Protecting More Than a Lake House

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The Prosperity Briefing

Keeping You Informed And Ahead

A Business, a Lake House, and a Fifty-Year Plan

July 28, 2026
6 min read

A client recently told me about the past Fourth of July his family celebrated at their lake house. Three generations were together. His grandchildren were cannonballing off the dock, his daughter-in-law was tending the grill, and he sat on the porch beside his wife, watching the life they had built unfold in front of them. I have changed a few details to protect the family’s privacy, but the question behind his story is one I hear often.

He did not build his business, or preserve that lake house for all these years, by managing money the way most financial columns describe it: a budgeting app here, a savings tip there. For a business owner like him, financial planning was never primarily about restriction. It was about protecting what his work had made possible: the freedom to gather, the security to care for the people he loved, and the hope that, decades from now, his grandchildren might sit on that same porch and watch their own children cannonball off the dock.

After more than three decades of working with business owners and their families, I have learned that the hardest financial questions are rarely just financial. They are questions about identity, security, responsibility, and legacy.

The moments that matter most rarely begin with a spreadsheet. They begin with a question like the one my client asked not long after that weekend:

"If something happened to me tomorrow, would my family still
have this lake house, and still have these Fourth of Julys, fifty years from now?"

- A Client, after his family's Fourth of July together

That is a wealth management question. It simply does not look like one at first.

One of my favorite questions to ask families and entrepreneurs is, “Why is money important to you?” Then I keep asking, not to be repetitive, but because the first answer is rarely the real answer.

Years ago, I asked one client that question six or seven times. Eventually, his eyes filled with tears. He told me that he had grown up in Europe in the aftermath of the Depression, with almost nothing, and he had spent his entire life determined never to feel that vulnerable again.

That was his real why.

Money was not about accumulation. It was about safety. It was about dignity. It was about protecting his family from a fear he had carried since childhood.

"Meaningful wealth planning must begin with more than
assets, tax returns, and tax strategies. It must begin with
understanding what money is meant to protect."

The Questions That Actually Matter

Once you sit with questions like this, the usual budgeting conversation starts to feel small. It is not only about trimming expenses or building a rainy-day fund, though those things matter too. It is about a handful of harder questions that many families never get around to asking until something forces the issue:

If the business stopped generating income tomorrow, would the family’s lifestyle have to change? If the lake house is meant to pass to the grandchildren, is there a plan for that—or only an assumption? If something happens to the person who built the business, does it transition according to a plan, or does the family have to make major decisions in the middle of a crisis?

These are not comfortable questions to raise at a cookout. But they are far easier to answer around a conference table today than around a hospital bed—or after a funeral—when emotions are high and time is short. But they help determine whether the family is still gathering there twenty-five years from now—or whether the property eventually becomes a source of confusion, conflict, or an unplanned sale.

Know Someone Who's Building Something Worth Protecting?

What We Talk About Before We Talk About Numbers

Most of the families and business owners we work with did not come to us because they needed help spending less. They came to us because they had built something real—a company, a piece of property, a body of wealth, and a life their children and grandchildren had grown up inside of—and they wanted a thoughtful plan for keeping it intact.

That work starts with conversations, not spreadsheets. Who actually wants to run the business someday, and are they ready? What does the family want the lake house to mean in twenty years: a gathering place or a source of conflict? Is there enough liquidity to preserve the property and support the family without forcing a sale? Are tax, estate, investment, insurance, and business plans working together—or were they created separately and never truly coordinated?

A lake house can become a blessing, but shared family property can also become a source of disagreement over expenses, usage, upkeep, and control. That is a very real concern for affluent families, and mentioning it demonstrates practical experience. Preserving the property is only part of the challenge. A good plan must also preserve the relationships around it by addressing who will use it, who will manage it, who will pay for it, and what happens when one family member wants out.

Once those questions have honest answers, the numbers become much easier to plan around. We help business owners and their families connect the business, the property, the tax strategy, the estate plan, and the wealth behind them into one coordinated plan built to last.

A Relationship Built for Complex Families

Not every family needs this kind of planning, and we are not trying to be everything to everyone. We work closely with a limited number of closely held business owners and high-wealth families because this work takes time, trust, judgment, and a real relationship. It does not lend itself to a one-size-fits-all process, and we have never tried to make it one.

If your family has built something worth protecting—a business, a property, or a legacy—and you want a partner and trusted advisor who thinks in terms of decades rather than tax seasons, that is exactly the kind of conversation we are built to have.

My client’s family will gather at that lake house again next summer. The purpose of thoughtful planning is to make sure those moments do not depend on everything continuing to go exactly right.

If your family has built a business, a meaningful property, or a body of wealth worth protecting, it may be time to ask whether the plan behind it is as strong as the asset itself.

And if you know a business owner or family who is approaching a transition—selling a company, passing ownership to the next generation, preserving family property, or trying to coordinate tax, estate, investment, and business decisions—we would be honored to be part of that conversation.

Until next time – Peace,

Eric

Principal, CPA/PFS

(504) 586-3050

erigby@therigbygroup.com

One Response

Scout says:

July 29, 2026 at 11:11 am

Great post!

Reply

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The Prosperity Briefing

Keeping You Informed And Ahead