Practice Succession

You Spent Decades Building Something Worth Protecting.

Your clients didn't just hire you. They trusted you with the decisions that matter most in their lives. Now you're thinking about stepping away, and the question keeping you up at night isn't about the money. It's whether your clients will be okay after you're gone.

See if You’re a Fit

Orange note reads 'Business Success Plan' beside a calculator and money, on a wooden desk with colorful sketches and charts.

Featured In

Wooden letter blocks spell 'SUCCESS' in a row, with a final split block showing 'FUL' and 'TION' to hint at 'successful'.

The problem with most succession options? Most of the market is aggregators and roll-up firms optimizing for AUM.

They'll make you an offer. They'll promise continuity. And then your clients will spend the next two years getting passed between relationship managers they've never met, inside a brand you barely recognize.

That's not a legacy. That's a transaction. You deserve a buyer who sees your practice the way you do: as a group of real people who need real financial planning from someone who actually knows them.

Chesapeake Financial Planners

5.0

Based on 11 reviews

review us on

Joyce Ducksworth

1 month 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

1 month 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

2 months 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

3 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

3 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

7 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

8 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.

Mark and Jeff at Chesapeake Financial Planners

We're actively looking to acquire financial planning practices and books of business from advisors who are ready to retire. Not to grow a portfolio of acquisitions. Not to hit an AUM target. To find well-run practices with good clients and take care of them the way their advisor did.

Mark is a licensed CPA

Tax planning is built into the conversation from day one, not outsourced to a referral. Your clients' situations stay in-house.

Jeff has an AEP

As an Accredited Estate Planner, Jeff ensures our clients with estate planning needs get real depth, not a checkbox.

Local and Staying Local

Baltimore/Annapolis corridor. No national platform, no brand consolidation. Your clients stay with advisors who know the area.

You'll Know Who's Taking Over

Your clients get Mark and Jeff, not a brand that may change hands again in three years.

What We're Looking For

We work best with practices that look something like this:

Fee-based or fee-only financial planning practices in the Mid-Atlantic region

Solo advisors or small teams planning a retirement transition over the next 1–5 years

AUM-focused books or comprehensive planning relationships, not primarily transactional

Advisors who want their clients to land with people who actually do financial planning, not just investment management

If that sounds like you, we'd welcome a conversation.

Two businessmen in blue suits sit at a table reviewing documents together.

How a Transition Typically Works

We've kept the process straightforward on purpose.

Initial Conversation

We talk through your practice, your timeline, and what a good outcome looks like for you. No pressure, no pitch deck.

Practice Review

We look at your client base, fee structure, and planning approach. We're evaluating fit as much as financials.

Deal Structure

We work through valuation, payment terms, and timeline. Earn-outs, phased buyouts, and consulting arrangements are all on the table.

Client Introduction

You introduce us to your clients on your terms. The goal is continuity, not disruption.

Transition

We work alongside you through the handoff. Most clients don't notice a rough edge because there isn't one.

What You Get on the Other Side

Your clients are with advisors who will actually plan for them, not manage them into a service tier.
The deal was structured fairly without forcing you to work five more years to earn it.
Your name stays associated with good outcomes long after you're gone.

Don't Wait Too Long

Advisors who start this conversation 2–3 years out have more deal structure options, more time to introduce a buyer to clients gradually, and more flexibility to shape what the transition looks like. Waiting until you're ready to stop working next year isn't wrong. But it narrows what's possible

Frequently Asked Questions

Most financial planning practices and books of business sell in the range of 1.5–2.5x annual recurring revenue. The specific multiple depends on several factors: client retention risk, fee structure (fee-only practices typically command higher multiples than commission-based books), client demographics, average relationship size, practice age, and how the transition is structured. A practice with long-tenured clients, predictable recurring revenue, and a clean fee-only model will attract a stronger valuation than a transactional book with high turnover. We don't apply a fixed formula. We look at the whole picture, including what the transition structure looks like, because a well-structured earn-out can close the gap between what a seller wants and what the numbers support.

Not always. Earn-outs are common in financial advisor succession transactions because they align the seller's incentives with client retention during the transition period. But we don't treat them as a requirement. For practices with strong client relationships, predictable retention, and a clean fee structure, upfront or largely upfront structures are on the table. Our goal is a deal that lets you actually retire on your terms, not one where you're watching a retention clock for the next three years. We also consider phased buyouts, consulting arrangements, and hybrid structures depending on what makes sense for both sides. What's right depends on the size of the practice, the seller's timeline, and how hands-on the transition needs to be.

Your clients continue working with fiduciary, fee-only financial planners who do comprehensive financial planning. They are not moved to a call center, assigned to a junior associate, or folded into an automated portfolio management platform. Chesapeake Financial Planners operates as a relationship-driven, planning-first firm. That means your clients get an advisor who knows their situation, understands their goals, and engages with the full picture of their financial life, including tax planning, estate planning, retirement income strategy, and investment management. The whole point of this kind of succession is that your clients land somewhere that operates the way you did. That's what we're built to do.

Yes, and in many cases it's the best outcome for clients. A gradual handoff, where the selling advisor stays involved in a part-time or consulting capacity during the transition period, tends to produce better client retention and a smoother experience for everyone. We're open to arrangements that keep you involved for 6 months, 12 months, or longer, depending on what makes sense for the practice. The structure should serve the clients first and work for both parties second. If you want a clean break and a shorter transition, we can work with that too. There's no single right answer, and we don't approach these conversations with a fixed template.

Probably yes. We're not looking for a $500M AUM mega-practice or a firm with a large support staff. What we're looking for is a well-run book of clients who have a genuine planning relationship with their advisor and need someone to take care of them after the transition. A smaller practice with 40–80 households and strong client relationships is often a better fit than a large, transactional book with high turnover. Size is not the primary filter. Quality of relationships, compatibility with our planning approach, and client fit matter more. If you've built a practice you're proud of, it's worth a conversation regardless of AUM.

Earlier than most advisors expect. Financial advisors who begin exploring succession options 2–3 years before their target retirement date typically have significantly more options available to them. Starting early allows time to structure the deal properly, introduce the buyer to clients gradually before the formal transition, and work through any licensing, registration, or compliance considerations without being rushed. It also gives the seller more negotiating leverage. If you're within 12 months of wanting to retire, it's not too late, but some of the most attractive succession structures require lead time to execute well.

Our primary focus for practice acquisitions is the Mid-Atlantic region, including Maryland, Northern Virginia, Delaware, and Southern Pennsylvania. This geographic focus is intentional. We believe that serving clients well over the long term is easier when the advisors know the local tax landscape, the regional estate planning environment, and the community. That said, if you're just outside this footprint, it's still worth a conversation. Depending on how your book is structured and how the transition would work, geography matters less than it might initially seem. We evaluate each situation individually.

We don't have a fixed credential requirement on the seller's side. What matters more than what licenses you hold is the nature of your client relationships and how your practice is structured. A fee-only RIA with comprehensive planning relationships is a strong fit regardless of whether the selling advisor holds a CFP, ChFC, or no planning designation at all. We'll work through any custodian transitions, regulatory notifications, or registration requirements as part of the due diligence and deal process. If your practice operates under a broker-dealer or has commission-based revenue, that doesn't automatically disqualify it, but it does change how a transition would be structured and what the timeline looks like.

It depends on the practice and the role your team plays. For practices where support staff have built meaningful relationships with clients, keeping them through the transition often produces better outcomes for everyone. Staff who know the clients, understand the workflows, and have established trust are an asset in a succession, not just overhead. We approach staffing decisions individually and don't have a blanket policy of retaining or releasing employees as part of an acquisition. If retaining your team is important to you, that's a conversation worth having early. It can often be factored into the deal structure in a way that works for both sides.

Completely confidential until you decide otherwise. Advisors exploring a practice sale have legitimate reasons to keep those conversations private: clients may react with concern, staff may worry about their jobs, and competitors may use the information against you. We treat every conversation about a potential acquisition with the same level of confidentiality we extend to our own clients. Nothing is shared with third parties without your explicit consent. The due diligence process involves a review of your practice data, but that information stays between us. You control the timing of when clients, staff, and your professional network learn about a transition, and we support whatever timeline makes sense for you.

*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

Practice Succession

You Spent Decades Building Something Worth Protecting.

Featured In

Mark and Jeff at Chesapeake Financial Planners

Mark is a licensed CPA

Jeff has an AEP

Local and Staying Local

You'll Know Who's Taking Over

What We're Looking For

How a Transition Typically Works

Initial Conversation

Practice Review

Deal Structure

Client Introduction

Transition

What You Get on the Other Side

Don't Wait Too Long

Frequently Asked Questions

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

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