, life coaches,
    downsizing, and special needs professionals


Sound planning must support the adoption of any financial strategy. Our team of experts will work with you to help you analyze your financial circumstances and establish a customized plan to help reach your goals.

In our view, financial and retirement planning encompasses not only traditional investment strategies, but everything in your life with a dollar sign in front of it. For your plan to be most effective, components such as estate planning, tax management, Social Security, Medicare, insurance policies, and more must be considered in a holistic, integrated fashion. This planning exercise is part of our investment management process and does not involve additional fees or charges.*

Our collaboration of highly trained, experienced, and credentialed professionals in a fee-based environment presents a superior choice for investors seeking objective and impartial guidance about their financial situation.

*Under certain circumstances clients may choose to be billed hourly for planning and evaluation services that exceed, in the judgment of the firm, what would be considered reasonable. These hourly rates vary based on the nature of the planning. We discourage clients from hourly planning as we believe that proper planning is an ongoing process NOT an event. We recommend a fee-based approach on the value of the assets managed. This arrangement encourages a continuum of planning and investment management and eliminates many conflicts of interest inherent in other compensation arrangements.


  • Identification of tax efficiencies
  • Collaboration with your tax professionals
  • Tax loss harvesting
  • Charitable giving strategies
  • Accuracy verification of financial data, including cost basis of all previously held positions


We help identify tax efficiencies, collaborate with your tax professionals, evaluate and recommend charitable giving strategies, and aim to minimize capital gains taxes on your investments. It is important to remember that although minimizing taxes is important, attempting to achieve a proper balance of risk and return is our paramount concern.

Note: We are not a Certified Public Accounting (CPA) firm and do not prepare tax returns; however, we have CPAs on staff, as well as a network of reliable professional relationships, and can help match you with the right tax professional to meet your needs.


  • Insurance Audit: comprehensive analysis of life, disability, long-term care, and annuity contracts
  • Risk/ needs analyses, objective product recommendations, and implementation assistance for insurance and annuities
  • Group 401(k) management and oversight
  • Active involvement in insurance claim execution, contract reviews, and management
  • Long-term care advocacy

We will conduct a complimentary in-depth insurance analysis that includes an audit of your life, disability, and long-term care insurance policies. When necessary, we help coordinate changes to your policies, and will even help you through the claims process.

Annuities are also intricate retirement planning products that require ongoing management and a comprehensive understanding of features available to ensure you effectively manage overall costs and maximize benefits. We examine your policies to make sure they are properly structured to meet your needs. For variable annuities, as well as any variable life policies, we review your investment allocation to ensure it meets your investment objectives and provide you with continual management and advice.

Learn more: Insurance Audit – Frequently Asked Questions


  • In-house estate plan reviews
  • Strategies to minimize estate taxes
  • Independent trustee referral solutions
  • Legacy planning
  • Estate administration
  • Collaboration with your financial advisor, CPA, & other necessary professionals

After decades of experience counseling thousands of families on their wealth, the most common mistakes we see in financial plans revolve around estate planning. Clients spend a lifetime raising a great family and building their wealth by sacrificing, saving, and making smart decisions and then risk squandering it all because of an outdated, incomplete, or incorrect estate plan.

In order to avoid these outcomes, we have implemented a system that provides a deliverable with consistent quality where leading-edge best practices are applied both initially and on an ongoing basis for all our clients. To assure that these high standards are applied uniformly across the households that have entrusted us with their financial affairs, estate planning services are part of our comprehensive financial planning process.

At the core of our integrated wealth management system is the idea that all financial planning components are interrelated, and thus need to be carefully coordinated by a team that views them holistically. When our subject matter experts sit around a table and have a conversation about your financial plan, estate planning needs to be a central topic that considers your investments, taxes, insurance, income needs, and family profile. Without this coordinated, comprehensive approach, we see results that do not properly reflect the clients’ objectives and desired outcomes.

Perhaps more importantly, estate planning needs to effectively address considerations during your lifetime. Many plans do not comprehensively focus on the administrative dimension of estate planning. That is: “Who takes care of me and handles my affairs when I can no longer do so?”.

Your peace of mind is a ‘win’ for us.

The dispositive provisions of an estate plan spell out who gets what and when, and how they get it. While all our client families are unique, they often share the commonalities of complex, multigenerational family dynamics, and fears about mismanaging the transition of wealth to the next generations. Our experience in this area informs our recommended strategies, which are designed to prepare and protect heirs from the risks associated with sub-optimal transfers of wealth. Your plan must include a thoughtful and personal discussion about what you would like to see happen with your wealth, and how your heirs and other beneficiaries will receive it. This revolves around protections against divorce, lawsuits, creditors, and exploitation of vulnerable, disabled, or unsophisticated family members. Proper structure with appropriate provisions can make disposition of your affairs and assets a smooth and worry-free experience for those you care about.

We can also assist and coordinate selection of trustees and other professionals in the eldercare and special needs community.

Our process leads to a complete estate plan that reflects leading-edge strategies, best practices, and ongoing, proactive compliance with current law as well as attention to your family’s dynamics. The goal is to apply our experience, knowledge, and training to produce a well-thought, personalized roadmap designed to potentially maximize outcomes. This may include the following:

  • Revocable (“living”) trusts
  • Pour over Wills
  • Durable Powers of Attorney
  • Advance Medical Directives and HIPAA Privacy Releases
  • Living Wills
  • Standalone Retirement Trusts
  • Various ancillary documents, including certificates of trust and assignments of personal property

Some estate planning services may necessitate fees, however, this will be disclosed in advance for your review and acceptance. Our in-house Estate Planning Strategist Jessica Marchegiano, Esq. has established JM Law, PLLC to work with Cassaday & Company, Inc. clients and other clients with estate planning needs.


What if I already have an estate planning attorney?

One of our estate planning attorneys will review your documents with you to make sure they are consistent with your wishes. If appropriate, the attorney will provide any recommendations to you directly. From there, our attorneys can update or amend your current plan, or you can take our recommendations to an estate planning attorney of your choosing. Any planning not covered by the estate planning offering through Cassaday & Company can be provided by JM Law, PLLC for a fee.

What about clients who do not reside in Virginia, Maryland, or the District of Columbia? 

Our estate planning attorneys can review estate plans and provide guidance regardless of a client’s state of residence. However, any documents prepared by our attorneys would need to be reviewed by an attorney who is licensed in the client’s state of residence, and the client would be responsible for the cost of such review.

Alternatively, our attorneys can provide recommendations for estate attorneys licensed in the client’s state, and the client can engage those attorneys to prepare documents based on our recommendations.

Will the estate planning team be able to work with my old plan or do I need to start from scratch?

One of our estate planning attorneys will conduct a comprehensive review of your current estate plan and recommend strategies to ensure that the plan aligns with current laws and fulfills your desired outcomes. From there, the attorney will make a recommendation as to whether a revision of your current plan is sufficient, or whether changes in circumstances, objectives, or planning strategies warrant a restatement of your plan.

Can an attorney on our estate planning team serve as a client's trustee?

Because our estate planning attorneys are employees of Cassaday & Company, Inc., they are not able to act in a fiduciary capacity as trustee, co-trustee, successor trustee, or trust advisor on behalf of our clients. We will recommend other resources for your consideration that can act as trustee.


At Cassaday & Company, Inc., in addition to providing ongoing financial guidance, our comprehensive services include helping our clients make informed, thoughtful decisions about life transitions. This could be retirement decisions, job changes, moving to a new area, health & wellness impacts, relationship status changes, or anything having to do with decisions not directly related to the financial dimension of your life.

Knowing what brings you joy and fulfillment and pursuing those things with enthusiasm leads to a more rewarding and enjoyable outcome. The capstone to a good retirement plan is making sure you are addressing your emotional and relational wellbeing. We want clients to have confidence that their chosen path is based on a systematic process that produces a well-thought-out plan that allows them to pursue what is important, necessary, and joyful for them.

We regularly encounter people who can financially afford to retire, but do not because they are unsure about what they will do when they wake up and are not heading off to work. Most often this is because they do not have a clear vision about what life on the other side of retirement can look like.

To more fully assure that our clients are completely prepared for the changes in their personal and professional lives, we have added Life Transitions coaching to our suite of complimentary services. Our transitions coaching is designed to systematically assess where you are, and where you want to go, with the goals being:

  • Increasing the enjoyment of your days
  • Spending meaningful time with those who are important to you, interacting in a positive way
  • Finding outlets to connect to deeper meaning and purpose in daily life

After a comprehensive search and interview process, we are pleased to add Jennifer Landis–Santos to our team of professionals. She is available to provide coaching to discuss your personal situation and address your challenges cited above. Contact your advisor to coordinate an introductory session with Jennifer.


Download an overview of our comprehensive suite of services

Choosing us will be the easiest financial decision you'll make.


We believe that the financial planning processes are interrelated and need to be carefully coordinated. Integration requires that experts who are conversant in these areas collaborate on your behalf to make sure that:

  • Your plan is comprehensive and addresses all aspects of your financial situation.
  • Your estate planning, insurance, taxes, and investment management comport with one another.
  • As circumstances change, your plan is adaptive and dynamic.
Washington Street, in downtown Easton, Maryland.

Integration is at the heart of what we do for our clients. We believe that financial plans are incomplete without this important capstone.

As a client of Cassaday & Company, Inc., we will develop and assist you with execution of a proprietary financial planning checklist that provides a simplified and easy-to-follow roadmap to a proper execution of your short and long term financial planning goals. This checklist will:

  • Establish and execute your investment policy. Having a written investment policy based on your personal situation, goals, and objectives that’s developed in conjunction with an experienced and impartial advisor is a key component of a disciplined long-term investment plan. During this development process, we will share the findings of our studies about risk, asset allocation, diversification, and the impact of behavior on investment results. Our goal is to give you the tools you will need to make an informed decision about what is right for you.
  • Coordinate estate planning with outside attorneys to make sure your documents are up to date and consistent with current law and will fulfill your desired outcomes for you and your family.
  • Make sure that taxes are considered at all times during the process.
  • Audit your insurance, annuity, and retirement plans to make sure their provisions are consistent with your planning goals. Having this information in a central location, overseen by experts, provides clarity and ease of administration during the claims process.
  • Help you establish a potentially sustainable portfolio withdrawal based on our proprietary DIESEL® system
  • Provide guidance on Medicare, Social Security, and continuing care issues.


Imagine having a one-stop source for leading edge financial planning strategies as well as the management and monitoring of your wealth.

Our approach, developed and refined over nearly four decades, has been designed to address all aspects of your financial situation. We believe that the components of your financial world need to be carefully and comprehensively coordinated on an ongoing basis by a dedicated, highly trained, and experienced team. Our approach involves three fundamental processes: consolidation, integration, and simplification.

Happy 3 generation family in grandparents' backyard


Our clients have the opportunity to consolidate banking, brokerage accounts, retirement plans, and trusts under one roof. Our experience has been that having your financial affairs in one institution has many advantages.

  • Reduced paperwork. One source for all management and monitoring. There is no mystification around allocation, risk, or valuation.
  • Ease of monitoring. Ask yourself these questions:
    • Can you determine the returns on all of your investments, individually and collectively, at any time?
    • Do you know your overall asset allocation?
    • Do your investments overlap?
    • Are you really diversified?
      Not knowing the answers to these questions is a problem that is solved by consolidation.
  • Record keeping is centralized. No more looking for receipts or cost basis as these records are maintained for you. Also, our electronic ‘vault’ allows secure and private storage of important documents like wills, trusts, deeds, and contracts.
  • Tax preparation is simplified. Checks and charges are organized by category on one statement and easily reviewed. All taxable activity, gains and losses, dividends and interest, fees etc. are in one location and can be easily downloaded to popular tax preparation software or made available securely and privately to your tax professionals.
  • Estate administration in the event of disability or death is seamless and less stressful for your heirs.


With your assets and financial affairs in one institution, and all aspects of your wealth management integrated under the watchful eye of our experts, your financial affairs are simplified, easy to understand, managed, and monitored while benefiting from sophisticated, leading-edge, state-of-the-art best practices typically reserved for ultra-high net worth investors.