BY PHIL SHETSEN
In Part 1 (March 2026 Issue), we met the Jones family at a stage where the business was working and planning was still forming.
Now, ten years later, the picture has changed. The business has grown, the balance sheet has expanded, and the decisions in front of the family carry more weight. In this chapter of the the business, the focus shifts from building momentum to managing complexity. Success introduces new risks, and earlier planning decisions begin to shape what’s possible next.
With a decade passed, the Jones family is in a very different position. Robert is now 56 and the business has grown significantly, both in size and in importance to the family’s overall wealth. What was once a strong operating company is now a central asset with real implications for retirement, taxes, and legacy.
This is where decisions start to carry weight. Anecdotally, this is where many operators who founded their businesses in the 1990s or early aughts are—not quite at retirement but big enough to consider their next phase.
Where the Family Stands Now
The business has scaled: revenue has doubled to $18 million, with $1.8 million in EBITDA. The company is now valued at approximately $6.9 million, with $3 million in assets and $1.5 million in debt. The real estate has appreciated as well, now valued at $2.5 million and still leased to the business.
Personally, the picture has strengthened across the board. The primary residence in New Jersey and the vacation home in Florida are now both owned outright. The investment portfolio has grown to $3 million. Retirement assets have increased to $1.5 million, split evenly between Robert and Diana. The car collection has expanded to roughly $650,000.
What’s Changed
The business is no longer just a source of income; it’s a concentrated asset that represents a significant portion of the family’s net worth.
At the same time, the family itself has evolved.
❱ One child is now married with children and has no involvement in the business
❱ One child is actively working in the company and may be a future successor
❱ One is finishing college and still finding direction
The dynamics that were theoretical are now real.
A New Set of Questions
At this stage, the questions are no longer about structure, they’re about the future.
❱ Who will control the business, and when?
❱ How should ownership be divided between children with different levels of involvement?
❱ Is equal treatment the right approach?
❱ How much of the family’s wealth is too concentrated in a single asset?
❱ What happens if something forces a transition before the family is ready?
There’s also a growing awareness around taxes. The estate has expanded meaningfully and while it may still sit near or below current federal exemption thresholds, that line is not guaranteed to stay where it is.
Where Complexity Starts to Show
The business now carries enough value that any transfer, whether during life or at death, has tax implications. The gap between the child in the business and the children outside of it creates tension around fairness and control, multiple properties across states introduce administrative and legal complications, and the growing balance sheet increases exposure, even if nothing has gone wrong.
This is where the Jones family needs to move from general awareness to defined strategy.
That typically includes:
❱ Establishing or updating a formal succession plan that outlines who will run the business and how ownership transitions over time
❱ Creating or revising shareholder and buy-sell agreements to define what happens in the event of death, disability, or voluntary exit
❱ Introducing trust-based planning to begin separating control, benefit, and tax exposure across generations
❱ Reviewing beneficiary designations and titling of assets to ensure alignment with overall estate goals
❱ Evaluating life insurance not just for income replacement, but as a tool for liquidity and business continuity
❱ Coordinating across advisors
Growth creates options, but it also reduces flexibility. The larger the business becomes, the harder it can be to divide. The more valuable the estate becomes, the harder it can be to transfer efficiently. The more complex the family becomes, the harder it can be to keep things fair without a plan.
Why This Phase Is a Turning Point
This is the point where many business owners realize they don’t just own a company, they own a system of assets, responsibilities, and future obligations. Left uncoordinated, that system creates friction. Handled intentionally, it creates consistency.
The Jones family is now deciding how to plan without disrupting what they’ve built.
In Part 3, the focus shifts again. The conversation moves beyond structure and into legacy, control, and what happens when a transition is no longer hypothetical—let’s see what happens. [CD0626]
Phil Shetsen is the President of Bona Vita Benefits. He can be reached at
