06 May You’re Their Biggest Client. That’s the Problem: A Conversation with Taylor Smith
Why do so many business owners believe their advisory structure is working when it isn't?
Because nothing is visibly broken, and the current structure has not been stress tested.
The financial advisor (or advisors) who built the relationship when the family’s net worth was $8M is still at the table when the family’s net worth is $35M. The estate plan the attorney drafted in 2014 is still “the plan” and has not been updated. The CPA has been doing the bookkeeping and strategy, while filing the same tax returns for years. The investment accounts are spread across two or three institutions and “financial advisors” because it’s always been that way. The operating business is growing, but nobody has mapped it against the investment portfolio. On the surface, everything looks fine.
The problem is that most advisory teams were built for a version of the client that no longer exists. The financial advisor, the CPA, and the estate attorney were each the right fit at a certain level of complexity and net worth, but the family surpassed that threshold years ago. Nobody called a meeting. Nobody raised a hand to say, “I’m no longer comfortable giving you advice.”
Why wouldn't a financial advisor, CPA, or estate attorney tell a business owner they've outgrown them?
Because each member of the team has a version of the same problem, and the cost of the honest conversation is too high for any of them to bear voluntarily.
The Financial Advisor – At $30M, $50M, or $100M, a single family is frequently the largest, or one of the largest relationships a financial advisor, wirehouse team, or independent RIA carries. Referring out, flagging limitations, or recommending a different structure puts at risk the entire AUM relationship and thousands of dollars in commissions. It’s worth noting that many financial advisors are still operating on commission or selling products, even if those products are hedge funds, private equity funds, or venture capital funds, which means their recommendations are shaped by what pays them or their firm the most, and not necessarily what the business owner needs for the family.
The CPA – The firm that’s done the bookkeeping for the business and filed the tax returns for fifteen years isn’t going to volunteer that the tax strategy has never been coordinated with the investment advisor, or that the business structure hasn’t been stress-tested against the estate plan, or that it wasn’t created with the next generation in mind. They probably won’t say, “I’m the right CPA for your business, but you need a different CPA for your family’s personal tax planning, multi-generational planning, and wealth transfer.” That requires a level of self-awareness about specialization not contemplated in the engagement structure.
The Estate Planning Attorney – Many estate planning attorneys naturally build their practices around a particular client profile, a net worth range, a certain balance sheet complexity, or a planning need. There is a real possibility that the attorney who drafted your documents ten or fifteen years ago has been outgrown by your family, business, and balance sheet of today. The plan is technically still in place, but needs to be altered, enhanced, or changed. Nobody has called to ask whether the current plan still works.
So instead, each of them manages perception or avoids the conversation all together. They keep the illusion in place, as they don’t want to self-select to leave the team. They tell the family what they want to hear: that the plan is solid, that nothing needs to change. And when the family says, “I just want things to be simple,” the financial advisor hears permission, and so does the CPA, and so does the estate attorney.
What does "I just want things to be simple" actually means for a business owner or newly wealthy family?
It’s one of the most diagnostic statements we hear, and it almost always means one of four things:
Family Quarterback – The business owner has been carrying coordination responsibilities they are no longer equipped to own. They’re serving as the de facto relay between a financial advisor, a CPA, and an estate attorney who don’t talk to each other. They’re attempting to manage their advisors, but are stuck in a dysfunctional game of telephone, using words and phrases they do not understand. They’re exhausted by it and know that complexity is growing.
Don’t Know Better – The business owner has never seen what a well-structured system actually looks like and is unaware that there are infrastructures and businesses designed to alleviate this tension. For most business owners, the advisory structure grew organically alongside the business; a financial advisor added here, an estate attorney there, a CPA somewhere else. “Simple” is the only vocabulary they have for “less friction.”
Family In Transition – Complexity has begun to surface family tension. Often it’s around the business, the next generation, family or entity governance, and who is involved at what level. “Keeping things simple” is a way of keeping that tension suppressed. As wealth compounds and complexity occurs, the tension compounds.
Comfort Zone – It becomes apparent that the family or business owner will need to upgrade or change some members of the advisory team. Many of these advisors have become friends and confidants and have served the family for years, and it creates internal tension for the family to need to fire a member of the team. They struggle with the desire to keep things as is, but they know they need to upgrade their system, infrastructure, and team. Rather than changing team members, they would rather “keep things simple,” though they know there’s opportunity costs to remain in their comfort zone.
All four of these are structural problems. None of them get better by keeping the structure and team in place.
What is the business ownership blind spot that most financial advisors miss?
JPMorgan’s 2026 Global Family Office Report puts a specific number on it: 58% of family office families own a separate operating business. Only 48% of those families consider the business when constructing the investment portfolio.
That means most business-owning families are running an investment strategy entirely disconnected from their single largest asset. The concentrated, illiquid risk in the operating business — industry concentration, key-person exposure, succession uncertainty — is almost never hedged or complemented by the liquid portfolio. It’s simply not taken into account.
The financial advisor who manages the investment accounts almost never has visibility into the business or tax matters and rarely asks for it. The CPA who files the business’ and owner’s returns rarely coordinates with the financial advisor on portfolio construction. The estate attorney who drafted the plan rarely knows how either of the other two are thinking about the family’s future.
The question that reframes this for every business owner: Is your investment portfolio designed around your business, or despite it? Most have never been asked. Neither has their financial advisor.
What are the structural tells that a business owner has outgrown the advisory team?
These show up consistently, even when nothing has visibly broken:
- Estate Plan Outdated – An estate plan that hasn’t been reviewed or stress-tested since the last major tax law change, drafted by an attorney whose practice is built around a different client profile than where the family is today.
- No Tax Coordination – The financial advisor has never factored the business taxes into the portfolio construction or the design of qualified accounts.
- No Coordination Between Institutions – Investment accounts at multiple institutions with multiple “financial advisors” and no coordination or consolidation.
- Siloed Professions – A financial advisor, CPA, and estate attorney who don’t communicate directly with each other because no one has established that expectation, or they aren’t even aware of each other, or there is no infrastructure for sharing information.
- Client is the Hub – The business owner, matriarch, or patriarch is serving as the primary hub or relay between multiple advisors.
- Hidden Fees and Commissions – A “family office” relationship at a wirehouse, RIA, or broker dealer, is full of layered and hidden fees the family has never noticed, discussed, or had independently reviewed.
- No Charitable Design – The family is charitable, but there has been no charitable or tax design, and charitable giving is not integrated into the estate plan, investment, or estate design.
None of these require a crisis to surface. They require someone who knows what they are looking for to ask the right questions.
What is the incentive structure that keeps the financial advisor, CPA, and estate attorney quiet?
It’s worth being direct about this because most content in this space isn’t.
Each member of the advisory team has a version of this problem, and each version is different. The financial advisor’s revenue and practice valuation are tied directly to the AUM relationship, and referring the client out means losing the relationship. Many are also operating on commission or within a product-based model, which means the recommendations they make are bounded by what they can offer. There are hidden fees throughout the financial service industry, and it takes a trained eye to understand the layered fees, hidden fees, and commissions.
The CPA who has done the bookkeeping and filed the tax returns for years has never been engaged to coordinate across disciplines, and volunteering that scope gap creates an odd and risky conversation.
The estate attorney who drafted the documents years ago built their practice around a certain complexity and level of wealth, and the family has likely grown past it without anyone making that observation.
So, the incentive across all three advisors is to maintain, not to disrupt. To manage perception, not complexity. To keep the family comfortable rather than informed.
This is not a character indictment. In many cases, the financial advisor, CPA, and estate attorney each genuinely believe they are doing good work. And within their scope, they may be right. The problem is there are significant gaps in information, nobody owns the full picture, and the family or business owner bears all the risk. The business owner who assumes their plan is solid and their team is aligned may be one liquidity event, generational transition, or death away from discovering how incomplete that reality is.
What does a well-structured advisory system actually look like for a family or business owner?
It can feel simpler. But that’s the output of informed, intentional work and well-managed complexity, not the absence of it.
The characteristics are specific:
- Informed Quarterback – A single point of coordination that holds the family’s full picture across investment, tax, legal, estate, operating business and charitable areas, not as siloed disciplines but as an integrated strategy.
- Integrated Portfolio – An investment portfolio explicitly designed around the operating business, accounting for concentration risk, liquidity needs, tax implications, and succession timeline.
- Coordinated Team – The financial advisor or advisors, CPA, and estate attorney who communicate directly with each other, with the business owner removed from the relay.
- Dashboard – An independent, consolidated view of the full balance sheet, including the business, fee structures, entity exposures, and liabilities.
- Appropriate Estate Plan – An estate plan that reflects current law, current level of wealth, current family structure, and current business structure, drafted or reviewed by an attorney whose practice is built for the appropriate level of complexity.
- Charitable Giving – A charitable strategy structurally integrated into the wealth, tax, and estate design, and not treated as a separate activity.
When these elements are in place, the business owner stops being the coordinator. That’s what “simple” actually feels like.
How should a family or business owner evaluate whether they have the right structure?
Start with these questions:
- Is your investment portfolio designed around your business, or does it simply ignore it?
- When did your estate attorney last review the plan with fresh eyes, not to confirm it’s fine, but to stress-test it against your current level of wealth, family dynamics, business structure, and current law?
- Do your financial advisor, CPA, and estate attorney communicate directly with each other, or do you relay information between them?
- Can you produce a consolidated view of your full balance sheet, including the business, all fees, entity structures, and liabilities, in one document?
- Has anyone mapped the total cost of your current advisory structure, including indirect or hidden fees inside investment vehicles?
- Are your charitable goals integrated into your financial plan, estate plan, and tax design, or does it operate separately?
If those questions are hard to answer, that’s the answer.
What is the first step for a family or business owner that suspects something isn't working?
The first step is not to replace the team. It’s to get an independent review and understanding of the full picture.
Not a second opinion from another financial advisor in the same type of structure. An independent, consolidated review that looks at the entire system: what’s there, what’s missing, how the financial advisor, CPA, and estate attorney are or aren’t working together, how the balance sheet, level of wealth, and business are all factored in, and whether the people responsible for it are equipped for where the family’s net worth and complexity actually are today.
The worst case is to discover the gaps through a crisis, a liquidity event, a generational transition, or a business succession that arrives before the structure is ready for it. The family or business owner that navigates this well finds the gaps because someone asked a question nobody has asked before.
Final Thought
You will not receive a signal that it’s time to ask deeper questions.
No postcard arrives. No moment announces the shift. The financial advisor who built the relationship when the net worth was lower and the portfolio was simple is not going to schedule a meeting to tell you they’re no longer the right fit. The CPA who has never been asked to coordinate with the investment side is not going to raise that question unprompted. The estate attorney whose practice is built around a different complexity level than where your family is today is not going to volunteer that observation.
The family of multigenerational wealth and business owners that navigate this well are the ones who stop waiting for something to break and start asking what they’ve never been asked.
The individuals that figure this out don’t just find better advisors. They build a different infrastructure. One coordinated around who the family is and what the business is building, not just what they currently own.
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